Stephanie joined JetSuite as a 30-year veteran of the commercial and business aviation industry. She is an expert at training individuals and Fortune 500 companies around the world as an award-winning executive coach, sales mentor, and business advisor. In addition to coaching some of the most elite sales teams in the country using science-based selling strategies, she also served as former Vice President of Sales, Western Region, at Flexjet and in various executive roles at SkyJet Airlines.
Stephanie is the author of Profit Like a Girl: A Woman’s Guide to Kicking Butt in Sales and Leadership.
What was your dream job as a child?
I wanted to work in aviation. My dad was in the Air Force so I grew up on active military bases. Since I was around planes all the time, I knew I wanted to do something in the travel and aviation industries.
At first, I didn’t know what I could do in aviation. All I knew is that I didn’t want to be a pilot or a flight attendant, and in film or TV, the only people in aviation they ever showed were pilots or flight attendants. If you were a woman, being a pilot was out of the question, or so I thought, because you never saw a female pilot. How could that be an option? So that left me with being a flight attendant, and that didn’t interest me.
That’s why I started my very first job parking planes. Not flying planes—parking them. I started off on the ramp at Boston Logan International Airport. You know those people who shlock your luggage and park the planes? That was me.
Was that also a taboo job for a woman back then?
It was. I loved it though! I was one of maybe two women on the ramp. We kept working operations at that point but I got a kick from it because the guys would always take all the heavy luggage and be like, “Here let me take that, Steph.” It was a lot of fun.
It also helped me to cut my teeth in aviation. You really learn all the ins and outs of the business working those entry-level jobs. We were cross-trained. We worked on the ramp and we would also work in customer service. So you had to learn the entire business on the front end and then you had to learn how to work with customers.
I learned how to handle customers who were anxious or angry because their plane was delayed, their baggage got lost…things like that. It taught me a lot about how to diffuse people very quickly. Just imagine—you have strangers screaming in your face about things you can’t control, like the weather, the computer system, etc. We all know it can be a mess. But the experience was valuable in the end. I learned early on how to get people to relax and yet still solve their problem by truly listening and understanding what they were asking for.
In terms of gender parity and women’s representation, things are changing, and you must get on board. At JetSuite we are mindful of that because historically our space has been largely made up of men. It has not been an inclusive industry. And so we are determined to pull the industry along with us, and we take that mission seriously.
Groups like Women in Aviation, the Organization of Black Aviation Professionals, the National Gay Pilot Association—we team up with all of them and often go to their conferences to connect and recruit new people.
We are really purposeful about doing our part. We know we can’t control the whole industry but we can certainly make change here in our corner of things, and specifically in our company. We want to make sure that anyone who looks at our company or industry sees themselves represented here. When they see that aviation is a space with women, people of color, those from other groups that were often sidelined, it can resonate with them. They realize, “Hey, I belong here too.”
Our push for inclusion and diversity is a competitive advantage, in my mind. Not only is our team culturally and physically diverse, we have diversity of thought. So when we sit together as an executive team and need to make big decisions, we bring those different backgrounds and viewpoints to the table with us, which allows us to be more creative.
Changing the culture of an industry is never easy—you always need advocates who can get behind and support the shift. That’s why I’m very appreciative of our CEO Alex Wilcox. He fits the traditional profile of someone in our industry—he’s a man, he’s a pilot—but he is absolutely the biggest supporter of these efforts. Which is great because together we can kind of team up, and block and tackle, and create that change throughout the organization.
Did you have any key mentors?
Throughout my life, I had people that saw something in me and helped me to nurture my strengths and potential. I am fortunate that I had three great bosses in my career, which is probably more than most people today will ever have. You’re going to work with a lot of bosses in your career, that’s a given…but are they great bosses? Are they mindful of your strengths and your gifts? Do they help you succeed? Do they respect you enough to tell it to you straight when you do something wrong? That sort of trust and honesty is key. And that’s the leadership style that my mentors always demonstrated and instilled in me.
I once had a boss who is still a mentor of mine. We stay in touch, ask each other’s feedback on things, all of that. This person taught me a crucial lesson: the power of questions and communication. And now that I’m an executive coach and president of a company, it’s something I draw on every day. Any leader must learn how to ask questions of their team so they can truly understand a situation. Because if you don’t ask and you just assume things, it puts people on the defensive. If you haven’t actually made the effort to understand that person, you can make assumptions about their choices or intentions that turn out to be wrong. And then you end up making things even worse!
We must practice understanding the different styles that people use to communicate. Then we need to ensure we adjust our communication so the other person feels heard. From there, it becomes a lot easier to resolve conflicts and help people improve and grow.
That focus on communication goes in both directions, by the way. It’s not just for when people are struggling and need guidance. There were many times when a mentor who really cared about me would stop and let me know that I was doing well. I think many of us in leadership can definitely become better at understanding and using positive reinforcement. Sometimes, all your employee needs to hear is: “You killed it. You were awesome!” and you just leave it at that. I was lucky that my mentors cultivated that kind of trust and dialogue with me, and that’s given me this wonderful roadmap to now go out and mentor others.
What is the largest obstacle you have encountered, and how did you overcome it?
The biggest challenge I’ve ever faced is when I was diagnosed with cancer. That is one of those walks you must walk alone. As much as other people may want to help you, they really can’t. It’s one of those things you come to grips with all on your own, because you are truly in a fight for your life.
Just getting the diagnosis was a huge ordeal. I don’t have any history of cancer in my family at all, so we still don’t know why I got it in the first place.
Basically, at my other job, I had to get an executive psychical once a year along with the rest of the senior team. They’d have you spend the whole day getting poked and prodded and doing stress tests. So, it’s the last part of the day and I go in for my mammogram. The nurse comes to get me, I go in, we do the typical process, and she leaves. I’m literally reading a magazine at this point in the waiting room, not thinking anything, and just ready to finish up the day.
The nurse comes back and says, “We’re going to take a few more tests.” She leaves, and then somebody else comes to explain that they are moving me into a different room. We go in to this other room. It’s dark and cold, there are people standing around and waiting. Then it starts to click in my head. Suddenly it hit me: “Whoa, wait a minute. Something is off.”
The doctor said they noticed something and want to get a closer look. It’s interesting how much I can remember from those few moments. I can still remember how the room smelled, the sound of the machines clicking as they took my measurements, all of that.
The woman finished taking the scan and taking photos and says to me, “we saw something in there, and I think we need to get it tested.” And that moment it just got real.
Later that day I went home. I remember walking through our garage to the house, hearing music playing and smelling the food my husband was cooking. I walk in and my husband says, “How was your day?” And I just felt this release of emotion as I tried telling him what happened. He held me and said the most perfect thing: whatever it is, we’ll handle it. It was exactly what I needed to hear, you know? Like I said, I’m the child of an Air Force pilot, the child of a soldier. And when I heard my husband’s words I realized, “OK. Whether I like it or not, this is my mission right now. My mission is to get through this.”
A few days later I was in a business meeting. I still hadn’t told anyone at work because I didn’t have enough details yet. I saw my phone ringing and knew it was the doctor. I left the conference room to go and answer the phone. The doctor says, “Ok Steph we have your results back. It’s breast cancer.” And I remember asking her, “Am I going to die?” She says, “Not on my watch, you’re not!” She explains informs me they don’t know how aggressive it is, but we need to move ahead with surgery to find out.
And just like that, it was “Game On.” I instantly shifted into a different mode. In my mind I thought, “Ok, it is what it is. Now we need to get to work.” And that’s exactly what we did. We took care of it.
Cancer changes you, without a doubt, but it also changes everybody around you. Your friends and family are going through this experience with you and they don’t know what to do. They want to be supportive and helpful, but they really don’t know what to do. None of us know what to do! And that’s very hard on people.
That was the most difficult time in my life. But even with everything that happened, I am still the type of person that likes to look at things half full. Cancer sucked but there are good things that came out of it, where I can look back and recognize, “Wow, that really helped put things in perspective.”
You really start to prioritize certain parts of your life. You realize that not everything is important. You really start to see life for what it is, and for what truly matters. At the time, my daughter was in 11th grade. After my surgery I was taking time to heal, so she used to feed me and take care of me. I got to witness her love and care for me and saw how protective she became. I thought to myself, “Lord, if I don’t make it through this, at least I know my husband and I raised a great daughter.”
Just from watching her, I knew she was going to be a great mom and a great partner to someone. All the things you hope for when you’re raising your kids, I got to see that come to life in my daughter. And lastly, I got to see the strength I have inside myself.
I would say that experience was my most difficult challenge. And if I had to do it again, would I? No. But at the same time, I would not be who I am now without that experience. I wouldn’t be the same kind of leader or the same kind of parent. So, in ways there was some good that came out of it.
Now, when I’m coaching my C-suite clients, sometimes I just tell them, “Go and spend some time with your kids. Be present for them.” Sometimes we think because we’re working hard and caught up in the everyday grind, there’s only so much we can give our kids. We focus on looking after them in their material needs, giving them stuff they want, and we think that’s enough. But if you actually sit down with your children and ask them what they need, it’s never really objects. They want help with their homework. They want someone to listen to what’s going on in their lives. My cancer diagnosis really opened my eyes to this, and it’s something I try to share with my clients. These are very successful people by any conventional measure. But I tell them, “If you aren’t prioritizing your connections with family, then you need to redefine your meaning of success.”
Those are the kinds of things I learned from my battle with cancer. I think the experience left me less uptight and more open. It was a springboard toward a new perspective. So now, when I see other executives struggling, it reminds me of where I was before my diagnosis. And I try to tell them, “I can see where this is going, and I’m hoping I can inspire you to try a different path. I don’t want it to take a deadly illness like cancer to make you realize what’s important.”