Ask For An Answer

ASK FOR AN ANSWER is more than a podcast—it’s a practice space for real leadership. Hosted by Jim Fielding, each episode features an honest, unscripted conversation with a leader facing a real challenge: a hard transition, a high-stakes decision, or a moment when the answers aren’t clear. Together, they work through it in real time with clarity, candor, and a growth mindset. This isn’t abstract theory or polished performance. It’s leadership as it actually happens: live, thoughtful, and grounded in shared insight. More than anything, ASK FOR AN ANSWER captures what it sounds like when leaders stop performing and start thinking—when they lower the armor, ask for help, and trust the process. If you believe leadership is a practice, not a pose, this podcast is for you.

Ask For An Answer is a business podcast hosted by Unknown Host, with 49 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Unknown Host hosts Ask For An Answer, a business show with 49 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

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  Episode #32

  The 3 Leadership Lessons That Changed Me (Season 2 Recap) | #32

  Aug 6, 202618 min

  What Happens After 31 Conversations With Extraordinary Leaders? After an unforgettable second season of Ask for an Answer , Jim Fielding steps behind the microphone alone to reflect on the biggest lessons that emerged from 31 conversations with CEOs, creatives, public servants, founders, athletes, journalists, and changemakers. This isn't a highlight reel. It's a deeply personal look at what changed Jim's own thinking about leadership, curiosity, and what it really means to ask better questions. Drawing on conversations with guests like Jeremy Hobson, Olivia Jordan, Marie Harf, Gerardo Celasco, Ryan Stana, and Brad Stulberg, Jim shares the three ideas that kept resurfacing all season—and why they've become the foundation of his next book. More importantly, he explains why leadership isn't about having the right answers. It's about creating the conditions where better questions can be asked. What Are the Three Lessons Every Leader Needs? Jim explores how the best leaders don't walk into a room trying to win—they walk in ready to learn. He reflects on why asking honest questions always comes with personal risk, why consistency matters more than breakthrough moments, and why kindness isn't soft leadership. It's one of the strongest leadership strategies we have. He also shares a personal update, including why he's taking a short break from the podcast to finish his second book and what's coming in Season 3 of Ask for an Answer. Whether you've listened to every episode or you're discovering the show for the first time, this conversation captures what the podcast has always been about: curiosity, humanity, and leading with intention. KEY TAKEAWAYS Why the best leaders enter conversations ready to learn, not ready to win. How asking better questions creates stronger teams, deeper trust, and better decisions. What Jeremy Hobson, Olivia Jordan, Marie Harf, Ryan Stana, Brad Stulberg, and Gerardo Celasco taught Jim about modern leadership. Why clarity is an act of kindness, especially during difficult conversations. How consistency—not breakthrough moments—is what actually builds meaningful work. Why leaders should stop performing and start listening. The leadership philosophy behind Jim's upcoming second book. Why rest isn't the reward for great work—it's part of doing great work. What listeners can expect from Season 3 of Ask for an Answer. Follow Jim Fielding & Ask For An Answer Website: hijimfielding.com Instagram: @hijimfielding LinkedIn: James (Jim) Fielding Podcast: Ask For An Answer on YouTube, Apple Podcasts, and Spotify Community: LeagueOfRadicalKindness.com If this episode reminded you that leadership starts with better questions, subscribe to Ask for an Answer and leave a review. It helps more curious leaders discover the show. CHAPTER TIMESTAMPS 00:00 Welcome to the Season 2 Recap 01:15 Lesson One: How You Walk In Changes the Room 03:05 Lesson Two: The Questions That Cost You Something 05:00 Lesson Three: What You Keep Is What You Become 07:00 The Leadership Philosophy Behind Jim's Next Book 09:10 Gratitude for Season 2's Guests and Community 10:45 Why Jim Is Taking a Short Break 12:15 Inside the League of Radical Kindness 13:15 Season 3 Preview: What's Coming Next 14:30 Final Reflections: Why Questions Still Matter Most

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  Episode #31

  Beyond the Echo Chamber: Marie Harf on Democracy, Dialogue, and Leading Through Division

  Jul 30, 20261h 11m

  What does authentic leadership look like in a world that's more divided than ever? How do you have meaningful conversations with people who see the world completely differently? And what happens when democracy itself is being tested? In the final guest episode of Season 2 of Ask for an Answer , Jim Fielding sits down with foreign policy expert, political analyst, and University of Pennsylvania executive director Marie Harf for a candid conversation about leadership, civic responsibility, and why engaging across differences matters now more than ever. Drawing on her experience at the CIA, the U.S. State Department, and nearly a decade as a Democratic political analyst on Fox News, Marie shares what she's learned about communicating across political divides, America's changing role on the global stage, and why thoughtful disagreement is essential to a healthy democracy. Together, Jim and Marie explore the challenges facing the Democratic Party ahead of the 2026 midterms and 2028 presidential election, the qualities the next generation of leaders will need, and why hope, curiosity, and community remain powerful forces during uncertain times. Whether you're passionate about politics, interested in leadership, or simply looking for a thoughtful conversation about where we go from here, this episode offers perspective without sacrificing nuance. In this episode, you'll learn: Why America's role in the world is changing and what it means for the future How to have productive conversations with people you fundamentally disagree with The leadership qualities the next generation of political leaders will need Why democracy depends on participation, not perfection How radical kindness, curiosity, and community can bridge even our deepest divides Chapter Timestamps 00:00 Why Democracy Depends on Better Conversations 03:15 Marie Harf's Journey from the CIA to Fox News 08:05 America's Changing Role in the World 18:20 Inside Fox News: Finding Common Ground Across Political Divides 31:00 What Democrats Need to Learn Before the Next Election 42:15 The Leaders to Watch for 2028 50:00 Why Democracy Requires More Than Winning Elections 54:30 Hope, Civic Responsibility, and Building a Better Future Together Meet Marie Harf Marie Harf is a former CIA analyst and State Department Deputy Spokesperson who has spent her career at the intersection of foreign policy, national security, and public communication. She is the Executive Director of Perry World House at the University of Pennsylvania and has been a Democratic political analyst on Fox News for nearly a decade, where she brings thoughtful perspective to some of the country's most important conversations about democracy, leadership, and America's role in the world. Instagram: @marieharf LinkedIn: Marie Harf Follow Jim Fielding & Ask For An Answer: Website: hijimfielding.com Instagram: @hijimfielding LinkedIn: James (Jim) Fielding If this conversation resonates with you, subscribe to Ask for an Answer , leave a review, and share this episode with someone who believes better conversations can lead to a better future. #LeadershipPodcast #Democracy #PoliticalLeadership #ForeignPolicy #CivilDiscourse

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  Episode #30

  The One Belief Behind Every Successful Career Pivot | #30

  Jul 23, 202659 min

  Leslie Grandy worked for James Cameron and Brian De Palma, then walked away from Hollywood at 35 to start over as the most junior person on a tech team. That decision led to Apple, Amazon, T-Mobile, and a career built on one belief: you can figure it out. What Happens When You Stop Waiting for Permission to Pivot? Leslie Grandy joins Ask for an Answer for a freewheeling conversation about self-trust, reinvention, and why creative confidence matters more than ever in the age of AI. A Northwestern film graduate who earned her way into the Directors Guild of America with no industry connections, Leslie built a successful Hollywood career before realizing the lifestyle would cost her the relationship and the life she actually wanted. So she got an MBA, took an entry-level product role, and rebuilt from scratch. That second act took her through Visio's billion-dollar sale to Microsoft, the first Android phone launch at T-Mobile, and product leadership roles at Apple, Best Buy, Discovery, and Amazon. Jim and Leslie dig into what made the pivot work: choosing what you're moving toward instead of running from what isn't working, trusting your own judgment over external approval, and having the humility to swallow your ego when starting over. Leslie shares the story of applying to exactly one college, early admission only, because she believed she'd get in. She did. Can You Stay Creative When AI Does the Thinking for You? The conversation turns to Leslie's award-winning book, Creative Velocity: Propelling Breakthrough Ideas in the Age of Generative AI. Leslie makes the case that creativity isn't a talent you're born with. It's a capacity everyone carries and most people abandon, especially now, when a machine can hand you polished output with no soul behind it. She and Jim talk about using AI as a thinking partner rather than a replacement, why leaders must build environments where teams believe they can solve unfamiliar problems, and how curiosity connects directly to the Ask for an Answer philosophy of leading with questions instead of certainty. The episode closes with a candid look at redefining retirement. Leslie's definition is simple: never doing anything she doesn't want to do. From teaching executive education at the University of Washington to planning a life with a husband 22 years her senior, she shows what it looks like to design your time around joy, vitality, and learning. Her answer to Jim's final question, what she'd tell her younger self, is one every high achiever needs to hear. KEY TAKEAWAYS How to know when a career pivot is right by identifying what you're moving toward instead of what you're escaping. Why creative confidence, not raw talent, determines who solves unfamiliar problems and who runs from them. How to use generative AI as a thinking partner without surrendering the human creativity that gives work meaning. Why starting over at a lower level requires ego management, and how self-belief makes the trade worth it. How prioritizing a core relationship can clarify major career decisions instead of complicating them. Why leaders who admit they don't have all the answers draw better solutions from their teams. How curiosity and the willingness to say "I don't know how this works yet" build durable self-confidence. Why the best answers in a room often come from the most junior or unexpected voices. How to define retirement as freedom of choice rather than the absence of work. Why going easier on yourself may be the most important leadership lesson high performers learn too late. CHAPTER TIMESTAMPS 00:00 Introduction: Welcoming Leslie Grandy 02:18 From Northwestern Film School to the Directors Guild 03:14 The Pivot: An MBA and a Billion-Dollar Startup Exit 06:01 The Two Moments That Made Leaving Hollywood Clear 08:12 Choosing a Relationship Over Industry Stature 09:57 Self-Approval Instead of External Validation 11:03 Starting Over at 35 and Managing the Ego 13:22 Building Self-Trust Without Role Models 16:11 Betting on Herself: The One-School College Application 21:55 A Totaled Car and the Problem-Solver Instinct 26:45 Why Leslie Wrote Creative Velocity 28:51 Protecting Human Creativity in the Age of AI 32:07 Curiosity as the Foundation of Creative Confidence 34:17 Why Leaders Don't Need All the Answers 36:50 Redefining Retirement: Only Doing What Brings Joy 41:36 Planning Life and Retirement With a 22-Year Age Gap 43:19 Money, Timing, and the Freedom to Choose 49:35 Aging, Vitality, and the Morning Body Inventory 54:32 Ask for an Answer: What Leslie Would Tell Her Younger Self 56:46 Closing Thoughts Meet Leslie Grandy Leslie Grandy is a product executive, speaker, and CEO advisor who spent 25+ years leading first-to-market products at Apple, Amazon, T-Mobile, Best Buy, and Discovery after an early career in film as a Directors Guild of America assistant director for Brian De Palma and James Cameron. She's the author of Creative Velocity: Propelling Breakthrough Ideas in the Age of Generative AI (Wiley), founder of The Product Guild, and an executive educator at the University of Washington's Foster School of Business. ✨ Connect with Leslie Grandy Website: lesliegrandy.com LinkedIn: Leslie Grandy Book: Creative Velocity: Propelling Breakthrough Ideas in the Age of Generative AI ✨ Follow Jim Fielding & Ask For An Answer: Website: hijimfielding.com ♥️ Instagram: @hijimfielding LinkedIn: James (Jim) Fielding Podcast: Ask For An Answer, available on YouTube, Apple Podcasts, and Spotify

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  Episode #29

  How to Build a Personal Brand That Actually Matters with Vanessa Errecarte | #29

  Jul 16, 202658 min

  Can you build a successful career if no one understands the value you bring? In this episode of Ask For An Answer , Jim Fielding sits down with marketing strategist, educator, and author Vanessa Errecarte for a conversation about visibility, leadership, and why personal branding has become one of the most important professional skills in today's AI-driven world. Vanessa never planned to become an author. While teaching MBA students at UC Davis, she noticed a pattern. Some of the most talented people in the room struggled to communicate what made them different. As technology made expertise easier to access, standing out became less about credentials and more about helping people understand the value only you can create. That realization became Valuable and Visible , a book that challenges the traditional idea of personal branding. Instead of focusing on self-promotion, Vanessa argues that the strongest personal brands are built through service, generosity, and genuine expertise. Jim and Vanessa also reflect on their coaching relationship, the realities of writing a book while balancing career and family, and why asking for help is often the catalyst for meaningful growth. What Does It Mean to Be Valuable in an AI World? As artificial intelligence reshapes nearly every industry, Jim and Vanessa explore what technology can and cannot replace. They discuss why AI rewards people who think clearly, communicate authentically, and build trust over time. Rather than competing with technology, professionals have an opportunity to become even more human by developing relationships, sharing ideas, and leading with curiosity. The conversation also dives into coaching, confidence, family, entrepreneurship, and the discipline required to keep growing even after you've reached professional success. Key Takeaways Why personal branding is really about serving others instead of promoting yourself. How teaching MBA students inspired the ideas behind Valuable and Visible . Why AI is changing careers without replacing the need for human connection. The role coaching plays in building confidence, perspective, and long-term growth. How writing a book transforms the way you think about your own expertise. Why saying no is often more important than saying yes. The challenge of balancing leadership, entrepreneurship, and family life. How visibility creates opportunity long before you need it. Why authentic relationships will always outperform manufactured influence. The mindset shift that helps professionals stay relevant in a rapidly changing world. Meet Vanessa Errecarte Vanessa Errecarte is a marketing strategist, executive coach, UC Davis Graduate School of Management instructor, and the author of Valuable and Visible . Through her consulting, teaching, and coaching, she helps professionals and organizations build brands rooted in trust, expertise, and meaningful impact. ✨ Connect with Vanessa: 🌐Website: vanessaerrecarte.com 💼 LinkedIn: Vanessa Errecarte ♥️ Instagram: @vanessaerrecarte 📖 Book: Valuable and Visible ✨ Follow Jim Fielding & Ask For An Answer: 🌐Website: hijimfielding.com ♥️ Instagram: @hijimfielding 💼 LinkedIn: James (Jim) Fielding 🔗 Podcast: Ask For An Answer, available on YouTube, Apple Podcasts, and Spotify If this conversation challenged the way you think about personal branding, leadership, or your own career, subscribe to Ask For An Answer and leave a review. It helps more thoughtful conversations reach the people who need them most. Chapter Timestamps 00:00 Welcome and how Jim and Vanessa first connected through coaching and books 02:06 The classroom insight that sparked Valuable and Visible 05:53 Why personal branding matters even more in the age of AI 10:25 Balancing entrepreneurship, family, and writing a book 15:20 How coaching creates lasting personal and professional growth 20:25 Why asking for help is a leadership strength 30:23 Launching a book while managing real life 35:14 The power of saying no and protecting your energy 45:09 Why relationships shape every career opportunity 50:17 What AI can never replace

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  Episode #28

  Why Do Curious Leaders Build Better Companies? | #28

  Jul 9, 202658 min

  Bruno Gavino built a 30-person global digital agency from Lisbon. Then he started asking whether AI was quietly making everything his agency did irrelevant. His answer wasn't to panic. It was to build. What Happens When an Introvert Becomes the Face of an AI Company? Bruno Gavino is the CEO and founder of CoDesign, a digital agency based in Lisbon, Portugal, with offices in Boston, Singapore, and Los Angeles. He's also the creator of LLM Search Console, a tool that tracks how brands are showing up (or not showing up) across AI platforms like ChatGPT, Claude, Gemini, and Perplexity. He joined Jim all the way from Portugal for a wide-ranging conversation about building globally while staying rooted, leading teams through constant change, and why curiosity isn't just a nice-to-have. It's the only filter that matters in hiring. This episode covers a lot of ground fast. Bruno and Jim talk through what it actually feels like to run a service business at the exact moment AI is automating the services you've built your company around. They get into the regulatory patchwork both in Europe and the U.S., why the biggest AI models are trending toward generic, and why Bruno thinks smaller, more specific models may ultimately win for real-world business use cases. How Do You Build a Team That Thrives on Uncertainty? Some of the best material in this conversation is about hiring and culture. Bruno uses curiosity as a literal metric in every interview. His team members from unrelated departments conduct screening conversations specifically designed to surface how candidates think, not what they know. His rule of thumb: don't hire anyone you couldn't sit with in a car for three hours. He learned that one the hard way, after a run of great resumes that went nowhere. Bruno is also candid about the harder personal stuff. He talks about growing up with a grandmother whose philosophy of radical kindness still anchors him, a voice in his head that sounds very different from the corporate achievement pressure most founders carry. He discusses the challenge of always trying to fix everyone's problems, the discipline of learning to say no, and why, after 10 years of building, he still doesn't feel like he's winning. Jim shares his own parallel journey: leaving corporate at Disney and DreamWorks, learning Canva from YouTube videos, breaking his website the day of this recording, and discovering that being on your own forces a kind of nimbleness that nobody in a big organization ever needs. The conversation closes on agriculture, pomegranates, Portugal, and why both of them think the best leaders have more in common with good farmers than they do with most people in Silicon Valley. KEY TAKEAWAYS Why measuring brand visibility across AI platforms like ChatGPT and Gemini is the new version of SEO, and why most companies aren't doing it yet. How to use curiosity as a quantifiable hiring metric, including what kinds of interview questions actually surface it. Why the broader and more general AI models become, the more opportunity opens up for niche, domain-specific alternatives. How building your team around where the talent lives, rather than where your office is, creates stronger culture than proximity ever did. Why the most dangerous hire isn't someone underqualified. It's someone with a beautiful resume and no chemistry. How European regulatory experience with GDPR is giving companies like CoDesign a faster adaptation cycle than their American counterparts as AI regulations ramp up. Why curiosity looks easy in younger workers not because they're smarter, but because they have fewer hard-won habits to unlearn. What it costs emotionally to build a company with a close friend, and the practices that keep the relationship intact over a decade. How radical kindness, modeled by a grandmother, became the anchor for a tech founder navigating an industry obsessed with speed and scale. Why founders who learn to say no to problems they can't control become measurably more effective than those who keep trying to fix everything. Meet Bruno Gavino Bruno Gavino is the founder of CoDesign, a global digital agency headquartered in Lisbon, Portugal, and the creator of LLM Search Console, an AI intelligence platform that tracks brand performance across large language models. He also hosts the Voice of Experts podcast, where he interviews leading thinkers in AI and digital strategy. ✨ Connect with Bruno: 💼 LinkedIn: Bruno Gavino 🌐Website: codedesign.org 🔗Podcast: Voice of Experts ✨ Follow Jim Fielding & Ask For An Answer: 🌐Website: hijimfielding.com ♥️ Instagram: @hijimfielding 💼 LinkedIn: James (Jim) Fielding 🔗 Podcast: Ask For An Answer, available on YouTube, Apple Podcasts, and Spotify Did this conversation make you think differently about curiosity, hiring, or what it means to lead through change? If so, subscribe to Ask for an Answer and leave a review. It's the best way to help more people find the show. #LeadershipPodcast #AILeadership #FounderMindset #GlobalBusiness #AskForAnAnswer

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