Best Practices: Dana Cowin Knows What You Should Be Doing, and She's Not Afraid to Tell You

Editor's note: We could all use a little inspiration and light during these strange days. Enter Best Practices, an F&W Pro interview series where we share how leaders and creatives are facing unprecedented challenges head on during the pandemic while still growing personally and professionally.

For 21 years, Dana Cowin was the editor in chief of Food & Wine. During her tenure, Cowin navigated the magazine from a paper-bound monthly into new digital spaces. She oversaw the launch of foodandwine.com, and helped F&W carve out out an identity on social media, in video, on TV, and in in-person events. In sum, she created the footprint of the dynamic brand I was fortunate to join in 2017 when I took the helm.

Since she left Food & Wine in 2016, Cowin — one of the country's leading tastemakers — launched a consultancy for brands, advising companies like "farm-fast" concept Dig. Once an editor, always an editor; she leans on her nearly 30 years of editorial expertise to guide business leaders.

"The strength of an editor is understanding the trends, the market, and having a strong sense of intuition," Cowin says. "What makes a great story? What are the elements of a story that are inside of this brand we're working with? Who is the consumer, and what do they care about? What does the brand look like, taste like, and feel like? Or how do I feel when I'm in that brand's space? Those are some of the questions that I, as an editor, would ask."

For years she's mentored editors and chefs quietly behind the scenes. (She calls giving advice "being bossy.") Cowin brings some of these conversations to the fore with her Speaking Broadly podcast, and through a coaching business she created to advise women in the hospitality industry. In this role she helps her clients identify "the dreams that are locked inside themselves and the devils that are holding them back."

Her first job after Food & Wine was as creative director for a restaurant group. It didn't go as planned. Now she references that setback when coaching others.

"I really have a lot of empathy for people who feel their competence has been crushed," Cowin says. "I also believe that a balloon can be reinflated. And so in working with people I really believe that I can be the pump that helps someone as they're inflating their confidence that's been deflated."

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A lifelong New Yorker, Cowin has a longstanding commitment to her community. She's on the boards of Hot Bread Kitchen and Food Education Fund, as well as Women in Hospitality United and the Food Council of City Harvest.

Recently, I had the honor to catch up with Cowin for a conversation about mentorship, creativity, and what's changed in the hospitality industry since she left Food & Wine five years ago.

The following interview is edited for length and clarity.

You're wearing several different hats right now professionally. What does a typical Tuesday look like for you?

Every day is a mixture. It involves a lot of time on Zoom and talking to people because I'm advising companies and startups. I'm advising fast-casual food brands and advising founders on everything from menu development to strategy to PR and marketing.

I also coach individuals. I'm a creative guide and partner to help people. It's 100% women in hospitality now. I help people figure out what to do next. Some people feel like they have 9,000 choices and how can they choose? They want a creative partner to explore options. And there's many, many variations of that.

With the world open as it is, my Tuesday also always involved some type of food, adventure, and exploring.

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And there's some amount of not-for-profit. I'm helping with the Food Education Fund. Today I was reaching out to Yannick Benjamin from Contento. He is a super inspiring sommelier who opened a restaurant in Harlem. And he's a wheelchair user. I'm helping him with this accelerator program. There is a woman who wants to create a food truck that is wheelchair accessible because she also is a wheelchair user. So part of my Tuesday would be putting these two people together and saying, "There's a lot of wisdom to be shared here." So I think that it's that type of mix.

I get to take a walk out in Central Park as a part of my day. I always try to get something like that in.

So much of your work in editorial was marrying new data with your experience and gut-level instincts. Are you doing the same when you're advising companies?

The strength of an editor is understanding the trends and the market, and having a strong sense of intuition. At this point for me, in media of one kind or another for 30 years, it's drawing on that. What makes a great story? What are the elements of a story that were inside of this brand we're working with, who is the consumer, what do they care about, what does it look like, what does it sound like, what does it taste like, what does it feel like, how do I feel when I'm in that space? Those are the questions that I as an editor would ask.

But in helping brands, the structure of the question and the result is different because it is funneled through food that people can eat, or a restaurant that people can walk into, or a menu that's online. But so much of the storytelling and the rest of it is very similar.

You launched your Speaking Broadly podcast in January of 2017. And that came into the world before the #MeToo movement flipped parts of the restaurant industry upside down. Now there's reckonings and conversations happening about race and gender and equity in the workplace. What does this conversation look like for you now with the folks who you're talking to on the podcast or the folks you might be advising or coaching versus four years ago?

For the podcast I interview women in hospitality about their strengths and what they've had to overcome, their successes, their challenges. There's so much more awareness and attention focused on gender equity, social justice, that I think what's changed is the public conversation. I don't think that companies have changed as much as we would like.

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The people I interview have achieved a level of expertise. They're aware they're often able to make the rules. So I feel like it's been really exciting to see how people are setting the agenda to have gender equity, racial equality in their workplaces.

For the individual, everybody's story is different. If you've been subject to harassment, the way that you feel about the work probably hasn't changed from that moment. But the world is more open to it because people now realize that the problem is endemic. It's not just your problem.

I'm thinking about the language we use as storytellers. When I was coming up as a restaurant cook and early on in my media career, there was a focus on celebrity chefs and "rock star chefs" and that's language we don't use anymore. Did you see the vernacular changing towards the end of your tenure at Food & Wine?

I think I saw a little bit of a change, but I feel like it's changed so much more in the five years since I left. Also, it's not just the language. It's, "What do we appreciate?" "What is the most important thing about the person who's cooking your food?" And I think that conversation has changed so substantially, language or not. That chef, that personality has an effect on an entire ecosystem. How are they treating people in the kitchen? What are they doing for their community? What is their stance on sustainability? How are they treating the earth? And in addition, how great is the food?

I think about this in the context of the Best New Chef accolade. If you trace the past decade of chefs who have earned the accolade, you can see the Food & Wine team begin to lift their heads up from the plate into the restaurant and begin to look out into the world to see what a leader's worldview is. Leadership becomes a key driver of who earns the accolade.

Initially we thought about just cooking. Now we transition to chefs who realize they can use their platform. They are leaders of their team. They're leaders of their community. They're the leaders in a larger conversation, and through their food, they can express hopes and dreams and what makes an outfit like Best New Chef at this point so valuable, because it points out the entire universe, not just that their corn soup is better than anyone else's corn soup.

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Tell me about your role as F&W Scout on Instagram. I love your enthusiasm and delight in sharing with your audience something new, whether it's a flavor, an ingredient, a talent.

I do have very genuine enthusiasm and it bubbles over. I go to these meals and I'm so excited to try something new, and I want to share it. I think that this quest that I've had for decades now to explore the entire world through food.

You have quietly mentored so many people behind the scenes. And now with your coaching, this mentoring is becoming more visible. Who is an important mentor to you? And what do you get out of the mentor mentee relationship?

I like giving advice. I'm kind of bossy and I kind of think I know what you should be doing. So I'm mentoring, but I'm also kind of bossy.

Though he doesn't know it, the person who is my mentor because I study his every move is Sean Feeney, the co-founder of Lilia and Misi. We were in touch pretty much every day of the pandemic with ROAR trying to figure out ways to improve the lives of restaurant workers. And we're also on the board of something the Food Education Fund, which is a not-for-profit that supports Food and Finance High School and other culinary focused high schools in New York city.

I love Sean's restaurants. We had my daughter's birthday at Lilia. So I studied this man. How does he get so much done? He has a green pen. In all my years in media, I was doing it with a purple pen. Sometimes Sean will be in a meeting in Zoom, his head is down, that green pen working. He's not necessarily participating. And then he picks his head up and he has a completely fully formed thought. He's thinking, 'What do I want to bring to this organization? Here's the five things I'm committed to. What are you committed to?" He always has time. The man has multiple businesses, but if you need Sean's time, he'll find time, which is a huge value and something that I pride myself on as well. If you need my time, I can find time for you.

I love the mentor-mentee relationship, and this is especially true now with coaching 100% women in hospitality. I have so much to learn from the people that I'm mentoring, because everybody knows about some piece of this world more than I do.

You wrote a piece back in 2008 where you said that one of your friends called you "pathologically positive." What are a couple of words that you would use to describe yourself?

Pathologically positive is a pretty good one. I'm a cheerleader. I'm an empath. I'm a seeker and an adventurer. I have that restless sense of always wanting to try something new. So I think those are some. I can be incredibly critical and direct. Yeah.

In your cookbook Mastering My Mistakes you boldly admitted that you don't know everything. Because we're all supposed to be so fully formed and perfect whether it's in the kitchen or not. What's a big failure or setback that you had personally or professionally that you used as a major growth moment?

When I left Food & Wine I was so ready to go, but I didn't want to leave without a job. That just seemed silly to me. So I took a job as creative director at a restaurant group. The leaving wasn't a mistake, the job title wasn't a mistake, but once I was there I realized it was a big mistake. I had intended on leaving Food & Wine to do things I hadn't done before because I wanted to see what my next phase could be like. What could I do that isn't being an editor, which was the only thing I really knew. That wasn't the failure either. Taking a risk wasn't the failure. And trying to do something I don't know how to do wasn't the failure.

But that experience was awful. And I was questioned every day about what I knew and was I actually competent, and then my advice was ignored. So it was a failure of confidence. I hadn't had that experience in a long time. I stuck with it until I felt like less of a personal failure, and more like, "Oh, this situation isn't right for me." So yeah, I totally failed at that job and was very grateful to be able to move on and recognize what part of the responsibility was mine and that I wasn't really set up to succeed.

And is that something you've factored into your coaching and advice giving?

Into every single thing. Arrogance isn't one of my core qualities, but I really have a lot of empathy for people who feel their competence has been crushed. And I also believe that a balloon can be reinflated. In working with people, I really believe that I can be the pump that helps someone as they're inflating their confidence that's been deflated. The ability to recover is so important. To discover resilience is important. And also to not be critical of yourself. I could look back and say, "God, it was [foolish] to take that job. I should have known." And instead take the lessons of why that didn't work out and how I can be sure not to replicate that going forward.

When you're starting with a new client in your coaching business what's one of the first questions you ask?

Well, the very first one is what's your aim? What's your goal here? What do you think the challenge that you would like to address is? And I love the answers because they're all over the map. I want to be sure that I'm not making assumptions about people.

You're a New Yorker through and through. What's your relationship status with the city right now?

I am a born and bred New Yorker. I've only lived outside of New York for four years of college. It's a love affair. I was talking earlier about my love of discovery. There's so much to discover. I love walking neighborhoods. I love getting to know blocks. I love seeing the minute changes. It's a love affair with New York City.

What are some of the cultural things that have sustained you and fed your soul and empowered you to really keep going during the pandemic?

During the pandemic I began painting and drawing and reading more than I have read in years. One of my early jobs was being a reader for film and then writing book reviews, but I had stopped for such a long time. And I'm a huge fan of the New York Public Library app.

During the pandemic I started painting postcards. I've been drawing a self-help book. I'm now trying to teach myself to draw. How do you inspire others to keep going and what are the lessons that I've learned that I can share? I've translated those into things with paint and marker from the pandemic. I've loved having the time to do it.