Deep Leadership

Why Self-Awareness Is the Leadership Skill Most Leaders Lack Most leaders don’t fail because they lack skill, experience, or good intentions—they fail because they don’t truly understand themselves. In this episode of Deep Leadership, I sit down with Margaret Andrews, author of Manage Yourself to Lead Others, to unpack why self-awareness is the foundation of effective leadership—and why so many leaders struggle without it. We talk about the gap between intentions and behaviors, why leaders often feel misunderstood, and how a lack of self-awareness quietly erodes trust, communication, and performance. Margaret shares a practical framework to help you better understand who you are, what drives you, and how others actually experience you as a leader. If you’ve ever felt like your message isn’t landing, your team isn’t responding the way you expect, or you’re not leading at the level you know you can—this conversation will challenge you in the right way. In this episode, you’ll learn: Why good intentions aren’t enough in leadershipThe real reason leaders feel misunderstoodA simple framework to build self-awarenessHow to align your behavior with your leadership goalsWhy growth feels uncomfortable—and why that’s a good sign

Leadership Decisions You Can’t Afford to Get Wrong In this episode of Deep Leadership, I sit down with Dr. Linda Henman, advisor, author, and expert in high-stakes decision-making, to talk about the leadership decisions you simply can’t afford to get wrong. Most organizations are full of people who know how to execute. They run fast, deliver results, and get promoted. But when the stakes are high, execution isn’t enough. The real differentiator is knowing which decisions matter most—and getting them right under pressure. Drawing on her research into resilience—including studies of American POWs—and decades of advising C-suite leaders, Linda explains why great leadership starts long before the crisis hits. It’s about building the judgment, confidence, and clarity to make tough calls when there’s no playbook. We also dig into one of the biggest mistakes companies make: promoting high performers into roles that require strategic thinking—and the costly consequences that follow. If you’re a leader, entrepreneur, or aspiring executive, this conversation will challenge how you think about hiring, promotion, and decision-making at the highest levels. In this episode, we cover: Why resilience is a choice—not just “bouncing back”The difference between tactical performers and strategic thinkersHow to make decisions when the stakes are high and the path is unclearWhy most companies promote the wrong peopleThe role of values and integrity in tough leadership callsHow to hire and develop leaders who can actually think strategically

Most leaders don’t fail because they don’t care. They fail because no one ever taught them how to lead. In this episode of Deep Leadership, I sit down with Robert Heath Sr., a former Marine Corps officer, attorney, and leadership coach, to unpack one of the biggest traps leaders fall into—the need to be the fixer. If you’re the person everyone relies on to solve problems, this conversation might hit close to home. Because the truth is this: The skills that made you successful as an individual contributor are the exact skills that will hold you back as a leader. We dig into: Why high performers struggle when they step into leadership rolesThe hidden cost of “being the go-to person.”Why leadership is the opposite of getting things done yourselfHow to shift from problem solver to obstacle removerThe power of aligning purpose, identity, and daily actionsWhy miscommunication is quietly draining your team’s performanceHow to actually empower your team to step up and take ownership Robert shares hard-earned lessons from the military, education, and corporate world—and breaks down what it really takes to bring out the best in your people. If you’ve ever felt overwhelmed, frustrated with your team, or stuck carrying too much… this episode will give you a better way forward.

What happens when your best performer becomes your worst leader? In this episode of Deep Leadership, I sit down with Dr. Peter James, President and CEO of HCG Strategic Partners, to unpack one of the most common (and costly) mistakes organizations make: promoting great individual contributors into leadership roles without preparing them to lead. Peter brings a rare perspective shaped by leadership in the military, corporate America, and higher education. Together, we break down why being great at your job doesn’t automatically make you a great leader—and what actually does. We dive into: Why top performers often struggle when they step into leadershipThe critical role of self-awareness in leading othersWhy most leaders don’t realize they’re failingThe importance of having someone who will hold you accountableHow organizations can better prepare people for leadership rolesWhat it takes to build a culture that can adapt and thrive in constant change If you’ve ever been promoted (or are about to be), this conversation will challenge how you think about leadership—and give you practical ways to get better.

Broken Trust: How Great Leaders Fix It Trust is at some of the lowest levels we’ve ever seen—and leaders are paying the price. In this episode, I sit down with Dr. Darryl Stickel to unpack what trust really is, why it’s collapsing in today’s uncertain world, and how great leaders rebuild it inside their teams. We talk about the real definition of trust (it’s not what you think), why confidence without certainty destroys credibility, and how leaders can create “pockets of excellence” even in broken organizations. If you’re leading in a time of uncertainty—and let’s be honest, we all are—this conversation will give you practical tools to build trust, strengthen your team, and become a leader worth following. In this episode, you’ll learn: Why trust is the foundation of every high-performing teamThe hidden reason trust is breaking down in organizations todayHow uncertainty and vulnerability shape every leadership decisionThe three drivers of trust: benevolence, integrity, and abilityHow to build trust even if your organization is strugglingSimple ways to show your team you “have their back” About Dr. Darryl Stickel: Dr. Darryl Stickel is a leading expert on trust and the author of Building Trust: Exceptional Leadership in an Uncertain World. He helps leaders and organizations understand how trust works—and how to build it when it matters most.