I recently interviewed Governor Bill Weld on my podcast, Thirty Minute Mentors. Here is a transcript of our interview:

Adam: Our guest today is the former governor of Massachusetts. Bill Weld served as governor of Massachusetts from 1991 to 1997. He was elected twice as a Republican in one of the blue states in the country, winning reelection with more than 70% of the vote. Governor Weld, thank you for joining us.

Bill: It's my pleasure, Adam. Thank you.

Adam: Long before you are governor, you were a junior lawyer working on the House Judiciary Committee focused on pursuing the potential impeachment of Richard Nixon. What were the best lessons you learn from that experience and from that moment in time?

Bill: Well, I learned a lesson from how I got the job working on Watergate. And it really was the foundation for the rest of my career. But I was with second-year law students and someone came up to me in the library and said, “You look bored”. And like me, he was a moderate Republican, a so-called rip-on Republican. And I said, “What do you recommend?”. And he said, “Why don't you go into the state house and do some volunteer work for this very bright guy, who's a state representative. His name is Marty Linsky. He's going to run for lieutenant governor next year”. So I did. I went in and did some work for Marty and I had a big memo that I was due to deliver to him on a Saturday. So I went into the statehouse and went up to the fifth floor where there was no air conditioning. I took care of that when I became governor. It was hugely hot. It was June, everyone outside was having a party, hula hoops. And they were just having a wonderful time and I was up there on the fifth floor of the Statehouse slaving away and came down wearing my three-piece suit. And the girls cheered me and said, dirty old man, because of what I was wearing, I guess no other reason. I was 20 years old. So I took the subway back out to Harvard Square. And when I arrived, the station was in flames that had been set on fire by students. So I walked back to where I was living and thought, maybe I got this wrong. They were all having a good time. I was slaving up on the fifth floor of the statehouse, sweating through my suit. But it turned out that Marty Linsky liked the memo. He remembered me. And four years later, he got a call from a congressman named Tom Railsback in Illinois, who said, “Hey, Marty, we need some sane Republicans to staff this Watergate Committee, we can't have all crazies, you know, anybody who might be good”. And he recommended me. He called me up and said, “Do you want to do this bill?”. I said, “Marty, that's very nice of you. But I got to stay here. I'm a third-year lawyer. I got to stay here until I make a partner at seven years”. That's what we do. So he said, “Okay, maybe another time”. So I hung up the phone and the hair on the back of my neck began to curl. I realized I'd made a terrible mistake. Because of course, I wanted to do this sort of thing very much. It was like the ultimate piece of litigation. So I called Marty back, certain that he would have already awarded the plum to somebody else. But no, it was only one minute later. So I got the job and went down there. And I was the first person hired as staff. And the only other person who was hired at the same time was even younger than I was. She was a Yale Law student. So the two of us went in to see John Doar who was the lead counsel. And he said, “Bill, Hillary, I need a memo on what's grounds for impeachment of a president. Why don't you have it on my desk Tuesday, I don't want to ruin your weekend”. That's how it all started. I shared an office with Hillary Rodham, soon-to-be Hillary Clinton, and transferred from corporate to litigation. And that was the beginning of the rest of my career. And it's all because I did little things well, and somebody paid attention and noticed.

Adam: I love it. So many lessons there. The importance of following your instincts. You were on this great career trajectory, you could have gone the safe, traditional route, and become a partner at and prestigious law firm. But you knew in your heart, this was the right opportunity. And even when you turned it down, you weren't afraid to go back and say, I made a mistake. I regret the decision I made and reversed it. And it was a game changer in terms of the trajectory of your career.

Bill: No, there's no question about that. Everything jumped from there. And I learned something else from that experience, that it's good to go into the private sector when you're starting out. And I saw that a lot of the other workers there had gone from federal committee to federal committee. And they were almost scared of those of us who've been in the private sector, like we had to work hard with a lot of discipline and learn some stuff that maybe they'd never absorbed, just going from political job to political job. So when I'm counseling people now I say start out in the private sector, you can do the politics later.

Adam: Good advice. I want to ask you about your first run for office. The year was 1977, you're in your early 30s. And you decide you're going to run for Attorney General of Massachusetts. You run and you lose. But you don't just lose, you lose overwhelmingly to your opponent by more than 56 points. How did you navigate that early failure? And what advice do you have for anyone on how to manage the failures and setbacks that they face in their lives and in their careers?

Bill: Well, it's funny. That race was never close. And Frank Bollati was in his third term as attorney general. And he beat me at 20. I mean, he set a record for the widest margin in Massachusetts history, which endures to this day. So you never know which way things may go. So I called him up on election night and said, “Frank, he ran a great race. It was a privilege being in the race with you”. And what did he say? Oh, you little jerk, get lost? No. He said, “Bill, nobody remembers margins. Don't worry about it. Why don't you come in on Thursday? You, me, Tom Kiley, my first assistant, Peter, and Lucas, my Press Secretary will kick things around. Because the Republican Party in this state needs you. They're just a bunch of turkeys”. Turkeys is not exactly the word he used. So I went in on Thursday, two days after the election, and sat with him. And he just made me feel good about things. And Frank Bollati is still around. He's 99 years old. And he's a very classy guy. And there's a reason everybody loved him, is that he is just good to everybody, all the time. So I suppose that's another lesson I've learned from him, not from myself.

Adam: The importance of being gracious in victory, the importance of being gracious in defeat, the importance of just going forward, not getting down when you get knocked down, not getting down.

Bill: Gracious in victory is somewhat less common than grace in defeat. It's almost easy to be gracious in defeat but gracious in victory, I don't know, that's not always present. So it turned out for the best for both of us, because who knew? Two years later, Ronald Reagan gets elected as President of the United States. He needs somebody in Massachusetts to appoint as U.S. Attorney who knows how to try a case. And because I've been in the private sector trying cases, I knew how to try a case. So I got appointed U.S. Attorney, which is the top federal lawyer job in Massachusetts, and Frank Bollati is sitting there as the attorney general. So we're number one state, number one federal, and we have to work together for the next four years. And we did, very closely. So that really turned out to be a win-win all around.

Adam: It really speaks to the power of relationships.

Bill: That's also true. And I give Frank Bollati all the credit for that one call just set a lot of things in motion.

Adam: How can anyone build winning relationships?

Bill: Well, I think it's important. Not to ever call somebody out, have a bad news conversation and say, I think you did the wrong thing here and there. I just don't see any percentage in that. And if you do that, you're not going to have good relationships. But I remember saying to some of my staff, when I was governor, they'd say, hey, this guy's really handing it to us in the press. We should get back at him somehow. And I’d say, governors don't have bad news conversations. I don't have bad news conversations, okay? And they got it. So we didn't complain. The English have a saying, don't complain don't explain, something like that. But you got to be nice to everybody. And again, that's what Frank Bollati was doing, he was being nice to everybody including this little punk who he had just beaten at 20.

Adam: Yeah, you never know where those relationships are gonna take you.

Bill: Right. Now he became very important to my job and I became very important to his job because there had been an open war between state law enforcement and federal law enforcement at the time. In that, I came in, and my first assignment from the Attorney General of the United States was to repair the open rift between state and federal law enforcement. And that was pretty easy.

Adam: Yeah, yeah. You also brought up a really interesting point when you right off the bat said, don't criticize publicly. And I did an interview recently with Joe Maddon, the great baseball manager. And one of the things we spoke about, Joe said, “Praise publicly, criticized privately”. You will never see Joe Maddon or any great manager, any great coach, in any sport, criticize their players to the press.

Bill: Well, yeah, whenever there's going to be criticism delivered. And believe me, when I was being critical of somebody, they barely knew it. But there can never be more than two people in the room. And I've seen that rule violated in ways that would take your breath away. United States Senators standing up and just tearing apart a staff member in front of 15 other people in the room, please, you’re the United States Senator, you don't have to do that.

Adam: Yeah. And Joe Madden's point was, it really speaks to the insecurity of the person who's delivering the criticism. It says a lot more about them than about the person that they're criticizing. 

Bill: Ya know, my chief of staff used to make fun of me when there's someone who's better off someplace else. He said, “They never knew they were fired”. After I got done talking to them, they thought that they had just decided to do something else.

Adam: I love it. We spoke about an early setback, which turned out to be a blessing. What was the biggest challenge you faced in your career and how did you overcome it?

Bill: Well, I went from the Watergate Committee, came back, concentrated on litigation, and ran for attorney general because the Watergate experience had given me a view of corruption and how corrosive corruption can be to government and the quality of life in a country in general, and just the tone of public affairs that hasn't changed to this day. So I was appointed U.S. Attorney by Reagan and then brought down to Washington to be Head of the Criminal Division of the Justice Department. And I worked closely with the Public Integrity Section. And I had over 100 public corruption convictions during my five years as U.S. Attorney in Massachusetts. So that was my number one priority. And while I was in Washington, it seemed to me that the tone of the department was veering toward politics, as opposed to doing justice without fear or favor. That's very much in the news today. And what did I do about it? I resigned from the department along with five other people.

Adam: How did you decide to do that? How did you get to that place? And what did you learn from it?

Bill: Well, it seemed to me that the management of the department and the Attorney General was a very nice, wonderful person named Ed Meese, who had been an assistant to Governor Reagan in California. And he really didn't have the instincts of a prosecutor at all. And he had been in the White House as counselor to the president and came over as attorney general. And it seemed to me that decisions in the department were being made on the basis of politics as opposed to doing justice without fear or favor. And eventually, I said, “I can't stay here”. I'd be bearing silent witness to the administration of the department in a way that's not meeting justice without fear or favor. So the number two person in that department, a fellow named Arnold Burns, very much agreed with that. And the two of us in our top four all resigned on the same day, somewhat noisily I might add.

Adam: That really speaks to the importance of putting principle before career and valuing what you believe is right ahead of whatever might be most convenient. Clearly, standing up for what you believe is right has been a key pillar of your entire career. You prosecuted public corruption and brought over 100 convictions to the forefront. In your experience, how important is ethics to effective leadership, and why?

Bill: Oh, it's hugely important. If you're not grounded in ethics, you’re hollow. I don't know how you can be effective unless you have that as a guide in something you can always refer to and come back to it. You don't have to be pompous about it. You can even say this is how the game is played, or that's not how the game is played. But that message has got to come across like a steady drumbeat.

Adam: And so much of it comes down to building trust. If you're someone who doesn't have a moral compass, doesn't have a moral code, isn't a person who commands any level of trust, who's going to follow you? who's going to believe in you? who is going to want you as their leader?

Bill: Yeah, I would agree with that. I thought at the time that I might have thrown my career away when I resigned from the Justice Department. It didn't really work out that way. I was well-received in the private sector by law firms. And I decided to run for governor in 1990, which was just a couple of years later. And really didn't have the background for it. The only background I had was all those convictions in the Justice Department. And then in Massachusetts, unlike some other states, the fact that I'd resigned from the Justice Department was probably taken as a net plus, not a net minus. I remember being in some southern states shortly after that giving speeches. And people said, oh, son, you got fired. You pretended to resign, but you must have been fired. And that was the perspective of those in deep red states. So people see things differently. But up here that was not a negative. One other thing I would say is if you got something you want to do, just go straight ahead and damn the torpedoes. Though, when I ran, I guess it was the governor's race. So there was a primary and I had a pretty good opponent who beat me in the Republican Convention by a supermajority. So I was 35 points behind in the spring of 1990, which was the election year, 35 points behind my opponent in the primary. And the chairman state party, who was a rock-ribbed conservative and very much supporting my opponent, came to see me and said, “Bill, you got to get out of this race. You're going to disgrace yourself, you're going to bring contumely and disgrace on your wife and children, and you ruin your legal career. So do that as a favorite yourself”. So I said, “Ray, thank you very much”. And we left my back office there and I walked out arm and arm with him. And all my staff was ashen. They could see what that probably meant. I was gonna get right out. So I saw him out and came back and said, “Okay, we're going to double down. We're going to triple down here”. And we didn't have a lot to work with. All I could do was go to every single event all summer long, which I did. And I was the only candidate there because my opponent 35 points ahead was quite wisely pursuing a rose garden strategy, and not going to any events. But it turned out that for once the Rose Garden strategy was not a good strategy. Because everybody knew me from going to every single event. So I was able to win the primary.

Adam: How did you get to that place of being completely unafraid of failing and being completely unafraid of looking bad? How did you get out of your comfort zone? How can anyone eliminate the fear of failure and get out of their comfort zone?

Bill: If you're really gonna go for something, I remember Billie Jean King one time, that was a tennis player, she had a losing streak or something. And they said, how are you going to compete at Wimbledon? And she said, “I'm just gonna go for it. I'm gonna go for it”. That's sort of how I felt about that race. If the race is worth running, it's worth giving it your all. And I must say that, at that point, all I was thinking about was the primary because that's the only thing right in front of me. But waiting for me in the final, everyone's expectation would be Francis Xavier Bollati, the attorney general who had beaten me at 20, when I ran against him 12 years earlier. And what happened? My election was something of a fluke. Frank was upset in the Democratic primary by John Silber, the president of Boston University. So he wasn't there to beat me at 20 again, and then Mr. Silva, who I consider to have been a great man, frankly. And he got angry at two newspaper reporters who were interviewing him. Just in the last week of the campaign, he was 11 points ahead of me, with a week to go. And he blew up in these two interviews. One of them was actually quite funny. It was Halloween and a reporter named Natalie Jacobson, who was kind of the madonna of reporters and interviewers for Boston TV. She unexpectedly popped in at each of our houses. So she came to my house in Cambridge, it was dinnertime, and we were at the table. And she came in with her crew. And I was always happy to see the press. And she put the mic in front of me and said, “Mr. Weld, what's your greatest weakness?”. And I looked around at all that succulent food on the table, I do enjoy a good meal. And I looked her dead in the eye and said, “Mango chutney”. Which is true, I adore mango chutney. And she then went to Dr. Silver's house at Boston University, the president's house, and put the mic in front of him at the table. He had a big family just like mine, and said, “What is your biggest weakness?”. And he stood up, patted his mouth or napkin, threw it on the floor, and said, “You have no right to ask me that question in my own house” and walked down the hall and out of the room. And I don't need to tell you that the TV camera followed him lovingly every step of the way down that long hallway. And the votes just peeled off.

Adam: So many great lessons there. Stay the course. If you believe in something, go for it. Listen to your own inner voice. Trust your gut, trust your instincts. And finally, have a sense of humor. Self-deprecation is an incredibly powerful tool. Don't be afraid to use it.

Bill: Yeah, I agree with all those things.

Adam: What were the best leadership lessons you learned from your years as governor?

Bill: Well, apropos of humor being a good resolver of tensions. So I come in, in this sort of Yankee tradition, as governor, and at that point, most of the leadership in the legislature was of Irish extraction. And they didn't mind making fun of people who worshiped in wooden churches, their term, meaning Protestants. So every year, the president of the state senate, a man named William Bolger, a very learned man, triple Eagle, Boston college, high school, Boston College, Boston College Law School, and he and I both thought that nobody was ever harmed by a Jesuit education. He studied the classics and had a tremendous sense of humor and really oratorical skills. So he would hold this breakfast in South Boston for St. Patrick's Day every year. So I show up the first year and I look like dead meat, frankly. I walk in there with my coat and tie and at that point, probably a fairly stiff manner compared to the veterans of the Massachusetts legislature who are there. So he says, “Well, Mr. Weld, you deign to venture into our precincts here in gracing us with your presence. We're very privileged to have you among us, given that your folks all came over on the Mayflower”. And rather than go for the bait there, I said, “Well, Mr. President, that's just not the case”. And he said, “Oh, yes, I have it here”. And he holds up this book saying the Welds are a prominent family back in you know, the 16 whatever it is, and helped found Harvard College and got this and that. I say, “Well, that's exactly right. But we didn't come over on the Mayflower. We sent the servants over on the Mayflower to get the summer cottage ready against arrival the following summer”. I thought we're gonna lose three or four people in the front row. They died of apoplexy laughing so hard. But I never heard about that again.

Adam: I love it. Own it when there's something about you. Don't run away from it. Own it.

Bill: Ya know, that's known as owning.

Adam: Yeah. What do you believe are the key characteristics of a great leader and what can anyone do to become a better leader?

Bill: I think hard work. It sounds trite but trying to be perfectly prepared for a meeting, that's important. I had a law school professor who always said work is power. He moved to Washington, worked in the Department of Justice for a little while, and got a lot done. And I think he did it by outworking everybody. And I've already told you the story about how I outworked everybody when I had nothing else to do that summer when I was 35 points behind in the polls. But that's an example.

Adam: Yeah. Failing to prepare is preparing to fail. One of my favorite quotes from John Wooden.

Bill: Ah, okay. Well, you got a lot of good quotes there. You're extracting the aphorism.

Adam: I've interviewed hundreds of America's top leaders. I unfortunately never had the opportunity to interview John Wooden. But that is one of my favorite nuggets. And it's one that I live by.

Bill: Yeah, yeah, I think that's true. That goes right along with doing little things well, because doing little things well, is a facet of good preparation.

Adam: I cannot agree with you more. Over the course of your time as governor, over the course of your career, you worked with Democrats, you worked with Republicans to push through major legislation, and you worked on a number of high-profile deals. What are your best tips on the topics of negotiations and deal-making and courtroom work?

Bill: I always tried to persuade the judge that I wasn't really an advocate for one side or the other. I was just trying to help everybody see what are the just results here. It's something that a Fortis who is a supreme court judge, appointed by Lyndon Johnson, was famous for driving his adversaries crazy, by seeming to have no edge whatsoever. But he was just so skillful that the judge would wind up asking him, well, Mr. Fortis, what do you think we should do? That would drive the adversary nuts because it was like he and a fortress were together trying to find the right thing to do, they were searching for justice. So to the extent that you can enter either in negotiation, or even a piece of litigation, saying, let's try and get to the right result here, you're probably going to have a more successful negotiation than if you come in with your sword drawn.

Adam: And it really comes down to listening and being open-minded. Great leaders are great listeners.

Bill: Well, that's something that over time you do pick up in politics. In politics, you really have to be cognizant of and look out for the other person's point of view. And I've seen too many lawyers disregard that when they entered the room. They want to prove that they're the toughest guy in the room. And pretty soon everyone in the room, ah, you're not gonna get too far.

Adam: Yeah, the most successful leaders don't walk into a room intent on speaking, they walk into the room intent on listening, walk into a room intent on learning.

Bill: The greatest lawyer I've ever met was Edward Bennett Williams, who is a very famous trial lawyer, a product of Georgetown Law, and his firm was called Williams and Connolly in Washington, DC. But one time I was the head of narcotics prosecution in New England, and he had a couple of clients who ran the largest marijuana ring in the world. No rough stuff, nothing beyond marijuana, no guns, but astronomical amounts of marijuana. So they got arrested. And there was a new statute that had just been passed called the continuing criminal enterprise statute. 10 years of a mandatory minimum sentence if the enterprise is of such and such a scale, which they qualified for big time. So he comes in, and he doesn't say my guys aren't guilty. He says, “let's look at this. We have this new statute of perhaps doubtful constitutionality. It has not been tested yet. And there's a 10-year mandatory minimum. My kids are in their 30s”. This helps his clients guess who else was in their 30s. And years is a long time. And so he skirted all around, he never really joined the issue on any contentious point, because these guys had been caught in the act. And they'd been running this huge ring for a long time. So there were 50 people willing to say what they had done. He just showed the benefits of accepting a guilty plea to a 10-year sentence. And if he'd gone to the map, those guys probably would have gotten 30 years' sentences. But he did absolutely the best he could for his clients. And it was also the best for my side because the statute was applied and upheld and it was off to the races for the Justice Department and would not be politically correct in today's climate for darn sure. He was a lawyer to the situation. And that's what I was talking about earlier when I said if you can persuade the judge that you're searching for justice, hear your lawyer to the situation, those are some of the most successful lawyers, I know.

Adam: Another important lesson here is that not everything is a zero-sum game. What he worked toward was the best outcome. For him, what was the best outcome for his clients was a great outcome for you. You had the same goals and the same objectives. And that's how it worked out.

Bill: Yeah. And I felt good about the result. And he could feel very good about the result. As I say, he was the greatest lawyer I've ever met. His biography was called The Man to See: Edward Bennett Williams. If you're in Washington, D.C., and you're in deep yogurt, you want to go see Ed Williams.

Adam: It's a pretty good title. It's a pretty good nickname. You've worked for and with many of the most prominent political leaders over the last 40 years, including presidents from both parties. Who are the best leaders you've been around? And what did you learn from them?

Bill: I enjoyed the company of many, many of my fellow governors, Republicans and Democrats, a great job. And generally, people who get to be governor have been through the rough and tumble, so they're not puffed up in their own self-esteem. I cannot say the same about all United States senators I've ever met. But governors are, relatively speaking, a rowdy lot. And they didn't get the easy way. I remember, one fellow I particularly liked was the governor of Colorado when I was in office, his name is Roy Romer. And we were having a meeting in Colorado and that day was announced in the press that two of my cabinet members were getting married to each other. And that ordinarily wouldn't have been the occasion for much comment, except they were both men. And it was also announced that I was going to officiate their wedding. Robert, he says to me in front of the whole assembly of governors who said, “Bill, don't you understand that you have to be all one thing or all the other, you can't be right in the middle”. He's joking, of course. So I did. I officiated their wedding. And Roy Romer, who later became head of the Democratic National Committee under Bill Clinton, was a very good friend of mine. But his next job after he left being governor of Colorado was to go become superintendent of the Los Angeles school system. You talk about a tough job, about a no-wind job. Being head of the L.A. Unified School District would be right near the top of my list. He was a very successful two-term governor. So what'd he do? He goes and looks for the toughest job in the United States, one that can do a lot of good, and goes and does that. So he’s gonna be pretty near the top of my list.

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

Bill: Not having too high of a regard for yourself and working as hard as you can. You're gonna catch your share of breaks. It was just luck that got me elected governor. So I think trying not to have a big ego, which is very important if you want to be successful in the long run.

Adam: Governor Weld, thank you for all the great advice and thank you for being a part of Thirty Minute Mentors. 

Bill: Thank you, Adam. I enjoyed it very much.


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.

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