What Private Jet Brokering Taught Me About Reading People

Q: Was there a specific interview or hire where someone talked a great game but had nothing behind it, and it went badly? What actually happened once they were in the seat?

Yes, a couple of times. I distinctly remember a time during the hiring process where we decided to take a leap on someone with exact industry sales experience. For most sales roles, that's exactly what you'd look for. However, in the private jet brokerage industry, it is full of individuals who can talk the talk but not walk the walk. The notion of being able to tell their peers they work in the private jet industry is enough to make these individuals ignore the outcomes they claim to achieve. He'd say things like, "I can connect you with so-and-so," but in reality, when I called that claim out, it could not be fulfilled. The experience took time, money, and many conversations to get to the reality that there is more than meets the eye. Just because someone talks the talk and comes from the industry does not mean anything, when you dig deeper on the details, all the information comes out.

Q: Or the flip side: a moment where someone with zero fluff, just hard numbers, won you over on the spot? What did they actually put in front of you?

I remember a time where he led with numbers, not only exceeding his quotas, but doing so at a company that was going out of business. Someone looking for a sales job after their company laid off its employees can be a goldmine for talent. Once he came on board, he immediately had the right initiative, consistently asked proactive questions, and committed to the process day in and day out without negotiating on it. It took eight months, given the nature, learning curve, and structure of how charter deals gain momentum, but he got himself to the point where he was leading the team on a monthly basis, ahead of salespeople with four plus years of experience.

Q: Is there a specific person (a hire, or someone you passed on) whose athletic background showed up directly in how they performed? What did you actually watch them do?

Yes, she constantly showed a willingness to challenge what her full potential was. She took criticism as an opportunity to learn and become better, not as a personal attack. I watched her fail, feel the pain of losing a deal, and then get curious about taking that failure as an opportunity to learn.

Q: Were you a competitive athlete yourself growing up?

I was an Olympic trials qualifier in swimming in 2012. The reality of this experience is something you don't appreciate at the time, but it delivers the skills to you early on for what your relationship should be with challenge and with failure. This relationship is crucial to one's success, and challenge was a daily teaching: navigating cardio obstacles, strength obstacles, body maintenance obstacles. Things constantly had to be reevaluated. When I finally failed to make the Olympics, I needed to take the time to create my new identity. It was painful, confusing, and extremely tough to go from being the best at something to starting all over again. You learn over time, though, that you truly are not starting over again. You have a leg up on everyone around you, with the core morals already ingrained in yourself. That's exactly the instinct I look for in a hire now: not whether someone's won before, but whether they know how to rebuild after they've lost.

Q: First time you asked it and it actually worked: what did the person say, and how did you know in that moment it told you something real?

Yes, there have been several occasions where I've interviewed applicants and they've answered this question well. The answer may surprise you, because in reality there isn't really any one thing that nobody else would believe. The real value is in the navigation, how the individual deals with a near impossible question to answer. The best answer I ever got started with the person saying, "That's a good question, let me think about that," followed by thirty seconds of silence. Her final answer was: if individuals don't have the cognitive ability to vote before 18, they should also lose that ability after the age of 70. Agree or disagree, that answer told me more about her willingness to explore her own thoughts and beliefs, and to challenge others' opinions even in the face of disagreement.

Q: Has anyone completely fumbled it in a way that confirmed they weren't right for the deal or the role? What happened?

Yes, absolutely. This usually shows up as a safe or diplomatic answer that really comes out as a half hearted answer. The question helps determine if someone is a crowd pleaser or a truth teller. Honestly, it's a little deflating to watch in real time: you can see someone talented choose the safe way out instead of risking being wrong in front of you. It's incredibly helpful to understand who prioritizes their own principles rather than generic social ones. I've heard generic answers like "I believe in world peace." To be honest, a better answer in my eyes is one that says, "I haven't thought that deeply about that question before, and I don't have an answer at the moment." That at least shows a willingness to face failure and learn from it.

None of these are tricks. They are just the three places I have learned the truth tends to show up: in the numbers someone actually put up, in how they behave once something goes wrong, and in what they say when there is no safe answer available. Hiring well is not that different from the work I do every day getting people onto a plane. In both cases, you are making a high stakes call on someone's character with limited time and a lot riding on being right.