I Have Some Questions...

Erik Berglund
  • 5.0 (40)
  • MANAGEMENT

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. 149: "Vague Thinking Produces Weak Outputs, Specially with AI" ft. Justin Coats

    19H AGO

    149: "Vague Thinking Produces Weak Outputs, Specially with AI" ft. Justin Coats

    This episode marks the beginning of a new weekly series featuring Justin Coats—AI expert, co-founder of Learn Air, and now recurring co-host. Erik brings his biggest questions about AI in business, and Justin brings grounded, practical answers. The core tension? AI isn’t the limiting factor—humans are. Specifically, our lack of awareness around how we actually work. Together, Erik and Justin unpack why most businesses struggle to adopt AI, how vague thinking kills automation, and why leadership—not technology—is the true bottleneck. They explore the uncomfortable truth: you can’t automate what you don’t understand… and most people don’t understand their own workflows. 👤 About the Guest Justin Coats is the Chief Visionary Officer and Co-Founder of LearnAir, an AI literacy and integration company and official OpenAI training partner. He specializes in helping organizations safely understand, adopt, and implement large language models—bridging the gap between cutting-edge technology and real-world business application.  🧭 Conversation Highlights Why AI adoption is failing—and it’s not because of the tech The “lack of a mirror” problem in modern work How vague language breaks AI performance Why most people can’t explain how they do their job The hidden 30% efficiency gain from simply thinking about your process The role of leadership in driving (or killing) AI adoption How early adopters are creating new organizational bottlenecks The shift from tasks → purpose in the age of AI What happens when humans move faster than the system around them 💡 Key Takeaways You can’t automate what you don’t understand — Most workflows are invisible even to the people doing them AI rewards specificity — Vague thinking produces weak outputs Efficiency starts with awareness — Many gains happen before AI is even used Leadership determines adoption — Mandates fail; modeled behavior works AI creates uneven acceleration — Some teams move 4x faster, exposing bottlenecks elsewhere ❓ Questions That Mattered How do you describe your job at a level AI can actually execute? What steps are hidden inside the “simple” tasks you do every day? Are you resisting AI because of time… or because of ego? What inefficiencies are you unknowingly covering with skill? Is your leadership team actually using AI—or just telling others to? What would happen if your workflow was fully visible? Are you solving for tasks… or the purpose behind them? 🗣️ Notable Quotes “You can’t automate what you don’t already know how to do.” “We truly don’t know how we do our work—we just do it.” “Spend 95% of your time thinking… AI will handle the rest in microseconds.” “The human is the limiting factor.” “Leadership isn’t saying ‘go use AI’—it’s showing how you use it.” “We weren’t created to work in a digital universe.” 🔗 Links & Resources Check out LearnAir, Justin's Company: www.learnair.comFollow Justin on LinkedIn

    38 min
  2. 148: "What Do You Do When Your Boss Isn’t Doing Their Job—But You Could?" ft. Alli Murphy

    1D AGO

    148: "What Do You Do When Your Boss Isn’t Doing Their Job—But You Could?" ft. Alli Murphy

    In this conversation, Erik and Alli unpack a deceptively simple leadership dilemma: Should you step in and do the work to prove you're ready for the next level—or hold back to avoid being taken advantage of? What unfolds is a nuanced exploration of responsibility, visibility, emotional intelligence, and long-term career alignment. They challenge the idea that leadership is about titles—and instead argue it’s about how you respond when things fall apart around you. 🧭 Conversation Highlights Opportunity hides in dysfunction. When responsibility is dropped, that’s not just a problem—it’s a signal. Stepping in can accelerate your growth and clarify whether the role (or company) is worth it. Leadership isn’t just doing—it’s thinking. Proving readiness doesn’t always mean executing tasks. Sometimes it’s about showing strategic awareness, surfacing risks, and proposing solutions. Visibility matters (but so does tact). Doing the work without making it visible is a risk. But visibility doesn’t mean throwing someone under the bus—it’s about communicating impact intelligently. Responsibility ≠ execution. Taking ownership doesn’t always mean doing everything yourself. It can mean ensuring the outcome happens—through influence, planning, or escalation. Your environment will eventually reveal itself. If your effort consistently goes unrecognized, that’s not just frustrating—it’s data. And the faster you see it, the faster you can make a better decision. 💡 Key Takeaways Step into responsibility—but be strategic about how. Doing everything blindly can backfire. Pair action with visibility and intentional communication. Think like the next-level leader before you become one. Demonstrating judgment, prioritization, and foresight is often more powerful than just grinding through tasks. Control your emotional reactions in the moment. Frustration is valid—but your response should come from your best self, not your reactive self. Use frustration as information, not fuel. Emotional spikes are signals. They shouldn’t dictate your behavior—but they can guide your decisions. If you’re not valued, don’t wait forever to realize it. Sometimes the real win isn’t the promotion—it’s the clarity that you’re in the wrong place. ❓ Questions That Mattered  What does it actually prove if you don’t do the work that needs to be done?  How can you demonstrate readiness without being exploited?  What’s the difference between taking responsibility and doing everything yourself?  How would your “best self” respond in this moment?  What if the real opportunity is realizing this isn’t the right environment? 🗣️ Notable Quotes “Opportunity lurks where responsibility has been abdicated.” “Taking responsibility doesn’t mean you have to do the thing—it means you make sure it gets done.” “Would you rather know in 18 months—or 10 years—that you’re not valued?” “How would the version of you you’re trying to become handle this?” “Even if you get taken advantage of… that’s a hell of a piece of information to have.” 🔗 Links & Resources Listen to other episodes co-hosted with Alli

    14 min

  3. 4D AGO

    147: Are Misaligned Incentives Shaping the Outcomes We Complain About? (reflections on Addison Hosner)

    🧠 Erik’s Take In this reflection episode, Erik steps back from his conversation with legal commentator and Young Voices contributor Addison Hosner to unpack the deeper themes that emerged. What stood out most wasn’t just the legal issues themselves—it was the systems behind them. From billable hours in the legal profession to qualified immunity and the incentives shaping journalism, Erik explores how misaligned incentives quietly shape outcomes across entire industries. His biggest realization? Many of the frustrations people feel about institutions—law, policing, media, even public debate—often stem from systems that reward the wrong behaviors. When the incentives are misaligned, even well-intentioned people can produce broken outcomes. For Erik, the conversation also reinforced a belief he returns to often: communication matters deeply in shaping the future. The ability to discuss complex issues without falling into sensationalism or partisan noise may be one of the most important skills the next generation develops. 🎯 Top Insights from the Interview 1. The legal profession runs on incentives that can create burnout. Lawyers often operate under billable-hour models that require accounting for time in six-minute increments and hitting around 2,000 billable hours per year, which can push workloads into the 70–80 hour range. 2. When incentives are misaligned, efficiency isn’t rewarded. If legal firms profit from hours billed rather than outcomes delivered, the system discourages speed and efficiency—creating a structure that may not serve clients well. 3. Qualified immunity raises difficult accountability questions. The doctrine protects officers from liability if actions occur while performing their duties, even when harm occurs. The debate centers on how to balance accountability with the realities of law enforcement. 4. Insurance-based accountability might be a potential solution. Addison suggested a model similar to malpractice insurance, where officers carry liability coverage. This could create financial accountability and better visibility into patterns of misconduct. 5. Sensationalism is becoming a default communication style. Young writers entering policy discussions often assume partisan or inflammatory framing is the only way to gain attention—something organizations like Young Voices actively work to counter. 🧩 The Personal Layer Erik’s reflection reveals a deeper curiosity about how systems shape behavior. Rather than framing issues as “good people vs. bad people,” he’s drawn to a more structural lens: What incentives are driving the behavior?What system design is reinforcing those outcomes?And how could the structure be improved?That mindset also connects to his broader leadership philosophy. Whether in law, media, or business, Erik consistently comes back to a similar theme: The structure of a system determines the behavior inside it. When incentives align with the right outcomes, progress becomes easier. When they don’t, even talented, well-meaning people struggle. 🧰 From Insight to Action Here are a few leadership takeaways Erik pulls from this conversation: 1. Look beyond individuals to the incentives shaping behavior. If something feels consistently broken in an organization, the problem may be structural rather than personal. 2. Evaluate how success is measured. Metrics drive behavior. If the metric rewards the wrong thing, expect the wrong outcomes. 3. Communicate complex ideas responsibly. Influence grows when ideas are presented clearly and thoughtfully—not through sensationalism. 4. Encourage thoughtful discourse over ideological extremes. Constructive conversation requires nuance, something that’s increasingly rare in modern medi

    13 min
  4. 146: Addison Hosner: "Can the Legal System Be Both Profitable and Ethical?"

    6D AGO

    146: Addison Hosner: "Can the Legal System Be Both Profitable and Ethical?"

    In this episode, Erik sits down with attorney and nonprofit executive Addison Hosner to unpack the realities behind the legal profession — from burnout in family law to the structural incentives that shape how justice is practiced. Addison shares what it was like running a solo law firm with a massive caseload, why he ultimately left litigation, and what the legal system often gets wrong about efficiency, incentives, and human impact. The conversation moves beyond career stories into deeper questions about legal ethics, qualified immunity, policing accountability, and how structural incentives shape behavior inside complex systems. 👤 About the Guest Addison Hosner is a lawyer and former family law practitioner who founded and ran Hosner Law Group before transitioning into nonprofit leadership. He now serves as Chief Operating Officer at Young Voices, a nonprofit organization focused on promoting ideas around free markets, civil liberties, and public policy. His work and writing frequently explore topics like criminal justice reform, qualified immunity, and the structural incentives that shape the legal profession. 🧭 Conversation Highlights Leaving Litigation and the Weight of Family Law Addison managed 70–100 active cases at a time as a solo attorney, many involving divorce, custody, and domestic conflict.Carrying the emotional weight of those disputes began to affect his health, sleep, and personal relationships.The realization came when he asked himself one question: Could I do this for another 35–40 years?The Hidden Stress of the Legal Profession Legal work is far less courtroom drama than TV portrays — it’s mostly paperwork and constant client pressure.Lawyers track their time in six-minute increments, creating constant pressure to justify every moment of the day.This environment often conditions attorneys to believe that any downtime equals failure.The Billable Hour Problem Law firms are financially incentivized to prolong disputes rather than resolve them quickly.Addison shared an experience where he was reprimanded for settling a case too quickly because it reduced billable hours.This misalignment of incentives is one of the profession’s most persistent structural issues.💡Key Takeaways Incentives shape behavior more than intentions. Even well-meaning professionals will follow systems that reward certain outcomes.The legal system often rewards conflict rather than resolution, especially under billable-hour models.Burnout in law isn’t just workload — it’s emotional exposure to human conflict.Student debt plays a major role in shaping legal career paths and ethical tradeoffs.❓ Questions That Mattered What happens when a system incentivizes the opposite of what it claims to value?Can the legal profession move away from billable hours without collapsing its business model?How should society balance police accountability with the realities of dangerous frontline work?What would it take to make the legal profession healthier for the people inside it?🗣️ Notable Quotes “My worst day as COO is still better than my best day as a practicing attorney.”“Each case isn’t just work — it’s someone’s life that you’re holding in your hands.”“Sometimes the system itself is what pushes good people into bad incentives.”🔗 Links & Resources Check out Young Voices' WebsiteFollow Addison on LinkedIn

    46 min
  5. 145: "What Would You Want From Your Manager If You Survived a Layoff?" ft. Alli Murphy

    APR 27

    145: "What Would You Want From Your Manager If You Survived a Layoff?" ft. Alli Murphy

    Mass layoffs, uncertainty, and pressure to perform—this conversation tackles one of the hardest realities leaders face: guiding a team through chaos when you don’t have answers yourself.  Erik and Alli unpack what leadership actually looks like in these moments—less about strategy, more about humanity. From one-on-one conversations to sitting in discomfort, this episode challenges the instinct to “fix” and instead reframes leadership as presence, trust, and intentional communication.  🧭 Conversation Highlights Lead One Human at a Time  In moments of disruption, mass communication isn’t enough. Real leadership happens in one-on-one conversations where people feel seen and heard. Resist the Urge to Solve Too Fast  The instinct to fix everything immediately can backfire. Leaders need to create space before jumping into solutions. “Sit in the Suck” Is a Strategy  Avoiding discomfort delays progress. Acknowledging frustration, anger, and uncertainty is a necessary step—not a weakness. Different People, Different Reactions  Not everyone experiences layoffs the same way—some feel fear, others relief, others guilt. Leadership requires listening, not projecting. Vulnerability Builds Trust—If Done Right  Leaders don’t need all the answers, but they do need honesty. Sharing uncertainty (without spiraling) strengthens credibility. 💡 Key Takeaways Connection beats communication. People don’t need perfect answers—they need to feel understood. Listening is the leadership move. Especially when you don’t have control, your presence matters more than your solutions. Emotions aren’t a distraction—they’re the work. Ignoring them creates bigger problems later. Preparation isn’t just tactical—it’s relational. Trust built before a crisis determines how well you lead through it. Great leaders run toward the fire. Avoidance erodes trust. Presence builds it. ❓ Questions That Mattered What would you want from your manager if you were still there after layoffs? How do you lead when you don’t have answers? Are you listening to your team—or projecting your own fears onto them? What happens when empathy turns into avoidance? How do you prepare for a crisis you can’t predict? What impact is your team actually making—and who knows about it? If cuts happened tomorrow, who would be most at risk—and why? Where have you avoided giving feedback that could have changed someone’s trajectory? 🗣️ Notable Quotes “You don’t have the answers—and that might be the thing that earns you the most trust.” “When something catastrophic happens, it requires a one-on-one human touch.” “Sit in the suck before you try to solve it.” “Just because you feel something doesn’t mean your team feels the same way.” “The best leaders run into the fire—and treat the humans in it with them appropriately.” 🔗 Links & Resources Listen to other episodes co-hosted with Alli

    19 min

  6. APR 24

    144: "Are We Going About Measuring Success All Wrong?" (reflections on Patrick Guerette)

    After his conversation with Patrick Guerette, Erik reflects on a simple but uncomfortable idea: we may be measuring success completely wrong. In sports, success is usually measured by medals, championships, and rankings. But those metrics only capture the athletes who survived the system—not the many who may have had potential but never made it through. The same thing happens in leadership. Organizations celebrate the high performers who emerge at the top of the pyramid, but rarely ask what happened to everyone else along the way. Were they developed? Or did the system quietly eliminate them? This episode is Erik thinking out loud about what happens when leaders stop focusing only on the winners and start paying attention to the system that produces them. 🎯 Top Insights from the Interview The medal count hides the real story. Olympic medals only show the winners, but they don’t reveal how many athletes were pushed out of the system before reaching their potential.The pyramid principle applies everywhere. Whether in sports or organizations, the height of elite performance depends on how broad the base of development is.Systems shape outcomes more than individuals do. Talent matters, but the environment surrounding people determines whether that talent grows or disappears.Early pressure can destroy long-term potential. Systems that chase immediate results often eliminate athletes—or employees—before they have time to develop.Development should be the primary goal. When a system focuses on development first, performance tends to follow naturally. 🧩 The Personal Layer For Erik, this conversation triggered a deeper reflection about leadership. It’s easy to celebrate the top performers—the people who hit their numbers, get promoted, or win awards. But leaders rarely ask the harder question: How many capable people never reached their potential because of the system we put them in? In sports, that might mean young athletes who burned out or were cut too early. In organizations, it might mean talented employees who disengaged because they were never coached, challenged, or developed. The uncomfortable truth is that leaders design the environment that determines how people grow. When a system is designed well, potential expands. When it isn’t, talent quietly disappears. 🧰 From Insight to Action Evaluate the base of your pyramid. How many people in your organization are truly being developed—not just evaluated?Look beyond the winners. The real test of a system isn’t how many stars it produces, but how many people improve.Design for development, not just performance. Create systems that give people time and opportunity to grow.Pay attention to who disappears. Sometimes the most important data point is the talent that quietly leaves.Ask better questions about success. Instead of asking “Who won?”, start asking “How many people got better?” 🗣️ Notable Quotes “The height of the pyramid is a function of how broad the base is.” “We celebrate the winners, but we rarely ask what happened to everyone else.” “Great systems don’t just produce champions—they develop people.” 🔗 Links & Resources Listen to Patrick Guerette's Episode

    9 min
  7. 143: Patrick Guerette: "Are We Measuring Success in Athletes the Wrong Way?"

    APR 22

    143: Patrick Guerette: "Are We Measuring Success in Athletes the Wrong Way?"

    In this conversation, Erik sits down with Patrick Guerette to explore what sports systems can teach us about leadership, development, and long-term performance. Patrick shares insights from his experience in sport and athlete development, unpacking how different countries design systems that either nurture or destroy potential. The conversation moves beyond medal counts and highlights a deeper question: Are our systems actually developing people—or just extracting short-term results from a few survivors? 👤 About the Guest Patrick Guerette is the COO of Alfond Youth & Community Center and works at the intersection of sport, development, and performance systems. His work explores how athletes develop over time and how national sport systems either cultivate or hinder long-term potential. Patrick is particularly interested in models that prioritize broad participation, long-term development, and sustainable performance, including internationally recognized systems like Norway’s approach to sport development. 🧭 Conversation Highlights Why medal counts don’t tell the full story. Many countries evaluate success based on Olympic medals, but that metric ignores the athletes who never reach their potential because the system filtered them out too early.The Norway model of athlete development. Norway’s sports philosophy focuses on building a broad base of participation and development rather than early specialization or intense pressure. The result: consistent high-level success from a small population.The pyramid principle. Elite performance sits at the top of a pyramid. If the base of participation and development is narrow, the pyramid can never grow very tall.The hidden cost of performance-driven systems. Systems that chase early results often burn out athletes and eliminate potential talent before it has time to develop.Why systems—not just individuals—determine success. Talent matters, but the structure surrounding athletes (or employees) determines how much of that talent actually reaches its potential.💡 Key Takeaways A strong system develops many people, not just a few stars. When development is the priority, excellence becomes a natural outcome.Short-term success can hide long-term failure. Winning medals—or hitting quarterly targets—doesn’t necessarily mean the system is working.Participation fuels performance. The broader the base of engagement, the higher the ceiling for elite outcomes.Great systems protect potential. They create environments where individuals can develop over time rather than being eliminated prematurely.Leadership is about designing environments. Whether in sports or business, the structure leaders create determines how people grow.❓ Questions That Mattered What if we measured success not by winners—but by how many people reached their potential?Are our development systems designed to build people… or just produce results?What happens to the talent that gets filtered out too early?How wide is the base of the pyramid in your organization?Are we building systems that sustain excellence—or ones that accidentally destroy it?🗣️ Notable Quotes “The height of the pyramid is a function of how broad the base is.” “Athletes emerge out of our system that are very talented—but what about the ones left in the wake?” “If the base is narrow, it will never get very high.” 🔗 Links & Resources Check out Alfond Youth & Community Center's WebsiteFollow Patrick Guerette on LinkedIn

    1h 24m
  8. 142: "What Happens When Your Team Suddenly Doubles in Size?" ft. Alli Murphy

    APR 20

    142: "What Happens When Your Team Suddenly Doubles in Size?" ft. Alli Murphy

    The rise of the “mega manager” is real—and it’s breaking traditional leadership models. In this conversation, Erik and Alli unpack what happens when managers go from leading 6–8 people to 12–16 (or more), why it’s happening, and how leaders can adapt. From rethinking one-on-ones to abandoning the “subject matter expert” trap, this episode explores the tension between what leadership should look like—and the messy reality leaders are navigating today. It’s part strategy, part mindset shift, and part honest reckoning with a system that’s quietly forcing leaders to evolve.  🧭 Conversation Highlights The Rise of the Mega Manager. Average team sizes have jumped ~50% in a decade—creating unsustainable expectations and forcing leaders to rethink everything. Why This Is Happening (It’s Not Just One Thing). Layoffs, remote work, poor leadership development, and over-reliance on SaaS tools have all contributed to fewer managers overseeing more people. The “Subject Matter Expert Trap”. Most leaders were promoted for doing the work—then stay stuck doing it, instead of actually leading people. The Steelman Argument for Bigger Teams. What if oversized teams force leaders to finally develop real leadership skills by removing the option to stay in the weeds? Leadership Systems That Actually Scale. Rotating team leadership, restructured one-on-ones, and async communication become essential—not optional. 💡 Key Takeaways You can’t scale leadership the same way you scale teams. More people doesn’t just mean more effort—it demands a fundamentally different approach. Time pressure exposes bad leadership habits. When your team grows, you lose the ability to hide in meetings, problem-solving, and expertise. Leadership is not knowing more—it’s developing others. The faster you let go of being the expert, the faster your team grows. You must redesign your systems, not just work harder. One-on-ones, meetings, and communication need to evolve with your team size. If you don’t advocate for change, you’ll own the failure. Leaders who don’t “plant the flag” early risk being held accountable for broken systems later. ❓ Questions That Mattered What’s actually driving the explosion of team sizes? At what point does a team become too big to lead effectively? What do you stop doing when you no longer have time for everything? How do you maintain development and connection at scale? When should a leader push back—and how? 🗣️ Notable Quotes “We don’t know how to develop leaders.” “You have no choice but to get out of the minutiae.” “You can’t bend the laws of physics and time.” “You’re doing the job of two people—so negotiate like it.” “You owe it to your future self to plant the flag.” 🔗 Links & Resources Listen to other episodes co-hosted with Alli

    19 min
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5
out of 5
40 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
    147
  • Rating
    Explicit
  • Copyright
    © 2026 I Have Some Questions...
  • Show Website
    I Have Some Questions...

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