Article

A Conversation with Dr. Richard Hagberg, the Silicon Valley "CEO Whisperer"

July 6, 2025

Reprint from Thought Economics, A Journey of Intellectual Capital

In this interview I speak to Rich Hagberg, Ph.D ., often referred to as “Silicon Valley’s CEO Whisperer.” Richard is a trained psychologist who has spent the last 40 years of his career as an executive management coach for over 6,000 executives. Since 2009 he has worked with companies like Tinder, Twitter, Dropbox, MixPanel, Zendesk, Quora, Asana, Pinterest, Salesforce, Munchery, Reddit, Gusto, Cruise, Tinder, Optimizely, Instacart, Patreon, Nerdwallet, and Super Evil Megacorp (it’s a gaming company). He is the co-author of Founders Keepers, Why Founders are Built to Fail & What it Takes to Succeed .

Q: What do you mean, when you say all founders are built to fail?

[Richard Hagberg]: I think that by saying founders are built to get the rocket off the ground, what we’re really acknowledging is that many of them never get it into orbit. Fewer still get it to the moon, and almost none make it to Mars. The problem is execution. Founders are idea people — driven, persistent, individualistic loners and contrarians. It’s hard for them to adapt because they have strong views. It’s hard for them to work through others because they’re independent and used to getting their way. So they don’t delegate and they over-control. They see structure and systems as bureaucracy. They often lack self-awareness — of how they impact others, what they’re good at, and what they’re not. And a lot of them just can’t handle the stress. I mean, people ask me, “Should I do a startup?” And I say, “Well, how important is work-life balance to you?” And if they say anything other than “It’s not important,” I say, “You shouldn’t do it.” Because it’s a killing field. So basically, let me summarise that by saying: the skills that get them to one point won’t carry them the rest of the way. We talk about the ticking time bomb. The ticking time bomb is these very characteristics — when you’re trying to scale, and things are getting more complex, and you have to work through other people — they blow up.

Q: Why do we still believe in the genius jerk archetype?

[Richard Hagberg]: I was just writing something on this earlier in the week. I was looking at examples like Steve Jobs — before he got fired, he was a genius jerk. He got fired, started NeXT Computer, and it didn’t take off. Then he got involved with Pixar, and apparently one of the Pixar co-founders helped him understand the importance of empathy. So when he came back to Apple, he was more willing to adapt, to work through others — with people like Jony Ive, Tim Cook, and others. He was never a choir boy or a saint. The same thing applied to Gates. In the early days of Microsoft, Gates was a terror. But after around 2000, he mellowed a lot. Even Bezos — I mean, around the time that book came out trashing Amazon’s culture, Covid was hitting, his people were under incredible stress, and he was getting all kinds of feedback. So there are these transformational moments that often change people. But look, there are a variety of reasons why founders get misled. Successful, abusive, aggressive people are highly visible — we think of Elon Musk as a good example — and we dramatize these figures. We looked at 122 founders and compared them from the perspective of multiple invested capital, and the most successful ones didn’t fall into that category. They weren’t choirboys, but they didn’t fall into the same patterns either.

Q: How can we encourage founders to be more self aware?

[Richard Hagberg]: … you’ve got to create a psychologically safe environment where people on your team feel able to give you feedback. If they feel intimidated, they’re not going to tell the emperor — or empress — that they have no clothes. So that’s the first thing. The second is, it’s helpful to get objective heat back. These people listen to data. When I came to Silicon Valley, 360s had just started, and I used to give talks about how important a tool it was — because the engineers I was coaching listened to data. Whether it’s 360 feedback, an objective engagement survey, or an employee survey, it helps them understand their impact and what’s really going on in the organisation. Having good coaches and mentors who will tell truth to power — that’s the business I’m in. I’m in the business of telling truth to power. And there are two things. One is that unless you learn and grow continuously, you’re probably going to end up as one of the 90% who don’t make it. The second is — and I mean, I’m a serial entrepreneur as well as a psychologist — thank God I learned to meditate when I was 19. That gives me a bit of distance from my behaviour. It lets me observe things with more clarity. And because startups are so stressful — such a killing field — it undermines decision quality and brings out bad behaviour. My Master’s thesis back in the ’70s was on meditation; my doctoral thesis was on stress and its impact on people. There’s been plenty of research since then that’s validated it, and I see it all the time. When these people are under stress, they make bad decisions. They get reactive. One of the key findings in our conclusions is that the unsuccessful founders were more reactive. They weren’t measured. They weren’t deliberate. They didn’t make decisions based on facts — their emotions carried them away.

I ’ve got to tell you a story. When I went back to graduate school, one of my mentors called me into his office and said, “Rich, there’s one little piece of advice I’d like to give you.” And I thought, oh boy, here it comes. Then he said, “Rich, sometimes you treat a wisp of intuition as though it were a four-lane highway.” It’s not that you shouldn’t trust intuition — it’s that you need to validate it. And to validate it, you have to run a decision-making process that’s grounded in facts, built around having multiple alternatives, and involves actively seeking those alternatives from other people. And then — because everyone is biased, and the research on cognitive bias is very compelling — you have to run a disciplined process to ensure the facts and alternatives actually surface.

Q: What about the effectiveness of the boards around these founders?

[Richard Hagberg]: I’ve talked to board members at companies where the leader was pushed out for unethical behaviour or ended up indicted. It often comes down to the fact that they waited too long — guided by greed — to address dysfunctional behaviour that could sink the company later. That’s the first thing. The second is that many boards today, especially startup boards, are dominated by investors who don’t have operating experience. So they try to hold people accountable, but only for the numbers — not for their behaviour, and not for their actions as leaders. Another thing I see is that because the board is more challenging than supportive, it ends up encouraging founders to exaggerate, to bend the truth, and to feel unsafe being honest about the problems — which means the board can’t actually help. And a lot of investors aren’t able to help anyway — they can’t give the kind of strategic support that’s really needed. Founders want help with strategy, but they want that help from people who’ve been there and done it — people with real operating experience.

Q: What is the role of the coach, or mentor, in the founders’ journey?

[Richard Hagberg]: In my mind, there’s a difference between being a coach and being a mentor. I’m a psychologist, but I’ve also been a founder, and I’ve been studying leadership since 1986. So at times, I’m using the psychologist’s lens to peel the onion — to understand what’s going on inside and where they’re blocked. At other times, it’s clear that a lot of them lack best-practice experience. They’ve never had a boss, they’ve never been a boss, and they don’t know how accountability works. They have no models, no frameworks. That’s where mentors can help — with frameworks. But if the mentor is only drawing on their own experience scaling their company, it might not translate. It could be a totally different kind of company with a completely different business model. Those mentors are great at offering advice on what worked for them — but they’re not always as helpful in answering questions like: what do we know about how to make good decisions, or how to build effective teams?

Q: How do founders avoid burnout?

[Richard Hagberg]: I think you have to make your own physical and mental health a real priority if you’re going to make it through. When you take a step back and look at what we learned in the book, it’s essentially survival of the fittest. And fitness means not resorting to things like alcohol and drugs to cope with stress — which so many people do — and making sure you get enough exercise and enough sleep. People are proud of how many hours they work — it’s almost like a badge. And it’s crazy, because I can see how it undermines both their judgement and their health. I’ve probably been burnt out three times over the years and had to do a reset. And each time, I’ve had to ask: what am I doing that’s pushing me over the edge here? Where can I set boundaries? And if you’re too demanding — if you only focus on results, put constant pressure on people, and make it unsafe for them to push back — you’ll burn out your team. I have a client right now who’s been pushing hard to hit financial goals, and multiple members of the senior management team have thrown in the towel. They’ve said, “That’s it, I can’t deal with this, it’s destroying me.” What’s interesting — and this is something we haven’t talked about — is that the successful founders don’t necessarily have high emotional intelligence, but they have better emotional intelligence than the unsuccessful ones. And that allows them to read people, to check in on their wellbeing, to ask what’s getting in the way of performance. The unsuccessful ones have no empathy — they just drive people. They treat relationships as transactions. For them, it’s all about tasks, not about people. But it’s not a machine.

Q: Do you see a relationship between neurodiversity and the most successful founders you have worked with?

[Richard Hagberg]: I’m not an expert on the spectrum — but I suspect that people who get caught up in their internal world of ideas, and aren’t aware of people, emotion, team dynamics, and all that, who are just purely idea people — it really gets in the way. That said, I know one very successful founder who’s clearly Asperger’s, and he’s made a real effort to learn how to be a leader. It doesn’t come naturally to him — it’s not instinctive — but he works at it. People often ask, in a whisper, “Do people really change?” And I say, look, people may not change their fundamental personality, but they can change their behaviour. That said, how much they can change is limited. And when people ask how much, I say, well, on a 10-point scale, if you really work at it, you can probably move about 3 points. So if a job requires you to be at an 8, and you’re a 4, it’s going to be tough. And that’s where execution becomes a problem for many founders. Because founders are creative, idea-driven people. The insights they get, their willingness to challenge tradition, and their awareness of the market — that’s what fuels them early on. They’re divergent thinkers. They generate possibilities. But at a certain stage — when the company enters the traction or fast-growth phase — you need to bring focus to the organisation. And they get distracted by shiny objects. Any new idea just sweeps them away.

Q: What is the relationship of wealth to the journey of your founders?

[Richard Hagberg]: it’s something I tell my clients — especially when I’m assessing whether I’ll work with someone. I ask, “What’s your goal? What’s your vision?” And if they say, “I want to grow a million-dollar company,” or, “I want to do an IPO,” I say, “No, but what’s your vision?” I know a venture capitalist who says when someone gives that kind of answer, it’s an immediate knockout. My belief isn’t that greed doesn’t exist — it does — but when it’s the primary driver, and there’s no passion for doing something meaningful or making an impact, they’re much less likely to make it through the tough times. You need to be willing to hit the wall, and hit the wall, and hit the wall — again and again.

If you’re curing cancer, you’ll be willing to hang in there. Or if you believe you’re building a technology that could change the world — like AI — then you’re less likely to give up, and more likely to understand that people aren’t just cogs in the machine.

Q: What does legacy mean to you?

[Richard Hagberg]: I’ll answer that by telling you a story. One of my clients worked for a big international pharmaceutical company. He wasn’t a founder. He wanted me to attend a meeting he was facilitating so I could observe him. I got to the meeting, and a guy sat next to me. The tables were arranged in a U, and he was sitting right beside me. I noticed he was staring at me. I turned and said hello, and he said, “You don’t remember me.” I said, “Help me out — remind me.”

He said, “Well, 10 years ago we worked together.” And all of a sudden, I realised who he was. He had grey hair now — I remembered him when he didn’t — and I said, “Oh yeah!” Then he said, “You changed my life.” I said, “I did?” And he said, “Yeah.” I asked, “What did I do? What did I say?”

He said it was just one thing. He wasn’t an assertive guy. He told me, “You said I didn’t have the right to always get what I want, but I did have the right to be heard.” And I was like, “Okay.”

I’ve heard stories like that a lot. Sometimes they don’t remember it the same way I do, but you never know what you might say or do that changes a single individual — and that person may go on to do something really significant. When I was in college, I was an idealist. I was a protestor and all that. And now, my goal is to help people make change. I help my clients unpack the problems and challenges they’re facing — and hopefully, that makes a difference.

About the Author

Vikas Shah MBE DL is an entrepreneur, investor & philanthropist. He is CEO of Swiscot Group alongside being a venture-investor in a number of businesses internationally. He is a Non-Executive Board Member of the UK Government’s Department for Business, Energy & Industrial Strategy and a Non-Executive Director of the Solicitors Regulation Authority. Vikas was awarded an MBE for Services to Business and the Economy in Her Majesty the Queen’s 2018 New Year’s Honours List and in 2021 became a Deputy Lieutenant of the Greater Manchester Lieutenancy. He is an Honorary Professor of Business at The Alliance Business School, University of Manchester and Visiting Professors at the MIT Sloan Lisbon MBA.

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Why smart leaders are the hardest to to work for.

Why Smart Leaders Struggle with People

By Rich Hagberg • March 30, 2026

Some of the smartest leaders you will ever meet are also some of the hardest people to work with. They are fast, perceptive, and unusually strong at solving hard problems. They see patterns others miss. They cut through ambiguity. They grasp systems, strategy, and complexity at a very high level. In many cases, those gifts are exactly why they became founders, technical leaders, or senior executives. And yet many of these same people leave a trail of strained relationships behind them. Their direct reports feel unseen or intimidated. Peers experience them as dismissive, impatient, or controlling. Their bosses admire their intellect but hesitate to trust them with broader leadership responsibility. At home, partners often feel emotionally alone. Over time, the leader becomes puzzled. They know they are smart, committed, and often right. So why do people keep pulling away, withholding the truth, or failing to fully follow them? The answer is that many high IQ leaders are working from an incomplete model of effectiveness. They assume that if they think clearly, argue logically, work hard, and produce results, the rest should take care of itself. That model can work for a long time in school, in technical roles, and in the early stages of a company. But eventually leadership becomes less about the quality of your own mind and more about your ability to work through the minds, emotions, motivations, and limitations of other people. That is where many smart leaders start to fail. The Core Problem Intelligence is not the problem. It is an asset. The problem is that intelligence often creates distortions. It can make a leader overestimate the power of logic, underestimate the importance of emotion, and develop habits that quietly damage trust. It can also create a subtle arrogance. Not always the loud kind, but the quieter assumption that if other people are slower, less rigorous, or more emotional, they must be the problem. Once a leader starts living inside that assumption, interpersonal trouble becomes almost inevitable. Five Common Patterns 1. Overreliance on reason Many bright leaders treat relationships as if they are mainly cognitive systems. If there is disagreement, they explain more. If someone is upset, they analyze the issue. If morale is low, they offer strategy. If a direct report feels discouraged, they give solutions. In their minds they are being helpful and efficient. But the other person often feels bypassed. Their emotional reality is treated as noise rather than information. Their need to be heard is mistaken for a need to be corrected. This is a major blind spot in analytical leaders. They often do not realize that understanding is not the same as persuasion, and problem solving is not the same as relationship building. A person can agree with your logic and still not trust you. They can accept your decision and still lose commitment because the relational cost was too high. 2. Impatience High horsepower people often process faster than the people around them. They see the answer early. They get bored by slower thinking, frustrated by repetition, and irritated when others need more context than they do. This can make them decisive and productive. It can also make them hard to work with. They interrupt. They jump ahead. They finish other people’s sentences. They push past concerns before others feel understood. They make those around them feel slow, clumsy, or not worth listening to. This teaches the organization something dangerous. It teaches people that the leader’s mind is the only one that really counts. The safest strategy becomes speaking briefly, deferring quickly, or waiting until the leader has already decided. Then the leader complains that the team is passive or not taking ownership. What they often do not see is that the culture has adapted to them. 3. Emotional underdevelopment hidden by cognitive strength Very bright people can use intellect as a defense against emotional discomfort. They can analyze instead of feel. They can explain instead of reflect. They can argue instead of absorb. They can move to abstraction when the deeper issue is shame, fear, insecurity, hurt, or loneliness. They are often unaware this is happening. They do not experience themselves as defended. They experience themselves as rational. But leadership requires emotional range. Not sentimentality. Not therapeutic language. Real range. The ability to notice your own reactions before they control your behavior. The ability to tolerate feeling wrong, uncertain, criticized, or less competent than you want to appear. The ability to stay present when another person is disappointed, anxious, or angry without immediately shutting it down, fixing it, or counterattacking. Leaders who cannot do this often become brittle. They look composed until challenged in just the wrong way. Then out comes defensiveness, coldness, contempt, withdrawal, or overcontrol. 4. Low interpersonal curiosity Smart leaders are often highly curious about ideas, products, markets, and strategy, but not necessarily about people. They know how to interrogate problems, but not always how to explore another person’s inner world. They ask what happened, but not what it felt like. They want the conclusion, not the hesitation. They want the output, not the psychology. People do not trust leaders simply because they are competent. They trust leaders who show that they are trying to understand them. Interpersonal curiosity communicates respect. A leader does not have to agree with someone to make that person feel seen. But when the leader skips that step, people feel reduced to functions rather than treated as human beings. 5. Weak awareness of impact Many smart leaders are genuinely surprised by how strongly people react to them. They tell themselves, “I was just being direct,” or “I was only asking a question.” In their own minds, intent carries most of the moral weight. If they did not mean harm, then the reaction seems excessive. But leadership does not work that way. Impact matters because power magnifies everything. A passing comment from a founder can ruin a weekend. A skeptical look from a senior executive can silence a room. A blunt critique can stick in someone’s head for months. High IQ leaders often underestimate this because they evaluate themselves from the inside while everyone else experiences them from the outside. That gap sits at the center of many 360 feedback problems. The Identity Trap There is another layer here. Some smart leaders have been rewarded for being exceptional for so long that they quietly build their identity around being the smartest person in the room. They may not say it out loud. They may even dislike arrogance in others. But inside, being quick, insightful, and right has become central to their sense of worth. Once that happens, other people’s competence can feel threatening. Feedback becomes harder to absorb. Collaboration becomes more performative than real. The leader listens selectively, especially when they believe the other person is less capable. They become invested in remaining the mental center of gravity. That is a dangerous place to lead from. It turns intelligence into status defense. It makes humility feel like loss. It makes genuine curiosity harder. And it makes the leader lonelier than they realize, because very few people feel close to someone who always has to occupy the top intellectual position. The Shift That Matters The good news is that these problems are workable. In fact, smart leaders often improve quickly once they see the pattern clearly. Their intelligence then becomes an ally rather than a shield. But improvement requires a shift in model. Leadership is not just about being right. It is about creating enough trust, clarity, and psychological safety that the best thinking of the group can emerge. Your job is not merely to contribute your intelligence. It is to increase the total intelligence of the system. That means treating emotions as information rather than interference. It means becoming curious about your own interpersonal signature. What happens to people in your presence when you are under pressure. Do they get more open or more cautious. More honest or more political. More energized or more tense. Those are not soft questions. They are the real scorecard of leadership impact. It also means slowing down your certainty just enough to make room for other minds. Ask one more question before concluding. Stay with the other person’s frame a little longer. Notice when you are moving to solution because you are uncomfortable with uncertainty or emotion. Let people finish. Reflect before rebutting. And it means understanding that warmth and strength are not opposites. Many analytical leaders fear that becoming more emotionally intelligent will make them softer or less respected. The opposite is usually true. Leaders become more effective when people experience them as both rigorous and fair, both clear and human, both demanding and safe enough to tell the truth to. Practical Experiments A few simple practices can help. In your next one on one, spend more time understanding than advising. In your next disagreement, summarize the other person’s view in a way they agree is accurate before stating your own. In your next leadership meeting, track how often you interrupt, redirect, or signal impatience. After a difficult conversation, ask yourself not only whether your point was valid, but what emotional residue you likely left behind. Ask two trusted people what it feels like to disagree with you, and listen without defending. Final Thought Human beings are not engineering problems. They are not solved by superior reasoning alone. They need respect, steadiness, dignity, trust, and emotional attunement. That is why so many smart leaders struggle. Not because they are too intelligent, but because they have leaned on the wrong part of themselves for too long. At a certain point in leadership, your mind stops being the main differentiator. Plenty of people are smart. What becomes rarer is the ability to combine intelligence with self awareness, candor with sensitivity, high standards with trust, and authority with emotional maturity. That is when a smart leader becomes someone people actually want to follow.