Jenn’s Fashionpreneur Column: How to Interview

In the latest installment of Jenn’s Fashionpreneur column on, she gives the dish on how to interview people and what’s most important to look for.



A few months ago I read a post from Ben Lerer, the CEO of Thrillist that fundamentally changed how I interview. If you’re too lazy to read it, here’s a summary: when Ben started his now very successful company, he was too easy on candidates and hired anyone who showed enthusiasm for Thrillist. As a young leader, Ben lacked confidence for why someone would want to risk it all and work for him. Since then, he’s done a 180 and looks for people who are willing to sacrifice to be on his team.


As CEO and co-founder of Rent the Runway, I often find myself in the position of interviewer, and it is a role I take very seriously. I never imagined two years ago when starting Rent the Runway that the vast majority of my time would be spent on recruiting talent, inspiring and coaching our team and creating a culture that our team is proud of. But now it makes sense. 100% of Rent the Runway’s success thus far is due to the incredible team we have; the right talent can transform a company from good to great, and can change a job into a family. My goal when we launched Rent the Runway was to create an environment that made me want to get out of bed in the morning a little quicker. It is so important to me that every single person on our team feel like a founder of Rent the Runway and LOVE their time here–which is why interviewing is so important. Not everyone is going to blend with Rent the Runway’s culture and not everyone will exhibit the values that make Rent the Runway an amazing place to work. While it is important to modify your interview tactics to the environment in which you work, here are some guidelines I have followed in building the team at Rent the Runway.


Look for “an appreciation chip.” Sure, maybe it’s simplistic, but I believe there are two types of people that walk this planet: people that are negative and complain about the circumstances of their life and others who appreciate what the world has given them and view every single day as an opportunity to be happy and positive. Now listen up: this is not a Pollyanna philosophy. Having dealt with many difficult situations in my own life and family from cancer to autism, I understand that life (and work) is hard. The type of person that I’m looking for at Rent the Runway is one that can look at all the things that have happened to them in their life and consider themselves lucky; they appreciate their relationships, their family, their time working with incredible people, and they take time to have fun and enjoy. Appreciative people bring positivity to every interaction–a quality that is critical at a start-up. Imagine how little Rent the Runway would have accomplished thus far if everyone was always focused on what we can’t do instead of what we can. I ask every candidate I meet “How lucky do you consider yourself to be?” and then I listen to how they talk about their own life. Their answer is more important than ANY relevant business experience they may have.


Culture over experience. While a candidate’s education and previous job experience is certainly important, being smart and capable is pre-requisite to getting in the door. Once you’ve cleared up whether someone can do the job, it’s critical to assess how they will do the job. How will they play with others? Will they make the people around them better and the culture richer? I pay a lot of attention in interviews to the candidate’s personality and if they will fit in with the unique culture of Rent the Runway (dream big, be scrappy, learn from mistakes). Unfortunately, I haven’t always followed my own rules and it has come back to bite me hard. Six months after launch, I hired a VP who was great on paper and in the interview room–she had the right Ivy League education and prestigious company background. However, when she started, she began to treat the members of her team horribly, often berating them (and influencing some of them to leave). After I let her go, I realized how one bad egg has the power to spread poison into your environment and demotivate people who would have otherwise given their hearts and souls to the company. I look for Rent the Runway’s values via candidates’ answers to questions, their body language, tone of voice and through thorough reference checks I will conduct post-interview.


And back to Ben (Lerer)–Don’t sell (as much as you normally would). As a sales and marketing aficionado, it’s my first instinct to sell, sell, sell and use every superlative in the book for why Rent the Runway is amazing. But, that’s not my whole job as interviewer and often my selling can occupy a lot of the airtime that would otherwise be used to get to know the candidate. A candidate is responsible for consistently communicating why they are dying to work at your company, and how they are going to make Rent the Runway an even more amazing place to work. Just as I tell my girl friends not to settle for a relationship with any man who will date them, I often remind myself that there will be a lot of frogs you need to interview before you find your prince (or princess) charming.
- Jenn