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Commander's Intent

Derek Oaks

Commander's Intent with Derek Oaks

When the pressure’s on, can you make the call? Commander's Intent helps leaders at every level make confident, timely decisions that drive real results. Hosted by Colonel (Ret.) Derek Oaks, former Air Force fighter pilot and leadership mentor, this podcast blends stories from combat and business to teach you how to lead with clarity, courage, and purpose. Learn to define your mission, empower your team, and execute with confidence.

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Yesterday · 45 min
Are We Teaching Kids to Think—or Just to Follow Directions? | Marshall Carter
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.
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October 29 · 12 min
Do I want Facts or Feelings When Trying to Win
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.
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October 22 · 53 min
How to Make Decisions Under the Microscope in a High Stakes Environment with Steve Young
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.
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October 15 · 31 min
Why Leaders Fail Without the Golden Rule
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.
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October 8 · 44 min
Is an MBA Really Worth It?
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?”
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October 1 · 45 min
Can AI Replace the Value of Networks with Judd Borakove
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.
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September 24 · 25 min
Are You Busy or Are You Actually Moving Forward?
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.
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September 17 · 42 min
Why Does Language Matter So Much in Leadership with Becky Kemp
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.
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September 10 · 12 min
How Far Are You Willing to Push Yourself?
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.
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September 3 · 25 min
Maverick or Iceman: Who Do You Want on Your Team?
Would you rather have Maverick or Iceman on your team? In this episode of Commander’s Intent, retired Air Force Colonel and fighter pilot Derek Oaks and co-host Rob Powell explore one of leadership’s toughest challenges: balancing dependable rule followers with innovative thinkers who challenge the status quo. Discover why great organizations need both, how to recognize a true Maverick from a troublemaker, and how strong leaders put the right people in the right roles to drive innovation without creating chaos.
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August 27 · 45 min
Is Confidence Overrated? What Great Leaders Should Build Instead with Heather Jo Kennedy
Is confidence really the secret to great leadership, or are we spending too much time chasing something that should be the result of other things? In this episode of Commander’s Intent, Derek Oaks sits down with author, speaker, consultant, and productivity expert Heather Jo Kennedy to challenge conventional thinking about confidence. Heather argues that confidence is valuable, but often a byproduct of things we have greater control over, including growth, balance, tenacity, clarity, and support. They explore why identity is the bedrock of impact, how knowing your values and strengths can help you understand who you really are, and why your occupation doesn’t have to define your identity. Heather also introduces a powerful framework for building the right support system: everyone needs a coach, a teammate, and fans. Knowing which role you need from someone, and which role you should play for others, can transform leadership, teamwork, and personal relationships. The takeaway: Don’t chase confidence. Build clarity, know who you are, surround yourself with the right people, and take action. Confidence will follow. Connect with Heather Jo Kennedy: Website: https://www.hjkennedy.com
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August 20 · 21 min
Who Is Garcia and Why Does His Message Still Matter to Leaders?
What does a leadership essay written in 1899 have to teach today’s leaders? In this episode of Commander’s Intent, Derek Oaks and Rob Bau unpack A Message to Garcia, the famous essay written by Elbert Hubbard in 1899 about personal initiative, duty, reliability, and getting the job done. The story follows Lieutenant Andrew Rowan, who was tasked with delivering an important message to Cuban rebel leader General García during the Spanish-American War. At its core, the essay highlights three powerful themes: initiative, doing what needs to be done without constant supervision; action over excuses, moving forward instead of complaining or waiting for step-by-step direction; and reliability, becoming someone others can trust to complete a difficult mission. But Derek and Rob take the conversation further. Instead of simply demanding more initiative from your people, leaders need to ask whether they’ve created an environment where initiative can thrive. Are you giving your team the authority, responsibility, resources, trust, and clarity they need to succeed? They explore how micromanagement can destroy initiative, why confidence and trust must flow both ways, and why leaders should examine their own role before blaming employees for poor performance. The takeaway: Don’t just ask how you can find more Lieutenant Rowans. Ask what kind of leader and culture will help create them. You can read the full text of A Message to Garcia through Project Gutenberg.
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August 13 · 44 min
How to Lead When the Budget Changes but the Mission Doesn’t with Max J. Stitzer
How do you lead a team when budgets change, contracts disappear, or rapid growth forces you to rethink who does what? In this episode of Commander’s Intent, Derek Oaks sits down with retired U.S. Air Force Brigadier General Max J. Stitze to discuss how leaders can build, grow, and even shrink teams without destroying trust and culture. Drawing from nearly four decades of military leadership, Max shares lessons on recognizing individual strengths, putting people in the right roles, and creating teams where everyone has the opportunity to perform at their highest level. They also tackle one of leadership’s hardest realities: layoffs. Max explains why leaders must consider both the financial cost and the human cost of workforce decisions, and why empathy, communication, and loyalty matter even when difficult cuts are unavoidable. Whether your organization is growing, contracting, or navigating an uncertain market, this episode offers practical leadership lessons for building the right team, adapting to change, and treating people like valued teammates rather than numbers on a spreadsheet.
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August 6 · 43 min
Why Great Leaders Ask for Input Instead of Having All the Answers: Lessons from a U.S. Navy Attack Submarine Commander with William Spears
What can business leaders learn from commanding a U.S. Navy attack submarine? In this episode of Commander's Intent, retired Air Force Colonel Derek Oaks sits down with Commander William Spears, a career submariner and U.S. Navy officer, to explore the leadership principles that apply whether you're commanding a nuclear-powered submarine or leading a corporate team. Drawing from decades of experience, Commander Spears explains why technical competence earns trust, why the best leaders invite feedback instead of pretending to have all the answers, and how creating team ownership leads to better decisions under pressure. Together, they discuss the importance of empowering people at every level, encouraging team members to challenge decisions when necessary, and building cultures where communication flows both up and down the chain of command. Commander Spears shares why asking for recommendations creates stronger buy in, how repeating key priorities ensures alignment, and why face-to-face communication is often far more effective than relying on email alone. The conversation also explores decision-making under pressure, explaining why leaders must distinguish between true emergencies and situations that simply feel urgent. Derek and William discuss how slowing down when possible often leads to better outcomes, stronger performance, and healthier organizations while avoiding the burnout that comes from treating every challenge like a crisis. Finally, they highlight the often overlooked role of military families, the importance of trust, and the responsibility leaders have to care for the people behind the mission. Whether you're leading a military unit, a Fortune 500 company, a small business, or a growing team, this episode offers practical leadership lessons on trust, accountability, communication, and building high-performing organizations where everyone understands the mission and feels responsible for its success.
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July 30 · 32 min
AI Won't Replace Leaders... But It Will Replace the Unprepared with Richard Webb
Will artificial intelligence replace your job... or make you dramatically better at it? In this timely episode of Commander's Intent, retired Air Force Colonel Derek Oaks and co-host Rob sit down with software developer, AI strategist, author, and entrepreneur Richard Webb to explore one of the biggest leadership questions of our time: How do we survive and thrive in the age of AI? Rather than focusing on fear and hype, they examine how leaders, entrepreneurs, and professionals can use AI as a strategic partner while preserving the uniquely human qualities that technology can never replace. Drawing on more than 35 years of software development experience, Richard shares why he transitioned from digital marketing into AI automation and explains how businesses are using AI to eliminate bottlenecks, improve productivity, automate repetitive tasks, and create faster, smarter workflows. He makes the case that the greatest opportunities with AI aren't replacing people, but empowering them to accomplish more with the time they already have. The conversation goes beyond technology into leadership and decision-making. Richard explains why AI should be viewed as a trusted thinking partner, not the decision-maker, and demonstrates how leaders can personalize AI tools to challenge assumptions, remove emotional bias, clarify priorities, and improve strategic thinking. Derek and Rob explore how human judgment, ethics, accountability, and emotional intelligence remain essential in a world increasingly influenced by artificial intelligence. Together, they tackle difficult questions about the future of work, self-driving vehicles, legal accountability, healthcare, investing, automation, and the changing job market. They discuss which careers are most vulnerable to AI, why skilled trades and human-centered leadership remain invaluable, and how organizations can prepare for a future where AI becomes a permanent part of everyday business operations. Most importantly, this episode reminds us that while AI can accelerate productivity, analyze data, and automate routine work, it cannot replace meaningful relationships, ethical leadership, authentic human connection, or the wisdom that comes from lived experience. The future belongs to leaders who learn to combine the best of artificial intelligence with the irreplaceable strengths of human intelligence. Whether you're a business owner, executive, entrepreneur, military leader, or simply curious about what AI means for your career, this conversation offers practical insights to help you lead with confidence through one of the greatest technological shifts in history.
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July 23 · 50 min
How Great Leaders Thrive in Challenging Situations with Theresa Carpenter
How do exceptional leaders make the right decisions when the pressure is high, the path isn't clear, and the stakes couldn't be greater? In this episode of Commander's Intent, retired Air Force Colonel Derek Oaks and co-host Rob Powell welcome retired Navy Commander and Stories of Service host Theresa Carpenter for an insightful conversation on leading through uncertainty, conflict, and organizational complexity. Drawing on decades of military leadership, international operations, public affairs, and real-world experience, Theresa shares practical lessons on navigating challenging environments while staying true to your values. Together, they discuss how to remove barriers that prevent teams from succeeding, why healthy disagreement creates stronger leaders, the importance of setting boundaries, building trust, owning mistakes, encouraging honest feedback, and creating a culture where people can challenge ideas without attacking people. They also explore the realities of leadership in the military, business, and everyday life, proving that great leadership isn't about having all the answers. It's about staying adaptable, remaining open to new perspectives, and never losing sight of the mission. Whether you're leading a company, a team, your family, or simply yourself, this episode offers practical strategies to help you make better decisions, solve difficult problems, and lead with greater clarity, courage, and purpose.
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July 16 · 45 min
Innovating in Aviation: How Michael Duke Is Redefining What's Possible
How do you innovate in an industry where every decision is scrutinized, every regulation matters, and failure simply isn't an option? In this fascinating episode of Commander's Intent, retired Air Force Colonel Derek Oaks and co-host Rob Powell sit down with Michael Duke, Founder and CEO of DBT Aero, to explore what it really takes to bring groundbreaking innovation to one of the world's most highly regulated industries. Michael shares the remarkable story behind DBT Aero's revolutionary double box tail aircraft design, an innovation that dramatically improves aerodynamic efficiency, reduces fuel consumption, lowers operating costs, and has the potential to transform regional aviation. But creating breakthrough technology is only part of the challenge. Success also requires navigating complex FAA certification, earning investor confidence, building world-class teams, and balancing bold innovation with uncompromising safety. Together, they discuss why great leaders must embrace calculated risk, how regulation can become a catalyst instead of a barrier, the role artificial intelligence is playing in next-generation aircraft design, and why assembling the right team is often the greatest competitive advantage. They also examine the future of regional aviation, sustainable transportation, and what it takes to lead transformational change in industries where trust, precision, and execution are everything. Whether you're leading a startup, scaling a company, managing innovation inside a large organization, or simply fascinated by the future of aviation, this conversation offers powerful lessons on leadership, perseverance, innovation, and making courageous decisions when the path forward has never been traveled before. Because breakthrough innovation isn't about ignoring the rules. It's about having the vision to redefine what's possible while earning the trust to bring others with you.
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July 9 · 41 min
The Decision-Making Principles That Made America Different
What makes America truly exceptional, and what can today's leaders learn from the principles that shaped a nation? In this thought-provoking episode of Commander's Intent, retired Air Force Colonel Derek Oaks and Rob explore the origins of American Exceptionalism and why its foundational ideas remain essential for effective leadership and decision-making. From the Declaration of Independence and the Constitution to individual liberty, limited government, personal responsibility, and the rule of law, they examine the timeless principles that have driven innovation, prosperity, and organizational success for nearly 250 years. Whether you're leading a business, a team, or your own life, you'll discover why great leadership begins with empowering individuals, protecting freedom, embracing accountability, and creating organizations built on trust, purpose, and shared values. This conversation offers practical leadership insights rooted in history while challenging leaders to think beyond politics and focus on the enduring principles that produce exceptional results. If you're ready to strengthen your leadership, make better decisions, and better understand the ideas that continue to influence organizations and nations around the world, this episode is one you won't want to miss.
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July 2 · 42 min
Gaming, Strategy, and the Future of Leadership with Gayle Dickie
What if the world's greatest leadership training ground isn't found in the boardroom but inside the gaming industry? In this fascinating episode of Commander's Intent, Derek Oaks sits down with global media strategist and gaming industry expert Gayle Dickie to explore how gaming has evolved into one of the world's most powerful ecosystems for leadership, strategy, innovation, and decision-making. Gayle shares why gaming is no longer simply entertainment. It is a global economic force where millions of people develop critical thinking, risk assessment, collaboration, communication, and leadership skills every day. Together, they discuss how business leaders can learn from gaming communities, why community has become the new competitive advantage, and how successful organizations build trust before they build products. The conversation also explores leadership, investor pitching, innovation, AI, the future of media, empowering women in technology, and why understanding human behavior is becoming the most valuable business skill of all. If you're a leader, entrepreneur, investor, educator, or simply curious about where business and technology are heading, this episode offers a fresh perspective on one of the fastest-growing industries in the world and the leadership lessons it has to teach us.
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June 25 · 29 min
The Power of Human Connection with Jason Wright
What if one simple conversation could change someone's life? In this inspiring episode of Commander's Intent, retired Air Force Colonel Derek Oaks sits down with bestselling author Jason Wright to explore the profound impact of human connection, empathy, and intentional leadership. Drawing from years of traveling, writing, and meeting strangers from all walks of life, Jason shares powerful stories about seeing people beyond their circumstances, learning the value of listening, and recognizing the dignity that exists in every individual. Together, Derek and Jason discuss leadership, compassion, resilience, childhood influences, and why some of the most important moments in life happen when we simply slow down and acknowledge another human being. Whether you're leading a team, building a business, raising a family, or simply trying to make a positive difference in the world, this conversation will challenge you to look beyond labels, assumptions, and first impressions. Because sometimes the greatest act of leadership is making someone feel seen.
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