Why Character Still Matters in Leadership

In this episode of Liberty + Leadership, Roger Ream sits down with Stock Executive Search CEO and TFAS alumnus Toby Stock to discuss leadership, civic culture and the habits that shape successful careers and institutions. Toby reflects on his work with prominent public intellectuals and organizations including the American Enterprise Institute, the National Constitution Center, Harvard Law School and The Dispatch, where he helped launch the media company alongside Jonah Goldberg and Steve Hayes. 

Together, they discuss the qualities that define effective leaders, the difference between management and leadership, the importance of courage and integrity in public life and why developing sound judgment matters more than ever for young professionals. The conversation also explores America 250, the current state of civic education, Congress and institutional incentives and the opportunities and risks presented by artificial intelligence. Toby also shares practical advice for students and young professionals seeking careers in Washington and beyond.

The Liberty + Leadership Podcast is hosted by TFAS president Roger Ream and produced by Podville Media. If you have a comment or question for the show, please email us at podcast@TFAS.org. To support TFAS and its mission, please visit TFAS.org/support.

Transcript

Welcome And Meet Toby Stock

SPEAKER_00 0:00

Welcome to the Liberty and Leadership Podcast, a conversation with TFAS alumni, faculty, and friends who are making an impact today. I'm your host, Roger Reim. The majority of my guests on the Liberty and Leadership Podcast are individuals who have participated in TFAS programs. They are TFAS alumni who've written books, obtained leadership positions, or excelled in some form or another as courageous and honorable leaders. And today is no exception. My guest is Toby Stock. Toby has accomplished much in his career, including at the National Constitution Center, the American Enterprise Institute, and now as CEO of Stock Executive Search, a recruiting firm focused on nonprofit and educational institutions. Toby was co-founder of Dispatch Media with journalists Jonah Goldberg and Steve Hayes. Toby's experience includes consulting, management, philanthropy, and even admissions at an Ivy League law school. He attended a TFAST program while a college student in the summer of 1998. Toby, thank you for joining me today.

SPEAKER_01 1:14

Thanks, Roger. Great to

Vision, Discipline, And Real Leadership

SPEAKER_01 1:15

be here.

SPEAKER_00 1:15

Well, maybe I'll start off talking a little bit about some of the people you've worked with in your career. You've had the opportunity to work with some great public intellectuals at the American Enterprise Institute and National Constitution Center, including their presidents, Arthur Brooks at AEI and Jeffrey Rosen at the Constitution Center. So I wanted to talk about leadership and what traits are required of a good leader, because I think that's a message that our students and alumni, as well as others, would like to hear.

SPEAKER_01 1:45

And I think, you know, in some ways, Jonah Goldberg and Steve Hayes and Elena Kagan, whom I work for at Harvard Law School, you know, all fit into that category. And they're all very different. And so there's not one prescription for it. But I think the common theme, I think, is the ability to have a vision and be able to articulate a vision and to bring people along with that. And to have a vision that is where they've really thought it through, where it's not just off the cuff, but you can tell they deeply think about things. Both Jeff Rosen and Arthur are early risers and like get a lot of work done and thinking done and reading done in the early hours of the morning. You know, Arthur famously, I think, gets up and is in the gym at like four or five a.m. And then he's, you know, writing and reading. And Jeff Rosen writes sonnets in the early hours of the morning. I mean, these guys are polymaths in a lot of ways. And I don't know if early rising is part of the deal, but certainly a number of the folks I've worked for have. But I do think to be a great leader, I think having great vision is important. And the folks I've worked with certainly have that.

SPEAKER_00 2:41

Do you think that a person is able to develop these things through discipline or hard work, or is a lot of it come just naturally and genetically?

SPEAKER_01 2:51

I think that certainly the folks I've worked with, there's clearly an internal driver that is moving them along, and that I think there's some of it you just can't train. But I also think the people that I've just talked about also are extremely disciplined in certain ways, not in every way, they're not perfect people, you know, all that, but I think they, in the terms of some of the things that people see publicly, you know, they are putting in the work. They're not just naturally good and gifted, they are, but they're also researching, working, thinking, writing, talking to people. And so I think you have to kind of combine those to reach that level. You don't just luck into it. You have to have some gifts, but it's hard to train some of that. But it's easier to train discipline, I think.

Management Versus Leadership Skills

SPEAKER_00 3:32

And would you agree there's a difference between management and leadership?

SPEAKER_01 3:36

Sometimes at the top of an organization, sometimes you need great management, sometimes you need great leadership, sometimes you need both. But I don't know if they're even naturally aligned anyway. I think often some people happen to have both of them, and some people, I mean most people probably aren't good at both. I mean, it's just not the same skill set, right? So I think it depends.

SPEAKER_00 3:53

In our

Courage, Values, And Telling The Truth

SPEAKER_00 3:54

last strategic plan at TFAS, we reviewed our mission statement and we made one seemingly minor change to it. We say our mission is to develop leaders, but we added the word courageous leaders, in part because we felt like in the environment we were working in five years ago, to be a leader on campus, certainly in our society today, you need to have courage too, because you never know when you might be canceled or when you have to speak up in an audience that doesn't agree with you and buck the establishment. I'm just curious of your thoughts about, you know, that we, in fact, we themed a conference recently, developing courageous citizens as an America 250 theme as well.

SPEAKER_01 4:30

I think it's great that TFAS is doing that. I think the challenge of the current era is that you can see so many examples of people who aren't necessarily courageous leaders and still make it. The bar has to be, you know, looking at yourself in the mirror every day. I think to me, it's important to be a courageous leader, to important to have values and standards, an ethical code that you you live by and work by. People succeed without that. So it's not about success, right? It's about how do you look at yourself? How does your family look at you? I think what kind of legacy do you want to leave? But at the end of the day, you know, there are plenty of people making it who don't bring courage, unfortunately, you know, in this day and age. But I look for it as I'm recruiting people because if I'm helping me to place someone in an organization, I'm thinking, does this person going to be an ethical person? Is it going to be a moral person? Are they going to tell the boss what they need to hear, not just what they want to hear?

SPEAKER_00 5:17

Yeah. In a speech recently at the Texas Law School, I know Clarence Thomas spoke about the need for courage in leadership, courage and accomplishing things, and kind of drew that contrast that I think you're touching on there, that you can be successful in Washington, sometimes more successful without exhibiting that courage and going along with the system. And but if you really want to be a principled leader, it sometimes takes courage.

America 250 And A Civic Reset

SPEAKER_00 5:41

Now you've you worked most recently before starting your current company, which we're going to talk about at the National Constitution Center. This is the semi-quincentennial America 2500.

SPEAKER_01 5:51

I'm glad you said that so I didn't have to.

SPEAKER_00 5:54

Or as the White House is calling it, which I kind of like, Freedom 250. You probably were involved in some preparations there leading up to it last few years ago. But what are your expectations for America 250? Do you think this is an opportunity for us to maybe bring the country more together than it is today?

SPEAKER_01 6:11

And look, I'm hopeful. I I think there have been a lot of great preparations at the Constitution Center. Most of my colleagues get that credit. I helped a tiny bit, you know, on the on the margins, but there are a lot of great people doing fantastic work, creating new projects there, uh new partnerships. I don't remember 76. I was zero years old as you know, I was a July 76th birthday. But my sense of that was that people didn't expect it to be as uh a hopeful experience as it was, and that people came out of that experience with a better sense of the history and uh of America's role in the world and about and uh coming together. And I think there are a lot of initiatives on civics around the country. Certainly, the Constitution Center is doing amazing things. And so I think America's 250th is a great encouragement to those folks to try more and think broadly, think bigger picture. There's a challenge in Washington, D.C., certainly, but I think, you know, at the end of the day, I think people want to have a bit of a more patriotic feel, to feel better about the country. And so, you know, that's going to be a force for good. And I think this summer, hopefully, we'll see an era of good feeling at least for a few months.

SPEAKER_00 7:15

We'll see. I remember 1976, the bicentennial. In fact, I spent that summer in Washington, D.C. in a TFAST program. And I moved a few months ago to a new house and I was cleaning out and I found a newspaper from July 4th, 1976, that I'd kept, Washington Post. And there was a story in there that basically the headline was something like, despite being very divided as a country, we're coming together for the Fourth of July celebration. So you're that's exactly reinforcing what you said.

SPEAKER_01 7:46

I read a great book about Watergate a year or so ago, and it is interesting the parallels, not trying to make a direct comparison to the current president. You can't really compare presents, they're all very different. But I think the kind of things that were happening, the pardon that I think now is looked back at the pardon of president Nixon, which I think now is looked back at as a patriotic act, a really wise act, you know, was incredibly controversial. So, you know, they're heading into that 76, you know, there was a lot going against the country. But I think, yeah, as you say, it was it was a moment of coming together. So we'll see.

SPEAKER_00 8:17

Did you get a chance when you're at the National Constitution Center to kind of get a sense of whether civic education in this country is in a poor state and needs an overhaul? Or where are we in terms of inculcating the next generation with, you know, important civic values and understanding of our constitution?

SPEAKER_01 8:34

Yeah. I mean, my colleagues will have to forgive me because I won't be able to cite the data that they intend to cite, but the numbers aren't great on just kind of knowledge of civics among middle school or high school kids. I think the the fundamentals are not great. I think there's a real challenge that folks just don't understand what's going on here in Washington, D.C. And I think, you know, there's a lot of reason to tune it out. And a lot of, you know, just like, why bother listening or reading? But I think, you know, you need people to get involved, you need people to get informed. And I think there are a lot of efforts at the center and other places. And I think the more initiatives to try to improve, again, young people's understanding of the constitution, of forms of government, it would be helpful to the polity.

SPEAKER_00 9:13

Well, shifting

Think Tanks And Fixing Congress Incentives

SPEAKER_00 9:14

a little to your work at AEI, one of the leading and probably most effective think tanks, policy organizations we have. I'm curious. I've been thinking about this quite a bit as to given the current state of our government and the fact that it seems like the Congress has just been unable to do much, to act, to be a strong third branch, and that so many things, decisions now are left to the Supreme Court or the executive runs the country. Do you think that diminishes what a think tank can do to be effective in this environment?

SPEAKER_01 9:49

It may validate the historic idea of a place like AI as opposed to other think tanks that got more in the moment. If they were more focused on changing policy today and being on the hill all the time. But I think the idea of a think tank as, well, let's look a little bit longer term. Today is not going to be the way it always is. So how do we look ahead and try to come up with ideas that will have lasting value? My sense, again, I'm an outside observer now, but there are a lot of friends, is that, you know, at least AAI, that they have a project related to the first branch of what they would call the first branch of government of Congress and the and and trying to come up with ways to change the incentives to get the people to do the jobs that they're supposed to do. I I think there are reasons why they're acting the way they are. And it's, I think the incentives are just designed that way. It's I'm not a scholar, but that's how I kind of read the situation is that uh members are doing what they're incentivized to do, and that's to become pundits in a lot of cases and not really do the do the work of legislating. And I think, you know, AEI, at least from what I can gather, is under Yuval Levin's leadership, is attempting to find ways to shake that up. But that's a longer-term project, right? I mean, that's not going to solve anything this month or this year or imparably the next four years, right? So I'm hopeful, but that's what AEI was all about. People said you should be more in the mix today on the hill, and they tried to do some of that. And that's famously why heritage was started, you know, 50 years ago, because AI was publishing papers that were too long-term. But maybe now's the time for the longer-term organization. I'm not totally sure.

SPEAKER_00 11:15

I was in a dinner conversation last night with a veteran of Washington politics, and he attributed most of the problems in Congress to the fact that they decided to term limit committee chairs. And he said when you had powerful committee chairs, they'd be a check on federal branch agencies, executive branch agencies, and even on the president. And that we got rid of these powerful committee chairs and they rotate now. And then I also think gerrymandering has kind of moved Congress to the extremes on both sides. And how about cameras?

SPEAKER_01 11:45

How about C-SPAN? I mean, I think Jonah would say that putting the cameras in there, you know, then everybody can do their video clips and then they're playing to the online audience now, right? So a lot of reasons.

SPEAKER_00 11:55

Yeah, I do think getting Congress to exercise its prerogatives is a key to restoring a balance in government. Let's

Why Toby Started Executive Search

SPEAKER_00 12:03

talk about your work now. You what led you to decide to start the company?

SPEAKER_01 12:07

You laid out my career at the beginning, which is really a series of, you know, taking very different jobs kind of over and over again, it seemed like, you know, it's a I like to joke, I can't hold a job. They went from, you know, consulting to starting an admissions consulting business to going to Harvard to run admissions at the law school to AEI for a decade to the dispatch, a media, what what business did I have at a media company to the Constitution Center? And I think the thread all along has been, and certainly when I was at Harvard Law School, I read I did 900 phone interviews a year. I mean, I was very engaged and kind of vetting candidates. And I think I always have had this habit of keeping in touch with people. And, you know, I think the most rewarding thing to me has always been building teams and matchmaking people, you know, someone would say, Hey, I need someone to run my foundation. Who should I talk to? And I'd give them three names. Hey, here's some good people. You might talk to these folks. And so I've always kind of been doing that as a for fun thing or side, yeah, side gig. And a friend of mine became a university president a few years ago and asked me to help out. And it was going to be on a bunch of things, but it turned out what he really needed was better talent, uh, finding new talent. So I ended up helping uh with a lot of searches and realized, gosh, this is what I've always enjoyed doing. I guess maybe I should do this for a living. I mean, that's the goal is to have a job where it's not work, it's just interesting and fun. Now, every you're never gonna have every aspect of to be perfectly fun, right? There's always parts of it that aren't. But I think I've always kind of tried to find paths in life where most of my days, most of my weeks, most of my years were just really interesting and fun. And I think I've been fortunate to have that a lot. But in this case, in particular, when I've always loved matchmaking people with organizations and leaders, to get paid to do that is great. I mean, it's a lot of fun.

SPEAKER_00 13:47

Are the searches you do exclusively for not for profits or are you doing both all types?

SPEAKER_01 13:53

It's almost entirely nonprofit and higher education of universities and then nonprofit organizations in DC or around the country.

SPEAKER_00 14:01

You've kind of

TFAS Influence And A Lasting Network

SPEAKER_00 14:02

answered the question I was gonna ask, but I'll preface it with a question about your experience at TFAS. That was 1998, I guess. And uh, could you speak a little bit to whether that had played some role in your career path and had some influence over your career?

SPEAKER_01 14:17

I'm still in touch with a number of the people that I was in class with at TFAS 28 years ago. In fact, on searches I've done, I've called to get advice from people that I was in TFAS with. And so even in my current role, it comes up, but it was really an immersion. And it was amazing the different people that you were able to get exposure to. Now, I remember my internship, one of the folks running it, because the guy happened to be downstairs in their building, set me up to spend an hour just chatting with Senator Paul Laxalt, former Senator Laxalt, who uh nobody knows of now, I suppose, but he was uh supposedly Reagan's good friend in the Senate and Nevada governor before that, and just a famous kind of DC figure of its era. And he just was a kind enough to spend an hour with this kid intern. And, you know, just you know, hearing about those years of the, you know, I'd grown up in the Reagan years and kind of hearing about that from someone who's an expert. That was one of many just serendipitous experiences that came out of TFAS and various threads of that would kind of wind into parts of my career later in life. Uh, the people I met and got to know and stayed in touch with, and and I think just the exposure to various aspects of government and policy and ideas, it was great. And it was between college and law school, actually, it was a great way to bridge that move for me.

Career Advice That Actually Holds Up

SPEAKER_00 15:31

If you were talking to students today or attending our program, kind of what advice would you give them if they want to embark on a career in in Washington, either in politics or journalism, or I mean, maybe you have to separate those, but just to be in the life of the nation here in their career. Uh there are things they should know when they're in college that you could offer.

SPEAKER_01 15:53

In college, you have this opportunity to just dig in on various topics that are of interest. Certainly you should, I mean, I know people study sometimes, but you should have plenty of time outside of class two to read and think. And, you know, certainly I would start reading the national media entities, certainly the dispatch. Uh, but you know, the Wall Street Journal, the you know, the New York Times, whatever it might be. I think it's uh Politico at the Atlantic. Those are the kinds of things that you should start doing in in college, in my opinion. I would say the interesting thing I've seen about more recent generation of young people is they haven't worked as much as I did, and probably you did, Roger. And so I think I would seek out those opportunities, certainly to work more during college if you're still there. And then as you get out, I would think look to be indispensable to your first bosses. And I don't know what that means. It's going to mean something different in every job, but how do you become the indispensable person, the person that everybody wants to throw more work on? You want to be the person that everybody throws more work on to. Uh, you want to be the person who's proactive, who asks for more things to do. I think you want to be the person who shows up early and stays late, even if it's not asked of you. I think you want to be the person who is focused on the details. This is a real problem for young folks right out of college and old folks too. It's like many of people who do the do work are just a little bit lackadaisical about details. And it doesn't matter at what level you are, you realize that details matter a lot. They can be a big deal. Get someone's name slightly off and they'll notice it. I see a lot of resumes. I see so many resumes. And one thing I mark on someone that's a big no is job hopper. This is a job hopper. And now I think you can do a little bit of that as a 20 something. That's, you know, but I would advise against it. And I think the sooner you get used to sticking around for at least until you get that promotion, like until until you get to the point where they're like, you know what, this person is meriting more responsibility. You should not leave, no matter how hard it is or how much you hate your boss, or whatever it is. I think too many people at all ages, but certainly in their 20s, jump around way too much. So that's my early first in the career advice that I would give.

SPEAKER_00 17:52

Well, there was a lot in what you said, and just that last piece is enough to say, would you speak to our students this summer? Give them career advice. Cause sure. It's something that's so common with uh I remember when I had worked one of my first jobs was I was at a place for seven years, and I went into this guy who was in his late 60s who was working there, and I told him I was considering another job. And he said, You've only been here seven years, you know, you don't want to be a job opera. And nowadays, you know, it's a year or two. I someone told me just this week that the average tenure of someone in fundraising is 21 months.

SPEAKER_01 18:27

Yeah. I mean, I so I I'm looking at a lot of applications resumes right now in fundraising, actually, and I'm looking for longevity because in development in particular, you can't build relationships in less than, you know, five years, frankly, right? If you if you're there less than five years, what did you really build? But you also kind of want to see growth in the career, right? So you want to see promotions, you want to see development. So if someone's there for 12 years, but they never changed positions, then you start to get a little nervous too. Kind of like late 20s, 30s. I think I would just add, at that point, I think thinking about developing judgment, like I think asking the leaders in your office, where did I exhibit good judgment, where did I exhibit bad judgment? I think it becomes more and more important the farther along in your career you get. I think also at those later stages, it's choosing bosses, not companies, choosing people to work for that you're going to learn from. I think that starts to become much more important as you kind of head a little bit down the path. So those are a couple, I just add those little additions as you get to the second and third, you know, role, maybe down the road.

Reading Well And A Mark Twain Pick

SPEAKER_00 19:27

Well, I'm one of those lucky people who gets your year-end missive holiday card or but you include with it, you know, a good accounting of your year and the books you've read and ones you recommend. Maybe you also include some of the better movies you've seen, I can't recall. But so I always turn to that for uh advice on good books to read. Sadly, talking about the young people in college today, reading seems to be somewhat of a dying art. I hope not. There's so much value in in reading, whether it's biographies or fiction or nonfiction. I think that's important to do. But do you have any good recommendations of any books you've read recently?

SPEAKER_01 20:04

The Mark Twain biography by Ron Chernow. Ron Chernow, famous for his Hamilton and his Washington and many others. Uh, you know, I'd kind of uh known a little bit about Mark Twain, but Chernow's uh massive work, I think, maybe a little long, but it's both a biography of a fascinating part of American history and the era. I think you learn a lot about the era as well, that he lived through the late 1800s and the changes that were happening in this country at the time, politically and socially and culturally. And so I I think it's uh, you know, it's it's a long one. You might want to listen to it double time on your podcast or on your audiobook or something because it's gonna take a while. But I think it was a worthy, worthy read. That's one of my recent recks. I was Well, I gotta ask you now. Did you read it or listen to it? I read that one in physical. That was a that was a gift of my wife, I think, for my birthday this past year. So I read it in in print. So I I I do more audiobooks these days because I'm always moving around and it's harder to harder to get to the physical books as much.

SPEAKER_00 20:59

So yeah, yeah. Well, I I appreciate that recommendation. I have not read that book yet, but I've read a lot of Twain and I love his writing. And I remember as a child going to Missouri to visit his home, and that was a wonderful experience.

AI Risks, Hope, And The Long View

SPEAKER_00 21:13

Well, let me ask you through all this experience, you've been in uh what philanthropy, consulting, think tanks, law school world. Are you optimistic about the future for our country?

SPEAKER_01 21:24

You know, one thing we haven't even talked about is AI, which I'm, of course, no expert on. I'm just a user like so many others. There's uh huge number of risks related to AI. You know, we've seen what social media probably has done to young people in this recent generation. And so there's a lot of risks there with AI. I do think a source of optimism is the possible advantages of AI. I think in healthcare and in science, you know, just changing the productivity equation of so many things. I think there's potential for that to be world changing in a positive way. Uh obviously, a lot of risks. There's a lot about what's been going on politically that makes me very concerned. But I do think that as Roger, you and I were talking, I think before this started, but there have been these moments in history that it's been pretty bad in America, the, you know, the 1850s, the 1870s you just described, the Great Depression, the late 60s and early 70s. And I think, you know, there's always these countervailing forces that bring us out. There's always mass movements of a positive kind that come up, whether it's a great awakening or or there could be a great civic awakening, perhaps. I think there are always these, I would call them counterantropic entities or enterprises that that happen when things get dark because people would prefer things to be better. And I think as long as we have kind of a free system, um, as long as there's freedom of speech and freedom of association, I mean, where would you rather be from a societal, cultural, political perspective? I think, you know, everywhere's got problems. This is still a good place to bet on, I think, you know.

SPEAKER_00 22:55

Yeah, the to the extent that people are building walls, they're being built to keep people from coming here and not leave here. Yeah. When you think about the sweep of American history, I mean, we're we are the longest lasting republic at 250 years. We made a lot of great improvements that I think our founders would be pleased to see, the abolition of the slave trade and slavery and extending the franchise and the tremendous medicine and so many other areas that have made life so much better for people. There's a lot of room there for optimism. So I I agree with what you just said. But it's still up to us and up to the next generation as to where this experiment in liberty will continue successfully.

SPEAKER_01 23:35

That's right.

Closing Thanks And How To Connect

SPEAKER_00 23:36

Yeah, well, it's it's been great chatting with you today, Toby. I appreciate you coming to the studio here, and we're proud to call you a TFAS alum. Thanks for all you've done so far in your career and look forward to working with you in the future.

SPEAKER_01 23:47

Well, thanks, Roger. And I I'm very appreciative of my TFAS experience. It's a great organization, and I hope many, many more folks get involved in as students, as donors. By the way, I'll put in a plug as a donor. I think it's important to support great organizations. So thank you for having me. I appreciate it.

SPEAKER_00 24:02

Well, and I'll take you up on having you speak to students this summer. All right, we'll do it. Willing. Thank you, Toby. Be buck. Thank you for listening to the Liberty and Leadership Podcast. If you have a comment or question, please drop us an email at podcast at tfas.org. And be sure to subscribe to the show on your favorite podcast app and leave a five star review. Liberty and Leadership is produced at Podville Media. I'm your host, Roger Reim, and until next time, show courage in things large and small.