My favorite meetings ever

Not all great meetings happen around a table. Honestly, some of the best ones don’t even look like meetings.

Over the years, I’ve learned that changing the setting—just slightly—can shift the tone of a conversation in a big way. Some of my most memorable moments of clarity, connection, or breakthrough didn’t happen in a conference room. They happened while walking, driving, or watching giraffes.

Part of that is wiring. For me, a different environment helps ideas flow better. Conversations go deeper. And if we’re talking strategy? Even better.

Here are three meetings that stuck with me—and why.

1. The “Not-So-Richard-Simmons-Like-But-Also-Not-Romantic Lake Walk”

Back in 2018, Ryan Lassiter of Defining Image and I went for a walk around the lake. The calendar invite called it, “Tim Priebe & Ryan Lassiter’s Not-So-Richard-Simmons-Like-But-Also-Not-Romantic Lake Walk.”

I honestly don’t remember what we talked about that day. But I remember how different the meeting felt. It was the first time I realized how much simply changing the format of a meeting could change what you get out of it.

You listen differently. You process more clearly. And you usually leave more energized.

2. Strategy at the Oklahoma City Zoo with Alisha Allen-Gardner

Earlier this year, I met with Alisha Allen-Gardner to discuss strategy and planning for her two SaaS companies, Easy Time Clock and LilyPad.

Our original plan was to meet at the Oklahoma Science Museum. But when we arrived, it was closed for a private event. So we pivoted and walked over to the zoo instead.

That unplanned change made the meeting even better.

We walked and talked through exhibits, got fresh air, and thought a little more creatively than we might’ve if we’d stayed across a table. It was strategic, thoughtful, and full of momentum—the kind of meeting you walk away from with clarity and next steps.

3. Tulsa drives with Mike Crandall

I worked with Mike Crandall at Sandler Custom Growth Solutions for almost 15 years. For several of those years, we were both members of the National Speakers Association of Oklahoma.

Half of the group’s meetings were in Oklahoma City, and the other half were in Tulsa, which meant a lot of car rides.

And honestly? The drives were sometimes better than the meetings.

We’d cover everything from business to leadership to what was going on in our lives. The movement helped the conversation flow naturally, and some of the best coaching I’ve ever received happened on the drives.

What made these meetings memorable

None of these meetings followed a typical script. They weren’t in traditional settings. But what made them work wasn’t just the format—it was the combination of genuine connection and strategic clarity.

And just as importantly, these weren’t first meetings. I already had a working relationship with each person. We’d had plenty of conversations before this. There was trust. There was openness. We could skip the surface-level stuff and get into what really mattered.

In most cases, that openness came from mutual respect and repetition. We’d spent time building something together already. And that made it easier to say, “Let’s walk while we talk” or “Let’s map this out from 30,000 feet.”

Even when the setting was informal—a walk, a drive, or a trip to the zoo—there was still a clear purpose. The framework underneath the conversation mattered. I’ve spent years building and refining systems to help clients move toward their goals. And those systems don’t disappear when we change locations—they show up more clearly.

For me, the best meetings aren’t necessarily polished. They’re grounded in relationships and direction, and the format just helps bring that into focus.

So if your meetings are feeling stuck or stale, maybe it’s time to shake things up. Try a new environment. Go outside. Take a walk.