The Kind Leader

Gino Degregori
  • 4.4 (7)
  • Management
  • Updated Weekly

Navigating Business with Empathy! This podcast is to inspire and equip current and aspiring business leaders to incorporate kindness and empathy into their leadership styles. By presenting real-world examples, interviews with thought leaders, and actionable strategies, the podcast aims to shift the paradigm of leadership from merely transactional to more compassionate and ethical, but most importantly transformational. We want to also serve as a platform to encourage strong, kind leadership that not only enhances corporate performance but also makes a generational impact by transforming organizational cultures for the better. The target audience includes corporate executives, managers, small business owners, and tech leaders who are interested in nurturing more humane, sustainable work environments while driving business success.

  1. 5d ago

    The AI Leadership Trap: Mistaking Speed For Clarity

    AI can give you an answer in seconds. But speed can create something dangerous for leaders: The illusion of clarity. In this episode of The Kind Leader Podcast, Gino Degregori sits down with Adrian Wolfberg, organizational change consultant, author, and former naval officer and intelligence analyst who has spent his career studying how people make decisions when the information is incomplete, the stakes are high, and certainty is impossible. Adrian warns that as AI gets faster and more capable, leaders face a new trap: mistaking an immediate answer for a deep understanding of the problem. He calls it "borrowed clarity", the feeling of certainty before you've actually done the work to earn it. Because AI can process information, recognize patterns, and generate recommendations faster than any human. But it can't replace the judgment, context, and human understanding that make those recommendations meaningful. Together, Gino and Adrian explore: • Why AI can create the illusion of clarity • The difference between "borrowed clarity" and earned clarity • Why framing the right problem matters more than generating a fast answer • The "time trap" leaders face as AI accelerates decision-making • Why sometimes the smartest thing a leader can do is slow down • How human judgment becomes more valuable as AI gets more powerful • Why trust must exist before human-AI collaboration can work • How the CARES Framework applies to leadership in the age of AI This conversation goes far beyond learning how to use AI. It's about knowing what you should never outsource to it. Because the future won't belong to the leaders who get answers the fastest. It will belong to the ones who know when to slow down long enough to understand the problem first.   Connect with Adrian Wolfberg Website: oicllc.org LinkedIn: linkedin.com/in/adrianwolfberg Resources Mentioned Who Leads When AI Thinks?: How Leaders Frame Decisions and Exercise Judgment by Adrian Wolfberg — Explore how leaders can determine the right balance between AI and human judgment when navigating increasingly complex problems. Get the Book The CARES Framework Toolkit: Explore the five traits of kind leadership and download the toolkit: thekindleaderpodcast.com/cares-framework/ The Kind Leader Newsletter: Get new episodes, leadership insights, and practical resources delivered to your inbox: thekindleaderpodcast.com Connect with The Kind Leader Podcast Website: TheKindLeaderPodcast.com YouTube: Kind Leader Podcast Apple Podcasts: The Kind Leader Spotify: The Kind Leader Email: thekindleader@bravocg.com       Chapters: 00:00 The future of leadership and AI 00:22 Introducing Adrian Wolfberg and his expertise 01:22 Adrian's background in high-stakes decision environments 04:55 What does being a kind leader mean? 06:03 The CARES principles of kindness in leadership 07:18 The danger of borrowed clarity in AI 08:40 Accountability in the age of AI 10:48 Building trust through relationships 13:48 The importance of empathy in leadership 16:33 The shared consciousness between humans and AI 26:02 The importance of framing problems in AI collaboration 30:22 Can AI ever truly frame a problem? 32:10 The time trap and managing speed in AI environments 34:54 Slowing down to build trust and understanding 36:43 The role of vulnerability and authenticity in leadership 40:38 Rapid fire: What AI will never do as well as humans 41:54 The one truth for leaders in the AI age 43:48 Closing thoughts and resources

    The AI Leadership Trap: Mistaking Speed For Clarity

  2. Aug 12

    Your Team Is Carrying More Than You Know

    Someone on your team is struggling right now. You may not know who. They may never tell you. And how you lead before that conversation happens may determine whether they ever feel safe enough to. In this episode of The Kind Leader Podcast, Gino Degregori sits down with Ralph Kellogg, Chief Human Resources Officer at Lutheran Family Services of Nebraska, founder of Connection Point Consulting, TEDx speaker, professor, and author, to explore what leaders can do when someone on their team is carrying more than they can see. Drawing from decades in human resources and deeply personal experiences that shaped his own leadership, Ralph challenges leaders to look beyond performance, deadlines, and job titles and recognize the human being behind the work. Because when someone finally trusts you enough to say, "I'm struggling," your job isn't necessarily to fix the problem. It's to know how to respond. Together, Gino and Ralph explore: How to recognize when someone on your team may be struggling Why immediately "fixing" someone's problem can do more harm than good The ACT Framework: Acknowledgment, Collaboration & Communication, and Transparency How small, consistent actions build psychological safety and trust Why leaders need to see people as more than resources or assets How vulnerability and personal experience shape the way we lead Why one genuine check-in can matter more than you realize This conversation goes far beyond mental health in the workplace. It's about becoming the kind of leader people trust when life gets hard. Because you may never know what someone on your team is carrying. But you can make sure they don't have to carry it alone.   Connect with Ralph Kellogg Website: ralphkellogg.com LinkedIn: https://www.linkedin.com/in/ralphkellogg/ Resources Mentioned Leading While Human: Notes I Wish Someone Had Given Me by Ralph Kellogg The CARES Framework Toolkit: thekindleaderpodcast.com/cares-framework/ The Kind Leader Newsletter: thekindleaderpodcast.com Connect with The Kind Leader Podcast Website: TheKindLeaderPodcast.com YouTube: Kind Leader Podcast Apple Podcasts: The Kind Leader Spotify: The Kind Leader Email: thekindleader@bravocg.com

    Your Team Is Carrying More Than You Know

  3. Aug 5

    The More You Control, The Less Your Team Can Grow

    Most leaders don't think they're controlling. They think they're protecting the outcome. But the more decisions they hold, the more answers they provide, and the more closely they manage every detail, the less room their people have to grow. In this episode of The Kind Leader Podcast, Gino Degregori sits down with Marc Inzelstein, co-founder and Chief Leadership Officer of Indiggo, author of Essential Leadership: Practicing L.O.V.E. in Turbulent Times, and an executive advisor who has spent more than 25 years helping senior leaders and teams navigate complexity, growth, and transformation. Throughout his career, Marc has discovered that the habits which help leaders succeed early, moving fast, solving every problem, and staying in control, can quietly become the very things that hold their teams back. Because leadership isn't about controlling people. It's about creating the conditions where they can flourish. Together, Gino and Marc explore: Why letting go is one of leadership's greatest challenges How control quietly limits trust, ownership, and growth Why kindness requires both encouragement and accountability The difference between transactional and transformational leadership How your emotional state shapes every room you enter Why leaders need both mindset and "heartset" The L.O.V.E. Framework: Letting Go, Oneness, Vision, and Energy Why the energy you bring matters more than you realize This conversation goes far beyond leadership styles. It's about recognizing when your need to help has become a need to control. Because every decision you refuse to release is an opportunity your team never gets to own. And the more you control… …the less they can grow.   Resources Mentioned Essential Leadership: Practicing L.O.V.E. in Turbulent Times by Marc Inzelstein The CARES Framework Toolkit: thekindleaderpodcast.com/cares-framework/ The Kind Leader Newsletter: thekindleaderpodcast.com Connect with Marc Inzelstein Website: essential-leadership.com LinkedIn: Marc Inzelstein Connect with The Kind Leader Podcast Website: TheKindLeaderPodcast.com YouTube: Kind Leader Podcast Apple Podcasts: The Kind Leader Spotify: The Kind Leader Email: thekindleader@bravocg.com

    The More You Control, The Less Your Team Can Grow

  4. Jul 29

    The CARES Framework: Clarity | Understand Yourself Before You Lead Others

    For years, Gino Degregori tried to become the leader he thought everyone else needed. The confident CEO. The person with every answer. The leader involved in every decision. But the harder he tried to become that person, the further he moved from the leader he actually was. After 18 years of building Bravo, Gino began to understand that leadership clarity does not start with strategy, vision, or a title. It starts with knowing yourself. In this first deep dive into the CARES Framework, Gino explores Clarity, the C in CARES, and why understanding your strengths, limitations, and natural leadership style must come before leading anyone else. He shares his evolution from a behind-the-scenes developer to CEO, the imposter syndrome that followed him along the way, and the assessment that finally gave him language for the leader he had been trying to understand. In this episode, you'll discover: • Why trying to become the "ideal leader" can pull you away from yourself • How clarity helps disrupt imposter syndrome • What Gino learned about his strengths and blind spots • Why leaders do not need to have every answer • How focusing on your strengths can create more value than fixing every weakness • Why letting go may be the thing your team needs most • Three questions that reveal how others experience your leadership • How self-awareness helps you lead more authentically at work and at home This conversation goes far beyond personality assessments or leadership styles. It is about letting go of who you think you are supposed to be, and gaining the clarity to become who you are meant to be. Because before you can lead others with confidence, you have to understand the person doing the leading.   Resources Mentioned • The CARES Framework Toolkit: Explore all five elements of the CARES Framework and download the toolkit: https://www.thekindleaderpodcast.com/cares-framework/ • The Kind Leader Newsletter: Subscribe for new episodes, leadership insights, and practical resources: https://www.thekindleaderpodcast.com/ • Predictive Index Behavioral Assessment: A behavioral assessment designed to help individuals understand their natural strengths, working style, and potential blind spots. https://www.predictiveindex.com/assessments/behavioral-assessment/ • Myers-Briggs Type Indicator: A personality assessment that can provide additional language for understanding how you process information, make decisions, and interact with others. https://www.themyersbriggs.com/en-us/explore-solutions/mbti   Connect with The Kind Leader Podcast: Website: TheKindLeaderPodcast.com YouTube: Kind Leader Podcast Apple Podcasts: The Kind Leader Spotify: The Kind Leader Email: thekindleader@bravocg.com

    The CARES Framework: Clarity | Understand Yourself Before You Lead Others

  5. Jul 22

    The Kind Leader Rewind | After 17 Bosses, Someone Finally Listened.

    "You are my seventeenth boss." "Why should I care?" Those seven words became one of the most unforgettable leadership moments in the history of The Kind Leader Podcast. In this first Kind Leader Rewind, Gino Degregori revisits a powerful conversation with cybersecurity leader Haj Ramos, CIO and SVP at Ginnie Mae, and reflects on the story that helped shape the CARES Framework. After leading through more than three decades in cybersecurity, Haj discovered that transforming a team doesn't always start with strategy. Sometimes it starts with listening. Together, you'll revisit: Why great leaders lead by example, empathy, and empowerment The story of the employee who had stopped believing in leaders How one conversation completely changed a person's career Why people don't need another boss, they need someone who genuinely cares The connection between listening and psychological safety How creating trust unlocks hidden potential Why feeling seen changes the way people lead and contribute How this story inspired part of the CARES Framework This conversation goes far beyond revisiting a past episode. It's about remembering that leadership isn't measured by how many people report to you. It's measured by how many people feel heard because of you. Because sometimes the most powerful thing a leader can do… …is simply listen.   Resources Mentioned: Original Episode: Episode 74 — Kind Leadership Under Pressure: Russell "Haj" Ramos on Trust, Security & Human-Centered Technology The CARES Framework Toolkit: Explore the five traits at the heart of kind leadership and download the toolkit: ⁠thekindleaderpodcast.com/cares-framework The Kind Leader Newsletter: Get leadership insights, new episodes, and resources delivered to your inbox: thekindleaderpodcast.com   Connect with The Kind Leader Podcast: Website: TheKindLeaderPodcast.com YouTube: Kind Leader Podcast Apple Podcasts: The Kind Leader Spotify: The Kind Leader Email: thekindleader@bravocg.com

    The Kind Leader Rewind | After 17 Bosses, Someone Finally Listened.

  6. Jul 8

    Why Great Leaders Make People Stay

    In a world where changing jobs every few years has become the norm, Michael Roop made a different choice. He stayed. For more than 22 years. Not because change wasn't possible. But because every great leader he followed gave him another reason to stay. In this special 100th episode of The Kind Leader Podcast, Gino Degregori sits down with Michael Roop, Managing Director at Accenture Federal Services, to explore why people don't stay because of policies, perks, or paychecks. They stay because someone keeps investing in them. Together, Gino and Mike explore: • Why psychological safety builds lasting teams • How consistency creates trust during uncertainty • Why people follow leaders, not companies • The role mentors play in long-term career growth • How great leaders respond when everything changes • Why strong relationships outperform constant job-hopping • How intentional culture shapes retention • Why leaders must be kind to themselves before leading others well This conversation goes far beyond career longevity. It's about understanding why some leaders inspire people to stay, grow, and give their best year after year. Because great leaders don't just build successful teams. They build places people never want to leave.     Connect with Michael Roop LinkedIn: Michael Roop Connect with The Kind Leader Podcast: Website: TheKindLeaderPodcast.com YouTube: Kind Leader Podcast Apple Podcasts: The Kind Leader Spotify: The Kind Leader Email: thekindleader@bravocg.com

    Why Great Leaders Make People Stay

  7. Jul 1

    The Hidden Cost Of Employees Feeling Unseen

    60% of employees feel unnoticed by their manager. Most leaders think that's an engagement problem. Sally Mildren believes it's a biological one. In this powerful episode of The Kind Leader Podcast, Gino Degregori sits down with marketing strategist, leadership educator, and author Sally Mildren to explore why feeling seen isn't just good leadership, it's a fundamental human need. Drawing from neuroscience, healthcare leadership, and decades of executive experience, Sally explains why our brains are wired for connection, how loneliness quietly impacts performance, and why leaders who create psychological safety unlock stronger, healthier teams. Together, Gino and Sally explore: Why feeling unseen activates the brain's threat response How human connection improves trust, collaboration, and performance Why clarity is one of the greatest acts of kindness a leader can offer The critical role middle managers play in shaping culture Why psychological safety drives better leadership How curiosity helps leaders uncover what motivates people Why communication matters more than generational differences The biological reason employees need to feel seen and valued This conversation goes far beyond employee engagement. It's about understanding that people don't thrive because they're managed. They thrive because they feel seen. Because connection isn't a leadership luxury. It's part of how we're wired.   Connect with Sally Mildren: LinkedIn: Sally Mildren Common Well Marketing: commonwellmarketing.com The Leadership Cafe: theleadershipcafe.com   Resources Mentioned: Leading Real People: A Guide to Human-Centric Leadership for Today's New and Middle Managers by Sally Mildren Work and Love  by Marcus Buckingham   Connect with The Kind Leader Podcast: Website: TheKindLeaderPodcast.com YouTube: Kind Leader Podcast Apple Podcasts: The Kind Leader Spotify: The Kind Leader Email: thekindleader@bravocg.com

    The Hidden Cost Of Employees Feeling Unseen

  8. Jun 24

    The CARES Framework: 5 Traits Every Kind Leader Shares

    After 97 conversations with leaders from around the world, Gino Degregori noticed a pattern: The leaders people trust most don't just excel at one thing. They consistently get five things right. The challenge? Most leaders only master one or two. In this solo episode of The Kind Leader Podcast, Gino introduces the CARES Framework, a leadership model built from nearly 100 conversations exploring what kindness truly looks like in practice. Together, you'll explore: • Why leadership starts with clarity before strategy • How accountability and kindness can coexist • Why trust is built long before you need it • The difference between real empathy and performative empathy • Why service is the foundation of leadership • The hidden cost of leading from power instead of purpose • The five traits that consistently appear in kind leaders This conversation goes far beyond leadership theory. It's about understanding which leadership habits you're already practicing and which ones may be quietly holding you back. Because great leaders aren't defined by what they achieve. They're remembered for how they impact the people around them.   Connect with The Kind Leader Podcast: Website: TheKindLeaderPodcast.com YouTube: Kind Leader Podcast Apple Podcasts: The Kind Leader Spotify: The Kind Leader Email: thekindleader@bravocg.com

    The CARES Framework: 5 Traits Every Kind Leader Shares
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Ratings & Reviews

4.4
out of 5
7 Ratings

About

Navigating Business with Empathy! This podcast is to inspire and equip current and aspiring business leaders to incorporate kindness and empathy into their leadership styles. By presenting real-world examples, interviews with thought leaders, and actionable strategies, the podcast aims to shift the paradigm of leadership from merely transactional to more compassionate and ethical, but most importantly transformational. We want to also serve as a platform to encourage strong, kind leadership that not only enhances corporate performance but also makes a generational impact by transforming organizational cultures for the better. The target audience includes corporate executives, managers, small business owners, and tech leaders who are interested in nurturing more humane, sustainable work environments while driving business success.

Information

  • Creator
    Gino Degregori
  • Years Active
    2023 - 2026
  • Episodes
    106
  • Rating
    Clean
  • Copyright
    © 2023
  • Show Website
    The Kind Leader