A short discussion of leadership improvements you can start using in your startup today as a technical executive.
Ever found yourself piling food on your plate(s) because you were in a free buffet? That's what some teams have started doing with the new capabilities they got from AI. Don't fall for empty-calorie features and product obesity. More in this week's episode.Grab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
If your main lens for the outside world and the industry is based on social media and LinkedIn, you're probably getting a very distorted view of reality. It can be depressing, demotivating, or just derailing. It doesn't have to be that way!Grab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
There are laws of nature, and then there are the things that we tell ourselves are fixed, yet really aren't. How many of the walls around you are of your own doing? Let's break free.Grab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
Experience tells that on most engineering teams, there's someone underperforming, either due to a mistake you made or inherited. The question is, what are you going to do about it? More in this week's episode.Grab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
What you're holding out on saying is holding you back. How many months have you wasted not opening your mouth? How many opportunities? How much frustration has been building up? Today's episode puts an end to that.Grab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
Are you merely winging it, or did you take a second to consider what you're doing and where you're headed? Being mindful for a few minutes could make all the difference between a proactive leader and a floating one. More in this week's podcast!Grab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
When we censor ourselves and parts of our personality too much at work, it shows. Your team can feel that there's a barrier. Your peers will sense it. Can you unleash yourself?Grab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
As we're starting the year, people instinctively choose all the things they want to do. It's like piling our plates at a buffet. But that's a sure-fire way to lose your appetite even before getting started. Know your No.Grab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
Anyone can get a few good people to join the team, but turning that into an actual team? That's a whole different game. Are you crafting collaboration? Let's get you ready for an amazing 2026.Grab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
Humans are amazing pattern-matching machines. However, sometimes we extrapolate from a single anecdote and build upon a shoddy foundation. More in this week's episode.3+2 going out of business saleLock special pricing for Unplugged with Aviv: https://avivby.gumroad.com/l/unpluggedGrab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
DRY is a rule every engineer knows, but so many leaders forget. We get stuck in loops, going through the same mistakes and wrong moves, expecting the same action to have a different result. Let's discuss DRY leadership.3+2 going out of business saleCommon sense videoLock special pricing for Unplugged with Aviv: https://avivby.gumroad.com/l/unpluggedGrab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
Of course you care about the team, but sometimes we let that care get in our way. We confuse caring for them with coddling and overprotection, which results in teams that happily and calmly go on their merry paths for mediocrity (or worse). More in this week's podcast!Grab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
Sometimes, getting so good at something that we do it automatically makes us worse at it. We get the task done and miss the bigger picture. That's what I'm often seeing with hiring and promotion decisions. This week's podcast episode is about breaking out of the autopilot hiring loop and finding the opportunities to do something even more impactful.Check out Unplugged with Aviv.Grab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
I recently had conversations with several founders and executives after their companies had a major success or failure. What we get out of these moments (other than financial success, if any) is what we learned and how we improved. This week's episode is about not wasting that!Lock special pricing for Unplugged with Aviv: https://avivby.gumroad.com/l/unpluggedGrab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
Optimizing for the next step ahead of you can get you to a local maxima, but still lead you down the wrong path. As a leader, you cannot fall for greedy algorithm leadership! More in this week's episode.Unplugged with Aviv is currently on a reduced rate and once you join, you lock it for life!Grab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
Sometimes, even when we're told exactly what mistake we're walking into, we still have to learn the "hard way." Otherwise, we could all spend a year reading a bunch of books and become perfect in whatever we set out to achieve. Yet, if we don't actually learn, we're wasting our time going through the toils of the hard way without at least getting better. More in this week's episode.Grab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
Just like we iterate on our products, we need to learn how to iterate effectively on our organizations. Framing things as experiments and tests makes it easier to gain momentum, reduces pushback, and helps get people to speak up. This week's episode is about the testing hack!Grab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
I've yet to come across someone who had a shortage of excuses. When those are then used to justify not addressing problematic people because they are "critical," we create long-term cultural damage to the org that will be incredibly hard to undo. More in this week's episode!Please answer this single-question survey about the Rome Sessions.Get the free tech exec roadmap email course.Grab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
Death by a thousand papercuts often happens when we neglect particular issues, expecting us to have the opportunity to handle them "seriously" eventually. That neglect can be disastrous. Stop digging!Please fill out this single-question poll about the Rome Sessions. I'd would mean a lot to me!Get my free email course: Tech Exec RoadmapGrab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
Understanding the natural thought patterns of your CEO will help you communicate effectively and create trust rather than lose it. One such aspect is the "anecdote machine" thinking. With few data points, extrapolation roams free, and it often misses. More in this week's episode!Please fill out this single-question poll about the Rome Sessions. I'd would mean a lot to me!Grab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
The ingenious use of paper towels to unlock business value and how that connects to your team's autonomy and agency. Are people sitting on their hands waiting to be told what to do, looking directly at obvious solutions and not implementing them? A lesson from a bar in Rome.Check out Unplugged with AvivGrab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
Just because it comes to you so easily, it doesn't mean you should allow that behavior to guide your thinking. Yes, coming up with reasons why something won't work is easy and might feel like you're demonstrating your smarts. Still, in this week's episode, I discuss flipping that thinking around.Grab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
Single stepping might be a good way to debug some gnarly code, but it won't cut it as a leadership practice. Without learning how to step back and look at things at a grander scale, you're bound to think too "small." More in this week's episode.Last call to join The New Non-Negotiables of Tech Leadership in 2026Grab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
You ask for something simple and then get a deer in the headlights look from the other person. The lack of autonomy and agency can hit us everywhere, mcdonald's, restaurants, and your org! More in this week's episode.Check out my free upcoming live session: The New Non-Negotiables of Tech Leadership in 2026Grab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
Effective leadership enables rapid growth, adjusted to each person's current situation and abilities. You can unlock dramatic success by aligning around simple yet impactful coaching habits. More about that in this week's episode!Join my upcoming free session, The New Non-Negotiables of Tech Leadership in 2026.Grab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
The mirrors in our apartment got me thinking about affordances and deliberate organizational experience design. Are you making the right things accessible?Join my free livestream: The New Non-Negotiables of Tech Leadership in 2026Grab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
Risks are unavoidable in our day-to-day work. Yet many of us need some "calibration" of our treatment of risks. Many tech-oriented people have a risk appetite that differs from the company's, resulting in missed opportunities and a slower pace. Let's help you address that in this week's episode.Check out Unplugged with Aviv.Grab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
For more than a week, I kept saying the exact same thing at the same caffé in Rome, and we got a different drink almost every time. Communication is weird. Words are vague. Realizing that is essential to become an effective leader. More in this week's episode.Check out Unplugged with AvivGrab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
Fear has two opposite ways of harming how you lead—do you freeze or do you roll over? Either way, fear-driven leadership is not really leadership. You can short-circuit fear's control of your behavior with these three steps. Check out Unplugged with Aviv.Grab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
When we see things with a fresh set of eyes, we can notice many things others around us have gotten used to. Be it if you're standing in front of cheeses you've never heard of before in an Italian supermarket or when you joined a new team. How can we maximize learning to ensure we improve our weak spots and double down on our strengths?Check out Unplugged with Aviv.Grab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
If your internal conversations are all about your struggles and obstacles, and you always skip over the actual progress you've made, you will inevitably generate self-inflicted burnout sooner or later. Don't tell yourself you're on a hamster wheel… if you ain't!Check out Unplugged with Aviv.Grab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
You should be thinking ahead, but don't confuse that with useless busywork that doesn't actually matter. We do it because we're anxious, because we want to do *something*, or because we wrongly mistake that for leadership. But if there's no diff, it doesn't matter—or even worse.Check out Unplugged with Aviv.Grab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
We moved to Rome and are essentially starting the house from scratch. It's tough, but also liberating. When we're only limiting ourselves to incremental thinking, we might get stuck in a local maximum. Without liberating ourselves from current constraints, making substantial progress can be nearly impossible. Check out Unplugged with Aviv.Grab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
There are things that you can just put aside and not think about them until you have to. And then there are areas where you can save a lot of effort by ensuring regular maintenance. That's the difference between having to overwhelm your org with the equivalent of WD40 in a rush, and having the ability to handle a situation you knew would come with an already laid out plan. More in this week's episode!Check out Unplugged with Aviv.Grab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
You definitely shouldn't be too hard on yourself, and any particular failure shouldn't rattle you too much. Yet, it is dangerous to get so accustomed to failures and cutting yourself slack that you never start taking action. Rather than keep pushing that diet off by a week, how about committing to some baby steps in the right direction right now? More in this week's episode.Check out Unplugged with Aviv.Grab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
Whenever you're hiring someone, you realize that titles don't mean the same for everyone. It's not enough to have a reference call where they say someone was a "good senior engineer" and be satisfied, nor can you just interview for a "CTO" position without understanding what CTO even means in the company. This week's episode is about ensuring you get the right people in the right positions.Check out Unplugged with Aviv.Grab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
Somewhat annoyingly, my usual reply when someone tells me they have a certain issue is to ask for real examples. You'd be surprised to see how often people are overly critical of themselves, or obsess over issues long resolved. In today's podcast episode, we talk about learning to shortcircuit a lot of internal criticism, so you only bother with what actually matters.Unplugged with Aviv.Grab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
Cognitive dissonance is sometimes a must, because not everything can be clearly decided one way or another. Nevertheless, while you might be aware of the dissonance, as it gets spread in your organization it usually translates into confusion and misalignment. In this episode, we discuss how you'll avoid dissonance to create a more autonomous team around you.Check out Unplugged with Aviv.Grab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
So many CEOs are worried about their team lacking "urgency" and throw that word around, without realizing how to increase productivity in a manner that's effective. Too often we end up with performance hustling, where people make a show of working hard. Instead, you can create real urgency by showing how much you value everyone's time. More in this week's episode!My new offering, with way too low introductory prices: Aviv UnpluggedGrab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
We're all going to make a lot of mistakes, we might as well get better at maximizing the learning-per-mistake we get. What doesn't kill you makes you stronger… if you actually make the effort to get better knowing what you now know. This week's episode is about managing your mistakes portfolio.Grab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
Everyone celebrates long-tenured team members—but what if comfort is killing your company? Let's discuss the hidden dangers of having people who've been in the same seat for too long. From culture fossilization to growth stagnation, we'll talk about how stability can become a sedative, and why fresh eyes—not old habits—are what drive real progress. If you've got people who “know how things work,” ask yourself: are they still moving forward, or just making sure nothing changes?Grab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
When things aren't going smoothly, most tech leaders don't slow down to rethink—they speed up to fix. We overcompensate. We protect the team too much, get involved in every decision, pile on late nights, or jump in to do others' jobs. It feels noble, but it's actually avoidance. In this episode, I unpack the hidden damage of overcompensating leadership: how it stunts team growth, creates dependency, and feeds your own ego more than your org's future. If you think you're being helpful, this one's for you.Grab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
Many leaders nowadays suffer from this chronic condition. They do everything right if you only judge each single action by itself. On any given day, you can look at their decisions and say you would've done the same. But the best leaders know that this is a "greedy algorithm" sort of trap and escape. Are you suffering from chronic reaction?Grab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
Imagine if your private leadership notebook — the one where you wrote what you really think about your team — suddenly became public.How surprised would they be reading it? How surprised would you be watching their reactions?In this episode, we explore the uncomfortable but essential gap between what leaders think and what they actually say.Learn why withholding honest feedback creates silent confusion, why coaching means sharing the real story early, and how radical transparency can turn things around.The uncomfortable truth:If honesty would shock your team, your leadership isn't as strong as you think.Stop Ad-Hoc LeadingGrab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
Product Mastery – The Tech Leader's Force MultiplierMost tech leaders settle for “understanding the product.” But true product mastery is something else entirely. It's the difference between being a tech "leader" and being a genuine executive. In this episode, the final one in the series, we unpack what product mastery really means, why it's the trait that amplifies all the others, and how it lets you shape not just what gets built—but what wins. If you've ever felt like your team's impact is capped by business decisions you don't control, this is your way in.Grab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
Executive Mindset — Suspending DisbeliefBefore you shoot it down, can you believe it's possible? This penultimate episode in our eight traits series is about cultivating the executive mindset: the leader who fuels momentum by suspending disbelief, creating space for bold solutions instead of killing ideas with realism too soon.Don't be a CT-No video.Grab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
Say It Like You Mean It: Communication for Tech LeadersIn this episode, we continue our deep dive into the eight essential traits of exceptional tech leaders—this time, tackling the ever-crucial skill of communication. Too many leaders assume that because they've said something, they've communicated it. But how often have you walked away from a conversation certain you were clear, only to discover later that the other person heard something entirely different?Whether you're speaking to your team, your peers, or your board—this is the difference between alignment and chaos.Grab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
You're Not Coaching—You're Just Talking at PeopleIn this next installment of the Eight Traits series, we dive into one of the most misunderstood (and underused) leadership skills: Coaching.Everyone thinks they're coaching because they give feedback or advice. But real coaching? It's about helping people think better, not just telling them what to do.If you want a team of independent thinkers—not task rabbits—this one's a must.Grab my free impact coaching framework ebook.Grab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
Most tech leaders say they value autonomy. But when it comes to actually letting go and empowering their teams? That's where the cracks show. In this episode of the Eight Traits series, I unpack how autonomy isn't just about giving freedom—it's about intentional delegation, trust, and designing teams that think for themselves (without blowing things up).If you're still the bottleneck—or if “delegation” means throwing tasks over the fence—this one's for you.Grab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
For years, I've guided tech executives through a simple self-assessment of eight leadership traits—helping them pinpoint the highest-ROI areas for growth. Now, I'm bringing that process to the podcast. In this series, we'll break down each trait, giving you a framework to assess yourself and practical ways to improve.After previously discussing vision, now we're covering translating that into action: Instilling Purpose. Vision's no good if it's locked up in your head because then you have to play the master of puppets to make it a reality. Once you master instilling purpose, you gain the genuine benefit of having an empowered team work toward the same objective. More on cultivating that in this week's episode. Grab a copy of my books, Capitalizing Your Technology and The Tech Executive Operating System.Subscribe to the best newsletter for tech executives.For any questions or comments, reach out to me directly: aviv@avivbenyosef.com
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