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Art of Leading

Caryl Stern

Are You Comfortable Being A Leader And A Follower? You Have To Do Both.

May 3, 2023

Caryl Stern, executive director of the Walton Family Foundation, shares her key leadership insights with Adam Bryant in this “Art of Leading” interview.

Q. What is your playbook for leadership? 

A. It has evolved with each job, but my approach to leadership is very much about building a team of people with very different skills so that collectively we make up this really amazing brain.

To do that, it’s not just about what you bring to the table. There has to be ground rules of how we’re going to work together. You can’t just declare yourselves a team. You have to develop a team and develop the trust and creativity and space for there to be a real team. That takes a solid year of working very closely together.

Q. When you move into a new role, how do you decide who’s going to stay on the team?  

A. It’s important to set clear expectations. If you’re not contributing, you’re not going to succeed with me. It also means that I have to be able to give you real-time feedback. I hate annual evaluations. If I’m not happy with something, you’re going to know it. If I’m happy with something, you’re going to know it, and I expect the same in return.

Honestly is probably the most important thing I ask of all my employees, and that’s not comfortable for everybody. So if it’s not comfortable for you, allow me to help you find a place where you may feel better. I’m pretty clear about the work environment I’m going to create.

And so when I’m hiring, I want to understand their ability to be part of a team. What role did you play on teams in the past? Are you comfortable being a leader and a follower? Working for me, you’re going to be both. There are going to be times when we’re all going to follow you, and there are going to be times when somebody else is leading.

Q. You mentioned the importance of giving people direct feedback. What’s your approach for having difficult conversations? 

A. I want to first be really clear about why I want to give this person the feedback, so that I can then share that with them. It’s important to be able to look at someone and say, “I really wanted to talk to you because something happened that is troubling me or there was a particular behavior that made me uncomfortable or my expectations really were not met. And because I value you, I’m assuming all that was unintentional.”

If I can’t assume goodwill, then why am I investing in you?

I try hard to assume goodwill. And if I can’t assume goodwill, then why am I investing in you? So I try really hard to give the feedback in a way that focuses on what you did or didn’t do—not about you as a person. And then I give the “therefore.” There has to be a therefore, and it has to be clear, like saying that you never expect them to do what they did again.

Those guidelines help fill in the words for the specific script that I need for that person, and it gives me a comfort level. I’ve worked for people who were direct with me and I really appreciated the feedback over time. They made me better at my job. They let me know—usually, but not always—that they were invested in me.

Q. When you give people career advice, what do you typically tell them? 

A. One theme that comes up is entitlement. In my generation, when we started working, we understood we were at the bottom of the totem pole, and we didn’t have any great expectation to reach the top of the totem pole within our first two years out of college. We knew we had to pay our dues. So when a boss would give me an additional responsibility, I saw it as a privilege.

There was a definite pattern for a while of me having to sit with a group of employees and say, “This is the opportunity if you would like to take it. I want you to understand that, in my mind, this is a privilege for you. It’s your chance to show me what you can do, but it may feel like a burden to you. And if it feels like a burden, don’t say yes. I’m going to give you the out now.” Nobody ever took the out, but I at least let them know that was an option.

There were definitely a couple years when it seemed that everybody I hired thought that they should be the boss, that they knew better, and that they should be in every meeting. I’d look at them and say, “You can work here for a year before you tell me that you can do my job better than me.”

Q. Who were important influences early in your career?

A. I was lucky that I met people who invested in me. When I became a dean at Polytechnic University, I remember going to a dean’s meeting on Monday morning, and all the men were talking about football. I had never watched a football game in my life, but I started watching and learning.

At one point, one of the older women at the university—who wasn’t on the executive team—pulled me aside, and she said, “You do realize if they wanted to hire a guy, they would have not hired you. Stop trying to be what you’re not.” And I still see her face in front of me, and the words really stuck with me that the sooner I could get comfortable being who I am at work, the better off I was going to be. She helped me become a better leader.

I also volunteered quite a bit, and that teaches you a lot because most volunteer activities are very team-oriented, and you get to see some amazing people who are really generous with sharing their thoughts about leadership.

Q. What about earlier in your life?

A. My mom was a victim of the Holocaust. She came to this country at the age of six with her brother, who was four at the time. They came alone and they were raised in an orphanage on the Lower East Side of Manhattan. Hearing her story, hearing how her life was spared, hearing the selfless decisions that her parents made, taught me a lot about giving. Her mother and father ultimately survived the war, and it was about ten years before they were all reunited.

My mother believed in exercising your voice and being the one who stands up, and so she instilled that in us at a very early age. It’s why I have always been in the giving profession. I don’t think I had much of a choice in that.

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