I Have Some Questions...
What if leadership wasn’t about having the answers—but about asking better questions?
On "I Have Some Questions…", Erik Berglund – a founder, coach, and Speechcraft evangelist – dives into the conversations that high performers aren’t having enough. This isn’t your typical leadership podcast. It’s a tactical deep-dive into the soft skills that actually drive results: the hard-to-nail moments of accountability, the awkward feedback loops, and the language that turns good leaders into great ones.
Each week, Erik explores a question that has shaped his own journey. Expect raw, unpolished curiosity. Expect conversations with bold thinkers, rising leaders, and practitioners who are tired of recycled advice and ready to talk about what really works. Expect episodes that get under the hood of how real change happens: through what we say, how we say it, and how often we practice it.
This show is for driven managers, emerging execs, and anyone who knows that real growth comes from curiosity rather than charisma.
Subscribe if you’re ready to stop winging it and start leading with intention.
I Have Some Questions...
099: "Balancing Intuition and Iteration" (lessons from Chase Damiano)
🧠Erik’s Take
In this reaction episode, Erik reflects on his conversation with Chase Damiano—COO turned systems thinker, father-first decision maker, and founder of Humans at Scale. What stood out most? Chase doesn’t just talk strategy—he tests it. Erik highlights how Chase treats business like a living lab, combining intention, iteration, and humanity into every decision. This episode zooms in on what it really means to lead with intentionality, how systems thinking plays out in the real world, and why experimentation might be the most underrated leadership muscle of all.
🎯 Top Insights from the Interview
- Treat your business like a laboratory — Chase runs experiments, not assumptions. Every major move, from coffee trikes to national distribution, was a test.
- Systems thinking as a leadership edge — With a background in systems engineering, Chase applied operational rigor to startups and service-based businesses alike.
- Intentionality isn’t just personal—it’s operational — Whether choosing where to live or what to launch, Chase methodically tests alignment with values.
- Values-driven decisions scale — From turning down a promising job to stay close to his son, to shaping his new company, Chase walks the talk.
- Even your best ideas are just hypotheses — From sales scripts to team culture, everything is a test—until feedback proves otherwise.
🧩 The Personal Layer
Erik shares how Chase’s lens of systems + intention got him thinking about his own decisions—especially around parenting, leadership, and product testing. There’s a quiet kind of boldness in how Chase lives: methodical, values-aligned, and open to pivoting. That balance between rigor and flexibility? Erik sees it as an antidote to stuck leadership.
🧰 From Insight to Action
- Ask yourself: “Am I treating this strategy like a test?”
- Revisit your personal or professional goals—are they aligned with your values or inherited assumptions?
- Design small feedback loops for your next big decision. What would it mean to test it before scaling it?
- Consider how empathy + systems thinking can coexist in your leadership style.
- Journal prompt: “Where am I stubborn where I should be curious?”
🗣️ Notable Quotes
“Our businesses are just experiments.”
“The more you can recognize you’re in the middle of a test, the easier it is to treat pushback as feedback.”
“You kind of have to know where you want to go in order to figure out the best path to get there.”
“Intentionality and systems thinking—what a deadly one-two punch.”
“Every interaction—product, sales, culture—it’s all a lab if you’re willing to see it that way.”
đź”— Links & Resources