I Have Some Questions... artwork

Management · Erik Berglund

I Have Some Questions...

by Erik Berglund

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. 

Latest episodes

Showing 20 · updated from the feed

253: Molly Tschang: "When Crickets Win: Why 'No One Speaks Up' Kills Execution"

Erik and Molly dive into the real skill behind “speaking up” and why organizations fail: they don’t have an accurate shared reality—essential to actually make the best de

Oct 29
1 h 07 min

252: Jason Lauritsen: "Connection as the #1 Performance Booster in the Workspace"

Erik and Jason Lauritsen dig into what “connection” really means at work, what drives it, and how it translates into motivation, performance, and retention. Jason shares

Oct 28
1 h 31 min

250: "Are You Solving the Right Bottleneck with AI?" (Reflections On Drew Mehta)

🧠 Erik’s Take Erik treats this episode as a strategy debrief, not a tech demo. The part that stayed with him is that AI adoption often fails when businesses chase automa

Oct 23
8 min

251: "The Best Leadership Fix Is Focusing On The Fundamentals" (Reflections On Michael Summers)

🧠 Erik’s Take Erik framed the episode as a leadership question, not a political one: how to lead people who genuinely disagree without losing the thread of what actually

Oct 23
9 min

249: Michael Summers: "Can You Run for Office Without Becoming a Walking Controversy?"

Michael Summers shares how he went from professional musician and third-generation business owner to a politics-and-education leader, and why his north star is replacing

Oct 22
1 h 28 min

248: Drew Mehta: "Why Most AI Projects Deliver Faster Garbage Instead Of Business Value"

Drew Mehta explains why so many “AI strategies” fail in practice, and why owner-operators need end-to-end workflow decomposition, not deck-first consulting. We dig into t

Oct 21
1 h 21 min

247: Are You Building the Future, Or Just Getting Better at Running the Present? (Reflections on Shawn Busse)

Erik walked away from his conversation with Shawn Busse thinking less about technology itself and more about what it actually takes to create something new inside a busin

Oct 16
6 min

246: Shawn Busse: "The End Of Cheap Customer Acquisition Is Here. Now What?"

Shawn Busse argues that “growth marketing” hits an inherent ceiling when it becomes a commoditized, copyable process. He uses Hotelling’s law and the “Google beach” to ex

Oct 14
1 h 00 min

245: "Treating Rejection as Information" (Reflections On Wanda J. Herndon)

🧠 Erik’s Take Erik frames this as a short, high-leverage review of his conversation with Wanda Herndon, using her career as a mirror for a recurring workplace pattern: p

Oct 9
6 min

244: Wanda J. Herndon: "What If Every 'No' Is Telling You to Find a 'Yes' Elsewhere?"

Wanda J. Herndon shares how her commitment to telling the truth guided her through corporate PR, and how she navigated being stifled by “sure things” in old-guard compani

Oct 7
1 h 03 min

243: "Everything About Dots: ChatGPT's New Game-Changer" ft. Justin Coats

Justin Coates, co-founder of LearnAir, demos ChatGPT’s new always-on, voice-driven AI agents (Dots) and the “Space” work hub, and explores what changes when work becomes

Oct 6
47 min

242: "How To Ask Your Boss For What You Want And Actually Get It" ft. Alli Murphy

Erik and Alli talk about why “retirement someday” is losing its grip. With a changed job market, uncertainty about longevity, and shifting priorities, professionals are c

Oct 5
8 min

241: "Can Real Expertise Beat Full-Time Availability?" (Reflections On Natalie Hoop)

🧠 Erik’s Take Erik’s takeaway is that the market for expertise is changing at the same time as the meaning of expertise itself is changing. He came away focused on a sin

Oct 2
8 min

240: Natalie Hoop: "The Future Is Fractional, And Here’s Why It’s Accelerating"

Fractional leadership is exploding for good reasons: shifting career expectations, cost optimization, and companies needing C-suite strategy without permanent headcount.

Sep 30
1 h 20 min

239: "Are AI Risks Being Overstated By The Headlines?" ft. Justin Coats

Erik and Justin dig into whether today’s AI risks are being overstated by headlines, and what a practical approach should look like for pacing, alignment, and cybersecuri

Sep 29
43 min

238: "The Four Rs Of Leadership: Reveal, Reset, Rebuild, Reclaim" ft. Alli Murphy

Alli explains why leaders feel terrified about “getting their life back,” and how to work the problem underneath the tactics. Her framework is the four Rs: reveal the rul

Sep 28
19 min

236: "Stop Judging Decisions By Outcomes Alone" (Reflections On Colby Wegter)

🧠 Erik’s Take Erik frames the episode as a short, reflective review, but the real throughline is how self-trust shows up when the stakes are real. He notices that the co

Sep 25
7 min

237: "Manufacturing Trust in a Costly and Uptight System" (Reflections On Danny Chazonoff)

🧠 Erik’s Take Erik treated the episode like a credibility audit disguised as a payments breakdown. On the surface, it was about how card transactions get approved. Under

Sep 25
8 min

235: Danny Chazonoff: "Diversify Or Disappear: Payments Lessons From Sudden Regulation"

Danny Chazonoff, an OG of online payments, breaks down why “Pay Now” is really a high-stakes, multi-handshake system. From early online gambling and wallet innovations to

Sep 24
1 h 18 min

234: Colby Wegter: "Can You Build An Audience While Disliking Social Media?"

Colby Wegter shares how he grew audience and trust without “performing,” why he thinks the customer must lead marketing, and how he rebuilt his life around gut-driven dec

Sep 23
1 h 34 min

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