Leadership is Constant Evolution: Steve Wells on Growing with Your Team

In 1920, Harold W. Wells, Sr. launched a fledgling insurance company in a small office on Princess Street in Wilmington, North Carolina. Today, his great-great grandsons Steve Wells and Harold “Hal” Wells serve as co-presidents of Wells Insurance, a family-owned independent agency that provides risk management and innovative insurance solutions in a team-oriented environment.

Steve says that while joining the family business was never mandatory, it was always an option—and one that offered him the opportunity to chart his own course. He started at Wells Insurance a few years after college. Today, as co-president and chief operating officer, Steve specializes in agency operations for Wells’s four offices, which together represent numerous national and regional carriers. The company also provides services worldwide through a partnership with Assurex Global.

An avid pilot and inshore fisherman, Steve sat down with DBH Consulting to share his leadership journey and reflect on lessons learned from more than two decades in the insurance arena. At the end of the day, he says, leadership is about constant evolution—the willingness to keep growing and learning while staying true to one’s core values.

Did you always expect to go into the insurance business?

Growing up, I knew it was an option. But our father told my brother and me that if we wanted to go into the family business, we had to do something else after college first, for at least two years. He wanted us to get jobs in the real world before we worked for him.

I worked at MetLife first as an automobile claims adjuster, and then I got a job as a personal banker. After that, I moved back to Wilmington. I didn't want to be subject to the whims of corporate decision making. I knew that if I went into the family business, I could basically chart my own destiny. It would be hard work, but the kind of hard work that can get you somewhere.

Were you on a leadership path at Wells Insurance from the beginning? How do you implement shared leadership in a family company?

A leadership track was implied, but it certainly wasn't guaranteed. Learning how to lead an agency, like any business, takes time and experience. For me, it took ten years of learning sales and sales processes along with operations. Your focus has to be on the agency, because if you take care of the agency, the agency will take care of the two things that make it successful: employees and clients.

Becoming a leader is a significant responsibility. Nothing taught me that faster than when, in my first year of working, I was called the “snot-nosed kid.” Today, as co-president, I have a duty to our 90 employees and their families. There are also reputational pressures that come with having a family business. You need to know when to be in the spotlight and when to step back and let others step in.

Hal and I discuss everything together and make all major decisions together. One piece of advice my father gave us was that during times when the two of us disagree, we should always yield to the one who has the stronger opinion. We try to do that consistently.

This past January, we also formed an executive team to help develop the strategic vision and decision making that will drive Wells Insurance into the future. There's five on this new executive team, and we meet monthly. The idea came out of my conversations with Demmie (Hicks) over the last year. It’s still early days, but already this team approach is helping us keep our eye on the target in new ways.

How do you hire?

I go with my gut. One of the main questions I ask candidates is “What do you do in your spare time?” I can usually make a hiring decision based on that one question.

By the time a candidate comes to me, my staff has already screened them to make sure they have the skills and qualifications needed, so I just want to make sure that they have a healthy work-family balance. I want to hear them say, “I love playing golf,” or “I love fishing.” Or any hobby—we’ve got a crew here that loves crafting, too!

I’m concerned about the people who say, “Well, golly, the only thing I ever do is work. I take it home and do it every weekend.” That outlook worries me. Don’t get me wrong; we work very hard here, but you can't work 24/7. You need to have an existence outside the office.

I want my employees to feel comfortable with the fact that they have lives outside of work.

What values have guided your leadership journey?

I like to help people. That’s a major value of mine. I enjoy success, but that's not what makes my clock tick. I get up in the morning because I want to help people. And if I can be successful doing that, that's where I find joy.

A related value for me is the importance of relationships. In this business, it's not so much what you know; it’s who you know. And trust is how you get there. I'm a very trusting person. When I talk to somebody, I immediately trust them. And unless you prove me otherwise, I will continue to do that. Trust and relationships have gotten me where I am today.

A third value is honesty. I'm a brutally honest person—I’m a “between the eyeballs” person. I don't like beating around the bush. And part of being honest is the willingness to push people to do their best work, to develop themselves, to rise to the occasion.

What advice do you have for emerging leaders?

First, you need somebody you can talk to. Somebody to bounce ideas off, someone who can encourage you as a leader. Throughout your career, you’re going to go through a lot of changes—sad times, happy times, angry times. And you can't afford to internalize all of that, because your hard drive will fill up too quickly. Having someone to talk to is key.

Second, learn to delegate. As you grow your business, trust your team to do their jobs. Be willing to pass some decision-making on to the people that you hired, so that you can actually run the business.

Third, strive to be the first-rate version of yourself. Don't say something or do something simply because you think somebody else is going to like you for it, because then they're going to hold you to that standard and it might not be authentically yours. Be yourself first. I’m much more of a back-office person than my brother is, for example. And it works because that’s who I am—I’m not trying to be someone I’m not.

There’s work that we senior leaders need to do on our end, too, to help emerging leaders. We need to give them the space to run and the runway to do it. We need to help them develop skills and give them the freedom to learn by doing.

What challenges does your company face in the near future?

We've got some producers nearing retirement age. At some point, they'll want to step away, and we’ll need to find other producers both on the servicing side and on the new business side. So that’s a concern of ours over the next three to five years.

Nowadays, most of our hires are young and hardworking but lack experience. It’s our job to support and encourage. Although some don’t work out, hopefully we’ve taught them valuable lessons that will help them grow their careers. We haven't had the recent opportunity, at least on the property liability side, to bring in a truly seasoned producer, which we need in order to handle the accounts of our senior producers.

Any final thoughts on leadership that you’d like to share?

Leadership means being consistent and having the flexibility to welcome constant evolution. You’re changing and growing all the time; the business is changing and growing, too. You can’t do it all alone. You need that person, that team, you can talk to and count on, so that you can celebrate or even cry with. You need somebody who can hold your feet to the fire—you need accountability.

I’m proud of the fact that we have a 97% retention rate with our clients. We’re honest with our clients; we tell them exactly what to expect. No one likes surprises. Leaders should prioritize regular and honest communication. You’d be amazed at the results of a genuinely trusting relationship.

Note: This interview was condensed and edited.

DBH Consulting guides emerging leaders aiming for the role of the CEO, with a deep commitment to relationship building and to racial and gender equity. DBH envisions a future where diversity and inclusion flourish in C-suites across the industry.

If you're inspired to take the next step in your leadership journey, get in touch with Demmie Hicks, leadership consultant and master coach at DBH Consulting.

This interview was written by Demmie Hicks and originally published by The Leadership Project and DBH Consulting. Used with permission.