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I Have Some Questions...
Most people know the headline of a leader’s story. Few know the path it took to get there. This podcast goes beyond titles, book launches and business wins, to explore the lived journey behind the thought leader.
Through deep, unhurried conversations, we uncover the moments that shaped them—the doubts, pivots, convictions, and quiet breakthroughs that built their body of work.
Each episode features authors, coaches, executives, and bold thinkers who have forged their own path. Instead of rehearsed talking points, they’re invited into a space where thoughtful questions unlock something more human. The result is a layered conversation that reveals not just what they preach, but how they became the kind of person who can teach it.
Because we believe the best stories aren’t always told—they’re revealed. And when brilliant people are given the right questions and the room to answer them fully, what emerges is insight you can feel, frameworks you can apply, and a deeper understanding of what it truly takes to lead, create, and contribute at a meaningful level.
I Have Some Questions...
044: "My Only Competitor Is Me From Yesterday" ft. Jake Stahl
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In this conversation, Erik sits down with Jake Stahl, CEO of Orchestraight, to dig into the nuances of adaptability, trust, and leading with presence. From reframing how we think about time to building spaces where people feel seen, Jake offers a refreshingly human approach to leadership growth.
👤 About the Guest
Jake Stahl is the CEO of Orchestraight, a consultant, and a coach who helps organizations unlock adaptability through people-centered learning and leadership. With a background spanning corporate training, coaching, and systems thinking, Jake’s mission is to create environments where leaders and teams thrive by aligning purpose with practice.
🧠Conversation Highlights
- Why adaptability—not rigid planning—is the defining skill of modern leaders.
- How trust is built less through grand gestures and more through consistent presence.
- The difference between managing time and stewarding energy.
- Why psychological safety is a precursor to performance.
- Jake’s own path from structured environments into the dynamic space of leadership development.
đź’ˇ Key Takeaways
- Adaptability is not about being reactive, but about holding shape while flexing.
- Leadership presence means showing up consistently in ways that build trust.
- Coaching leaders isn’t about fixing—it’s about creating space for reflection and choice.
- Growth happens at the edge of discomfort, not in the safety of autopilot.
- Effective leaders are translators: they make complexity accessible to their teams.
âť“ Questions That Mattered
- What does it mean to lead with adaptability instead of rigidity?
- How can leaders create trust without overengineering it?
- In what ways is time management overrated compared to energy management?
- What role does psychological safety play in unlocking team performance?
- How can CEOs reimagine leadership to help organizations learn and adapt?
🗣️ Notable Quotes
- “Adaptability isn’t about throwing out the plan—it’s about knowing when to hold it lightly.” – Jake Stahl
- “Trust is built in the everyday moments, not the big events.” – Jake Stahl
- “Leadership is less about controlling outcomes and more about creating the conditions where people can thrive.” – Jake Stahl
- “When leaders translate complexity into clarity, they give people the gift of focus.” – Erik Berglund
đź”— Links & Resources
- Connect with Jake on LinkedIn
- Check out Jake's company, Orchestraight
- Stay on the lookout for Jake's new book: Own The Room - From Invisibility to Unforgettable