Leadership Conversations: An Interview With Les Stein

This interview was conducted by Ben Liff, Manager of Leadership Development at Smith & Wilkinson.

Welcome to the first of what we hope will be many fascinating and insightful Leadership Conversations. My name is Ben Liff and I’m the Manager of Leadership Development at Smith and Wilkinson. Each week, I’ll be chatting with leaders in a variety of fields as well as experts in the world of leadership development trying to tease out what makes great leadership, because as we all know, defining such a concept is almost impossible…we simply know it when we see it.

Creating and managing a Leadership Development program is more aligned with education and program management than what most people probably think of when it comes to “Leadership.” That’s the world I come from: education, or academia, and It’s the world I’m most comfortable in. It’s also where I met Les Stein a few years ago, as we collaborated at Northeastern University’s Roux Institute in Portland, Maine to develop leadership seminars for corporate partners.

Dr. Les Stein is a retired United States Marine Corps colonel, where he served 27 years. As a Marine officer, he filled numerous leadership roles, commanding the Marine Corps Logistics Schools at Camp Lejeune, North Carolina. His emphasis on training and education extended beyond his time in the Marine Corps as he continued to demonstrate (and foster) leadership through various roles in education. He served as the principal of a K-8 charter school in Raleigh, North Carolina, as the executive director of another K-8 charter school in Durham, North Carolina, and also works as a leadership consultant.

Currently, Dr. Stein teaches leadership classes for the Master of Science in Leadership program at Northeastern University’s College of Professional Studies. He’s published two books, The Value Frontier: An Introduction to Competitive Business Strategies and Education Disrupted: Strategies for Saving Our Failing Schools.

I’m extremely grateful to Les for taking the time to speak with me and hope that his valuable insights into the fundamentals of leadership resonate with you as much as they have with the countless students, soldiers, and others he’s worked with during his career.

Note: Interviews have been transcribed and edited for clarity and length. No substantive changes have been made to the interviewees’ original words or intent.

Ben Liff: Hi Les, thanks so much for taking the time to for this interview. To get started, can you share some information on how you work with leadership within your role at Northeastern?

Les Stein: One of the things that I try very hard to instill in our program, and that’s why I appreciate and enjoy training, is the idea that leadership is founded on some very specific foundational and baseline elements. It’s an interesting discussion because, in science, you have to have a foundation before you can build, create, and support your theories.

If you keep throwing out pop theories and pop issues, then it becomes an art form where everybody has an opinion, but there’s no common ground. What I want my students to walk away with is an understanding that I may not be able to give you a specific answer to a particular problem, but I can guide you through theories and models that will lead you in a direction to solve this problem.

Ben: One of the touchstones we’re working with at Smith and Wilkinson is the idea that leadership fundamentals are industry agnostic.

Les: The problem is that we see books on how to lead this or that kind of organization, but they’re all separate ideas, 10,000 of them, leading nowhere specific. How do you bring people together to identify the foundational, common elements for real leadership solutions? You can’t keep up with the disjointed approach; there has to be a core that you can use to consider various different problems and issues. That’s why in our [Northeastern University Leadership Program], we focus on the universal principles that can guide leadership across different situations, rather than getting caught up in the latest fad or individualistic concept.

I believe the science of leadership should offer you an opportunity to use one concept to potentially answer multiple leadership challenges. Too often we see a book on how to lead a specific type of organization and then we look at various concepts of leadership.

Ben: When was the first time you can remember considering yourself a leader?

Les: Consciously thinking of myself like, “I’m leading something here,” probably didn’t happen until boot camp. You’re given certain assignments, and everybody gets a chance to demonstrate that they can do certain things. Otherwise, you’re basically just a piece of dirt, and nobody cares much about you. But they’re trying to figure out, “Who can do this?”

That’s when I figured out that I can motivate people. I feel that in my lifetime, a long lifetime now, I’ve been successful at getting people to understand why I’m asking them to do certain things and get motivated about it.

And so that, for me, is a critical element to leadership. That’s why we talk about transformational leadership and the value of being a transformational leader. And that’s not the only kind of leadership there is, but those are the ones that probably can take an organization from good to great, as Jim Collins says in his book.

And so, that was my foundation. That’s why I learned, hey, I feel comfortable.

Ben: Who would you say gave you the best piece of leadership advice you’ve ever gotten, and what was it and how did it impact you?

Les: That’s one I think about often. I have been very fortunate to have some very good leaders. Again, I go back to the Marine Corps. I had some people who I just thought were the epitome of leadership.

Their leadership style was, “I am in a position where I can make decisions, but I am the same as you. I have the same values, same interests. But I’m in the position of leadership, and I will treat you generally as an equal, as long as you show me that you deserve that treatment, that respect. If you don’t, then I will push you to the side and say that you are not worthy of what I consider the greatest organization in the world, the Marine Corps, and then I will ask you to move on.”

So, the first person that I had an opportunity to follow was a lieutenant colonel when I was a second lieutenant in the leadership position. He was very unassuming. Other than the fact that he wore what we call the “silver oak,” he was like everybody else. The way he treated a lieutenant or a private or a captain or a major was no different across the board.

He would talk to them the same way. I also found that he did not hesitate to get his hands dirty. He wanted to show us that he could work with us, even though he had other responsibilities as a senior leadership position. But at the same time, he was no different. So the people that had the greatest impact on me in the Marine Corps were the ones that demonstrated that their leadership style was leading by example, being the same individual at home as they were at work. That was very important to me. They didn’t put on a show.

Ben: How do you ensure that you’re always learning and growing as a leader and as a person?

Les: First thing I do, Ben, honestly, is I continue to watch people. I continue to study them. I’m always curious to know why somebody made a decision or did something, especially if it’s something that I wasn’t expecting. You know, I want to know why. Now, sometimes I have an opportunity to ask them, and then I find out there’s a reason for it; other times I have to guess. Sometimes I don’t understand, and I still walk away, not really knowing. I’m very conscious of who I’m dealing with and very curious about what drives them.

Going back to the discussion we had about pop psychology, I love reading about leadership, but everybody has a great idea and a wonderful recommendation. They’re often very basic and common sense. Circumstances will create the environment in which I live and cause me to do the things that I do. Sometimes reading articles about people’s specific situations is more informative than a whole book that just repeats the obvious. So primarily, how do I learn? I learn by watching people and asking them why they do certain things.

For me, it’s studying and watching how that all unfolds. I’ve been very fortunate. And hiring the right people, putting the right people on the bus, that’s my most important function. If I can do that and follow up with emotional and social intelligence, good communication skills, and retain them, that’s my next level.

Ben: You’ve already touched on this a little bit, but what are some of the most common mistakes you see leaders make or, as a leader, have you made? What do you see leaders confidently doing wrong these days?

Les: I think the motivation that people have is often more personal than organizationally focused. I strongly believe that when you decide to work for an organization, you’re making a commitment to do the best you possibly can for that organization.

Very often, people come into leadership positions because something attracted them, like the position or the title. That’s the wrong reason for joining an organization, and it ultimately creates problems because they’re doing it for themselves. They might put on a show that sells them within the organization, but in fact, their motivation isn’t honest.

That to me is the biggest mistake a leader can make. The downfall of a leader is focusing on themselves more than on the organization, the people within it, and the organization itself.

And the other piece of this is when a leader doesn’t truly listen. They may pretend to listen, but they don’t care what you’re saying. It’s more than just the act of listening; it’s about being honest with people. I can forgive being a poor communicator, but when you communicate something false intentionally, that is something I cannot forgive. That, to me, is bad leadership.

Ben: Yeah, it’s all about hope and communication. You give false hope, that’s poor communication.

Les: It’s intentional communication of something false. That’s different from being a poor communicator. If your writing skills aren’t good, that’s one thing. But if you’re communicating something untrue or false, that’s unforgivable and a sign of bad leadership.

Ben: How do you teach yourself not to tell that little lie? The “I don’t want to hurt your feelings” lie? It’s not about trying to deceive someone, but maybe you don’t want to say “No” to an idea right away. But you should just rip the band-aid off and do it.

Les: People appreciate leaders most when they’re honest with them.

Ben: That doesn’t mean they like what they’re hearing.

Les: They may not like your answer, or even like you after that. But ultimately, they’ll appreciate that it’s better than being dragged along for months or even a year just to find out that nothing was ever going to be done. I’ve had that happen to me many times. Just tell me upfront if we don’t have the money or if you don’t like the idea. Whatever the reason, just be true.

One of the first things we like to do in an introductory leadership course is ask, “Who are you as a leader?” I always emphasize this during orientations. The first thing I want to know is who you are. The first step to being an intelligent leader is to know yourself, to understand yourself. If you’re convincing yourself that you’re somebody other than the person you see in the mirror, then we’ve got a big problem to begin with. How are you going to deal with other people when you don’t even believe what you’re saying to yourself? Understanding yourself is critical, and I think we have many leaders who really don’t know who they are, yet they’re leading other people.

Ben: Who is a leader you admire and why?

Les: One of the people I respected was Colin Powell. Although he passed away a couple of years ago, I think he made one big mistake in life, and he wrote about that and regretted it regarding the decision in Iraq. Beyond that, I watched him throughout my life and even got a chance to see him in action a couple of times.

The man was motivated by what is good for the country, what is good for our people, not what is good for himself. And that’s what we just talked about a few minutes ago. At the political level, I have a hard time seeing leaders who are very honest about what is the right thing to do.

Otherwise, I’ll be honest with you, Ben. I see a lot of people who are very technically proficient, very capable. But one example I will say is the university president at Northeastern, Joseph Aoun. I respect him. He is committed to a world that is focused on diversity and fair play. He makes it his lifelong passion to lead a university to demonstrate that they are global leaders, giving everyone the opportunity to demonstrate their great skills.

I think we find a few of them in academia because they are idealistic, but they’re idealistic in a way that they can make a difference. They are in a position to say, “Yes, we can hire the right faculty, the right administrators, and prioritize diversity, equity, inclusion, and belonging, even if it may not be popular among some politicians.” We do want minority students to have opportunities to learn. So again, people like Dr. Aoun and others are out there.

Ben: What do you think is the biggest challenge facing leaders today? By leaders, that could be anyone from the local bank president to community leaders. It doesn’t have to be professional, just in general. From top to bottom, what do you see as something that’s a struggle?

Les: I think probably the biggest challenge today that leaders face is dealing with people, convincing people that they can make a positive difference. A lot of people say that our society today is so much worse off than it was 100 years ago. That’s not true. The only difference is that we have social media that tells us how bad things are, while 150 years ago, you depended on a telegram that took time.

Ben: Ignorance is bliss.

Les: Ignorance is bliss. That’s exactly right. We’re doing good. Yeah, we’re doing very well, as a matter of fact. I like to use the example of, for instance, in politics, like the Adams-Jefferson campaign where they were running against each other.

Ben: Yes, I’m reading a Benjamin Franklin biography right now. He and John Adams hated each other. The stuff they had said about each other behind each other’s back was hilarious.

Les: And the difference, Ben, is that back then the best you could do is put a piece of paper on the local grocery store expressing your views or maybe publish it in a paper with a circulation of a few hundred. So today, I put it on Twitter, and about 3 billion people can hear about it immediately and believe it, even if it’s false, and that’s where we have the issues today.

I think that’s where the challenges are for leaders: dealing with the negative attitude that people often live with. Another challenge for leaders is effectively communicating their ideas in a way that would make sense to everyone to get the word out. My biggest challenge with my students, for instance, is convincing them that there’s a positive lining and that things won’t always turn out poorly. It’s very difficult.

But I think the biggest challenge leaders have today is to show that if we all work collectively, if we all work together, if we’re willing to compromise, we can move forward. Compromise is easier said than done because it means I have to lose something for the team to gain something.

The challenge is finding that balance where people feel they’re making a positive difference without losing too much. It’s about trust, communication, and a willingness to work together for the common good. That’s what leadership needs to strive for in today’s world.

Ben: That’s a huge thing that people, leaders are struggling with: how do you convince people that it’s worth it?

Les: And how do you convince them that your motivation is honest? One of the examples we use in one of my classes is I tell them I provide them with an example of a merger situation. I ask them what would you do in a situation like this?

A company has just bought out another company. The first thing that happens is the people in the company you bought out are worried about their jobs because what is your company going to do with the folks that you have just acquired? I ask them what are you going to do?

I ask my students what is your first line? What do you do to make them feel that they’re not expendable or they’re not going to be used as cannon fodder for the company’s bottom line? They come up with some very interesting thoughts but they all say, you know what, if I was in that position, I’d be worried. I’d be very worried because I don’t know what your motivation is.

So my point is, today as a leader, what is your responsibility? Your responsibility is to be honest with your people, communicate effectively, put yourself in their position, and be honest with them.

Ben: This has been brilliant. I really, really appreciate it. Thank you so much.

Les: Have a good one. Thank you, Ben.

Interviews have been transcribed and edited for clarity and length. No substantive changes have been made to the interviewees’ original words or intent.