Give Phoebe Robinson the Title She Deserves: Boss

Mention “The Devil Wears Prada” to the comic Phoebe Robinson and she’ll lean forward and tell you she has some opinions. The real villain in the tale of an ultra-demanding fashion magazine editor and her assistant is the assistant’s boyfriend, played by Adrian Grenier, for complaining when she has a work event. “Do you know centuries of women stood by their men pursuing careers?” Robinson said over lunch. “Adrian, calm down.”

As for the title character — Miranda Priestly, the Anna Wintour-type boss — Robinson, 37, has more mixed feelings. “It’s easier to judge someone from afar,” she said, adding that women of her generation had to be tough to get ahead. “At the same time, you don’t have to be a monster.”

In a time when pop culture and the news are filled with portraits of bad bosses, Robinson has been thinking a lot about what makes a good one. In the past few years, she has evolved from a hustling stand-up into a mini-mogul with a staff, a production company and myriad projects. This year alone, she released a Comedy Central series, “Doing the Most With Phoebe Robinson”; shot her debut hour special (“Sorry, Harriet Tubman,” premiering Oct. 14 on HBO Max); started a book imprint, Tiny Reparations; guest-hosted for Jimmy Kimmel; sold a half-hour sitcom; and wrote her third book, “Please Don’t Sit on My Bed in Your Outside Clothes,” which is, among other things, a primer on leadership. If that’s not enough, she’s in the process of moving.

“It’s a lot, not going to lie,” she said, pointing out that her career models have shifted from comics like Wanda Sykes to multihyphenates like Reese Witherspoon and Mindy Kaling.

Robinson’s style has always been down to earth, self-deprecating, with proudly basic music taste (U2 is a lodestar). Her instinct was to be the cool boss, she said, but the uneasy looks on her employees’ faces after she asked them to go bowling on a Friday night taught her a lesson: “I was like: ‘Right right right right right, I get it. If my boss asked me to hang out on a Friday I’d be like, no, I see you every day, I’m good.’”

The first time I saw Phoebe Robinson was a decade ago. She had been doing stand-up for a couple of years, typically in vests, jeans and a T-shirt. “I dressed so nothing would signal I’m a woman,” she said, adding that she was hyperaware of being the only female comic in the room. “I was so insecure and nervous.”

Even then, she had an ingratiating voice that cut through the clutter of competition, often playing with language, tweaking words, showing signs of a literary bent that would eventually lead her to publishing. When I reminded her of a joke she told about movies that cast handsome people as rapists, she cringed, saying she would do that in a more nuanced way now. At that moment, the sunlight shifted and she grabbed her sunglasses. Before putting them on, she said: “I don’t want you to think I’m doing this to look cool.”

In early August, a week before shooting her new special at the Brooklyn Botanic Garden, Robinson walked onstage at Union Hall in a headband and comfy dress. The Delta variant had forced audiences to put their masks back on and she wasn’t hearing the explosive laughter that she had only weeks earlier, even though the crowd immediately responded when she started talking about her relationship, which has become a regular part of her act. “I’m the Rosa Parks of the bedroom,” goes one line aimed at her British boyfriend. “I’m not getting up for any white man.”

A week later, Robinson said she was too in her head in that show, that she needed to remind herself to have fun. “It’s hard to stay in the moment for someone like me who is always thinking about the next 20 moves,” she said by phone.

Robinson had done a chunk of material about the difference between her 20s and 30s, including one bit about being more concerned with frivolous things earlier, like shaving body hair, which she did so much, she said, “that she didn’t read a book for 10 years.”

Now she’s an author and publisher who tries to read a book a week. “I miss that innocence a bit,” she said, explaining that she didn’t have to worry about her employees or brand back then. A few years later, her profile would grow thanks to a regular show with Jessica Williams called “2 Dope Queens” that moved from small rooms to HBO. In the years since, she said, their paths have diverged. “It’s one of those things where you meet for an amount of time and then you grow in different ways.”

A multitasker at heart, Robinson has juggled writing, performing and podcasting. She even recently joined Michelle Obama on her book tour, interviewing the former first lady, a major career turning point for Robinson, one that also provides the set piece closing out her new special.

An imprint that would let her champion writers of color had been a longstanding dream that Robinson pitched over the pandemic. She said her first book, the 2016 best seller “You Can’t Touch My Hair,” was rejected by every publisher except Plume (which now runs her imprint), and the reason she heard was that books by Black women don’t sell. That stuck with her. Following the September debut of “Please Don’t Sit,” Tiny Reparations has two releases set for the spring, both debut novels by authors of color: “What the Fireflies Knew,” by Kai Harris, a coming-of-age story, and “Portrait of a Thief,” by Grace Li, about an art heist. “I don’t want to read trauma all the time. That’s something I have been particular about,” Robinson said. “I really want hopeful stuff.”

“Please Don’t Sit on My Bed in Your Outside Clothes” is filled with thoughts on management and work, the product of an immersion in business books, podcasts and personal experience. The book is in part a response to the absence of Black women’s perspective in this genre. She writes: “Where’s ‘Lean In’ for us?”

Robinson calls herself a “reformed workaholic,” but she’s not short of plans: an idea for a romantic comedy, a talk show, specials she would produce and, perhaps the most challenging one, a two-week vacation. Meanwhile, she must manage a growing business. With the pandemic, people are questioning how they work, and while Robinson understands balking at excessive hours, she insists there’s a middle ground that involves working more efficiently. She has cut down on meetings, for instance. “I love Zoom but I don’t need to see your face,” she said.

Robinson said she knew that stereotypes about Black women might get her judged more harshly, but she had learned that one of the hard things about being a boss is asking your employees to do things they don’t want to do. “As someone who does comedy where you want everyone to feel good, you’re like, oh, I’m the problem?” she said, laughing at herself.

Miranda Priestly isn’t as far from her as she used to be. “It’s really tough to be a boss,” she said, “because you have to accept you are going to piss people off.”