I recently interviewed Senator Heidi Heitkamp on my podcast, Thirty Minute Mentors. Here is a transcript of our interview:

Adam: Our guest today is a former United States Senator. Heidi Heitkamp is the first woman to be elected to the United States Senate from North Dakota, and is a Democrat who was elected in a deeply Republican state. Senator Heitkamp, thank you for joining us.

Heidi: Thank you for having me. What fun?

Adam: I'm excited. You grew up in Mantador, North Dakota. There are small towns and there are small towns. In the last census (I'm going to throw this out for listeners), Mantador reported a population of 67 people. Can you take listeners back to your early days? What experiences and lessons shaped your worldview and shaped the trajectory of your success?

Heidi: Well, you grow up in a town – At the time that I lived in Mantador, there were 90 people. And my family was 1/10 the population. But here, I'm going to give you an example: When I went to law school, I went to law school in Portland, Oregon. And this is back when the Post Office functioned a little differently. I challenged my classmates to send a postcard or send a Christmas card home to me that just had ‘Heidi’ with the zip code 58058, which is the zip code of Mandator, North Dakota. And I took back a number of those Christmas cards. And so why I tell you that story is because, I think, even though they're small tones, there is an identity that you have with the community, and a connection that you have with the community that I think is harder to build. When you look at neighborhoods across the country, larger neighborhoods, I am not someone who says ‘Oh, we're so much better in these small towns, because we know our neighbors.’ I've lived all across the United States. And every place that I've lived, I've known my neighbors on a first-name basis, invited them over for coffee, or maybe a few adult beverages. But I think you have a sense of responsibility in small communities to the community because there are so few of you. And it takes everybody to make sure that the school functions, that the church functions, that the VFW functions. No one gets a walk in terms of their participation. And so I think that's a big part of my history, which is this connectivity to community and responsibility to each other.

Adam: At what age did you decide to pursue a career in politics? And what were the most important lessons you learned from those early races?

Heidi: Well, you know, it's interesting because I was awake during the 1968 election. I was in the eighth grade. And I was waiting for the election returns to find out if Robert Kennedy carried the California election. So that might tell you something about an early interest in 1. The political process, but I think as I got older, I became much more interested in the environmental movement. I went to a law school that specializes in environmental law, Lewis and Clark [College]. I did my internship in Washington, DC, as a junior in college for the environmental study conference, which was the beginning of the emergence of the environmental movement. And so I really, in my mind, transitioned from this ‘horserace theory of politics: who's going to win and do you like the personality?’ to ‘why we need to be worried about politics and worried about who runs the country.’ And so I never envisioned myself as a politician. I envisioned myself as somebody who would work for a politician to effectuate public policies that I agreed with. And I always tell people, ‘funny thing happened on the way to that goal.’ And that was an election when I realized when Ronald Reagan got elected (very popular president, but not particularly a fan of the environmental movement), that things can change pretty rapidly based on who's in leadership. And so I then made a commitment to work back into electoral politics, partisan politics to try and elect people who wouldn't disappoint me on issues that I cared about and just getting into that world. And then having people encourage me, particularly Senator Kent Conrad who at the time was the Tax Commissioner and my boss, encourage me to think seriously about running for office. So it was never ‘I'm going to run for the United States Senate.’ In fact, I never thought that I would go to Washington, I was always interested in state politics, which seemed much more manageable, and where you would have a greater individual impact. And so my political career went from an interest in the horserace to being concerned about issues that I care about, to realizing that who we elect in this country has a pretty dramatic effect on solving the problems in a way that we see them going forward, whether it's climate, whether it is debt and deficit, whether it is income inequality, that who we elect in this country has a big role in solving those problems.

Adam: Given that your natural inclination and predisposition was to work for someone in elected office, was not to be the person running for office, not to be the person putting yourself out there, putting your name on the ballot, how did you get to a place where you are comfortable taking that risk, taking that chance? How did you push your comfort zone to ultimately make this happen?

Heidi: Well, I ran my first statewide race when I was 28. And how that happened is it was the first, as I call it, Year of the Woman. Geraldine Ferraro had been nominated to be the Vice Presidential candidate for Walter Mondale, and there was a movement all across, especially in Democratic politics, to get women out of the kitchen, baking the cookies and serving the potato salad to putting their name on the ballot. And so I, along with some friends, formed something called the Women's Political Caucus within the Democratic NPL, which is North Dakota's Democratic Party. And we went about recruiting women who were on school boards, on county commissions, in the legislature to run for office. And I got a consistent answer, which was ‘no.’ And the second answer was, ‘if you think it's such a good idea, you do it.’ And at that point, it was like, ‘Well, what do you risk? No one expects you to win.’ But you want to make the point that women can in fact, serve in that capacity. So along with a woman who was nominated for Lieutenant Governor, and eventually became the first woman Lieutenant Governor, I ran on that ticket and came within just a few percentage points of unseating the 12-year incumbent State Auditor. And so what does that have to do with my political trajectory? And maybe what it has to do with mentoring is, yes, I didn't win my first race, but it positioned me to basically be appointed to a political position that really launched my political career. And that was State Tax Commissioner. So because I ran that race, I had not only the qualifications to be a State Tax Commissioner, having been their general counsel, but I also had the political chops as people saw it to get that appointment. And that really launched my political career.

Adam: And there's a really interesting theme in there, which is a theme that is explored pretty regularly on this podcast. The way that you're explaining it, winning by losing, which we see a lot in politics. The way that I tried to frame it is: failure is often a gateway to success. We need to rethink the way that we define failure all too often. We look at failure as something that is a terrible thing. We failed. That's awful. But if we rethink, reexamine, look at failure differently, it could be a game changer in terms of the trajectory of our careers, the trajectory of our lives.

Heidi: Yeah, I don't think there's any doubt about it. I think the greatest mistake that people make is not taking risk. Because they're afraid of failure. They're afraid of being judged for that failure. And if people tell me that, frequently, when I interview for various positions, I'll ask people what their greatest failure was. And if they say, ‘Well, you know, I've really been lucky.’ I'm like, no one's that lucky. If you've challenged yourself, you've had failure, and what did you learn from it? And how did that move you to the next step?

Adam: What I love about your question ‘What is your greatest failure?’ is thati t identifies two things. Number one is it identifies how willing someone is to put themselves out there. To your point, if you're unwilling to put yourself out there, if you're unwilling to take a chance, as a mentor of mine, a great politician in his own right, the former mayor of Los Angeles, may he rest in peace, Richard Riordan used to say, ‘only a mediocre person never makes a mistake.’ If you're too afraid to try, you're never going to achieve anything of any kind of meaning. The other thing that it does is it illustrates whether or not you have self awareness. If you are unwilling or unable to acknowledge that you've made any kind of meaningful failure, that everything in your life has gone so well, what does that say about your ability to either look inward or to admit mistakes?

Heidi: I couldn't have said it better. To me, I'm always curious about that response. And I won't tell you who this was, but I interviewed a number of candidates for the United States Supreme Court, one candidate had a great answer to that question. And the other candidate just kind of went, ‘Oh, well, I think I've been really lucky.’ I'm like, you know, really? Then how do you have empathy? The other thing is that I think empathy in any kind of role that we have is critical. If you can't see failure in your own life, how do you have empathy for other people's challenges and other people's burdens, and yes, failures. A failure of character, a failure to achieve something that they've desperately wanted, these say a lot about your ability to manage people as well, in my opinion.

Adam: Through my interviews with hundreds of the most successful leaders in America, I put together a list of the key characteristics in my observation of the most successful leaders. And on that list: empathy. Self-awareness, as well. And I want to ask you, in your experience, what do you believe are the key characteristics of the best leaders? And what can anyone do to become a better leader?

Heidi: I think a key component is honesty. And maybe that's a way to say exactly what you're saying: honesty about your inability to control everything, and your inability to know everything. An insecure person is not a good leader. The people who have impressed me the most, I've worked with lawyers all over the country. I, you know, as a former AG, I did a lot of really high-profile litigation, high-profile negotiations, like the tobacco settlement. And I have watched lawyers who want to dominate a conversation. And then I've watched lawyers who listen to what everybody has to contribute, and respond respectfully and go, ‘that might be an interesting way to advance our argument.’ And I've always been impressed, because the lawyers that I most respect, who I think are the best lawyers, are the lawyers who fit in that other category, who have the self-awareness and curiosity about a broader spectrum of ideas to be respectfully listening. And so I think that's a key component. I think the other key component of a good leader, and this is probably one that didn't make your list, is how do you make things fun. How do you make people feel like they're part of a workplace that, number one, people appreciate them, but also that they literally know that they're going to go to work and have fun that day. And I think one of the things that we're forgetting about the Gen Z is their workplace. They aren’t just grinding it out for a paycheck. That's part of their work-life awareness. And I think we don't emphasize having fun nearly enough. I think about that every day, like, do people feel appreciated? Do they know that I know their name? Do they know that I'm going to give them a little hard time and we're going to have a good laugh before we start? Are we able to make the place a pleasant enough place and still get the job done? And so having fun and people who can encourage and foster a fun environment, I think, will long term be much more successful with the next generation of workers.

Adam: And that's such an interesting observation because, from the outside looking in, we may think of many things when we think of Congress when we think of the Senate. The first word that comes to mind isn't necessarily fun.

Heidi: But I think honestly, probably if you said, ‘why have I been successful?’ I'm not often the smartest person in the room. And certainly not the best-looking or the most charming person in the room. But I like to have fun. And I like to listen to what people say and give them a hard time. And if you said, ‘why have you been successful in a lot of efforts?’ I can go down a line of national things that I've done, and I think it's because, at the end of the day, people like me, and I think they like me because I like having fun. And I like appreciating people for who they are and what they bring to the table. And if all you do is a dour seriousness every day, you're going to lose this next generation of workers and not be nearly as successful. So that personality trait is hugely valuable: likeability and fun-ability (I have that just made that word up. I don't know if that's a word.) But the ability to make people laugh and to have fun in whatever you're doing, regardless of how serious it is, is a gift and underappreciated, I think, in books about leadership.

Adam: I love it. Be you.

Heidi: Yeah. 

Adam: That's really what this comes down to.

Heidi: If you're a big old crab stop being a big old crab.

Adam: So the takeaway is, for most of us who have something within us that is likable, be you. For those listening who don't have that, man, I don't know what to tell you. But for the rest of us, be you. Yeah, you ticked off so many of the key characteristics, you ticked off so many things that are essential to effective leadership: self-awareness, self-confidence. Something you said, which I love, an insecure person isn't going to be a good leader. Curiosity, taking an interest in others, listening, asking questions, making people feel appreciated. And don't be afraid to live, don't be afraid to have fun. At the end of the day, we only have one life. Let's enjoy it. That’s what it's all about. Let's enjoy it. And let's help those around us enjoy it.

Heidi: So think about this, there's such a conversation right now about people not wanting to come back to work. I would say that every person who's trying to get people back to work should examine whether they have enough fun in the workplace. And I'm not saying you know, you get a bouncy ball or you do the gimmicky thing. I think you create an atmosphere where people can be authentically themselves and can be appreciated for who they are. So to me, that's something that it's hard to measure. But it is a critical part of getting people back into a workplace where collaboration is once again advanced.

Adam: So from the outside looking in, there's this perception that the United States Senate is a highly polarized environment. People are on one side or another side. Deeply divisive. You spent six years in that environment. To what extent is that true? And how were you able to get things done and collaborate with people who you may have had nothing in common with, who may have seen the world completely different than you, who you may have not even liked at all as a person, you may have not respected but who you needed to work with? How did you get that done? And what advice do you have for anyone listening who finds themselves in a similar situation? Maybe they're not United States Senators, but so many of us find ourselves in environments where we might not necessarily love the person who we have to deal with, but we have to deal with them. I was recently giving a keynote and someone in the audience asked me, as a leader, how do you work with other leaders who you don't like and who are difficult to deal with? And I want to put that question back to you.

Heidi: Well, I think the first thing is there's an old management rule that 80% of your trouble comes from 20% of the work or the people, right? So number one, there is a collaborative, congenial, respectful attitude among 80% of the people who serve in Congress. Unfortunately, the media amplifies the other 20%, amplified because conflict apparently sells newspapers and people getting together and having a good laugh or going into the other cloakroom or pulling jokes on each other, that doesn't get a lot of attention in the media. But that happens every day. This is a group of 100 people in the United States Senate who are, for the most part, incredibly smart, capable leaders. They've had long careers either in business or in government, or in the military. And they respect each other just out of the sense that we all got there the same way by convincing people to vote for us. And so I think when you start with the sense that, on two sides, number one, there may be leaders that you're never going to get along with, particularly those people you can't trust. The people that will say one thing to you, and then another thing to another person. So I'm saying, pick your fights and pick your collaborators. So I'm not going to pretend that you're going to get along with everybody who is there. I got along with probably a huge percentage of people on both sides of the aisle and made friends with people who I didn't have much in common with politically or even socially, but yet we could see common purpose. And so when I talk about the work that I did in the United States Senate and the success that I had, it was built on compromise. It was built on understanding, ‘what is your concern? And even though I don't agree with you, how can you and I collaborate to do the thing that we both can agree on?’ Here's a great example: I was working on a bill that I saw as a climate bill. It’s called 45Q, it's a tax credit for carbon capture, sequestration and utilization. And that was my lead on this bill. And I had Mitch McConnell and Sheldon Whitehouse on the same bill. How did I do that? I did that because Mitch saw the advantage of that bill, in terms of a future for the fossil industry in a climate-constrained or carbon-constrained world. And Sheldon saw that as an essential element to fixing and moving forward in a way that would achieve climate goals. And so you've got to find those policies that speak to a spectrum of interests that achieve the same purpose. And I'm not saying you could do that on everything. But I could give you an example of Roy Blunt and Debbie Stabenow for years working on mental health issues. And would they agree on everything? No. I mean, one of Paul Ryan's fondest memories in the Senate was working with Patty Murray, from the state of Washington, on so many kinds of social entrepreneurial things. And these are things that the public never gets access to because they're too busy doing the horse race to busy doing the ‘who's saying something mean about somebody in the hallway’ stuff, the gossip, social media stuff, and not really focused on letting the public know that there is enormous amounts of collaboration. One of the things that I did do that I thought was really valuable was I attended when I called the prayer breakfast. And you might think, well, that's heavily Bible studies. But the Senate prayer breakfast is really a story where every person who speaks, tells the story of their faith journey, and it usually is so informative in terms of not the bio piece, but really what was happening in that person's life, or what happened in their history, that made them who they are today. And I learned so much about my colleagues and learned to respect my colleagues so much by going there and listening to their stories, their faith stories. There's places where you can go to learn about each other, that take you outside of that, but help you understand motivation. And I had kind of a rule that I never criticized or believed that I could tell someone's motivation. I could be critical of their ideas, but not what motivated them to advance those ideas, because that becomes very personal.

Adam: I love that. And your answer is similar to what I told the person in the audience who asked me that question, which is (I love what you shared about the prayer breakfast) find the humanity in the person who you might not necessarily like, who you might not necessarily think you have anything in common with. Find the commonality. Find what you do like in them. Separate what you don't like. Separate what you don't have in common with them from what you do share with them, and focus on what it is that you do have in common. And see what you can do together to get things done.

Heidi: Yeah, I want to add something because it goes back to what people always say. ‘Well, how do you convince them? I said, ‘Look, there is a point at which you say, you quit trying to convince people, you quit trying to work with people.’ And I have a friend, Annie Duke. She's a poker player. And we work together on an initiative, a pro-democracy initiative. And she just wrote a book called Quit. And I think that's an important part for your listeners to understand. There is a point at which there is a law of diminishing returns. You're spending a lot of time trying to solve a problem that may not be solvable, or spending time trying to persuade somebody who will never be persuadable. And so you also have to learn when to quit, when to cut your losses and say, ‘I can't do this anymore, maybe somebody else can be successful, I'm going to turn my attention to something else.’

Adam: When to hold them, when to fold them.

Heidi: She said the difference between a professional poker player and an amateur poker player is amateur poker players will stay in hands way too long. They don't know when to quit. We are a culture that reveres tenacity. Well, I think tenacity has its place but at some point, you will spend a lot of your life trying to make something work that will never work.

Adam: Something you shared, which stood out to me is you said, ‘Well, 80% of my colleagues were people who, whether I agreed with them or disagreed with them, were people who acted in good faith and 20% (again, those were numbers, I'm not going to hold you to them), but 20% were people who you just couldn't trust.’ And my question to you is, how do you deal with people who you can't trust? It would be nice to live in a world where we could just say, all right, I'm not going to deal with people who I don't want to deal with. But how do you deal with bad actors? How do you deal with people who you have to deal with but who you fundamentally don't trust? What do you do?

Heidi: I think you marginalize them. You build your coalition. It's like any other kind of conflict resolution. Here's a great example. When I negotiated the tobacco settlement, we needed 100% AG buy-in. We had an Attorney General, I won't tell you what state, who just was so opposed to the whole process of litigating the culpability of the tobacco industry in youth smoking, and he wasn't going to sign on. And he wasn't going to do this. And eventually, I just said, ‘Don't. Don't sign on. Walk away from whatever Chair of your State, the money, and I'm just not going to argue with you about this anymore.’ I knew when to quit them. Well, eventually he signed on. He had a list of demands that if we open that up, there was no way we could have gotten our settlement done. And so you marginalize them, you cut them out of the action, and that doesn't feel so good. You don't let them dominate the conversation. And so you find your allies, and you hold fast. And eventually, it's amazing. A lot of those people will come around because they want to be part of a resolution of whatever you're working on. But they also want to dominate the conversation. And eventually, as Annie says, you have to quit them. And if they want to come back, that's fine. But this probably isn't scientific and doesn't have any management lingo to go with it. But I just know when to quit people. The fastest way you quit people is when they become untrustworthy.

Adam: Yeah, that's great advice. During your time in the Senate, you were regularly a swing vote, and you were almost always a very highly coveted vote. Looking back, what were the most difficult decisions that you faced? And what are your best tips on the topic of decision-making?

Heidi: Going back to mistakes, one that I've acknowledged pretty openly was during the whole, I think, challenge for Al Franken. The kind of schoolyard piling-on that happened to Al that I was part of, and I knew at the time and I've told Al this, I knew at the time what I was doing was wrong. And so what I would say is, there isn't anything worth not following your gut and your values. Don't make those mistakes. And when you do make those mistakes, because you will, acknowledge them. Acknowledge that you've made a mistake. A lot gets written about gun votes, but the gun vote that I knew was wrong was the reciprocity for concealed carry. That's one. And people will say, ‘Well, do you regret that?’ I regret that vote. It didn't, in the end, it didn't pass. But it was a wrong vote. And it was done knowing that it was something that I shouldn't have voted that way. You're going to make compromises on things that have less effect, but also will, for lack of a better word, lower your character threshold. And so don't take votes that lower your character threshold. Be true to yourself. The job is, I mean, the vote that people talk about the most is probably the Kavanaugh vote. People always say, ‘Was that hard knowing how difficult it was going to be to get reelected in North Dakota.’ I said, ‘I didn't hesitate for a minute.’ Once I made my judgment about his character, once I made my judgment about his ability to hold the highest judicial position in the land, it wasn't hard. And so frequently, the most principled ones are not the hard ones. It's the ones that you have to kind of go back and forth on that make it tough, but at the end, you have to be authentic to who you are. And I will tell you this, no job in the world is worth doing something that you know is wrong.

Adam: What can anyone listening to this conversation do to become more successful, personally and professionally?

Heidi: That's a tough question because I spend a lot of time with students, I spend a lot of time with staff over the years. And the one bit of advice that I always tell them is don't get stuck. And so if people want to be successful, don't get stuck. And by that, I mean, just wake up 20 years later and say why didn't I take a chance? Why didn't I do something different? Why didn't I jump into this issue or take that chance? And so to me, the most important thing is to think about is what you want people when you are at the end of your life to say about yourself, and then work to make sure that you've earned that obituary.

Adam: Senator Heitkamp, thank you for all the great advice. And thank you for being part of Thirty Minute Mentors.

Heidi: Well, thank you for having me. I don't know if it's been a value-add to your listeners, but it is an opportunity that we all have to be a positive influence in other people's lives. But never forget, when you have a chance to, share some fun with everybody in your life. That's a pretty critical component that gets ignored.

Adam: I can say with full certainty this has been a tremendous value-add to listeners and been a tremendous value-add to me. Thank you again, really appreciate it. 

Heidi: You bet. Thanks Adam.


Adam Mendler is an entrepreneur, writer, speaker, educator, and nationally-recognized authority on leadership. Adam is the creator and host of the business and leadership podcast Thirty Minute Mentors, where he goes one on one with America's most successful people - Fortune 500 CEOs, founders of household name companies, Hall of Fame and Olympic gold medal-winning athletes, political and military leaders - for intimate half-hour conversations each week. A top leadership speaker, Adam draws upon his insights building and leading businesses and interviewing hundreds of America's top leaders as a top keynote speaker to businesses, universities, and non-profit organizations. Adam has written extensively on leadership and related topics, having authored over 70 articles published in major media outlets including Forbes, Inc. and HuffPost, and has conducted more than 500 one on one interviews with America’s top leaders through his collective media projects. Adam teaches graduate-level courses on leadership at UCLA and is an advisor to numerous companies and leaders. A Los Angeles native, Adam is a lifelong Angels fan and an avid backgammon player.

Follow Adam on Instagram and Twitter at @adammendler and on LinkedIn and listen and subscribe to Thirty Minute Mentors on your favorite podcasting app.