Behind the Scenes of Our Executive Masterminds: Why We Prioritize Leadership Growth Every Quarter

Every 90 days, while many businesses are deep in the grind of daily operations, our team is stepping out of the business and into something that’s transformed the way we lead: executive masterminds.

In a recent interview, we shared what really happens at our executive masterminds—why we never skip them, how they’ve shaped our leadership culture, and why small business owners might consider implementing something similar with their own teams.

“The goal isn’t just to grow the business. It’s to grow the leaders who grow the business.” – Kristy

Why We Started Doing Executive Masterminds

As our business expanded into Delaware, Maryland, Pennsylvania, New Jersey, and Florida, we knew we needed something more than Zoom calls and monthly reports. We needed alignment, ownership, and collaboration across divisions.

“We were determined not to operate in silos. These masterminds became our solution to that.” – Wes

Masterminds started as a way to connect our leaders, but they’ve become so much more. They are now a rhythm—an intentional pause—where each leader gets space to reflect, strategize, and grow.

What Happens at a Mastermind

Each quarter, we bring our divisional leaders together for two in-person days packed with:

• Leader presentations using a standardized PowerPoint template
• Deep dives into performance metrics, organizational charts, and growth goals
• Real-time feedback and cross-division collaboration
• Leadership development challenges like speeches or personal reflections
• Team-building outings (because great teams play together, too)

We rotate locations based on our divisions, and tailor each event with something unique. From a Life Wheel reflection to a recent “Bottleneck Challenge” (where leaders tracked every message they had to answer while away), each mastermind is designed to help our team lead more effectively and intentionally.

“Even one day away shows you exactly where the gaps are—and where you’re still the bottleneck.” – Kristy

The Impact: Why It’s Worth It

Even during COVID, when everything was on the line and budgets were tight, this was the one area we didn’t cut.

“When your team is working harder than ever, in the most unstable environment possible, that’s exactly when they need support the most.” – Wes

These masterminds have allowed our leaders to:

• Get out of the weeds and think strategically
• See how other divisions are solving similar problems
• Build real relationships across state lines
• Leave with clarity, confidence, and a renewed sense of purpose

Want to Build Something Similar?

We don’t just do this for ourselves. Through LevelUp2Lead, we help other business owners build similar leadership rhythms into their companies. If you’re looking to grow, scale, and develop a team that doesn’t rely on you for everything—this is a great place to start.

“The magic happens when leaders stop being the hero—and start building a team that doesn’t need one.”

 Interested in building your own executive rhythm?

Let’s talk about how we can design a mastermind that will take your business to the next level. Check out our business services page or email us at [email protected] for more information.