Boiling The Tech Exec Podcast With Aviv Ben-Yosef podcast

7:48

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…

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Too Cozy 8:54

13 days ago8:54

8:54

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…

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Overcompensating 8:37

20 days ago8:37

8:37

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…

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Chronic Reaction 10:08

27 days ago10:08

10:08

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…

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The Notebook Test 9:50

5 weeks ago9:50

9:50

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 Leading 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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Eight Traits: Product Mastery 11:05

6 weeks ago11:05

11:05

Product Mastery – The Tech Leader’s Force Multiplier Most 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…

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Eight Traits: Executive Mindset 9:32

7 weeks ago9:32

9:32

Executive Mindset — Suspending Disbelief Before 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…

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Eight Traits: Communication 12:09

8 weeks ago12:09

12:09

Say It Like You Mean It: Communication for Tech Leaders In 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…

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Eight Traits: Coaching 8:46

9 weeks ago8:46

8:46

You’re Not Coaching—You’re Just Talking at People In 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…

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Eight Traits: Autonomy 10:38

10 weeks ago10:38

10:38

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…

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Eight Traits: Instilling Purpose 10:52

11 weeks ago10:52

10:52

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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Eight Traits: Vision 8:31

12 weeks ago8:31

8:31

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. This time, we're continuing with vision : A foundational tenet of every strategy, executives who lack vision don't know where they're headed. Let's go over simple questions to assess whether you've got enough of a vision or not. Check out my video about moving upstream and gaining vision. 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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Eight Traits: Accountability 14:48

13 weeks ago14:48

14:48

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. We’re starting with accountability : Can people trust you to follow through? Do you deliver on what you commit to? Let’s find out. 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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Other People's Games 12:52

14 weeks ago12:52

12:52

When you're playing other people's games, you're following a path selected by others. You might have a better way of reaching that destination, or an entirely different one. Too often, we find ourselves playing by rules that weren’t designed for us, following paths that don’t serve us, and chasing goals we never truly chose. In this episode, I break down the power of opting out, the courage it takes to reject playing other people’s games , and how tech leaders can create careers and companies that align with what actually matters. Reserve your spot for the Coaching Upgrade #2 livestream. 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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Innovation Safety Nets 11:29

15 weeks ago11:29