The Bob Ross of Executive Teams

Nope. That’s not a mistake in my LinkedIn bio. I’m the Bob Ross of executive teams.

What does the “happy little trees” guy have to do with executive teams?

It’s a fair question. And the story behind it says everything about how I work.

A few years back, after facilitating a particularly complex strategic session, my colleague Mike pulled me aside.

Working with you is like watching Bob Ross paint. He starts with something gray and cloudy. You’re not sure where he’s going. Then you watch more details emerge, more details emerge. And then all of a sudden—there’s this beautiful painting. You’re not sure how it got there, but it’s amazing.

It’s one of the best compliments I’ve ever received—and why I now proudly call myself the Bob Ross of Executive Teams.

Because that is what I do: I help teams navigate the messy middle, when things feel disjointed or unclear, and arrive at real alignment.

There’s a real methodology behind this magic. What Mike described is my approach to “pulling threads”: creating space, setting the tone, and then weaving together the wisdom that’s already in the room.

It’s one of my superpowers—reading a room’s energy, spotting connections others miss, and bringing the invisible into focus.

Another superpower: toggling between hawk and kestrel mode—big-picture vision and precise execution. Check out my blog post for more on that superpower … and a picture of my tattoo.

Anyway, back to Bob.

His genius wasn’t solely artistic talent—it was how he brought viewers along on the journey. He made complexity feel accessible. He narrated his process. He created space for people to see possibility.

That’s exactly what great leaders do. They don’t just drive outcomes; they bring people along. They create the conditions for others to see possibilities and contribute to the masterpiece.

And that’s what I do when I work with executive teams to find alignment, cohesion, and collaboration.

So while I may not have the glorious hair, I do bring teams along to:

• Trust the process
• Embrace the messy middle
• And build a shared masterpiece.

The next time your team is staring at a blank canvas of possibility, consider that you might need the Bob Ross of Executive Teams: someone to help you see the masterpiece hiding in plain sight.

PS–While Bob is known for his forest scenes, he DID paint desert landscapes. I’m honoring that with a photo of me in Dead Horse Point SP in Utah, looking towards Canyonlands NP, a few weeks ago.

Want to learn more about me, the Bob Ross of Executive Teams? Let’s talk!