Leading with Creativity: 3 Business Lessons from an Abstract Painter

This article was written by Chad Schoonmaker and published by Crossroads Professional Coaching.

When I’m not elbow-deep in Basecamp, emails, or managing the marketing team at Crossroads, you’ll probably find me in front of a blank canvas, attempting to create another abstract painting. People ask me, “How long have you been into art?” my response is always the same, “my whole life.” In the 90s,  I would pause Disney movies at certain scenes and draw on paper what was on screen. My grandfather was an artist, and my aunt, who was endlessly creative, inspired me early in life to explore artistic expression.

Painting has always been more than a hobby for me—it’s a way of processing the day or events in my life. Every color choice is a decision, every layer is an experiment, and every piece is an evolution of thoughts or prayers. As an abstract painter, I’ve learned that each decision affects the final work, whether I realize it in the moment or not.

And you know what? Leading a team is very similar.

Every day, small business owners make countless decisions that shape their company’s success. It takes courage to start and run a business, but it also takes creativity to keep it moving forward. Whether in my studio painting or working at Crossroads, I’ve realized that success comes from setting a vision, embracing the unexpected, and knowing when to step back and let things evolve.

Here are three leadership lessons I’ve learned from my time in the studio that might help you as you lead your team.

1. Embrace Flexibility

When I start a new painting, I never know exactly how it will turn out. Actually, I never know at all. I just stay open to the possibilities—because, truly, they’re limitless. I lay down color, texture, and movement, letting the composition take shape organically. Sometimes, I stop and think, What am I even doing? Why did I put that color there?

Then I remember Bob Ross’s golden rule: “There are no mistakes—just happy little accidents.”

The same mindset applies to leading a small team. In business, things don’t always go as planned. Clients change direction. Strategies fail. But sometimes, those “accidents” lead to new discoveries—better ideas, new perspectives, and ultimately, GROWTH!

Tip: Encourage your team to experiment.** Give them the freedom to test new approaches, try bold ideas, and learn from outcomes. Share your own missteps and what they taught you. When failure is seen as part of the process, your team will feel empowered to take risks and innovate.

2. Strong Foundation, Balance Structure

Every painting has an underpainting—the foundational layers beneath the surface that set the tone for the entire piece. You may not see it in the final work, but if it’s not there or done correctly, the painting won’t feel right.

The same is true in leadership. A team needs a solid foundation—clear expectations, strong communication, and trust—to function well. Without it, things fall apart.

Todd Henry, in Herding Tigers, emphasizes this balance between structure and creative freedom:

“If you want to unleash the best work from your team, you must provide them with both stability and challenge.”

That means setting clear goals while also allowing room for flexibility. It means meeting regularly with your team, not just to check in on deadlines, but to ask the right questions that challenge their thinking.

Here are some great conversation starters from Herding Tigers to help your team stay on track:

• What do you see that you think others don’t?
• What’s something obvious that we’re missing?
• What worries you about this project?
• What opportunities aren’t we exploring?
• Where are we getting off track?
• What’s the best thing we’re doing right now?

Tip: Set clear goals but allow room for creative problem-solving.** Meet regularly with your team and ask open-ended questions that encourage insight and ownership. When your team feels heard, they’ll feel more invested in the work.

3. Trust the Process—and Your People

One of the hardest parts of being a painter is knowing when to stop. It’s easy to overwork a piece, adding layers upon layers, until suddenly, I’ve lost the energy that made it special in the first place.

Leadership works the same way. Micromanaging stifles creativity. When you hover over every decision, your team won’t take ownership of their work—they’ll just wait for you to tell them what to do.

Todd Henry warns against this in Herding Tigers:

“If you don’t allow your team to own the problems, they’ll never own the solutions.”

Your job as a leader isn’t to do everything yourself—it’s to set the vision, give your team the tools they need, and then step back so they can deliver.

Tip: Trust your team.** Offer guidance, but don’t over-direct. When you empower your people to take ownership of their work, they’ll develop creative solutions and feel more fulfilled in what they do.

Final Thoughts

Being both an artist and a leader in a small business has shown me that business and creativity are deeply connected. A successful team—like a successful painting—requires vision, the bravery to keep going, and the courage to embrace the unknown.

By applying these lessons you can lead with both strategy and creativity, allowing your team to thrive in an ever-changing business landscape.

And remember, whether it’s in business or on a canvas, the best work often comes from a few happy little accidents.