WW CEO Mindy Grossman: 'I joke that I'm an accidental CEO'

This story is part of the Behind the Desk series where CNBC Make It gets personal with successful business executives to find out everything from how they got to where they are to what makes them get out of bed in the morning to their daily routines.

Mindy Grossman has spent more than four decades building and transforming consumer retail brands like Tommy Hilfiger, Ralph Lauren and Nike: She oversaw Nike's $4 billion global apparel business and built Polo Jeans Company into a $450 million business from scratch.

She is also the CEO who made Home Shopping Network "cool" when she took the helm in 2006 by leveraging celebrity sellers like Jessica Simpson, Serena Williams and Sean Combs before taking HSN public in 2008.

Today, Grossman, 63, is CEO of WW (formerly known as Weight Watchers), a job she got in 2017 — with major share owner and board member Oprah Winfrey's personal seal of approval — hired to turn struggling diet company Weight Watchers into a health-and-wellness brand.

Since taking the helm, Grossman reformulated WW's food products to remove artificial ingredients, created partnerships, like with popular meditation app Headspace, and she even hit the road with Winfrey for the '2020 Vision: Your Life in Focus' tour, which ended right before the pandemic. In that time, WW subscribers climbed from 3.2 million in 2017 to about 4.7 million in September 2020, and annual revenue went from $1.3 billion in 2017 to $1.4 billion in 2019.

Despite Grossman's accomplishments, and several rankings at Fortune and Forbes as one of the most powerful women in business, she admits none of it was part of her original plan.

"I joke around that I'm an accidental CEO," Grossman tells CNBC Make It.

Growing up in Long Island, New York, Grossman thought she would become a lawyer. But after college, she had "an epiphany" one morning and abruptly decided to quit law school and move to New York City.

Here, Grossman talks to CNBC Make It about being adopted, finding her passion, and about her daily routine and how she handles mistakes and stress.

My parents tried, tried and tried but they couldn't have kids. My father worked nights in the produce business in St. Albans, Queens. So, they didn't have a lot of financial security and they could not afford adoption.

One night, my dad's boss Charlie, who loved him, handed him an envelope, and in the envelope there was a check. It was the money to pay for a lawyer for adoption.

I remember being told from the time I was able to understand words that I was unique and I was special. I was chosen.

As a little kid, I was very serious and not in a negative way. I had fun and I had laughter. I was a dedicated student but I also kind of was into friends, sports and cheerleading.

But [the experience of being adopted] instilled in me this belief that I was special. I had been given this incredible family, this gift. The most important thing for me to do was to use this gift for others.

Growing up, I didn't even know what a CEO was. I really thought I was going to become a lawyer and then ultimately a judge.

The reason for that is when I was about 4 or 5, I had to go into court for some finalization on my adoption. And I remember being in the judge's chambers and very unusually, the judge was a woman. I remember saying that I want to be that person, because look at what they are doing for people's lives.

Then in college, I realized that I wanted to be in business. But it was never like I want to be a CEO. I think that came over time.

What I love [about business] is conceptualizing the business case, the strategy and the outcome. I love leading cultures, people and organizations. And I love the creativity of business. And I think that's where the passion really came.

A lot of people know I describe myself as a resilient optimist. I always look forward. My favorite word in life is "bashert," which means everything is meant to be in Yiddish. I don't look backwards.

I'm focused and purposeful. And I think that's very important. When I've made decisions throughout my career, they were with a lot of forethought and study and belief.

And no matter what I've done, I care deeply about people. And when I give advice to this day, I say one of the reasons I've had my success is I focus on making other people successful.

I am definitely someone who likes rituals.

I get up every morning at 5:30. I get my coffee. My husband and I have a contest every morning, who can do The New York Times crossword puzzle the fastest. He's a mathematical physicist with a law degree, so I'm very competitive with him.

[Throughout the day] I've gotten better at making sure I have breaks, [like] to see my grandchild. I think part of what people are going through during this time, especially working from home, they haven't had that normal process of breaks in the day.

I try, for the most part, not always, but I do try to have dinner with my family and, believe it or not, watch "Jeopardy."

Then if I have to, I'll work for a few hours.

I am one of the most vigilant WW members that exists. I live it. I don't just run it. I have tracked every day for three years.

I wasn't always diligent about my weight. You can look at pictures of me over the last 10 years and I'm the healthiest I've ever been. And I say the healthiest because it's got nothing to do with a number.

I'm a very avid cook. I've been cooking more over the past year [as one of] my releases.

Then at least four times a week, if not more, I put a workout on my schedule. I'm a walking fan, I'm a Peloton fan. I just had a Mirror installed. I think it's a critical part of a release for me.

My daughter has been really pushing me to be a little better on the meditation and that side of the equation. So that's one of my focal points for 2021.

You have to find things that bring you joy and that allow you to disconnect or that put you into quietude.

I think humor is really important. I am a voracious reader and that definitely helps me. I'm a huge Adam Grant fan. "Give and Take" was one of my favorite books in terms of how I define leadership.

I need to find that quiet time where I can decompress even in the midst of a storm. I try and bring whatever level of calm and focus, and even during this time, with leading an organization. I always say to people, "I'm not just the CEO, I'm the chief crisis officer, the chief communication officer and the chief hope officer."

I tend to focus on the things I can control. I try to find some time for myself to at least process the things that are happening to where I can calmly understand how to move forward.

I made a lot of mistakes. There have been many times that the outcome was not exactly what I would have wanted, whether that's personal or business. My whole approach is ... what did I learn from it? And how am I going to move forward?

What I pride myself on is that I don't pretend that things are just going to get better. I move quickly when I identify that something that I really felt was the right thing, might not be. And I'm very transparent about that, particularly within the organization.

In January 2019 when [we] relaunched [WW], I mean, it was a massive rebrand launch. And we didn't drive the business at the levels that we thought we could. We immediately pivoted. But we never looked backwards and doubted the strategy of what we were doing. We just needed to finesse the execution.

I think that the people who are respected are the ones who own, identify and then create the path forward.

This interview has been edited for length and clarity.

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