Gilbert Leadership: New Program. New Town. New Me.

Written by Stuart Preston, Founder of Cingularis

When I first went through Gilbert Leadership, I was part of Class XIV – the Roman numeral era, which made the whole thing feel a little more official than it probably needed to. This year, I’m graduating with Class 34.

That small change in naming says more than I expected. Somewhere between Class XIV and Class 34, Gilbert Leadership became a different program, Gilbert became a different town, and I became a very different person.

That is why I came back. I was not trying to relive an old experience. I was curious about what the program had become, what Gilbert had become, and what I might see differently after nearly twenty years of life, work, loss, growth, and perspective.

The biggest difference I noticed this time was how polished and intentional the program felt. That is not a criticism of the experience I had twenty years ago. Gilbert Leadership was meaningful then. But twenty years of learning, refining, listening, adjusting, and improving shows up.

This time, the program felt both professional and fun. It was organized without feeling stiff. It was structured without losing its personality. There was a sense that the steering committee and program leaders knew not only what they were doing, but why they were doing it.

Their energy mattered. The people leading each part of the experience were involved, positive, and genuinely invested. That kind of leadership is contagious. When the people creating the experience care deeply, the class feels it.

Gilbert also feels different than it did when I first went through the program. Back then, the town had just come through a major growth spurt. Roads were changing. The 202 was still becoming part of daily life. Town leadership looked different. The Chamber felt different. Gilbert was growing quickly and still shaping what it wanted to become.

Twenty years later, Gilbert is bigger, more developed, and more complex. Roads have expanded. New neighborhoods and businesses have appeared. The town has continued to grow in ways that are obvious if you have been paying attention for any length of time.

But what stood out to me most was not the growth. It was the maturity.

Gilbert feels like a town that kept building without completely forgetting itself. The values, civic pride, and desire to make this place better are still here. They just show up now through a larger, more established, more layered community.

Of course, the town and the program were not the only things that changed.

When I went through Gilbert Leadership the first time, I was younger and more focused on building my business. I was probably thinking about what I could get FROM the Chamber, the town, and the program. I had leadership experience. I had led people in business. I had served as a platoon leader in the Army. I probably walked in believing I already knew a lot about leadership.

Which is often when life begins the process of proving otherwise.

Between Class XIV and Class 34, life happened. Successes happened. Failures happened. Lessons happened. And ten years ago, I lost my son Ian to suicide.

That kind of loss changes the way you see everything. It softened some edges. It reshaped what I value. It cracked open parts of me that had been too focused on achievement, success, and proving myself.

But my story is just my story.

None of us are the same people we were 7, 10, 15, or 20 years ago. Life has a way of reshaping us. Sometimes through success. Sometimes through failure. Sometimes through raising children, changing careers, losing people we love, overcoming challenges, or discovering a new sense of purpose.

If you went through Gilbert Leadership years ago, take a moment and ask yourself: How has life changed you since then? What experiences have shifted your perspective? What do you value now that you did not value before?

Chances are, you would not walk into the program today as the same person who walked into it the first time.

So when I came back to Gilbert Leadership, I was not asking the same questions.

The first time, I was probably asking, “What can I get from this?”

This time, I was asking, “Where can I serve?”

That is the part I would want other alumni to consider.

You do not come back to Gilbert Leadership because you missed something the first time. You come back because the program is different. Gilbert is different. And you are different.

You bring a different life with you now. You bring different questions, different experience, and probably a different definition of leadership. What looked like opportunity years ago may now look like connection. What once felt like networking may now feel like community. What once seemed like a program may now feel like a doorway back into the town.

That was the gift for me. Gilbert Leadership gave me a way to re-enter Gilbert with fresh eyes and a more open heart.

And yes, if none of that convinces you, there is also the opportunity to race around a track at 80 miles per hour with a Gilbert police officer.

Which, for the record, was not part of Class XIV.

Leadership is not something you finish. It changes as you change. It deepens as your life deepens. It becomes less about title, achievement, or status and more about service, connection, and contribution.

So if you are a Gilbert Leadership alum, I would not ask, “Should I do the program again?”

I would ask something better:

Ask yourself: What version of you would walk into Gilbert Leadership today?

That answer might be exactly why you should come back.

Stuart Preston is a Gilbert business owner, community advocate, and founder of Cingularis, helping businesses that do good do even good-er.