Former fighter pilot and keynote speaker Waldo Waldman shares how lessons from the cockpit – trust, preparation, and teamwork – can help business leaders build resilient, high-performing teams.
By Pete Mercer
Have you ever found yourself flying solo, metaphorically speaking? There might be road warriors and field reps in the industry who feel that they’re carrying the business on their backs, but the reality is that everyone needs a wingman. Without a wingman, you are exposed to attacks from behind that will reduce your effectiveness, your productivity, and eventually your bottom line. If you don’t have a wingman by your side to check for weaknesses and blind spots, it might be time to find one.
Waldo Waldman is a professional sales and leadership keynote speaker whose primary focus is to help businesses build collaborative, team-oriented environments, leveraging principles like accountability, trust, relationships, preparation, courage, and resilience. Waldman’s perspective on these attributes is unique – these are all things he not only learned in the cockpit as a combat decorated fighter pilot, but also in real-world corporate sales roles.
Repertoire Magazine sat down with Waldman to discuss how he draws from his 23-year military career to help businesses better develop their teams.
Overcoming challenges in the cockpit
Waldman’s approach is compelling because he’s using his lived experience as a combat pilot to talk about team building and resilience. This is obviously not a shared experience for everyone – how many of us have been in a cockpit during an aerial dogfight? If you’re going to be successful (and in Waldman’s case, stay alive), you have to be resilient to any changes in your environment.
“Flying complex jets in the heat of battle is challenging – leveraging this million-dollar piece of machinery you call an F-16, with all the weapons systems, tactics, tools, and teamwork involved was critical. You have to make fast decisions based on data that’s coming at you very quickly, which makes responsiveness, agility, flexibility, adaptability all very important,” Waldman said.
Even with all the complexities of controlling an aircraft in intense situations, one of Waldman’s biggest challenges was overcoming claustrophobia, the overwhelming fear of enclosed spaces, while in a cockpit. It started three years into his flying career with a near-death experience 35-feet underwater while scuba diving that then turned into PTSD-induced claustrophobia at 30,000 feet.
“What ensued was this journey of resilience and courage, facing my fears to do what I love more than anything else, which was to fly jets,” he said. “I had to actively choose between the joy of following my passion for flying or getting sucked into the dungeon of doubt and fear. Making that choice allowed me to stay out of the danger zone and fly into the performance zone.”
The importance of a wingman
Do you have a wingman in your life? A wingman is someone who partners with you to help you achieve more – overcoming obstacles, adapting to change and achieving success. Any good company culture is built on partnerships like these, where people can come together and have a greater impact. Waldman believes the most important wingman in your life is the one you spend the most time with.
“The most important wingman is yourself. You have to trust the person you see in the mirror, which is something you can build through preparation and putting in the reps. When it comes to tactics and performance, I always say, ‘Wingmen never wing it.’ You don’t fly by the seat of your pants, and you can’t sell or lead by the seat of your pants.”
It all starts with building within yourself, challenging yourself through exposure and stretching outside of your comfort zone to grow into the person you need to be. Change is hard and uncomfortable, but it’s necessary to evolve and adapt to the moment that you are in.
Working out that confidence muscle is the first step towards success, but there’s only so far you can go on your own. Waldman said, “There’s a limit to your skill, your perspective, and your courage. This is why your wingman, the people in your formation who you have trusting relationships with, needs to be someone you can go to and say the three most important words in life, which are, ‘I need help.’”
The 7 Wingman Principles
Waldman has seven foundational principles that he designed to be essential to building cultures of trust, teamwork, and excellence.
1. Winners Never Fly Solo: You might be able to survive on your own, but you win as a team. Waldman said, “You have to go out and build those relationships, which means you need to serve first. I call it giving your wings away. If you want to gain a wingman, become one.”
2. Leaders Promote Collaborative Cultures: Collaboration means cross-checking each other’s blind spots. Any threats that can derail your productivity are going to sneak up from behind you, so you need a wingman to check the ‘6-o’clock position’ to improve trust across the organization.
3. Training and Preparation Drive Sales Excellence: One of Waldman’s mantras is “Wingmen never wing it.” If you’re going to win in business, you need to build a performance-focused culture. He likened this principle to constantly upgrading the weapons systems on an F-16, ensuring that it was ready for any new challenges it might face.
4. Standards Determine Culture: The accountability, attention to detail, responsiveness, and discipline set by the standards of your leadership will determine the output of the culture. “Hold people to a higher standard, and the most important standard you must hold is of yourself. That’s how you command excellence.”
5. Relationships are Foundational: If you’re going to build strong, lasting relationships within your organization, you need mutual trust. There are plenty of heroes in your organization that aren’t in the spotlight, and they need to be recognized for everything they contribute. “If you’re in sales, you need to build better relationships with your account managers and the people who are making sure your systems are up-to-date. Without them, you can’t do your job.”
6. Be Courageous, Not Fearless: There’s a difference between courageous and fearless. When you’re embracing courage, you are controlling your fear. Fearless can mean reckless, and fear is an important element of the greater equation. “Fear is a common component, and it shows that you’re human. It shows that you’re fighting for something important.”
7. Core Values are Essential for Growth: Your core values are the essential building blocks for growth within your organization. Leadership is held to a higher standard, so you need to practice what you preach and emulate the core values of your organization.
Resilience today
In 2025, uncertainty is all around us. It comes in the form of tariffs, unemployment rates, artificial intelligence, economic uncertainty, international conflicts, and so much more. It’s a lot to take in from every side, but resiliency is about finding ways to push forward and keep getting back up when you’re getting pushed down.
With all these high-stress situations surrounding us, it would be really easy to stay in our comfort zones and not push boundaries. But would that make us more effective? By embracing a resilient mindset, you can walk out into the world with no fear, because you know that when you get knocked down, you will pick yourself back up.
Waldman said, “Resilience is your ability to adapt to stressors and bounce back from failure, rejection, doubt, fear, and performance debilitating situations. It’s your ability to say, ‘I’m getting back in the cockpit of my life and I’m going to still take the action necessary to grow.’ It’s about avoiding shrinking away from fear and knowing that the stress will come anyway. You’re still able to fly through that fear because you have people depending on you.”
It’s important to understand how resiliency works: it’s not a lack of fear or anxiety, but it’s about pushing through the fear and anxiety to get the job done. It’s not comfortable and it might not even be fun, but it will grow and stretch you into the leader you are meant to become. “Fear, anxiety and doubt are going to be present, but it’s going to diminish. The more you get used to it, the easier it gets. Expose yourself to those challenging situations – it’s part of what a growth mindset is all about.”