Summer Manager's Challenge

I got to do the coolest thing I’ve ever done in my entire professional career. We had an annual review with one of our core team members, Diana, who joined Wheels Up shortly after graduating from college. She has had an absolutely spectacular year of professional and personal growth. We got to tell her what an amazing and integral part of our team she is, and were able to bump her comp to reflect her expanded skill set. It was hands down the most rewarding thing I’ve ever been able to do, even after 15+ years in managerial roles. To start a company, assemble an amazing team, build a book of clients with interesting and challenging business opportunities, and then celebrate hard work with team members who are killing it. (The only thing missing was the trip to Rock Box karaoke like we did back in the Socrata days!)


I can’t take credit for Diana’s growth - from day 1, Elise blocked off big chunks of time to mentor and teach her. The whole team stepped up in support of Diana’s career development, and we now have a team member who I can honestly say we could not operate without.


There is no sugar coating this investment - mentoring and developing junior talent is a full-time job. I think it’s something that, as many folks climb the proverbial ladder and start overseeing larger and larger teams, they forget: this is the most important part of their job. A manager is a manager of people.



I worked at a company years ago that had a culture of managers. Everyone wanted to get promoted into a management position - they were rewarded with extra perks and a huge bump in compensation that they could never unlock as an individual contributor. The company had a bloated middle management layer full of people who really didn’t know (or honestly care about) how to lead or develop talent. And since the culture was entrenched, the vast majority of new managers had never had a good manager to learn from. The dysfunction just grew. But everyone still wanted to be a manager!


I love that so many companies in the tech world have principal level team members. Instead of advancing into a management track by default, there’s the option to grow in a path of domain expertise. Principal level team members are top-ranked individual contributors who spend their time being engineers or data scientists or architects or developers instead of being people managers. It’s a big title to earn and has massive respect in the industry. Best of all, it kills the adage that senior professionals have to aspire to manage teams of people in order to excel in their careers.


We aren’t nearly big enough to have multiple layers at Wheels Up, but I hope one day we are. But I also hope that we are disciplined enough to fill our managerial roles with good leaders who are passionate about developing their teams, and that we create career paths for exceptional individual contributors to continue expanding their impact by doing what they are exceptionally good at. It’ll be important that neither of these paths will be more lucrative or respected than the other. Check in with me in a couple years and see how we’re doing :)


I had a CEO years ago tell me it was their goal to make that company the place where every one of the employees did the best work of their careers. I’ve totally hijacked that sentiment and have it written on a post it note on my desk. I’ve added to it, too; I aspire to make Wheels Up the last job every one of our core team members has. I’m fully aware that this is a pipe dream - it’s incredibly hard to hire talent (even in the best of markets), especially when you are in startup mode and have tight timelines and lean budgets. But I believe that a very high talent bar is a line worth holding. If you do the meticulous work of hiring the right people and give them fulfilling work and an environment that supports a balanced life, they have no reason to ever leave. I can’t help but believe that it’s going to lead to a wildly successful company. At least that’s what Elise and I are banking on.


In the meantime, here’s my summer challenge for anyone who wants to join me: if you’re a manager of a team, or better yet, a manager of managers – pick one thing you can do to help develop your people and do it. Don’t just check the box by hurrying through your 1:1s like a zombie. Look for ways to set your teams up for success and build an action plan. Maybe it’s assigning a pet project, or offering an opportunity to shadow another team member, or just recommending a thoughtful book and talking about it over coffee. I truly believe it doesn’t take more than setting aside the time to care about your teammates and fostering a genuine interest in their development. You know, managing them. I’d love to hear what you think!