The Right-Hand Roadmap

Follow The Right-Hand Roadmap
Share on
Copy link to clipboard

The Right-Hand Roadmap is the only podcast for Seconds-In-Command of founder-led companies. I'm your host Megan Long, an award-winning executive & entrepreneur, pro athlete, and owner of Second First. Together we explore the unique world of being a #2 Leader in entrepreneurial companies. This is the place where we dive into the challenges, opportunities, and strategies that can help you excel in your role. Our mission is clear: to transform the relationships between entrepreneurs and, you, their Second-In-Command. We'll cover a wide range of topics, from navigating your relationship with the founder to mastering the role through best practice knowledge, tools, and insights you need to thrive in your position. But this podcast isn't just about learning; it's also about being part of a community. This role is lonely and often misunderstood - together we're stronger and supported in ways we can't find within our companies or at home. If you're ready to embark on a journey of growth, learning, and empowerment as a Second-In-Command, then make sure to subscribe to The Right-Hand Roadmap podcast. We can't wait to have you as part of our community, and we look forward to helping you become the force multiplier your company needs.

Megan Long


    • May 13, 2025 LATEST EPISODE
    • every other week NEW EPISODES
    • 12m AVG DURATION
    • 50 EPISODES


    Search for episodes from The Right-Hand Roadmap with a specific topic:

    Latest episodes from The Right-Hand Roadmap

    #50: Fifty Things I Wish I Knew as a COO (Rapid Fire)

    Play Episode Listen Later May 13, 2025 7:29


    50 Lessons for 50 Episodes In this special 50th episode, host Megan Long reflects on the hard-won wisdom gathered from years of working as (and with) Seconds-In-Command at founder-led companies. She shares 50 rapid-fire lessons she wishes she could give her younger executive self, ranging from mindset shifts and leadership tactics to strategic guidance and personal boundaries. If you're navigating the complex and rewarding role of COO or integrator, this episode will speak directly to your experience.   Rate, review & follow on Apple Podcasts Click Here to Listen! OR WATCH ON YOUTUBE If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode. Links mentioned in the episode: Second First Membership Second First One-on-One Coaching Second First on Instagram Second First on LinkedIn Megan Long on LinkedIn

    #49: The Lead-Gen Blueprint for SMBs & Perfecting an Outsourcing Partnership with Cindy Dodd

    Play Episode Listen Later May 1, 2025 27:41


    Scaling Smarter: What Every COO Needs to Know About Lead Gen In this episode, Megan Long interviews Cindy Dodd, the powerhouse COO and cofounder of PEMA.io, an Inc. 5000 B2B appointment-setting firm. Cindy breaks down the most common lead generation mistakes, shares how to hold outsourced vendors accountable, and reveals the revenue planning process that helps her team scale with confidence. Whether you're managing a sales team, overseeing growth initiatives, or just trying to help your CEO hit ambitious targets, Cindy delivers clear, practical advice every Second-In-Command needs to hear. You'll hear all about: 02:07 – How PEMA.io helps entrepreneurial businesses 03:08 – The biggest mistake entrepreneurial companies make with lead gen 04:52 – What to do when you've been placed over sales with no sales experience 05:26 – The difference between delegation and abdication 06:00 – How to get ROI from outsourced marketing and sales partners 07:20 – How to vet lead gen vendors (hint: demand proof, not promises) 08:24 – The importance of aligning expectations with partners 09:12 – Leading vs. lagging indicators in outbound sales 10:28 – Lessons learned from client delivery and expectation management 12:11 – Why having a strong internal sales process is critical for outsourced partnerships 14:04 – What COOs should focus on to scale their business in 2025 16:12 – How to set realistic revenue goals based on data (not CEO wishes) 18:33 – Why quarterly reviews with your sales team help spot and replicate what's working 19:51 – Cindy's backstory: from Johannesburg to asset management to entrepreneurship 21:57 – The ups and downs of cofounding a business with your spouse 23:52 – Sneak peek at Cindy's expert session for Second First members 25:29 – Where to find Cindy online and get her free resources 26:14 – Free downloads: Outbound Sales Playbook & LinkedIn Guide   Rate, review & follow on Apple Podcasts Click Here to Listen! OR WATCH ON YOUTUBE If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode. Links mentioned in the episode: FREE Outbound Sales Playbook PEMA.io website Cindy Dodd's website The Takeover Podcast Cindy Dodd's Instagram Cindy Dodd's LinkedIn Second First Membership Second First One-on-One Coaching Second First on Instagram Second First on LinkedIn Megan Long on LinkedIn

    #48: De-Risking the Business as a Second-In-Command

    Play Episode Listen Later Apr 22, 2025 9:45


    Protect the business and your team by identifying and eliminating risk before it derails your growth. One of the most powerful (and often invisible) things you can do in this role is proactively de-risk the business. That means thinking ahead, planning for disruptions, and removing single points of failure that could knock the business off track. In this episode of The Right-Hand Roadmap, we unpack the real meaning of de-risking. It's not about fear—it's about responsibility. We talk through how to evaluate operational systems, vendor dependencies, leadership bandwidth, and revenue streams with fresh eyes. Megan also shares a true story from a tornado that tested her own continuity plans, and an ADA compliance issue that could've quietly cost $20,000 if not addressed. You'll hear all about: 00:28 – Why de-risking is a critical function for Seconds-in-Command in founder-led companies 01:03 – The three core priorities you must balance: growth, team health, and risk mitigation 01:33 – Understanding key person risk: what happens if the CEO—or you—can't work? 02:01 – The value of cross-training, documentation, and succession planning 02:22 – Operational risk: how to spot single points of failure in systems and processes 02:47 – A business continuity exercise that lists every function, tool, and backup plan 03:32 – The real-life value of this work: how a tornado in 2020 tested their contingency planning 04:17 – Payroll goes down? Here's a backup plan that ensures no one misses a paycheck 05:01 – Strategic and financial risk: are you too reliant on one client, channel, or product? 05:51 – Vendor risk: how to evaluate suppliers and what to do when terms change unexpectedly 06:16 – The two-part vendor checklist: security protocols and financial terms 07:25 – How to approach worst-case scenario thinking without being a fearmonger 07:48 – Pitching risk-mitigation to your CEO: making it real with examples 08:00 – A real ADA website lawsuit story—and why a $20K surprise could derail your year 09:14 – Use storytelling and real-life examples to prioritize de-risking in your annual plan   Rate, review & follow on Apple Podcasts Click Here to Listen! OR WATCH ON YOUTUBE If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode. Links mentioned in the episode: Second First Membership Second First One-on-One Coaching Second First on Instagram Second First on LinkedIn Megan Long on LinkedIn

    #47. Financial Planning for Six-Figure Earners & Compensation Plan Pitfalls with Brenton Harrison

    Play Episode Listen Later Apr 8, 2025 30:22


    Avoid the Hidden Traps in Your Compensation Plan and Financial Planning as a Six-Figure Earner. In episode 47 of The Right-Hand Roadmap, we sat down with Brenton Harrison, a Certified Financial Planner who specializes in helping first- and second-generation high-income earners. Brenton pulls back the curtain on the emotional baggage that often comes with financial success, and how easy it is to fall into the trap of compensation plans that sound good on paper but leave you over-leveraged, underpaid, or misinformed. This episode is a must-listen if you've ever second-guessed your bonus structure, wondered whether equity is really worth it, or felt embarrassed not knowing what questions to ask about financial planning. Brenton's insights will challenge how you think about money, and give you the tools to build a smarter, more sustainable financial future. You'll hear all about: 00:41 – Meet Brenton Harrison: Financial planner for first- and second-generation high earners 02:25 – Why Brenton launched New Money, New Problems and the emotional baggage behind financial success 05:40 – The blind spots of compensation plans for seconds-in-command 07:55 – Why “you should be thankful” is a red flag in any compensation conversation 10:32 – When commissions and bonuses are more about control than reward 14:47 – How to recognize a toxic comp plan 17:10 – Planning for income that fluctuates (like commission-based roles) 21:18 – Should you accept equity? What questions to ask first 25:00 – The “six-figure lifestyle” trap 27:36 – How high earners can build a financial strategy that's actually sustainable 30:41 – Why your net worth matters more than your income 32:19 – Tips for COOs navigating equity, risk, and career growth 36:03 – When to hire a financial planner—and what to look for 38:45 – Brenton's advice for COOs in fast-growing companies   Rate, review & follow on Apple Podcasts Click Here to Listen! OR WATCH ON YOUTUBE If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode. Links mentioned in the episode: New Money, New Problems website Brenton D. Harrison's Instagram  New Money, New Problems Podcast Second First Membership Second First One-on-One Coaching Second First on Instagram Second First on LinkedIn Megan Long on LinkedIn

    #46: Employee-Generated Content & How to Start Building a Personal Brand Online

    Play Episode Listen Later Apr 3, 2025 8:07


    Encouraging employee-generated content and building a personal brand on LinkedIn can position your company and team as industry leaders (while also making hiring easier than ever). In today's episode of The Right-Hand Roadmap, we're diving into employee-generated content (EGC) and why it's one of the most powerful tools for attracting top talent and building a strong company presence. We'll also explore why Seconds-in-Command should start developing their own personal brand online, separate from their company. You'll learn how to leverage LinkedIn without feeling cringey, encourage your team to become thought leaders, and strategically position yourself as an expert in your industry. You'll hear all about: 00:29 – Introduction to employee-generated content and personal branding 00:41 – What is UGC (user-generated content) and how does it apply to companies? 01:08 – Two main types of UGC and how brands use it 02:13 – Applying the UGC concept to your employees and company 02:49 – Why the fear of employees posting too much on LinkedIn is outdated 02:55 – The benefits of encouraging your employees to post online 03:02 – How thought leadership from your team strengthens sales and hiring 03:49 – How to help employees start posting on LinkedIn 04:45 – Why Seconds-in-Command need to build a personal brand separate from their company 05:06 – Your company is a rented brand—so it's critical to establish your own reputation 05:43 – Boz Saint John as an example of a strong personal brand 06:21 – Practical first steps for building your LinkedIn presence 07:12 – Your personal brand is more than just LinkedIn—it's the unique value others expect from you   Rate, review & follow on Apple Podcasts Click Here to Listen! OR WATCH ON YOUTUBE If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode. Links mentioned in the episode: Second First Membership Second First One-on-One Coaching Second First on Instagram Second First on LinkedIn Megan Long on LinkedIn

    #45: Q&A: Early Stage Priorities, Scaling in Anticipation of Growth, and Employees That Just Don't Care

    Play Episode Listen Later Mar 27, 2025 19:53


    Get practical answers to questions COOs are asking—about SOPs, staffing ahead of growth, and managing disengaged employees. In this Q&A episode of The Right-Hand Roadmap, Megan Long tackles real-world questions from second-in-command leaders navigating fast growth, resource constraints, and team dynamics. Whether you're wondering when to systematize your startup, how to staff for a 30% growth forecast, or what to do with employees who are just clocking in and out, this episode has guidance you can apply immediately. Megan draws on years of experience working inside and alongside founder-led businesses to help you set smart priorities and avoid common missteps. You'll hear all about: 00:00 – Introduction to the Q&A format and how to submit your own questions 01:47 – Q1: Prioritizing SOPs and processes at an early-stage company with ambitious growth goals 02:11 – Why sales and marketing systems must come before internal process-building 03:10 – Strategic planning example: focusing on partnerships and lead gen over documentation 04:08 – A warning: 300% growth will break your current systems—so build flexibly 05:08 – Story: Megan's mistake of over-documenting accounting procedures too early 06:47 – Challenge your CEO on whether SOPs are the most urgent need right now 07:08 – Q2: Should you staff up in anticipation of growth or wait until overwhelmed? 08:16 – The cultural and operational risks of premature hiring 08:46 – Megan's rule of thumb: distinguish between proven vs. unproven growth 09:04 – Second First benchmarking data: turnover and revenue trends across members 10:07 – Forecasting in the post-2020 era: why historical data can be misleading Rate, review & follow on Apple Podcasts Click Here to Listen! OR WATCH ON YOUTUBE If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode. Links mentioned in the episode: Second First Membership Second First One-on-One Coaching Second First on Instagram Second First on LinkedIn Megan Long on LinkedIn

    #44: Keep It Brief: Conciseness Is an Essential Leadership Skill

    Play Episode Listen Later Mar 18, 2025 5:45


    Want your CEO to actually read your emails? Master the art of concise communication. As a COO or second-in-command, you don't have time for long-winded explanation, and neither does your CEO. In this episode of The Right-Hand Roadmap, Megan Long shares why brevity is an essential leadership skill in founder-led companies. You'll hear real-life examples of communication failures and learn how to craft messages that get read (and acted on). If you've ever written a detailed email that went ignored, this episode is for you. You'll hear all about: 00:28 – Why conciseness is a must-have leadership skill 00:40 – A real-world example: The director with PhD-level emails 01:36 – The manager whose messages were unreadable walls of text 02:32 – Have you ever written an email that was ignored? Here's why. 02:53 – The #1 rule of communicating with CEOs: Get to the point 03:05 – The power of clarity: Trial lawyers and plain English 03:28 – How to write emails your CEO will actually read 03:35 – Start with an executive summary (2-4 sentences) 03:47 – Use bullet points for key facts 03:58 – Cut the fluff: Eliminate filler words and phrases 04:39 – The golden rule: Give CEOs access to supporting details, but don't make them hunt for the key takeaways Rate, review & follow on Apple Podcasts Click Here to Listen! OR WATCH ON YOUTUBE If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode. Links mentioned in the episode: Second First Membership Second First One-on-One Coaching Second First on Instagram Second First on LinkedIn Megan Long on LinkedIn

    #43: Quarterly Planning Prework

    Play Episode Listen Later Mar 4, 2025 8:51


    Prepare for quarterly planning with a structured prework process that ensures alignment, clarity, and execution for your leadership team. Quarterly planning isn't just about setting goals—it's about ensuring your company is focused, aligned, and equipped to execute effectively. In this episode, Megan Long breaks down the essential prework every second-in-command should complete before heading into a quarterly planning session. From reviewing financials to aligning with your CEO, these steps will help you walk into the room prepared, confident, and ready to lead a productive strategy meeting. You'll hear all about: 00:28 – The purpose of quarterly planning: alignment, focus, and execution 00:36 – The impact of preparation on a successful planning session 01:15 – Review last quarter's results 01:56 – Evaluate last quarter's rocks (goals) 02:47 – Review key business metrics and trends 03:17 – Meet with department heads 04:32 – Personal pre-planning session 05:19 – Align with your CEO   Rate, review & follow on Apple Podcasts Click Here to Listen! OR WATCH ON YOUTUBE If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode. Links mentioned in the episode: Second First Membership Second First One-on-One Coaching Second First on Instagram Second First on LinkedIn Megan Long on LinkedIn

    #42: Being Second-In-Command to Your Spouse & How to Win in Family and Business with "Chief Matriarch" Amy Stasiukaitis

    Play Episode Listen Later Feb 25, 2025 33:38


    Secrets to success being a Second-In-Command to your spouse while balancing business and family life with Amy Stasiukaitis, Chief of Staff at Low County Case & Millwork and founder of The Helm. Being a second-in-command in any business is a challenge, but when your CEO is also your spouse, the dynamics become even more complex. In Episode 42 of The Right-Hand Roadmap, we sat down with Amy Stasiukaitis, Chief of Staff at Low County Case & Millwork and founder of The Helm, to discuss what it takes to balance leadership, marriage, and motherhood. Amy also shared how she carved out her role as “Chief Matriarch” in a growing company, managing operations while supporting her husband's vision. You'll hear all about: 02:15 – Amy's background and how she became the Chief of Staff at Low County Case & Millwork and “Chief Matriarch” in life as a whole. 05:30 – Defining the role of a Second-In-Command in a family-run business 09:45 – The biggest challenges of working with a spouse and how to navigate them 14:10 – The benefits of setting boundaries, or not setting boundaries! 19:30 – Why communication is the key to success in business and marriage 23:50 – The importance of trust between the entrepreneur and Second-In-Command 27:40 – How Amy's experience led her to create The Helm and share her expertise with other Second First members. 32:15 – Advice for anyone stepping into a leadership role alongside their spouse Rate, review & follow on Apple Podcasts Click Here to Listen! OR WATCH ON YOUTUBE If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode. Links mentioned in the episode:   Chief Matriarch - Amy's Website Low County Case & Millwork Second First Membership Second First on Instagram Second First on LinkedIn Megan Long on LinkedIn Amy Stasiukaitis on LinkedIn Amy Stasiukaitis on Instagram

    #41: EA vs. Chief of Staff vs. COO & Maximizing the Partnership with Founders with Hallie Warner

    Play Episode Listen Later Feb 18, 2025 38:22


    Learn the key differences between an Executive Assistant, Chief of Staff, and COO, and how to maximize your partnership with a founder, featuring expert insights from Hallie Warner. In this episode of The Right-Hand Roadmap, we dive deep into the evolving roles of Executive Assistants, Chiefs of Staff, and COOs with Hallie Warner, founder of The Founder & The Force Multiplier. Hallie shares her expert perspective on how each role serves a founder differently, what makes for a successful right-hand partnership, and when it's time to level up. If you're a COO, EA, or Chief of Staff (or you're thinking about hiring one) this episode will give you a clear roadmap to making that partnership thrive. You'll hear all about: 03:12 - The distinct roles of an Executive Assistant, Chief of Staff, and COO—and how they evolve over time 08:45 - How a founder's needs dictate the right-hand role they should hire for 12:30 - The biggest misconceptions about EAs, Chiefs of Staff, and COOs 17:55 - What makes a right-hand partnership successful, from both the founder's and the operator's perspective 23:40 - When it's time for an EA to step into a Chief of Staff role—and when that might not be the right move 29:10 - Key skills that Chiefs of Staff and COOs need to develop for long-term success 34:50 - Hallie's advice for founders looking to hire their first right-hand Rate, review & follow on Apple Podcasts Click Here to Listen! OR WATCH ON YOUTUBE If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode. Links mentioned in the episode: The Founder & The Force Multiplier Second First Membership Second First on Instagram Second First on LinkedIn Megan Long on LinkedIn Hallie Warner on LinkedIn Hallie Warner on Instagram

    #40: Why Am I Becoming Less Confident Over Time?

    Play Episode Listen Later Feb 11, 2025 8:08


    Feeling less confident in your role as a Second-in-Command? Learn how the Dunning-Kruger effect impacts your leadership and how to overcome it. Ever feel like the more you learn, the less confident you become? You're not imagining it. This is the Dunning-Kruger effect at work. In this episode, we break down how this psychological phenomenon affects Seconds-in-Command and why gaining experience can sometimes feel like a confidence killer. Learn how to push past self-doubt, trust your expertise, and lead with confidence...even when you don't have all the answers. You'll hear all about: 01:11 – Why COOs and Integrators often feel less confident over time. 02:17 – The paradox: the more you know, the more you realize you don't know. 03:00 – Real-world examples from coaching engagements where confidence dips after deeper learning. 03:42 – Understanding "Mount Stupid"—why overconfidence is highest when knowledge is lowest. 04:11 – Three ways the Dunning-Kruger effect impacts Seconds-in-Command: 04:16 – Second-guessing decisions, even when you're the most qualified. 04:44 – Assuming the CEO has all the answers (hint: they don't). 05:22 – Holding back on leading boldly when your perspective is most needed. 06:03 – How to counteract self-doubt and embrace your role: 06:09 – Trust your expertise and recognize self-awareness as a strength. 06:32 – Assert yourself with confidence—your CEO needs your input. 07:34 – Embrace continuous learning, but don't let it paralyze you.   Rate, review & follow on Apple Podcasts Click Here to Listen! OR WATCH ON YOUTUBE If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode. Links mentioned in the episode: The Dunning-Kruger Effect Second First Membership Second First One-on-One Coaching Second First on Instagram Second First on LinkedIn Megan Long on LinkedIn

    #39: Strategic Networking as an Executive: Making Your Dream Connections

    Play Episode Listen Later Feb 4, 2025 13:27


    Want to connect with top industry leaders and expand your executive network? Learn how to make high-impact connections and build relationships that open doors. As an executive, your network is one of your greatest assets. In this episode of The Right-Hand Roadmap, we dive into the art of strategic networking: how to connect with key industry leaders, build meaningful professional relationships, and leverage those connections to grow in your role. Megan Long shares actionable strategies for getting in front of decision-makers, breaking into exclusive circles, and maximizing networking opportunities at events. Whether you're looking for mentorship, new opportunities, or simply a stronger support system, this episode will help you make the right connections. You'll hear all about: 00:48 – Why networking matters for executives and leaders, not just entrepreneurs 03:05 – The importance of owning your network and making your value transferable 03:58 – The power of bold introductions: How a simple conversation led to a career-changing internship 06:05 – The art of networking with high-profile individuals (without being awkward or pushy) 07:25 – The “one-degree separation” strategy: Using mutual connections to get introductions 08:14 – Leveraging conferences and events to meet industry leaders 09:14 – How to maximize company sponsorships to access exclusive networking opportunities 10:18 – The key to effective follow-ups and making connections stick Rate, review & follow on Apple Podcasts Click Here to Listen! OR WATCH ON YOUTUBE If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode. Links mentioned in the episode: Second First Membership Second First on Instagram Second First on LinkedIn Megan Long on LinkedIn

    #38: Gain 20% of Employee Time Back & Manage "Digital Chaos" with Shawn Lemon

    Play Episode Listen Later Jan 28, 2025 35:10


    Discover how to reclaim 20% of your team's time and master your digital tools with Shawn Lemon, founder of The Digital Organizer. In this episode of The Right-Hand Roadmap, we sit down with Shawn Lemon, founder of The Digital Organizer, to tackle the hidden costs of "digital chaos" in your organization. Shawn shares practical strategies for optimizing digital tools, streamlining workflows, and reclaiming 20% of your employees' time. Whether you're drowning in a sea of Slack messages, struggling to find that elusive Google Doc, or wondering how to finally implement efficient systems, this conversation is packed with actionable insights you can start using today. You'll hear all about: 01:20 – Introduction to Shawn Lemon and The Digital Organizer: Shawn explains his mission to help companies escape “digital chaos.” 03:45 – Identifying "digital chaos": Common signs your organization is losing efficiency due to poor digital organization. 06:15 – Reclaiming 20% of employee time: How systematizing your tools and workflows can unlock hours of productivity. 08:50 – Essential tools for digital organization: Shawn's go-to platforms and why less is more when it comes to tech. 11:10 – Email mastery: Tips for managing overflowing inboxes and setting boundaries. 13:30 – Overcoming resistance to change: How to get buy-in from your team to adopt new systems. 16:00 – The power of a "single source of truth": Why a centralized platform is the foundation of digital clarity. 19:40 – Real-world examples: Stories of teams who regained control and boosted productivity through Shawn's methods. 22:15 – Quick wins: Immediate steps you can take today to reduce digital clutter. 25:00 – Closing thoughts: Shawn's advice for sustaining long-term digital organization. Rate, review & follow on Apple Podcasts Click Here to Listen! OR WATCH ON YOUTUBE If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode. Links mentioned in the episode: Download Your Free Guide from The Digital Organizer The Digital Organizer Website Second First Membership Second First on Instagram Second First on LinkedIn Megan Long on LinkedIn Shawn Lemon on LinkedIn The Digital Organizer on LinkedIn The Digital Organizer on Instagram

    #37: Three Phrases to Add to Your Toolbox

    Play Episode Listen Later Jan 21, 2025 6:38


    Simple yet powerful phrases to elevate your leadership, empower your team, and reclaim your time. In this episode, host Megan Long shares three essential phrases every COO or second-in-command should master. These tools are designed to grow your team's problem-solving skills, build trust with your CEO, and help you maintain focus by avoiding unnecessary urgency. You'll hear all about: 00:29 – Introduction to the episode: three phrases to add to your leadership toolbox. 01:01 – Phrase 1: “What do you suggest?” — Empower your team to think critically and solve their own problems, boosting their confidence and decision-making muscles. 02:10 – Benefits of using “What do you suggest?” for your team's growth and your freedom as a leader. 03:05 – Phrase 2: “How do you feel about that?” — Gain insight into your team's and CEO's perspectives while strengthening trust and connection. 04:13 – How asking your CEO this question enhances your partnership and provides a deeper understanding of their thought process. 04:29 – Phrase 3: “When do you need an answer by?” — A strategy for managing decision-making pressure and prioritizing effectively. 05:52 – The hidden benefit of teaching your team the difference between urgency and importance.   Rate, review & follow on Apple Podcasts Click Here to Listen! OR WATCH ON YOUTUBE If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode. Links mentioned in the episode: “Who's Got the Monkey?” by Harvard Business Review Second First Membership Second First One-on-One Coaching Second First on Instagram Second First on LinkedIn Megan Long on LinkedIn

    #36: Set Accurate Revenue Goals

    Play Episode Listen Later Jan 14, 2025 8:47


    Set realistic revenue goals for the year and create a strategic plan to hit them. In this episode, Megan Long breaks down the process of setting accurate revenue goals for your business. If you're tired of arbitrary revenue targets, this episode will teach you how to evaluate your sales funnel, crunch the numbers, and build a clear path to success. Whether you're a COO or second-in-command, this episode gives you actionable steps to help your company achieve its financial targets—and even exceed them. You'll hear all about: 00:28 – The common pitfall: arbitrary revenue targets set by CEOs without sufficient planning. 01:20 – The importance of working backward to assess team capacity and realistic targets. 01:55 – Megan introduces the downloadable worksheet to guide listeners through the exercise. 02:12 – Start by analyzing your sales funnel and collecting five key data points. 03:36 – Calculating average deal size using historical sales data. 04:14 – Breaking down an example sales funnel with clear metrics and close rates. 05:45 – How to calculate your company's revenue capacity based on your sales funnel. 06:17 – Adjusting team capacity or hiring needs to meet ambitious revenue goals. 07:26 – Evaluating individual salesperson capacity to handle increased quotas. 08:12 – Using sales funnel math to communicate actionable plans to your CEO.   Rate, review & follow on Apple Podcasts Click Here to Listen! OR WATCH ON YOUTUBE If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode. Links mentioned in the episode: Second First Membership Second First One-on-One Coaching Second First on Instagram Second First on LinkedIn Megan Long on LinkedIn

    #35: Building a Professional Membership

    Play Episode Listen Later Jan 7, 2025 11:58


    Discover how Second First designed and launched a membership model for COOs and Seconds-in-Command. In this behind-the-scenes episode, Megan Long pulls back the curtain on creating a professional membership program tailored for Seconds-in-Command of founder-led businesses. Learn how Second First transformed their mastermind events into a dynamic, year-round membership with curated cohorts, expert workshops, and a user-friendly online platform. Megan shares the challenges, decisions, and strategies that brought this vision to life. You'll hear all about: 01:04 - The inspiration: a Nashville mastermind event and the need for continuity. 01:51 - Transitioning from one-off events to a year-round membership. 02:14 - Three key projects: pricing structure, value proposition, and building an online platform. 02:35 - Designing the revenue model for affordability and predictability. 03:48 - Why monthly dues include the in-person event to simplify budgeting. 05:00 - Shifting from project-based revenue to recurring revenue for stability. 05:13 - Crafting value: small mastermind cohorts for accountability and growth. 05:52 - Added perks: tools, templates, expert sessions, and a member directory for connections. 09:00 - Choosing Circle as the membership platform for its intuitive design.   Rate, review & follow on Apple Podcasts Click Here to Listen! OR WATCH ON YOUTUBE If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode. Links mentioned in the episode: Second First Membership Second First on Instagram Second First on LinkedIn Megan Long on LinkedIn

    #34: Five Gifts I Gave Myself This Year

    Play Episode Listen Later Dec 31, 2024 10:04


    Five "gifts" that are impactful ways to prioritize yourself and your growth in 2025. As the year winds down, we often focus on giving to others—but at Second First, we also encourage our community to invest in themselves. That's why we're excited to share the final episode of 2024, where we dive into five intentional gifts Megan Long gave herself this year. Each one represents a commitment to self-care, growth, and setting up for success in 2025. You'll hear all about: 01:25 - The first gift: Pre-scheduled "choice days" for rest, focus, or catch-up time. 02:52 - The second gift: A "personal profile" setting on her phone to limit work-related notifications. 03:32 - The third gift: A premium subscription to the Finch app for gamified self-care and productivity. 05:47 - The fourth gift: The "10 Things to Be True" exercise for visualization and goal-setting. 07:16 - The fifth gift: Three new professional memberships for growth and accountability in 2025. 08:46 - Reflections on the first year of The Right-Hand Roadmap podcast and what's to come in 2025.   Rate, review & follow on Apple Podcasts Click Here to Listen! OR WATCH ON YOUTUBE If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode. Links mentioned in the episode: Finch App Second First Membership Second First on Instagram Second First on LinkedIn Megan Long on LinkedIn

    #33: REPLAY: Unlock the Power of Your Second-In-Command Webinar

    Play Episode Listen Later Dec 3, 2024 20:14


    Use the Three C's to unlock the COO's superpowers. In this special replay of a webinar presented to the Entrepreneur's Organization, Megan Long unpacks how to use the Three C's: Communication, Coaching, and Community, to unlock the power of a strong Second-In-Command. Whether you're a founder looking to level-up your leadership team or a Second-in- Command seeking growth, you'll gain actionable insights and real-world examples from Megan's presentation. You'll hear all about: 02:15 - Common challenges founders face when scaling their businesses. 05:30 - The strategic role of a second-in-command in bridging vision and execution. 08:45 - How to assess whether your business is ready for a COO. 12:00 - Characteristics of a successful founder-COO partnership. 15:30 - Real-world examples of founder-second-in-command dynamics in action. 18:45 - Megan's top strategies for empowering your second-in-command to drive results.   Rate, review & follow on Apple Podcasts Click Here to Listen! OR WATCH ON YOUTUBE If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode. Links mentioned in the episode: Second First Membership Second First on Instagram Second First on LinkedIn Megan Long on LinkedIn

    #32: Q&A: Measuring Your Success, Hiring a Second-In-Command, & Favorite Apps

    Play Episode Listen Later Nov 26, 2024 10:03


    Answering your questions about measuring success, hiring a second-in-command, and the best tools to streamline operations. Feeling stuck in your role as a Second-In-Command? You've climbed as high as the org chart allows, achieved the “top” title in your company, and yet, the hunger for growth remains. In this episode, Megan Long dives into the unique challenges COOs and other seconds-in-command face when they've reached the top of the org chart in entrepreneurial businesses. You'll hear all about: 00:28 – Listener Q&A kicks off! Learn how to submit your questions for future episodes. 01:28 – Question 1: How do I measure my success as an integrator? 04:32 – Question 2: What advice do you have for hiring a second-in-command? 07:29 – Question 3: What's your top recommended tool or software? 09:33 – Closing thoughts: Submit your questions, find show notes, and subscribe to stay in the loop!   Rate, review & follow on Apple Podcasts Click Here to Listen! OR WATCH ON YOUTUBE If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode. Links mentioned in the episode: Microsoft Loop Blog Post Second First Membership Second First on Instagram Second First on LinkedIn Megan Long on LinkedIn

    #31: What To Do When You've Hit Your Ceiling

    Play Episode Listen Later Nov 19, 2024 7:21


    Break through your ceiling and reignite growth as a Second-In-Command. Feeling stuck in your role as a Second-In-Command? You've climbed as high as the org chart allows, achieved the “top” title in your company, and yet, the hunger for growth remains. In this episode, Megan Long dives into the unique challenges COOs and other seconds-in-command face when they've reached the top of the org chart in entrepreneurial businesses. You'll hear all about: 00:38 – Why feeling "stuck" happens in entrepreneurial businesses and how flat hierarchies can limit traditional career advancement. 01:00 – Reframing career growth: shifting from climbing the ladder to expanding your scope. 02:02 – The lifecycle of a second-in-command: tactical beginnings to strategic partnerships. 02:45 – Transitioning from being in the weeds to coaching and mentoring your team. 03:11 – The strategic shift to organizational development and long-term planning. 04:08 – Becoming a thought partner to your CEO and taking ownership of new initiatives. 04:42 – Ways to upskill: hiring a coach, consuming high-quality resources, and joining peer groups. 05:21 – The value of structured training and small group masterminds like Second First's membership program. 05:27 – Collaborating with your CEO through offsite discussions for personal and professional alignment. 06:08 – Developing external influence by positioning yourself as a thought leader and expanding your network.   Rate, review & follow on Apple Podcasts Click Here to Listen! OR WATCH ON YOUTUBE If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode. Links mentioned in the episode: Second First Membership Second First on Instagram Second First on LinkedIn Megan Long on LinkedIn

    #30: My Story & the Origin of Second First

    Play Episode Listen Later Nov 12, 2024 14:14


    The personal journey behind Second First's origin and how COO support systems changed everything. At Second First, we know that being a second-in-command in a founder-led business can feel both rewarding and isolating. Our CEO, Megan Long, knows firsthand the weight of responsibility that comes with such a role, and in our latest episode of The Right-Hand Roadmap, she opens up about her personal journey to building Second First as a haven for others in her shoes. Megan's story is one of resilience, perseverance, and a commitment to helping COOs, Directors of Operations, and Seconds-In-Command feel less alone. In 2020, facing everything from natural disasters to a pandemic, she realized how crucial it was to have a peer network that truly understood her role's pressures. It was this experience—navigating uncharted waters with no place to turn—that sparked the creation of Second First. We wanted to build something more than a coaching framework; we wanted a community that lifts up each other through the toughest challenges. If you've ever felt like no one understands the demands of being the "number two," tune in to hear the personal story that launched Second First and why we're dedicated to building a strong, supportive community for second-in-command leaders. You'll hear all about: 00:36 - Megan shares why she hesitated to tell her full story and discusses her gratitude for past mentors. 01:16 - Reflecting on the career experiences that shaped her perspective as a young entrepreneur and woman in leadership. 02:02 - Introduction to Megan Long and the founding of Second First. 02:46 - Background as a CPA and rise to COO in a founder-led company. 03:06 - Realizing the gap in professional development and peer support for seconds-in-command. 03:18 - Building a coaching framework for the second-in-command role. 05:15 - 2020 brings unexpected challenges: tornado, pandemic, and more. 06:13 - Leading the company through crisis: disaster response and financial adaptations. 07:28 - The pressure and personal isolation of crisis leadership. 08:18 - Facing depression and how it spurred her to seek support and start Second First. 10:10 - Founding Second First to prevent other seconds-in-command from feeling isolated. 11:32 - The importance of peer support for seconds-in-command and Second First's mission. 13:28 - Highlighting member feedback on the Second First community. 13:51 - Upcoming opportunity to join the Second First membership Rate, review & follow on Apple Podcasts Click Here to Listen! OR WATCH ON YOUTUBE If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode. Links mentioned in the episode: Second First Membership Second First on Instagram Second First on LinkedIn Megan Long on LinkedIn

    #29: AI Prompts to Make Your Life Easier as a COO

    Play Episode Listen Later Nov 5, 2024 12:06


    Use these powerful AI prompts to streamline your work as a COO and enhance productivity. In this episode of The Right-Hand Roadmap, we explore how ChatGPT and other AI tools can streamline various aspects of a COO's day-to-day responsibilities, from high-level strategic planning to task-focused productivity. Using the right AI prompts can save time and offer insights into decision-making without the need to open endless new applications or risk security issues. We highlight practical uses for ChatGPT, including prompts to speed up decision-making by generating quick risk assessments and pros/cons lists for new initiatives. COOs can also offload admin work, asking ChatGPT to create executive summaries or time-block their schedules. For those diving into quarterly or annual planning, the episode also covers AI's role in conducting trend analyses and drafting clear, concise presentations for team-wide meetings. You'll hear all about: 00:28 - Addressing AI fatigue and common use cases reported by business leaders. 01:06 - Security concerns with open AI models; lessons from Samsung's data incident. 01:53 - Open-source vs. closed-source AI and their implications. 02:35 - App fatigue and tips for discerning new AI apps. 04:08 - Introduction to Palo Alto Networks' "Applipedia" for assessing app security. 04:54 - Prompt 1: Speed up decision-making with AI-based risk analyses. 06:17 - Prompt 2: Boost productivity by leveraging AI for summarizing reports, time-blocking schedules, and creating checklists. 07:44 - AI use case for personal organization, such as creating a self-care plan or meal planning. 08:39 - Prompt 3: Utilize AI for strategic planning and trend analysis. 09:54 - Breaking down priorities or “rocks” with AI for a 90-day plan. 10:38 - Use AI to draft presentations for a State of the Company meeting. Rate, review & follow on Apple Podcasts Click Here to Listen! OR WATCH ON YOUTUBE If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode. Links mentioned in the episode: Palo Alto Networks' Applipedia Second First on Instagram Second First on LinkedIn Megan Long on LinkedIn

    #28: Staying Focused on the Big Picture

    Play Episode Listen Later Oct 29, 2024 6:04


    Learn six practical strategies to keep your focus on long-term success while managing daily demands. Being a COO or second-in-command in a founder-led company is no easy task. With so many day-to-day responsibilities, it's easy to lose sight of the bigger picture. That's why in this episode of The Right-Hand Roadmap, we focus on strategies that will help you stay aligned with your company's long-term vision while managing immediate needs. Listeners will gain insights on decision-making, setting priorities, and collaborating with other leaders, all while keeping the company's long-term vision in mind. You'll hear all about: 00:44 – First strategy: Will the solution work five years from now? 01:37 – Second strategy: Consider multiple perspectives within the organization. 02:16 – Third strategy: If a decision negatively affects one employee, does it benefit the rest of the team? 03:10 – Fourth strategy: Always focus on your "rocks" – the key priorities. 04:22 – Fifth strategy: Monthly big-picture meetings with the CEO. 05:04 – Sixth strategy: Create a list of 10 things you want to be true about the business in 10 years. Rate, review & follow on Apple Podcasts Click Here to Listen! OR WATCH ON YOUTUBE If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode. Links mentioned in the episode: The 7 Habits of Highly Effective People by Stephen Covey

    #27: Setting Boundaries with a CEO as their Second-In-Command

    Play Episode Listen Later Oct 22, 2024 7:08


    How to set boundaries with your CEO to create a productive and balanced work relationship. At Second First, we know that managing the delicate balance between supporting a visionary CEO and maintaining your own work-life harmony can be tricky for seconds-in-command. In this week's episode of The Right-Hand Roadmap, we focus on how to set clear, mutually beneficial boundaries that ensure you're delivering your best work while protecting your time. Boundaries are not about restricting access or flexibility. Rather, they're about creating clear expectations for how to achieve the best results in your role. We encourage COOs to think about what work-life fit looks like for them personally and what hours they expect to be available to their CEO. It's equally important to recognize your "sacred time" – moments that should remain completely off-limits, whether for family or personal rejuvenation. Today, Megan walks through practical steps to clarify expectations, navigate difficult conversations, and set yourself up for long-term success in your role, while still being available when it truly matters.   You'll hear all about: 00:44 – Framing boundaries as a way to enhance productivity, not limit flexibility. 01:35 – Get clear on what work-life balance or work-life fit looks like for you. 02:19 – Establishing expectations for availability between you and your CEO. 02:52 – The importance of setting boundaries to protect personal relationships. 03:17 – Creating agreements for handling communication outside of normal work hours. 03:40 – Identifying and protecting your "sacred time" where you are completely unavailable. 05:05 – Addressing misaligned tasks that don't fit with your natural abilities or goals. 06:00 – Commit to staying refreshed and recharged to perform at your best.   Rate, review & follow on Apple Podcasts Click Here to Listen! OR WATCH ON YOUTUBE If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode.

    #26: How To Create Your Perfect Schedule

    Play Episode Listen Later Oct 15, 2024 11:35


    Take control of your weeks by designing the perfect schedule. Today we dive into practical strategies for taking back control of your time by creating the perfect weekly schedule. A schedule that not only aligns with your priorities but also helps you minimize distractions, maximize productivity, and avoid burnout. The framework Megan Long discusses in this episode, is called the "Ideal Week", based on Todd Duncan's book Time Traps. By the end of the exercise, you'll walk away with a weekly schedule that includes all the essential activities -- team meetings, one-on-ones, and strategic work -- while also making room for personal development, self-care, and focus time. Once you've crafted this schedule, it's about sticking to it and protecting your time from last-minute disruptions. At the end of the episode, Megan also shares four of her favorite hacks to help you maintain control over your calendar (including how to avoid Sunday Scaries!) You'll hear all about: 00:32 – Avoid the trap of always being available. Constant distractions reduce your effectiveness. 01:10 – Protect your calendar—don't allow last-minute appointments or impromptu meetings. 01:55 – Introducing the ideal week framework from Todd Duncan's book, Time Traps. 02:18 – Step one: Identify your top “must-do” activities like team meetings, one-on-ones, and priority work. 03:03 – Step two: Identify the “want-to-do” activities like personal development or self-care. 03:45 – Fill out an ideal week template to map out your day-to-day activities, from meals to work priorities. 05:16 – Focus on revenue-producing and value-creating activities like client proposals. 06:04 – Hold yourself accountable to your ideal week by printing it out or using a digital calendar. 06:45 – Megan's top tips: 1) No meeting Mondays, 2) Group one-on-one meetings, 3) Block time for travel, 4) Leave protected blank space for deep work. Rate, review & follow on Apple Podcasts Click Here to Listen! OR WATCH ON YOUTUBE If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode. Links mentioned in the episode: Time Traps: Proven Strategies for Swamped Salespeople by Todd Duncan

    #25: My First Business & Unequal Partnerships

    Play Episode Listen Later Oct 8, 2024 7:33


    Lessons learned from a childhood business, and how they apply to partnerships as a Second-In-Command. In this episode of The Right-Hand Roadmap, we take a nostalgic trip down memory lane with Megan Long, as she shares the story of her very first business—Bodacious Beads—and the early lessons she learned about unequal partnerships. As a young entrepreneur making beaded jewelry with a childhood friend, Megan quickly realized that not all partners contribute equally. This experience, while playful at the time, echoed deeply in her later career as a COO. Many seconds-in-command know the feeling of carrying the bulk of the workload while the CEO enjoys the spotlight and reaps the rewards. Through this story, we encourage all second-in-commands to reflect on their roles and ask the tough questions: Are you fulfilled by the work you do? How can you reconcile your role to ensure it aligns with your personal goals? Tune in to hear how personal fulfillment plays a crucial role in long-lasting and successful partnerships. You'll hear all about: 00:40 – The story of Megan's first business, Bodacious Beads, which she started with a childhood friend, diving into early experiences of partnership dynamics. 02:20 – Megan describes the process of making jewelry and her unexpected realization when her partner contributed significantly less. 04:03 – The moment of truth arrives at a craft show when Megan notices the difference in effort between her and her friend, introducing her to the concept of unequal partnerships. 05:00 – Drawing parallels to her experience as a Second-In-Command, Megan explains the unequal work dynamics COOs can face when managing the day-to-day while the CEO enjoys the spotlight. 06:05 – She emphasizes the importance of finding personal fulfillment and alignment with career goals as a COO. Rate, review & follow on Apple Podcasts Click Here to Listen! Or Watch on Youtube If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode.

    #24: Take Your CEO/COO Partnership to the Next Level

    Play Episode Listen Later Oct 1, 2024 8:29


    Unlock the full potential of your CEO/COO partnership with communication, coaching, and community. We recently launched our Partnership Alignment Checkup, a quiz designed to help you understand where you stand in your CEO/COO relationship. Whether you're in lockstep with your CEO, have a solid foundation that needs improvement, or are struggling to align, this tool provides valuable insights to help you strengthen that bond. From there, we offer practical advice on improving communication, coaching each other for better clarity, and seeking community support from peers in similar roles. Together we cover the Three C's—the three key factors—communication, coaching, and community—that can take your partnership to the next level. You'll hear all about: 00:37 – How to assess your relationship with your CEO using the new "Partnership Alignment Checkup" quiz available on the Second First website. 01:16 – Possible outcomes from the quiz: You're either in lockstep, have a solid foundation with room for improvement, or need significant alignment. 01:58 – The role of the COO as a "force multiplier" and how the relationship with your CEO impacts your effectiveness. 02:26 – Introduction to the "Three C's" of improving your partnership: Communication, Coaching, and Community. 02:51 – Rapid-fire communication tips, including setting big-picture one-on-ones, creating a shared idea list, and documenting roles and responsibilities. 04:19 – Coaching: How repeating back what your CEO says can improve clarity and alignment. 05:06 – Understanding different priority systems and working together on what's urgent vs. important. 06:14 – Why exploring leadership and executive coaching can help bridge the gap between vision and execution. 06:44 – Community: The importance of having peers in your vertical and connecting with other seconds-in-command for support and insight. Rate, review & follow on Apple Podcasts Click Here to Listen! Or Watch on Youtube If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode. Links mentioned in the episode: Partnership Alignment Quiz

    #23: 2024 Second First Exchange Mastermind Recap

    Play Episode Listen Later Sep 24, 2024 12:04


    Wrap-up of the 2024 Second First Exchange mastermind for Seconds-In-Command. At Second First, we recently wrapped up our highly anticipated 2024 Second First Exchange mastermind in Nashville, Tennessee. It was an incredible experience, bringing together Second-In-Command leaders from across various industries for two days of in-depth learning, sharing, and connection. Megan shares key moments, takeaways, and the importance of creating a safe, yet valuable space for Seconds-In-Command to thrive. This mastermind wasn't just another business conference; it was a transformational experience where leaders left feeling heard, understood, and empowered. We're excited to bring even more value to the Second First Exchange in the coming months, so stay tuned for exciting updates! You'll hear all about: 00:28 - Recap of the Second First Exchange mastermind held in Nashville, Tennessee. 03:25 - Megan discusses the value of surrounding yourself with the right people and setting a positive, supportive tone for the cohort. 03:36 - Guest speaker Duane Marshall shared insights, and was impressed by the immediate camaraderie of the group. 05:30 - A recurring theme from attendees was the relief in finding peers who understood their unique challenges as seconds-in-command. 08:49 - Megan emphasizes the importance of curating the best experience and not taking the path of least resistance when organizing events. 09:58 - A member appreciated the balance between offering value and creating space for peer-to-peer learning, a key goal of the mastermind. 11:09 -Exciting changes to the Second First Exchange program will be announced in the coming months. Rate, review & follow on Apple Podcasts Click Here to Listen! Or Watch on Youtube If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode. Links mentioned in the episode: Second First on LinkedIn Second First website

    #22: Q&A: The Entrepreneur Stereotype, Must-Read Books, & Leadership Mishires

    Play Episode Listen Later Sep 17, 2024 10:38


    Navigating entrepreneurs that don't fit the stereotypes, reading recommendations, and the importance of a new leader's onboarding. In this quarter's Q&A episode of The Right-Hand Roadmap, we dive into the complexities that COOs and Seconds-In-Command often face when leading alongside non-traditional entrepreneurs. Not every CEO fits the visionary, fast-paced stereotype. We explore how to navigate these dynamics while still implementing the tools and strategies from Second First. Megan also shares three business books for any second-in-command looking to level up. These reads offer practical, no-nonsense advice on strategy, leadership, and client retention. Finally, we tackle a common leadership challenge—what to do when you've hired someone who isn't performing as expected. With strategies on how to reset expectations and establish a clear onboarding plan, this episode is a must-listen for any COO navigating similar leadership or strategic hurdles. You'll hear all about: 00:44 - How to submit a question for future episodes 01:40 - Question 1: What to do when your CEO is not a typical visionary? 02:40 - How some entrepreneurs are content with maintaining a lifestyle business 03:18 - The seven types of second-in-command roles, including "the other half" 04:03 - CEOs as technical experts who prefer not to lead marketing and sales 04:26 - Applying CEO-level strategies as a second-in-command 05:00 - Question 2: Three must-read business books 05:59 - Megan shares her thoughts on long business books and recommends 3 titles 08:02 - Question 3: How to handle a leadership misfire after hiring someone new 08:37 - Importance of creating a detailed 90-day onboarding plan 09:36 - Pitfalls of hiring new leaders without a plan 09:59 - How to hit the reset button and realign a new leader with a 60-day plan Rate, review & follow on Apple Podcasts Click Here to Listen! Or Watch on Youtube If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode. Links mentioned in the episode: No Bullshit Strategy by Alex M.H. Smith The Power of Moments by Chip and Dan Heath Never Lose a Customer Again by Joey Coleman The First 90 Days by Michael Watkins 2006 Harvard Business Review article: "Second in Command: The Misunderstood Role of the COO"

    #21: Make The Most of Q4: Finish The Year Strong

    Play Episode Listen Later Sep 10, 2024 7:50


    Use Q4 strategically to set your company up for a successful next year with practical tips on operations, talent, finance, and business development. As we enter the final stretch of the year, it's tempting to push through Q4 in a rush to hit annual goals. However, at Second First, we believe that Q4 is the perfect time to slow down, reflect on the year, and plan strategically for next year. By taking a thoughtful approach, you'll avoid feeling like you're behind when January arrives. In our latest podcast episode, we share a process to assess how your company has performed so far and how to shift into a long-term strategy. We recommend using the S.W.T. analysis—strengths, weaknesses, and trends—so you can identify key trends in the market and industry that could shape your strategy. We also provide actionable questions to assess four crucial categories: operations, talent, finance, and business development. Take the time in Q4 to tighten up your processes, assess team needs, and strengthen relationships with partners. This will help you hit the ground running in January, ensuring that you start the new year feeling prepared and ahead of the curve. You'll hear all about: 01:32: Q4 is the time to take an honest look at the past year and shift into long-term strategic thinking. 02:00: Introduction to the S.W.T. assessment: strengths, weaknesses, and trends. 02:26: How trends in the market, technology, and consumer behavior can influence your strategy. 03:04: Operations: Questions to ask about bottlenecks, processes, and vendor performance. 04:14: Talent: Where are team bottlenecks? Who is ready for a promotion? Where do you need to upgrade your team? 05:21: Finance: Ensure your prices, margins, and payroll are in check. Focus on profits, not just revenue. 05:57: Business development: Build better relationships with referral partners and explore strategic partnerships. 06:20: Example of creative strategic partnerships to boost sales. 07:09: Wrap up with key insights on setting up recurring revenue and starting next year strong. Rate, review & follow on Apple Podcasts Click Here to Listen! Or Watch on Youtube If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode.

    #20: Decode Your CEO: How an Entrepreneur Thinks

    Play Episode Listen Later Sep 3, 2024 10:20


    Understand and navigate your CEO's entrepreneurial mindset and thinking habits. Entrepreneurs are fast-moving visionaries who thrive on risk, resilience, and a willingness to fail forward. They have a unique set of thinking patterns that can be confusing or even frustrating to more operations-minded executives. By recognizing, understanding, and appreciating these traits, you can find the middle ground that allows you to work more effectively together. In this episode, we break down the entrepreneurial mindset into key components—risk-taking, resilience, and views on failure—while also delving into common thought patterns that drive their decision-making. Understanding these behaviors will not only help you better support your CEO but also strengthen the partnership as a duo. You'll hear all about: 00:39: Challenges operations-minded executives face with visionary entrepreneurs. 01:08: Key qualities of entrepreneurs: risk-taking, resilience, and views on failure. 02:07: Entrepreneurs' unique relationship with risk and why they accept it. 03:25: The importance of resilience in entrepreneurial success. 03:59: How entrepreneurs view failure as a stepping stone to progress. 05:04: Common thinking habits of entrepreneurs that COOs should understand. 06:50: The anxiety-driven belief that everything could be lost, even during success. 09:10: The role of the Second-In-Command in managing and supporting these entrepreneurial traits. Rate, review & follow on Apple Podcasts Click Here to Listen! Or Watch on Youtube If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode.  

    #19: The Four Mandatory Meetings

    Play Episode Listen Later Aug 27, 2024 11:19


    The Four Mandatory Meetings You Should Be Having as a Second-In-Command In this episode of The Right-Hand Roadmap, we dive into the four must-have meetings every Second-In-Command of a founder-led company should be scheduling. Megan Long explains how these meetings not only drive company success but also strengthen your role as a COO. These meetings aren't just about ticking boxes—they're about fostering alignment, driving strategic initiatives, and building strong relationships across the leadership team. From weekly one-on-ones with your CEO to quarterly planning sessions with your entire leadership team, each meeting plays a pivotal role in your success. We also explore the value of skip-level meetings, offering you a way to stay connected with all levels of your organization and truly understand the pulse of your company. You'll hear all about: 00:55 - Meeting #1: Weekly one-on-ones with the CEO or founder; recommended structure and agenda. 04:35 - Meeting #2: Monthly same page meetings; fostering alignment and strategic planning. 05:52 - Meeting #3: Weekly one-on-ones with direct reports; building rapport and ensuring accountability. 08:07 - Meeting #4: Quarterly planning meetings; setting the strategic direction for the company. 09:32 - Bonus: The value of skip-level meetings for maintaining company culture and transparency. Rate, review & follow on Apple Podcasts Click Here to Listen! Or Watch on Youtube If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode. Links mentioned in the episode: "Rocket Fuel" by Gino Wickman & Mark C. Winters  

    #18: Catch-Up From Summer Break: Behind the Scenes of Second First

    Play Episode Listen Later Aug 20, 2024 6:14


    We're Back! Back from our summer break, host Megan Long fills you in on all of the exciting behind-the-scenes happenings at Second First, the company behind The Right-Hand Roadmap podcast! In this casual, chatty episode, you'll hear all about: You'll hear all about: 01:04 – The May launch of a Mastery class, our ten-week certification course. 02:00 – The second big project of the summer: our mastermind event, Exchange. 02:58 – How Megan wants to make Exchange “easy” for attendees compared to other conferences. 03:36 – An exciting, to-be-announced change to the Exchange program. 03:51 – Growing the Second First team. 04:03 – The changes in our podcast, and hard lessons learned when choosing software platforms. 04:43 – Some new and different workshops Megan Long is hosting for unique Seconds-In-Command.   Rate, review & follow on Apple Podcasts Click Here to Listen! Or Watch on Youtube If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode. Links mentioned in the episode: Second-In-Command Mastery – 10 Week Certification Course Second First Exchange – Mastermind

    #17: Reengaging Disengaged Leaders

    Play Episode Listen Later Apr 30, 2024 9:26


    Discover strategies to reengage disengaged leaders. In this episode, we're taking a workshop-style approach to tackle the issue of disengaged leaders head-on. From identifying common reasons behind declining participation to offering actionable strategies for reengagement, we've got you covered. Whether it's addressing managerial burnout, navigating the Peter Principle, fostering a compelling vision, or managing external personal issues, we're here to guide you every step of the way. Throughout the episode, listeners will gain valuable tips on how to recognize signs of disengagement, ask probing questions to uncover underlying issues, and implement effective solutions to reignite passion and commitment in leadership roles. You'll hear all about: 01:08 - Common reasons for declining participation among leaders. 01:28 - Strategies to address managerial burnout are explored, including setting boundaries and practicing stress reduction techniques. 03:28 - The concept of the Peter Principle is introduced, along with strategies to navigate it such as the nine-box grid and dual career ladders. 06:15 - Lack of vision or "what's in it for me" (WIFM) is examined, emphasizing the importance of a compelling and relatable vision for all team members. 07:38 - The Pygmalion effect and its implications for leadership expectations and performance are discussed. 08:42 - External or personal issues affecting leader engagement are acknowledged, highlighting the importance of HR involvement in finding solutions. Rate, review & follow on Apple Podcasts Click Here to Listen! Or Watch on Youtube If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode. Links mentioned in the episode: Nine Box Grid for Talent Management

    #16: Q&A: Compliance Risk, Finding Employment, and Feeling Held Back

    Play Episode Listen Later Apr 23, 2024 9:54


    Listener Submitted Q&A: Compliance Risk, Finding Employment, and Feeling Held Back. In this episode, Megan Long, your host and owner of Second First, dives into the second quarterly Q&A of 2024. Each quarter, we address pressing questions submitted by our listeners. From navigating regulatory challenges to strategizing career moves, we cover a wide range of topics relevant to today's second in commands. Throughout the episode, we offer practical advice and actionable strategies to help listeners overcome common obstacles in their roles. Whether it's convincing a CEO to prioritize compliance, positioning oneself as an attractive candidate for new opportunities, or navigating disagreements with company owners, we provide valuable insights to empower COOs in their journey. You'll hear all about: 01:34 - Question 1: A listener expresses concern about their company's transition into advising work and the lack of focus on compliance. 04:04 - Question 2: A listener asks how to position themselves as an attractive candidate for their next role, tailored to the needs of the CEO. 06:14 - Question 3: Handling disagreements with the CEO about the company's growth strategy, emphasizing the importance of alignment and transparency. Rate, review & follow on Apple Podcasts Click Here to Listen! Or Watch on Youtube If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode. Links mentioned in the episode: https://secondfirst.com/10 - The Right-Hand Roadmap Episode 10: Interviewing for an Executive Role

    #15: Going Dark: Why We Ghost Our Boss

    Play Episode Listen Later Apr 16, 2024 7:11


    Understanding the Impact of Going Dark on Your CEO. In this episode, we're pulling back the curtain on a common but often unspoken habit: the tendency for COOs and executives to disconnect from (or “ghost”) our CEOs. We know firsthand the challenges of navigating the fast-paced, world of reporting to an entrepreneur. But as crucial as it is for us to keep up with their pace, we sometimes find ourselves falling into the trap of “going dark,” whether due to our busy schedules or fear of burdening our CEOs with bad news. But here's the thing: communication breakdowns can lead to a whole host of issues, from duplicated work to frustrated team members. That's why in this episode, host Megan Long is sharing insights on why we ghost our bosses, the repercussions of doing so, and most importantly, practical strategies for fostering open communication and stronger relationships.  You'll hear all about: 01:07 – The common occurrence of COOs “going dark” on their CEOs. 01:20 – Characteristics of entrepreneurs and the challenges they pose for COOs. 02:32 – Communication breakdowns between COOs and CEOs, leading to COOs “going dark.” 04:43 – Exploring the fear-based response of COOs to shield their CEOs from negative news. 05:40 – Strategies for improving communication and preventing “going dark,” including regular updates and same-page meetings. Rate, review & follow on Apple Podcasts CLICK HERE TO LISTEN! OR WATCH ON YOUTUBE If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode.

    #14: Financial Moves to Impress Your CEO

    Play Episode Listen Later Apr 9, 2024 5:39


    Financial Strategies to Impress Your CEO and Contribute to Your Company's Bottom Line. In this episode we dive into some profit-adding financial moves that a Second-In-Command can make, even if they're not a CFO. Together we cover identifying and eliminating waste, renegotiating vendor contracts, and addressing revenue leakage. These strategies can help plug the holes in the financial bucket and pave the way for sustainable growth. By implementing these strategies, COOs can demonstrate their value and contribute to the financial well-being of their organizations.  You'll hear all about: 01:03 - The importance of auditing every expense line item to identify waste. 01:52 - Examples of areas where waste might occur, such as unused software licenses and unnecessary subscriptions. 02:28 - How and when to renegotiate vendor contracts to reduce costs. 03:26 - Addressing revenue leakage, including adjusting prices to cover credit card processing fees. 04:11 - Other areas of revenue leakage, such as inaccurate billing and late payment fees. Rate, review & follow on Apple Podcasts Click Here to Listen! Or Watch on Youtube If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode.

    #13: Avoid Burnout: The 7 Types of Rest

    Play Episode Listen Later Apr 2, 2024 8:27


    Navigating Burnout: Strategies for COOs and Second-in-Commands. In this insightful episode, we delve into the critical topic of avoiding burnout in the demanding role of a Second-In-Command. As COOs, our responsibilities often overwhelm us, leading to physical, mental, and emotional exhaustion. Host Megan Long shares her personal experiences with burnout and highlights the importance of prioritizing self-care. We explore the seven types of rest essential for maintaining our well-being and effectiveness in our roles. You'll hear all about: 01:16 - Megan's personal encounters with physical and mental burnout though her career, and its impact. 01:39 - Dispelling misconceptions about what "boundaries" mean and emphasizing self-care. 02:20 - An overview of the Seven Types of Rest 02:49 - Physical Rest: Beyond sleep, vital for preventing health issues. 03:41 - Mental Rest: Strategies for preserving mental resources. 04:13 - Emotional Rest: Validating emotions and fostering support systems. 04:58 - Social Rest: Curating positive connections and setting boundaries. 05:39 - Sensory Rest: Unplugging to reduce stimulation and rejuvenate. 06:04 - Creative Rest: Cultivating imagination and problem-solving skills. 06:31 - Spiritual Rest: Finding purpose and resilience. Rate, review & follow on Apple Podcasts Click Here to Listen! Or Watch on Youtube If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode. Links mentioned in the episode: "What If There's More?: Finding Significance Beyond Success" by Traci Schubert Barrett

    #12: You Are Who You Spend Time With

    Play Episode Listen Later Mar 26, 2024 5:57


    The Power of Proximity in Habits & Success. Inspired by a favorite read, "Atomic Habits" by James Clear, we discuss the impact of our social environment on our habits and success: the close, the many, and the powerful. Clear discusses how we tend to mirror the habits of those around us, particularly the "close" individuals in our lives—the friends, family, and peers we interact with regularly. Studies even show that our habits are significantly influenced by the habits of our closest connections, regardless of physical distance. The phenomenon of rising or falling to the level of those around us is profound. We cover two fascinating studies - astronauts emerging from a single MIT class and the statistical likelihood you will follow the physical weight and body type of those closest to you. Our surroundings deeply impact our behaviors and identities. As a Second-In-Command, it's crucial to curate your social environment intentionally. Seek out groups and communities that challenge you to grow both personally and professionally. Surround yourself with individuals who inspire you to be your best self. You'll hear all about: 00:23: The core message of "Atomic Habits" by James Clear, emphasizing the role of social circles in habit imitation. 01:06: Explore how proximity influences behavior and habits. 01:45: Two incredible studies on the ripple effect of habits within close-knit social circles. 02:25: Jim Rohn's famous quote and the profound effect of surrounding yourself with high-performing peers. 04:16: The importance of intentional community-building and finding sources of positive influence outside of the office. Rate, review & follow on Apple Podcasts Click Here to Listen! Or Watch on Youtube If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode. Links mentioned in the episode: "Atomic Habits: An Easy & Proven Way to Build Good Habits & Break Bad Ones" by James Clear

    #11: Do You Need an EA or a COO?

    Play Episode Listen Later Mar 19, 2024 8:40


    Executive Assistant vs. Chief Operating Officer: When to Make the Leap. In today's episode, we delve into a critical topic that often arises when scaling a small business: the distinction between hiring an Executive Assistant (EA) or a Chief Operating Officer (COO). This is a common conversation we have with founders navigating growth, especially as they pass the mid six to low seven figures in revenue. An Executive Assistant can be a fantastic Second-In-Command, adept at handling day-to-day operations and ensuring tasks are executed with precision. They excel at anticipating an entrepreneur's needs and are invaluable in keeping the CEO on track and on time. However, a COO operates on a larger scale, focusing on the strategic vision and long-term planning. They craft action plans and hold others accountable to meet overarching goals. Deciding when to transition from an EA to a COO depends on various factors - financial and strategic - that we cover in the episode. Conducting an "activity inventory," as suggested by Dan Sullivan, can be helpful in identifying what the true business need is. If you find yourself overwhelmed by strategy or lack clarity on execution steps to achieve your vision, it might be time to bring on a COO. You'll hear all about: 01:12: The multifaceted role of an Executive Assistant (EA) as a strategic partner and operational powerhouse. 02:16: The key differences between the scale and scope of operations for an EA versus a COO, emphasizing their complementary functions. 03:13: The differences in accountability—from an EA's individual performance to a COO's holistic responsibility for organizational success. 04:00: When is it time to transition from an EA to a COO? Including salary considerations and strategic needs. 05:09: How to implement an activity inventory to identify tasks for delegation, laying the groundwork for informing which position you need to fill. 05:26: Basic interview preparation tips, including researching the company and formulating intelligent questions. 06:44: The necessity of having questions for the interviewer and showcasing investment in the position. 07:06: Anticipating and preparing for questions about accountability, teamwork, and handling disagreements. 07:49: Addressing choice-based questions, aligning personal values with the company's ethos, and culture preservation. 08:24: Advising on preparing a loose plan for the first 30, 60, 90 days in the executive role. 09:21: Stressing the importance of observing, understanding, and building buy-in before implementing changes. Rate, review & follow on Apple Podcasts Click Here to Listen! Or Watch on Youtube If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode. Links mentioned in the episode: Strategic Coach Delegation Exercise

    #10: Interviewing For an Executive Role

    Play Episode Listen Later Mar 12, 2024 9:59


    Mastering Executive Interviews: Tips for Aspiring Second-in-Commands. Interviewing for an executive role can be full of complicated dynamics and intricacies. If you're aiming for a new leadership position, host Megan Long shares invaluable advice and prepares you for the unexpected challenges that might come your way. With personal anecdotes and actionable insights, this episode covers everything from bizarre interview scenarios to the crucial follow-up process. Learn how to stand out, impress your interviewer, and confidently navigate questions about accountability, team dynamics, and strategic planning. You'll hear all about: 00:49: Preparing for unforeseen challenges and maintaining flexibility during executive interviews. 01:14: Megan's nightmare interview experience, and lessons learned. 03:18: The significance of thorough preparation and follow-up after an interview, sharing a personal success story. 04:35: Emphasizing the impact of post-interview follow-up and the role it played in securing a job offer. 05:13: The importance of making interviewers feel seen and special. 05:26: Basic interview preparation tips, including researching the company and formulating intelligent questions. 06:44: The necessity of having questions for the interviewer and showcasing investment in the position. 07:06: Anticipating and preparing for questions about accountability, teamwork, and handling disagreements. 07:49: Addressing choice-based questions, aligning personal values with the company's ethos, and culture preservation. 08:24: Advising on preparing a loose plan for the first 30, 60, 90 days in the executive role. 09:21: Stressing the importance of observing, understanding, and building buy-in before implementing changes.   And finally, we'd love to hear your personal Second-In-Command interview stories! Email your experiences to podcast@secondfirst.com.  Rate, review & follow on Apple Podcasts Click Here to Listen! Or Watch on Youtube If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode. Links mentioned in the episode: "The First 90 Days, Updated and Expanded: Proven Strategies for Getting Up to Speed Faster and Smarter" by Michael D Watkins

    #9: Adding Revenue Fast This Quarter

    Play Episode Listen Later Mar 5, 2024 8:12


    Boost Your Bottom Line: Generating Quick Revenue Injections for Small Businesses. Have you ever wished you could generate revenue into your business quickly - like, this month? Even if it's nonrecurring revenue, just have some extra cash injected into your business? There are creative and effective methods to inject immediate revenue into your small business. Host Megan Long explores creative approaches, from affiliate partnerships to hosting workshops, providing actionable insights for businesses looking to diversify income streams. Learn how leveraging vendor programs and optimizing existing client relationships can lead to quick financial gains. Whether considering price adjustments or exploring add-on services, this episode equips Seconds-In-Command of entrepreneurs with practical strategies to quickly add a boost to their bottom line. You'll hear all about: 00:57: Affiliate partnerships, and generating commission income from referring your favorite products.  01:15: How Second First leverages affiliate links in curated content, emphasizing the importance of recommending products or services genuinely used. 01:50: How to create custom partner programs with local small businesses. 02:34: Using in-person workshops or paid webinars as a fast revenue-generating tactic. 03:30: Encouraging businesses to explore vendor programs for rebates, incentives, and marketing funds, maximizing opportunities for financial support. 04:58: Insight into marketing development funds (MDF) and co-op funds, providing a budget for co-branded events with suppliers. 05:44: Identifying opportunities to add value to current clients and introducing new services for additional fees, including a personal case study. 07:11: The importance of periodic price adjustments & increases.  Rate, review & follow on Apple Podcasts Click Here to Listen! Or Watch on Youtube If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode.

    #8: Finding Your Flow Zone

    Play Episode Listen Later Feb 27, 2024 6:41


    Navigating the Flow Zone for COOs and Second-in-Commands. The "Flow Zone" refers to a psychological state where a person is fully immersed and focused on an activity - there's a sense of energized focus, complete involvement and enjoyment. It is often described as being "in the zone". In this episode, we take a deep dive on one of the flow characteristics Mihaly Csikszentmihalyi identified: the balance of skill level and challenge level. Flow greatly effects how a Second-In-Command functions in their role - we cover techniques to find and stay in flow as a leader. You'll hear all about: 00:29: Defining the flow zone and its relevance to COOs and leaders, emphasizing the importance of finding individualized approaches.  01:04: The eight characteristics of flow as defined by Mihaly Csikszentmihalyi. 02:02: The balance of skill level and challenge level, and how they affect flow. 04:20: A conversation to have with your founder to find more challenge in your role. 05:11: The non-linear path executives will experience in and out of flow. 05:42: Techniques to avoid distractions pulling you out of flow. Rate, review & follow on Apple Podcasts Click Here to Listen! Or Watch on Youtube If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode. Links mentioned in the episode: "Flow: The Psychology of Optimal Experience" by Mihaly Csikszentmihalyi

    #7: Parallels Between Athletes and Corporate Leaders

    Play Episode Listen Later Feb 20, 2024 9:51


    The Winning Mindset: Athlete's Lessons for Corporate Leaders. In this episode of "The Right-Hand Roadmap," dive into the parallels between an athlete's mindset and corporate leadership. Host Megan Long, a former competitive bodybuilder turned entrepreneur, shares invaluable lessons from her journey as a pro athlete that seamlessly apply to the professional world. Discover practical insights on coachability, doing your best, longevity, preparation for the unexpected, visualization, discipline, embracing losses, time management, recovery, and the constant pursuit of improvement. You'll hear all about: 02:43: Recommend reads that draw connections between athletics and business, shedding light on common traits of winners.  03:37: Top lessons learned from being an athlete, starting with the importance of being coachable and leveraging mentorship. 04:56: The inevitability of unexpected challenges, and how control of the controllables applies to both athletics and business. 05:39: the effectiveness of visualization, with personal anecdotes from Megan's competitive bodybuilding journey. 06:51: The significance of discipline, setting a schedule, and the value of sticking to routines, especially in the absence of constant motivation. 07:49: Viewing losses as valuable feedback and how constructive criticism in business is akin to improving through athletic challenges. 08:15: Stressing the essence of time management and introducing Randy Zuckerberg's "pick three" rule for prioritization. 08:36: Recognizing the importance of recovery, drawing parallels between avoiding burnout in athletics and maintaining operational efficiency in business. 09:31: Embracing the idea that there's no finish line in personal and professional development, always room for improvement. Rate, review & follow on Apple Podcasts Click Here to Listen! Or Watch on Youtube If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode. Links mentioned in the episode: "Elite Minds: How Winners Think Differently to Create a Competitive Edge and Maximize Success" by Dr. Stan Beecham HBR's 10 Must Reads on Mental Toughness "The Founder & The Force Multiplier: How Entrepreneurs and Executive Assistants Achieve More Together" by Adam Hergenrother & Hallie Warner Episode Five: Randy Zuckerberg's "Pick Three" Rule

    #6: Transitioning from Corporate to an Entrepreneurial Company

    Play Episode Listen Later Feb 13, 2024 9:51


    Navigating the Leap from Large Corporation to Small Business. In this episode, explore the transitional shift as a leader from big corporate to small businesses. Many small entrepreneurial businesses hire externally for executive roles, especially new positions that they add. This often means experienced candidates are coming from larger organizations, which means facing a sizable adjustment in culture and leadership style. Dive into the pros and cons, transition tips, and key considerations as a leader making this impactful move. Learn about compensation, career growth, flexibility, and the unique challenges and advantages of being a Second-In-Command in a smaller setting reporting directly to a founder. You'll hear all about: 00:29: An overview of the Pros and Cons of transitioning to a small business environment.  01:12: Explaining the differences in pay & benefits, and the unique compensation packages that you might find in small businesses. 02:21: Career growth and professional development opportunities in entrepreneurial settings. 03:43: Finding true flexibility in your leadership role. 04:42: Shedding corporate mindsets to adapt to entrepreneurial companies, and how old habits might hurt you. 06:22: Building for tomorrow, not for scale. 07:10: Adapting to the pace and speed of working for a founder in a small business environment. 08:16: The difference in budgeting cycles and decision-making. 08:34: The unique impact and meaningful leadership role in smaller businesses.  Rate, review & follow on Apple Podcasts CLICK HERE TO LISTEN! OR WATCH ON YOUTUBE If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode.

    #5: Q&A: Absent CEOs, Managing Older Generations, Holding Multiple Roles, and Maintaining Self-Care

    Play Episode Listen Later Feb 6, 2024 16:50


    First Listener-Submitted Q&A: Absent CEOs, Managing Older Generations, Holding Multiple Roles, and Maintaining Self-Care. Dive into the first quarterly Q&A of "The Right-Hand Roadmap" where COOs and Seconds-In-Command tackle listeners' pressing questions. In this episode, listeners can expect a dynamic Q&A session addressing key challenges faced by Seconds-In-Command. From dealing with remote CEOs affecting company culture, managing an older team, embracing a proactive approach to self-care, and balancing diverse responsibilities, each question offers valuable insights and actionable advice. You'll hear all about: 01:37: Guidance on fostering engagement in a fully remote company with an absent CEO, and suggestions on initiating a "Same-Page Meeting" to redefine roles.  04:34: Overcoming self-limiting beliefs about managing an older team. Emphasizing that age does not equate to experience and adopting a mindset shift to boost confidence. 06:24: Strategically managing responsibilities during temporary role transitions, and addressing concerns about maintaining operational efficiency while focusing on generating new business. 09:19: Insight into balancing personal and professional routines. Introducing the "Pick Three" rule by Randi Zuckerberg and practical tips for prioritizing time effectively. 11:28: A walk-through of the Ideal Week exercise for effective time management. Tips on creating themes for each day, prioritizing tasks, and maintaining flexibility without compromising discipline. RATE, REVIEW & FOLLOW ON APPLE PODCASTS If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode. LINKS MENTIONED IN THE EPISODE: Tango automatic process documentation “Rocket Fuel” by Gino Wickman & Mark C. Winters "Time Traps: Proven Strategies for Swamped Salespeople" by Todd Duncan "Pick Three: You Can Have It All (Just Not Every Day)" by Randi Zuckerberg

    #4: Saying "No" To Your CEO's Ideas

    Play Episode Listen Later Jan 30, 2024 9:00


    The Delicate Balance of Saying "No" To Your CEO's Ideas While Fostering Collaboration. Explore the challenges of handling a CEO's myriad ideas and learn essential strategies to transform them into actionable plans. This episode empowers operations executives to provide valuable input, prioritize initiatives, and collaborate effectively with visionary leaders without sacrificing their unique strengths.. You'll hear all about: 00:29: The challenge of managing unfiltered ideas from visionary CEOs and the importance of adopting the right mindset.  02:56: The concept of organizational whiplash caused by too many ideas without momentum and the potential negative impact on teams and projects. 04:01: Empowering operations executives to say no to certain ideas and introducing the Idea Manager role for COOs. 04:45: Tool 1: The 0 to 10 Principle, a collaborative approach to developing and fleshing out CEO ideas, ensuring operational plans align with the vision. 05:26: Tool 2: The Priority Prism, a method to assign numeric values to urgency, importance, impact, and effort. 06:32: Practical example and explanation of creating a Priority Prism.   Rate, review & follow on Apple Podcasts If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode. Links mentioned in the episode: Download the free Priority Prism Tool "The Founder & The Force Multiplier: How Entrepreneurs and Executive Assistants Achieve More Together" by Adam Hergenrother & Hallie Warner

    #3: The Three Problems with COO Peer Groups

    Play Episode Listen Later Jan 23, 2024 8:04


    How To Bring Positive Change to COO Peer Groups & Organizations. There are very few peer groups and organizations specializing in the Second-In-Command. Through personal experiences, there are three common problems that been them from being as valuable and successful as they should be. In this episode we explore how to unlock the potential of these COO peer groups while addressing their common challenges, and maximizing their impact on personal and professional growth. If you are a member of one of these professional organizations, learn about three key issues affecting these groups and discover how to affect change from within and achieve a meaningful return on your investment of time and effort. We also explain how our Mastermind, Exchange, acknowledges these common issues and overcomes each of the three. You'll hear all about: 00:53: How revenue thresholds limit the relevance of member-companies, and how they typically don't cater to small businesses.  01:48: The importance of a formal framework for productive time together in the peer group. 03:40: How ROI of a COO's time - their most valuable asset - is the most important piece to ensure attendance.  05:54: The power of peer groups for Second-In-Command professionals and their unique benefits. 06:48: About Second First: Exchange, the Mastermind for Seconds-In-Command of founder-led companies. Rate, review & follow on Apple Podcasts If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode. Links mentioned in the episode: Second First: Exchange - Apply for membership to the 2024 Mastermind for Seconds-In-Command of founder-led companies.

    #2: Entrepreneurs Shouldn't Delegate to Their Second-In-Command

    Play Episode Listen Later Jan 16, 2024 9:31


    Explore the myths of delegation in visionary entrepreneurship and uncover the true role of a second in command in reducing organizational noise and enhancing collaboration.   In this episode we explore the concept of delegation, separating it into two definitions, and discuss what a great Second-In-Command should do to reduce organizational noise and enhance collaboration between the CEO and COO.   Discover the difference between beneficial delegation, focusing on tasks outside your expertise, and the potential pitfalls of task-based delegation. We delve into the crucial distinction between upward and downward communication, emphasizing the proactive role of the second in command in taking ownership of outcomes.   Learn practical strategies for effective upward communication, including scheduling one-on-one sessions to uncover your CEO's concerns, anticipating their needs, and identifying problems, not just tasks. We also share tips on concise communication to avoid overwhelming your CEO with excessive information.     You'll hear all about:   00:51: Challenging the belief that entrepreneurs should "delegate". 01:51: The two definitions of delegation, and which an entrepreneur should never do. 02:27: Exploring Larry Linne's concepts of upward and downward communication. 03:25: Proactive strategies for upward communication and understanding your CEO's concerns and mindset. 04:39: How to effectively share updates with your CEO, and how to balance sharing details to avoid frustration and misinterpretation. 06:01: Tips for successful upward communication, including structuring recurring one-on-one meetings. 06:41: Anticipating your founder's needs and identifying problems, not just tasks.   Rate, review & follow on Apple Podcasts If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode. Links mentioned in the episode: "Make the Noise Go Away: The Power of an Effective Second-In-Command" by Larry G. Linne "Rocket Fuel" by Gino Wickman & Mark C. Winters Second First Free Guide: Four Rules for Effective Communication with Entrepreneurs  

    #1: Which of the Seven Types of COO Are You?

    Play Episode Listen Later Jan 9, 2024 13:41


    Learn the seven types of COO, and receive reflection questions for each type to optimize your role. In this inaugural episode of "The Right-Hand Roadmap," dive into the influential Harvard Business Review article, "Second in Command: The Misunderstood Role of the Chief Operating Officer." Uncover the intricacies of the COO role and identify seven archetypes that shape the #2 leader in companies. From "Executor" to "Heir Apparent", host Megan Long guides COOs through self-reflection questions, providing actionable insights to optimize their role. Gain clarity on aligning strategy with operations, navigating co-leadership, and addressing potential blind spots in succession planning. You'll hear all about: 00:49: Exploration of the COO's role in relation to the CEO as an individual and the origin of the seven COO archetypes. 01:55: Practical self-reflection questions for COOs based on their identified archetype. 02:57: Importance of clarity breaks and deep work days for effective leadership. 03:03: How the Executor runs a company to allow the CEO to focus on big-picture strategy. 04:41: Unpacking the Change Agent archetype and its strategic initiatives. 06:16: Insights into the Mentor archetype and its evolving role. 07:19: Understanding the Other Half archetype and its role in complementing the CEO. 08:51: Exploring the dynamics of the Partner archetype in co-leadership scenarios. 10:23: Insightful reflections for the Heir Apparent archetype and the importance of succession planning. 11:32: Discussion on the MVP archetype and key considerations for staying in the role. Rate, review & follow on Apple Podcasts If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode. Links mentioned in the episode: HBR: Second in Command: The Misunderstood Role of the Chief Operating Officer "Make the Noise Go Away: The Power of an Effective Second-In-Command" by Larry G. Linne  "Rocket Fuel" by Gino Wickman & Mark C. Winters

    Claim The Right-Hand Roadmap

    In order to claim this podcast we'll send an email to with a verification link. Simply click the link and you will be able to edit tags, request a refresh, and other features to take control of your podcast page!

    Claim Cancel