Ask For An Answer

Jim Fielding
  • 5.0 (6)
  • Management
  • Updated Weekly

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.

  1. 3d ago

    How To Secure $10 Million in Venture Capital Funding with Allison Byers

    How Do You Raise Capital and Build Success When the System Wasn't Built for You? Allison Byers joins Ask for an Answer with Jim Fielding to discuss self-trust, overcoming trauma, and reclaiming power in venture capital. After walking away from corporate management consulting following a maternity leave ultimatum, Allison co-founded a medical device company out of MIT, raised nearly $10 million, and brought an FDA-registered product to market. When a Series B round stalled, an asset sale turned into a painful wake-up call. The all-male acquiring team went on to raise $55 million using her team's assets. Instead of playing the victim, Allison dived deep into capital allocation research, exposing systemic bias and founding Scroobious to level the playing field for every underrepresented founder. Jim and Allison dig into what it truly takes to navigate inequity without losing your identity. They unpack the power of turning personal hardship into systemic change, why equity investing is a form of everyday voting, and how setting healthy boundaries protects high performers from burnout. Allison also opens up about her grassroots political work with Founders for Kamala, her role in co-authoring California's landmark Fair Investment Practices by Venture Capital Companies Law, and why entrepreneurship gave her back her professional identity. IN THIS EPISODE: 1. How to spot and reframe real-time bias during high-stakes investment pitches. 2. Why separating your personal identity from your company protects mental health. 3. How physical burnout and stress signal the need for immediate boundaries. 4. The key differences between fiduciary venture funds and angel investor groups. 5. How groupthink inside angel networks can accidentally block funding for great ideas. 6. Why female founders deliver more profit per dollar invested despite receiving less capital. 7. How alternative funding sources can liberate founders from demoting themselves for venture money. 8. Why legislative policy and data collection are mandatory for long-term systems change. 9. How treating everyday spending and investing as voting shapes our economy. 10. Why entrepreneurship offers a vital lifeline for reclaiming professional agency. CHAPTER TIMESTAMPS: 01:06 Welcome Allison Byers, author of Fundraising for the Rest of Us 02:40 Origin story: From management consulting to spinning out an MIT medical device 03:45 The asset sale, systemic disparities, and turning trauma into action 08:31 How historical bias shapes check-writing decisions 12:28 Identifying bias inside the room and shifting the narrative 16:50 Physical limits: Battling facial shingles from extreme stress 18:50 Healing through community, partnership, and separating self from business 22:40 Launching Scroobious in 2020 and building a movement 38:34 Why founders shouldn't dim their light for venture capital 42:28 Writing California's historic Fair Investment Practices by Venture Capital Companies Law 55:53 Why consumer dollars and investments dictate daily life 01:00:03 The final question: Why entrepreneurship matters so deeply MEET ALLISON BYERS Allison Byers is a founder, investor, capital access advocate, speaker, and author of Fundraising for the Rest of Us: How to Build Your Pitch, Navigate Bias, and Raise Capital on Your Terms. She is the founder of Scroobious, a relationship-first capital access platform built to scale startup growth for underestimated founders. With experience spanning corporate management consulting and medical device innovation out of MIT, Allison co-authored California’s landmark Fair Investment Practices by Venture Capital Companies Law and serves on multiple boards. ✨ Connect with Allison Byers 🌐 Website: allisonbyers.com | scroobious.com 💼 LinkedIn: Allison Byers | Scroobious 🦋 Bluesky: @apbyers.bsky.social 📸 Instagram: @apbyers | @scroobious 📚 Book: Fundraising for the Rest of Us ✨ Follow Jim Fielding & Ask For An Answer 🌐Website: hijimfielding.com ♥️ Instagram:@hijimfielding 💼 LinkedIn: linkedin.com/in/jimfielding 🔗 Podcast: Ask For An Answer, available on YouTube, Apple Podcasts, and Spotify Subscribe to Ask for an Answer on your platform of choice, and leave a review if you want more of this kind of honest, unscripted conversation. #LeadershipPodcast #FundraisingForTheRestOfUs #WomenInBusiness #StartupCapital #Resilience

  2. Sep 24

    You Don’t Need to Change Your Story — You Need to Own It with Dr. Joel Davis Brown

    What happens when you stop running from your past and finally claim your full story? Dr. Joel Davis Brown joins Ask for an Answer for a deep, soul-stirring conversation about the messy reality of personal transformation, emotional growth, and what it truly means to lead an authentic life. As an awareness agent, organizational development consultant, university professor, and Chief Visionary Officer of Pneumos LLC, Dr. Joel shares how unaddressed trauma and unhealed wounds silently govern our choices until we take ownership of our narrative. Jim and Dr. Joel unpack the subtle art of inner work. They explore why real leadership starts from the inside out, how to break free from generational patterns, and why forgiveness is a physical release rather than a quick, surface-level exercise. Dr. Joel opens up about his journey writing his latest book, reflecting on his relationship with his late father, learning to parent himself, and finding true freedom in total vulnerability. IN THIS EPISODE: How claiming every part of your personal story eliminates the leverage others have over your self-worth.Why authentic leadership requires doing deep internal healing work before attempting to lead external organizations.How unaddressed emotional trauma and anger eventually bleed out onto loved ones and colleagues if left unchecked.Why true healing involves learning to parent yourself and stepping into full governance over your own narrative.How to break the cycle of generational trauma when caring for aging parents or navigating family dynamics.Why forgiveness is an active, physical release of bitterness that makes you lighter rather than a one-time gesture.How overextending yourself for others can actually be a subtle symptom of unhealed personal wounds.Why reframing leadership beyond corporate titles allows you to show up better in everyday personal relationships.How embracing complete stillness without overstimulation restores emotional energy and prevents burnout.Why self-acceptance and inner peace are essential prerequisites before building healthy long-term partnerships. CHAPTER TIMESTAMPS: 00:37 Welcoming Dr. Joel Davis Brown to Ask for an Answer 01:05 What It Means to Be an Awareness Agent and Strategic Storyteller 05:28 The Inspiration Behind Souls of Queer Folk and Redefining Leadership 10:14 Embracing the Beauty and Complexity of Intersectional Human Identity 15:44 Finding Belonging, Community, and Authenticity Across Different Cities 24:09 I Had to Become the Father: Unpacking Healing, Repair, and Letting Go 31:58 Navigating Generational Trauma and Caregiving for Aging Parents 42:42 Owning Your Truth and Finding Total Freedom in Vulnerability 45:49 Redefining Family, Parenting, Mentorship, and Healthy Relationships 53:36 Prioritizing Self-Care Through Stillness and Peace 56:56 Final Thoughts and Closing Remarks Meet Dr. Joel Davis Brown Dr. Joel A. Davis Brown, Esq., PCC, is the Chief Visionary Officer of Pneumos LLC. As a certified leadership, life, and executive coach trained in somatic coaching, Gestalt methodology, and trauma-informed care, Dr. Joel works collaboratively with organizations, civic groups, and professionals to create synergistic cultures, breakthrough performance, and dynamic leaders. He teaches strategic storytelling at a university in France, specializes in cultural intelligence, emotional intelligence, and organizational strategy, and has spent nearly 30 years working with Startups, Non-Profits, Philanthropic Organizations, and Fortune 500 companies. He is the author of Souls of Queer Folk: How Understanding LGBTQ+ Cultural Values Can Transform Your Leadership Practice and I Had to Become the Father: The Art of Healing, Reconciliation, Repair, and Letting Go. ✨ Connect with Dr. Joel Davis Brown 🌐 Website: pneumos.com 💼 LinkedIn: linkedin.com/in/joelanthonybrown 📧 Email: joel@pneumos.com 📚 Books: Souls of Queer Folk & I Had to Become the Father ✨ Follow Jim Fielding & Ask For An Answer: 🌐Website: hijimfielding.com ♥️ Instagram:@hijimfielding 💼 LinkedIn: linkedin.com/in/jimfielding 🔗 Podcast: Ask For An Answer, available on YouTube, Apple Podcasts, and Spotify Subscribe to Ask for an Answer on your platform of choice, and leave a review if you want more of this kind of honest, unscripted conversation.

  3. Sep 17

    She Hid Her Therapy From Her Colleagues—Until Her Daughter Found Out (With Dr. Julie Basler)

    How do you find the courage to lead with total vulnerability when the whole world expects you to stay invincible? Dr. Julie Basler walked away from a high-profile career as a college president to help leaders reclaim their mental health, their boundaries, and their lives without losing their seat at the table. Armed with a PhD in English and decades of leadership experience, Dr. Basler is an author, speaker, and advocate who wrote her transformative book, She Is Strong Enough to Break, to break the silence around female leadership, mental health, and the burden of carrying it all alone. What Happens When Leaders Stop Hiding Behind the Armor? Dr. Julie Basler joins Jim Fielding on Ask for an Answer for a deeply moving conversation about emotional intelligence, personal growth, and the quiet struggles high achievers carry behind closed doors. From secretly going to therapy while running a college to sending a middle-of-the-night email to her entire campus admitting she was broken, Dr. Basler shares the moment her youngest daughter made her realize that hiding mental health struggles teaches the next generation to do the same. Jim and Julie explore how true strength comes from authenticity, why choosing kindness is a radical leadership strategy, and how breaking down opens the door to genuine healing. IN THIS EPISODE: How to recognize when hiding mental health struggles sends the wrong message to those watching you.Why true strength requires stepping away from perfectionism and embracing vulnerability in front of your team.How to shift your focus from the First Mountain of ambition to the Second Mountain of servant leadership.Why simple, intentional acts like handwritten notes can transform how someone feels seen and valued.How standing up for personal values creates long-lasting ripples of courage for others.Why emotional intelligence and high-level leadership belong together in modern organizations.How reframing traffic disruptions or everyday frustration with empathy helps you realize everyone is carrying hidden pain.Why forgiving previous generations for their lack of mental health awareness brings personal peace.How embracing the role of a lifelong learner builds long-term resilience and intellectual curiosity.Why breaking down is often the necessary first step to breaking through into a more authentic life. CHAPTER TIMESTAMPS: 00:00 Teaser: A Daughter's Six Words That Changed Everything 00:40 Introduction: Welcoming Dr. Julie Basler 03:48 From English PhD to College President 06:01 Leaving the Office Behind: Transitioning to the Second Mountain 10:35 The Book: She Is Strong Enough to Break 12:05 Sneaking to Therapy: The Middle-of-the-Night Email 19:40 Writing for Women in Leadership 21:35 The Dinner Table Conversation That Added an Extra Chapter 24:14 Someone Noticed Her: The Power of Handwritten Letters 31:18 Jim's Story: The Indiana University Resignation Letter 37:20 Hidden Pain: Why Everyone Is Carrying Something 41:24 25 Years Later: Going Back to College for Counseling 44:41 Research Notes vs. Tech Dashboards 55:20 Generational Trauma and Forgiving Our Parents 01:03:50 Final Words and Where to Find Dr. Julie Basler MEET DR. JULIE BASLER Dr. Julie Basler is an author, keynote speaker, executive mentor, and President of Strong Teams, a company dedicated to building empathy, service, and compassion in workplace culture. With nearly three decades in higher education leadership, including serving as Vice President of Academic Affairs and President of Platt College for over 18 years, Dr. Basler led her team to achieve initial nursing accreditation with ACEN, the first prelicensure BSN program at a career college to do so. ✨ Connect with Dr. Julie Basler 🌐 Website: juliebasler.com 💼 LinkedIn: Dr. Julie Basler 📚 Book: She's Strong Enough to Break: How Female Leaders Can Reclaim Their Mental Health, Their Boundaries, and Their Lives Without Losing Their Seat at the Table ✨ Follow Jim Fielding & Ask For An Answer: 🌐Website: hijimfielding.com ♥️ Instagram:@hijimfielding 💼 LinkedIn: linkedin.com/in/jimfielding 🔗 Podcast: Ask For An Answer, available on YouTube, Apple Podcasts, and Spotify Subscribe to Ask for an Answer on your platform of choice, leave a review, and share this episode with someone who needs to hear it today. #EmotionalIntelligence #Resilience #MentalHealthMatters #WomenInLeadership #AskForAnAnswer

  4. Sep 10

    From Stage 4 Terminal Cancer to Cancer-Free: The Power of Mindset & Gratitude (With Jenn Greenhut)

    What happens when a life-threatening crisis becomes your greatest catalyst for self-love, healing, and purpose? Jenn Greenhut joins Ask for an Answer for a deeply moving conversation on mindset shifts, emotional intelligence, and finding gratitude in life’s hardest moments. A former elite USA National Team gymnast and UCLA athlete who was used to demanding perfection from her body, Jenn found herself facing rock bottom when a stage IV triple-negative breast cancer diagnosis gave her a 12 percent chance of surviving five years. Instead of seeing the news as a death sentence, a single perspective shift at her oncologist’s office helped her view the diagnosis as a gift that ultimately saved her life. Declared cancer-free just four months later, she turned her personal transformation into a mission to heal and give back. Today, she is the co-author of Everyone Needs a Larry, founder of Love, Zero Negative, and founder of The Zero Negative Foundation, supporting cancer patients, caregivers, and families through their toughest trials. Jim and Jenn dive deep into the emotional themes that shape true resilience: shifting from asking "why is this happening to me" to "what is in this for me," replacing self-judgment with unconditional love, and trusting the journey even through trauma. Jenn shares her experience of navigating a terminal diagnosis as a newlywed, the unique bond between a patient and caregiver, and how elite sports discipline shaped her mindset during recovery. They also explore the power of staying present, managing life choices after career-altering injuries, and how simple daily anchors like her "Pinch Me" method can pull you back into gratitude. IN THIS EPISODE: How shifting your mindset from punishment to protection can turn life's scariest obstacles into gifts.Why asking "what is in this for me" creates openness, curiosity, and emotional growth during adversity.How childhood trauma and high-performance pressure create toxic patterns of self-worth tied strictly to achievement.Why self-love and gratitude serve as powerful emotional superpowers for physical and mental healing.How to navigate a severe medical diagnosis as a newlywed while honoring the critical role of caregivers.Why trusting your medical team allows you to surrender outcome control and focus entirely on present healing.How elite athletic discipline provides psychological strength during personal health battles.Why pivoting away from a lifelong dream like the Olympics can open up unexpected new chapters of fulfillment.How to build an intentional brand and nonprofit foundation to support patients and caregivers.Why using simple tools like the "Pinch Me" method snaps you out of anxiety and grounds you in present gratitude. CHAPTER TIMESTAMPS: 03:04 Facing a Stage IV Cancer Diagnosis and IVF Struggles 06:02 The Medical Moment That Shifted Her Perspective 08:24 Becoming Cancer-Free in Four Months Through Love and Gratitude 11:47 Turning Trauma Into Purpose and Giving Back 16:28 Writing Everyone Needs a Larry and the Caregiver Journey 21:32 Life as an Elite USA National Team Gymnast 37:33 The Sacrifices of High-Level Athletics and Personal Worth 42:40 Expanding Grants for Families and Fundraising Events 44:45 Pitching and Preparing for a TEDx Talk 48:22 Asking Better Questions and Leading With Curiosity 53:14 Jim Shares His Father’s Story With Pancreatic Cancer 01:00:15 Navigating Genetic Markers and Health Decisions 01:02:08 The Pinch Me Method for Staying Present Meet Jenn Greenhut Jennifer "Jenn" Greenhut is a TEDx speaker, author, and founder whose work explores healing, resilience, and transforming life's hardest challenges into opportunities for growth. After becoming cancer-free four months following a stage IV breast cancer diagnosis, Jenn dedicated her life to helping others heal. She is the co-author of Everyone Needs a Larry, founder of Love, Zero Negative, and founder of The Zero Negative Foundation, a nonprofit supporting cancer patients, caregivers, and families. ✨ Connect with Jenn Greenhut: 🌐 Website: www.lovezeronegative.com 🌐 Foundation: www.zeronegativefoundation.org ♥️ Instagram: @lovezeronegative @jenngreenhut @zeronegativeorg 💼 LinkedIn: linkedin.com/in/jennifergreenhut 🎥 TEDx Talk: TEDxRobinsonRoad - Jennifer Greenhut ✨ Follow Jim Fielding & Ask For An Answer: 🌐Website: hijimfielding.com ♥️ Instagram:@hijimfielding 💼 LinkedIn: linkedin.com/in/jimfielding 🔗 Podcast: Ask For An Answer, available on YouTube, Apple Podcasts, and Spotify Subscribe to Ask for an Answer on your platform of choice, and leave a review if you want more of this kind of honest, unscripted conversation. #LeadershipPodcast #EmotionalIntelligence #PersonalTransformation #Resilience #CancerSurvivor #OvercomingAdversity #MindsetShift

  5. Sep 3

    The Simple 3-Question Test That Reveals a Leader's True Character (With Adam Bryant)

    How do the world’s most successful leaders learn to navigate massive pressure, personal trauma, and total uncertainty? Adam Bryant spent over a decade interviewing more than 500 CEOs for The New York Times Corner Office series. Now Senior Managing Director and Partner at The ExCo Group, Adam joins Jim Fielding on Ask for an Answer to break down what actually makes or breaks a leader when the stakes are highest. From asking executives about their childhood memories instead of their quarterly earnings to recognizing why resilience in the face of early adversity is the ultimate differentiator, Adam brings decades of journalism experience and human insight into one powerful conversation. The two reflect on why leading today is harder than ever before and how authentic leadership means closing the gap between how you want to be perceived and how people actually decode you. Adam explains why so much traditional leadership advice falls short when real human beings are brought into the equation. The conversation wraps up with a sharp look at why active listening is the ultimate underrated superpower for anyone trying to build real trust and followership. KEY TAKEAWAYS: How early life adversity, family dynamics, and personal setbacks shape the internal drive needed for executive success.Why birth order and childhood expectations heavily influence your default leadership style and team management habits.How to manage the control-freak instinct that gets you promoted before it burns you out.Why your greatest professional strength can easily double as your biggest weakness without deep self-awareness.How to close the gap between how you want people to perceive you and how they actually decode your actions.Why practical human wisdom beats rigid, cookie-cutter leadership theories every single time.How to build psychological safety in remote or hybrid teams by intentional effort toward creating a sense of us.Why admitting you do not have all the answers creates stronger solutions from your entire team.How active listening serves as a foundational superpower containing humility, curiosity, and respect.Why processing information rather than just hearing it transforms surface conversations into real connection. CHAPTER TIMESTAMPS: 03:26 The Origin of Corner Office: Asking CEOs About Their Childhoods 05:54 The Three Opening Questions That Uncover Real Vulnerability 10:25 Indicators of Success: Why Early Adversity Drives High Achievers 15:10 Unpacking Sibling Order, Family Expectations, and Leadership Traits 17:39 Deprogramming Control Freak Tendencies to Avoid Burnout 25:46 Starting at the Bottom: Adam’s 30-Year Journey in Journalism 29:27 The Pivot to Executive Mentoring at ExCo Leadership Group 31:09 Why Most Cookie-Cutter Leadership Theories Fail in Practice 37:44 The Dual Challenge of Modern Leadership: Authenticity and Pressure 41:39 Navigating Hybrid Work Culture and Building Real Team Connection 51:42 The Underrated Leadership Superpower: Active Listening Meet Adam Bryant Adam Bryant is a veteran journalist, author, speaker, and Senior Managing Director and Partner at The ExCo Group. Across his 30-year career in journalism, including two stints at The New York Times, he interviewed more than 1,000 CEOs and board directors and created the renowned Corner Office column. He has authored four books on leadership, including The Corner Office and The CEO Test, focusing on practical, actionable insights for modern leaders navigating complex human dynamics. ✨ Connect with Adam Bryant 🌐 Website: excoleadership.com 💼 LinkedIn: linkedin.com/in/adambryantleadership 📚 Books: The CEO Test, The Corner Office, Quick and Nimble, Jump-Start Your Career ✨ Follow Jim Fielding & Ask For An Answer: 🌐Website: hijimfielding.com ♥️ Instagram:@hijimfielding 💼 LinkedIn: linkedin.com/in/jimfielding 🔗 Podcast: Ask For An Answer, available on YouTube, Apple Podcasts, and Spotify Subscribe to Ask for an Answer on your favorite platform, and leave a review to help us bring you more honest, unscripted conversations! #LeadershipPodcast #EmotionalIntelligence #Resilience #ExecutiveCoaching #ActiveListening

  6. Aug 6

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

    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

  7. Jul 30

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

    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 futureHow to have productive conversations with people you fundamentally disagree withThe leadership qualities the next generation of political leaders will needWhy democracy depends on participation, not perfectionHow radical kindness, curiosity, and community can bridge even our deepest divides Chapter Timestamps00:00 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

  8. Jul 23

    The One Belief Behind Every Successful Career Pivot | #30

    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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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.

Information

  • Creator
    Jim Fielding
  • Years Active
    2025 - 2026
  • Episodes
    54
  • Rating
    Explicit
  • Copyright
    © 691291
  • Show Website
    Ask For An Answer

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