Humility in Leadership: Mark McClain, CEO of SailPoint Technologies | Art of Leading

Mark McClain, founder and CEO of SailPoint Technologies, shares key lessons on practicing humility in leadership, continually assessing talent, and learning to adapt quickly in this Art of Leading interview with The ExCo Group‘s Adam Bryant.

Q. You’ve founded two companies. What is your leadership playbook?

A. I have a few core tenets. One is the old “there’s no ‘I’ in team.” It’s not about everybody taking all their leadership cues from me or me providing all the answers. It’s much more about me guiding a group of leaders to get the best out of all of us to help us achieve our goals.

It’s also important to be self-aware—know what you’re good at, understand what you’re not so good at, and surround yourself with people who are good at the things you’re not. Third is that change is not only good, it’s inevitable, and you should avoid becoming overly fixated on any approach to anything. People often get hung up on doing things the way they’ve been done as opposed to evaluating the principle or the value behind that approach.

Q. You spent a lot of years inside very big companies before starting your own companies. Was there always an entrepreneur inside you waiting to get out?

A. If there was, he was well hidden. I was not running lemonade stands when I was younger. My approach was more: Why don’t we just go play baseball and let Mom give us lemonade? I just wanted to be around people, and then I got elevated into leadership roles as time went on. After ten years in big tech, I became more interested in getting my arms around the whole business.

Q. What were the biggest gaps between your theory and the reality of building companies?

A. One was that if we hired great people, ideally, we should never lose them. They should want to work for us forever. What I had to learn was that great people are not necessarily great across the entire lifespan of a company’s evolution.

I may have a leader on my team who’s been awesome, but I’m not sure they’re going to be right for what’s next. And I’ve got some leaders now who are amazing but would have been terrible fits in the first five years of the company. You have to continually assess whether you not only have great people but whether they are the right fit for what’s needed at this point in time.

And it shouldn’t always be me coming to that conclusion. I would encourage people to sometimes come to that conclusion themselves. We’re so bad about separating at work. Let’s just have an adult conversation and be honest with each other, and then we can have an orderly transition.

Q. How do you hire?

A. When I ask people questions about what they’ve done, I listen carefully to whether their answer is more “I, I, I,” instead of “we, we, we, we.” With very few exceptions, nothing gets done in business today without teamwork. If you think of your accomplishments as primarily yours and don’t naturally think to give credit to others, then I’ve learned a lot about you.

Q. What do you consider the hardest part of leadership?

A. It’s knowing when it’s the right time to stick with what you know and when you need to do something differently. We’re all adapting and learning all the time. The older we get, the more experience and wisdom we should have to spot patterns and know the right thing to do. But with the rapid evolution of technology, not all of that pattern matching is going to be useful.

That’s why mentoring in every direction is so important. Sometimes it’s the people half our age who are teaching us about what is rapidly changing in technology and our culture. So you have to have humility. I’ve been doing this for 30 years, but I’ve got to learn from others because I don’t get the things that they get.

Q. When you coach and mentor people, what themes come up most often in those conversations?

A. A common theme is people holding on too hard to their perspective on an issue when they need to be more open-minded. They need to be willing to acknowledge that they may not have it exactly right and be open to considering a different view.

Another is sometimes to help them see their blind spots. If their natural strength is to be very direct with the team, then I may need to help them see that they should take a more gentle and careful approach with some teammates.

I have come to believe that we don’t necessarily have positive and negative traits. We have traits, and they show up in positive and negative ways. For example, are you persistent or stubborn? It’s the same trait, but sometimes it shows up in a positive way, and sometimes it shows up in a negative way.

Q. What were important early influences for your leadership style?

A. Like a lot of people, my leadership approach is informed by taking the best of what I’ve seen in my career and discarding the worst. A colleague in one of my early jobs had a sign in his cubicle that said: “No one is completely worthless. At least they can be used as a bad example.”

I learned early on from watching leaders who didn’t listen—they were sure they knew what to do and just marched straight ahead. You always have to have the humility to acknowledge that you don’t understand everything that’s going on. You have to learn from others but also be decisive.

We underplay the value of humility in leadership way too much. Instead, people think they have to be strong, aggressive, and assertive. I often share this quote from C.S. Lewis: “Humility isn’t thinking less of yourself, but thinking of yourself less.” A lot of leaders don’t understand that.

Being a CEO is a really important role, but they can’t put themselves in some different category. There are wildly successful businesses run by very arrogant leaders, but I don’t know if that plays for the long run. And even if it does, fine. You were successful. But did you like coming to work? Did you create an environment you wanted to be in eight to ten hours daily?

This interview with Mark McClain, founder and CEO of SailPoint Technologies, on practicing humility in leadership, continually assessing talent, and learning to adapt quickly, is part of our Art of Leading interview series featuring powerful insights from top leaders. Join the conversation on LinkedIn.

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