Work Issues? Rent the Runway’s CEO Shares the *Right* Way to Complain to Your Boss

Hint: Don’t just rattle off the negatives.

By: Samantha Sutton
Photography: Weston Wells

With 2018 swiftly approaching, we’re already in that whole “new year, new you” mind-set. What stuff can we work on in the months ahead? What will our New Year’s resolution be? Well, if your own includes something about improving your wardrobe and advancing your career, then Jenn Hyman just might be the person to help. Not only did the CEO and co-founder of Rent the Runway create a company that keeps your “closet in a cloud” and your clothes forever on rotation, she’s also quite the inspirationand happy to share as much advice as she can.

After a quick trip to Rent the Runway’s NYC headquarters—partly to check out the sweet pieces included in its fashion subscription service and the fairly new $89-a-month RTR Update—we picked Hyman’s brain a bit. Ahead, the power woman shares how to properly give constructive feedback, go about handling work-related issues, and why you really can have it all (aka a great career and a growing family).


What did you want to be when you grew up? Did you always sort of have an idea for Rent the Runway?

“No, not at all. When I was much younger, I dreamed about being a wedding singer or a Broadway star, or a big-city dancer. Then, when I was in college, I decided that I wanted to be a journalist. So clearly, both of those dreams I had for my life have not yet come true. But there’s always the future.”

Do you ever get tired of being asked what it’s like to be a woman in business?

“I think I spend an inordinate amount of time in every interview—whether it’s for Forbes or Vogue—talking about what it’s like being a woman in business, as opposed to talking about Rent the Runway and the ability to have a wardrobe on rotation. I would rather just talk about Rent the Runway, because I think what we’re doing is revolutionary, and it’s changing the way that women get dressed. That being said, I understand that we’re at a very important time in history, where it’s finally coming to the forefront, across all industries, that it’s more difficult for women to succeed as leaders, as founders…even in the business world in general. While men start [their careers] at zero, women are starting at negative 50. They have to work harder to get to the exact same place. So I think it’s important to me to lend another data point to that conversation, because it’s true; it’s fundamentally harder for women, or people of color, or any minority to get to the top of their industry. And it shouldn’t be that way.”


Do you have any advice on how to give constructive criticism at work?

“I think when you have a trusting relationship with someone, you both know the feedback you’re giving is about their growth and development, and they feel like they could also give you feedback. It’s just a natural conversation saying, ‘Here are the things you’ve been doing that are awesome, and here are things that you could look to improve.’ I don’t think constructive feedback—I don’t call it criticism—is a bad thing. It’s a great thing. We all need feedback in our lives in order to grow.”

What’s the proper way to address an issue at work without sounding like you’re complaining?

“The same way that you would address an issue with one of your closest friends or your significant other. It wouldn’t be effective to just complain about all the things that they’ve done. There’s a way that you talk to someone you care about that’s more sensitive and thoughtful, where you’re trying to put yourself in their shoes. It could be an engaging conversation where blame isn’t tapped, and you’re trying to figure out the solution together. Where we can both change a little bit in how we’re operating and get to a better place. Starting from a place of positivity, as opposed to negativity, I think, is how you should give feedback in any aspect of your life.”


Since you’re so passionate about what you do, do you feel like you’re always working?

“I love it, so I don’t view it as work. Even if I was making zero dollars per year—which I was in the early days of Rent the Runway—I would still do it. Now, there are other passions I have in my life—my husband, my daughter, my family, my friends. But my passion for Rent the Runway doesn’t get in the way of those other passions. It’s not an either-or situation. You can have an incredible career that you’re passionate about and still build a family and still have great friendships and a stunning, adventurous life.”

Do you think people get hung up on the either-or thing?

“I think it’s easy to frame everything in life as if it’s black or white, where if you have a great career, it means you’re not going to have a great family life or social life. I just don’t believe that that’s the case. People in their life make choices based on how they want to spend their time, and everything is fundamentally in your control.”


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