You started as a freelance makeup artist. At that early stage of your career, how did you find clients and persuade them to hire you?

I approached networking as my full-time job. I knew I had to show my portfolio to the people who were hiring and, in a very short amount of time, “sell myself” as someone who really loved and believed in what I was doing and had talent and would fit into a crew. I was very young and wide-eyed and enthusiastic.

What were the most important lessons you learned when you launched your cosmetics line a few years later?

The most important was to follow my gut. Don’t put something on the market just because everyone else is doing it. Do what you think is right. I’ve made so many mistakes—who hasn’t?—whether it’s hiring people I thought would be perfect (who weren’t) to getting talked into products or categories I wasn’t sure of. As the company got bigger, I thought maybe I should listen to people with more experience. But I’ve learned that the best thing for my company is to do what I believe in.

You didn’t have any business expertise at first. How did you move up that learning curve?

I pretty much make things up. I mean: What is an entrepreneur? Someone who just dives right in and tries something and if it doesn’t work, tries something else. You don’t overthink it. You don’t strategise. You just do it. I started the business with partners: my husband and another couple. In four years we were beating Estée Lauder in our biggest store. They came calling, and we sold the company.

Other companies were approaching you, too. Why did you decide on Estée Lauder?

Because I fell in love with Leonard Lauder, and I trusted him when he said, “I want you to do what you’re really good at, and I’ll do the things you’re not good at. I promise that you’ll have creative control.” And I’ve never had a problem.

Is it hard to run your own brand within a big organisation?

There are hurdles—things you have to get over or around. When people give you their strong opinion, you just tell them, “It’s a really great idea. Thank you.” Then you go back and do what you think is right. Usually in big companies, there’s so much to do that no one really dwells on everything that’s discussed. And because the brand is growing, they don’t come back to me. They don’t insist; they suggest.

You moved out of corporate headquarters a while back. Tell me about that decision.

Yes, I was in the corporate environment, I think on the 45th floor, and I dressed like a corporate employee, wearing uncomfortable suits and high heels. I went to work and looked out the window that didn’t open, and it just never felt right. At some point when our business was flat, I said to the CEO, “I’m not really able to do what I want to do.” He said, “What would you do?” And I said, “I’d move downtown. I’d allow people to wear jeans. I’d have a creative, open atmosphere, where people want to be, and I’d put in a new president of my choice.” I did those things, and it worked.

Your official title is chief creative officer. What does that role entail?

The role entails everything that touches my artists and the consumer: developing products, naming them, marketing them. I rarely have a finance or operations meeting. I wave to those guys and give them a thumbs up, but I do all the things that I’m really good at and that I love.

You’ve always been known for being not just the name but the public face of the brand. You visit department stores, do TV appearances. Why is that personal outreach so important, and why do you think you’re good at it?

It’s probably my least favorite thing to do. The good news is my hair gets a great blowout. But to always be on is not easy, and there’s nothing worse than having the paparazzi call your name—“Bobbi, over here, Bobbi, over here”— while you’re holding your stomach in and wondering how you’re looking from the side and the back. And yet it’s important because I have a message, and I like to teach other women and empower them. That being said, I am a mother and a wife and have a foreign exchange student at home, so I’m really picky with what I do in the evening. The high-profile black-tie events have to be for a cause I really believe in or in honor of someone I’m close to.

You’re credited with starting the natural makeup trend, and many other companies have since copied your aesthetic as well as specific products. How do you respond to that sort of competition?

I’m overjoyed. Honestly, I’m never at a loss for coming up with something new, and in my mind, what I do is better, so I’m not afraid.

How do you stay innovative?

I’ve never had any issue with that. The problem is deciding what to do, because there are so many different ideas and only so many hours in the day and so much room at the counter. So I look for opportunities, I listen to the marketing team, and we make our decisions based on a lot of facts. In addition to being very visual and creative, I’m also super practical.

What happens when you miss a trend?

I listen to what the market is asking for and, if I don’t like the current form of a product, I won’t just put my name on it. I need to figure out why people want it and recreate it. I don’t need to be first. I just need to be best.

What kind of a boss are you?

I think I’m funny and very direct. I’m often incredibly busy, so I tell people the truth. One of my employees laughs at me because, when I don’t like something, I start by saying, “No offense, but..” Still, I have good relationships with my people. You either work for me a really long time, or you don’t last, because I am not your traditional boss.

You’ve been described as very hands on.

I don’t go into the lab and mix the products, but nothing goes out of the door without my 100% approval.

What do you look for in your creative talent?

I need people with really good energy, who share my aesthetic, and are fun, talented, and completely transparent and truthful. I cannot work with someone who says one thing and does something else.

Can you tell if someone is a good fit immediately, or does it take a while?

Unfortunately, it’s hard to know someone’s creative process from an interview, so I first try to work with people on a freelance basis. I start with a project and then extend it to a permanent position.

What are the key things you do to inspire and motivate your staff?

Tell the truth and appreciate what they’ve created. I’m the first to hug someone when they come up with a great new color or formula. I absolutely congratulate and give credit, because there’s nothing I do by myself except an interview. I also think our office is a really great place to work. We have an in-house manicurist, a kitchen with a smoothie bar and all sorts of healthy food, yoga on Mondays. I try to make it a nice atmosphere.

Where do you personally do your best work?

In the car. I commute to work with a car service, so twice a day I have an hour when I can do anything. I’ve written all eight of my books in the backseat. I come up with great ideas. Working with a team of people is one thing, but I find it difficult to focus in the office. To get work done by myself, I need to be in a car, moving. I’m great on airplanes too.

You talked about your family and the juggle involved in that. How do you manage it?

I started the company when I was pregnant with my first child, and he’s 24 now. There was a lot of torture in the beginning because I didn’t want to be away, didn’t want to miss his first steps. So I took my family on trips with me as much as I could. My husband is a businessman and an attorney, but he works for himself. And I had my own company, so we had that flexibility. Not everyone does. But I think you have to take it where you can. Make sure to schedule your kids’ first day of school, school holidays, sing-alongs, doctors’ appointments a year in advance. Do all those things, and hopefully you’ll be able to work for a company that respects that.

Why should executive women spend time thinking about their makeup?

I’ve never met anyone who doesn’t benefit from a bit of mascara, some blush, or concealer. For me, looking good doesn’t mean smoky eyes and a red lip. It could just be a little bit of eyeliner and foundation. I think most professional women, especially ones who are competitive and want to get ahead, take care of themselves and want to look good. Success requires experience, of course, but also confidence. You want to look and feel your best. If you can do that with no makeup, you’re really lucky.