Left to right: Senator John Hickenlooper; 2022 Jeff Ubben Posse Fellow Alexander Robinson.
Left to right: Senator John Hickenlooper; 2022 Jeff Ubben Posse Fellow Alexander Robinson.

Ubben Posse Fellow Interviews: Senator John Hickenlooper

Fall 2022 | National

The Jeff Ubben Posse Fellows Program awards five exceptional Posse Scholars $10,000 each and the chance to spend 4-6 weeks during the summer shadowing and learning from a major industry leader. The interview below with John Hickenlooper, the U.S. Senator from Colorado, was conducted by Posse Scholar Alexander Robinson, now in his junior year at The George Washington University, who worked with Senator Hickenlooper as a 2022 Jeff Ubben Posse Fellow. The conversation has been edited and condensed.

ALEX: I’d like to start off with your childhood and your background. Could you tell me a bit about what you were like as a kid—what you were doing outside of class, throughout middle and high school?

SENATOR JOHN HICKENLOOPER: Sure. So I was dyslexic, and my mother was widowed twice before she was 40, so she had two kids by each husband. But I was young, I was eight when my father died. It was very hard on my older brother and older sister. My sister is 10 years older, my brother is eight years older. So my brother was 16… and my sister was 18. They were 16 and 18. Anyway, it was a sad house and I was dyslexic, so I was always kind of behind in school.

Anyway, I was the opposite of most of the people in the Senate. By the time they were in high school they were elected president of their class. Right? They had confidence, they were leaders from the beginning. That wasn’t me.

I was the kid that everybody picked on in third grade. By sixth grade, I had figured out how to make friends because I was a really big extrovert, and if you’re dyslexic you find these other ways of coping, I think the word is. Anyway, by the time I got into high school I kind of had my niche, which was basically that I was kind of a friend of everybody. I didn’t really have any close friends or a group of friends where I felt I belonged. But I loved sports, and my mother’s family—I grew up outside of Philadelphia—my mother’s family is a huge family, so there were a lot of cousins and family support, which was useful.

But anyway, I didn’t really gain confidence until I was just about graduating from college, and then in graduate school I began to get—to feel—that I was good at something. It was just a process of gaining confidence.

Can you tell me more about your mother and how large of an influence she was in your life?

Sure. Her nickname was “Shrimpy,” she was five feet tall. 4’11” and a half, but she said she was five feet. She always said, “Big things come in little packages.” She was very strong. Obviously, she raised four kids by herself. She was a great athlete, she got a full scholarship to go to Vassar College. It came from her father, he lost everything opening a distillery in 1933 during Prohibition. Basically, Pennsylvania turned out to be the worst state for it, just all this red tape from the Quakers. Religious state. Anyway, as the oldest child—she was the oldest of five—she had always been kind of an elder and a leader.

I think I drove her a little bit crazy, but we had a special bond. I think all my siblings were a little jealous of my relationship with my mother. I guess that’s not unusual, but my mother was relentless about treating all four kids fairly. I was just the youngest, I was spoiled, so I got to break more rules and change the boundaries.

This next one is kind of a double-question: How would you describe your current leadership style? And, who or what experiences would you say have shaped that leadership style?

So I guess my leadership style, again, I grew up as someone who essentially was very insecure and didn’t have a lot of confidence. It’s really one of the hardest things if you are an extrovert. If you gain energy by your interaction with other people, if that’s what gives you energy, and you don’t have any confidence—which is another way of saying you’re shy, shy people usually don’t have confidence—that’s really frustrating and hard because what you most want, you don’t have the confidence to go ask for it.

I can remember watching from my bedroom window seeing the kids playing pick-up basketball in the driveway next door, and all I ever wanted to do was play with them, and I didn’t have the guts. I didn’t have the confidence to go and just say, “Hey, can I play with you guys?” So I watched for years, and I finally, you know, met one of the kids somewhere else five years later and what happened? “Of course you can play.” Yeah, of course. I became friends with everyone in the neighborhood. That’s how normal people work.

So my leadership style, since I’ve come at it from a place of confidence, is largely based on trying to find the smartest, most talented people to work for me. I’ve always tried to get talented people and then I give them as much responsibility as they can handle.

And then I also try to always use humor. Like my dad, who had three major operations, got cancer when he was 37 and died when he was 40. He always said, “If you can laugh at something, it can never beat you.” I think that endures—especially in times like this, when the country’s so divided and partisan—that you gotta be able to see the lighter side of things from time to time, as serious and the issues are. So I think that’s a part of my leadership style, to keep people at ease.

A lot of these are lessons I learned as a small business person. So, when the oil and gas industry went in the tank in the mid-80s our company got sold and everybody got laid off. There were no jobs. I ended up opening this brewpub. Raising the money and putting the brewpub together.

My mother was amazingly frugal. I mean, she raised four kids and I don’t think she ever made more than $40,000 a year. We didn’t go to restaurants, we didn’t go on vacations. We didn’t do any of that stuff, but we had a pretty comfortable life. We never went hungry. Now, I always had to wear my brother’s clothes, I always had hand-me-downs, but anyway I think that the frugality and the ability to make jokes about the most difficult circumstances is something I got from my family—my mother, largely.

And I think those lessons worked in small business when I started to get into it, too. You know, if you have a restaurant and somebody comes in there, an idiot, and one of your waiters does something small, not significant, and this person thinks it’s the end of the world and they want you to buy their whole meal, and finally you say, “Well go ahead. You can say what you want but I’m not buying your meal.” And then they go out and start telling the world and all their friends what an awful restaurant you have and how badly they were treated—and you don’t hear the end of it. And you realize, what I used to say, you know, in the restaurant business you’re operating on a fairly thin profit-margin. You don’t make that much money off of each customer—but what you learn is, there’s no margin, zero margin, in having enemies.

And that’s something in politics people don’t recognize often. You know, in politics, people like to define themselves by their enemies. It’s just kind of the way it works. And so I’ve always tried to be the opposite of that. Those are kind of ways that I’m uncharacteristically different than most politicians.

That actually provides a really nice segue. You said that a core component of your leadership style is trying to find the smartest and most talented people. Sometimes smart and talented people can disagree on a number of topics. When that happens, do you always try to find compromise? In your eyes, is compromise always a virtue?

That’s a really interesting question, and there’s no easy answer to that. You know, in diversity there is great strength. So when I first got elected mayor, people were so excited to have a small business person as mayor, and it’s a strong-mayor form of government. The mayor of Denver is one of the most powerful mayors in America. The city council needs nine out of 13 votes to change one line-item in the budget. The mayor is a czar, is king.

The mayor before me, Wellington Webb, was African American, and before him it was Federico Peña, a Latino. So I made it a point to have my administration to be more diverse than any of them. I had 50% people of color and 60% women when I first started between my cabinet and senior staff.

And I say that just because when you have a diversity of people from different backgrounds, different ages and different tribes, you’re gonna get a much better balance of what’s a good idea, what’s a bad idea, how do you take a good idea and make it a better idea, and how do you anticipate bad, unintended consequences of a good idea.

It’s true that sometimes people disagree, but if you stay at it, and you keep working at it, most times you’re gonna come off with a compromise that people feel good about. So often it takes the time, and the credibility you build up in that time.

What I always say is, “I’ve never changed anyone’s mind about something that’s important by telling them why I’m right and they’re wrong.” It’s never happened. The only way you can change someone’s mind is to actually listen to what they’re saying. You know, the restaurant business is where people are really pissed off – you repeat back their exact same words, the same as couple’s therapy, and when they hear their own words in a calm voice they generally relax. They feel validated.

That’s how we get to successful compromises, when people feel they’ve been heard. And when you say someone else’s argument, when you vocalize someone else’s argument, you hear those words in a different way than when they were talking to you. I think that’s a big part of how you get to a good compromise.

I mean that’s an elected system. When you’re the mayor, in the end, you make a final decision. But I can count on two hands… well, I bet I can count on one hand the times where I made serious decisions when I didn’t have almost everybody with me, universal consensus. Some groups, like the Quakers—my ex-wife was a Quaker—they work on consensus. For all important decisions—you have to get everybody. It’s hard, it takes a lot of time.

This is more of a personal question that I’m really interested in, but how might you compare the struggle of the “Founding Fathers” in colonial America to the current struggles faced by regular working-class Americans?

Well… “History never repeats itself, but it rhymes.” That’s a famous old saying, I can’t remember who said that but it might’ve been Ben Franklin. I think history is incredibly valuable because many of the same conflicts we still have, rich versus poor, the rights of individuals… You know, the Founding Fathers, half of them didn’t believe in slavery. And it was a religious belief for them, that this was something that is wrong. Throughout most of history, conquering countries have enslaved the populations that they conquered. But in this country, a significant number of the Founding Fathers felt that was immoral and completely unacceptable. I think those debates on universal civil rights continue to this day. That’s a lot about what we’re debating.

Thank you so much. I know you have to leave now but I very much enjoyed this.

Of course.

Read More:
Ubben Posse Fellow Interviews: David Solomon
Ubben Posse Fellow Interviews: Christine Squires
Ubben Posse Fellow Interviews: Stéphane Bancel

Meet the 2022 Jeff Ubben Posse Fellows.