Afghanistan’s: We Met the Deadline. We Failed the Mission

What happens when measurable goals create the illusion of success while the bigger mission fails?In this episode of Commander's Intent, retired Air Force Colonel and fighter pilot Derek Oaks shares powerful leadership lessons from Afghanistan and the 2021 U.S. withdrawal.Drawing from his military experience, Derek and Rob explore why clear vision, strategic planning, and effective leadership matter more than simply achieving measurable goals.Discover how unclear objectives can undermine an entire mission, why leaders must balance short-term results with long-term vision, and how accountability, honest evaluation, and learning from failure create stronger teams.From military operations to business leadership, this episode reveals how Commander's Intent helps leaders communicate purpose, make better decisions, and guide their teams through uncertainty.Great leadership isn't just about reaching goals. It's about knowing why those goals matter.

Are we teaching the next generation how to think, or simply teaching them what to think?In this episode of Commander's Intent, host Derek Oaks, retired Air Force colonel, fighter pilot, and leadership mentor, welcomes Marshall Carter, Head of School at Atrium School in Massachusetts, for a powerful conversation about developing confident, independent decision makers and future leaders.Marshall shares how critical thinking, problem solving, resilience, and learning through failure help young people develop the confidence to make decisions, overcome challenges, and discover their own paths in life.Explore why traditional education often emphasizes getting the right answers instead of encouraging creativity, curiosity, and independent thinking. Discover how experiential learning, healthy risk taking, and intrinsic motivation prepare students for real world challenges.Derek and Marshall also discuss the importance of parental involvement, educational leadership, emotional intelligence, and building trust between parents, teachers, and school administrators.Whether you're a parent, educator, executive, or leadership coach, this episode offers valuable insights into developing the next generation of confident thinkers, compassionate problem solvers, and effective leaders.Great leadership isn't about making every decision for someone. It's about preparing them to make great decisions without you.

When making tough leadership decisions, should you trust the facts or protect people's feelings?In this episode of Commander's Intent, retired Air Force Colonel and fighter pilot Derek Oakes shares a powerful lesson from his military aviation career about leadership, accountability, and accepting difficult feedback.Through an unforgettable fighter pilot training experience, Derek reveals why great leaders must put facts before ego, embrace constructive criticism, and use honest debriefs to improve performance.Discover how to overcome defensiveness, build a culture of accountability, make better decisions, and turn uncomfortable feedback into measurable growth.Because exceptional leadership isn't about always being right. It's about being willing to get better.Listen now and discover how truth, humility, and accountability can transform your leadership and drive better results.

What does it take to make the right decision when the pressure is on and everyone is watching?In this episode of Commander's Intent, host Derek Oaks, retired Air Force Colonel and fighter pilot, welcomes Steve Young, NFL Hall of Fame quarterback, Super Bowl champion, and two-time NFL MVP, for a powerful conversation about leadership, preparation, accountability, and making decisions in high-stakes environments.Drawing parallels between the NFL quarterback's pocket and the fighter pilot's cockpit, Steve reveals how elite performers develop the mental clarity, confidence, and instinct to make critical decisions when information is incomplete and the clock is running out.Together, they explore how relentless preparation creates faster decision-making, why great leaders take responsibility when things go wrong, and how trust, vulnerability, and shared purpose transform talented individuals into championship teams.Steve also shares lessons from playing under legendary coach Bill Walsh, the importance of learning from failure, and how the principles that helped him succeed on the football field continue to shape his business decisions, relationships, and family life.Because winning isn't just about talent. It's about preparation, accountability, trust, and the courage to lead when everything is on the line.Listen now and discover how to make better decisions under pressure, build stronger teams, and lead with confidence when it matters most.

What if the biggest threat to your organization's success isn't your competition, but how you treat your people?In this episode of Commander's Intent, host Derek Oaks, retired Air Force colonel and fighter pilot, explores why the Golden Rule remains one of the most powerful and overlooked principles of effective leadership.Through military history, real-world business examples, and personal leadership experiences, Derek and Rob discuss how respect, accountability, and fairness build trust, strengthen teams, and create lasting organizational success.Discover why employees stop speaking up, innovation disappears, and top performers leave when leaders fail to put people first.Because great leadership isn't measured by rank, title, or authority. It's measured by the trust you earn and how you treat the people you lead.

Is an MBA worth the time, money, and investment, or is real-world experience the better business education?In this episode of Commander’s Intent, Derek Oaks and Rob examine both sides of the MBA debate. An MBA can provide valuable knowledge in strategy, finance, operations, marketing, and business decision-making, but can a classroom really teach judgment, courage, culture, and leadership under pressure?They explore the dangers of analysis paralysis, relying too heavily on frameworks and data, short-term financial thinking, and having confidence without the real-world “scar tissue” that comes from making difficult decisions when the outcome actually matters.But this isn't an argument against education. Derek and Rob explain why an MBA can become a powerful amplifier when combined with technical expertise, leadership experience, and real responsibility.The real question isn't simply, “Should I get an MBA?” It’s “What do I need an MBA to do for me, and what leadership skills will I still need to learn somewhere else?”

As AI becomes more powerful, will technology eventually replace the value of human networks, relationships, and experience?In this episode of Commander’s Intent, Derek Oaks sits down with Judd Borakove, a six-time C-suite executive, three-time exit leader, growth advisor, and co-founder of Talent Fueled, to explore why human connection may become even more valuable in an AI-driven world.Judd explains why AI can provide information, but it cannot fully replace the experience, judgment, trust, and insights that emerge when people come together to solve real problems. AI is only as useful as the data behind it, and some of the most valuable knowledge inside an organization never makes it into a database, document, or algorithm.The conversation goes deeper into trust, collaboration, leadership, organizational alignment, and execution. Derek and Judd discuss why departments often operate in silos, how misaligned goals create friction, and why leaders need to build environments where people feel safe sharing what they really know. They also examine when collaboration becomes a strength and when too much collaboration can actually slow down decision-making.Ultimately, this episode makes the case that the future of leadership isn’t simply about having better technology. It’s about building better human systems around it. Because in a world overflowing with AI-generated information, trust, relationships, experience, and genuine human connection may become some of our most valuable competitive advantages.

A packed schedule can make you feel productive, but are the things filling your day actually moving you toward your vision?In this episode of Commander’s Intent, Derek Oaks and Rob Powell use a lesson from their military aviation careers, “cube out before you gross out,” to reveal what happens when leaders fill their time, teams, and organizations with tasks before prioritizing what matters most. They connect this aviation principle to the Eisenhower Matrix, leadership, time management, decision-making, and the danger of allowing other people to continually load your schedule. The challenge is simple: stop measuring productivity by how full your calendar is and start giving the weightiest matters your time first. Because being busy and moving forward are not the same thing. 

Can changing your words change the way you lead?In this episode of Commander’s Intent, Derek Oaks sits down with speaker, author, leadership consultant, and podcaster Becky Kemp to explore the power of language in leadership.They discuss how our thoughts and words influence emotions, actions, decision-making, and results, and why great leadership begins with learning to lead yourself. Becky shares practical strategies for shifting from anger and frustration to curiosity, focusing on solutions instead of problems, and pausing before reacting.Discover how becoming more intentional with your language can strengthen your mindset, improve leadership communication, and help you make better decisions when it matters most.Because words aren’t just something we say. They can become the compass that determines where we go.

What are you truly capable of, and how will you ever know if you never push yourself far enough to find out?In this episode of Commander’s Intent, retired Air Force Colonel and fighter pilot Derek Oaks shares the remarkable story of WWII fighter pilot JM Taylor, a member of the legendary Flying Tigers who survived being shot down, captured, and held as a prisoner of war.But it’s a story from Taylor’s pilot training that reveals an unforgettable lesson about pushing our limits. Determined to experience what it was like to fly from the front seat of a Stearman, Taylor climbed out of the cockpit at 5,000 feet, moved across the aircraft while it was flying, and discovered exactly how far he was willing to push himself.Derek explores the difference between recklessness and intentionally expanding your capabilities. Whether in leadership, business, flying, or everyday life, growth requires us to move beyond what we already know we can do.The question isn’t whether you should take unnecessary risks. It’s whether you’re continuing to challenge yourself, expand your comfort zone, and discover what you’re capable of becoming.