Years ago, before I went to college, I had dinner with a billionaire.
I won’t name him, but I remember feeling completely out of my depth. Here I was, trying to figure out what to major in, what path to take, and this incredibly successful person gave me some advice that I have never forgotten. He said I should get a general degree and spend my time learning how to think, rather than specializing.
Critical thinking, he believed, was the most important skill I could develop. Everything else could be learned later.
I think about that conversation all the time, especially when I’m building teams. Because that advice, the idea that how someone thinks matters more than what they already know, it’s shaped my entire philosophy on hiring.
Hire for Informed Opinions, Not Just Right Answers
I once interviewed someone who’d worked at a company I knew really well. I won’t get into specifics about the person or the organization, but I asked them a simple question during the interview: What did they honestly think about how that company approached the market? Their methodology, their strategy, the whole thing.
The first answer was textbook. Polished. Safe. Exactly what you’d expect someone to say in an interview.
So I asked again.
I could see them trying to figure out what I wanted to hear. Navigating the moment. I wasn’t looking for the “perfect answer.” I wanted their informed perspective. The second time, they opened up. They dissected the good and the bad of the organization with real insight. That was the turning point.
Right there, I knew this person could think independently and make decisions without needing someone to tell them what to believe.
That’s the type of person I want on my team.
I hire people who are respectful but opinionated. Problem solvers who aren’t afraid to have a point of view. Sure, deep expertise matters for some specialized roles. But in my experience, it’s more valuable to have someone who’s going to flex with the dynamic needs of a role. Someone who can learn fast and apply critical thinking to whatever shows up.
“This Is Early Thinking. I Expect You to Challenge It.”
That’s how I start most of my strategic discussions with my team.
I joke with them that they challenge most of my ideas. And they do. Not because they’re being difficult or disrespectful. They do it because I expect it from the outset. I want my team to cover my blind spots. The healthy debate should go both ways.
Here’s the thing. A lot of people say they want independent thinkers. But I know from experience there are two types of leaders on this issue. Those who can genuinely handle having their ideas challenged, and those who pretend they want feedback only to just do it the way they originally wanted anyway.
I’m the first type. At least I try to be.
If you’re surrounding yourself with people who only agree with you, you’re not building a team. You’re building an echo chamber. Echo chambers don’t help you avoid costly mistakes or build better strategies. Real challenge does.
The Airport Test and Learning Mindset
You don’t need to be best friends with everyone you work with, but I have found that it is better for everyone if you at least get along.
There’s this concept from consulting called the airport test. Could you survive being stranded in an airport for 12 hours with this person? If the answer is no, that’s probably a red flag.
For me, I assess this by asking broader questions during interviews. I want to understand who someone is beyond their professional life. What they care about. What makes them tick. The resume tells me what they’ve done, but it doesn’t tell me who they are.
Create the Environment Where People Actually Thrive
Hiring the right people is step one. But if you don’t create an environment where they can thrive, you’re wasting everyone’s time.
For me, this comes down to a few basics.
Give everyone a voice. I seek out opinions at all levels to make sure people feel empowered to push back on bad ideas and bring forward new perspectives. It can’t just be the senior people in the room who get heard.
Give real feedback. The people I hire want to achieve more and grow in their roles. I often say, “Feedback is a gift, and every day is Christmas,” because I genuinely believe feedback should be given more often. That makes it less of an event and keeps the iteration process moving. People get better when they know where they stand.
Give people scope to own. People want to be able to own something and point to their contributions over time. Providing a project with clear boundaries gives people work they can actually be proud of.
Keep it fun. I like to make people laugh at work. I can be very serious when the situation calls for it, but leaders also need to know when to relax and have a laugh. I use self deprecating humor a lot. My team needs to see that I don’t think I’m perfect, because I’m not. We spend a significant portion of our lives at work. It needs to be fun to keep coming back.
Build followership by investing time. I spend real time with my people to understand what’s important to them. Not just professionally, but what they want out of their careers and lives. Then I try to build roles around them to make sure their aspirations are being met. Not every role can be custom built, obviously, but the effort matters.
Why This Matters
I keep coming back to that dinner conversation with the billionaire. Critical thinking. Informed opinions. Creating the conditions for people to grow and contribute.
The teams I build don’t just perform. They want to be there. They challenge me. They challenge each other. They get better over time because the environment rewards learning and honest feedback.
And honestly? That’s the only kind of team worth building.