Lessons In Leadership: One On One With Delta Dental’s Dennis Wilson

I spoke to Dennis Wilson, CEO of Delta Dental of New Jersey and Connecticut, about his best advise

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Adam: What is something about you that would surprise people?

Dennis: Let me start by saying I’m excited to dig into these topics with you. I noticed that you’re an Angels fan and I’m a big baseball fan. Most people know that I am a diehard Boston Red Sox fan. What they don’t know is that I once was a Yankee fan.

Those that know me as an adult, especially in business, would be surprised by this story. When I was a kid, I played youth baseball. For the first half of the season, I literally just stood at the plate and never tried to swing. So, there’s only two outcomes: walk or strike out looking. Finally, my coach pulled me aside and said not to be afraid to swing. The worst thing that could happen was that I’d strike out and I was already doing that, so why not? I started swinging and surprised myself. It’s a lesson I still believe in.

Adam: How did you get here? What failures, setbacks or challenges have been most instrumental to your growth?

Dennis: The short answer? The hard way. I don’t have an Ivy League education and my parents weren’t professionals with big jobs, but they instilled in me a few foundational elements: beyond valuing education, they taught me to value learning, how to apply lessons to your life. Secondly, they taught me the importance of strong ethics and extremely high standards. And while it wasn’t always easy, I had this foundation to rely on. I still do today.

I dealt with significant loss over a short period of time at a very young age, losing my father at age 13 and then my maternal grandmother. For some, this could have set them on a very different path, but it prepared me to deal with the hard stuff. I believe that truly successful people don’t fail, but experience diversions that they recover from.

Adam: In your experience, what are the defining qualities of an effective leader?

Dennis: Surround yourself with greatness. I like to think of as talent that demonstrates professional athleticism. Those with the ability to stretch, grow and challenge. The key is to ensure that they are diverse in thought and background but share your values.

Commit yourself to steadfast consistency and don’t waver from that. Don’t be afraid to take that swing.

Adam: Who are the greatest leaders you have been around and what did you learn from them?

Dennis: I’ve always found Ronald Reagan inspirational. His approach to Poland was thoughtful and deft, almost surgical. The ability to engineer the approach he did was ingenious; it taught me to get out of my own echo chamber and not surround myself with yes people.

Another inspiring leader was a former boss. Knowing the company’s future was unclear, I considered another offer. When I sought his opinion, he paid me the ultimate compliment: you have the highest level of character of anyone I’ve worked with. Make sure this is worthy of your integrity. Ultimately, I stayed, but my point is he impressed me with his ability to recognize and articulate that. It’s something that I aspire to do.

Adam: How can leaders and aspiring leaders take their leadership skills to the next level?

Dennis: Disruption is overused but the focus here is on the individual, not an industry. Leaders really ought to disrupt themselves. It’s critical to consistently challenge your own way of thinking and constantly pressure test your convictions. Is that way of thinking holding you back? Be your own disruptor.

Adam: What is the best advice you have on building, managing and leading teams?

Dennis: I said it before and I’ll say it again because it’s that important. Surround yourself with greatness; those that are diverse but share values. The most interesting part of this philosophy is that it takes discipline to manage a senior team of people with differing perspectives. Learn how to extract what you need from each, harness it and develop a harmonized outcome, ideally one that brings you to the right decision.

Adam: What are your hobbies and how have they impacted your development as a leader?

Dennis: I love this question because I believe strongly in creating a culture that not only values wellness and balance but empowers it. For me, hobbies and interests play a big role here. I am a novice fly fisherman with a real love and passion for it. It can be a Zen-like experience and an excellent way to remove yourself from the day-to-day.

I also really enjoy golf because I am competing against myself – trying to better my game. It also teaches great focus. For me, golf is all about self-disruption.

Adam: Is there anything else you would like to share?

Dennis: We’ve covered a lot. If I may leave you with two things: The only way a leader can move forward is to challenge his or her own foundation. Secondly, love what you do and who you do it with. If you can wake up every day and answer those two questions affirmatively, I’d consider that success. 

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