Fashion Designer Rachel Roy on Being a Leader

Some business leaders achieve success by the book: Armed with an MBA, they develop a meticulous business plan and follow a pointed trajectory.

Others, like fashion designer Rachel Roy, make their own path. Roy learned to manage from the ground up, using outside-the-box ideas to build a tremendously successful company — and rack up countless accomplishments.

Rachel Roy
Courtesy Rachel Roy

She’s been named a member of the Council of Fashion Designers of America and one of Mattel’s 10 Women to Watch. She earned a spot on Vanity Fair’s Best Dressed List and received numerous awards from organizations like the Accessories Council, AdWeekMedia, and the La Jolla Fashion Film Festival. A featured columnist for InStyle magazine, contributor to Yahoo and the Huffington Post and a panelist for the Democratic National Committee, Rachel Roy dresses everyone from First Lady Michelle Obama to Gwyneth Paltrow. She’s also an outspoken advocate for creating sustainable employment opportunities for artisans in developing nations.

We sat down with Roy to talk about her approach to leadership, how to tap into your intuition, and what techniques to use to get what you want — even if all you keep hearing is “no.”

What does leadership mean to you?
Essentially, it’s to inspire people to be risk takers. A business will be so much more successful when authentic risk is taken — by that I mean risk you actually believe in, that inspires you personally. If you shut your eyes and don’t talk or think but simply feel, what does that inner voice tell you?

I inspire my staff to take risks through my actions. For example, providing jobs is very important for me, so I outsource certain styles to artisans simply because I would rather hire them than a huge factory in Asia. When I first started doing that, years ago, I had to pave the way because in the Third World they are not taught manufacturing. But because of my perseverance — or what some might call stubbornness — I made those programs possible.

How did you learn to be an effective manager?
In the beginning, I thought all I needed was to check the boxes for things that had to be done daily. I thought I had to keep the ship running, and that the buck stopped with me. I would take ownership of every single thing in the business, from the voice we have on our answering machine to deciding what time we are going to start shipping.

I never took management courses in school, but I’ve always been curious about leadership and am fascinated by very charming speakers, like Steve Jobs and Arianna Huffington. They have a gift that I will probably never have, but I enjoy being the student in those situations. I like listening, learning, and applying what I have learned to my life and my business.

My role as a leader is setting the story, the script, the tone, the standards, the core values, the mission — what are we doing besides just making clothes? — and then living it.

I also try to hire people with like-minded core values who are good at what they do. Even if you’re a kid just out of college, I’ll hire you if I see talent in you, a willingness to work, and a really happy energy. I will pass on someone super talented if their attitude and energy level doesn’t reflect someone I want to spend my incredibly long days and weeks with.

When did you know you were a leader?
When I looked around and saw that loved ones, acquaintances, customers, and strangers would not be willing to do things that I was willing to do. Being a leader takes risk, bravery, perseverance, hardship, confidence, kindness, and patience. Some people don’t want to call that kind of havoc into their life, and others really want to push for change.

I’m always willing to fight for what I believe in, even at the risk of losing my job or of people not liking me, or of having an uncomfortable confrontation day after day until what I believe is right begins to be implemented.

I realized that’s the real difference between a leader and someone who would rather live a quiet, simple existence — and that’s fine.


What’s the most surprising thing about being an effective leader that most people probably don’t realize?
Really good leadership is the study of human nature. Being able to quickly suss out how someone wants to be treated makes a world of difference. You have to have your antenna up. For example, if I’m working with two talented designers and understand that designer A is sensitive, whereas designer B is cool and lets things just roll off, then I know to sit down with designer A and take more time to talk about their designs than I do with designer B. Combining an understanding of human nature with a thought you believe in hard enough to work at day after day usually makes a great leader.

What is the greatest challenge you’ve faced when it comes to leadership?
My biggest challenge is knowing when to stop fighting for what I know to be right, and figure out another route to that destination. Say a factory is telling me a delivery can’t ship. I might fight it, threaten them, do whatever I have to do, but they still hold firm that they’re not going to ship it. That doesn’t mean I’m not going to send out those dresses, but if I’m putting energy in and not getting results, I have to decide at what point to stop pushing and go a different way. That’s where understanding human nature comes into play — you have to pick up on someone’s personality and identify who’s a pitbull and who’s all bark.

How has your management style changed over the years?
When I first started my company, I did it all myself, from the top of the totem poll to the bottom, because it was easier that way. As a business owner, I’d sometimes think, I can get a task done in five minutes instead of investing the hour of teaching that it might require to show someone else how to do it. But the more my company grew, the more I had to lead by inspiration to get the work done as opposed to doing it myself. At some point I had to start teaching in order to achieve the single vision I had from multiple people.

In what ways is your personality different when you are leading your team versus hanging out with friends and family?
I’m entirely different in my personal life. I want to relax and mind melt, and be really present for my children. I don’t have to inspire my kids the way I do my staff; I just have to be a good mom, do the things I say I’m going to do, and be fun.

What’s the biggest mistake you’ve made as a leader?
My biggest mistake is not taking enough time to lead. Thinking that when I get to work, I can go straight to my office, shut the door, and start knocking things off my list because it feels so good to get to number 16 and cross it off and keep going.

I used to have a partner that ran a billion-dollar company with four or five CEOs, and you never saw them on the floor, taking the time to walk, talk, and actually be a part of the team. What I’m lacking from people who are supposed to be leaders to me is what I offer to my people — what I need is what everyone else needs.

What would your team say about your leadership style?
I’ve actually been present when they’ve been asked this by journalists and what I hear, especially from female staff members, is that I show perseverance and determination, and never accept a “no” until I understand why it’s impossible.

It’s not that it has to be my way or no way, but if someone is telling me no, I want to know why. I have been in some really high-profile meetings with extraordinarily famous, smart people, and I’ll be the first to raise my hand and say I don’t understand. And I’ll see everyone look at me, and then a few minutes later other people will raise their hands and say, “What do you mean? I don’t understand.” I like being that example.

I’ve been laughed at in meetings, I’ve had CEOs of huge companies say, “I made a printout for a 12-year-old, for Rachel, so we can go over these bullet points for her while all the rest of you go over the real spreadsheet.” I am not at all insulted. Sure, I might not understand their technical language. I didn’t go to business school. But I’m the one with the business and they’re the ones working in a big corporation where they have to ask for permission.

I don’t have everything that I wish I had, and I’m still growing and learning. But I do know that being an effective leader boils down to how you treat people, and that you can inspire people by staying authentic and consistent to the story you want to tell.

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