About Derek Oaks | Combat A-10 Pilot & Leadership Speaker
About Derek Oaks

It's not about being the best in the world. It's about being the best for the world.

Speaker, mentor, pilot, and student of leadership — Derek speaks, writes, and teaches about leadership and decision-making, helping people and teams govern themselves, focus on what matters, and become confident decision-makers.

Who I am

I'm no hero. But I've spent my life in the company of heroes.

Men and women willing to sacrifice, to lay down their lives for strangers. I first put on a uniform at 18, inspired by the heroes of my dad's generation — my dad among them — and by the many who fought and too often died for freedoms the rest of us enjoy. I couldn't stand the thought of sitting on the sidelines while someone else fought for mine.

"Freedom has a taste. It's a tangible reality."— my dad

I've tasted that reality all over the world. I've also felt its absence — the constriction of freedoms taken, the hopelessness that comes from never knowing what true agency is.

My passions are simple: people, purpose, and planes. My aim is to help people get the most out of themselves, push their personal envelope, and fill their lives with meaningful purpose.

What is my message?

Govern yourself. Focus on what matters. Decide with confidence.

I've had years of experience as the decision-maker — and a lifetime of watching leadership done well and done badly. Underneath good leadership at every level is the same thing: the ability to govern yourself, to make and act on sound decisions, and to train your replacements.

My message is for leaders and followers alike. It's about learning to govern yourself, focus on what matters, and become a confident decision-maker in any walk of life.

Bio

Thirty years of leading when it counted

Derek is a senior executive with more than thirty years of operational and leadership experience across defense, aviation, charitable organizations, and small-business development. A 24-plus-year Air Force veteran and retired Colonel, he led at multiple levels of command in both peacetime and combat operations, and managed billion-dollar programs as a Headquarters Air Force staff officer at the Pentagon.

In the private sector, Derek has worked as an organizational leadership consultant and as a director of business development and programs, supporting multiple defense contractors. A published aviation author, he has logged more than 5,200 flight hours — many in combat — across more than 30 types of aircraft. He and his wife, Preot, are the parents of four children.

Reasons to book Derek

What your audience gets

01

Real-world experience

From leading in combat to growing small businesses, running youth organizations, and teaching at the individual, team, and organizational level — Derek's experience benefits every level of your team.

02

What you see is what you get

No clinging to titles or grasping at positions. He's held a few, but he's simply "Derek," "Woody," "Dad," or "Preot's husband" — and he likes it that way.

03

Zero drama

A middle child who's been "Smack," a "doolie," "Blue Four," and plenty of forgettable roles that taught him humility. He's easy to work with, and he knows he's never the reason you're there.

04

You'll learn together

Derek is a perpetual student. Raised at the feet of two genuine servant leaders — his parents — he believes he's never the smartest person in the room, and can always get better.

05

He'll help you find a way to yes

His approach gets your team looking for the path instead of the obstacles.

How is Derek different?

Instructional. Relatable. Engaging.

Instructional

Lasting and actionable

Derek's content is universal and inspiring. Your people leave with a clearer "why," real clarity of purpose, and practical how-to's they can use to perform at their next level and lead more extraordinary lives.

Relatable

Built for a changing world

Our workforces are in constant change, and the way we lead, communicate, and connect has to change with them. Derek helps audiences build the mindset and skill set to meet a shifting world with more agility and ease.

Engaging

Humor, story, and strategy

An uncommon blend of humor, story, strategy, and relevant messaging. From the senior leader to the brand-new intern, Derek connects with every person in the room and leaves them eager to take positive action.

Bring Derek to your team

Speaking, media, or a bulk order of Velocity — tell Derek what you need. If he's the right fit, he'll say so. If he isn't, he'll point you somewhere better.

Speaking & Public Engagement

Speaker Request Form

Thanks for considering Derek for your event.

At Decisive Leadership, we welcome the opportunity to share hard-won lessons on leadership and decision-making with the broader business community, executive and operations teams, conferences, academic institutions, and military and veteran organizations — anyone working to build confident, capable leaders. We believe leadership isn't reserved for the corner office, and that the right message delivered to the right room can change how an entire team performs.

To help us make the most informed decision about your request for Derek to speak, please complete the speaker request form below. The more you can tell us about your event, your audience, and what you're hoping the talk will accomplish, the better we can serve you.

We do our best to read every request in a timely manner. Because of the volume of inquiries, we aren't always able to respond personally to each one. If your event looks like a strong fit, you can expect to hear from Derek's team within 1–2 weeks — often sooner. If the timing or fit isn't right this time, we'll do our best to let you know that too.

And true to Derek's mindset, we'll always try to find a way to yes.