104: "How Do You Build Culture That Isn’t Just a Slide Deck?" ft. Brett Jesson
In this episode, Erik sits down with Brett Jesson, a strategic leader driving growth at a global business process management enterprise. What unfolds is a conversation that transcends business talk and drills into trust, culture, and the very human side of leadership. From career pivots to hiring with humility, Brett shares how he’s learned to lead small, high-performing teams in big, complex systems—without losing sight of what makes people thrive. It’s a masterclass in emotionally intelligent leadership for scale.
👤 About the Guest
Brett Jesson is a senior executive at The DDC Group, where he leads commercial operations for the EMEA region. His career spans client growth, team building, and market origination in highly diverse environments. Brett is known for his strategic clarity and people-first approach—balancing rigor with reflection and operational excellence with emotional insight. He brings both humility and hard-won wisdom to this conversation on leading at the intersection of culture, trust, and performance.
🧭 Conversation Highlights
- Why small, high-performing teams are often the engine behind outsized impact.
- The hiring challenge: balancing instinct, bias, and trust in fast-scaling environments.
- “Pressure without expectation”—how Brett was raised and how it shapes his leadership style.
- What makes culture more than just words on a wall—and how to make it live in the work.
- Navigating imposter syndrome and identity across roles, geographies, and seasons of life.
💡 Key Takeaways
- Trust scales faster than any other strategy. Brett unpacks how shared values and high-trust teams create momentum in uncertain markets.
- Culture must live in the day-to-day. It’s not defined by a slide deck, but by what your team defends, promotes, and expects in real time.
- Hiring is about alignment, not perfection. You won't get it right every time—but the faster you admit and adjust, the better.
- Great leadership is not knowing all the answers—it's asking better questions. Brett models humility and intellectual curiosity.
- The best leaders own their blind spots. Self-awareness isn’t a luxury; it’s a multiplier.
❓ Questions That Mattered
- How do you build trust in distributed, multicultural teams?
- What kind of pressure leads to growth—and what kind shuts people down?
- Why is “click” in hiring both powerful and dangerous?
- How do you make sure your culture lives beyond the onboarding deck?
- What does it take to lead in ambiguity without needing to control?
🗣️ Notable Quotes
“The best cultures are validated by clients—not just internal slogans.”
“Sometimes hiring is a bet. It’s a feeling. And sometimes it works, and sometimes it doesn’t.”
“We’re a small team, so we have to pick the right targets, the right people—and then go get it done.”
“It’s not about being right—it’s about staying in alignment.”
“Imposter syndrome isn't the enemy. It’s often the sign that you’re stretching into something real.”
🔗 Links & Resources
