Curated Leadership Experiences
Some leadership lessons can’t be delivered from a stage. These are rare, relationship-driven rooms where a small number of leaders spend real time with Jason, on the ground and in the air.
“The most important conversations of my career didn’t happen in a conference room. They happened at altitude.”
Lt Col Jason O. Harris, USAF (Ret.) · Former Special Operations aviator · Boeing 777 pilot
Five rooms. Very few seats.
For leaders and teams who want more than a keynote. Each experience is built around the No Fail Trust® principles that keep teams alive when failure isn’t an option, and each one is shaped to the people in the room.
Aspen Leadership & Flight Experience
Two days in Aspen, in the mountains and in the cockpit, built around the principles that keep teams alive when failure isn’t an option. This is where Jason’s two worlds meet: the discipline of combat aviation and the clarity that comes from stepping far away from the office.
What the experience may include
- Two days and one night in Aspen, Colorado
- Time in the air with Jason at the controls
- A flight simulator session, time permitting, that puts trust and decision-making under real pressure
- Pre-flight briefings and debriefs, the same discipline Jason relied on across 470 combat sorties
- Candid leadership conversations in the mountains, with room to think
Who it’s for
Shaped around whoever is in the room: your executive team, a small cohort of senior leaders, or one leader who wants the most immersive time with Jason.
Every experience is tailored, so the final itinerary depends on your group, your goals, the time available and, as every pilot knows, the weather. Details are confirmed with you in advance.
Cigars, Scotch & Leadership Under Pressure
An evening mastermind for a handful of senior leaders: unhurried, candid and off the record. The kind of conversation about trust and decision-making you can’t schedule into a calendar invite.
Request an InvitationVIP Leadership Day
A full day, one-to-one or with your top team, designed entirely around the challenges you’re facing right now. The deepest, most personal way to work with Jason.
Request an InvitationExecutive Mastermind Experiences
A small, curated cohort of executives working through trust and high-stakes leadership together over time. Built on relationships, not transactions, and capped to keep the room real.
Request an InvitationPrivate Fireside Leadership Conversations
A limited number of private, one-to-one conversations with Jason throughout the year, for leaders navigating a defining moment who want a trusted, battle-tested sounding board.
Request an InvitationEvery experience starts with a conversation
Request
Tell us about you, your team and what you’re navigating right now.
Conversation
Jason’s team personally reviews every request and reaches out if it’s a fit.
Curated proposal
You receive a proposal shaped around your goals, your people and your timeline, with investment details.
Built in combat cockpits. Proven in boardrooms.
Jason O. Harris is a retired U.S. Air Force Lieutenant Colonel and Special Operations aviator with 470 combat sorties across 11 deployments, an active Boeing 777 pilot, a Certified Speaking Professional (CSP) and the author of No Fail Trust: The Flight Manual for Building Teams That Deliver Under Pressure.
These experiences take the same principles he teaches from the stage and put them to work in smaller rooms, with more time, more candor and more depth.
About the book Book a keynoteRequest an invitation
Every experience begins with a conversation. Tell us a little about you and what you’re navigating, and Jason’s team will personally review your request and reach out if it’s a fit.
- Reviewed personally, not by an automated queue
- Relationship-driven, never transactional
- Complete discretion throughout
- Investment shared by inquiry, once we understand what you need
Frequently asked
Why isn’t pricing listed?
Each experience is curated around the people in the room, the location and the outcomes you’re after, so investment is shared by inquiry once we understand what you need.
Can one of these be added to a keynote?
Yes. Many clients pair a keynote with a VIP Leadership Day or an executive mastermind so the message keeps working after the event. Mention it in your request.
Who are these experiences for?
Senior leaders, executive teams and organizations that want to build trust deliberately, especially those leading through pressure, change or a defining moment.
Why are seats so limited?
Because the value is in the relationship and the time with Jason. Keeping each room small keeps it candid and real.