The biggest problem facing leadership in private aviation is becoming even bigger. Growth, that is, and the demands that go with scaling a small flight operation to the next level before it has reached cruising altitude on the previous one.
When Tradewind Aviation launched in 2001, our goal was self-sufficiency, and many other aviation operators of our size have the same goal. However, most companies are unable to attain a high level of self-sufficiency before being acquired, losing investors, or seeing their leaders retire or move on.
To guard against these results, my brother David and I made the decision from the beginning to grow Tradewind by building clientele and hiring talent to give the company enduring value. Indeed, as much as we love what we do, neither of us plans to lead Tradewind feet first. By casting a wide net, we have reeled in world-class talent for flight operations, ground operations, marketing, and more, beyond what is typical for a still-growing airline. We are so proud of our growth trajectory.
We have a philosophy of collaboration over delegation. It’s very easy for leadership to fall back on “we know best” or “because that’s how we’ve always done it.” We have found that providing opportunities for team members to innovate prevents stagnation and leads to better overall results than always taking direction from the executive office. When innovators are unable to (or don’t feel comfortable to) provide input, they will look for other professional opportunities, taking valuable ideas, unique talents, and possibly their colleagues with them.
Another challenge for leadership is mastery of details, which is where success in private aviation lies. Throughout my 30+ years in the aviation industry, I’ve seen that unfulfilled promises and expectations doesn’t bring clients back. On a Tradewind flight, every minute detail is considered. We put extensive effort into all the specificities that contribute to a pleasurable experience in the air.
Of course, staying on top of details is not as challenging for a leader of a small airline as it is for one running a large or growing operation. In the early days of Tradewind, for instance, my schedule allowed me to run to the market to purchase in-flight food and beverages requested by charter guests before the start of their flight.
Looking back, those moments were valuable in revealing our dedication to the flight experience we promised. As we grew and the challenges of self-sufficiency became keener, we realized bringing in talent wasn’t the whole solution. It also involved trusting talent to do their job right and with a touch that inspires our tagline – “Fly Personal.”
Furthermore, another key to leadership success is keeping the company young. Not in age, but in outlook.
With our position in the private aviation industry, Tradewind attracts young talent who are eager to gain experience. Many are new to the industry, and the fresh outlook they bring can be constructive toward informing our executive team – myself included. Conversations our team has with each other around the coffeemaker are exciting. We know that no suggestion is too crazy, and we look forward to implementing the best ideas in our structure and cementing them as policy.
For example, in the early days of the pandemic when aviation was under the microscope, travelers had to negotiate at commercial airports and some private carriers were forced to stop flying and refund tickets. Tradewind considered doing the same until one team member turned the situation on its head with the suggestion of giving clients an opportunity to use pre-purchased scheduled tickets toward private flights of their own. It was five tickets to get them there, and five more to bring them back.
We offered our guests the option, and many accepted. Instead of our financial department figuring ways to refund or extend tickets, all it took was a team member in our sales department to dream up an end around the issue. Tradewind was able to continue flying during a historically bad stretch for aviation simply by giving guests new utility.
Meanwhile, on the flight operations side, we have talent with new perspectives to evolve and improve other company policies. Others bring expertise in new technologies and are looking for ways to employ what they know. With our size and presence in private aviation, good team suggestions can become a standard procedure.
As a result, Tradewind is now driving best practices rather than following them. While that’s inspiring for our executives, it also inspires other companies that would like to have equivalent operational expertise.
Furthermore, leadership must embrace the importance of improving company culture. In my early days as a flight instructor, getting one’s start was all about the law of primacy: The first thing learned was the last thing forgotten. Several new recruits spent their first day watching several human resources videos to ensure what was deemed important by the higher ups stuck.
That approach doesn’t work anymore – at least not at Tradewind.
Instead, we make sure the first day is a well thought-out, positive experience for all new team members. We have orientation days where leadership lets new arrivals know how excited we are about their future with us. We break the ice by asking for a fun fact, with a promise that we won’t repeat it. Although this may seem elementary, we have found this to be very effective with breaking down barriers and finding commonalities, which is essential to making people feel that they belong at a company.
During orientation, I also spend time sharing about how we live, thrive, and survive as a team. It’s a technique I learned from JetBlue, our Gateway Partner, which let me sit in on a new hire orientation at which corporate ethos was Topic A. I speak with new talent and personally explain our mission that every Tradewind flight deserves the highest quality aircraft, crew, and service, and to make new recruits feel they’re a part of it from Day One.
When an organization is small, such “culturalization” can happen by osmosis: People observe the leader’s reactions and get immediate feedback. However, the more a company grows, the less that works.
Leadership is also about visibility and having your team see you ingratiated within the business. Even as the co-founder of Tradewind, I still fly the line, piloting our Pilatus PC-12 turboprops in the Northeast a few times a month and personally completing check rides with new pilots in our Caribbean destinations, like St Barths and as of next month, Virgin Gorda.
Plenty of management guides say my time could be better used on bigger things, but I disagree, as there is both validity and practical value by being in the cockpit and seeing firsthand the experience of our guests and team members. If a team member’s experience is in any way imperfect, our clients’ will be too.
In a lot of organizations, when the CEO shows up on the factory floor, everyone panics. Not at Tradewind. The way I figure is, if a pilot doesn’t want to fly with me, then something is wrong. It means they’re not sufficiently prepared.
Measuring profits is easy; calculating the quality of our experience is less so. I could sit in my office, but I’d rather be in the sky with our world-class team or chatting to our guests in the field. At Tradewind, aviation is more than a job – it’s a passion. I’ll be flying alongside our pilots and serving our guests until I no longer can.