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A Conversation with Damon Wellman
Robert Trahan
Partner, Mass Productive
Damon Wellman’s career spans decades and industries, from engineering and construction to sports management at the Golden State Warriors. In this conversation, he shared insights into leadership, business development, and fostering creativity within structured environments. Below are highlights from the interview, framed with lessons for professionals seeking to lead effectively and creatively.
When the conversation turned to business development, both Damon and Robert reflected on the challenges and rewards of maintaining consistency while avoiding the high-pressure pitfalls of traditional sales.
Rob: I just keep comparing it to something like a Roth IRA. You keep putting the feelers out there, and over time it grows into something sustainable. It’s nice, but the business development side is something I’m learning—like, I don’t need to kill myself. I just need to be consistent.
Damon: Exactly. And what you said about consistency is so important. When we do work, we do really good work—we give 120%. No cutting corners. But yeah, business development has that edge where you’re cold calling or following up on warm leads, trying to heat them up. That part can be uncomfortable, especially when there’s pressure to promise things you can’t control.
Rob: That’s what I hate about sales—the pressure to push. What I like is developing relationships. If work comes from it, great. If not, I still have the relationship.
Damon: I love that approach, too. Sometimes, six months or even a year later, someone will come back and say, 'Remember when we talked? Let’s work together.' That’s what makes it all worth it.
Larger organizations often suffer from bureaucratic inertia, where layers of management stifle the autonomy needed for teams to thrive. Damon shared his strategies for working around these challenges.
Rob: In startups, it’s all about 'move fast and break things,' but in larger organizations, there’s so much process and management. You get promoted for other reasons, and now you’re in charge of people doing work you don’t understand. So instead of enabling them, you micromanage. How do you work around that?
Damon: That scenario plays out everywhere. In dynamic industries like sports, the mindset is, 'It’s okay to fail.' But in places like airlines or pharmaceuticals, the margin for error is tiny, so they overmanage. You see it in things like daily status reports, remote work resistance, or just this obsession with control.
Rob: Yeah, and as a consultant, you’re often hired to fix something they could solve internally, but no one inside wants to take the risk.
Damon: Exactly. You have to build trust by showing value immediately. Start with small wins—something manageable that makes people say, 'Okay, you care about this organization.' That trust grows, and you can tackle bigger problems.
Damon and Robert discussed the tension between creativity and process, using travel as a metaphor for how organizations can strike the right balance.
Rob: How do you create processes that allow for creativity? It’s like planning a trip. You need mile markers, but you also need room for exploration.
Damon: I love that analogy. Everyone is creative in their way. Some people thrive in structure, and others need flexibility. I’ve worked with developers who hated daily check-ins. I stopped asking, and at the end of the week, they delivered incredible work—on time, with extra features. That’s their creative comfort zone.
Rob: It’s about finding what works for each person. I think that’s often overlooked in larger organizations, where the process becomes the goal instead of the tool.
The conversation shifted to leadership, and Damon shared a guiding principle that has shaped his approach: empowering others to excel.
"Your job is to enable people—not control them."
Rob: Why aren’t more leaders like that? So many just say, 'Do what I tell you.' They don’t care about understanding people.
Damon: I came to an early realization: I’m never the smartest guy in the room. My strength is connecting smart people and giving them the space to shine. Leaders get it wrong when they try to be the smartest and the boss. Your job is to enable people—not control them.
Rob: It’s so dignifying to ask, 'How would you do this?' It shows respect for their expertise.
Damon: Exactly. Let people own their work. If they run into trouble, step in as support, not a dictator. That builds respect and trust.
Consistency Builds Relationships: Business development is less about aggressive tactics and more about consistent effort and genuine relationships. Trust takes time but pays dividends.
Quick Wins Build Trust: When working with large organizations, start with manageable projects to demonstrate value and earn trust for larger initiatives.
Personalized Processes Unlock Creativity: Every team member has a unique way of working. Effective leaders recognize this and adapt processes to fit individual strengths.
Empowerment is Leadership: The best leaders don’t try to be the smartest in the room. Instead, they create conditions for others to excel and trust them to deliver.
Understand Before Acting: Whether as a leader or a consultant, understanding the intent and emotional context of a project ensures better decision-making and alignment.