An Interview with Leslie Pitterson

Leslie Pitterson is a communications and public affairs executive. A decade ago, she wrote the article that would inspire the creation of the hit television series Insecure. Since then, she has built a career leading campaigns and teams across media, finance and tech. Today, Leslie focuses on helping companies and executives tell stories about the next era of leadership. She works at Microsoft as Head of Communications for Business Development, Strategy & Ventures. Prior, she led the communications team for Google’s $80bn advertising business.

Where did you grow up?

Doing my homework behind the counter of my parents’ print shop in the Bronx.

What was your first dope accomplishment before becoming an adult?

My high-school gave me an award on graduation day that was about being kind. It had a fancier title than that because it was named after an alum but the jist was “thanks for being a kind person and not a monster” which was very sweet.

Toni Morrison or Alice Walker?

Toni.

What have you discovered about yourself during the pandemic?

How much leadership comes down to your ability to be grounded and self-possessed.

Why did you move to Harlem?

Grad school. I moved into a brownstone apartment within walking distance from Columbia and I’ve stayed in the neighborhood for 12 years since.

What is your favorite episode of Insecure?

Any episode that had Molly at her therapist’s office. I loved the scene in season two, episode two about magical thinking - how we get stuck in how life was supposed to turn out and what would be possible in our lives if we let our ‘should’s go.

What’s the best advice ever given to you by your father?

Don’t enter a negotiation you can’t walk away from.

How do you feel about creative side hustles?

I think they’re fine..I think maybe we’ve over-indexed on them though. It’s ok to have creative outlets that aren’t hustles. I make floral arrangements. It blisses me out. I don’t want to be a floral influencer. I just want to look around the house before a dinner party and see some dahlias. That’s all - and it’s ok.

What’s the best gift (tangible or intangible) you’ve received?

My mother bought a scarf from a flea market her first winter in the states after immigrating from Jamaica. She passed it down to me a few years ago and it’s one of my favorite pieces.

Popeyes or Chick Fila?

I’m good.

What would your superpower be?

Intuition.

Which music performer you’d pay top dollar to see 20 years go?

Whitney.

How do you self-care?

Therapy, good friends and lots of those hummingbird candles.

Who are you fangirling over these days?

Don’t fully know what that means but let’s say Jhumpa Lahiri to be safe.

Al B Sure or Heavy D?

Heavy D.