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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...
044: "My Only Competitor Is Me From Yesterday" ft. Jake Stahl
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