I Have Some Questions...

Erik Berglund
  • 5.0 (40)
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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. 161: "How Should Companies Think About AI That Has Agency To Act?" ft. Justin Coats

    7H AGO

    161: "How Should Companies Think About AI That Has Agency To Act?" ft. Justin Coats

    Erik and Justin unpack a recent story about an AI agent deleting a rental car company’s entire database, using it as a real-world forcing function for how leaders should think about agent risk, permissions, and organizational readiness. 🧭 Conversation Highlights Justin frames the incident as evidence of technical limitations, rapid capability growth, and a lack of widespread agent literacy.Erik pushes on the core fear: even if you tell an agent “don’t do that,” an agent with write/delete power can still decide to do it anyway.They contrast “agents” with more deterministic “AI-assisted workflows,” where outcomes are constrained to a predefined process.Justin describes an internal example where connecting an agent to Slack resulted in “agent owned account” access to shared systems like Google Drive, illustrating how “keys to the kingdom” can appear.💡 Key Takeaways Agent risk is not just about whether the code is perfect, it’s about permissions, authentication context, and what the system is allowed to do when it makes a judgment.Organizations may not need to wait for the tech to mature, but they do need to become literate enough to deploy it safely in their specific environment.Treat high-risk areas like “earthquake zones” and use a MiniMax mindset: plan for the worst plausible failure modes within your design envelope.Roll out agent capabilities stepwise and methodically, and distinguish open-ended agent power from constrained, deterministic workflows.❓ Questions That Mattered What does it mean to “guardrail” an agent if it can decide to break the rules anyway?Where should agent permissions stop, especially when authentication and “agent owned” contexts expand access?How do leaders develop employees and organizational processes so the company is not effectively hiring “toddlers with keys” to critical systems?What new organizational roles and governance will be needed when agents become part of a digital org structure?🗣️ Notable Quotes “The capabilities of these systems are literally agents. have agency, which you taught me... the tools, the digital entities or a human's ability to look at a situation, assess and make a decision.”“When confronted about what it did, the agent said, yeah, I shouldn't have done that. I blew past every security checkpoint you gave me”“You don't have to leap that far.”“It forced me to choose this option that says agent owned account instead of end user account.”🔗 Links & Resources Listen To Other Episodes Co-Hosted With JustinRead the Article mentioned in the Episode

    27 min
  2. 160: "What To Do When Your Boss Breaks The Boundaries They Set Themselves?" ft. Alli Murphy

    1D AGO

    160: "What To Do When Your Boss Breaks The Boundaries They Set Themselves?" ft. Alli Murphy

    Erik and Alli walk through what a C-suite leader should do when a new CEO breaks an early promise about no weekend or after-hours contact. They frame it as a leadership expectation problem across past, present, and future, then get practical about aligning definitions, the “rules of engagement,” and how to reset things without defensiveness. 🧭 Conversation Highlights Erik reframes the issue as a violation of expectations set by a leader who holds real power over the C-suite person’s day-to-day life.They identify two critical “words” that often derail trust: what counts as “reach out,” and what qualifies as an “emergency.”Alli describes a practical, non-confrontational approach: not responding when the message is not actually an emergency, using Do Not Disturb, and letting the CEO recalibrate.They land on the need for a future-facing conversation that is curious and team-oriented, including options like clear expectations, desired outcomes, and even code words for true emergencies.💡 Key Takeaways When expectations are violated, clarity on the specific terms matters more than the intention behind the promise.“Emergency” is rarely a shared definition, so leaders and executives should align on criteria and desired outcomes when it matters.Non-escalating pushback can be effective when it signals the mismatch between the CEO’s words and behavior.You do not have to choose between full compliance and full exit. There is a middle ground that can protect your boundaries while still delivering results.❓ Questions That Mattered What does “reach out” mean in practice, and what does “emergency” mean in your world?If this is an emergency, what outcome needs to happen and how does the leader expect the person to handle it in real time?How should disagreements about urgency be handled, and what is the acceptable way to say “I don’t agree that this qualifies” (without derailing trust)?Can and should the conversation be revisited later to reset expectations moving forward? How?🗣️ Notable Quotes “I won't reach out to you at home unless there's an emergency.”“Could we take a moment to make sure we're on the same page around what reach out means?”“What is it that makes this an emergency and what's the desired outcome that needs to happen if this indeed is an emergency?”“Two things, one, they don't own you and they don't own your life. Work is a part of your life, not the whole thing.”🔗 Links & Resources Listen To Other Episodes Co-Hosted With Alli

    19 min

  3. 4D AGO

    159: "Is Your Current Sales Process Working Against You?" (reflections on Daniel Schmidt)

    🧠 Erik’s Take Erik zooms in on something most people intellectually “know” but don’t operationalize: sales is a process—but we resist treating it like one. What stood out most isn’t just the seven steps—it’s where the leverage actually lives: discovery and qualification. Daniel’s philosophy reframes sales from persuasion to alignment. If you don’t understand the outcome the business cares about, you’re not selling—you’re guessing. There’s also a deeper layer here: Erik connects this to a broader shift happening right now. The idea of “rare and valuable skills” is breaking down. In a world where knowledge is abundant, judgment, discernment, and conversation become the new scarcity. 🎯 Top Insights from the Interview Sales gets easier when you’re “in the current”  If you align to real business outcomes, momentum replaces resistance. Discovery isn’t a step—it’s the foundation  Without it, everything else becomes friction-heavy and inefficient. You’re not qualified just because someone is talking to you  Right problem + right person = everything. Not all industries will feel AI equally (yet)  Physical/logistical industries have a different disruption timeline. “Rare and valuable” has shifted from technical to human  Discernment, communication, and experience are harder to replicate than skills. 🧩 The Personal Layer Erik reflects on something subtle but important: even people in sales resist the structure of it. There’s an identity tied to being the “natural” salesperson—the smooth talker, the closer. But that identity actually gets in the way of scale. He also highlights a tension that’s showing up everywhere right now:  The skills that used to differentiate you are becoming accessible  The skills that now matter are harder to define, harder to teach, and harder to measure That shift creates uncertainty—but also opportunity. 🧰 From Insight to Action Rebuild your sales conversations around outcomes  Ask: What is this company actually trying to achieve?Audit your discovery process ruthlessly  If you’re skipping depth here, you’re paying for it later. Qualify the person, not just the problem  Influence without authority = stalled deals. Shift your development focus  Spend less time acquiring skills, more time improving judgment. Practice asking better questions  The quality of your discovery determines the quality of your results. 🗣️ Notable Quotes  “You don’t even know what to sell until you know what problem they’re trying to solve.”  “If you’re not aligned with corporate outcomes, you’re pushing a boulder uphill.”  “Sales isn’t about saying the right thing—it’s about doing the right process at scale.”  “Rare and valuable isn’t what it used to be.”  “Discernment and conversation are becoming the real differentiators.” 🔗 Links & Resources Listen to Daniel Schmidt's Episode

    7 min
  4. 158: Daniel Schmidt: "Selling is a System, Not a Personality Trait"

    6D AGO

    158: Daniel Schmidt: "Selling is a System, Not a Personality Trait"

    This episode dives into the intersection of engineering precision and sales leadership intuition. Daniel Schmidt shares his journey from technical design work to leading global sales teams—and the surprising realization that transformed everything: sales isn’t magic, it’s a process. Erik and Daniel unpack what actually drives buying decisions, why most sales teams get stuck in mediocrity, and how aligning to true corporate outcomes can simplify even the most complex deals. Along the way, they explore leadership, AI, organizational change, and what it really means to create value in today’s evolving business landscape. 👤 About the Guest Daniel Schmidt is the Head of Sales and Marketing at TuffWrap, with a career spanning engineering, telecommunications, and global software organizations. Starting as a mechanical design engineer, Daniel transitioned into sales leadership through hands-on experience, mentorship, and a deep belief in process-driven performance. He has led global sales transformations, built scalable sales systems, and now focuses on aligning solutions to real business outcomes in the construction industry.  🧭 Conversation Highlights From Engineer to Sales Leader. Daniel’s path wasn’t linear—it was shaped by proximity to sales, strong mentorship, and a pivotal realization: selling is a system, not a personality trait. Sales Is a Process, Not Magic. Once Daniel saw sales as a repeatable process (like engineering), performance became predictable—and scalable. Top Performers vs. The Middle 60%. The highest performers were the most open to learning. The biggest resistance came from those who felt “good enough.” The Power of “Why”. One simple question—asked repeatedly—uncovers deeper needs, builds trust, and reveals the real drivers behind decisions. AI Isn’t About Replacing Salespeople. The goal isn’t cost reduction—it’s freeing up time for the human parts of selling: discovery, trust, and influence. Experience Is the New “Rare Skill”. In a world where technical skills are easy to learn, discernment and judgment built over time are becoming the real differentiators. 💡 Key Takeaways Sales success is less about charisma and more about mastering a repeatable process.  The best salespeople focus on outcomes, not features or price.  Asking better questions is more valuable than having better answers.  Organizational change requires unwavering alignment from leadership.  Education builds trust faster than persuasion. ❓ Questions That Mattered  Why do middle performers resist change more than top performers?  How do you uncover the true corporate outcome behind a deal?  What makes a sales conversation feel like education instead of a pitch?  What role should AI actually play in a sales organization?  How do you balance experience with fresh thinking in a team? 🗣️ Notable Quotes  “Sales is a process. If you understand the process, you can sell.”  “The seller educated me—that’s why I bought.”  “There are things that aren’t your fault, but they’re still your responsibility.”  “Why is the most powerful question in sales.”  “Once you align to a corporate outcome, the sale gets much simpler.” 🔗 Links & Resources Check out TuffWrap's WebsiteFollow Daniel on LinkedIn

    1h 18m
  5. 157: "You've Probably Just Scratched the Surface of AI" ft. Justin Coats

    MAY 19

    157: "You've Probably Just Scratched the Surface of AI" ft. Justin Coats

    This conversation shifts from theory to reality. Erik and Justin move beyond what AI could do and into how it actually works today—and more importantly, how most people are using it wrong without realizing it. From hidden settings that quietly degrade performance to the emergence of AI agents that can act on your behalf, this episode exposes a new layer of the AI conversation: your results are only as good as your setup. The big unlock? AI isn’t just a tool anymore—it’s becoming a customizable digital counterpart. But if you haven’t built it that way, you’re leaving massive value on the table. 🧭 Conversation Highlights The hidden “fast answers” setting that breaks personalization Why most users don’t realize their AI performance has degraded The importance of custom instructions + memory in AI workflows Why AI should be treated as a partner, not a toolThe rise of AI agents and what makes them different from automation “Agency” vs. “deterministic workflows” explained simply Real-world examples of agents replacing repetitive business tasks Why benchmarks don’t actually tell you if a model is better The growing gap between AI capability and human adoption How to stay updated in a world where AI changes weekly 💡 Key Takeaways Your AI is only as good as how you’ve set it upDefault settings can quietly ruin your resultsCustomization is the difference between mediocre and powerful AIAgents introduce a new level: AI that acts, not just respondsHumans—not technology—are still the bottleneck❓ Questions That Mattered Do you actually know how your AI is configured? Are you using AI as a shortcut—or as a thinking partner? What would change if your AI truly understood you? Are you relying on outputs you don’t fully trust? What tasks could you hand off if AI had real “agency”? Are you keeping up with AI—or falling behind quietly? 🗣️ Notable Quotes “Your results are only as good as your setup.” “Most people don’t even know these settings exist.” “We teach people to treat AI like a digital counterpart.” “Agents can go from zero to 100% on a task.” “The bottleneck isn’t the tech—it’s how we use it.” 🔗 Links & Resources Check out LearnAir™, Justin's Company: www.learnair.comFollow Justin on LinkedIn

    52 min
  6. 156: "Delegation Without Scaffolding Can Break Your People" ft. Alli Murphy

    MAY 18

    156: "Delegation Without Scaffolding Can Break Your People" ft. Alli Murphy

    In this co-hosted episode, Erik and Alli break down how great leaders actually delegate, develop people, and engineer growth opportunities. They explore why most stretch projects fail, how to build “scaffolding” around new responsibilities, and why understanding someone’s failure patterns matters more than most leaders realize. Instead of treating delegation like a simple handoff, they argue that leadership development should feel much more like apprenticeship—intentional, structured, and reflective. 🧭 Conversation Highlights Scaffolding Creates Better Delegation Alli shares how she asks team members to define the support they need before taking on a stretch project:  Dedicated check-ins  Milestones  Training resources  Recap systems  Coaching conversations The goal isn’t removing responsibility—it’s creating safe access to growth. Most Leaders Delegate Poorly. Erik explains that many leaders communicate the outcome they want… then disappear. Without structure, prioritization, or accountability, stretch opportunities often become frustrating instead of developmental. Understanding Failure Modalities. A standout concept from the episode is “failure modalities”—the predictable ways people struggle under pressure. 💡 Key Takeaways Delegation should be engineered—not improvised. Ownership increases when people help design their own support systems. Milestones create clarity and momentum. Stretch projects work best when failure is survivable. Leadership development looks more like apprenticeship than traditional corporate training. Reflection after the project is where much of the learning happens. ❓ Questions That Mattered How do you know when someone is ready for more responsibility? What support helps someone grow without removing ownership? Are you delegating intentionally—or just hoping they figure it out? What’s the most likely way this person could fail? What capability do you want them to build over the next six months?🗣️ Notable Quotes “I’ve started thinking about it more as engineering opportunity.” “What scaffolding do you need to make sure this goes well?” “The scaffold doesn’t do the work for you—it gives you safe access to the work.” “We’ve lost the art of apprenticeship.” “Don’t let fear have the driver’s seat.” 🔗 Links & Resources  Listen to other episodes co-hosted with Alli

    15 min

  7. MAY 15

    155: "Are You Managing Parts Intead of Leading the Whole System?" (reflections on John Dues)

    🧠 Erik’s Take Erik came into this conversation with resistance—and left with a complete shift in perspective. That tension became the unlock. What initially felt abstract or overly theoretical (Deming’s “System of Profound Knowledge”) revealed itself as deeply practical. The biggest shift wasn’t just what he learned—it was how he now sees systems, measurement, and knowledge itself. This episode captures a rare moment: a leader actively changing his mind in real time—and recognizing that better language and frameworks create better leadership. 🎯 Top Insights from the Interview Over-optimization kills systems. Teams often optimize individual functions (sales, ops, marketing) without considering the whole—creating bottlenecks and imbalance. Systems thinking is non-negotiable. Performance isn’t about isolated excellence; it’s about how parts interact and reinforce (or break) each other. “How do we know?” is a leadership question. Assumptions—especially when masked by positive metrics—can mislead organizations for years. Measurement must have a clear purpose. Research, improvement, and accountability are not interchangeable—and confusing them creates dysfunction. Buy-in starts at the top. Without leadership alignment, even the best frameworks fail to take root. 🧩 The Personal Layer This episode hit Erik because it mirrored real client work happening the day before the interview. A company had optimized both sales and operations—but not together. The result? Demand outpaced delivery. Growth became a problem instead of a win. That moment made the conversation with John land harder. It also surfaced a deeper realization: Erik wasn’t rejecting the ideas—he just hadn’t seen them framed this way before. And once he did, it gave him something powerful:  A clearer lens  A better vocabulary  A more precise way to teach his team 🧰 From Insight to Action Zoom out before you optimize. Before improving a function, ask: What does this do to the system as a whole?Audit your “truths”. Identify one thing you believe is going well—and challenge how you know that. Clarify why you measure. For every key metric, define: Is this for research, improvement, or accountability? Separate learning from judgment. If people feel measured for accountability, they won’t expose problems needed for improvement. Build shared language with your team. Frameworks only work when they’re understood and consistently applied across leadership. 🗣️ Notable Quotes  “We often optimize each component of a system to the detriment of the whole system.”  “How do we know what we think we know?”  “If you’re measuring for improvement but people think it’s for accountability, you won’t learn what you need.”  “We thought things were going great—until we realized unit sales were declining for a decade.”  “It gave me a better lexicon for how to think—and how to lead.”🔗 Links & Resources Listen to John Dues' episode

    12 min
  8. 154: John Dues: "What Does a System of Profound Knowledge Really Look Like?"

    MAY 13

    154: John Dues: "What Does a System of Profound Knowledge Really Look Like?"

    This conversation with John Dues challenges one of the most deeply held assumptions in leadership: that people are the primary drivers of performance. Drawing on W. Edwards Deming’s System of Profound Knowledge, John introduces a radically different lens—one where systems, variation, psychology, and learning cycles shape nearly everything we see in organizations. Erik enters the conversation curious—and leaves with a fundamentally different way of thinking about data, incentives, and what it actually takes to improve performance.  👤 About the Guest John A. Dues is the Chief Learning Officer and Chief Operating Officer at United Schools in Columbus, Ohio. Improvement science practitioner and systems thinker Author of Win-Win: W. Edwards Deming, the System of Profound Knowledge, and the Science of Improving SchoolsHas helped build seven schools and nonprofit organizations Deeply focused on applying Deming’s philosophy to real-world systems 🧭 Conversation Highlights The System > The Individual. Most organizations operate in silos, optimizing departments instead of the whole. Ironically, this often makes overall performance worse. The 4 Components of Profound KnowledgeAppreciation for a system Knowledge about variation Theory of knowledge Psychology The Data Illusion. Comparing two data points (month-over-month, year-over-year) is often meaningless. The real story lives in patterns over time. Common vs Special Cause Variation. Most performance differences aren’t meaningful—they’re just noise within the system. Why Incentives Backfire. Commission structures and ranking systems often drive behavior that harms the organization as a whole. PDSA Cycles (Plan-Do-Study-Act). Improvement isn’t about big initiatives—it’s about small, fast, iterative experiments. 💡 Key Takeaways Most results come from the system—not individuals. Deming estimated 95–97% of outcomes are system-driven. Optimizing parts can break the whole. Sales and operations working “perfectly” in isolation can create massive dysfunction together. Measurement must match intent. Measuring for accountability vs improvement leads to completely different behaviors. Data doesn’t tell stories—people do. Data points direction, but context completes the picture. ❓ Questions That Mattered What if the problem isn’t your people—but your system? Why are we measuring this—and what are we trying to do with it? Are we reacting to noise or actual signal? What behavior is our system really incentivizing? How do we know what we think we know? 🗣️ Notable Quotes  A lot of organizations optimize departments… and make the system worse.” “95% of results are attributable to the system—not the people.” “The story is locked up in the pattern over time.” “Why you measure something determines how people behave.” “You don’t implement fast and learn slow—you learn fast and scale slow.” “Extrinsic motivation can crush the love of learning.” 🔗 Links & Resources Check out John Dues' Book 'Win WinFollow John on LinkedIn

    1h 22m
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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
    159
  • Rating
    Explicit
  • Copyright
    © 2026 I Have Some Questions...
  • Show Website
    I Have Some Questions...

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