Deep Leadership

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.

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.

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.

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.

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.