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Tom Hollister, CFO of Harvard University, talks to the power of Never Again and the importance of open and authentic leadership to build teams. How to not make the same mistake twice, focus on forgiveness rather than punishment, achieve alignment of purpose, and how that funny word for the workplace–love—can help teams succeed.

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Harvard CFO Tom Hollister Speaks to the Power of Never Again

Podcast Transcript

Intro: Welcome to Beyond Leadership at the intersection of leadership and everything else. In this Cleveland Clinic podcast, we will commingle with extraordinary thinkers and explore the impact of their ideas and experiences on leadership and management.

Brian Bolwell, MD: Welcome to today's episode of Beyond Leadership. It's my true pleasure to be talking today with a very good friend of mine, Tom Hollister, who's the chief financial officer of Harvard University. Good morning, Tom, and welcome.

Tom Hollister: Brian, good morning.

Brian Bolwell, MD: So why don't you give our listeners kind of your personal journey, how you came to this leadership position after being in banking for most of your career?

Tom Hollister: Sure. I would say my career has been sort of a series of unexpected serendipity, and I've been lucky enough to be in different fields. I began, as you pointed out, Brian, in banking and did that for really, 25 years or so in a variety of roles and I enjoyed that enormously. Then I actually retired for a few years, not so much to retire, but as a chance to think about a new chapter life. Then total serendipity was joining Harvard a little over five years ago as the chief financial officer.

Brian Bolwell, MD: So one of the most common topics that we're asking everybody these days, Tom, is how has Harvard managed COVID?

Tom Hollister: Well, Harvard's pretty lucky. One interesting thing I've realized is that colleges and universities have different lines of businesses. We do not own our hospitals, our affiliated Harvard hospitals. Those big universities who do have been through a difficult period. Second, we don't have big time sports. That makes a big difference. We are also not too deeply tuition dependent. We have a variety of revenue sources, but what higher education is facing evermore is a sudden disruption in operations and from a financial standpoint, a sharp decline in revenues, which is painful.

Brian Bolwell, MD: So one of the things that you and I have talked about in the past about leadership is several things. One is the importance of developing trust. Can you give me some examples throughout your leadership journey of how you've seen that either in a good way or a bad way? What did you do as a new CFO five years ago to try to generate trust?

Tom Hollister: As you and I have talked about, Brian, I'd put trust right up at the top of the list of key leadership principles because if you don't have trust within your immediate team, you can't have truth telling and you can't generate the best ideas, at least in my experience. I don't have the best ideas. I can't figure it all. I need help and trust is essential. I think with immediate team members, it means they need to know that you're going to back them if you're in their court. If that's not the case, then it's a problem.

              In the case of Harvard, how did I build trust? I'd had the chance over the years to switch jobs. I always try to put relationship before task, get to know people. I literally, in the first several months, all I did is went around and said, "Hi, I'm the new CFO. Would you please give me some advice on what I ought to do? And please tell me how I can be helpful." Those became very provocative meetings and I listened and took notes carefully, and then tried to follow through on what people suggested in that. And of course, that's the basic stuff. Do what you say you're going to do. Help people out. It's favor trade. Be on the same team.

Brian Bolwell, MD: Yeah. I profoundly agree with that. It's hard to achieve much if you don't have trust. One way in which you do it, which again, I think you're probably extremely skilled at is to be authentic. Another thing that we've talked about, or actually, I'm going to steal a line from you, you once told me you're a PhD and making mistakes. I wish I'd thought of that line because I promise you, I've made a hell of a lot more mistakes than you have. But anyway, can you tell me more about that?

Tom Hollister: Well, I'd like to say I can challenge you on who made more mistakes, but take it to the extent I have any wisdom, I really do. I learned it through making mistakes and I like to call it the power of never again. If you make the same mistake once or twice, it's just so painful and you realize, "I don't want to do that again." So with younger colleagues I work with, I encourage them to take chances and make mistakes.

Brian Bolwell, MD: So do you share those mistakes with people?

Tom Hollister: I do.

Brian Bolwell, MD: What's the result?

Tom Hollister: More easily with distance and time because they hurt, they don't hurt as much and I'm, I don't know, more philosophical at this point in my career and trying to people know that I too, screwed up and I have an endless roster of screw ups.

Brian Bolwell, MD: So I personally find sharing that sort of stuff extremely useful and effective. It tends to make you more human. I think it tends be... kind of makes the environment a little more relaxed. People feel more free to share their ideas and I think ultimately, it creates some psychological safety when you're open about the mistakes or the missteps that we've made in the past.

Tom Hollister: Yeah, I agree. There's an element and mixture here of give and take with relationships knowing that we're fallible and forgiving each other and trying to focus on what did we learn and how are we going to get better next time as opposed to being punitive.

Brian Bolwell, MD: So do you consciously think about the concept of forgiveness?

Tom Hollister: Yes, all the time. I have one colleague who likes to say that he wants us to make mistakes, just not the same ones over again.

Brian Bolwell, MD: Yeah, I think forgiveness is another interesting topic. One of the, I believe this is attributed to Gandhi, who said, "It takes courage to forgive." I think that that's frequently true. Certainly, it's hard to see value in people who don't forgive and hold grudges. That seems to be a lot of wasted energy.

Tom Hollister: I agree. Also, we've talked about trust. One of the other key essentials is alignment of purpose or clarity of purpose. If you have people with different interests or different agendas, no enterprise is going to succeed with that. That's in the arena of politics or keeping grudges or departments not working, the kinds of things that we, as human, beings do all the time.

Brian Bolwell, MD: So how do you do that? How do you make sure that your team or your constituency has alignment of purpose?

Tom Hollister: I guess in the areas I can control it, which I guess means the people in the functions that report to me, I've come to demand... I tell them that is an expectation and anything to the contrary doesn't work here. If you're going to back stab your colleague or be off script... I don't think an organization can succeed. Now, there are different ways to manage. This is my own accumulated means of success, but I think it's really important.

Brian Bolwell, MD: How do you delegate?


Tom Hollister: I had to learn how to do it. I literally bought all the management books when I was a young person trying to figure it out. I watched other people who are better at it than I am. Delegation sure works if you have good people. If you don't, then it's a problem. I'm now to the point where it's kind of fun to hand somebody a challenging task and try to help them, but there are the basics, which is be clear on what the task is and what the timeframe, and tell people that you want interim updates and as to how to help and encourage them along the way, make sure they have the resources to do it or colleagues to help them. I think it's an acquired skill.

Brian Bolwell, MD: So one of the key parts of delegation that we've talked about previously is the importance of honest and straight feedback. That seems to have served you well historically. Talk about that.

Tom Hollister: I think two pivotal moments. One was the first time I had a management job. The outgoing manager told me, "Look, give people feedback. You'll be nervous. You'll do it poorly. You'll screw it up, but just do it and you'll keep getting better at it." That was really helpful. In fact, he was giving me permission to make mistakes and that that's expected and that's how you grow and get better. The other one was a moment, and Brian, I know you're a sports fan in some sports, but the name Bill Parcells, anyone who's interested in football would recognize him as the New York Giants and the Patriots coaches.

              I once read that he was asked by a reporter, "What do you tell the players who are on the edge of making the team or not making the team?" And he said, "I tell them the brutal truth. I tell them exactly where they stand, what they need to do to improve. I figure they're adults. They get handle that feedback. And if they don't, that's their problem, but it's unfair to give them anything else." And that, Brian, for me, was an “a-ha” moment. I suddenly realized that I'm not doing them well, I'm not doing my duty to help them develop if I can't tell them the truth.

Brian Bolwell, MD: Somebody once told me that when you're managing people, it's important to remember that nobody's perfect and there's good and bad in everybody. How do you decide the relative weights of those two things? And how do you try to coach people if they have challenges to try to get better?

Tom Hollister: We should circle back to the notion of, how do you get a good team with strong people? But I have come to the philosophy that it's my responsibility to help everybody succeed no matter how good or bad they are. Even if they're weak, I want to make sure they know what their responsibilities are and I want them to know that I'm going to help them all can to get them there, and I give them feedback. Here's a funny word to use in a business setting, but the word, "love." It's my job to try to love them and help them. If they trust that the reason I'm telling them this is to help them develop... Now, I don't just give them constructive criticism. I give them praise. In fact, I try to praise more. I try to create as publicly. Private encouragement is done privately.

              It's always thinking about balance of that. So it's encouraging, but I also try not to sugar coat it. Usually, what I find now most times is that if you help somebody try to succeed, and if it's just not a fit or they're not good at it, but they’re given every shot, they begin to figure it out on themselves and they'll go seek a place where they can succeed better, as opposed to what managers often do and I did when I was young is sort of count up all the years and finally tell somebody, "You're really not doing the job, so go leave." That's not fair or right.

Brian Bolwell, MD: Well, there's a couple of interesting things in that. So one is the concept of love, which is... I read something the other day from a leader who was asked, "How did you manage your employees earlier this year when the COVID pandemic was really starting to take hold?" And the answer was, "With love," and I think, frankly, that's true. That was true and I think what we did here, and certainly, what I tried to do with our employees in the Cancer Center, the other interesting thing about love is there's some literature that suggests that you can deliver love in very, very small chunks throughout the day by simply walking past somebody and smiling and saying, "Hello."

              In a brief 10-, 15-second interaction, maybe love isn't quite the right descriptor for it, but you can certainly elevate and create a nice little interaction between two individuals, even if you don't know the other person at all. I think that that's pretty potent stuff. I think that leaders actually have a power to do that. We sometimes don't realize that we have that power to elevate other people's day by simply acknowledging them and saying, "Hi." I think it's almost one of our responsibilities.

Tom Hollister: Yeah. It's interesting. I think as I observe great leaders or read about them, they create a bond, even in large organizations where each person knows that they're sound and that they give a damn and they care and they know their stuff, and they're trying to help everybody, and those little things become legendary and they multiply in way and stories are being told about how a leader expressed their interest and care or support for the cause or for the people involved. This is, as you say, powerful stuff.

Brian Bolwell, MD: So I'll go back to what you touched on, on the ability to create high functioning teams. How do you do it?

Tom Hollister: I've had the chance to have job changes. When I sort of inherit a new team, I make it clear that I want us to beat a team and to work together, and I need their help in learning what they're doing. I inevitably start with, what are we trying to achieve? So early on, I help... I don't help them. They help me, or we together, express... I try not to get too hung up on getting it perfect. Just basically, what are we trying to do? Help me know that. What do you need to get done and how do we all work together? So in the course of that, I try to get to know people. Then as I described, trying to help them succeed. I had an old colleague years ago, who said, "You should plow the field with the oxen you are given," meaning, just take the team you inherit and run with it.

              I think that's wrong. I think you do need to make sure you've got the best people that you can and get them in the right fit. There's no rush to that and there's no rush to judgment, but it needs to be continuous and some will rise and some will be better in a different job or a different field, but you have to get good people. I made that mistake too often, too early, where sooner or later, their failures become your failures and that's one of those never again lessons that I don't want to do again.

Brian Bolwell, MD: One of my favorite quotes is, "Great teams are a magnet for great talent." Once you have great teams established, then I think other quality people want to be part of that team. One of the keys to that, and it goes back to your comment about honest feedback, a lot of quotes about this. Colin Powell has a great one about, "Procrastinating hard conversations does nothing, but alienate the good members of the team," because ultimately, they're going to have to pay the price for carrying an extra load for team members who aren't doing what they're supposed to do. Yeah, it's hard to overstate the importance of teams.

Tom Hollister: I liked your point about good teams become magnets for more. I don't think I've ever achieved that. I've had high performing teams, but I never got to the point... There are people who do this, is that they're known for developing talent and people will join the organization or work in that group because they know that there's a record of people going on to success in other fields. It's almost a farm system or a feeder system or Ithaca improvement, but you also touched on the issue of festering problems and I did it a lot. And problem solving skills is really important to leaders.

Brian Bolwell, MD: So say more about that. How do you do that?

Tom Hollister: Well, I remember thinking to myself that kindergarten teachers try to teach kids problem solving skills. It seems kind of so simple. And yet for years, I would wake up at three in the morning totally distressed, overwhelmed with dozens of problems. Some things were eating at me. I didn't even know what they were, but what I've learned is that leaders usually, it comes down to just a few key matters in a few key decisions a year. The trick is to, with problems, accelerate into them. If there's any problems, as you said, Brian, or Colin, I think he mentioned it, you don't let it fester you, accelerate into it. One of the most powerful things in the world is to define the problem or label it. If you can identify the problem, then all of a sudden...

              Then if you have a trusting team, you can brainstorm how to fix it. It's magic because all of a sudden, you start thinking about that problem, defining and how might we fix, get a bunch of ideas and you put it up on the whiteboard. Then the next thing you know, the answer kind of pops out. Then there's the execution part, which isn't always easy, but usually if you can figure out the problem and you know what the right answer is, or you had a couple of answers, you can solve it. So now, I happily, I think I'm at a point in my career where I enjoy it. I like identifying the problems and trying to fix them.

Brian Bolwell, MD: Do you consciously try to create an environment of psychological safety for your team?

Tom Hollister: Yes. I think that's part of trust. I'm not sure it's an oasis, but it's a place where hopefully, people enjoy getting together because they can let their hair down a little bit and then what some issues are and hopefully, build friendships so people can bring challenges or problems and say, "Hey, here's what I'm dealing with. Do you have advice?”

Brian Bolwell, MD: What are the downsides of leadership for you?

Tom Hollister: I think the only downside is that it can be lonely. I think there are many more upsides because you can make a difference and you grow. We haven't talked about taking care of yourself. You can't be a good leader if you're under fire yourself or you're not feeling health and vitality, making room to think, having time to recover somehow in your life. Those things are essential.

Brian Bolwell, MD: How do you do that?

Tom Hollister: Imperfectly.

Brian Bolwell, MD: But at least you acknowledge it. You must make an attempt. So what're you doing?

Tom Hollister: I try to get enough sleep, try to eat well, try to exercise, try to certainly, turn devices off, read other stuff, go for walks, unwind.

Brian Bolwell, MD: So we always ask people, is there one moment of particular personal challenge that really stuck and pointed you in another direction or another path or another... At least the desire to change? Was there any one moment like that for you, or were there more of a series of never again moments, to use your words, that kind of got you to where you are today?

Tom Hollister: Well, I'll make a compare and contrast on that one. What I'm proud of in the course of my career is I took chances. I encourage people to take chances. In terms of sort of the crucible moments, it's usually when I have failed embarrassingly and it hurt and stung in some ways and still does, but I wouldn't trade it because I think it's made me better, more humble. In fact, one of my failing moments, I think in some ways, it was more successful, but the deck was stacked and I didn't understand it entirely. So I guess it is, Brian, getting back up on the horse. This is true, is you know of any great leader and you look at their record, it wasn't always easy.

Brian Bolwell, MD: No, and there's a wonderful book by Angela Duckworth called, "Grit: The Power of Passion and Perseverance," and she's done a lot of work studying what makes people successful. It's those two qualities. I think the perseverance part is a lot easier said than done. You get knocked down, everybody gets knocked down, but are you willing to get back on the horse? Are you willing to dust yourself off and get back in the arena and do it again and try to get better at it, obviously, try not to make the same mistakes that got you knocked down the first time? But inevitably, we all have setbacks and I think if we're self-reflective, they happen with a fair amount of frequency. Having the will and the stamina and the courage to keep going, try it again, I think these are qualities that are a lot more important to successful leadership than being brilliant.

Tom Hollister: It's interesting. One problem we all have is that we're inside ourselves. I had trouble because I would be emotionally involved in everything and I couldn't think clearly. Learning to be objective and give yourself advice or seek advice and forgive yourself that if you make a mistake and only say, "Next time..."

Brian Bolwell, MD: We're pretty big believers here in executive coaching. Do you have experienced with executive coaching? And if so, what are your thoughts?

Tom Hollister: I personally have not had an executive coach. I am delighted that the field has gone from behind the secret curtain out and they open it. In the old days, coaches were assigned to help people with known deficiencies. Now, they're known to help just improve performance. Actually, an executive coach is nothing other than being a learner and trying to, as I just said a minute ago, trying to be objective about yourself, which is hard to do. I have encouraged numbers of my colleagues to, or in a few cases, insisted that they get executive coaches. I think it's an investment in somebody's career. It's normal, of course, now. The big time private equity firms who bet billions of dollars on companies, when they bring in a new CEO, she or he, they're not going to let them take the job without an executive coach. There's too much riding on it. It's a best practice and I think it makes a lot of sense.

Brian Bolwell, MD: So do you have any other kind of global thoughts on leadership that we haven't touched on?

Tom Hollister: Some parts of leadership are transferrable just how do you deal with human beings? How do you organize things? How do you build trust? Look for good people, all those things. But if you fundamentally don't know the business, you're at a disadvantage because you don't have the instinctive knowledge of what needs to be done and you don't know it. A mistake I made too often earlier in my career is I didn't force myself to go down to not 10,000 feet, not 6,000 feet, not 400 feet, but down to zero and force myself to make sure I understood exactly whenever there was a problem or an essential issue. Was it intellectual laziness? Was it hesitance? Was it a feeling about not wanting to look funny? I don't know what, but what I guess it's the power of never again because I was burned by making bad decisions or choices because I really didn't know what I was talking about.

              So happily, at least I think by the time I got to Harvard, anytime in a meeting, and maybe this is just the comfort or confidence of being senior enough of willing to ask the dumb question, whenever I'm in a meeting or anywhere else, as long as it's not going to disrupt the meeting, I just think, what? What do you mean by that? I don't understand that. Would you explain that? Then if I don't understand, I go offline and say, "I've got to go study that." So knowing your stuff is...

Brian Bolwell, MD: I think that's pretty profound. I think that's very true, and I think that's a common mistake that's made in leadership.

Tom Hollister: You and I know that it's true in healthcare when physicians are suddenly made leaders, or in higher education where academics are suddenly made administrators and that in some ways, it's essential to be a physician to run a clinical operation to understand it, but leading the people and leading an enterprise is a different set of skills.

Brian Bolwell, MD: Very much so, and those can be taught, but unfortunately, too often, people are promoted into those leadership positions in healthcare because of their personal scientific success, which really bears no resemblance of a skill set of being an effective leader. This has been my pleasure. I hope our audience enjoyed our podcast with Tom Hollister who's one of the best, most authentic, certainly humble and effective leaders that you'll ever want to meet. We look forward to our next podcast with all of you. Thank you very much.

Conclusion: Thank you for joining us for this episode of Beyond Leadership. We welcome any topic ideas, comments, or questions about this, or any past episodes. Email us at or by clicking on the link in the show notes.


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Beyond Leadership

Host Dr. Brian Bolwell escorts you through a network of thought leaders, sharing world-class insight on leadership and cutting-edge hospital management approaches. They will inspire and perhaps compel you to reinvent your practices – and yourself.

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