"The Best Leaders Are Obsessed With The Nuances Of How Their Team Works Together"

Andy Stefanovich , who has held many leadership roles as an entrepreneur, advisor, board member and investor, shared his key leadership insights in my latest "Art of Leading" interview. Subscribe here to receive future interviews.?

Q. You’ve worked with many organizations and leaders over the years. What are the themes that come up most often when you give them advice?

A. It is not about the P&L, the strategy, shareholder value or OKRs. Those are fundamental to business, of course. But I think of those as below-the-line issues, and I focus instead on the above-the-line issues that are more qualitative and more human—like the comfort level that leaders have in their own skin, their acceptance that they are imperfect, their curiosity for the market and the world at large, and how they hear what their team and customers are saying. It’s about always seeking a higher ambition and a higher clarity. That’s what I work on most with leaders. ??

Q. One of the defining features of the leadership field is that there are so many mixed messages. As just one example, leaders are told that they should be confident but also humble. How do you think about that?

A. Leaders need to have a “reverse reflex,” as I call it. There is a persistent expectation in business that leaders should have all the answers. When they are right, they are hailed as visionary. But the next level of leadership requires looking in the opposite direction, and to always be questioning. I worked with a leader of a massive holding company that owned hundreds of marketing and communication companies. He once showed me a little piece of paper that he kept in his pocket. It read, “They may be right.”?

It was his constant reminder to himself to listen carefully to his leadership team and pressure-test his own thinking. “I’m smart enough to convince myself of anything,” he said. “And I need to really understand that the people on my team are often more right than I give them credit for.” That’s real confidence. The best leaders are obsessed with the nuances of how their team works together. They don't underestimate the work. They are students of it and they work at it every day. ??

Q. What other frameworks do you use when you work with leaders?

A. I talk about the three Ps of leadership. The first is providing passion from the back. You believe in your team and you’re empowering them and making sure they have what they need to succeed. The second P is for panic—though it’s a purposeful, healthy and intentional panic. You’re in the weeds with the team, going deep and low on detailed issues when your help is needed to get the work done.?

The third P is for purpose, and pulling people forward with clarity around the purpose. An incredibly successful VC client and friend once told me, “Every day I'm trying to bring more clarity and more ambition to our purpose." That is a singular job every day.?

Another approach I like to use is to ask leaders to take a full hour to write their answers to these three questions: “What do you believe? What do you trust? What do you know?” After they are finished, we talk about what they wrote, and I ask them, “So what can you take from what you wrote that might help you think about what you’re doing as a leader?”?

The language of that question is important because it helps create some distance to help you think more holistically about how you lead beyond managing your calendar. It helps leaders start a conversation with themselves, which they can then continue with their team.

Q. What were important early influences for you?

A. My mom and dad were first-generation immigrants. They didn’t have high school or college degrees. My dad went on to have a good middle-management run at General Motors, including as a kind of chief of staff for the executive team. He always lived in the shadows of these educated, formal and polished professionals, and my dad was just an absolutely imperfect being. He was passionate and vocal and loud and caring, the kind of guy who would hug you too long.?

He was just himself at the purest level. And I saw how he did that and how people received that, and I saw how important it was to these often inhuman companies. When my dad would do something even slightly human, people would receive it as if it were a new horizon. And so, when he did big things, it moved the needle of cultures. My mom was the supporting cast to him, and they did that for 43 years.?

My in-laws are also successful entrepreneurs, and I learned from them that the way to have the greatest impact on companies is not to do it from the inside, but instead to do it from the outside as an entrepreneur. That way, you can have more freedom to work in creative ways that provide them the support they need. ??

The last thing I’ll mention is that space and place mean a lot. When I was growing up, we lived in Grosse Pointe, Michigan—a very toney, privileged little suburb of Detroit. We were middle class, which was an anomaly, because all my friends came from wealthier families. Growing up in that town gave me the space and freedom to be a creative kid, ride bikes with my friends and play sports like tennis, golf, and swimming.?

But I would also venture into Detroit and see another side of life. So I had that experience of being safe but also understanding what was not safe and how to explore that. Whenever we walked out of the house, my parents would say, “Love you. Be careful.” ?And we say it over and over to our children. It’s our family motto because it means we love you, and go have fun, learn and explore, but be careful.?

Q. I'm sure you've done a ton of hiring in your career. What questions do you ask job candidates?

A. My first is, where do you come from? Give me your origin story—tell me about your grandparents, tell me about your parents. Sometimes I even ask about the origins of their last name. If they know it, that tells me that they are curious about their family’s history, and that they revere what their grandparents and parents did for them. I want to see that respect.?

Then I will ask them to tell me their own story. I want to understand the fabric of the person. I listen carefully to how they tell the stories of what made them who they are. And finally, I’ll ask them where they want to go in their career. What’s their ambition? What does the future hold for them? ?

If you put yourself in their shoes and consider that your job is to help them become the best version of themselves at a personal and professional level, there is going to be an enormous lift in their capabilities. That’s where you should concentrate your energies, and they will develop their professional skills as a result. If you live in that space, you'll find that people will be committed to you and will be your friends, not just colleagues, over a lifetime.

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