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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.
26 Episodes
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What separates high-performing teams from complete chaos—and why do even experienced leaders get it wrong? In this powerful episode of Commander’s Intent, Derek Oaks sits down with retired Colonel Jerry “Chewy” Cook to break down one of the most overlooked drivers of success in any organization: structure. Drawing from real-world combat search and rescue missions, leadership at the Pentagon, and executive experience in the civilian world, they reveal how misalignment between authority, ...
What separates great leaders from everyone else isn’t just experience—it’s how they think and act when the pressure is on. In this episode of Commander’s Intent, Derek Oaks sits down with Madeline Hart of Palantir to unpack how elite organizations use data, technology, and decisive leadership to move faster, think smarter, and stay ahead of the competition. From national security to business strategy, this conversation reveals why most systems fail, how true innovators break the rules, ...
What does it really take to step into a CEO role and lead when the stakes are high, and the answers aren’t clear? In this episode, Lt. Col. (Ret.) Mike Benitez, current CEO of Purple Rhombus, shares powerful insights from his first six weeks leading a venture-backed defense startup—revealing how to make critical decisions under pressure, build trust fast, and execute at scale in a rapidly evolving world. From fighter pilot discipline to redefining innovation in defense, this conversatio...
What if the biggest thing holding you back… is thinking “that’s not my job”? In this episode, we dive into the real difference between leaders and employees—and why growth happens when you step beyond your role, not stay inside it. Learn how great leaders think, how strong cultures are built, and why the willingness to figure it out (even when you’re not trained) is what separates average from exceptional. If you want to grow faster, lead better, and unlock your full potential, this episode w...
In this episode of Commander's Intent, retired Air Force Colonel and fighter pilot Derek Oaks explores how the Golden Rule—treating others the way you want to be treated—creates stronger leaders and more powerful teams. Derek explains why this timeless principle drives trust, loyalty, accountability, and high performance inside organizations—from the military to the business world. If you want to build a culture where people have each other’s backs, perform at their best, and stay committed t...
In this episode of Commander's Intent, retired Air Force Colonel and fighter pilot Derek Oaks explores the true meaning of integrity in leadership—and why it becomes most important when the pressure is highest. Through powerful real-life stories—from wartime courage to high-stakes decisions in aviation—Derek reveals how integrity shapes trust, culture, and decision-making inside organizations. If you want to become a leader people truly trust, this episode will challenge you to ask one critic...
In this episode, retired Air Force Colonel Derek Oaks, special operations veteran Dan Laguna shares raw, unforgettable stories of leadership under fire. From choosing between saving a wounded soldier or a dying child in Iraq… to landing in the middle of an active firefight to recover his fallen brother… this episode explores what it truly means to make impossible decisions when lives are on the line. Dan opens up about combat leadership, moral courage, faith, brotherhood, and the weight of co...
In this episode, retired Air Force Colonel and fighter pilot Derek Oaks tackles one of the toughest leadership realities: What do you do when your boss makes a bad decision — and you still have to execute? Through a powerful combat story from Afghanistan, Derek shares a high-stakes mission where a flawed tactical call led to a missed opportunity to eliminate a high-value target. Instead of staying stuck in frustration or blaming the ground commander, he unpacks the deeper leadership lesson: y...
In this episode, Derek Oaks sits down with retired Air Force General Jim Slife to answer a critical leadership question: Who actually owns risk? From young pilots who believe they’re bulletproof to senior leaders managing global operations, this episode explores how understanding risk evolves with responsibility. General Slife shares powerful lessons from his 35-year career, including the lasting impact of Operation Gothic Serpent—better known as the Battle of Mogadishu—and introduces w...
In this episode of Commander’s Intent, retired Air Force Colonel and fighter pilot Derek Oaks and Rob Powell explore a powerful question: Can Stephen Covey’s 7 Habits of Highly Effective People actually make you a better strategist? Drawing from military leadership, business strategy, and real-world examples, they break down each habit—from Be Proactive to Sharpen the Saw—and reframe it through a strategic lens. This episode dives into decision-making under pressure, defining your end state, ...
In this episode of Commander’s Intent, retired Air Force Colonel and fighter pilot Derek Oaks breaks down a hard leadership truth: plans rarely survive first contact—but planning is still essential. Drawing from real combat missions and life-or-death decisions, Derek explains why mental rehearsal, preparation, and clarity of intent matter more than a perfect plan. From military operations to business, relationships, and everyday leadership, this episode shows how planning builds alignment, re...
In this episode of Commander’s Intent, retired Air Force Colonel and fighter pilot Derek Oaks and co-host Rob Powell break down how leaders should think about risk—and why fear-based decision-making quietly destroys momentum, trust, and mission success. Drawing from military aviation, combat operations, business leadership, and everyday life, they explain why risk can never be reduced to zero, why safety alone cannot be the goal, and how great leaders learn to balance likelihood, impact, and ...
Hesitation isn’t harmless—it’s expensive. In this episode of Commander’s Intent, retired Air Force Colonel and fighter pilot Derek Oaks breaks down how decision hesitancy is quietly killing momentum, confidence, and results in today’s organizations. Backed by real-world data and battlefield-tested leadership lessons, Derek explains why leaders freeze, how micromanagement and information overload fuel indecision, and why waiting often causes more damage than a wrong call. He shares practical s...
In this episode of Commander’s Intent, retired Air Force Colonel and fighter pilot Derek Oaks challenges a question many people secretly ask: Why even bother setting goals when most people quit anyway? Derek and co-host Rob break down why goals fail, why vision matters more than resolutions, and how leaders use goals as stepping stones, not finish lines. Through real-world leadership lessons, personal stories, and military insight, this episode reframes goal-setting as a tool for growth, clar...
In this episode of Commander's Intent, retired Air Force Colonel and leadership mentor Derek Oaks breaks down one of the most overlooked but critical leadership skills: creating a shared vision with your team. Drawing from his experience as a fighter squadron commander, Derek explains how understanding individual goals, motivations, and personal aspirations allows leaders to align people with the organization’s mission in a meaningful way. This episode explores how leaders can move teams beyo...
In this powerful episode of Commander’s Intent, Derek Oaks and his guests unpack the true significance behind the rescue of Private Jessica Lynch—and why it was never just about military tactics. This wasn’t a mission driven by efficiency, profit, or ROI. It was a statement of values. Through firsthand accounts from those involved in the planning and execution, this conversation reveals what happens when an organization is willing to pause everything, redirect massive resources, and act...
In this heartfelt episode of Commander’s Intent, Derek Oaks and Rob reflect on choosing gratitude even during holiday separation—whether caused by military service, demanding careers, leadership responsibilities, or life circumstances beyond your control. Drawing from years of deployments, missed Christmases, and time spent far from family, they share powerful stories about perspective, service, and finding meaning when you’re missing the people who matter most.
In this episode of Commander’s Intent, Derek Oaks and former senior diplomat Bart Marcois break down how high-stakes leaders make decisions knowing they’ll be second-guessed. Using the 2003 Iraq invasion as a case study, they explore confirmation bias, imperfect intelligence, and the reality that leaders rarely get “good” options—only necessary ones. This conversation challenges listeners to rethink decision-making under pressure and focus on intent, clarity, and accountability when the cost ...
In this episode, Derek Oaks breaks down the five essential keys to building a successful career—no matter your field. Drawing from his experience as an Air Force squadron commander, Derek reveals why technical competence, communication, leadership opportunities, doing the “required squares,” and understanding how your team fits into the bigger mission are the true drivers of long-term success and fulfillment. This is the episode for anyone who wants clarity, direction, and a proven framework ...
In this episode, Derek and Rob break down what AI really is, how it functions as a decision-support system, and why leaders must be cautious about trusting it blindly. They share real examples—from aviation to law—showing how AI can boost productivity, but also how it can mislead, hallucinate, and create false confidence. This conversation equips you with a grounded understanding of AI’s strengths, limits, and how to use it responsibly in high-stakes decision-making.
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