Almost three decades ago, Denise Pickett walked into the American Express office in Toronto to submit her résumé to the receptionist for an entry-level marketing position. Today, she’s the president of global services at the company’s headquarters in New York, and oversees more than 25,000 people around the world. She’s basically a poster child for climbing the corporate ladder — even though she actually turned down promotions on multiple occasions, including one right after she returned from her third maternity leave. Pickett talked to the Cut about saying no to new friendships, the trick to giving “constructive” feedback, and copying her favorite bosses.
Did you always think of yourself as an ambitious person?
I always worked hard in school, and my parents both worked, so I knew what it took to be successful. But I think it was other people’s encouragement that catalyzed my own ambition early in my career. When I was an assistant, my manager said to me, “You’re going to be country manager someday.” That’s the kind of thing you never forget, obviously. It made a big impression. And years later, I subsequently did get that job.
What do you think made you stand out? I’m sure that there were a lot of other young, ambitious people at the company, too.
I always focused on acknowledging other people. I really believe that being ambitious for other people is one of the most important things you can do for your own career. So I started paying it forward early, and copying the things other leaders did that made me feel good. I think there’s a relationship between confidence and ambition, and giving other people a confidence boost is really powerful.
How do you do it, in a way that comes across as sincere?
I’m big on handwritten notes. Twenty-five years ago, someone I looked up to wrote me one at the end of the year telling me how he saw me grow. I still have that note, and it felt so good to receive it that I started writing them myself, to acknowledge and recognize people. At that time, handwritten notes were more commonplace, but now, they’re much more rare, which means they’re even more meaningful to people. I think my all-time record writing notes is 278 in one sitting.
So you must write, what, thousands a year? When do you do it?
Sometimes I’ll do it when I’m watching something on TV, or listening to music. I have 25,000 colleagues around the world, and I do a lot of visiting to our operating centers. As I’m traveling, I’ll also write notes to acknowledge the people who presented while I was there.
And I don’t just write to people who work for me. Whenever I’ve gotten a promotion or something good happens to me, I’ve sent a note to someone who’s made a difference in my career. Which, especially in the past, has felt a little bit risky if that person was very senior. I remember the first time I wrote a note to the president of the company, years ago, and wondering, “What is he going to think about this?” But he was touched.
As a boss, how do you give people feedback in a way that encourages them to be more ambitious?
If I know someone has a big presentation or something coming up, I’ll send her a text or call her beforehand, and I’ll say, “You got this, you’re going to do great.” And afterward, I’ll give constructive feedback, like, “You’ve got to speak up, because it’s hard to hear you.” I think moments of acknowledgement aren’t just about, “You’re doing a great job.” They’re also about, “I know you can do better.”
Have you ever gotten pushback for your ambitions?
I’ve actually felt the opposite. Sometimes, especially early in my career, I felt the gentle nudge of, “You should do this, you should pursue that, this is a great opportunity.” And I generally moved quickly, but sometimes I knew that I had to push back because it didn’t feel like the right time.
I heard that you turned down a big promotion once, right after you got back from maternity leave.
Yes. When I was a VP, I was offered a pretty big promotion to the next level. It was my first chance to run a business. But I said no, because I had three children under the age of 7, and to be successful at the job, I’d have to travel 75 percent of the time. It just wasn’t going to work. That’s a decision I’ll never regret. In that moment, the right thing for me was being ambitious about my personal life. Being ambitious isn’t always about climbing the corporate ladder. It’s about being your best self across the spectrum of things that are meaningful to you. You can’t make a wrong decision if you follow that compass. You just can’t. So while I would say that part of being ambitious is taking risks. I don’t mean just saying yes — I also mean risks with saying no.
What’s something you’ve had to say no to in your personal life, because it just didn’t serve your ambitions?
This might sound strange, but probably adding more friends. At a certain point I had to say no to expanding my friend network because I knew I wouldn’t be able to do justice to the way I like to maintain my friendships. So I’ve had to be super careful about expanding my friend network, because I want to be able to manage the friendships I already have.
What’s a big risk you’ve taken, for the sake of your own ambition?
I moved my whole family to the U.S. from Canada a number of years ago. That definitely fell in the high-risk category. It was the trifecta: I got a promotion, I went to a new market, and I went to a new business. As for moving my family — I wanted my kids to have different experiences. I felt like my kids had led a good, but perhaps a little bit of a sheltered, life. And so a move to a different country, and the adjustments that come with that, was going to be a positive thing. Of course, for the first little while, it was tough. You move a teenage girl, going into high school — that’s hard. But I’m really proud of my kids.
You took a pay cut when you took your first job. Is that something you’d recommend as a career strategy, overall?
It was early in my career, and I hadn’t been very passionate about the role I’d had at my previous company. I think when you’re trying to find your career niche, you want to find something to be excited about. When I joined Amex, I wanted to try marketing, and I had to take an entry-level role because I had no experience. But I was living at home with my parents at the time, so it was easier for me to make that decision. I think it’s better to chase skills, not levels. If you diversify your skills, and you get experience, the levels will come. And at some point that leads to financial independence, and that’s great too.