Empowering Creativity: An Interview with Kregg, Creative Director at High Five Media

At High Five Media, creativity isn’t just a department, it’s a mindset. We recently sat down with Kregg, our Creative Director, to talk about leadership, growth, and what it really means to guide a creative team. His philosophy is simple yet powerful: trust your people and let their talents shine.

The Foundation of Great Leadership: Hiring and Trust

When asked what advice he’d give to someone aspiring to a high-level creative role, Kregg didn’t hesitate. “The first step is the most important one,” he said. “It’s who you hire. Hire competent people, people with a ton of potential, and let them do their magic.”

For Kregg, great leadership isn’t about control, it’s about confidence. “Not everything is going to be high-level when someone’s starting out,” he explained. “But if it’s really good and they’re getting better each time, let it go. Let the talents begin to believe in themselves.”

That belief, he says, is what unlocks creativity and growth. When people feel supported and valued, they don’t just meet expectations, they exceed them. “When someone lets you know you’re doing well and you’re good at what you’re passionate about, you just get better because you begin to believe.”

Breaking the Stereotype of the ‘Tough’ Creative Director

Kregg knows that creative directors often have a reputation for being hard to work with, the “my way or the highway” type. But that’s not the kind of environment he wants to build.

“As my career started advancing, I made a decision that I didn’t want to be that,” he shared. “I want people to grow underneath me and not just become glorified production artists, people who never get outside the shadow of creating someone else’s work.”

For him, leadership isn’t about being the loudest voice in the room, it’s about creating space for others to find theirs. “I don’t feel like a creative director has to have all his or her ideas be the final say,” he said. “If someone comes to me with something that’s magic, I’ll take my stuff right off the desk and say, go with that.”

The Joy of Watching Others Succeed

What drives Kregg most is seeing others succeed. “I’m very passionate about seeing people do the best they can and improve, seeing them walk away with a smile, knowing this is going to be awesome,” he said.

That passion for growth and positivity is what sets him apart. He believes in nurturing confidence, celebrating progress, and giving people the freedom to learn through experience. “You can push, direct, and critique,” he said, “but at the end of the day, it has to be their own learning experience that helps it stick.”

A Legacy of Creative Freedom

Kregg’s approach to creative leadership is a refreshing reminder that great work comes from collaboration, not control. His philosophy of hiring well, trusting deeply, and empowering consistently continues to shape the culture at High Five Media.

And as for what keeps him going after all these years? It’s simple. “It’s very cool to see people carry that passion,” he said. “Even after all this time, that’s what it’s all about.”