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The Kind Leader
The Kind Leader
Author: Gino Degregori
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© 2023
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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.
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.
109 Episodes
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A plane rarely gets into trouble because of one enormous mistake. It starts with the small ones. A checklist skipped. A warning ignored. A deviation that worked out fine last time, so you allow it again. Aviation calls it "normalization of deviation." And businesses do it every day. In this episode of The Kind Leader Podcast, Gino Degregori sits down with Gabe Muller, EOS Implementer, entrepreneur, community builder, and fellow pilot, to explore what the cockpit can teach leaders about running a company. Gabe explains how the small deviations leaders tolerate today can quietly become the standards their organizations live by tomorrow. And by the time the consequences become obvious, the damage may already be underway. Gino also shares a vulnerable moment from the cockpit when, during a difficult landing, he heard himself say three times, "I should go around." He didn't. What happened next became a powerful reminder of what can happen when confidence, preparation, and judgment stop working together. Together, Gino and Gabe explore: • What aviation can teach leaders about running a business • How small deviations quietly become dangerous standards • Why relying on gut instinct can eventually become a liability • Why leadership growth must keep pace with company growth • How high performers can quietly destroy a culture • Why trust is the foundation for healthy conflict and accountability This conversation goes far beyond aviation or operating systems. It's about the standards you allow when nobody thinks the consequences are serious yet. Because the most dangerous leadership mistakes rarely begin as big ones. They begin as small deviations you decided were okay. Connect with Gabe Muller EOS Implementer Profile: Gabe Muller - EOS Worldwide Smokehouse Pilots: smokehousepilots.com Connect with Gabe: Gabe Muller - Linktree Resources The CARES Framework ToolkitExplore the five traits of kind leadership and download the toolkit: thekindleaderpodcast.com/cares-framework/ The Kind Leader NewsletterGet 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: [email protected] Chapters 00:00 What Aviation Can Teach Us About Leadership 00:32 Meet Gabe Muller: Pilot & EOS Implementer 01:28 Why Clarity Is an Act of Kindness 06:07 The Difficult Feedback That Changed Gabe's Career 09:54 What Being a Pilot Teaches You About Leadership 12:08 Leadership + Management = Accountability 14:17 The Small Deviations That Can Become Dangerous 17:27 Why Your Gut Isn't Enough to Run a Business 20:06 Your Leadership Has to Grow With Your Company 24:35 Can You Get Results Without Trust? 28:08 Why Your Mind Should Always Be Ahead of the Plane 32:24 Building a Community of 9,000+ Pilots 35:47 Gino Opens Up About Imposter Syndrome 40:48 Why Less Is More for Leaders
The kindest leaders aren't always the easiest leaders to work for. Sometimes, they're the ones who expect the most from you. In this second deep dive into the CARES Framework, Gino Degregori explores Accountability, the A in CARES, and why holding people to a high standard isn't the opposite of caring for them. It may be one of the clearest ways to show that you do. Gino also shares one of his own biggest leadership blind spots: believing good people would simply figure things out on their own. In trying to give people space, he sometimes avoided the very conversations that could have helped them grow. Because kindness without accountability creates chaos. Accountability without kindness creates fear. Kind leadership creates excellence. In this episode, Gino explores: • Why kindness and accountability must exist together • How avoiding hard conversations can become a leadership failure • Why accountability without the right setup turns into blame • The difference between doing accountability with someone and doing it to them • The Setup Test, With-or-To Test, and Repair Question • Why telling someone the truth can be one of the kindest things a leader does This conversation goes far beyond performance metrics or difficult feedback. It's about having enough care for someone to tell them the truth, and enough commitment to stay with them after you do. Because holding the standard doesn't require fear. It requires clarity, courage, and care. 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/ Previous CARES Deep Dive - Clarity: The CARES Framework: Clarity | Understand Yourself Before You Lead Others Connect with The Kind Leader Podcast: Website: TheKindLeaderPodcast.com YouTube: Kind Leader Podcast Apple Podcasts: The Kind Leader Spotify: The Kind Leader Email: [email protected] Chapters 00:00 Why Kind Leaders Still Need Accountability 02:05 When Kindness Without Accountability Creates Chaos 04:05 Why Accountability Has Been One of Gino's Biggest Challenges 06:46 How to Hold People Accountable Without Creating Fear 09:26 Accountability Is the Truth Delivered With Care 10:28 The 3 Tools for Kind Accountability 13:07 Accountability Doesn't End With the Hard Conversation 14:24 Putting the Accountability Tools Into Practice 15:17 Who Are You Protecting From the Truth? 15:58 What's Next in the CARES Framework
You have about three seconds to earn someone's attention. Hollywood understands this. Most leaders don't. In this episode of The Kind Leader Podcast, Gino Degregori sits down with Brandon Wasserburger, founder and CEO of Fire Tribe, who spent years producing and editing shows for Netflix and HGTV before building a marketing agency and team-first culture of his own. After working alongside some of the best producers in the entertainment industry, Brandon discovered that the principles Hollywood uses to capture an audience can teach leaders something surprisingly powerful: Before people listen to you, they need to feel that you see them. And just like an audience can tune out in seconds, so can your team. Together, Gino and Brandon explore: What Hollywood can teach leaders about earning attention Why the first three seconds of an interaction matter How to make people feel seen before asking them to listen Why kind leadership requires both compassion and high standards How psychological safety changes the way teams communicate Why Brandon puts his team first when client relationships get difficult How storytelling and emotion influence the way people receive a message Why leaders should talk less, listen more, and pay attention to what makes their teams tune out This conversation goes far beyond storytelling. It's about understanding that attention isn't something a title gives you. It's something your leadership has to earn. Because Hollywood has spent decades learning how to make people lean in. Maybe it's time leaders did the same. Connect with Brandon Wasserburger Website: firetribe.tv LinkedIn: Brandon Wasserburger Resources The CARES Framework ToolkitExplore the five traits of kind leadership and download the toolkit: thekindleaderpodcast.com/cares-framework/ The Kind Leader NewsletterGet 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: [email protected] Chapters 00:00 Why Great Leaders Start by Building Real Connection 00:35 From Television to Leadership: Brandon's Journey 02:58 What Kind Leadership Really Means 06:06 The Leader Who Changed Brandon's Career 08:01 Why Authenticity Builds Stronger Teams 12:04 The Secret to Handling Difficult Clients 14:11 Why the Hardest Projects Create the Best Leaders 22:55 What Hollywood Can Teach Every Leader 37:21 Using Storytelling to Make Safety Matter 43:43 Rapid Fire Questions
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: [email protected] 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
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: [email protected]








