105: "Do You Know What Kind of Puzzle Piece You’re Actually Looking For?" (lessons from Brett Jesson)
🧠 Erik’s Take
In this post-interview reflection, Erik revisits key insights from his conversation with Brett Jesson, Chief Growth Officer at DDC Group. What stands out isn’t just Brett’s strategic clarity—it’s the way he pairs operational rigor with a deeply human approach to leadership. Erik dives into three standout themes: the underestimated power of fiction in leadership, the rise of small powerhouse teams, and the brutal honesty required for better hiring. This is a thoughtful unpacking of how leadership evolves when you're willing to look inward first.
🎯 Top Insights from the Interview
- Fiction builds empathy. Reading novels helps leaders see the world through others’ eyes—and leads to stronger “off the pitch” relationships.
- Small, high-powered generalist teams outperform bureaucracies. Versatility + trust = agility.
- Hiring well starts with knowing yourself. If you don’t understand your team’s strengths and gaps, you can’t pick the right puzzle piece.
- Speed matters in hiring recovery. Catching a wrong hire in 30–60 days is healthy. Waiting 12–24 months is a costly culture problem.
- Generational shifts are leadership tests. Leading millennials and Gen Z is no longer optional—and it’s not their fault, but it is your responsibility.
🧩 The Personal Layer
Erik reflects on how Brett’s love of fiction and leadership intersect in surprising ways. From Ender’s Game to Project Hail Mary, storytelling helps leaders build empathy and see patterns in human behavior—both in real life and on their teams. It’s not just intellectual—it's emotional. Brett’s commitment to leveling up as a human, not just a title, is a model Erik finds both refreshing and necessary.
🧰 From Insight to Action
- Read fiction. Not as escape, but as a tool for emotional fluency.
- Build generalist-heavy teams and reduce "connective tissue" friction.
- Redesign your hiring process to test for culture, not just competence.
- Normalize admitting a hire isn’t working—faster, not later.
- Reflect: Are you adapting your leadership style to the team you have—or the one you wish you had?
🗣️ Notable Quotes
“You can't walk in someone’s shoes if you've never imagined them.”
“Friction often lives in the connective tissue—small teams cut that out.”
“Hiring starts with knowing what you can and can’t train.”
“The wrong person can demolish a small, high-powered team.”
“By 2030, millennials and Gen Z will be the majority—it’s not their fault, but it is your responsibility.”
🔗 Links & Resources
