I Have Some Questions...

Erik Berglund
  • 5.0 (38)
  • MANAGEMENT

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.

  1. 1D AGO

    111: "Are You Taking Your Infrastructure For Granted?" (lessons from Victor Almeida)

    Send us a text 🧠 Erik’s Take In this follow-up to his interview with Victor Almeida, Erik zooms out to reflect on what building a digital business really looks like in Latin America—and what North American entrepreneurs often take for granted. From basic infrastructure challenges to deep-rooted cultural wisdom, this episode is a powerful reminder that hardship often breeds the greatest human capital. And behind Victor’s startup dream is a deeper calling: to create opportunity where access has long been limited. 🎯 Top Insights from the Interview Family wisdom is foundational: Victor’s uncle and mother passed down principles that shaped his view of life, work, and risk.Resilience is forged in scarcity: Political instability and economic fragility have created people who are hyper-adaptable, cross-functional, and entrepreneurial by necessity.Digital access is not universal: Things like Google Maps, reviews, or reliable Wi-Fi are luxuries in many parts of the world—and that has ripple effects on what businesses can be built.Latin America’s human capital is underutilized: Erik highlights the scrappy, multi-skilled digital talent he’s worked with—and how that edge is forged in environments of uncertainty.Building a platform is harder when no one’s online: Victor’s challenge isn’t technical—it’s cultural and infrastructural.🧩 The Personal Layer Erik’s reflection is rooted in humility—he acknowledges how much he’s taken for granted living and building in the U.S. The conversation made him reevaluate the assumptions baked into the startup ecosystem: bandwidth, funding, listing infrastructure, even social trust around digital tools. He draws a powerful connection between Victor’s “desert power” analogy (from Dune) and the strength of communities forged through challenge. Erik also shares a deep appreciation for the emotional backbone of Victor’s journey: his mom’s push to “go outside and take risks,” and his uncle’s mantra to “plant a tree, write a book, build a business, and have a kid.” 🧰 From Insight to Action Ask yourself: What am I taking for granted in my business infrastructure?Seek out and collaborate with underrepresented digital talent—they often bring unmatched versatility.Reflect on the wisdom that shaped your worldview—what life scripts are you still following?Remember that policy environments matter—support leaders and founders working to shift systemic barriers.Lead with humility when building in or with other cultures. Ask more, assume less.🗣️ Notable Quotes “Plant a tree. Write a book. Build a business. Have a kid. That’s a life well lived.” — Erik, reflecting on Victor’s uncle’s wisdom “Scarcity breeds resilience—and that’s what creates the best human capital.” — Erik Berglund “Most of us assume access to digital tools is universal. It’s not. That assumption is a privilege.” — Erik Berglund “Victor’s not just building a startup—he’s building infrastructure where none exists.” — Erik Berglund “You only need one win—and your life changes completely.” — Victor Almeida 🔗 Links & Resources Listen to Victor Almeida's Episode

    12 min
  2. 110: "Is Survival Mode Your Greatest Startup Asset?" ft. Victor Almeida

    3D AGO

    110: "Is Survival Mode Your Greatest Startup Asset?" ft. Victor Almeida

    Send us a text Victor Almeida joins Erik from Ecuador to talk about what it really takes to build and scale a digital company in Latin America. From leading operations at Promotick Mexico to bootstrapping a startup from scratch, Victor offers raw insight into navigating thin margins, unstable infrastructure, and investor skepticism. But what shines brightest is his human-first leadership, scrappy mindset, and a deep belief that meaningful change starts with people who are willing to take a risk—even when the odds aren't in their favor. 👤 About the Guest Victor Almeida is the COO of Promotick Mexico and a rising voice in Latin America’s digital transformation space. Born and raised in Ecuador, he has led commercial and operational teams across multiple countries while co-founding FIRU, a platform designed to bridge the gap between local providers and digital access. Victor brings a rare mix of grassroots experience, startup vision, and global perspective to his work—plus a deep love for family, wine, and quotes from Dune. 🧭 Conversation Highlights Victor’s path from politics major to COO in a tech companyThe leadership shock of moving from sales to operations — and learning to say noThe origin and purpose behind Victor’s startup, Fidu, and the digital gap it aims to solveWhy building a digital business in Ecuador means doing more with less—less internet access, less funding, less infrastructureWhat American tech builders take for granted—and what they can learn from Latin American foundersWisdom from his mom, his uncle, and a monk in Shanghai (yes, really)The power of human-first leadership in unstable business environmentsWhy the path to change isn’t politics—it’s entrepreneurship💡 Key Takeaways Adaptability is the baseline: In regions of constant uncertainty, survival breeds resilience—and surprising innovation.Leadership is personal: For Victor, being a good boss means being a good human first. That builds trust and high-performing teams.You don't need a title to make change: Impact doesn’t require politics—it starts with creating value and showing up for people.Digital infrastructure can’t be assumed: Tools we take for granted in North America (like Google Maps or e-wallets) are missing in many regions.Risk is a feature, not a bug: Victor’s whole story is proof that courage matters more than credentials when systems aren’t built for you.❓ Questions That Mattered What does leadership look like in environments of instability?How do you scale a digital company where digital adoption is still limited?What’s the biggest disconnect between North American startup culture and the rest of the world?Why are margins so much thinner—and what does that teach you?How do you raise money for a startup when investors expect you to quit your job first?🗣️ Notable Quotes “If you don’t take the risk, you don’t win. And if you lose, you learn.” — Victor’s mom “Digital transformation is about people. My job is to be human first, work after.” — Victor Almeida “I used to care about my commission. Now I care if the operation is profitable.” — Victor Almeida 🔗 Links & Resources Promotick MexicoBook: Quiero Ser Presidente ("I Want to Be President") by Victor AlmeidaConnect on Instagram: @vican2294Victor's LinkedIn

    50 min
  3. 109: "How Playing the 'Chief Everything Officer' Role Leads to Burnout" ft. Alli Murphy

    5D AGO

    109: "How Playing the 'Chief Everything Officer' Role Leads to Burnout" ft. Alli Murphy

    Send us a text It’s only mid-January, and Erik and Alli are already fielding DMs from high-achievers who are feeling… fried. Instead of the usual New Year buzz, there’s burnout, exhaustion, and the quiet voice saying, “I’m already over it.” In this episode, the two explore why this is happening, especially for those in leadership or “Chief Everything Officer” roles—and what to do when your drive turns into depletion. They talk about internalized rules, shifting incentives, false reward systems, and the uncomfortable but liberating process of rewriting the script. ❓ The Big Question If you’re already burnt out… what now? And how do you make space to actually recover? 💡 Key Takeaways Burnout is often driven by invisible rules we’ve internalized. If you don’t surface them, you can’t rewrite them.Your incentive structure may have expired. What used to motivate you might not anymore—and that’s not failure, it’s evolution.People are rewarded for behaviors that lead to burnout. From fast email responses to picking up the team’s slack, subtle “praise” reinforces overextension.Burnout doesn’t always mean you need a vacation. It may mean you need to realign with what actually matters.Stillness is the medicine—but it requires courage. Slowing down to assess the problem feels costly, but it’s the only way through.🧠 Concepts, Curves, and Frameworks The Chief Everything Officer Trap – When people (especially women) take on every role out of habit, fear, or conditioning.Internal Operating Rules Audit – A practice to surface the beliefs driving your overextension (e.g., “I must always be available”).The Reward Shift – What used to excite you—money, praise, titles—may not anymore, and that disconnect creates exhaustion.Short-Term Pain vs. Long-Term Burnout – A moment of pause and reflection now may save months of depletion later.🔁 Real-Life Reflections Alli shared her own experience with burnout and how writing out her “internal rules” (and identifying where they came from) helped her make lasting change.Erik reflected on how burnout often stems from disconnection—either from the purpose behind the work or from a reward structure that no longer fits.They both emphasized how often burnout is not about workload alone—but about meaning, identity, and the patterns we’re unconsciously following.🧰 Put This Into Practice Audit your “unspoken rules.” Write down the expectations you feel pressure to live by—then ask, “Where did this come from?”Name your old rewards. What used to feel good that no longer does? What would be more meaningful now?Ask yourself: “What’s the alternative?” If stillness feels hard, ask what staying stuck is costing you.Treat burnout as data, not a defect. It’s a sign that something’s misaligned—not that you’ve failed.Add 5% more joy or life outside of work. Even small shifts can create the momentum to reset.🗣️ Favorite Quotes “Burnout is not your fault. You might be unknowingly contributing to it—but those rules? You learned them from someone else.” – Alli “You can't remind someone why something matters. They have to reconnect with it themselves.” – Erik “The rewards are no longer that rewarding—and that’s the real problem.” – Erik “You’ve been praised for behaviors that led to burnout. That conditioning is real.” – Alli “There is a solution. And you don’t have to burn it all down to find it.” – Erik 🔗 Links & Resources Listen to other episodes co-hosted with Alli

    19 min

  4. JAN 30

    108: Are You Solving the Wrong Problem Really Well?" (lessons from Bruce Vojak)

    Send us a text 🧠 Erik’s Take Erik reflects on his wide-ranging conversation with innovation expert Bruce Vojak and explores how innovation really works inside mature companies. While Erik lives and works in the world of startups and early-stage change, Bruce offered a deeply human, grounded perspective on how breakthrough ideas still emerge in the “slow lanes” of legacy organizations. Bruce’s insights revealed something profound: the best innovations don’t always begin with new technology — they begin with better questions. And specifically, with people willing to ask: Are we solving the right problem? 🎯 Top Insights from the Interview Innovation starts with real curiosity: Bruce’s advice? Find a problem you’re actually interested in — and know a little about — and follow it.Innovator Exemplars are rare but essential: These are the people who stay obsessed with solving the real customer problem — not just executing their pet solution.Companies need to match internal resistance to market resistance: Innovation shouldn’t be harder internally than it is in the real world — but it shouldn’t be easier either.The best processes do more than guide: They instruct the newbie, remind the expert, and discipline the executive to decide.Innovation is human work: Process helps, but it never replaces the people who notice, reframe, and act.🧩 The Personal Layer Erik draws parallels from his own leadership journey — especially the tension between having a great idea and actually getting an organization to adopt it. He’s lived both sides: cultures that champion every idea (even the wrong ones), and cultures that make every new idea feel like heresy. The sweet spot, he argues, is a culture that tests ideas the way the market would — no more, no less. He also highlights the subtle trap of ego in innovation: when we fall in love with our solution more than the real problem, we lose the thread. Bruce’s insistence on humility — on “submitting to reality” — resonated deeply. 🧰 From Insight to Action Leaders: Audit your innovation climate. Do new ideas die on the vine — or do they rise too fast without testing? Neither extreme works.Spot the innovators in your org: Do you have an exemplar quietly solving real problems in unconventional ways? Make room for them.Evaluate your processes: Are they guiding the novice, nudging the expert, and triggering real decisions? Or just adding drag?Start with the right question: Reframe the problem — don’t just build a better widget.Protect the spark, but invite others in: Innovation requires collaboration. Hoarding the idea kills its potential.🗣️ Notable Quotes “The best innovators don’t fall in love with their idea — they stay obsessed with solving the customer’s problem.” — Erik Berglund “Innovation should be no more or less difficult than the market itself.” — Bruce Vojak “The best process does three things: it instructs the newbie, reminds the expert, and disciplines the executive.” — Bruce Vojak “The most important innovations often begin with the question: Are we solving the right problem?” — Erik Berglund “The best way to be interested in something is to be interested in it.” — Bruce’s advice, via a mentor 🔗 Links & Resources Listen to Bruce Vojak's Episode

    12 min
  5. 107: "Is a New Question More Valuable Than a New Solution When Innovating? ft. Bruce Vojak

    JAN 28

    107: "Is a New Question More Valuable Than a New Solution When Innovating? ft. Bruce Vojak

    Send us a text What if the next big innovation came from a box cutter? Erik sits down with Bruce Vojak—advisor, executive, and author—to explore the surprising, human-driven process of innovation inside mature industries and companies. They unpack the difference between optimization and renewal, the danger of solving the wrong problem, and why some of the most impactful innovators are names you’ll never know. This conversation is a masterclass in shifting paradigms, staying curious, and creating the conditions for real change. 👤 About the Guest Bruce Vojak is an author, researcher, and executive with a lifelong focus on innovation in mature industries. Formerly with Motorola and the University of Illinois, Bruce has co-authored two books: Serial Innovators and No Excuses Innovation, both published by Stanford University Press. His work blends technical insight with human-centered research, emphasizing the role of individuals who drive breakthrough innovation quietly within established firms. 🧭 Conversation Highlights Defining "mature" industries using the S-curve and what it really means to renew themWhy the most important innovations often begin with the question: “Are we solving the right problem?”Real-life examples of invisible innovation: from pre-peeled carrots to safer box cuttersInnovation as a people problem, not just a processThe role of “innovation exemplars” within organizations and why structure matters less than alignmentPitfalls: how well-intentioned quality control or sales policies can crush good ideasThe AI moment: what’s hype, what’s real, and why Bruce isn’t panickingSubmission to reality as the true marker of innovation-ready leadership💡 Key Takeaways Mature ≠ Stagnant: Mature industries aren’t dead—they’re just ripe for a shift in the basis of competition.Define the Right Problem: Many breakthrough innovations come not from new tech, but from redefining what problem you’re solving.Innovation is Personal: It’s not always about a system or culture—it’s often about one persistent person who sees something others don’t.Organizations Must Balance: Great companies hold both optimization and renewal in tension—they don’t let one dominate.Real Data > Hype: Innovators and executives alike must “submit to reality”—let the data, not ego, drive decisions.❓ Questions That Mattered What does maturity mean in the context of innovation—and how do you know when you’ve arrived there?What precedes a truly innovative idea?How can a company structure itself to actually foster innovation instead of pretending to?What gets in the way of great ideas in mature companies—and how do you protect against that?🗣️ Notable Quotes “Innovation at its best is changing the basis of competition. It’s renewal.” — Bruce Vojak “The most innovative thing that occurs is often defining the right problem.” — Bruce Vojak “When companies submit to reality—when data speaks—that’s when innovation becomes possible.” — Bruce Vojak “It’s like musical chairs—where are you going to be when the music stops?” — Bruce Vojak 🔗 Links & Resources No Excuses Innovation by Bruce Vojak & Walter HerbstSerial Innovators by Bruce Vojak, Abbie Griffin & Ray PriceBruce's LinkedIn Profile

    1h 25m
  6. 106: "SMART Goals vs. Vector Goals: Which One Belongs in 2026?" ft. Alli Murphy

    JAN 26

    106: "SMART Goals vs. Vector Goals: Which One Belongs in 2026?" ft. Alli Murphy

    Send us a text In this thought-provoking conversation, Erik and Alli explore a noticeable shift in how people are setting goals in 2026. Instead of laser-focused metrics and traditional SMART goals, more people are choosing intentions, directions, and feelings as their compass. Why? And what does it mean for how we measure success? Together, they unpack the value of vector-based goals, the emerging trend of process over outcome, and why many high achievers are intentionally ditching rigid measurements in favor of something more sustainable—and possibly more effective. ❓ The Big Question Are rigid goals still useful, or is it time to rethink how we measure success? 💡 Key Takeaways SMART goals aren’t dead—but they’re no longer the only path to growth. Many are shifting to qualitative, process-based goals that align with values rather than numbers.Process integrity > Outcome obsession. Focusing too hard on the end result can blind you to the meaningful work already being done.Goals as vectors. Picking a direction and tracking momentum may serve us better than defining a fixed destination.Experiments over expectations. Viewing goals as hypotheses allows you to learn, iterate, and adjust—rather than feeling stuck or like a failure.High-achievers are redefining success. For many, especially those running businesses or on the edge of new growth, clarity and confidence come from feeling aligned—not just hitting numbers.🧠 Concepts, Curves, and Frameworks Vector Goals: Choosing a direction and measuring acceleration, not just arrival.Process Integrity vs. Outcome Integrity (Deborah’s concept): Not all success is about the result—sometimes it’s about how you show up along the way.Hypothesis-Driven Leadership: Every initiative is a test—learn to treat your strategy as a living system.Blinders of Quantification: Rigid metrics can distract from emerging opportunities.Creative Constraints: New habits, products, or businesses often defy neat measurement—especially early on.🔁 Real-Life Reflections Alli shared how she intentionally didn’t set numeric goals in 2026 for her business, favoring creativity and sustainability over spreadsheets.Erik reflected on how, as a founder, forecasting too early can create false precision—so he now leads with qualitative goals and lets quantification come later.Both recognized this as a trend among their mentees and clients, noting that more people are choosing how they want to feel or how they want to work as the real goal.🧰 Put This Into Practice Start with a direction, not a destination. Ask: “If I moved this way, what would feel aligned?”Run your goals like experiments. What hypothesis are you testing?Replace ‘How much?’ with ‘How meaningful?’ Try tracking presence, ease, or momentum.Review your process, not just results. Did you show up the way you said you would?Ditch what doesn’t serve you. If SMART goals feel restrictive, try something else—and own it.🗣️ Favorite Quotes “If you marry yourself too early to an outcome, it takes away your ability to adapt to the humbling reality that might be showing up.” – Erik “For the recovering high achiever in me… this is forcing me to think differently in a way I wouldn’t have expected.” – Alli “The clearer you are on the direction you want to move, the more powerfully you can simplify the steps to get there.” – Erik “You’re the only one who knows you best. Pick what works for you and get rid of the noise.” – Alli “Let’s go run the test. Let’s see if we’re right.” – Erik 🔗 Links & Resources

    20 min

  7. JAN 23

    105: "Do You Know What Kind of Puzzle Piece You’re Actually Looking For?" (lessons from Brett Jesson)

    Send us a text  🧠 Erik’s Take  In this post-interview reflection, Erik revisits key insights from his conversation with Brett Jesson, Chief Growth Officer at DDC Group. What stands out isn’t just Brett’s strategic clarity—it’s the way he pairs operational rigor with a deeply human approach to leadership. Erik dives into three standout themes: the underestimated power of fiction in leadership, the rise of small powerhouse teams, and the brutal honesty required for better hiring. This is a thoughtful unpacking of how leadership evolves when you're willing to look inward first. 🎯 Top Insights from the Interview Fiction builds empathy. Reading novels helps leaders see the world through others’ eyes—and leads to stronger “off the pitch” relationships.Small, high-powered generalist teams outperform bureaucracies. Versatility + trust = agility.Hiring well starts with knowing yourself. If you don’t understand your team’s strengths and gaps, you can’t pick the right puzzle piece.Speed matters in hiring recovery. Catching a wrong hire in 30–60 days is healthy. Waiting 12–24 months is a costly culture problem.Generational shifts are leadership tests. Leading millennials and Gen Z is no longer optional—and it’s not their fault, but it is your responsibility.🧩 The Personal Layer Erik reflects on how Brett’s love of fiction and leadership intersect in surprising ways. From Ender’s Game to Project Hail Mary, storytelling helps leaders build empathy and see patterns in human behavior—both in real life and on their teams. It’s not just intellectual—it's emotional. Brett’s commitment to leveling up as a human, not just a title, is a model Erik finds both refreshing and necessary. 🧰 From Insight to Action Read fiction. Not as escape, but as a tool for emotional fluency.Build generalist-heavy teams and reduce "connective tissue" friction.Redesign your hiring process to test for culture, not just competence.Normalize admitting a hire isn’t working—faster, not later.Reflect: Are you adapting your leadership style to the team you have—or the one you wish you had?🗣️ Notable Quotes “You can't walk in someone’s shoes if you've never imagined them.” “Friction often lives in the connective tissue—small teams cut that out.” “Hiring starts with knowing what you can and can’t train.” “The wrong person can demolish a small, high-powered team.” “By 2030, millennials and Gen Z will be the majority—it’s not their fault, but it is your responsibility.” 🔗 Links & Resources Listen to Brett Jesson's Episode

    12 min
  8. 104: "How Do You Build Culture That Isn’t Just a Slide Deck?" ft. Brett Jesson

    JAN 21

    104: "How Do You Build Culture That Isn’t Just a Slide Deck?" ft. Brett Jesson

    Send us a text In this episode, Erik sits down with Brett Jesson, a strategic leader driving growth at a global business process management enterprise. What unfolds is a conversation that transcends business talk and drills into trust, culture, and the very human side of leadership. From career pivots to hiring with humility, Brett shares how he’s learned to lead small, high-performing teams in big, complex systems—without losing sight of what makes people thrive. It’s a masterclass in emotionally intelligent leadership for scale. 👤 About the Guest Brett Jesson is a senior executive at The DDC Group, where he leads commercial operations for the EMEA region. His career spans client growth, team building, and market origination in highly diverse environments. Brett is known for his strategic clarity and people-first approach—balancing rigor with reflection and operational excellence with emotional insight. He brings both humility and hard-won wisdom to this conversation on leading at the intersection of culture, trust, and performance. 🧭 Conversation Highlights Why small, high-performing teams are often the engine behind outsized impact.The hiring challenge: balancing instinct, bias, and trust in fast-scaling environments.“Pressure without expectation”—how Brett was raised and how it shapes his leadership style.What makes culture more than just words on a wall—and how to make it live in the work.Navigating imposter syndrome and identity across roles, geographies, and seasons of life.💡 Key Takeaways Trust scales faster than any other strategy. Brett unpacks how shared values and high-trust teams create momentum in uncertain markets.Culture must live in the day-to-day. It’s not defined by a slide deck, but by what your team defends, promotes, and expects in real time.Hiring is about alignment, not perfection. You won't get it right every time—but the faster you admit and adjust, the better.Great leadership is not knowing all the answers—it's asking better questions. Brett models humility and intellectual curiosity.The best leaders own their blind spots. Self-awareness isn’t a luxury; it’s a multiplier.❓ Questions That Mattered How do you build trust in distributed, multicultural teams?What kind of pressure leads to growth—and what kind shuts people down?Why is “click” in hiring both powerful and dangerous?How do you make sure your culture lives beyond the onboarding deck?What does it take to lead in ambiguity without needing to control?🗣️ Notable Quotes “The best cultures are validated by clients—not just internal slogans.” “Sometimes hiring is a bet. It’s a feeling. And sometimes it works, and sometimes it doesn’t.” “We’re a small team, so we have to pick the right targets, the right people—and then go get it done.” “It’s not about being right—it’s about staying in alignment.” “Imposter syndrome isn't the enemy. It’s often the sign that you’re stretching into something real.” 🔗 Links & Resources Connect with Brett Jesson on LinkedInCheck out The DDC Group's Website

    1h 31m
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5
out of 5
38 Ratings

About

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.

Information

  • Creator
    Erik Berglund
  • Years Active
    2025 - 2026
  • Episodes
    109
  • Rating
    Explicit
  • Copyright
    © 2026 I Have Some Questions...
  • Show Website
    I Have Some Questions...