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In part two of our miniseries on execution, executive coach Audrey Camp returns to unpack the hardest part of running a company: Focus. Why is it so elusive, even for the most driven founders? How do OKRs help cut through the noise? And what happens when teams lose focus—and motivation?Lucas and Audrey dig deep into how execution thrives when everyone is aligned, and how focus isn't just a mindset—it's a system.In this episode you'll learn:Why most companies are 30% less effective than they could be—due to lack of focusHow OKRs help organizations say no to distractions (even tempting ones)The difference between being busy and being effectiveHow to recognize and reward the right work, not just the visible or heroicWhy performance struggles are often rooted in poor focus, not poor effortAbout Audrey Camp:Audrey is an executive coach working with scaleups across Europe. With a background in communication and deep experience from Cognite, she helps leaders grow into their roles, define what matters, and execute with clarity and impact.Host: Lucas Weldeghebriel, editor in chief and CEO in Shifter.
In his first month as Head of Talent Acquisition at Sam's Club, Steve White joined our podcast at UNLEASH to reflect on what it really takes for TA to be seen as a business partner, not just a service function. From embedding in the business and aligning to OKRs, to balancing EVP with hyper-local “MVPs,” Steve shares how TA can drive transformation by showing up differently and thinking bigger.
Daniel Dippold, Gründer von EWOR, gibt dir Einblicke in den Aufbau eines der selektivsten Founder Fellowships Europas. Mit mehr als 100 Millionen Dollar Funding teilt Daniel, wie EWOR aus 50.000 Bewerbungen die besten 30 Fellows pro Jahr auswählt. Er erklärt, warum mathematische Modelle in der Gründer-Selektion wichtig sind, wie man ein hochperformantes Team aufbaut und warum EWOR sich bewusst als Venture und nicht als Fonds versteht. Mit bereits einem Unicorn im Portfolio nach nur zwei Jahren zeigt Daniel, wie EWOR durch die drei Säulen Attraction, Selection und Amplification systematisch die nächste Generation von Milliarden-Dollar-Unternehmen aufbaut. Was du lernst: Gründer-Selektion & Bewertung: Die drei Säulen erfolgreicher Gründer: Obsession, Resilienz und unfaire Vorteile Wie EWOR aus 50.000 Bewerbungen die Top 30 Fellows auswählt Die Bedeutung von empirischen Daten in der Gründer-Evaluation Organisationsaufbau: Die drei Kernbereiche: Attraction, Selection, Amplification Wie man mathematische Modelle für Organisationsentwicklung nutzt Die Bedeutung von OKRs und KPIs im Venture-Building Team & Kultur: Warum Top-Performer nur mit anderen Top-Performern arbeiten Die Bedeutung von psychologischer Kompatibilität im Team Wie man ein hochperformantes Team aufbaut und führt Produktivität & Führung: Daniels System für persönliche und organisatorische Produktivität Die Bedeutung von regelmäßiger Reflexion und Anpassung Wie man als Gründer konsistent Progress demonstriert Investment & Skalierung: Warum EWOR sich als Venture und nicht als Fonds versteht Die Bedeutung von Evergreen-Strukturen für langfristigen Erfolg Wie man ohne klassisches Board erfolgreich skaliert ALLES ZU UNICORN BAKERY: https://zez.am/unicornbakery Mehr zu Daniel: LinkedIn: https://www.linkedin.com/in/danieldippold Website: https://www.ewor.com/ Die bisherigen Folgen mit Daniel & Mike gibt's hier: Join our Founder Tactics Newsletter: 2x die Woche bekommst du die Taktiken der besten Gründer der Welt direkt ins Postfach: https://www.tactics.unicornbakery.de/ Kapitel: (00:00:00) So kannst du EWOR trotz 50k+ Pitches noch begeistern (00:06:38) Trustaufbau & Beweisarbeit für die Zusammenarbeit mit EWOR (00:16:41) Wie beweist man zwischen den "Marktschreiern", dass man nicht nur laut, sondern auch gut ist? (00:20:59) Softskills & die Qual der Wahl: Wie findet EWOR die 30 besten aus 50k? (00:26:49) Darum geht EWOR nicht den klassischen Fonds-Weg (00:38:30) Daniels Learnings & Überraschungen aus mehreren Zehntausend Gründungen (00:49:48) Daniels Einordnung der KI-Bubble in die aktuelle Marktsituation (00:54:58) Die Balance zwischen alter Begeisterung & neuen Ideen (01:01:23) Wie entscheidet Daniel über Informationsbeschaffung? (01:06:01) So funktioniert EWOR als Organisation (01:17:17) Daniels Productivity-System
Jess Larsen sits down with real estate innovator and PropTech entrepreneur Rob Finlay to dive into his new book, Beyond the Building. They explore why top-performing real estate operators are thinking more like tech founders—and how to build enterprise value through adaptability, data, and leadership. From capital strategy to OKRs, Rob shares the mindset and mechanics behind scaling smarter in today's evolving market. Learn more about your ad choices. Visit megaphone.fm/adchoices
"We can't just run an office in chaos." Connect With Our SponsorsGreyFinch - https://greyfinch.com/jillallen/A-Dec - https://www.a-dec.com/orthodonticsSmileSuite - http://getsmilesuite.com/ Summary In this episode, Jill and Casey Bull discuss the importance of effective team management and goal setting in orthodontic practices. Casey shares insights on implementing OKRs (Objectives and Key Results) to enhance team performance and accountability. They explore the concept of '10 state' to define excellence in roles, the significance of structured team meetings, and the need to prioritize big goals over daily tasks. The conversation emphasizes fostering a culture of accountability while maintaining a supportive environment for team members. Connect With Our Guest CascadEffects - https://www.cascadeffects.com Takeaways Casey Bull emphasizes the need for impactful change in orthodontic practices.OKRs help clarify objectives and measure progress effectively.Leading KPIs are crucial for proactive management.Defining a '10 state' helps teams strive for excellence.Structured meetings enhance team accountability and focus.Rocks and sand analogy illustrates prioritization of goals.Accountability should be framed as support, not criticism.Self-care is essential for productivity and balance.Open-mindedness can lead to better practices and outcomes.Effective communication tools can streamline team interactions.Chapters 00:00 Introduction to Cascade Effects and Casey's Journey03:07 Understanding OKRs in Orthodontic Practices06:00 Implementing OKRs: Practical Steps for Success08:55 The Importance of Measuring Team Performance11:58 Defining the 10 State: A New Approach to Goal Setting19:29 Understanding the Big Picture in Team Dynamics21:26 The Importance of Structure and Goal Setting22:54 Effective Team Meetings: Engaging Everyone25:54 Navigating Team Accountability and Feedback29:01 Implementing Rocks: Prioritizing Big Objectives33:11 Balancing Accountability and Team Autonomy Are you ready to start a practice of your own? Do you need a fresh set of eyes or some advice in your existing practice?Reach out to me- www.practiceresults.com. If you like what we are doing here on Hey Docs! and want to hear more of this awesome content, give us a 5-star Rating on your preferred listening platform and subscribe to our show so you never miss an episode. New episodes drop every Thursday! Episode Credits: Hosted by Jill AllenProduced by Jordann KillionAudio Engineering by Garrett Lucero
Este podcast es posible gracias a Santander:https://online.bancosantander.es/landings/cuentas/cuenta-autonomos/En este episodio acompañamos a Jordi, Bernat e Ilya recién llegados de su off-site, cerca de la Costa Brava.Bernat y Jordi fueron hace unas semanas a suecia con fundadores que ya superan los 100 millones de dólares de ARR y con un prodigio que, sin escribir una sola línea de código, ha llevado su aplicación no-code a esa misma cifra en apenas nueve meses. Hablamos del talento en IA: Apple acaba de crear sus “Super-Intelligence Labs” y pone sobre la mesa cheques de ocho dígitos para seducir a cerebros que hoy trabajan en OpenAI, una maniobra que Meta y otras big tech se apresuran a imitar. De ahí pasamos a desnudar las tripas de Figma y su S-1: 821 millones de ARR, un crecimiento del 48 % y márgenes brutos del 90 %, aunque con una factura anual en AWS que ronda los 100 millones. Compartimos, además, las lecciones de organización de producto extraídas de un gigante europeo con miles de ingenieros: OKRs bien planteados, “tríos” que combinan diseño, ingeniería y negocio, y managers que por fin cargan objetivos reales.También hablamos sobre los riesgos del trabajo remoto: entrevistas atendidas por bots, identidades falsas y los métodos para detectar fraudes antes de que el equipo pague las consecuencias. Volvemos a la luz con la adrenalina de los prototipos y los deadlines semanales: enseñar maquetas y vídeos cada viernes convirtió un proyecto etéreo en un motor de hype colectivo. También desgranamos tácticas para evitar hallucinations en los LLMs cuando te juegas datos internos. Y, al final comentamos la fiebre de Granola, la herramienta que graba y resume todas las llamadas; el meme eterno de que “Nvidia siempre gana”; y la llegada a X de un ex-founder experto en viralidad juvenil que promete construir el próximo gran producto desde dentro de la plataforma.
In this first episode of a four-part miniseries on execution, we dive deep into what makes goals actually work. Executive coach and OKR expert Audrey Camp joins Lucas to unpack how leaders can transition from ambition to alignment. They explore what distinguishes a SMART goal from a “SART” one, why meaning matters more than measurability, and how goal ownership can unlock true progress.Audrey draws on experience from advising growth-stage companies across Europe and her past work at Cognite, to share hard-won lessons on goal-setting, communication, and leadership development.In this episode you'll learn:Why many startup leaders are "untested" and how that impacts goal executionWhat makes a goal actually effective—and why measurability alone isn't enoughThe real power of OKRs and why they fail more often than they succeedHow to create shared ownership and meaningful alignment in your organizationThe importance of stretch goals and how to calibrate ambition with reality
One of the biggest pain points for first-time founders is a lack of structure within their business. One of the most popular frameworks for quickly creating structure is the Entrepreneurial Operating System (EOS), but does it really live up to the hype? In this episode of In Demand, Asia and Kim do a deep dive into EOS. They break down its key components, where it works (and where it doesn't), and why most founders should treat it more like a toolbox than a strict rulebook. Got a question you'd like Asia to unpack on the podcast? Record a voicemail here. Links: DemandMaven EOS Worldwide Traction by Gino Wickman - the book introducing EOS Chapters (00:00:25) - Rediscovering campaign anxiety.(00:06:00) - EOS overview: what it is and why a client recently reached out asking about it.(00:11:00) - “Right person, right seat” explained.(00:15:45) - Issues tracking.(00:20:00) - Where EOS can fall apart for small teams.(00:29:30) - The parts of EOS that Asia likes and uses.(00:32:00) - Rocks vs. OKRs: what's the difference and when does it matter?(00:39:15) - SOPs vs. “The Way”: document your processes, whatever you call them.(00:42:15) - When are core values useful and when are they just performative?(00:52:00) - Picking and choosing from EOS: take what works, leave the rest.
Neste episódio do Love the Problem, Flor e a especialista em OKR Rafaela Fonseca exploram os desafios e as melhores práticas na implementação de OKRs (Objectives and Key Results) nas organizações. A conversa aborda a frustração comum de ter um excesso de OKRs e a importância de manter o foco. É crucial entender que um "setup" bem feito – que envolve a clareza da estratégia, das prioridades e dos dados – é fundamental antes da escrita dos OKRs, um passo muitas vezes negligenciado na literatura sobre o tema. O episódio também destaca a disfunção do "OKR Batata", onde os OKRs não ganham vida própria sem o acompanhamento recorrente, enfatizando que os "check-ins" são o "coração do OKR". Discute-se a participação nos check-ins, a importância da comunicação e do vocabulário adequados para o engajamento, o papel essencial da liderança no suporte à autonomia e à execução da estratégia, e a necessidade de não perder o movimento em busca da melhoria contínua.Solta o Play!
Unlock the secrets to aligning your team's initiatives with real business value! In this video, we break down the art of translating high-level OKRs (Objectives and Key Results) into actionable strategies that truly move the needle. Discover the four essential value buckets every organization should focus on—increasing revenue, protecting revenue, reducing costs, and avoiding future costs. With practical examples and clear frameworks, you'll learn how to categorize your initiatives, justify their impact, and drive meaningful results for your business. Perfect for product managers, team leads, and anyone looking to make their work count!Chapters 00:00 Introduction: The Challenge of Aligning OKRs 01:49 Understanding Business Value: The Four Value Buckets 02:54 Value Bucket 1 04:44 Strategies for Value Bucket 1 07:05 Value Bucket 2 08:13 Strategies for Value Bucket 2 11:05 Value Bucket 3 12:47 Strategies for Value Bucket 3 14:13 Value Bucket 4 15:46 Strategies for Value Bucket 4 17:31 Recap: Applying the Value Buckets 18:11 Closing Thoughts & Next StepsWHO AM I?
In this episode, Aydin sits down with Greg Shove, CEO of Section, to unpack how AI isn't just a productivity tool—it's a new cognitive layer for modern organizations. Greg shares how Section pivoted from executive education to AI enablement after a single eye-opening session with ChatGPT. He dives deep into what it really takes to embed AI into workflows, culture, and decision-making—and why “talking to AI” is now mandatory at his company. From building a company-wide second brain with Claude to simulating board meetings with GPT, Greg offers a masterclass in practical AI integration.Timestamps:1:35 – Greg's background: from flameouts to $250M in exits2:00 – Section's pivot from exec ed to AI enablement3:01 – The 6-month internal resistance to AI4:50 – Why training isn't enough: the real AI challenge is change management6:07 – Why treating AI like regular software is a strategic mistake8:26 – What successful AI deployments have in common10:02 – Lessons from Shopify, Duolingo, and Fiverr on AI expectations11:45 – The price of AI is too low—why that might change14:03 – AI vs. analyst time: “an hour becomes a minute”15:31 – Section's 25% productivity gain with AI18:58 – Measuring productivity impact without perfect data21:24 – Clever metrics: output per headcount, OKRs, AI shoutouts24:51 – Using Claude as a company “second brain”26:11 – Greg's AI desktop setup: Perplexity, GPT, Claude27:43 – The Section Expert: maintaining company context for AI29:27 – “Working with Greg” manual: how to humanize your AI input31:00 – The difference between values and operating principles34:42 – Roleplaying board members with AI before real board meetings36:05 – Claude vs. ChatGPT vs. humans: who gave better board insights?41:00 – AI for owner-operators: create your own board42:26 – What Greg's most excited about: how AI unlocks new opportunities44:08 – Where to find Greg & Section + listener discountTools & Technologies Mentioned:Claude (Anthropic): Used to build a company-wide second brain and simulate board member personasGPT (OpenAI): Used as a daily thought partner and board advisorPerplexity: A go-to AI for fast, accurate information lookupsSection Expert (Claude project): A centralized AI project workspace housing all of Section's key documents for brainstormingProfAI (Section's product): An AI-powered coach designed to teach people how to use AI effectivelyChatGPT for Teams: Mentioned as a better, paid alternative to free-tier toolsGemini Pro: Noted for its screen-sharing and future context-awareness potentialCopilot (Microsoft): One of several LLM tools tested during board simulationsSubscribe at thisnewway.com to get the step-by-step playbooks, tools, and workflows.
I'm experimenting with Substack's Video feature. I'm not sure how this will look, appear, or even sound, but giving it a go. Below I include an outline of the video:Outline1. The Familiar Cascade* Many organizations use a hierarchical model: Pillars → Priorities → Initiatives → Epics → Tasks* Timeframes are often assigned at each level (e.g., 3–5 years at the top, sprints at the bottom)* Roles and ownership are mapped accordingly, from executive leadership down to product teams* These models persist because they're intuitive, visual, and create a sense of order2. Core Limitations of the Pyramid* Assumes one-way flow of informationThe model suggests strategy flows down, but in reality, critical insights flow up from teams engaging with customers and the market* Outcomes are often missing or impliedThere's no explicit representation of impact or results, even though that's what ultimately matters* Ignores time-to-impact variabilitySome tasks can generate impact in a week; some initiatives take years. The model fails to show these lags and feedback loops* Pushes teams into execution rolesAs you move down the pyramid, the framing becomes increasingly prescriptive. Teams are expected to deliver “work” without clear problem framing or strategic ownership* Misrepresents the scope and nature of workHigh-impact short-term efforts may not “fit” in the hierarchy, creating friction. It also disincentivizes small, iterative wins3. Temporal Scope and Organizational Culture* Comparing two fictional organizations reveals differences:* Org A's goals are outcome-driven across time horizons (e.g., 1–3 month engagement goals, 3–5 year market positioning)* Org B's goals are more output-focused and vague at longer horizons* Ownership of goals varies by company—some give product teams ownership up to the one-to-three quarter range, others do not* The same pyramid diagram can reflect entirely different behaviors depending on definitions, ownership, and cultural orientation toward outcomes vs. activity4. The Need for Multiple Lenses* The pyramid presents a single, strategy-to-task lens, but organizations operate with multiple overlapping views:* Outcome lens – focused on impact and customer results* Work lens – focused on deliverables and execution* Finance lens – focused on costs, forecasting, and ROI* Structure lens – focused on organizational shifts, team structure, and ownership* Each lens has its own rhythm, scope, and patterns of change* These lenses intersect in complex ways that a static pyramid cannot represent5. Real Work Behaves More Like a Fabric Than a Cascade* Work, strategy, and feedback move in all directions—not just top-down* Many artifacts and processes exist at mid-levels of abstraction, not neatly tiered* A more accurate model is a fabric or network of interconnected items with varying temporal scopes and ownership* Strategic influence can originate anywhere, and changes at any level can ripple across the system6. Introducing Artifact Types and Their CadenceTo support this networked reality, artifacts should be understood in terms of their nature and rhythm:* Anchor Artifacts* Have a defined time horizon (e.g., a 12-month roadmap)* Refreshed on a set cadence (e.g., quarterly planning cycles)* Useful for stability and coordination* Intent Artifacts* Represent bets, goals, OKRs, and strategic initiatives* Tend to evolve as work progresses and understanding deepens* Often nested or linked to other artifacts dynamically* Context Artifacts* Reflect shifting knowledge and environmental signals* Can be volatile (e.g., customer feedback) or stable (e.g., competitive analysis)* Drive updates to other artifact types when significant changes occur7. The Role of Rituals* Artifacts don't stand alone—they are reinforced and refreshed through team and organizational rituals* Effective operating systems clarify:* Which artifacts exist* Who owns them* When and how they are updated* How they relate to each other across different lenses and timeframes* Rituals also provide the opportunity to resolve contradictions and adapt to change8. Final Synthesis* The strategy pyramid is a helpful storytelling tool, especially for presentations or executive alignment* But it is insufficient for designing actual operating models* Effective models recognize:* Multiple lenses (not just one)* Temporal and definitional complexity* The need for dynamic linkages, not static nesting* The interplay of strategy, execution, finance, structure, and learning* Building an effective system means embracing this complexity and supporting it with the right artifacts and rhythms—not oversimplifying it into a cascade Get full access to The Beautiful Mess at cutlefish.substack.com/subscribe
We're sure you've heard the acronym: OKRs - Objectives and Key Results. But somewhere along the way, the simplicity got lost in translation. In this episode, we ask: What if we stopped calling them OKRs altogether? Roger Longden, TBG Founder and Marc Applebaum PM2 OKR Consultant at PM2 discuss how goal-setting became over engineered, why rhythms matter more than rituals, and the power of intention over jargon. If you're over hearing acronym over acronym but love what OKRs are all about, or if you've ever wondered why your team's goals feel disconnected—this one's for you. Enjoy the episode!
CHANGE NOW oder später – der Podcast rund um Veränderung mit Frank Peters
OKRs helfen Teams, um ihre Ziele zu erreichen und sich Schritt für Schritt zu entwickeln und zu verbessern. Ich habe aus meiner Erfahrung mit OKRs die wesentlichen Erkenntnisse destilliert und genutzt, um meine Ziele für das nächste Quartal mit mehr Motivation anzugehen. Und ein Beispiel, wie sich OKRs nutzen lassen, um Teammeetings effizienter zu machen, gibt es noch dazu.
digital kompakt | Business & Digitalisierung von Startup bis Corporate
In einem inspirierenden Gespräch mit Joel Kaczmarek enthüllt Tobias Haubert, Agile Coach bei Signal Iduna, die faszinierende Reise der Einführung von OKRs in einem etablierten Unternehmen. Tobias teilt seine Erfahrungen und gibt wertvolle Einblicke, wie man in einem großen Konzern agile Methoden erfolgreich implementiert. Von den Herausforderungen bis zu den Erfolgen – Tobias zeigt, wie gesunder Pragmatismus und eine klare Kommunikation den Weg zu mehr Effizienz und Transparenz ebnen. Ein Muss für alle, die Transformation hautnah erleben möchten! Du erfährst... …wie Tobias Haubert OKRs bei Signal Iduna erfolgreich einführte …welche Rolle gesunder Pragmatismus bei der Implementierung spielt …wie OKRs die Kommunikation und Transparenz im Unternehmen stärken …warum individuelle Anpassungen der OKR-Methodik entscheidend sind …welche Herausforderungen und Erfolge Signal Iduna mit OKRs erlebte __________________________ ||||| PERSONEN |||||
Judy Weber is a serial entrepreneur and business expansion expert helping women grow confidence and incorporate proven business strategies for scale while building on a foundation of faith. A former trial lawyer who has built businesses across marketing, real estate and interior design, Judy teaches her clients to think and win like a courtroom dynamo, integrating her legal experience with her faith-fueled approach to entrepreneurship. Host of the long running, globally ranked Bold Business Bold Faith podcast, Judy's mission is to normalize miraculous results for Christian women in business, emphasizing that success is inevitable when one operates from a place of calm, confidence, and certainty. She serves service-based businesses with coaching and the “Miraculous Mastermind” to master scaling.
Asia just hit her 90th day as fractional CMO with a new company, and in this episode of the In Demand Podcast, she shares everything she's taking away from those first three months. This episode is a behind-the-scenes look at how a marketing leader gets up to speed, creates clarity, and shapes outcomes. Asia and Kim cover everything from digging through legacy docs to building team structure and launching new systems. Got a question you'd like Asia to unpack on the podcast? Record a voicemail here. Links: DemandMaven OfferingTree Chapters (00:01:40) - What Asia focused on first: people, processes, tools, data.(00:07:30) - Identifying mission-critical gaps.(00:10:00) - Once you identify the gaps, you can start to find new opportunities.(00:12:55) - The first two artifacts that Asia created: CMO's Mandate, and a marketing strategy for the rest of the year.(00:17:15) - Month two: hiring new talent, refining workstreams, aligning on OKRs.(00:19:55) - Forecasting vs. budgeting vs. planning.(00:26:45) - Translating CAC and trial goals into action.(00:32:05) - Month three: getting executors executing .(00:35:00) - Relationship-building with product and sales.(00:36:30) - What comes next: aligning the ships, creating momentum, and scaling what works.
What happens when you give every employee access to the paid version of ChatGPT? At Knownwell, it wasn't just a tech decision—it was a culture shift. Knownwell CMO Courtney Baker, CEO David DeWolf, and Chief Product & Technology Officer Mohan Rao explore the real-world implications of a strategic move: providing company-wide access to ChatGPT. They share what sparked the decision and how a structured rollout strategy transformed productivity, communication, and innovation across the team. They also dive into what smart deployment looks like, from setting enterprise controls to embedding AI within your company's OKRs. Pete Buer kicks off the episode with an eye-opening look at Apple's latest research into large language model reasoning and why businesses must approach AI tools with both optimism and caution. He unpacks the importance of human-AI collaboration and encourages leaders to ditch the “magic wand” mindset. Also in this episode: Part two of Pete's interview with Ardy Tripathy, AI lead at OpsCanvas. Ardy reveals how AI can help eliminate “zombie resources” in cloud infrastructure, streamline CI/CD pipelines, and enhance visibility across systems. He also offers practical tips for CEOs on how to lead AI experimentation without losing control. This episode is a must-listen for leaders navigating the AI learning curve, and for teams wondering what enterprise-wide access really unlocks. Watch this episode on YouTube: https://youtu.be/NneA_LgHEYc Curious what your company's data looks like on Knownwell? Schedule a demo at www.knownwell.com.
Guest: Jhana LiCompany: Spyglass OpsPlatforms:
Smart Agency Masterclass with Jason Swenk: Podcast for Digital Marketing Agencies
Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training Have you ever found yourself grinding endlessly, only to pause and think, “Is this really what I signed up for?” Maybe you started your business chasing freedom—only to end up feeling trapped by the very thing you built. It's a common trap: the belief that working harder and enduring more pressure will eventually earn you the right to enjoy life after a big exit. But as today's guest discovered, you don't need to wait 10 more years to start living. What you really need is a clearer why, a stronger structure, and the right people around you—people who understand your vision and support your growth. Blake Denman is the president and founder of Rickety Roo, a remote agency specializing in SEO and paid search marketing. He'll discuss his unconventional path into entrepreneurship, which was influenced by a personal injury, and the importance of designing your business and life around personal values, not just growth for growth's sake. He also shares his time management strategies, how he uses AI for self-reflection, and his perspective on the mental load of entrepreneurship. If you're an agency owner still doing everything—from ops to admin to taxes—you'll relate to his story. In this episode, we'll discuss: Strategic hires that might results in your identity crisis. Designing your life before it designs you. Time audits, energy filters & the “$5K task” rule. Figuring out what you actually want. Do you thrive in chaos? Manufacture some healthy pressure. Subscribe Apple | Spotify | iHeart Radio Sponsors and Resources Wix: Today's episode of the Smart Agency Masterclass is sponsored by Wix Studio, the all-in-one platform designed to help agencies scale without the headaches. With intuitive tools, robust native business solutions, and low maintenance, Wix Studio lets your team focus on what matters most—delivering exceptional value to your clients. Ready to take your agency to the next level? Visit wix.com/studio and discover how Wix Studio can transform your workflow, boost profits, and strengthen client relationships. The Moment that Forced Him to Slow Down Blake didn't set out to build an agency. Like a lot of agency owners, he fell into it. What started as freelancing to pay the bills while he finished school and pursued a different career path took a hard left turn—literally—when a serious bike accident landed him with a traumatic brain injury. That moment forced Blake to slow down. Rebuild. Rethink. And when he got back into client work, he realized something: just because you can do it all doesn't mean you should. Like many agency owners, he hit the familiar ceiling of capacity. So he started hiring. First contractors. Then a coach in 2019. That's when the game really changed. The Pivot Point: Strategic Hires (and the Identity Crisis That Follows) When you've built your agency from the ground up, letting go isn't just hard—it can mess with your head. One of the pivots that really made a difference in Blake's agency was the strategic hires that required him to let go of some areas of the business. For instance, when he finally handed over operations. “I was like that John Travolta meme—just looking around wondering what to do with myself.” And that's the truth no one talks about: letting go of operations isn't just a tactical decision. It's emotional. You've tied your identity to being the guy who does everything. And suddenly… you're not. That shift sparked something deeper—what Blake calls “identity paralysis.” Not a crisis, but a freeze. A moment of, “If I'm not the operator, who am I now?” Spoiler: that question is the start of real CEO-level growth. Designing Your Life (Before It Designs You) Most agency owners plan every quarter like a military op: KPIs, OKRs, revenue targets. But how many plan their life that way? Blake started mapping his ideal year: the trips, the purchases, the experiences. Then he calculated what income he actually needed to live that life. We're mostly led to believe those goals are too far away, but the first time he did this he was just $1,500/month off. So many agency owners think they need to sell their business to finally live the life they want. But often, you don't need to sell—you just need to restructure. What if the business could serve your life now instead of being the thing you have to escape? Time Audits, Energy Filters & the “$5K Task” Rule Most people say they value their time but let it slip through their fingers, which is why you need a time tracking method that works for you. After trying a few, Blake got a framework from one of his early coaches. He categorizes his weekly tasks into four buckets: $5, $50, $500, and $5,000/hour value. If you think your time is worth $5,000 but the time audit shows its mostly spent in the $5 or $50 buckets, congrats—you've just diagnosed why your growth is stuck and your energy's tanked. To his surprise, this is what happened to Blake, who was spending way more time than he thought on the $5 and $50 columns. You don't scale by doing more. You scale by doing less of the wrong things. What Do You Actually Want? If your agency isn't giving you time, freedom, and joy… what the hell are you building it for? Blake now runs his agency with zero calls on Mondays. Focus time is blocked. The calendar is color-coded. And most importantly, the business doesn't need him 60 hours a week to grow. He also has the whole team on Brain.fm, a tool that uses science-backed audio to get you in the zone faster. Some would call that a lifestyle business, but so what? Lifestyle business can be extremely profitable too. Why not build your business around what you like and don't like? People who struggle for 20 years to then sell their agency find that after all their work they have maybe ten years left to do the things they want to do. Lessons for the Owner-Operator Ready to Evolve If you're reading this and feeling that twinge—that mix of burnout and “I want more” clarity—take these cues from Blake: -Let go of the identity that your agency is you. -Map your ideal life, then build your business to fund it. -Hire for elevation, not just delegation. -Your value isn't in the tasks you do. It's in the vision you hold. From the Hustle Hamster Wheel to the Hedonic Treadmill You want the 8-figure agency, right? So did Blake. Until he realized that every time he hit a new goal, he'd feel good for a week… maybe five days. Then it was back to baseline. This is what's called the Hedonic Treadmill—and agency owners live on it without realizing it. We chase growth for growth's sake. Or worse, for external validation—from peers, clients, even family. Blake stopped to think about what was next after he had the money. Was he supposed to save it? Spend it? Did he even need that much? Define what you want your life to look like, and build your agency to support that. Don't fall into the trap of chasing growth for validation more than for yourself. If you let go of the idea of just hitting a number, surround yourself with the best team and clients, and set your priorities, you'll be able to go after what you really want and live your best life. Agency Owners & the Calm in the Chaos Most agency owners have had the type of upbringing that's them great under pressure. Calm in chaos. Laser-focused when everything's on fire. Of course, this can also become a trap if you start creating chaos just to feel normal. For instance, you may seek pressure to push you into action. In his case, after years of needing the chaos, Blake turned to Claude to figure out a way to manufacture chaos without the disastrous consequences. His AI coach creates a “painful penalty” for missing a goal. For instance, donate $1,000 to a political group you can't stand if you miss a revenue target. That'll light a fire. Point is: for some people motivation isn't just about dreaming big. If you need some added pressure to get working engineer consequences that make staying small more painful than pushing forward. Do You Want to Transform Your Agency from a Liability to an Asset? Looking to dig deeper into your agency's potential? Check out our Agency Blueprint. Designed for agency owners like you, our Agency Blueprint helps you uncover growth opportunities, tackle obstacles, and craft a customized blueprint for your agency's success.
Are you still thinking of your team as family? In today's competitive market, that mindset could be costing you more than you realise. In this powerful episode of Online Marketing For Doctors TV & Podcast, we reveal why building a team of A-Players is essential to scaling your clinic and avoiding costly bottlenecks.
Frieda Möcker, Head of People & Culture at Sastrify, joined us on The Modern People Leader. We talked about the first steps she took to treat HR more like a product, how her team does sprint planning, and why she prefers “NCTs” over OKRs.---- Sponsor Links:
In this episode, Abi Noda speaks with Gilad Turbahn, Head of Developer Productivity, and Amy Yuan, Director of Engineering at Snowflake, about how their team builds and sustains operational excellence. They break down the practices and principles that guide their work—from creating two-way communication channels to treating engineers as customers. The conversation explores how Snowflake fosters trust, uses feedback loops to shape priorities, and maintains alignment through thoughtful planning. You'll also hear how they engage with teams across the org, convert detractors, and use Customer Advisory Boards to bring voices from across the company into the decision-making process.Where to find Amy Yuan: • LinkedIn: https://www.linkedin.com/in/amy-yuan-a8ba783/Where to find Gilad Turbahn:• LinkedIn: https://www.linkedin.com/in/giladturbahn/Where to find Abi Noda:• LinkedIn: https://www.linkedin.com/in/abinoda In this episode, we cover:(00:00) Intro: an overview of operational excellence(04:13) Obstacles to executing with operational excellence(05:51) An overview of the Snowflake playbook for operational excellence(08:25) Who does the work of reaching out to customers(09:06) The importance of customer engagement(10:19) How Snowflake does customer engagement (14:13) The types of feedback received and the two camps (supporters and detractors)(16:55) How to influence detractors and how detractors actually help (18:27) Using insiders as messengers(22:48) An overview of Snowflake's customer advisory board(26:10) The importance of meeting in person (learnings from Warsaw and Berlin office visits)(28:08) Managing up(30:07) How planning is done at Snowflake(36:25) Setting targets for OKRs, and Snowflake's philosophy on metrics (39:22) The annual plan and how it's shared Referenced:CTO buy-in, measuring sentiment, and customer focusSnowflakeBenoit Dageville - Snowflake Computing | LinkedInThierry Cruanes - Snowflake Computing | LinkedIn
This week's guest is Philipp Schett. Ron and Philipp discussed OKRs, accountability, making structural changes, balancing transparency and autonomy, and more. An MP3 audio version of this episode is available for download here. In this episode you'll learn: The quotes Philipp likes (2:02) What accountability looks like (6:52) About OKRs (10:23) How it could be beneficial in accountability (11:48) The structural changes they've made that have made an impact (17:58) Incorporating accountability whilst preventing surveillance culture (22:55) Balancing transparency and autonomy (28:35) Philipp's parting thoughts (31:22) Podcast Resources Right Click to Download this Podcast as an MP3 Philipp on LinkedIn Get All the Latest News from Gemba Academy Our newsletter is a great way to receive updates on new courses, blog posts, and more. Sign up here. What Do You Think? Have you ever used OKRs?
What is the Objectives & Key Results (OKR) framework? Why is the measurement and transparency of operating results so important to organizational health? How does the adoption of the OKR framework help make achieving balance between trust and accountability more achievable? To help answer these questions, we have Phillipp Schett joining us today on the Balancing Act Podcast. Phillipp is the founder and CEO of Wave Nine – a strategy execution consultancy focused on helping companies get the most out of the OKR framework. Tune into episode 198 to hear Phillipp's story, his career rocket-booster moment, and his thoughts on the use of OKRs to improve organizational trust and accountability. To learn more about Phillipp Schett, visit: https://wavenine.com/ To learn more about Andrew Temte, visit: https://www.andrewtemte.com
If you work for a software company, odds are that people make up 80-90% of your business's costs. Today's guest argues that in order to effectively manage a company's greatest asset, the CFO should be heavily involved in shaping the company culture. Bill Tole is the CFO of TrustRadius, a trusted platform where tech buyers find real reviews. He is skilled in creating structures around ambition and breaks down how TrustRadius creates and implements Objectives and Key Results (OKRs). He explains how they differ from KPIs, why they fail, and how to set aggressive but achievable goals. He discusses the Rule of 40 and why it's essential for the rest of the company to understand it. Bill also shares how CFOs can influence culture from a finance perspective and why a lack of failure is a cause for concern.—LINKS:Bill Tole on LinkedIn: https://www.linkedin.com/in/bill-tole-0a99789/TrustRadius: https://www.trustradius.com/15Five: https://www.15five.com/CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: http://mostlymetrics.comRELATED EPISODES:Less but Better: Miro's Justin Coulombe on the Power of Strategic Divestment in SaaS: —TIMESTAMPS:(00:00) Preview and Intro(02:15) Sponsor – NetSuite | Planful | Tabs(06:00) TrustRadius's Business Model(09:20) OKRs at TrustRadius and Finance's Role in Them(14:07) Finance's Role in Asking the Stupid Questions(15:58) Sponsor – Rippling Spend | Pulley | Navan(20:10) How To Set Aggressive but Achievable Goals(23:19) The Ideal Number of OKRs(24:21) Leaving Room for Failing or Innovating(25:57) OKR Derivatives at Department Level(27:36) Why OKRs Fail(28:55) Rewriting or Killing Off an OKR Mid-Way(29:51) Where To Track Your OKRs(32:03) Applying the Rule of 40(34:39) Educating the Org on the Rule of 40(37:34) EBITDA Versus Free Cash Flow for Calculating Rule of 40(39:24) The CFO As the Culture Leader(43:21) Using Money To Change the Culture in a Positive Way(45:42) Mistakes CFO's Make When It Comes to Culture(47:06) Long-Ass Lightning Round: Why Failure Is Okay(51:41) Advice to Younger Self(53:44) Finance Software Stack(55:12) The State of SaaS Fragmentation or SaaS Sprawl(57:28) Craziest Expense Story—SPONSORS:NetSuite is an AI-powered business management suite, encompassing ERP/Financials, CRM, and ecommerce for more than 41,000 customers. If you're looking for an ERP, head to https://netsuite.com/metrics and get the CFO's Guide to AI and Machine Learning.Planful's financial planning software can transform your FP&A function. Built for speed, accuracy, and confidence, you'll be planning your way to success and have time left over to actually put it to work. Find out more at www.planful.com/metrics.Tabs is a platform that brings all of your revenue-facing data and workflows - billing, AR, payments, rev rec, and reporting - onto a single system so you can automate and be more flexible. Find out more at: tabs.inc/metrics.Rippling Spend is a spend management software that gives you complete visibility and automated policy controls across every type of spend, saving you time and money. Get a demo to see how much time your org would save at rippling.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: pulley.com/mostlymetrics.Navan is the all-in-one travel and expense solution that helps finance teams streamline reconciliation, enforce policies automatically, and gain real-time visibility. It connects to your existing cards and makes closing the books faster and smarter. Visit navan.com/Runthenumbers for your demo.#failure #companyculture #OKR #KPI #Ruleof40 Get full access to Mostly metrics at www.mostlymetrics.com/subscribe
In this episode, we dive into the art of solving complex challenges with Hunter S. Gaylor—executive partner, financial strategist, and best-selling author. With an impressive career that spans mobile banking, corporate strategy, private aviation, and global diplomacy, Hunter is a business leader who's shaped industries. He is the founder of Spencer Pruitt, a graduate of Harvard University, and the author of Planes Plants and Politics: A Mental Framework To Help Overcome Challenges in Any Industry. Press play to discover: The biggest mistake that destroys more strategies than any other. Why clarity of purpose is the foundation of success in any project. The critical link between discipline, action, and results. The key factors that fuel ambition and drive toward achieving your goals. Uncover the powerful strategies behind Hunter S. Gaylor's proven methods that help businesses thrive—don't miss this insightful conversation! Follow Hunter on X @HunterGaylor and LinkedIn
According to The Times, employees now face an average of nine organizational changes per year, up from two before 2020, leading to increased change fatigue. So, how can you lead a change management strategy to help reps effectively navigate these changes?Shawnna Sumaoang: Hi, and welcome to the Win-Win podcast. I’m your host, Shawnna Sumaoang. Join us as we dive into changing trends in the workplace and how to navigate them successfully. Here to discuss this topic is Sobia Younus, the senior manager of sales learning and enablement at ApplyBoard. Thank you for joining us, Sobia. I’d love for you to tell us about yourself, your background, and your role. Sobia Younus: Sure. I really appreciate this opportunity. So I’m leading the sales learning and enablement team at ApplyBoard, a leading ed-tech platform that’s reshaping how international students access global education. So I lead a global sales enablement framework that focuses on performance process and people and my role. Spans everything from onboarding and ever boarding to performance improvement initiatives that firsthand impact the revenue. But to rewind a bit, my journey has never been linear, and I believe that’s been my strength. So while I’ve always been rooted in international education, my niche has always been B2B and B2C sales, and that helped me build a strong understanding of client behavior, market trends, and grow through meaningful engagements. I have been with ApplyBoard for almost six years. I initially joined the CX team, which gave me insight into the student journey and operations side of how applications are being processed. From there, I transitioned into the sales role where I gained the firsthand experience of navigating the field. Finally in 2021, I moved into sales enablement, and that’s where everything came together. It blended my passion for education, my CX foundation, and my love for sales performance into one purpose driven role. I think today I focus more on building scalable strategic enablement programs that build and drive revenue, empower people, and connect the dots between learning, growth and results. Personally, to me, and I really wanna share that, I believe that for me, enablement is where storytelling meets the strategy. That’s what make it so exciting, and what excites me the most about my work today is the blend of strategy and human behavior. Most importantly, understanding how people learn, they stay motivated, and how the right tool and messaging can turn a sales team into a high performing empowered force. That’s why I’m so excited to be here today because platforms like Highspot make a real difference. SS: Amazing. Well, we’re excited to have you here, and given your extensive experience in education management, I’d love to learn from you what are some of the unique challenges that reps in the industry face, and how can enablement help them navigate these challenges? SY: So that’s a very important subject. So one of the most unique aspects of international education industry is how deeply it influenced by external elements like immigration reforms, global mobility trends, and even geopolitical shifts. So unlike other industries where salespeople can rely on relatively stable products or markets, education is often at the mercy of forces beyond control. And as a result, salespeople in this space aren’t just selling a service. They’re actually navigating constant change, managing expectations, and often having to realign their strategy in real time. And a great example is what recently we saw last year, the government introduced caps on your international student permits and tightened eligibility for post-graduation work. Permits. So these changes had an immediate impact on student demand, also program selection and school preferences. So practically overnight, our sales rep has to understand the implications, shift focus away from programs that no longer align with student goals and reposition alternatives that still offered strong appeal to students. This is where enablement became mission critical. And an apply board. We don’t just see enablement as a static function. It is a real time strategic engine that basically supports business agility. So within days of those updates, our team not only delivered the sessions, so we created and rolled out sales plays and updated talk tracks and Highspot. We designed objection handling strategies on Highspot to help our. Salespeople reposition options with clarity and assurance. So in short, we didn’t just inform, we equipped, so that is important. Our goal was to turn uncertainty into clarity so that salespeople could keep on building trust and drive impact through their communication. And I believe that enablement also reinforces a culture of agility. So in industries like ours, change is inevitable. But when enablement is done right. It actually becomes a competitive advantage. SS: Amazing. And I know that at ApplyBoard, you actually switched off a previous enablement platform and moved to Highspot. What motivated you to reevaluate and change your enablement tech stack? SY: So when we initially built our enablement infrastructure at Apply board. Our primary focus was on structured learning. So naturally our, you know, tech stack leaned towards a traditional LMS. It served its objective at that time, like building, onboarding courses and track completion. But as our sales organization matured. So did the scope of our needs. So we realized that enablement couldn’t just live in siloed training modules. It had to be integrated into the daily flow of work. And our sales team needed not just learning, but relevant and up to date resources and real time support to navigate, you know, fast-paced industry changes. So in short, we needed more than an LMS. We needed a true enablement platform that could function as a CMS, a single source of truth, and I would love to call Highspot a strategic one-stop shop. So that’s what motivated our ship to Highspot. We wanted a one-stop solution where onboarding and ever boarding training and sales plays and competitive insights all could live together. A platform that doesn’t just share knowledge, but it gives. To our salespeople when they need it in a way that fits how they work. So it was a mindset shift from how do we train people to how we enable performance? And Highspot gave us the ash to just do that. SS: Change management is absolutely crucial, especially during major product or policy updates. What are some of the common pitfalls that organizations can face during change and how can they avoid them? SY: It’s a very crucial issue, and it is often underestimated and not because organizations don’t recognize its importance, but because they assume communication alone is enough. One of the most typical pitfalls is treating change as an announcement rather than a proper process. So when major product updates or you know, changes happen, especially in the industry like international education where external shifts can be sudden and high stake, simply informing teams isn’t enough. You need to enable them. So, and other pitfall that I wanna mention over here is failing to connect the why behind the change. So, if sales reps or CX teams don’t understand how an update or change a product shift ties back to their goals or the client’s goals. It usually creates resistance. Or worse disengagement. So change without clarity leads to confusion. And I always believe that change without a proper plan leads to chaos. So one more typical misstep that I wanna mention over here is not planning for reinforcement. So even when the rollout goes smoothly, but without a continuous enablement, like quick one pages or talk tracks, or life scenarios and sales place, trust me, all behavior will return. People default to what they know when things get tough, you know? But at ApplyBoard, we’ve learned this through the hard way, that effective change management start with empathy and end spend with enablement. So we ensure teams understand the work, the why, and how of every change, and we don’t stop at emails. We provide field ready tools, align managers as change champions, and use platforms like Highspot to make resources easily accessible and track the engagement, which is very important. So we all know that change is inevitable, but chaos is optional and you can do wonders if you treat enablement as a bridge between strategy and execution. SS: In your opinion, what is the strategic advantage of an enablement platform when navigating change? SY: So, in my opinion, the strategic advantage of an enablement platform during especially the time of change, is simple. It turns information into action at scale and in real time. So change, especially in the fast moving industries like international education. Often creates a gap between what the business knows and what the field needs. So product evolves, policies, they change and market fluctuates. But if your sales teams can’t access the right information at the right moment, trust me, execution suffers. So this is where an enablement platform becomes mission critical. It just centralizes the word, the why and how of change into one cohesive experience. So instead of scattered emails, you know, outdated decks or reactive training sessions, you get a single source of truth, which is updated, which is searchable, relevant, and embedded in the daily workflow. I’m so glad to say that at Highspot has given us the ability to roll out updates with precision and speed, and when major changes hit, you know, like the recent PGWP reforms, we can respond with focus sales plays, updated talk tracks, training modules, and enablement briefs in one place. We are not just informing the salespeople, we are empowering them to act immediately with clarity, with the right message. So that’s the advantage of a strong enablement platform like Highspot, that it turns change into action. It aligns teams to keep a clear narrative, gives clear visibility into what’s working, also helping you execute with assurance and stay ahead. SS: And I know Plays have been a key lever in helping your reps navigate change, such as, you know, with a recent government policy update that impacted your go-to-market strategy, how did you leverage plays to support this initiative and, and ensure global team alignment? SY: So to be very honest, Sales Plays have become one of our most powerful tools for driving clarity during moments of change. A great example, as you said, and I mentioned earlier as well, the IRCC updates last year, that significantly impacted which programs and institutions were feasible for students creating a sudden shift in our go-to market approach as well. So we knew that without quick and organized actions, this could lead to inconsistent messaging, confusion in the field and you know, lost trust with our clients as well. So we leaned heavily on sales plays and Highspot to bring structure to the chaos. So first we worked cross-functionally with the product team CX and the market expert to streamline these changes into actionable insights. So we took it this way, so we help them understand what it meant. What was changing and how it impacted our clients and the students. Then we created some tailored sales place that included updated talk tracks to help salespeople position alternatives with with clarity and empathy and segmented school lists like highlighted eligible and ineligible programs, suggested outreach. Templates and objection handling approach. Also, we did some live enablement sessions to walk them through our strategy and create some space for q and a as well. But most importantly, next steps for the salespeople. And because the sales play lived in Highspot, we could monitor. The engagement, the usage, and the adoption globally. So this gave us clear visibility into where reinforcement was needed and allowed the regional leaders to support their teams more effectively. And honestly, in moments like these sales plays are a vehicle for alignment, clarity, and assurance. They help us go from reactive to proactive insurance. Our teams aren’t just informed, but they’re ready. SS: That’s impressive. And you also implemented a Learning Tuesday initiative to drive engagement, which has helped you achieve a remarkable 91% recurring usage in Highspot. Could you share more about this practice and, and how you’re driving adoption of the platform amongst your reps? SY: So one of the most important lessons that I have learned in my enablement journey is this. If you want to build a culture of learning, don’t push your salespeople, walk in their shoes. So understand their reality, their pressures, and how they spend their day and apply aboard are salespeople are constantly engaging with clients, pitching multiple destinations, helping clients navigate multiple schools and programs. So for them to be effective, clarity is everything. And it comes from knowing your product, your destination, your message by heart. And that insight shaped our approach to drive Highspot adoption as well. So instead of just treating enablement as a checklist, we focus on making learning relevant, timely, and useful. So that’s where Learning Tuesday was born. It’s a recurring initiative, you know, to share short, impactful learning that fits easily into the flow of the week. So each Tuesday we choose a specific focus area of our sales team, whether it’s like a destination or a school or a program or any product update and build a supporting asset and a quick quiz in Highspot to provide timely, practical resource that aligned with what salespeople are actively navigating in the field. So the goal was simple. Like make learning part of their workflow, not an interruption to it, you know? And it’s very important to understand. And because we use Highspot to highlight success stories across the teams. So this approach helped us reach a 91% recurring usage rate and Highspot, because salespeople weren’t being told to learn. They chose to learn and it was because the assets and focus areas were so relevant, timely, and help them, uh, do their jobs. And I believe that and its score that enablement isn’t just about sharing information. It is about supporting people by giving them the right tools and add the right time and helping them see the difference it makes SS: Again, impressive. And as a results driven leader, what are some of the key metrics that you track to effectively drive change initiatives? SY: That’s a great point. And you know, one that really reflects how enablement has evolved as a function, especially in ApplyBoard, so early in our en enablement journey. Like many other teams, we are primarily focused on the surface level metrics, like number of views and number of assets viewed, and or how often an asset was viewed. But we quickly realized those numbers can be misleading. For instance, if two people viewed three assets a hundred times, the view count may look impressive, but it doesn’t tell you anything about who’s engaging, how many people are engaging or whether it is actually driving behavioral change. So we took a step back and asked ourselves that, what does meaningful engagement look like? What actually signals that our enablement efforts are influencing performance. So that led us to create a more focused Highspot performance, you know, engagement framework, one that actually prioritizes impact over bulk. So we started tracking. Metrics that showed the full picture of how salespeople were using and applying enablement in their work. I will share some examples, like number of unique people viewing the assets, not just the total views, monthly and weekly hours spent on Highspot, both overall and segmented by the projects. Also, the completion rates of assessments and the onboarding courses. Especially tied to the onboarding milestones and also initiatives like Learning Tuesdays. Also, engagement with the sales players and the field tools, especially during the moments of change. And when I say engagement, I mean time spent on these assets and how many people viewed the assets, and most importantly, a correlation. Between Highspot engagement and sales OKRs, like win rates or ramp-up time. So this shift actually helped us move from reactive reporting to proactive decision making. So instead of just knowing what’s being clicked or now we understand what’s actually being used. What is actually being retained and you know, what is actually impacting their performance. So it has helped us improve our, you know, Highspot approach by removing the low performing resources and focusing more on what actually helps our salespeople in the field. And I believe that an enablement metrics shouldn’t just measure activity. They should measure momentum. And when you focus on the right ones, they become a powerful lever for driving lasting change. SS: Amazing. Well, Sobia, I’m hoping you can share with me. Since implementing Highspot, what business results have you achieved and do you have any wins you can share? SY: So many. I can gladly say that. So many wins since we started using Highspot. So many wins. So we have seen some clear improvements in key sales. Performance metrics that support our business goals. While many things can influence results like market changes or team growth, but enablement has played a very important role in keeping that progress going. Like I said earlier in international education and ed tech sector, things move fast. We are always dealing with changes, immigration updates, and new information, and at the same time, we are growing quickly and bringing in people from all sorts of industries. So some with sales experience, but little international education experience and knowledge and others with the opposite. So enablement helps bridge that gap early on. This mix actually led to longer ramp up times, like longer than typically 50 to 60 days. As a new hire, they were learning about both the product and the education sector. So you know, it was taking a lot of time for them to learn all of that. But by building a structure. Role specific onboarding program within Highspot. We changed the game, our onboarding program. Now delivers destination training, platform fluency, and process enablement all in one centralized, searchable space, high sport. So as a reserve, we’ve successfully brought ramp up time just under 30 days on average. So the acceleration has had a clear impact on early client engagement and revenue readiness. Highspot just didn’t, you know, help us organize the asset. It helped us succeed. Successfully execute onboarding, scale their learning across borders, and you know, prepare salespeople to thrive in one of the most dynamic industries out there. Also, I can say this with assurance that enablement helped translate change into action, and Highspot was the strategic engine that allowed us to do that with speeds, scale and clarity. SS: Last question. If you could share one crucial lesson learned from your experience supporting teens through change, what would it be? SY: So, one very crucial and important lesson that I’ve learned is that successful change isn’t about having all the answers. It’s about creating alignment, trust, and momentum. So I’ve seen that teams respond best when they understand the why. Feel heard in the how. Can see themselves in the what’s next? So change sticks when it’s not just implemented, but truly internalized. And you know, that’s where sales enablement plays a crucial role by equipping teams with the right messaging, timely training, and actionable resources to navigate change with clarity and assurance and platform like Highspot make that happen successfully at scale. SS: Sobia, again, thank you so much for joining us. I really appreciate your insights. SY: I really appreciate that you having me here. It’s a pleasure and I truly enjoyed sharing, you know, all of the experience and learning. SS: To our audience, thank you for listening to this episode of the Win-Win podcast. Be sure to tune in next time for more insights on how you can maximize enablement success with Highspot.
The OKR Trio is back with Part 2 of their brutally honest Q2 2025 forecast, and they're not holding back. Sara Lobkovich, Maria Rowcliffe, and Natalie Webb tackle the questions you've been asking about rigid vs. flexible OKR approaches, timing models that actually work, and trends we're seeing in tool choices.But here's where it gets spicy: they're sharing their most controversial OKR opinions, speed round style! From leaders trying to weaponize OKRs as surveillance tools to the popular (but problematic) advice to limit teams to just one strategic priority, this conversation will challenge norms you might not be able to imagine actually exist out there.You'll discover why monthly check-ins might mean you're tracking instead of managing, how geography is shaping OKR strategy differently across continents, and why Excel is making a surprising comeback in the enterprise. Plus, Sara drops a financial metrics hot take that might make your CFO squirm.This isn't your typical goal-setting advice. It's three veteran practitioners sharing what they're really seeing in the field, complete with the controversies, contradictions, and hard-won insights that only come from years in the trenches.Episode Highlights:Quarterly vs. Trimesterly Planning: why the Q4 “drop-off” is real—and how cadence choices impact OKR adoption across teamsBiweekly Reinforcement Loops: how one leadership team's consistent review rhythm is accelerating organization-wide buy-inTool Sprawl & Excel Resurgence: why many orgs are ditching premium OKR platforms for scrappier, process-first setupsWhen Tools Hurt More Than Help: the danger of letting project management tools define your key resultsHot Takes on OKRs: financial metrics don't belong in key results (and one-size-fits-all “just one OKR” advice? Hard pass)Big Brother OKRs?: pushing back when leadership wants to use OKRs for surveillance instead of strategyQ3 Preview: a deep dive on execution, achievement—and how to actually decide what OKR tooling makes sense for your orgKey Concepts Explored:Hybrid Localization ApproachesLeadership sets objectives, teams shape Key ResultsThemes as bridges when objectives don't translate locallyKRs and Sub-KRs for fast-moving Scrum teamsMoving away from rigid objective cascadingTiming Model EvolutionBiweekly check-ins integrated with Scrum cyclesThe discipline of at least twice-weekly KR managementQuarterly vs. trimester cycle trade-offsEvent-triggered OKR adjustments for volatile environmentsTool Integration StrategiesProcess-first, tool-second implementation approachExcel resurgence due to cost considerationsAvoiding dueling OKR and project management platformsRecognition that L1 and L2 math doesn't require specialty softwareControversial Practices and Hot TakesOKRs as surveillance tools (problematic)Arbitrary "one OKR only" mandates (counterproductive)Financial metrics as KPIs vs. Key Results (contentious)Project deliverables masquerading as OKRs (misleading)Notable Quotes: "If you have a KR that you only manage monthly, you are not managing it, you're tracking it. Because you essentially have two data points, and then the quarter is over." — Maria Rowcliffe [00:06:00]"Once we learn the words and leadership is modeling the words and meanings, then the rigidity can come out of the framework." — Sara Lobkovich [00:04:00]"Financial metrics belong in mandatories and budgets. They're KPIs, they aren't key results." — Sara Lobkovich [00:15:00]"Bad news only gets worse with time. So the earlier they can
What does it take to lead a legacy brand into the digital future? Flick Collingwood chats with Nuno Miller, Digital COO at N Brown Group, to explore the company's bold transformation from mail-order giant to modern e-commerce player. Hear how N Brown is reshaping its culture, breaking down silos, and placing customer-centricity at the heart of its operations. ⏱ Timestamps: [00:00] N Brown's legacy: From catalog to digital [02:30] Why transformation is more than just technology [05:45] OKRs, mission drives & cross-functional tribes [09:30] Breaking silos & building customer-first teams [13:30] The critical role of CEO sponsorship [17:30] Lessons learned: mindset shifts & cultural change [21:00] Nuno's advice for leading successful digital transformations
As your nonprofit grows, your leadership style has to evolve — fast. In this episode, I share the mindset shifts and systems you need to lead effectively at scale without burning out or micromanaging. I break down the three key levers that help you trade control for clarity and oversight. You'll learn how to set up a "leadership cockpit" so you can stay focused on the big picture, trust your team, and stay aligned with your mission as complexity increases. This is one of the most common — and emotionally tricky — transitions nonprofit leaders face. I'll walk you through what it really looks like to lead when you're no longer touching every part of the work.What You'll Learn:How to replace control with high-level oversight as your team growsWhat to include in your leadership dashboard to stay focusedWhy aligning on operational values is key to scaling without chaosKey Takeaways:Leadership at scale is about narrowing your focus, not expanding it.Operational values must guide decisions across the team—even when you're not in the room.Dashboards, OKRs, and clear priorities help you lead strategically instead of reactively.The 3 Core Levers for Leading at a Higher Altitude:Decision-Making AlignmentEmbed clear operational values across every level of the orgDefine what “good” looks like in real behaviorDon't ask for post-decision updates — build alignment that leads to the right decisionsProgrammatic Oversight via OutcomesSet clear, narrow priorities everyone can articulateEstablish measurable team-wide and individual goalsUse OKRs to track progress without monitoring tasksInformation Flow That Serves the CEO RoleEliminate noise: don't attend every meeting or get every updateDesign meeting cadences and reports that elevate key signalsSurface risks, check for alignment, and trust your team to manage the detailsResource Mentioned: Delegation Ladder Want to work together? Apply for the Next Level Nonprofit Accelerator, a high-touch coaching and training accelerator for established organizations that want a smart, powerful playbook for taking their growing organization to the next level. Connect with me! LinkedIn Instagram YouTube
In this episode, John Waldmann, CEO of Homebase, shares how the 10-year-old SaaS company blew up its roadmap and rebuilt around AI—from culture to code. He walks us through the shift from 20-page PRDs to lightning-fast demos, reclaiming product leadership, and pushing teams into their “oh shit” moment with AI.We explore the leadership reckoning, cultural resistance, and practical playbook behind the transformation—and what it means for the future of SaaS, small businesses, and human-centered AI. If you're leading (or bracing for) an AI shift, this one's packed with hard-earned lessons and honest insight.Key Takeaways: You Can't Wait for Buy-In—Leadership Means Pushing the Shift — John didn't wait for excitement or alignment—he took back product leadership and forced the move toward AI. It wasn't about consensus, it was about momentum. If you're leading a team through this kind of shift, your job isn't to ask for permission—it's to create urgency before it's obvious.Speed Over Specs — Prototypes Are the New Strategy — Homebase moved from 20-page PRDs to live demos built in hours. That switch didn't just make shipping faster—it changed the way teams learn, think, and listen to customers. The takeaway? Stop planning in the abstract. Ship something real, now.Culture Is the Real AI Roadblock — The hardest part of going AI-first isn't tech—it's trust, fear, and inertia. From engineers to support teams, John had to help people reach their “oh shit” moment with AI. That's when change sticks. Until then, it's just optional homework. Leaders need to make adoption inevitable.AI Should Bring You Closer to Your Customers, Not Farther — This episode isn't about chasing shiny tools. It's about using AI to reduce the noise—so your team can focus more on humans, not less. For John, pragmatic AI is about freeing up time, getting closer to customer problems, and making the org feel smaller, not colder.LinkedIn: John Waldmann | LinkedInHomebase: All-in-one Employee Scheduling, Time Clocks, Payroll, & More | Homebase00:00 Introduction and Initial Reactions to AI00:31 Meet John Waldmann and the Story of Homebase00:53 Reinventing Homebase as an AI-First Company01:46 From PRDs to Prototypes: Building Faster, Learning Smarter05:02 How AI Is Reshaping the Customer Experience09:19 Culture Shock: Resistance, Skepticism, and AI Adoption14:03 The End of SaaS as We Know It?19:34 Leading Through Disruption: Ownership, Urgency, and Org Design25:12 Forcing the Shift: Getting Teams to Embrace AI27:50 Hiring the Unemployed—and Other Nontraditional Talent Bets28:56 Curiosity > Credentials: What to Look for in AI-Ready Teams31:57 New Expectations, OKRs, and Holding Teams Accountable37:10 Serving Small Businesses Better with AI44:52 Final Thoughts: Team Dynamics, Founder Risk, and What's Next
What does it really mean to have a bias toward action and how do you build that into your culture without skipping strategy? Boris Gloger joins Brian Milner for a deep dive on experimentation, leadership, and the difference between tactical work and true strategic thinking. Overview In this conversation, Brian welcomes longtime Scrum pioneer, consultant, and author Boris Gloger to explore the tension between planning and doing in Agile environments. Boris shares how a bias toward action isn’t about skipping steps—it’s about shortening the cycle between idea and feedback, especially when knowledge gaps or fear of mistakes create inertia. They unpack why experimentation is often misunderstood, what leaders get wrong about failure, and how AI, organizational habits, and strategy-as-practice are reshaping the future of Agile work. References and resources mentioned in the show: Boris Gloger LinkedIn Leaders Guide to Agile eBook Join the Agile Mentors Community Subscribe to the Agile Mentors Podcast Want to get involved? This show is designed for you, and we’d love your input. Enjoyed what you heard today? Please leave a rating and a review. It really helps, and we read every single one. Got an Agile subject you’d like us to discuss or a question that needs an answer? Share your thoughts with us at podcast@mountaingoatsoftware.com This episode’s presenters are: Brian Milner is SVP of coaching and training at Mountain Goat Software. He's passionate about making a difference in people's day-to-day work, influenced by his own experience of transitioning to Scrum and seeing improvements in work/life balance, honesty, respect, and the quality of work. Boris Gloger is a pioneering agile strategist and Germany’s first Certified Scrum Trainer, known for shaping how organizations across Europe approach transformation, strategy, and sustainable leadership. As founder of borisgloger consulting, he helps teams and executives navigate complexity—blending modern management, ethical innovation, and even AI—to make agility actually work in the real world. Auto-generated Transcript: Brian Milner (00:00) Welcome in Agile Mentors. We're back for another episode of the Agile Mentors Podcast. I'm with you as always, Brian Milner. And today I have the one, the only Mr. Boris Glogger with us. Welcome in Boris. Boris Gloger (00:11) Yeah, thank you, Eurobrein, for having me on your show. Brian Milner (00:14) Very excited to have Boris here. For those of you who haven't crossed paths with Boris, Boris has been involved in the Scrum movement, I would say, since the very, very earliest days. He's a CST, he's a coach, he's an author, he's a keynote speaker. He had a book early called The Agile Fixed Price. He runs his own consultancy in Europe. And he has a new book that's been, that's going to be coming out soon called strategy as practice. And that's one of the reasons we wanted to have Boris on is because there's kind of this topic area that's been percolating that I've heard people talk about quite often. And I see some confused looks when the, when the topic comes up, you hear this term about having a bias toward action. And, we just wanted to kind of dive into that a little bit about what that means to have a bias toward action. and really how we can apply that to what we do in our day-to-day lives. So let's start there, Boris. When you hear that term, having a bias toward action, what does that mean to you? Boris Gloger (01:12) The fun thing is I was always in tune with the idea because people said my basic mantra at the beginning of doing agile was doing as a way of thinking. So the basic idea of agile for me was always experimentation, trying things out, breaking rules, not for the sake of breaking rules, but making to create a new kind of order. the basic idea is like we had with test-driven development at the beginning of all these agile approaches and we said, yeah, we need to test first and then we have the end in our mind, but we don't know exactly how to achieve that. So there is this kind of bias towards action. That's absolutely true. On the other hand, what I've always found fascinating was that even the classical project management methodologies said, Yeah, you have to have a plan, but the second step is to revise that plan. And that was always this, do we plan planning and reality together? And actually for me at the beginning, 35 years ago, was exactly that kind of really cool blend of being able to have a great vision and people like Mike and all these guys, they had always said, we need to have that kind of a vision, we need to know. Yeah, if the product owner was exactly that idea, you have to have that vision, but you really need to get the nitty-gritty details of, so to say, of doing this stuff. Brian Milner (02:40) Yeah, that's awesome. And the thing that kind of always pops to my head when I think about this is, we hear this term bias toward action and there's sort of this balance, I think a little bit between planning and action, right? I mean, you wanna plan, you wanna plan well, but you don't wanna over plan. You don't wanna waste too much time trying to come up with a perfect plan. You wanna... you want to do things, but you also don't want to be, you don't want to rush into things. So how do people find that balance between not just, you know, going off, you know, like we say in the U S half cocked a little bit, you know, like just not, not really not ready to really do the thing that you're going to do. Cause you didn't really invest the time upfront, but on the other hand, not spending so much time that you're trying to get the perfect plan before you do anything. Boris Gloger (03:28) You know, the problem, for me, the issue was solved by when I figured out that the teams typically struggle not to achieve, for instance, the sprint goal or the end or whatever they wanted to accomplish when they have not the right know-how. So it's a knowledge problem. So for instance, I don't know if this is still the case, but sometimes developers say, need to... to immerse myself with that I need to figure that out. I need to get the new framework before I can do something about estimates or something. So whenever you hear that, that you know that person that just tries to give you an estimate or the team that would like to come into a sprint goal or whatever it is, they are not really knowing what topic is about. It's a knowledge gap. And then people tend to go into that analysis paralysis problem. They don't know exactly what they need to do. So therefore they need to investigate. But by doing investigation, you start making that big elephant in the corner, larger and larger and larger and larger because you go that ishikara diagram, you have too many options. It's like playing chess with all options at hand and not have enough experience. What kind of gambit you would like to do. So everything's possible and by, because you have not enough experience, you say everything's possible, that creates too much of a planning hassle. And Agile, is the funny thing is, made us very transparent by just saying, okay, let's spend maybe two weeks. And then we figured out two weeks is too much. So let's do a spike, then we call it a spike. The basic idea was always to have a very short time frame, timeline where we try to bring our know-how to a specific problem, try to solve it as fast as possible. And the funny thing was actually was, as if I I confess myself that I don't know everything, or anything, sorry, that I don't know anything, then I could say, I give me a very short timeline, I could say I spend an hour. And today we have chat, CVT and perplexity and all that stuff. And then we could say, okay, let's spend an hour observation, but then we need to come up with a better idea of what we are talking about. So we can shorten the time cycle. So whenever I experienced teams or even organizations, when they start getting that planning in place, we have a knowledge problem. And a typical that is, is, or the classical mindset always says, okay, then we need to plan more. We need to make that upfront work. For instance, we need to have backlogs and we need to know all these features, even if we don't know what kind of features our client really would like to have. And the actual software problem is saying, okay, let's get out with something that we can deliver. And then we get feedback. And if we understand that our kind of the amount of time we spend is as cheap as possible. So like we use the tools that we have. We used to know how that we have. We try to create something that we can achieve with what we can do already, then we can improve on that. And then we can figure out, we don't know exactly what we might need to have to do more research or ask another consultant or bring in friends from another team to help us with that. Brian Milner (06:46) It's, sounds like the there's a, there's a real, kind of focus then from, from what I'm hearing from you, like a real focus on experimentation and, you know, that, that phrase we hear a lot failing fast, that kind of thing. So how, do you cultivate that? How do you, how do you get the organization to buy in and your team to buy into that idea of. Let's experiment, let's fail fast. And, and, we'll learn more from, from doing that than just, you know, endlessly planning. Boris Gloger (07:12) I think the URCHAR community made a huge mistake of embracing this failure culture all the time. We always tell we need to call from failure because we are all ingrained in a culture in the Western society at least, where we learned through school our parents that making failures is not acceptable. Brian Milner (07:18) Ha ha. Boris Gloger (07:32) And I came across Amy Atkinson and she did a great book to make clear we need to talk about failures and mistakes in a very different kind of way. We need to understand that there are at least three kinds of mistakes that are possible. One is the basic mistake, like a spelling error or you have a context problem in a specific program that you write or you... You break something because you don't know exactly how strong your material is. That is basic mistake. You should know that. That's trainable. The other is the kind of error that you create because the problem you try to solve has too many variables. So that's a complicated problem. You can't foresee all aspects that might happen in future. So typical an airplane is crashing. So you have covered everything you know so far. But then there's some specific problem that nobody could foresee. That's a failure. But it's not something that you can foresee. You can't prevent that. You try to prevent as best as possible. And that's even not an accepted mistake because sometimes people die and you really would like to go against it. So that's the second kind of mistakes you don't like to have. We really like to get out of the system. And then there's a third way kind of mistakes. And that is exactly what we need to have. We need to embrace that experimentation and even experimentation. mean, I started physics in school and in university and an experimental physicists. He's not running an experiment like I just throw a ball around and then I figure out what happens. An experiment is a best guess. You have a theory behind it. You believe that what you deliver or that you try to find out is the best you try to do. The Wright brothers missed their first airplane. I mean, they didn't throw their airplane in the balloon. Then it gets destroyed. They tried whatever they believed is possible. But then you need to understand as a team, as an organization, we have never done this before, so it might get broken. We might learn. For instance, we had once a project where we worked with chemists 10 years ago to splice DNA. So we wanted to understand how DNA is written down in the DNA sequence analyzer. And I needed to understand that we had 90 scientists who created these chemicals to be able to that you can use that in that synthesizer to understand how our DNA is mapped out. And we first need to understand one sprint might get results that 99 of our experience will fail. But again, management said we need to be successful. Yeah, but what is the success in science? I mean, that you know this route of action is not working, right? And that is the kind of failure that we would like to have. And I believe our Agile community need to tell that much more to our clients. It's not like, we need to express failure. No, we don't need to embrace failure. We don't want to have mistakes and we don't want to have complicated issues that might lead to the destroying of our products. need on the other hand, the culture, the experimentation to figure out something that nobody knows so far is acceptable, it's necessary. And then, edge our processes help us again by saying, okay, we can shorten the frame, we can shorten the time frame so that we can create very small, tiny experiments so that in case we are mistaken, Not a big deal. That was the basic idea. Brian Milner (11:04) That's a great point. That's really a great point because you're right. It's not failure in general, right? There are certain kinds of failures that we definitely want to avoid, but there's failure as far as I run an experiment. at that point, that's where we start to enter into this dialogue of it's not really a failure at that point. If you run an experiment and it doesn't turn out the way you expected, it's just an experiment that didn't turn out the way you expected. Boris Gloger (11:30) Basically, every feature we create in software or even in hardware, we have never done it before. So the client or our customers can't use it so far because it's not there. So now we ship it to the client and then he or she might not really use it the way that we believe it is. Is it broken? it a mistake? It was not a mistake. It was an experiment and now we need to adapt on it. And if we can create a system, that was all that was agile, I think was a bot. On very first start, if we can create a system that gives us feedback early. then that guessing can't be so much deviation or say in a different way, our investment in time and material and costs and money and is shortened as much as possible. So we have very small investments. Brian Milner (12:13) Yeah, that's awesome. I'm kind of curious too, because, you know, we, we, we've talked a little bit at the beginning about how, you know, this is part of this bias towards action as part of this entrepreneurial kind of mindset. And I'm curious in your, experience and your consultants experience that you've worked with big companies and small companies, have you noticed a difference in sort of that bias toward action? Uh, you know, that, that kind of. is represented in a different way in a big company versus a more small startup company. Boris Gloger (12:48) The funny thing is I don't believe it's a problem of large corporations or small, tiny little startups, even if we would say that tiny little startups are more in tune in making experiments. It's really a kind of what is my mindset, and the mindset is a strange word, but what is my basic habit about how to embrace new things. What is the way I perceive the world? Every entrepreneur who tries to create it or say it different way, even entrepreneurs nowadays need to create business plans. The basic ideas I can show to investors, everything is already mapped out. I have already clients. I have a proven business model. That is completely crazy because If it were a proof business model, someone else would have already done it, right? So obviously you need to come up with the idea that a kind of entrepreneur mindset is a little bit like I try to create something that is much more interesting to phrase it this way. by creating something, it's like art. You can't, can't... Plan art, I mean, it's impossible. I mean, you might have an idea and you might maybe someone who's writing texts or novels might create a huge outline. But on the other hand, within that outline, he needs to be creative again. And someone will say, I just start by getting continuous feedback. It's always the same. You need to create something to be able to observe it. that was for me, for me, that was the epiphany or the idea 25 years ago was, I don't know what your background is, but I wasn't a business analyst. Business analysts always wanted to write documents that the developer can really implement, right? And then we figured out you can't write down what you need to implement. There's no way of writing requirements in the way that someone else can build it. That's impossible. And even philosophers figure that out 100 years ago is written, Shanti said, you can't tell people what is the case. It's impossible. So, but what you can do, you can create something and you can have it in your review. And then you can start discussing about what you just created. And then you create a new result based on your observations and the next investment that you put in that. And then you create the next version of your product, your feature, your service, et cetera. Brian Milner (15:12) Hmm. Boris Gloger (15:25) And when we came back to the entrepreneur mindset and starting companies, Greaves created exactly that. He said, okay, let's use scrum to come up with as much possibilities for experimentation. And then we will see if it works. Then we can go on at that. And large corporations typically, They have on the one hand side, have too much money. And by having too much money, you would like to get an investment and they have a different problem. Typically large corporations typically needs to, they have already a specific margin with their current running products. And if you come up with a new business feature product, you might not get that as that amount of of revenue or profitability at the beginning. And therefore, can't, corporations have the problem that they have already running business and they are not seeing that they need to spend much, much more money on these opportunities. And maybe over time, that opportunity to make money and that's their problem. So this is the issue. It's not about entrepreneurial mindsets, it's about that. problem that you are not willing to spend that much money as long as you make much more money, it's the same amount of time on your current business. It happens even to myself, We are running a consulting company in Germany and Austria, and Austria is much smaller than Germany's tenth of the size. And if you spend one hour of sales in Austria, you don't make that much money in Austria than you make in Germany. this investment of one hour. Where should you focus? You will always focus on Germany, of course. means obvious. Brian Milner (17:08) Yeah. Yeah. Boris Gloger (17:10) Does it make sense? Maybe I'm running so. Brian Milner (17:14) No, that makes sense. That makes sense entirely. And so I'm kind of curious in this conversation about action and having a bias toward action then, what do you think are some of the, in your experience in working with companies, what have you seen as sort of the common obstacles or barriers, whether that be psychological or. organizational, what do you find as the most common barriers that are preventing people from having that bias toward action? Boris Gloger (17:44) the they are they are afraid of the of that of tapping into the new room endeavor. So that was always my blind spot because I'm an entrepreneur. I love to do new things. I just try things out. If I've either reading a book, and there's a cool idea, I try to what can happen. But we are not And most organizations are not built that way that they're really willing to, when most people are not good in just trying things out. And most people would really like to see how it's done. And most people are not good in... in that have not the imagination what might be possible. That's the we always know that product adoption curve, that the early adopters, the fast followers, the early minority, the late minority. And these inventors or early adopters, they are the ones who can imagine there might be a brighter future if I try that out. And the other ones are the ones who need to see that it is successful. And so whenever you try implementing Scrum or design thinking or mob programming or I don't whatever it is, you will always have people who say it's not possible because I don't have, haven't seen it before. And I sometimes I compare that with how to how kids are learning. Some kids are learning because they see how what is happening. They just mirroring what they see. And some kids are start to invent the same image in imagination. And but both that we are all of us are able to do both. It's not like I'm an imaginary guy who's inventing all the time and I don't, people, maybe there's a preference and the organizations have the same preference. But typically that's the problem that I see in organizations is based on our society and our socialization, on our business behaviors and maybe the pressure of large corporations and all that peer pressure is Brian Milner (19:34) Yeah. Yeah. Boris Gloger (19:54) The willingness to give people the room to try something out is the problem. Well, not the problem, it's the hinders us of being more innovative in organizations. Brian Milner (19:59) Yeah. Yeah. Well, that brings to mind a good question then too, because this experimentation mindset is very, very much a cultural kind of aspect of an organization, which speaks to leadership. And I'm kind of curious from your perspective, if you're a leader, what kind of things can you do as a leader to encourage, foster, of really nurture? that experimentation mindset in your organization. Boris Gloger (20:34) Let's have a very simple example. Everybody of us now maybe have played with chat, CPT, Suno, perplexity and so on. So that's the school AI technology around the corner. And what happens now in organizations is exactly what happens 30 years ago when the internet came here. You have leadership or managers who say, that's a technology, I give it to the teams, they can figure out whatever that is. And the funny thing is, if you have a technology that will change the way we behave, so it's a social technology, a kind of shift, then I need to change my behavior, I need to change the way I do I'm doing things. Yeah, everybody of us has now an iPhone or an Android or whatever it is, but but we are using our mobiles in a completely different way than 30 years ago. And to lead us and manage us, we need to train ourselves first before we can help our teams to change. So the problem is that Again, a lot of Agilist talks about we need, first we need to change the culture of organizations to be able to do Agile and so on and so on. That's complete nonsense. But what we really need to is we need to have managers, team leads, it with team leads, to help them to do the things themselves because Agile, even in the beginning, now it's technology change, now it's AI, is something that changes the way we do our stuff. It's kind of habit. And we need to help them to seize themselves. Maybe they can only seize themselves by doing that stuff. And that goes back to my belief that leadership needs to know much more about the content of their teams and the way these teams can perform their tasks and the technology that is around to be able to thrive in organizations. Brian Milner (22:40) Yeah. Yeah. I love this discussion and I love that you brought up, you know, AI and how that's affecting things here as well. how do you think that's having a, do you think that's making it easier, harder? How do you think AI is, is kind of influencing this bias toward action mentality? Boris Gloger (22:59) Yeah, it depends on if you are able to play. mean, because the funny thing is, it's a new kind of technology. really knows what all these tools can do by themselves. And it's new again. It's not like I have done AI for the next last 10 years and I know exactly what's possible. So we need to play. So you need to log in to adjust it. Yesterday, I tried something on Zulu. I created the company song in 10 seconds. I went to ChatGVT, I said I need a song, I need lyrics for a company song. These are the three words I would like to have, future, Beurus Kluger, and it needs to be that kind of mood. ChatGVT created the song for my lyrics, then they put the lyrics into the... And they created a prompt with ChatGVT and then put that prompt in my lyrics into Sono and Sono created that song within 10 seconds. I mean, it's not get the Grammy. Okay. It's not the Grammy. But it was, I mean, it's, it's, it's okay. Yeah. It's a nice party song. And now, and just playing around. And that is what I would like to see in organizations, that we start to play around with these kind of technologies and involve everybody. But most people, the very discussions that I had in the last couple of weeks or months was about these tools shall do the job exactly the same way as it is done today. So it's like... I create that kind of report. Now I give that to Chet Chibati and Chet Chibati shall create that same report again. That is nonsense. It's like doing photography in the old days, black and white. And now I want to have photography exactly done the same way with my digital camera. And what happened was we used the digital cameras changed completely the way we create photography and art. changed completely, right? And that is the same thing we need to do with ChatGV team. And we need to understand that we don't know exactly how to use it. And then we can enlarge and optimize on one hand the way we are working, for instance, creating 20 different versions for different social media over text or something like that, or 20 new pictures. But if I would like to express myself, so, and... and talk about my own behavior or my own team dynamic and what is the innovation in ourselves, then we need to do ourselves. And we can use, that is the other observation that we made. The funny thing that goes back to the knowledge issue, the funny thing is that teams typically say, I don't know if it's in the US, but at least in my experience, that we still have the problem within teams. that people believe this is my know-how and that is your know-how and I'm a specialist in X or Y set. So they can't talk to each other. But if you use maybe chat GPT and all these tools now, they can bridge these know-how gaps using these tools. And suddenly they can talk to each other much faster. So they get more productive. It's crazy. It's not like I'm now a fool with a tool. I can be a fool and the tool might help me to overcome my knowledge gaps. Brian Milner (26:20) Now this is awesome. I know that your book that's coming out, Strategy is Practice, talks about a lot of these things. Tell us a little bit about this book and kind of what the focus is. Boris Gloger (26:30) the basic idea when I started doing working on the on strategies, we be in the the actual community, we talk about strategy as what is a new idea of being OKR. So OKR equals strategy, and that is not true. And I came up with this basic idea, what is the basic problem of of strategic thinking and we are back to the in most organizations, we still believe strategy is the planning part and then we have an implementation part. And years ago, I came across a very basic, completely different idea that said every action is strategy. Very simple example. You have the strategy in a company that you have a high price policy. Everything you do is high price. But then you are maybe in a situation where you really need money, effort, revenue issues, liquidation, liquidation problems. Then you might reduce your price. And that moment, your strategy is gone. just your obviously and you have now a new strategy. So your actions and your strategies always in line. So it's not the tactic for the strategy, but tactic is strategy. And now we are back to Azure. So now we can say, okay, we need kind of a long-term idea. And now we can use for creating the vision. For instance, you list the V2MOM framework for creating your vision. But now I need to have a possibility to communicate my strategic ideas. And in the Azure community, we know how to do this. We have plannings and we have dailies and we have reviews and retrospectives. So now I can use all these tools. I can use from the bookshelf of Azure tools. I can use maybe OKRs to create a continuous cycle of innovation or communication so that I get that everybody knows now what is the right strategy. And I can feed back with the reviews to management. that the strategy approach might not work that way that they believed it's possible experimentation. And then and I added two more ideas from future insight or strategic foresight, some other people call it. So the basic idea is, how can I still think about the future in an not in the way of that I have a crystal ball. But I could say, how can I influence the future, but I can only influence the future if I have an idea what might be in future. It's like a scenario. Now you can create actions, power these kind of scenarios that you like, or what you need to prevent a specific scenario if you don't like that. And we need a third tool, that was borrowed from ABCD risk planning, was the basic idea, how can I get my very clear a very simple tool to get the tactics or the real environmental changes like suddenly my estimates might not be correct anymore or my suggestions or beliefs about the future might not get true in the future. So I need kind of a system to feed back reality in my strategy. it's a little bit like reviewing all the time the environment. And if you put all that together, then you get a very nice frame how to use strategy on a daily practice. It's not like I do strategy and then have a five-year plan. No, you have to do continuously strategy. And I hope that this will help leaders to do strategy. I mean, because most leaders don't do strategy. They do tactic kind of work. and they don't spend They don't spend enough time in the trenches. to enrich their strategies and their thinking and their vision. because they detach strategy and implementation all the time. That's the basic idea. Brian Milner (30:30) That's awesome. That sounds fascinating. And I can't wait to read that. That sounds like it's going to be a really good book. So we'll make sure that we have links in our show notes to that if anyone wants to find out more information about that or learn more from Boris on this topic. Boris, can't thank you enough for making time for coming on. This has been a fascinating discussion. Thank you for coming on the show. Boris Gloger (30:40) Yeah. Yeah, thank you very much for having me on your show and appreciate that your time and your effort here. Make a deal for the, it's very supporting for the agile community. Thank you for that. Brian Milner (30:57) Absolutely. Yeah, yeah, thank you.
Ever wonder what's really happening in the OKR world beyond the hype?Join Sara Lobkovich, Maria Rowcliffe, and Natalie Webb for a candid, no-BS look at where OKRs are heading in 2025. This isn't your typical "here's how to write an objective" conversation. Instead, you'll get insider insights from three veteran practitioners who've been in the trenches, helping organizations navigate the messy reality of goal-setting and alignment at scale.In this first part of our quarterly update, we dive deep into the generative AI revolution (spoiler: it's not as revolutionary as everyone claims), the evolving art of OKR localization across complex organizations, and why your retrospectives might be the most important OKR practice you might be doing wrong. Whether you're an OKR skeptic, a seasoned practitioner, or somewhere in between, this conversation will give you practical insights you can't get anywhere else.Episode Highlights:Generative AI in OKRs: why draft quality is improving, but real strategic impact is still lagging behindTRV (Technology Realized Value): the Big Five's new metric for linking OKRs to actual tech investment outcomesThe “Two Lists” Problem: how teams are secretly working off dual strategies—and why it's undermining OKR focusCascading and Localization: evolving models for aligning across global teams, even amid geopolitical complexityCulture-First OKRs: tailoring implementation to readiness, from transformation-driven overhauls to scrappy gradual rolloutsRetrospectives that matter: how deeper reflection—not just review—builds quarter-over-quarter OKR maturityKey Concepts Explored:Generative AI in OKRs: Where it's accelerating strategy work, where it's falling short, and the risk of generic, uncontextualized modelsTechnology Realized Value (TRV): A new metric used alongside OKRs to measure the tangible impact of tech investmentsThe “Two Lists” Problem: How parallel strategic workstreams outside the OKR framework dilute focus and undermine accountabilityLocalization & Alignment: Why clear, bottom-up contribution is critical in global, matrixed organizations—especially in high-stakes geopolitical climatesCulture-Responsive Implementation: Tailoring OKR rollouts based on organizational readiness, risk appetite, and transformation goalsIterative Learning over Perfection: Why OKR maturity builds quarter over quarter—and how learning from retrospectives is more valuable than writing the “perfect” OKRLeading vs. Lagging Indicators: The power of AI to help surface potential leading indicators clients may struggle to define on their ownTransformation & Change Management: How OKRs, when paired with transformation strategy, become powerful drivers of organizational evolutionNotable Quotes: "Is this really driving the value you wanted to achieve? How do you know who cares? So what happens if this is done or not done? These things that don't get asked are so critically important to make sure that people are focused on the right work." — Natalie Webb [00:12:00]"If I could only tell clients one thing about OKRs, it would be we spend all of our time focused on writing them and then way too little time focused on learning from them." — Sara Lobkovich [00:23:00]"I think the best way to use OKRs initially is always the way that the company is willing and able to adopt it. Me talking about the gold star way of doing OKRs isn't gonna help clients that are at the crawling level and not a hundred percent convinced yet." — Maria Rowcliffe [00:21:00]"OKRs are really hard. We're talking about change - really hard for people to stick with when it gets challenging." — Sara Lobkovich [00:28:00]Chapters:[00:00:00] Introduction:...
Join us in this episode as we explore the world of complex problem-solving across industries with Hunter S. Gaylor, an executive partner, financial expert, and author. Hunter is a highly accomplished business leader with a diverse range of expertise spanning mobile banking, corporate strategy, private aviation, and international relations. He holds a Bachelor of Liberal Arts degree from Harvard University, is the Founder of Spencer Pruitt, and is the author of Planes Plants and Politics: A Mental Framework To Help Overcome Challenges in Any Industry. Click play to find out: The one thing that kills more strategies more than anything else. The importance of being able to accurately articulate what you're doing and why you're doing it. The driving force behind discipline and action. Why identifying the motivating factors behind specific goals. Discover the strategies behind Hunter S. Gaylor's guidance that drives worldwide business success – join the conversation now! You can follow along with Hunter on X @HunterGaylor and LinkedIn. Episode also available on Apple Podcasts: http://apple.co/30PvU9
Tim Herbig Connecting the dots of Product Strategy, Product OKRs, and Product DiscoveryIn this episode, we welcome Tim Herbig, a product leadership coach with a special focus on OKRs, in addition to product strategy and discovery. Tim shares his unique journey from product management to coaching, elaborating on the complexities and nuances of implementing OKRs in various business contexts. Through his insightful discussion, Tim covers the misconceptions about OKRs, the importance of adapting them to your specific needs, and effective strategies for measuring success. He also dives into the integration of product discovery and product strategy with OKRs, offering practical advice for product leaders facing challenges with OKR implementation. Whether you're in a startup or a large enterprise, Tim's expertise provides valuable perspectives on how to make OKRs work for your team.00:00 Introduction and Guest Welcome00:48 Tim Herbig's Journey into Product Management01:52 Transition to Coaching and Consultancy03:53 Specialization in OKRs and Product Management06:50 Adapting OKRs to Different Contexts09:46 Challenges and Strategies in OKR Implementation13:58 Measuring Success and Influence in OKRs22:47 OKRs in Product vs. Broader Company Context25:38 The Role of OKRs in Strategy and Discovery27:11 Confidence and Hypotheses in Strategy29:36 OKRs in Startups vs. Large Enterprises32:07 Adapting OKRs to Fit Your Context33:47 Common Misconceptions and Best Practices40:00 Aligning OKRs Across Teams47:43 When to Bring in OKR Support50:57 Conclusion and Contact Information
Are you building a startup strategy—or just making it look like you have one?Too many founders mistake polished slide decks for actual strategic thinking, leading to misalignment, wasted resources, and failed products.In this episode, Yaniv Bernstein and Chris Saad are joined by Marcelo Calbucci, former Amazon director and author of The PRFAQ Framework. They dive into how Amazon's famously effective six-page PRFAQ process forces deep thinking, aligns teams, and drives billion-dollar bets—without a single slide.They explore why most startups get strategy wrong, how to apply PRFAQs to your own company, and the real difference between outputs and outcomes.In this episode, you will:Discover why PowerPoint-based strategies often lead to shallow thinking and misalignmentLearn how Amazon's six-page PRFAQ framework drives innovation and clarityUnderstand the structure of a PRFAQ—and why it starts with a future-facing press releaseExplore the critical cultural shifts needed to make frameworks like PRFAQs workCompare PRFAQs with OKRs and PRDs—and learn when to use eachUnpack the process Amazon uses to critique and improve strategy docs in real timeHear practical advice on adapting the PRFAQ process to your startup, even as a solo founderWhether you're pre-launch or scaling fast, this episode gives you a blueprint for thinking deeper and aligning your team.The Pact Honor the Startup Podcast Pact! If you have listened to TSP and gotten value from it, please:Follow, rate, and review us in your listening appSubscribe to the TSP Mailing List to gain access to exclusive newsletter-only content and early access to information on upcoming episodes: https://thestartuppodcast.beehiiv.com/subscribe Secure your official TSP merchandise at https://shop.tsp.show/ Follow us here on YouTube for full-video episodes: https://www.youtube.com/channel/UCNjm1MTdjysRRV07fSf0yGg Give us a public shout-out on LinkedIn or anywhere you have a social media followingKey linksGet your question in for our next Q&A episode: https://forms.gle/NZzgNWVLiFmwvFA2A The Startup Podcast website: https://www.tsp.show/episodes/Learn more about Chris and YanivWork 1:1 with Chris: http://chrissaad.com/advisory/ Follow Chris on Linkedin: https://www.linkedin.com/in/chrissaad/ Follow Yaniv on Linkedin: https://www.linkedin.com/in/ybernstein/Producer: Justin McArthur https://www.linkedin.com/in/justin-mcarthurIntro Voice: Jeremiah Owyang https://web-strategist.com/
In today's workplaces, OKRs (Objectives and Key Results) and KPIs (Key Performance Indicators) are two widely used frameworks to drive performance and accountability. While KPIs focus on tracking performance through specific metrics—think sales numbers, response times, or customer satisfaction—OKRs are more about setting bold, aspirational goals with measurable outcomes that align teams around a shared purpose. As Gen Z enters the workforce, with their strong preference for meaning, transparency, and impact, the way organizations design and communicate these goals becomes even more important. In this episode, we explore how these frameworks resonate with Gen Z: Do they feel empowered or boxed in by structured goal setting? And how can companies evolve their approach to performance management to better engage this values-driven generation?Find out more in this episode, as Leadership Expert Kennet Lewise helps us to understand Why goal setting matters more than ever in today's fast-changing workplace?How Gen Z views goal setting: structure vs. autonomyDo traditional OKRs feel too rigid or just right for Gen Z?Making OKRs meaningful: the role of purpose and impactThe importance of real-time feedback and recognition in the OKR cycleCo-creating OKRs: How managers can engage Gen Z in the processPitfalls to avoid when applying OKRs with younger teamsReal-life examples of how OKRs have helped—or hurt—Gen Z engagementTips for making OKRs more inclusive, transparent, and motivatingThe future of performance management in a Gen Z-driven workplace 45 Best Gen Z Podcasts You Must Follow in 2025Find Us OnlineKenneth Lewis : Website, LinkedInNikhil : Website, Linkedin, Youtube & Book
Today we're talking about how 100% of my clients gained clarity and courage to make MAJOR business and career moves. Those mind blowing quantum leaps that don't come from more grind and hustle, faking it till you make it, or another certificate from the likes of Harvard's Extension School, but from identity shifts.Ali left Microsoft to pursue a health tech startup. She used OKRs and mindset tools to go from insecure and scattered to strategic—and made her dream real in 180 days.Melissa was newly promoted and was building a department alone and ready to collapse. In 90 days, she rewired her brain, rebuilt her team, and reclaimed her joy at work in 90 days.Pam was going to quit her job. Instead, she reconnected with her mission and now leads with clarity, calm, and confidence again in 90 days.Morgan raised a round of funding, sold her company, and followed her dream of going to Harvard Business School in 180 daysKatherine was newly promoted and craved confidence in high-stakes moments like speaking to the board, and I was flirting with burnout. 90 days later she feels free, curious, and grounded in her career, and presence as an executive.
Episode SummaryThis episode explores the nuances of scaling demand generation strategies from startups to established organizations. Lily Youn highlights the importance of building a strong foundation through account-based strategies, data hygiene, and team alignment. She discusses the differences between startup scrappiness and scale-up structure, the role of AI in demand generation, and how to identify quick wins for immediate impact. Lily also shares actionable insights for optimizing conversions, improving CRM processes, and fostering collaboration across teams..Key TakeawaysFoundation is EssentialSuccess in demand generation starts with targeting the right accounts, as they form the base of effective strategies.Alignment Creates MomentumRegular, agenda-driven meetings with key stakeholders help ensure seamless collaboration between sales and marketing.AI as an Efficiency DriverAI tools can streamline personalization, simplify content operations, and elevate demand gen workflows.Data Hygiene is Non-NegotiableClean, well-structured CRM data is critical for reliable reporting and scalability across company stages.Startup vs. Scale-Up DynamicsStartups require focused ICP development, while scale-ups demand scalable processes and systems.Quotes"Targeting the wrong prospects is the single biggest challenge in B2B sales today."Best Moments (01:37) – Lily shares her career journey from BDR to demand generation leader, reflecting on early lessons in scrappiness and resourcefulness.(04:50) – The critical role of account-based strategies and why a strong foundation starts with the right ICP.(07:20) – Navigating startup-to-scale-up transitions and the importance of scalable processes and clean CRM data.(12:07) – Leveraging tech and AI to enhance efficiency in demand generation and content operations.(14:00) – Lily's focus on alignment, OKRs, and communication as keys to success in scaling demand gen teams.Tech RecommendationsWorkBoard – For setting and tracking OKRs to maintain team alignment and prioritize business goalsZoomInfo Co-Pilot – An AI-powered tool for streamlining demand gen efforts and improving account targeting.Asana – A project management solution to enhance productivity and maintain focus on KPIs.Resource RecommendationsBooks:Reset: How to Change What's Not Working by Dan Heath – A guide for improving leadership practices and daily operations.Shout-OutsShannon Hawari - Head of Growth @ elvexGraham Collins - Head of Partnerships at QuotaPathAbout the GuestLily Youn Jaroszewski is the VP of Demand Generation and Revenue Marketing at Aprimo, the leading digital asset management technology for marketing and customer experience departments.Her experience in B2B and B2C tech companies includes building demand generation teams and quota capacity models to support AEs from Seed-Funded to Public companies.Website: aprimo.comConnect with Lily.
BONUS: Tom Gilb on Building True Engineering Culture and Delivering Value Through Evolutionary Methods In this BONUS episode, we dive deep into the world of true engineering discipline with Tom Gilb, a pioneer who was writing about Agile principles before Agile was even named. We explore his latest book "Success - Super Secrets & Strategies for Efficient Value Delivery in Projects and Programs, and Plans" and uncover the fundamental flaws in how organizations approach project delivery and stakeholder management. The Genesis of Success-Focused Engineering "People were failing at project deliveries - even when using Agile. I saw there was very little about setting clear goals and reaching them, it had nothing to do with being successful." Tom's motivation for writing his latest book stems from a critical observation: despite the widespread adoption of Agile methodologies, project failure rates remain unacceptably high. The core issue isn't methodology but rather the fundamental lack of clarity around what success actually means. Tom emphasizes that true success is about achieving the improvements you want at a price you can afford, yet most organizations fail to define this clearly from the outset. In this segment, we refer to the book How Big Things Get Done by Bent Flyvbjerg who published statistics on the poor performance of projects in general. Beyond OKRs: The Power of Quantified Multi-Dimensional Objectives "First you need to have a definition of what it means to succeed. And that needs to be multi-dimensional. And you need to clarify what they are." While many organizations believe they're already quantifying objectives through frameworks like OKRs, Tom reveals significant weaknesses in these approaches. True value isn't just profit—it encompasses multiple dimensions including security, usability, and other stakeholder-specific benefits. The key insight is learning to quantify what needs to be achieved across all critical dimensions, as you simply cannot design for high-quality attributes like security without first quantifying and designing for them explicitly. In this segment, we talk about Tom's paper on OKR's titled "OKR Objectives and Key Results: what's wrong and how to fix it". The Missing Engineering Discipline "Why is the failure rate of our projects so high?" Tom identifies a paradoxical problem: engineering organizations often lack true engineering discipline. This fundamental gap explains why project success rates remain low despite technological advances. Real engineering requires systematic approaches to design, stakeholder analysis, and incremental value delivery—disciplines that are often overlooked in favor of rushed implementations. Stakeholder Analysis: Beyond User Stories "Stakeholders have a requirement - even if we don't know it. They might be people, but also law, contract, policies, etc. They all have requirements for us." Traditional user-centered methods like user stories can lead to failure when critical stakeholders are overlooked. Tom advocates for comprehensive stakeholder analysis as the foundation of engineering discipline. Stakeholders aren't just people—they include laws, contracts, policies, and other constraints that have requirements for your system. The practical tip here is to use AI tools to help identify and list these stakeholders, then quantify their specific requirements using structured approaches like Planguage. The Gilb Cycle: True Incremental Value Delivery "Get things done every week, next week, until it's all done. We need to decompose any possible design into enough increments so that each increment delivers some value." What distinguishes Tom's evolutionary approach from popular Agile frameworks is the focus on choosing the most efficient design and then systematically improving existing systems through measured increments. Each increment must deliver tangible value, and the decomposition process should be aided by AI tools to ensure optimal value delivery. This isn't just about iteration—it's about strategic improvement with measurable outcomes. Building Engineering Culture: A Two-Leader Approach "There are two leaders: the tech leaders and the management leaders. For management leaders: demand a value stream of results starting next week. To the tech leaders: learn the engineering process." Creating a true engineering culture requires coordinated effort from both management and technical leadership. Management leaders should demand immediate value streams with weekly results, while technical leaders must master fundamental engineering processes including stakeholder analysis and requirement quantification. This dual approach ensures both accountability and capability development within the organization. Further Resources During this episode we refer to several of Tom's books and papers. You can see this list below Software Metrics by Tom Gilb Principles of software engineering management - Also available in PDF Evo book About Tom Gilb Tom Gilb, born in the US, lived in London, and then moved to Norway in 1958. An independent teacher, consultant, and writer, he has worked in software engineering, corporate top management, and large-scale systems engineering. As the saying goes, Tom was writing about Agile, before Agile was named. In 1976, Tom introduced the term "evolutionary" in his book Software Metrics, advocating for development in small, measurable steps. Today, we talk about Evo, the name that Tom used to describe his approach. You can link with Tom Gilb on LinkedIn.
Since 2014, Ryan Holiday's The Daily Stoic newsletter has landed in inboxes every single morning, offering ancient wisdom in bite-size, highly clickable form.It's also a masterclass in content marketing. In this episode, we're unpacking what B2B marketers can learn from The Daily Stoic with the help of Amanda Dyson, VP, Head of Marketing at FourKites.Together, we explore how to break the marketing mold, why the most impactful content is also the most practical, and how anchoring your message in core values makes it stick. Stoicism isn't just a philosophy; if done right, it's a blueprint for modern marketing.About our guest, Amanda DysonWith 20 years B2B software and SaaS marketing expertise, Amanda specializes in go-to-market strategy; consultative marketing; change and people management; lead generation; account based marketing; partner co-marketing; integrated digital marketing; email marketing; live and virtual events; corporate branding and storytelling; account segmentation and targeting; project and budget management, and strategic advisement.Amanda has run regional and global teams. She has a passion for people and results and a proven track record of success delivering on KPIs and OKRs. She has held successively responsible, cross-functional leadership positions in sales and marketing, including alliances, partnership marketing, ABM, demand generation, field marketing, solutions marketing, events, communications, and corporate marketing for global Supply Chain Management (SCM) and Enterprise Resource Planning (ERP) software companies.A California girl at heart, Amanda happily resides in Charlotte, North Carolina with her family of five. When she's not growing people or pipeline at leading tech companies, she enjoys spending time with her family in the mountains or at the beach, running daily, and practicing mindfulness. Amanda has an MBA from the W.P. Carey School of Business at Arizona State University with a focus in Marketing, Finance and Supply Chain, and a Bachelor of Arts degree in Business Economics with a Minor in Professional Writing from the University of California, Santa Barbara.What B2B Companies Can Learn From Ryan Holiday's The Daily Stoic Newsletter:Break the marketing mold. Stoicism may be ancient, but Ryan Holiday has made it feel new and modern. Amanda sees that reinvention as a creative north star. She says, “Let's do something wild. Some of my favorite marketing campaigns have just been weird stuff. It breaks the mold and it gets something done.” Ryan Holiday didn't market stoicism by copying academic textbooks, he made it approachable and surprising. B2B marketers should do the same. Surprise earns attention. A little weirdness, done with purpose, goes a long way.Make it usable, not just insightful. Ryan Holiday's greatest trick isn't sounding smart, it's making stoicism actionable. Amanda says, “He does things in such a bite-size, practical way that you can hold onto it.” That's exactly how B2B content should work. Don't just publish thought leadership that nods at trends. Give your audience tools they can actually apply. Teach them something they'll remember at 4 PM on a chaotic Tuesday. If it doesn't help them do their job better, it's just noise.Anchor your content in core values. The Daily Stoic isn't random. It's rooted in four core tenets: courage, temperance, justice, and wisdom. Amanda draws the parallel for marketers: “It's all fostered and rooted in these core values or the stoic virtues, which you could look at your brand pillars in the same kind of light.” B2B content should be more than campaign-deep. When your content reflects your company's true values, it resonates longer and travels farther. Think less about filling the calendar, and more about reinforcing what you stand for. Quotes*“ I really challenge my teams to get back to storytelling. You gotta break out of the box, so let's do something wild. Some of my favorite marketing campaigns I've ever done have just been weird stuff: bobbleheads, robots on the beach. Random things that are not B2B software, but it breaks the mold and it gets something done. I think Ryan's done that with his marketing of stoicism. He's broken the mold, right? He reinvigorated this ancient philosophy, and so that's definitely a lesson I think we can learn from him too on content.”*“ So we are all about how do we take one thing and reuse it in different ways. I think if we look at Ryan and his newsletter, I kind of mentioned his repetition. I don't think he sends the exact same newsletter, you know, multiple times. But there's certainly similar messages where you can go back in your archives and dig those things up again and present it in a different way. Content is huge. It drives, internally and externally, all of our activities. But you gotta be really smart about how you do it and how you use it, 'cause you're competing with so much noise. It can definitely be challenging to again break that mold.”*“ Something that makes him a tremendous marketer is that he really believes in what he's selling us, right? He's created this brand that is a lifestyle. Stoicism is a philosophy, so there's a lot of high value attached to it and how you live your life.”Time Stamps[0:55] Meet Amanda Dyson, VP, Head of Marketing at FourKites[00:58] Why Ryan Holiday's The Daily Stoic Newsletter[03:04] The Role of VP, Head of Marketing at Four Kites[04:18] Origins of Ryan Holiday's The Daily Stoic[09:27] Understanding Tucker Max[13:12] Stoicism 101: Old Ideas for Modern Chaos[20:23] Building a Daily Ritual[22:21] Strategies for Writing Like a Pro[25:35] Inspiration as a Driver for Your Content[35:55] Creating Marketing Tactics That Actually Matter[39:00] FourKites' Content Strategy[40:31] What's Working for Amanda Now?[44:15] Measuring ROI at Four Kites[49:49] Advice for Marketing Leaders[51:27] Final Thoughts and TakeawaysLinksConnect with Amanda on LinkedInLearn more about FourKitesAbout Remarkable!Remarkable! is created by the team at Caspian Studios, the premier B2B Podcast-as-a-Service company. Caspian creates both nonfiction and fiction series for B2B companies. If you want a fiction series check out our new offering - The Business Thriller - Hollywood style storytelling for B2B. Learn more at CaspianStudios.com. In today's episode, you heard from Ian Faison (CEO of Caspian Studios) and Meredith Gooderham (Head of Production). Remarkable was produced this week by Jess Avellino, mixed by Scott Goodrich, and our theme song is “Solomon” by FALAK. Create something remarkable. Rise above the noise.
כשה-OKR מוטמעים נכון, זה קסם. הם ממקדים, מניעים ומייצרים שפה משותפת שמאפשרת לצוותים לשתף פעולה ולהתקדם. אבל אם אחרי שני רבעונים התחושה היא שה-OKR עובדים עליכם יותר משאתם עובדים איתם – כנראה שמשהו צריך להשתנות. בפרק הזה, גלעד מארח את עדי סוזן, מומחית לניהול מוצר ו-OKR, לשיחה פתוחה על איך לעשות את זה נכון. מה בפרק? למה בכלל OKR? חיבור בין ויז'ן, אסטרטגיה וביצוע יומיומי, מיקוד במה שחשוב עכשיו, שפה משותפת בין צוותים, והנעה של שינוי אמיתי. העקרונות שמחזיקים את השיטה: Outcome > Output, חשיבה בסגנון Moonshot, העצמה של הצוותים (ולא רק ביצוע), ושימוש בריטואלים שבועיים ורבעוניים לתיאום והכוונה. איך מתחילים נכון? להתחיל קטן, לוודא שיש buy-in מהנהלה, לבחור מטרה משמעותית ולא רק פרויקט, ולבנות שגרות עבודה ברורות אך לא בירוקרטיות. מתי זה לא עובד? סימני אזהרה נפוצים כמו עבודה בשביל ה-OKR במקום שהם ישרתו אתכם, חוסר שיח פתוח, מדדים שלא באמת משקפים שינוי, והתעקשות על השלמת משימות גם כשברור שאין להן ערך. איך לתקן? סבלנות (לפחות רבעון-שניים), רטרוספקטיבה מתמדת, בדיקה אמיתית של יכולות הצוות (capacity), ומיקוד בשיתוף פעולה על ההזדמנויות הגדולות ביותר. דוגמאות מהשטח: איך OKR משותפים בין צוותים הצליחו לשפר את חוויית הלקוח ולקצר את הדרך לערך.
Better Business Better Life! Helping you live your Ideal Entrepreneurial Life through EOS & Experts
Welcome to Better Business, Better Life. In this episode, host Debra Chantry-Taylor breaks down why EOS Rocks are a better fit than OKRs for entrepreneurial and fast-growing businesses. She discusses how OKRs often lead to confusion, scattered focus, and poor follow-through while EOS Rocks bring clarity, accountability, and weekly progress. With practical tips on setting quarterly priorities, assigning clear ownership, and using tools like the Accountability Chart, Scorecard, and Level 10 Meetings, Debra shows how to build a simple, effective execution system that actually works. If you're feeling stretched too thin by endless objectives, this episode will show you how to simplify, refocus, and gain real traction. CONNECT WITH DEBRA: ___________________________________________ ►Debra Chantry-Taylor is a Certified EOS Implementer | Entrepreneurial Leadership & Business Coach | Business Owner ►Connect with Debra: debra@businessaction.co.nz ►See how she can help you: https://businessaction.co.nz/ ____________________________________________ Chapters: 00:26 - Introduction to EOS Rocks vs. OKRs 01:07 - Defining OKRs and EOS Rocks 01:58 - Challenges with OKRs in Entrepreneurial Businesses 03:19 - The Power of EOS Rocks and Accountability 05:35 - Real-Life Examples of EOS Rocks in Action 07:08 - Conclusion and Call to Action
In this powerful episode of the Jake & Gino podcast, we're joined by Rob Finlay—serial entrepreneur, founder of 30 Capital, and author of Beyond the Building and Hey Dad. Rob dives deep into commercial real estate debt strategy, the importance of tracking OKRs and KPIs, and the long-term thinking that separates real estate professionals from amateurs.But this conversation doesn't stop at business. Rob also opens up about parenting adult children, financial literacy, and the “green gas” phone call that inspired his latest book, Hey Dad, a must-read for any parent raising self-sufficient young adults in today's world.Whether you're a multifamily investor looking to improve your financial game or a parent preparing your kids for life, this episode delivers hard-earned insights from one of the best in the business.Get the books:Hey Dad: https://heydadbook.comConnect with Rob FinlayWebsite: https://robfinlay.comInstagram & more: @robfinlay Chapters:00:00 - Introduction 04:54 - KPIs & OKRs Explained (with Chick-fil-A References) 14:47 - Smart Leverage & Exit Strategies 18:15 - How New Investors Should Think About Equity, Recycling Deals, and Exit Strategies 21:41 - Refinancing vs. 10-Year Lockups 29:24 - The 2021–2022 Bridge Debt Trap 32:49 - Hey Dad: The Gas Pump Phone Call That Started It All 39:46 - Real Parenting Talk: Teaching Independence Through Exposure 43:05 - Kids & Money: Raising Financially Literate Adults 49:34 - Gino Wraps it Up We're here to help create multifamily entrepreneurs... Here's how: Brand New? Start Here: https://jakeandgino.mykajabi.com/free-wheelbarrowprofits Want To Get Into Multifamily Real Estate Or Scale Your Current Portfolio Faster? Apply to join our PREMIER MULTIFAMILY INVESTING COMMUNITY & MENTORSHIP PROGRAM. (*Note: Our community is not for beginner investors)
Ben is the President and founder of OKRs.com. For those unfamiliar with this concept…OKRs stands for Objectives and Key Results. And Ben has more OKR coaching experience than anyone on the planet. He has literally helped thousands of leaders learn how OKRs are different than performance metrics and how to use them as a navigational tool…not just a management tool. In this episode, Ben shares stories from some of the most iconic companies in the world and how OKRs led to a massive transformation…and more importantly…how each of you can as well to create inflection points that change the trajectory of YOUR team. You can connect with Ben on LinkedIn here. (https://www.linkedin.com/in/benlamorte/) You can check out OKRs.com here (https://okrs.com/). You can check out Ben's “OKR Field Book Preview” here. (https://okrs.com/the-okrs-field-book-preview/) You can check out Ben's Approach to Implementing OKRs here. (https://okrs.com/coaching/okrs-coaching-remote-program/) For video excerpts of this and other episodes of the Sales Leadership Podcast, check out Sales Leadership United Here. (https://www.patreon.com/c/SalesLeadershipUnited) Be sure to check out the full video of this episode on our YouTube channel here.
Today we're talking about how 100% of my clients gained clarity and courage to make MAJOR business and career moves. Those mind blowing quantum leaps that don't come from more grind and hustle, faking it till you make it, or another certificate from the likes of Harvard's Extension School, but from identity shifts.Ali left Microsoft to pursue a health tech startup. She used OKRs and mindset tools to go from insecure and scattered to strategic—and made her dream real in 180 days.Melissa was newly promoted and was building a department alone and ready to collapse. In 90 days, she rewired her brain, rebuilt her team, and reclaimed her joy at work in 90 days.Pam was going to quit her job. Instead, she reconnected with her mission and now leads with clarity, calm, and confidence again in 90 days.Morgan raised a round of funding, sold her company, and followed her dream of going to Harvard Business School in 180 daysKatherine was newly promoted and craved confidence in high-stakes moments like speaking to the board, and I was flirting with burnout. 90 days later she feels free, curious, and grounded in her career, and presence as an executive.
When it comes to investor relations, an organization's communication strategy should be a key instrument to support its business strategy. While this may seem obvious, so often we get this wrong. In this episode, CJ hosts a masterclass on investor relations with Samuel Levenson and Jon Neitzell of the Arbor Advisory Group, focusing on the strategic role of IR in driving company valuation. They cover what “audience opportunity” really means and what to do when you've attracted the wrong investors. They talk about metrics, KPIs, and OKRs, plus why management credibility and conveying conviction can make or break your IR strategy. They also discuss what has changed in the IR profession over time and what hasn't (but probably should) before suggesting changes you can make to drive impact immediately.If you're looking for an ERP, head to NetSuite: https://netsuite.com/metrics and get the CFO's Guide to AI and Machine Learning.—SPONSORS:Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows—without the hidden fees or unreliable support. Trusted by companies like Linear and Runway, Pulley helps turn ownership into a strategic advantage. Switch in as little as 5 days and get 25% off your first year: pulley.com/mostlymetrics.Tropic is an intelligent spend management solution that consolidates your spend data and processes into one unified offering, enabling insights and decisive action. From spotting hidden optimization opportunities to automating painful procurement workflows and giving you the best market data to turn vendor negotiations in your favor, Tropic combines smart insights with real human expertise to keep you ahead of the curve. Visit tropicapp.io/mostlymetrics to learn how.NetSuite provides financial software for all your business needs. More than 40,000 companies have already upgraded to NetSuite, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you're looking for an ERP platform, head to NetSuite https://netsuite.com/metrics and get the CFO's Guide to AI and Machine Learning.Planful is a financial performance management platform designed to streamline financial tasks for businesses. It helps with budgeting, closing the books, and financial reporting, all on a cloud-based platform. By improving the efficiency and accuracy of these processes, Planful allows businesses to make better financial decisions. Find out more at www.planful.com/metrics.Tabs is the AI-native platform automating contract-to-revenue for fast-growing finance teams. Whether you're working with custom terms, usage-based pricing, or hybrid sales models, Tabs eliminates manual reconciliations and late-night deadlines—giving you clean, automated revenue data from contract to cash. Companies like Cortex and Statsig trust Tabs to streamline invoicing, rev rec, and cash application. Find out more at: tabs.inc/metrics.Rippling Spend is a spend management solution that handles your entire company's spending in one unified system. It enables you to bring your corporate cards, expense management, bill pay, and more into one place to achieve real-time visibility and uniquely granular control with automated policy controls across every type of spend. Get a demo to see how much time your org would save at rippling.com/metrics.—LINKS:Samuel Levenson on LinkedIn: www.linkedin.com/in/samlevenson/Jon Neitzell on LinkedIn: www.linkedin.com/in/jonathan-neitzell/Arbor Advisory Group: www.arboradvisorygroup.com/CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: http://mostlymetrics.com—TIMESTAMPS:(00:00) Preview and Intro(03:10) Sponsor – Pulley | Tropic | NetSuite(07:53) How Your Communication Strategy Should Support Your Business Strategy(10:38) Why You Should Speak to Different Investors Differently(12:11) Defining “Audience Opportunity”(15:24) Sponsor – Planful | Tabs | Rippling Spend(19:18) What To Do if You Have the Wrong Investor Base(22:16) Management Credibility and Conveying Conviction(25:01) Metrics Your Investors Should Be Measuring(32:42) The Metrics That You Should Disclose Versus Guide To(35:45) The Science of the Story Versus the Art of the Story(38:54) Actively Versus Passively Managed Assets(40:50) Working Back to the OKRs That Drive the KPIs(46:58) Why the IR Profession Hasn't Changed Much Over Time(51:11) The Shift in Communications in Recent Years(54:05) Why Production Quality Is Important for Earnings Calls and Investor Days(58:25) How IR Job-Related Technology Has Changed(1:00:07) Changes To Make To Drive Impact Immediately(1:04:23) “Data Transfers Conviction” Get full access to Mostly metrics at www.mostlymetrics.com/subscribe
Subscribe at www.thisnewway.com to get the step-by-step playbooks, tools, and workflows.In episode 4 of This New Way, Aydin sits down with Andrew Waitman, CEO of Assent, to explore how a billion-dollar B2B SaaS company is transforming operations, product development, and team productivity with AI. Andrew shares how Assent went from under $1M to nearly $200M ARR, became one of the earliest adopters of GitHub Copilot and ChatGPT Enterprise, and how they now embed AI-driven OKRs across every team.You'll hear real use cases: from summarizing messy trip reports, generating synthetic bills of materials for secure testing, and accelerating supplier document reviews — to measuring impact on productivity and profitability. Andrew also offers actionable insights on how to drive AI adoption across teams, how CEOs should personally lead the AI charge, and which tools he uses daily to stay ahead.You'll walk away knowing how to start small, scale fast, and turn AI into a measurable force multiplier across your org.Click here to check out the AI-generated timestamps, episode summary and transcript.. . .Like this episode? Be sure to leave a ⭐️⭐️⭐️⭐️⭐️ review and share the episode with someone who will benefit from listening.. . .TIMESTAMPS:00:35 Andrew's background and Assent's growth journey02:37 The scale: 18,000 suppliers, 200 compliance topics05:07 The post-ChatGPT transformation and Vista Equity OKRs06:09 Early adoption of GitHub Copilot & ChatGPT Enterprise08:51 Trip report improvements using AI synthesis09:35 Generating synthetic bills of materials for safe testing12:26 Where AI drives efficiency: entity resolution, part matching, document validation13:12 Measuring AI's impact: productivity, quality, and profitability17:32 Expanding customer success capacity without adding headcount20:37 How to drive company-wide AI adoption (hackathons, Slack, evangelists)24:10 Andrew's personal AI workflows & deep research routinesTOOLS & RESOURCES MENTIONED:AI Tools & PlatformsGitHub Copilot (Microsoft) → adopted early for engineeringChatGPT (OpenAI, including Enterprise license) → used across teams for synthesis, rewriting, summarizationPerplexity AI (Pro) → used for deep research reportsInternal AI Use Cases & SystemsSynthetic bills of materials → generated using AI to safely test software without exposing sensitive customer dataAutomated document review → handling millions of supplier documents for complianceEntity resolution → using AI to match the right supplier or part across massive datasetsPart resolution & document validation → automating complex checks in the supply chainCompany-Wide AI Adoption Tools & MethodsOKRs (Objectives & Key Results) → embedded AI goals at company, team, and functional levelsAI hackathons → internal competitions to inspire creative use casesSlack channels → for sharing, evangelizing, and discussing AI applications internallyPersonal CEO Tools & WorkflowsPerplexity deep research → running 12–15 deep research reports per dayAI summarization & rewriting → e.g., turning multi-page trip reports into professional one-page summaries
Paul Burani is the Founder and Chief Revenue Officer of Mission Flywheel, a consultancy that empowers mission-driven organizations to scale revenue through data-driven strategies and measurable social impact. His career spans over two decades, including leadership roles at Google and in the edtech sector, where he focused on workforce development and economic inclusion. Paul's expertise aligns business growth with social outcomes, helping clients in sectors like climate, education, and healthcare prove their impact to investors and stakeholders. Through Mission Flywheel, he supports purpose-driven ventures in building sustainable, high-performing revenue models. In this episode… Scaling a business is never a straight line — especially when growth hinges on aligning a company's mission with its revenue strategy. Many leaders struggle to build sustainable momentum without compromising their core values or burning through capital. How can growth-stage companies maintain velocity while staying true to their purpose? Paul Burani, a seasoned revenue strategist and fractional CRO, offers a blueprint for achieving capital-efficient growth rooted in clarity, data, and customer-centricity. He recommends starting with a clear articulation of the core problem and then layering on insights from data — whether from existing operations or direct customer research. He emphasizes the power of using data to optimize internal decisions and create feedback loops that fuel continuous momentum. Paul also discusses how transparent OKRs and cross-functional collaboration can replace rigid funnels with resilient flywheels. In this episode of the Inspired Insider Podcast, Dr. Jeremy Weisz interviews Paul Burani, Founder and Chief Revenue Officer at Mission Flywheel, about data-driven growth strategies for mission-led companies. Paul discusses the flywheel model, transitioning from startup to scale, and how to unlock customer insights. He also shares lessons from Google, approaches to managing high performers, and his thoughts on building work cultures rooted in purpose.