They said I couldn’t do it…

Why ‘everyone needs a posse’ and other lessons from a “Best Bosses in Federal IT” winner.
Lisa DeMille (center) with her team from Salesforce at the Best Bosses in Fed IT awards, 2019

Lisa DeMille is vice president of Federal & Enterprise Solution Engineering at Salesforce — and one of 54 executives selected by the editors of FedScoop and WorkScoop as a “Best Bosses in Fed IT.”

Last week, I was selected along with some of the government’s top leaders as one of the “The 2019 Best Bosses in Federal IT” by FedScoop and WorkScoop. And it made me think about the path I took to get here.

Twenty years ago, I decided to do something crazy. I left my career as a publicist for HGTV because I wanted to break into technology — something that had always interested me.

Most everyone I spoke with about it thought I had lost my mind. I was in my thirties and starting over. They said, “No one does this and if they do, they are rarely successful. You will fail.”

Despite this negativity, I went with my gut — and also guidance from an uncle, who said I had to try. If I ended up moving back in with my parents and delivering pizzas for a living, well, at least I’d be fed. 

With no background in technology, the best position I could get was as an executive assistant to the senior vice president of government sales who reported to the CEO for one of the world’s largest software companies. It was a far cry from writing press releases and attending TV launches. 

Crazy, yes. A step back, maybe. But I was smart enough to know that I was going to get a better business education on the job than sitting in a classroom — from whom, other than my boss, I wasn’t sure.

And then it happened. Not long after I started, I met a two-star rear admiral and a three-star lieutenant general (both recently retired) who worked alongside my boss, and I instantly gravitated towards them.

Maybe it was their confidence, humility and insanely cool stories about flying fighter jets or jumping out of airplanes. Or maybe it was the calm and focus they were able to project when the going got tough. They were special and I knew it. 

I remember thinking that this career change might actually work.

Leadership school

These individuals were all intimidating to be around. Each person — responsible for running huge organizations and the Military leaders who had commanded tens of thousands of service men and women over their careers. They inspired, motivated, and got results. 

Lisa DeMille with mentors (clockwise) RADM Ed Allen (Ret.) and Kevin Fitzgerald. Pictured with former U.S. Senator Max Cleland.

To me, they were the very best and I wanted to be just like them. I pummeled them daily with questions about why this and why that — and they answered everything. They always treated me like I was a part of the team. They valued my ideas. They showed me respect, kindness and generosity.

And what was really great: They didn’t care that I was a woman, which I have had the displeasure of dealing with in my career — more than once. They often reminded me that we all get dressed “one leg at a time.”

Each of them was funny in their own way — especially the admiral — who’s wicked sense of humor used to get me in trouble in meetings for laughing at something he intentionally did or said about someone that he perceived as “not getting it.”  Humor, as I learned, is a critical part of getting people and teams to relax and refocus especially in hard times.

Early on, I’d often get intimidated in meetings because, as an executive assistant, I was usually the lowest-ranked person in the room. They frequently used this as a learning experience — “encouraging” me to sit at the front, be the first to speak or volunteer an idea. They pushed me and believed in me even when I didn’t believe in myself, and they taught me to recognize the collective team’s input — not just the person with the biggest title or longest tenure.

Leadership lessons from the posse

Over time, I learned:

  • Leadership is earned.
  • Treat people with compassion, decency and respect.
  • Show up every day and be your best. You will get it back tenfold from your team.
  • It is not about you. 
  • Be humble.
  • There is not one, single star of a team. The team itself is the star.
  • Know when to be a Mother Hen, Enforcer, Coach, Player or Teammate.
  • Levity is a good thing — have fun and make fun of yourself if warranted. Your team does.
  • Find the good in people — and promote and expose it. Work on the other issues on the side.
  • Have fun. It takes no more time to see the good side of life than it takes to see the bad.
  • If you decide to run with the ball, just count on fumbling and getting the *$#& knocked out of you a lot, but never forget how much fun it is to be able to run with the ball.

Over the last 20 years, we have remained in touch — and I call on these leaders often to help me navigate my course. I consider myself exceptionally lucky to have had these experiences and be able to bring these lessons to my job and to my team, whom I now “encourage” to ask questions, sit at the front, and challenge and push themselves.

I believe in them as others have believed in me.

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