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 purpose when making critical decisions. From flying low-level combat missions to business delays that push risk onto customers and teams, this conversation challenges the idea that avoiding risk makes leaders safer.

This episode is about clarity over caution, mission over comfort, and learning how to mitigate risk without freezing, deferring, or shifting responsibility onto others. If you lead people, make decisions under pressure, or feel stuck between fear and action—this episode is for you.

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 strategies to overcome analysis paralysis, empower teams, set decision deadlines, and build confidence through action. The key takeaway: leadership isn’t about perfect decisions—it’s about timely ones that move you forward.

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, clarity, and disciplined action even when you don’t hit every target. 

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 beyond “just showing up for a paycheck” to true commitment, ownership, and pride in the mission. If you want higher performance, stronger engagement, less turnover, and a team that genuinely cares about the outcome, this conversation shows how shared vision is where leadership magic really happens.

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 decisively to protect one person. The episode explores leadership under pressure, trust, preparation, and the cultural message sent when leaders prove—without hesitation—that their people matter. 

More than a war story, this episode delivers a timeless leadership lesson: when people know they won’t be abandoned, they’ll give everything in return. 

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 of hesitation is even higher than the risk of action. 

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 to advance their career with purpose. 

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.

In this episode, Derek Oaks unpacks one of the most defining traits of great leadership—empathy. Through a deeply personal story about nearly losing his son while preparing for deployment, Derek reveals how empathetic leadership from his commander kept him grounded, capable, and effective during the hardest season of his life. This powerful episode highlights the real difference between narcissistic leadership and empathetic leadership, why empathy strengthens accountability, and how true leaders support without disempowering.