Author Talks: The biggest misconceptions about leadership

In this edition of Author Talks, McKinsey’s Artemis Vallianatos speaks with Mike Grossman, six-time Silicon Valley CEO and McKinsey alumnus, about Failure Is An Option: Reflections of a Silicon Valley CEO (Simon & Schuster, July 2026). Drawing on nearly three decades as a leader and lifelong learner, Grossman challenges the notion that hard work alone determines success. Instead, he argues that integrity, adaptability, and learning from failure are what truly define effective leadership. An edited version of the conversation follows.

How did realizing that hard work doesn’t always lead to success change how you define success?

I gradually learned to see myself and to define success based on the quality of the work rather than the outcome. That was the biggest change. I also came to the view that success is in the eye of the beholder. Society dictates that success looks a certain way. The truth is, certainly in a business context, sometimes success is taking a company public. Sometimes success is survival. And sometimes success just means trying your hardest in a very difficult situation.

I realized that I shouldn’t define myself based on outcomes. I should define myself based on the quality of my or the team’s input. You can’t really control the result; therefore, defining yourself in terms of the result isn’t a very constructive approach.

How do you lead when luck plays such a large role in success?

Luck plays an enormous role. But the implication is that you need to be honest with your teams about your inability to control the outcome. Try to do as good a job as possible and adjust along the way. Build a great cultural environment because if people really love working for the company, when adversity strikes—and it always does—people will stay. That’s the most significant implication: You really have to think about the culture and your way of doing things. If you act in the right way, then you can withstand the ups and downs.

Luck is the way I got the job at McKinsey. The person who was conducting my interview had been interviewing nonstop. I spontaneously cursed in the interview to get the associate to become much more interested in what I had to say.

I flew out to San Francisco for my next round of interviews, and I ended up getting the job. Even more profoundly, getting that job enabled me to secure a different job a couple of years later in Australia, where I met my wife. My kids now exist because I cursed in an interview all those years ago. That wasn’t a plan; that was luck.

You once chose a personal relationship over a pivotal professional one. Would you make the same choice today? Why?

A person on the verge of being a lead investor told me that unless I took over as CEO and effectively fired my best friend and business partner, he wouldn’t invest. I said, “No.” I was going to stick by my best friend and business partner.

I would absolutely make the same decision again, and I wouldn’t hesitate. Fiduciary duty really does matter. That’s a considerable responsibility for any CEO. But there are limits to what I’m willing to accept, and unethical behavior is something that I’m not willing to put up with. Firing my best friend and business partner just to raise an initial round of funding felt unethical. Most of the time, these issues are shades of gray.

One of the other stories I write about is a situation where I knew the sale of a company was clearly the right fiduciary answer. In that case, we went ahead and sold it. I felt like that was acceptable. Yet if I thought employees or customers would hate the result, I would not be inclined to complete a deal. I’d rather stick in there and talk to the team openly and authentically about that because a deal involves a lot more than the money.

You write about a missed opportunity that had significant financial outcomes. Looking back, what emotion stays with you most?

In a situation where an offer was made for a company, I was too aggressive in the negotiation. The deal fell apart, which had financial implications: opportunity costs for me, my father, who was one of the cofounders, my best friend, and the team at large.

Regret is the emotion that stays with me. Certain mistakes stay with you, and that was one of them. I accept it, and I’m glad to have learned specific lessons that I applied afterward. There are moments at 2 a.m. when I wake up, stare at the ceiling, and lament the fact that I made that decision.

Do we fundamentally misunderstand what the job of a CEO or a CEO/founder actually is?

People understand what the job of CEO involves. It involves delivering bad news periodically or making painful decisions. Certain aspects are not well understood or discussed much—most profoundly, the weight of the CEO’s job on not just the team but, indirectly, on the team’s partners and family members who depend on that person.

The traditional Hollywood narrative would be that a person has a transformative idea. Things go well, then they hit adversity, then they get through the adversity, and there’s enormous success. But that’s not really how life works. Life bounces around.

Usually, you’ll do well and do less well in some sort of random sequence. That’s been my experience, and that’s the typical experience that entrepreneurial companies and CEOs have.

How do you know when you’ve crossed an ethical line?

A lot of decisions fall into a shade of gray: Something may be the best decision from a financial perspective, but not so from a constituency perspective. Those are difficult moments, and you have to optimize for financial results. If you’re empathetic and you care about your team and your customers, it feels challenging not to optimize for them. It’s personal. For me, one of the key values is integrity without compromise. There are situations where deciding something for financial benefit crosses that threshold. Integrity needs to win. The people I’ve worked with, people who have invested in me and the companies I’ve run through the years, would share that perspective. There’s a broader, long-term view. These are very difficult trade-offs, and whenever you sell a company, you give up something, even if the deal is great. A lot of what you’ve built will be disrupted immediately, and it doesn’t feel so good.

Which voice do you hear in difficult moments?

I consider myself enormously fortunate that I met Bill Campbell [former CEO of Intuit] and was mentored and coached by him. When I’m confronted with difficult decisions, I think about what Bill Campbell would say. But mostly, the voice I hear is my own.

What has leadership taught you about human nature?

I’m surprised at how unselfish people can be. But if you have a really great group of folks who are values-driven and an organization that really “walks the walk,” it is surprising how people perform when confronted by adversity—and how empathetic, and considerate, and kind they are when times are tough.

The best moments are when times are tough. It may not seem that way when you’re going through it, but retrospectively, it’s amazing what people can accomplish when they’re working together and thinking about the larger group and not just themselves.

How did your McKinsey experience training contribute to the way you lead?

McKinsey had a significant impact on something that I’ve done through the years as a leader. There was something specific I learned at McKinsey about storytelling. It’s related to the way that [PowerPoint] decks were written and how there was a storyline, and you had to be very thoughtful and rigorous in defining that storyline. That has really impacted me.

Running companies over the last several decades made me think that whenever I’m communicating anything to any audience, I want to be very intentional about how I explain what I’m trying to explain. I’ve also tried to share that sensibility with people on the various teams I’ve led.

Storytelling is a really important part of being a CEO. So in every company, the way that decks are written—that storylines are written—is something that’s treated with great rigor.

What does fact-based optimism look like in practice?

I have an analogy or metaphor of a football kick returner who catches the ball and starts running down the field while defenders are trying to tackle him. Every step of the way, the returner is trying to evaluate the right decision based on this dynamic and shifting fact pattern.

Is it the right decision to run over a person? Is it running underneath the person? Is it running to the side? Is it getting behind a blocker? Sometimes you have to run sideways. Sometimes you even have to run backward before you can run forward. That’s the image that I have in mind. At every step, you need to evaluate the facts. You need to analyze in an efficient way. And in some fundamental sense, you have to be optimistic.

You must think about how you can leverage what you have to make the best possible decision. You can be realistic: You might get tackled. But that’s not the mindset. The mindset is how do you avoid getting tackled, and how can you do everything you can in that regard?

That sentiment was certainly reinforced by time at McKinsey. I think of business as just an endless sequence of problem-solving exercises. You’re trying to analyze data in a structured way and then figure out the answer. It’s all about problem-solving from an optimistic but realistic perspective. Sometimes things don’t work. Sometimes you have to pivot. But you always try to figure out a way to move forward.

When I first had the chance to interview with McKinsey, I had no idea that it would have such a profound impact on the rest of my life. My entire trajectory changed because I went to that interview, and in the end, the interview went well. I learned a lot on the business side, but even my personal life was affected by that choice in ways I couldn’t anticipate. I feel enormously grateful for that.

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