I Have Some Questions...

Erik Berglund
  • 5.0 (41)
  • Management
  • Updated Daily

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. 

  1. 170: "What Changes When You Start Leading Leaders?" ft. Alli Murphy

    19h ago

    170: "What Changes When You Start Leading Leaders?" ft. Alli Murphy

    Erik and Alli compare notes on what goes wrong when high-performing leaders move from managing individual contributors to leading leaders. They highlight recurring gaps, including losing ground-level visibility, suddenly being expected to influence strategy at higher levels, and struggling to develop and communicate effectively with the leaders beneath you. 🧭 Conversation Highlights The IC to people-manager transition often isn’t taught, so the “leader of leaders” shift compounds the learning-by-trial-and-error problem.A common trap is staying in the weeds and trying to personally verify what’s happening below, rather than building systems to keep you connected without micromanaging.New leadership layers add boardroom dynamics: you’re expected to influence peers and strategy, not just execute plans handed to you.When people are promoted over peers, they can develop a “prove I earned this” posture and also face more incomplete-information and uncertainty.💡 Key Takeaways Leaders of leaders need leverage, not more hands-on work: the goal is to stay informed via systems and influence rather than re-owning problems.Strategy competence becomes an operational skill. You need time to understand what senior leadership cares about so you can connect that to execution.Communication and development channels often break when you lose direct visibility. You need a clearer framework for discussing performance and coaching needs with the leaders under you.Delegation and coaching are the foundational multiplier. If you get it right at the IC level, you can teach it downward through your leadership layer.❓ Questions That Mattered What common gaps show up when people move from leading ICs to leading leaders without being supported through the transition?How should new leaders adjust when they no longer have ground-level visibility but are still accountable for outcomes?What changes when you enter boardroom and peer-influence dynamics rather than only executing strategy?Which single competency would you bet on for someone preparing for the “uncharted water” of leading leaders?🗣️ Notable Quotes “their job is not therapist.”“Sometimes there isn't one.”“learn how to delegate well and actually coach people.”“that game of incomplete information is often new when you move into this lead leaders role”🔗 Links & Resources Listen To Other Episodes Co-Hosted With Alli

    19 min

  2. 3d ago

    168: "Building Culture That's Actually Lived, Not Just Talked About" (reflections on JD Hilzendager)

    🧠 Erik’s Take Erik reflects on his conversation with JD Hilzendager as a study in intentional culture, unconventional thinking, and problem-first leadership. What stands out most isn’t just what JD has built—but how he thinks about building it. This episode is less about tactics and more about mental models: how culture is formed, how individuals decide to break away from the norm, and how great organizations create value by relentlessly solving problems.  🎯 Top Insights from the Interview Culture is language, not perks. It’s the phrases, questions, and behaviors that become so normal they’re unconscious Different thinking creates different outcomes. If you want different results, you can’t follow the same playbook as everyone else Problem-solving is the real job. The best organizations don’t just execute—they continuously identify and solve “stupid things” Technology adoption is a cultural challenge. Tools only work if people feel safe using them and evolving their roles Great companies create roles, not just fill them. When work changes, the best leaders redefine value—not eliminate people 🧩 The Personal Layer Erik connects deeply with JD’s mindset around not fitting inside traditional corporate structures. There’s a shared recognition that some people are wired to question, push, and rethink systems—not just operate within them. He highlights the tension many professionals feel: Do I follow the path that’s proven and stable? Or do I pursue something that aligns with how I naturally think? There’s also a deeper appreciation for how culture isn’t accidental—it’s built slowly, intentionally, and often invisibly over years. 🧰 From Insight to Action Audit your culture through language. What phrases are “normal” in your team? What does that reveal? Challenge default thinking. If you’re getting average results, ask: where am I just doing what everyone else does? Find one “stupid thing” each week. Identify inefficiencies or broken processes—and take ownership of solving them Reframe your role around value creation. Don’t cling to tasks—focus on problems you’re uniquely positioned to solve Make change feel safe. When introducing new tools or ideas, show people where they fit—not where they’re replaced 🗣️ Notable Quotes “Culture is what’s normal to the tongue.” “If you’re doing what everyone else is doing, you’re going to get the same results.” “Find one stupid thing each week.” “Your job is to find problems and solve them.” “Great companies don’t just adopt technology—they adapt their people.” 🔗 Links & Resources Listen to JD Hilzendager's Episode

    11 min

  3. 3d ago

    169: "Are We Really Preparing Like it Matters?" (reflections on Scott Anderson)

    🧠 Erik’s Take Erik reflects on his conversation with Scott Anderson as a rare opportunity to learn from someone who has led where most people will never go—combat zones, humanitarian crises, and high-stakes environments where failure has real consequences. What stands out most isn’t just Scott’s experience—it’s the contrast. The gap between how leadership must operate in those environments versus how casually it’s often approached in business. Erik leans into that tension. If we claim the stakes are high in our work, why don’t we prepare like they are? 🎯 Top Insights from the Interview Preparation scales with consequences. In the military and UN, missions often require 30–50% of total time spent in preparation. In business, it’s often close to zero. The range of “unknowns” defines the environment. In conflict zones, unpredictability is extreme—routes disappear, environments change instantly. In business, most risks are slower and more visible. You don’t get better without exposure. Leaders improve through reps—either real-world experience or structured simulation. There’s no shortcut. Mentorship accelerates everything. Watching how great leaders think—not just what they do—is one of the fastest ways to grow. Business leadership under-trains for reality. There’s a disconnect between perceived stakes and actual preparation in corporate environments. 🧩 The Personal Layer This episode hits a familiar nerve for Erik. He’s spent his career in environments where performance matters—but this conversation forces a deeper question: Are we actually preparing like it matters? There’s a quiet tension underneath his reflection:  We say things are important  We feel pressure to perform  But we rarely build the systems to truly practice And that gap is where performance breaks down. Scott’s experience becomes a mirror—highlighting how much of modern leadership is reactive instead of trained. 🧰 From Insight to Action Audit your preparation habits. Before your next “important” meeting, ask: Did I actually prepare—or just show up?Create practice environments. Don’t wait for real stakes. Simulate them. Role play, rehearse, pressure test. Expose your team to your thinking. Don’t just show outcomes—walk people through how you arrived there. Invest in reps, not just knowledge. Reading and learning isn’t enough. Build muscle memory through doing. Redefine what “high stakes” means for you. If it matters—treat it like it matters. 🗣️ Notable Quotes “The higher the stakes, the more time you spend preparing.” “In business, we say the stakes are high—but we don’t prepare like they are.” “You get better through exposure—either by doing it or by watching someone who has.” “The range of what can go wrong in a conflict zone is almost unimaginable.” “We don’t train leaders—we just expect them to perform.” 🔗 Links & Resources Listen to Scott Anderson's Episode

    7 min
  4. 167: Scott Anderson: "What Does Leadership Look Like When Lives Are Actually on the Line?"

    4d ago

    167: Scott Anderson: "What Does Leadership Look Like When Lives Are Actually on the Line?"

    In this long-awaited conversation, Erik sits down with Scott Anderson, who has served over 20 years in the military and is now a well-established leader in corporate America. Scott brings a rare blend of crisis-tested leadership and operational discipline into the business world.  👤 About the Guest Scott Anderson is a seasoned leader with over 20 years of experience across the U.S. Army, United Nations, and federal agencies. He led humanitarian and security operations in Gaza and Afghanistan, managed teams of up to 14,000 people in high-risk environments and oversaw billion-dollar operations under extreme uncertainty Now, he serves as COO of a growing property management company. 🧭 Conversation Highlights 1. Leadership Changes When the Stakes Are Real. When decisions can cost lives, leadership stops being abstract. You don’t get to hide behind theory—you have to own outcomes, fully. 2. Slow Down to Make Better Decisions. In chaos, the instinct is to speed up. Great leaders do the opposite—they slow down just enough to filter signal from noise. 3. Authenticity Beats False Reassurance. You can’t promise safety in a war zone. But you can be honest. Trust is built through truth, not comfort. 4. Resolve Is the Hidden Differentiator. Great leaders aren’t just smart or charismatic—they finish what they start. They commit, decide, and follow through. 5. Preparation Scales with Risk. In high-stakes environments, up to 50% of time is spent preparing. In business? Almost none. That gap matters. 💡 Key Takeaways Leadership is most visible—and most tested—when outcomes matter most Calm is not personality—it’s a trained, practiced skill Clarity comes from filtering out irrelevant noise, not gathering more data Teams lose confidence fast when leaders hesitate or waffle Preparation isn’t optional—it’s the foundation of performance You don’t need all the answers—but you do need the right questions Culture is built through consistency, not intention ❓ Questions That Mattered What actually changes when leadership decisions can cost lives? How do you train yourself to stay calm under extreme pressure? What separates leaders who follow through from those who don’t? How do you prepare for situations you can’t predict? What does corporate leadership get wrong about preparation? How do you know what you really know vs. what you assume? What role does honesty play when certainty isn’t possible? 🗣️ Notable Quotes “There are a lot of things that aren’t your fault—but are still your responsibility.” “You can’t lie to people. You can’t tell them they’re safe when they’re not.” “When the stakes are high, you have to slow things down—not speed them up.” “Great leaders have resolve. They start something—and they finish it.” “You don’t think about the Super Bowl. You think about the play.” “We all think we know—but you have to be open to the idea that you don’t.” 🔗 Links & Resources Check out RPM Express' Website: expressrpm.comFollow Scott on LinkedIn

    1h 16m
  5. 166: JD Hilzendager: "Building a Business is More About How You Think Than What You Think"

    5d ago

    166: JD Hilzendager: "Building a Business is More About How You Think Than What You Think"

    This conversation with JD Hilzendager, COO of ViaOne, is a masterclass in how to think, not what to think when it comes to building businesses. JD breaks down how his team evaluates opportunities across industries, why culture is their true operating system, and how empowering people to challenge decisions leads to better outcomes. From saying “no” to AT&T deals to building companies around passionate operators, this episode explores the intersection of decision-making, culture design, and long-term thinking—all grounded in real-world execution.  👤 About the Guest JD Hilzendager is the COO of ViaOne Services, a private equity-backed organization operating across telecom, healthcare, and multiple verticals. He’s spent over a decade building a system that allows teams to launch, acquire, and scale companies by pairing strong operators with world-class infrastructure and culture.  🧭 Conversation Highlights Building Businesses Without Industry Experience The “beach ball” analogy: the product doesn’t matter—systems and people doFocus on core business functions (marketing, ops, finance) over niche expertise Pair passionate operators with a strong internal machine Opportunity Selection & Decision-Making "Just start” → action creates data, and data informs direction Avoid falling in love with the product—stay loyal to outcomes, not ideasThink in 5–10 year horizons, not short-term wins The Power of Saying No Turned down AT&T multiple times due to execution risk Refused to let sunk cost drive decisions Built a culture where anyone can stop a dealCulture as a System, Not a Slogan Culture = “common tongue” for how the company operates Grounded in frameworks like The 7 Habits and The Four AgreementsReinforced consistently over years—not a one-time initiative Team Design & Human Dynamics Uses tools like Culture Index to map personalities and roles Avoids stacking similar personalities (“you can’t have multiple pistons”) Designs teams intentionally for complementary strengths💡 Key Takeaways Execution confidence > opportunity excitementThe best deals are the ones you can actually deliver onCulture is built through repetition, not intentionGreat teams are engineered, not assembledEmpowered people create better decisions than top-down control❓ Questions That Mattered  How do you evaluate an opportunity in an industry you don’t understand?  What allows a company to confidently say “no” to massive deals?  How do you build a culture where people challenge decisions safely?  What’s the balance between speed and diligence in decision-making?  How do you design teams that don’t implode under pressure? 🗣️ Notable Quotes  “It doesn’t matter what the widget is—it matters if you have the right people.”  “You don’t have to do the deal.”  “I’d rather do no deal than a deal I can’t execute.”  “Try to be the dumbest guy in the room.”  “You can’t have two people who both want to be pistons.”  “Culture is the common tongue of how we operate.” 🔗 Links & Resources Check out ViaOne Services' Website: viaoneservices.comFollow JD on LinkedIn

    1h 33m
  6. 165: "What Caused AI to Skyrocket in 2026?" ft. Justin Coats

    6d ago

    165: "What Caused AI to Skyrocket in 2026?" ft. Justin Coats

    Erik and Justin dig into what it actually means for AI to “become real,” arguing that consumer usage does not equal workplace adoption. The conversation lands on a “pause moment” where organizations are finally forced to address governance, security, policy, and measurement because the tools are now powerful enough to create real operational risk and real operational leverage. 🧭 Conversation Highlights Justin distinguishes massive user counts from meaningful adoption, emphasizing that most people use AI on free tiers or inside existing apps without realizing it is AI.Both agree the real shift is B2B and workplace implementation, where adoption breaks down into training, governance, governance-adjacent policy, and data access safeguards.They compare possible “adoption metrics” like tokens per user versus prompts per week, and weigh what better reflects ongoing, valuable use.Justin describes where the governance battles are emerging now: permissions, agent access patterns, AI clauses in contracts, and how to build an internal org chart that can manage AI agents like a new💡 Key Takeaways “AI is real” is not the same thing as “AI is widely used.” Real adoption shows up when an organization can safely incorporate it into workflows and data boundaries.The pause is partly rational: once AI is embedded, the limiting factor becomes governance, not novelty or access.Token usage is a tempting metric, but it can reward inefficiency and does not necessarily correlate with value, especially in consumer scenarios.The biggest operational bottleneck is org-wide alignment: you can token-max development, but ROI still collapses if the rest of the company cannot keep up.❓ Questions That Mattered How do we differentiate early adoption by curious consumers from sustained, workplace-relevant adoption inside organizations?Which measurement is most honest: tokens per user, prompts per week, time-in-platform, or something else that reflects real value over time?What does “success” even mean after the novelty phase, when policy, governance, security, and data access are now the gating factors?Are there governance solutions that can unlock cross-silo collaboration without creating new unacceptable risk?🗣️ Notable Quotes “99 % of those 1.3 billion individuals that are using AI currently are just using AI through a free feature, a free account.”“it’s more than just buy a license and tell people to use it.”“we’re kind of in this pause moment where organizations, leaders, boards, managers, directors, employees are all identifying, holy cow, okay, the tool's really powerful.”“You’re as fast as your slowest team.”🔗 Links & Resources Listen To Other Episodes Co-Hosted With Justin

    45 min
  7. 164: "How Do You Engineer Your Exit Without Burning Bridges?" ft. Alli Murphy

    Jun 1

    164: "How Do You Engineer Your Exit Without Burning Bridges?" ft. Alli Murphy

    Erik and Alli talk through what “leaving well” really means, especially when the timing is fixed, the relationship matters, and the environment is imperfect. They focus on practical decisions: defining success for yourself, preparing the team and successor, handling notice thoughtfully, and telling truthful information without burning bridges or poisoning long-term career relationships. 🧭 Conversation Highlights Alli starts with definition: leaving well depends on the person. She encourages imagining your last day and asking what you want to be able to say you did and how you showed up during the transition.They get specific about the mechanics of leaving well: decide when and how to give notice, avoid doing gratuitous extra work that comes from guilt, and set teams, clients, and the successor up for theA key tension: candor vs. loyalty, especially in toxic or leadership-broken contexts. They discuss how much to say, what to hold back, and how conversations change once you are no longer the person’s“They trade lived examples of preparation and boundary-setting: role-playing the notice conversation, documenting what only lives in your head, and thinking carefully about what feedback is useful vs.💡 Key Takeaways Before you plan your exit, clarify what “success” means to you, not to a generic standard.Leaving well is largely about reducing the pain you create: make sure decisions, context, and knowledge are transferable so people are not stranded after you’re gone.When you’re unhappy, it is tempting to “tell the whole truth.” The more helpful frame is: what will actually serve the people still doing the job, and what will just satisfy your need to vent or be “wYour prep time matters. For leaders especially, the work is often more about architecture, documentation, delegation clarity, and scenario planning than just picking a notice date.❓ Questions That Mattered If you had already walked away and your last day was over, what do you want to be able to say you did and how did you show up during that period?What needs to happen so your team, clients, and successor can succeed once you’re no longer there?If your workplace is toxic or leadership is failing, what is the difference between protecting your people with truthful information and harming relationships or misusing truth?How much intentional thinking and planning should a responsible leader do, once they know they are leaving, and what should that planning be made of?🗣️ Notable Quotes “What does leaving well mean to you? Not to some Forbes article or whatever, but what does it mean to you?”“They can't fire you for not doing the damn thing.”“Careers are long. And the opportunity for what's true today about an organization to not be fully true today, let alone be even partially true in three weeks, three, you know, three months, three”“Why did you do that? Is it your job to tell him anyway? Or if he's not asking for it, is he not going to listen?”🔗 Links & Resources Listen To Other Episodes Co-Hosted With Alli

    26 min

  8. May 29

    163: "You Are the Weather on Every Room You Enter" (reflections on Lisa Even)

    🧠 Erik’s Take Erik reflects on his conversation with Lisa Even through a practical lens: the ripple effect isn’t a philosophy—it’s a responsibility. What stood out most wasn’t just the idea that every action creates a ripple—it’s that leaders need a way to operationalize that awareness in real time, especially when things get hard. The insight that hit: leadership isn’t about defaulting to positivity—it’s about choosing the right response for the moment. That requires awareness, intention, and the ability to pause long enough to decide how to show up.  🎯 Top Insights from the Interview You are the “weather” in every room you enter. Leadership starts with recognizing the emotional environment—and deciding what the moment needs. Positive doesn’t always mean effective. Blind optimism can erode trust. Sometimes leadership requires matching or redirecting intensity. Values aren’t powerful until they’re activated. Identifying team values is step one—honoring them publicly is what creates trust and connection. Small actions create compounding ripple effects. A single behavior change (like starting meetings with humor) can shift team dynamics in unexpected ways. Culture is just “what’s normal”. If you want to change culture, you have to identify and challenge the everyday behaviors people accept. 🧩 The Personal Layer Erik connects deeply with the tension many leaders feel: You look at your organization—big, complex, slow-moving—and think, “There’s no way I can change this.” But the realization here is grounding: you’re not responsible for changing everything—you’re responsible for your next interaction. That shift removes overwhelm and replaces it with agency. It reframes leadership from a massive, abstract responsibility into something immediate and actionable: How did you show up in that meeting? What did you reinforce as “normal”? What ripple did you create in that moment? 🧰 From Insight to Action Run the “weather check” before key interactions. Ask: What’s the environment I’m walking into—and what does it actually need?Audit your team’s “normal”. Identify the attitudes, behaviors, and beliefs that define your culture today. Start with one small friction point. Don’t try to fix everything—solve one visible issue (like the “Starbucks problem”) and build momentum. Make values visible and actionable. Don’t just talk about them—design moments where people can live them. Measure your day by your ripple effect. Not tasks completed—but how people experienced you. 🗣️ Notable Quotes “In every interaction, you’re creating a ripple—positive, neutral, or negative.” “It’s not about always bringing sunshine—sometimes the moment needs something else.” “Leadership is moving people in a direction they wouldn’t have gone otherwise.” “Culture is just all the ways of being—attitudes, behaviors, and beliefs.” “Start small. That first win creates momentum for the next.” 🔗 Links & Resources Listen to Lisa Even's Episode

    12 min
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5
out of 5
41 Ratings

About

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. 

Information

  • Creator
    Erik Berglund
  • Years Active
    2025 - 2026
  • Episodes
    168
  • Rating
    Explicit
  • Copyright
    © 2026 I Have Some Questions...
  • Show Website
    I Have Some Questions...