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Deep Leadership: Daily Summaries Delivered
by Jon S. Rennie
“Leadership is a People Business.” That's the philosophy of this leadership podcast from Jon Rennie. It's real-world, actionable advice from Jon as well as his expert guests. As a former Cold War Submarine Officer who spent 22 years leading businesses in Corporate America before starting his own manufacturing business, he knows that leadership matters!
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- Yesterday42 min
#0453 – Stop Planning. Start Thinking Strategically with Charlie Curson
Strategy is not planning. And being busy doesn’t necessarily mean you’re being strategic. In this episode of the Deep Leadership podcast, I’m joined by Charlie Curson, founder of Mandarin and author of the international bestselling book Be More Strategic. Charlie has spent more than 25 years helping leaders around the world develop their ability to think strategically and make better decisions in complex environments. We discuss why so many leaders confuse strategy with planning, why operationally strong leaders can struggle when they move into strategic roles, and how strategic thinking is a capability that can be deliberately developed and practiced. Charlie also explains why strategy requires making difficult choices, how pressure causes leaders to fall back into operational habits, and why listening, self-awareness, curiosity, and comfort with uncertainty are essential skills for strategic leaders. In this episode, we discuss: • The difference between strategy and planning• Why strategy must come before planning and execution• Why leaders become trapped in operational thinking• How to develop strategic thinking as a leadership capability• Why strategy requires deciding what not to do• How short-term pressure can pull leaders away from strategy• The importance of self-awareness and open-mindedness• Why better listening leads to better strategic decisions• How leaders can balance execution with long-term thinking• Simple practices you can use to become more strategic Charlie reminds us that strategic thinking isn’t something reserved for CEOs, consultants, or annual planning sessions. It is a leadership capability that can be learned, practiced, and strengthened over time. If you find yourself constantly reacting, solving the problem in front of you, and struggling to find time to think about where you’re actually going, this conversation is for you. Connect with Charlie Curson: Be More Strategic Book: https://amzn.to/4iW0x5p LinkedIn: https://www.linkedin.com/in/charliecurson/ Website: https://www.teammandarin.com/ Subscribe to Deep Leadership: If you enjoyed this episode, make sure to subscribe and share it with someone who wants to become a better leader. Sponsors: Cadre of Men Farrow Skin Care Salty Sailor Coffee Company Leader Connect The Qualified Leadership Series ____ Get all of Jon Rennie's bestselling leadership books for 15% off the regular price today! HERE Learn more about your ad choices. Visit megaphone.fm/adchoices
- 5 days ago37 min
#0452 – Why Your Business Should Run Better Without You with Joe Sandin
What if one of the best signs of leadership is that your business runs better when you’re not there? In this episode, I sit down with Joe Sandin, founder and CEO of Onsharp, a software company he started from his college dorm room more than 26 years ago. Joe built the company without outside investment, choosing to grow at his own pace while focusing on relationships, culture, and building a business designed to last. We talk about the difficult transition every entrepreneur eventually faces: moving from doing the work yourself to trusting other people to lead. Joe shares why founders have to learn to let go, allow people to make mistakes, stay focused, and sometimes simply get out of the way. We also explore how AI is changing the opportunities available to small businesses and why Joe believes technology should elevate people rather than replace them. In this episode, we discuss: • Why Joe chose to build his company without outside investors• The transition from doing everything yourself to developing leaders• Why delegation requires trust, patience, and allowing mistakes• How a founder can become the bottleneck in their own business• Why focus is critical as a company grows• The danger of constantly chasing new opportunities• How AI is changing software development and small business• Why patience may be one of the most important traits for entrepreneurs• What 26 years in business taught Joe about leadership and success If you’re an entrepreneur, business owner, or leader trying to build an organization that doesn’t depend on you for every decision, this conversation will give you plenty to think about. Listen in and learn why sometimes the best thing a leader can do is get out of the way. Connect with Joe Sandin: Website: https://www.onsharp.com/ Podcast: https://www.businessblueprintshow.com/ Instagram: https://www.instagram.com/mjcollectiondotcom/?hl=en Subscribe to Deep Leadership: If you enjoyed this episode, make sure to subscribe and share it with someone who wants to become a better leader. Sponsors: Cadre of Men Farrow Skin Care Salty Sailor Coffee Company Leader Connect The Qualified Leadership Series ____ Get all of Jon Rennie's bestselling leadership books for 15% off the regular price today! HERE Learn more about your ad choices. Visit megaphone.fm/adchoices
- 1 weeks ago38 min
#0451 – Hope Is Not a Strategy: How Leaders Prepare for the Unexpected with Alan Porter
Hope is not a strategy. In this episode of Deep Leadership, I sit down with Alan Porter, a retired U.S. Army Blackhawk instructor pilot, financial fiduciary, author, and founder of Strategic Wealth Strategies. Alan spent more than 21 years in the Army, where he learned that when the pressure is highest, you don’t rise to the occasion. You fall back on your preparation. Today, he applies that same philosophy to financial stewardship, risk management, and helping leaders prepare for the unexpected. We discuss: • What military aviation teaches us about leadership and preparation• Why leaders need to think about risk before a crisis occurs• The dangers of focusing on growth while ignoring protection• Why financial stewardship is a leadership responsibility• How unexpected life events can change everything• Why preparation, redundancy, and risk management matter in business and life• The importance of protecting your family, your business, and your legacy• Why “hope is not a strategy” Alan’s message is simple: Life rarely goes exactly as planned. Strong leaders prepare for what could go wrong before it does. If you’re a business owner, entrepreneur, or leader responsible for others, this conversation will challenge you to think differently about risk, preparation, and financial stewardship. Listen in and learn why the best time to prepare for the unexpected is before it happens. Connect with Alan Porter: Website: https://www.strategicwealthstrategies.com/ YouTube: https://www.youtube.com/@StrategicWealthStrategies Subscribe to Deep Leadership: If you enjoyed this episode, make sure to subscribe and share it with someone who wants to become a better leader. Sponsors: Cadre of Men Farrow Skin Care Salty Sailor Coffee Company Leader Connect The Qualified Leadership Series ____ Get all of Jon Rennie's bestselling leadership books for 15% off the regular price today! HERE Learn more about your ad choices. Visit megaphone.fm/adchoices
- 1 weeks ago40 min
#0450 – Why Modern Leaders Need Ancient Wisdom with Dr. Josh Herring
What if some of the best answers to today’s leadership challenges were written thousands of years ago? In this episode of the Deep Leadership podcast, I’m joined by Dr. Josh Herring, Director of the Logres Institute for Classical Liberal Studies, Curriculum Program Manager for the Rafiki Foundation, and author of Sons of Adam, Daughters of Eve: C.S. Lewis’s Images of Gender. Josh makes the case that modern education has increasingly emphasized skills and credentials while losing touch with the deeper intellectual traditions that once shaped leaders and critical thinkers. We discuss what leaders can learn from classical education, why studying history and literature matters, and how thinkers like Plutarch, Shakespeare, and Machiavelli can help us better understand leadership and human nature. We also explore why leaders need to explain the “why” behind their decisions, the importance of practicing leadership before the stakes are high, and why timeless truths may be more useful than chasing the latest leadership trends. If you want to think more deeply, make wiser decisions, and become a better leader, this conversation will challenge you to look backward in order to move forward. What You’ll Learn:• Why classical education matters for modern leaders• How ancient wisdom can improve leadership decision-making• Why knowledge, logic, and critical thinking still matter• What Plutarch, Shakespeare, and Machiavelli can teach us about leadership• Why leaders must clearly communicate the “why” behind their decisions• How timeless truths can help leaders navigate a rapidly changing world Listen now and discover why modern leaders may need ancient wisdom more than ever. Connect with Dr. Josh Herring : Website: https://www.logresinstitute.org/ Book: https://amzn.to/467eOVd LinkedIn: https://www.linkedin.com/in/joshua-herring-ph-d-1943a7119/ Twitter: https://x.com/TheOptimisticC3 Subscribe to Deep Leadership: If you enjoyed this episode, make sure to subscribe and share it with someone who wants to become a better leader. Sponsors: Cadre of Men Farrow Skin Care Salty Sailor Coffee Company Leader Connect The Qualified Leadership Series ____ Get all of Jon Rennie's bestselling leadership books for 15% off the regular price today! HERE Learn more about your ad choices. Visit megaphone.fm/adchoices
- 2 weeks ago38 min
#0449 – Too Many Ideas Are Killing Your Team with David Fung
Too many ideas can be just as dangerous as too few. In this episode of the Deep Leadership podcast, I talk with David Fung, a former senior director at Salesforce who spent more than 20 years in tech before founding Coachful Coaching. David has led high-performing teams through constant change, and today he helps leaders navigate transitions, build resilience, and lead with greater clarity. We discuss why one of the most important jobs of a leader is not generating more ideas, but filtering them before they reach the team. David explains how leaders can unintentionally overwhelm their people by constantly introducing new priorities, initiatives, and directions, especially in a world moving as quickly as ours. We also discuss: • Why leaders need to become better idea filters• David’s “Wait, Trade, Designate” approach to evaluating new ideas• Why being relatable can be more powerful than being impressive• What resilience really looks like during difficult transitions• How AI is creating an identity crisis for many leaders• Why leaders need to bring their people along during periods of rapid change• David’s “Name It, Frame It, Invite It” framework for communicating change• Why leading yourself well is the foundation for leading others Leadership isn’t about throwing every new idea at your team. It’s about knowing which ideas matter, which ones can wait, and how to keep your people focused on what matters most. If you want to lead with more clarity in a world of constant change, this conversation is for you. Connect with David Fung: LinkedIn: https://www.linkedin.com/in/davidfung2/ Website: https://coachfulcoaching.com/ Podcast: https://coachfulcoaching.com/podcast Subscribe to Deep Leadership: If you enjoyed this episode, make sure to subscribe and share it with someone who wants to become a better leader. Sponsors: Cadre of Men Farrow Skin Care Salty Sailor Coffee Company Leader Connect The Qualified Leadership Series ____ Get all of Jon Rennie's bestselling leadership books for 15% off the regular price today! HERE Learn more about your ad choices. Visit megaphone.fm/adchoices
- 2 weeks ago40 min
#0448 – The Decisions That Define You as a Leader with Dr. Fay Niewiadomski
What do your toughest decisions reveal about who you really are as a leader? In this episode of Deep Leadership, I talk with Dr. Fay Niewiadomski, international award-winning change management strategist, cultural transformation consultant, and author of Decisions That Matter. Fay has spent decades working with leaders, CEOs, board members, presidents, and government ministers around the world. We explore why leadership is ultimately revealed through the decisions we make, especially when our values are tested. Fay explains why leaders need to establish their boundaries before a crisis hits, what happens when personal and organizational values become misaligned, and why surrendering your power of choice can come at a tremendous cost. We also discuss the growing role of AI and why human judgment, wisdom, relationships, and communication will become even more important as technology advances. Fay makes a compelling case for using AI as a tool while never surrendering the uniquely human responsibility to think, judge, and decide for ourselves. In this episode, you’ll learn: • Why your most difficult decisions reveal your true values• How to establish your leadership boundaries before they are tested• Why compromising your values can slowly erode your identity• What happens when your values no longer align with your organization• Why leaders should never surrender their power of choice• What AI can and cannot replace in leadership• Why human judgment, wisdom, and relationships matter more than ever• How values create resilience when everything else is taken away Fay reminds us that leadership isn’t simply about the position we hold. It’s about the choices we make, the values we protect, and the decisions that ultimately define who we are. If you want to become a more intentional, values-driven leader, this conversation will give you plenty to think about. Connect with Dr. Fay Niewiadomski: LinkedIn: https://www.linkedin.com/in/fayniewiadomski/ Book: https://amzn.to/46s0Pt4 Subscribe to Deep Leadership: If you enjoyed this episode, make sure to subscribe and share it with someone who wants to become a better leader. Sponsors: Cadre of Men Farrow Skin Care Salty Sailor Coffee Company Leader Connect The Qualified Leadership Series ____ Get all of Jon Rennie's bestselling leadership books for 15% off the regular price today! HERE Learn more about your ad choices. Visit megaphone.fm/adchoices
- 3 weeks ago32 min
#0447 – Stop Avoiding Conflict: How to Handle Difficult Conversations with Dr. Irvine Nugent
Conflict is unavoidable in leadership. The question is whether you deal with it or let it grow. In this episode of the Deep Leadership podcast, I’m joined by Dr. Irvine Nugent, leadership and conflict management expert, keynote speaker, and co-founder of Conflict EQ. Growing up in Northern Ireland during the Troubles gave Irvin an early and deeply personal understanding of conflict, trust, and the consequences of unresolved tension. We discuss why leaders often avoid difficult conversations, how conflict can actually become a productive force, and why staying calm under pressure isn’t necessarily the same as being effective. Irvin also shares practical ways leaders can recognize their triggers, stay connected during tense conversations, and address conflict before it becomes destructive. We discuss: • Why leaders avoid difficult conversations• The difference between constructive and destructive conflict• Why unresolved conflict gets worse over time• What happens to leaders emotionally under pressure• Why staying calm isn’t enough• How to recognize your personal conflict triggers• How to prepare for difficult conversations• Why slowing down can prevent conflict from escalating• The importance of making people feel heard• Why leaders need to address conflict early Conflict is a normal part of leadership. Great leaders don’t pretend it isn’t there. They develop the capacity to work through it constructively and have the conversations that need to be had. If you’re a leader who has ever delayed a difficult conversation, struggled with conflict on your team, or wondered how to stay effective when tensions rise, this episode is for you. Listen now and learn how to stop avoiding conflict and start having the conversation. Connect with Dr. Irvine Nugent: LinkedIn: https://www.linkedin.com/in/irvinenugent/ Website: https://www.conflicteq.com/ Survey: https://conflicteq.scoreapp.com/ Subscribe to Deep Leadership: If you enjoyed this episode, make sure to subscribe and share it with someone who wants to become a better leader. Sponsors: Cadre of Men Farrow Skin Care Salty Sailor Coffee Company Leader Connect The Qualified Leadership Series ____ Get all of Jon Rennie's bestselling leadership books for 15% off the regular price today! HERE Learn more about your ad choices. Visit megaphone.fm/adchoices
- 3 weeks ago43 min
#0446 – Why Small Businesses Should Stop Acting Like Big Companies with Sri Kaza
What if the biggest mistake a small business can make is trying to operate like a big company? In this episode of the Deep Leadership podcast, I’m joined by Sri Kaza, seasoned business leader, former McKinsey advisor, entrepreneur, and author of Unconvention. After studying thousands of small businesses and examining which ones survived major disruptions, Sri discovered something surprising: the companies that endured weren’t necessarily following conventional business wisdom. They were doing things differently. Sri explains why small businesses have advantages that large corporations struggle to replicate, including close relationships with customers, a clear sense of purpose, and the ability to make fast, unconventional decisions. We also discuss why chasing growth can actually weaken a business, how knowing which customers not to pursue can make you stronger, and why resilience often comes from staying true to what makes your business unique. In this episode, we discuss: • Why small businesses shouldn’t try to operate like big corporations• What Sri learned from studying thousands of businesses during COVID• The three Ps of resilient businesses: positioning, proximity, and purpose• Why knowing your ideal customer is critical to long-term success• The danger of chasing growth at the expense of your identity• Why small businesses have a natural advantage in uncertain environments• How an underdog mindset helps entrepreneurs compete against larger companies• Why purpose and community can make a business more resilient• The customers your business should be willing to lose• Why leaders should role model their values instead of relying on policies Sri Kaza is the author of Unconvention, a book that challenges traditional corporate thinking and shows entrepreneurs how to build stronger, more resilient businesses by embracing what makes them different. Connect with Sri Kaza: Website: https://sri-kaza.com/ Book: https://amzn.to/3Ue2Ypx Subscribe to Deep Leadership: If you enjoyed this episode, make sure to subscribe and share it with someone who wants to become a better leader. Sponsors: Cadre of Men Farrow Skin Care Salty Sailor Coffee Company Leader Connect The Qualified Leadership Series ____ Get all of Jon Rennie's bestselling leadership books for 15% off the regular price today! HERE Learn more about your ad choices. Visit megaphone.fm/adchoices
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About Deep Leadership
“Leadership is a People Business.” That's the philosophy of this leadership podcast from Jon Rennie. It's real-world, actionable advice from Jon as well as his expert guests. As a former Cold War Submarine Officer who spent 22 years leading businesses in Corporate America before starting his own manufacturing business, he knows that leadership matters!
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