Debrief Your Day: How Pilots Practice Leadership and Growth

In aviation, the mission doesn’t end when the wheels touch the ground — in many ways, that’s where the real learning begins.

One of the most important parts of every flight lesson I teach is the post-flight debrief. It’s a habit I picked up during my time in the Ranger Regiment, where After Action Reviews (AARs) were a staple of mission success. These reviews didn’t just help us become better soldiers — they made us better leaders and more thoughtful teammates.

Over time, I’ve refined that military discipline into a leadership habit I now use across every area of life: from coaching young pilots to guiding my son through Civil Air Patrol events and even post-soccer game talks.

The Power of the Debrief

When a student and I finish a flight and begin wiping down the airplane, I ask a series of questions that serve as a compass for growth:

1. What did we do today?

2. What did you learn?

3. What’s your plan for next time?

4. How did we embody our core values?

5. What are you grateful for today?

Let’s unpack these.

1. What Did We Do Today?

This question sparks active recall — a powerful technique shown to strengthen memory retention. Together, we review what we covered in ground training and walk through the entire flight again, chair-flying the maneuvers to cement the experience.

Try this at home: Use a dedicated journal like the BestSelf Co. Self Journal to walk yourself through your day. Recall meetings, conversations, workouts — anything worth remembering.

2. What Did You Learn?

Learning is the act of extracting meaning from experience. Every flight has a lesson — whether it’s in executing a perfect soft field landing or realizing we forgot to check the NOTAMs. By asking this question, we begin to transform mistakes into milestones.

Tool for Growth: I recommend The Daily Stoic by Ryan Holiday as a daily self-assessment and reflection aid. It’s one of the best companions to your debrief ritual.

3. What’s Your Plan for Next Time?

Here, we shift from reflection to forward motion. What will we improve? What’s the study plan before our next flight? What weak areas are we polishing?

This keeps training deliberate, not just reactive.

4. How Did We Embody Our Core Values?

For my students, we refer to our flight school’s core values:

• Personal Courage

• Integrity

• Leadership

• Open Communication

• Teamwork

This is where the debrief becomes more than flying — it's about character. Did we own our mistakes? Communicate clearly? Support each other?

And yes, if you're parenting or coaching youth, this question sparks powerful conversations about life beyond the cockpit.

5. What Are You Grateful For?

Gratitude reframes even frustrating lessons. As I often remind my students: we are privileged to fly.

A century ago, humans had just taken to the sky. Today, we can climb into a Cessna, take the controls, and become pilots. That’s incredible. Let’s not forget the wonder — or the sacrifices of the aviators who came before us.

Recommended tool: Keep a simple gratitude journal on your nightstand and end your day the way we end our flights.

How This Applies to Life and Leadership

The debrief habit has helped my students become better pilots — but more importantly, it’s helped them become better people.

I’ve used this exact structure to help my son after Civil Air Patrol training events, soccer games, and school projects. It’s a method for humble self-reflection, continuous improvement, and intentional growth.

And it’s the foundation of my upcoming book:

Flight Plan for Leadership: A Ranger and Pilot's guide to clear thinking, confident action, and better business results. Inside, I share how post-flight habits like debriefs can build stronger leaders in the air, on the field, and in the boardroom.

Debrief Tools I Recommend (Affiliate Links)

• The Daily Stoic – For daily wisdom and reflection

• BestSelf Co. Journal – For structured goal-setting and debriefs

• Five-Minute Journal – For gratitude and self-awareness

• Kneeboard – For in-flight note-taking and review

Thanks for reading!