A Culture Worth Copying: How One Insurance Agency Invests in People and Progress

I recently spent a day with an insurance agency that reminded me what leadership really looks like.

They didn’t bring me in because they were falling behind. They brought me in because they were ready. Ready to lean into AI, ready to sharpen their team's skills, and ready to build the kind of intentional culture that makes people proud to be there.

While I was there to talk about automation, prompts, and predictive analytics, it was lunch that told me everything I needed to know.

Let me explain.

They’re Not Guessing. They’re Investing

When most people think of tech in the insurance space, they think of patching problems: plug in a CRM here, automate a renewal email there, slap a dashboard on some Excel chaos and call it a strategy.

But this agency was doing something different. They weren’t reacting to pain. They were planning for the possibility.

They had set aside a full day for me to work with their team. I wasn’t there to lecture, but to roll up our sleeves together and explore how AI could actually work in their context.

We spent four hours deep-diving into how to make Copilot a practical tool for their agency. Not just something that sounds exciting, but something that actually saves time and gets used.

We explored how to:

• Build effective, easy-to-understand prompts that generate useful results
• Analyze information faster and more clearly
• Write better proposals with less friction
• Create prospect communications that are clear, persuasive, and human
• What’s real and what’s hype when it comes to AI in the insurance space

The team didn’t just nod along. They leaned in. They asked real questions. They explored ideas. It was clear that they weren’t there because they had to be. They were there because their leadership believed in investing early in tools that could pay off long term.

How many agencies spend real money and block off real calendar time to upskill their team on tech that might define the next decade?

Not many. And that’s exactly why this one stood out.

The Fun Committee (Yes, Really)

After a morning of AI strategy and workflow redesign, I sat down to eat lunch with the team. I sat with two of the younger team members who referred to themselves as the “Fun Committee.”

I smiled, thinking it was a joke. It wasn’t.

The Fun Committee is 100% real, and I asked them to tell me about their duties. That’s when the two Fun Committee members absolutely lit up.

It was clear that they took pride in the responsibilities of planning fun social activities for the agency staff. They told me that they plan one event a month. Everything from holiday parties to a staff picnic.

Even those not on the committee jumped in to talk about how much they enjoyed the events.

This wasn't a forced HR initiative. It was a grassroots, team-led culture in full bloom.

It was also clear that leadership supported it with a real budget and full trust. No micromanaging. They empowered a group of employees to build the kind of place they wanted to work in, and the ripple effects were everywhere.

This is what happens when you move beyond “casual Fridays” and really empower your team.
People bring their full selves to work. And they bring each other along with them.

Two Investments, One Clear Message

I came to talk about artificial intelligence.
I left talking about cultural intelligence.

This agency’s leadership didn’t separate performance and happiness.
They saw the link and they built a strategy around it.

Investing in tech says, We care about how you work.
Investing in people says, We care about who you are.

They’re not mutually exclusive. In fact, when done well, they reinforce each other:

• A team that feels valued is more open to change
• A team that gets training is more confident in its tools
• A team that feels connected is more collaborative, more supportive, and more likely to stay

The agency I visited didn’t say these things. They lived them.
And they lived them through actions that were as different as AI workshops and ice cream socials.

That’s not fluff.
That’s smart leadership.

If You Want a Team That Believes, Start By Believing In Them

Want to replicate this in your agency?

You don’t need a 10-point culture manifesto. You don’t need motivational posters or a Slack channel for inspirational quotes.

Start with these two questions:

1. Where are we investing in our team’s growth?
   (Do they get training, tools, and support to evolve with the industry?)
2. Where are we investing in our team’s happiness?
   (Do they feel connected, trusted, and empowered to shape the culture?)

Then act on the answers.

Give your team real training on real tools like AI.
And give them space to build traditions, fun, and connection into the day-to-day.

Set aside a budget.
Back off on the approvals.
Let your people build something, because they will.

Final Thought: Culture Isn’t an Accessory—It’s the Engine

What I saw at this agency was simple, but powerful.

They weren’t running on slogans.
They were running on trust.
They weren’t scrambling to keep up.
They were looking around the corner, preparing for what’s next.

It wasn’t luck.
It was leadership.

Culture doesn’t have to be complicated. But it does have to be real.
And real culture? It starts with a choice:

To invest in people.
To invest in growth.
And to make both of those things part of the same conversation.

This agency did that.
And it showed.