get that money

How Awkward Can It Get When Your Friend Becomes Your Boss?

Photo: Joos Mind/The Image Bank/Getty Images

Get That Money is an exploration of the many ways we think about our finances — what we earn, what we have, and what we want.

I met Julia on the first day of college. We were assigned to the same orientation trip — backpacking — which neither of us liked, giving us an immediate bond. Over the next four years we smoked weed and baked cupcakes together in the dorm kitchens, commiserated about the annoying kids in our writing classes, and drove from our sleepy campus into L.A. so she could review restaurants for the school paper. After graduating, we moved to different cities. She worked her way up as a food critic and editor while I went to grad school and muddled along as a freelance writer. Then, in 2017, she became my boss.

It didn’t come out of nowhere. I’d done some writing for the magazine where she worked, which turned into a freelance editing gig. Then, a few months later, a full-time job opened up and Julia encouraged me to apply.

I didn’t hesitate when I got the offer — I really wanted the job — but I immediately second-guessed myself afterward. Wasn’t “don’t work for your friends” one of those rules that people with real jobs knew to follow? Would this be awkward? Would it ruin our friendship, affect my salary, or hurt my career? (Later, Julia told me that she had no concerns about hiring me, although her dad did: “He was like: ‘Julia, you really never know what’s going to happen.’ Now, he always asks, ‘How’s Amanda doing at the job?’”)

It’s one thing to be friends with your boss. It’s another thing to be friends with someone who becomes your boss. Suddenly there were new situations to navigate, including the issue of money: When you go out to lunch, do you split the bill? (And when can you expense it?) What happens when you want a raise? What happens when you don’t get that raise?

When I asked other women about their experiences working for friends, I heard plenty of cautionary tales. Like Lynn, whose friend-turned-boss hired her for a long-term marketing project. “At first it was fantastic. We worked really well together, and I did some of the best work I’ve ever done,” she said. But after a couple of years, she noticed that her friend-boss would repeatedly evade her requests for well-earned raises. “I had to ask multiple times, and often I’d get the brush-off,” Lynn said. “She would generally follow with some really harsh criticism of my work, basically telling me that I wasn’t worth it. And because we had this connection outside of work, she could manipulate those emotional ties.” Eventually Lynn quit, and she and her former friend haven’t talked since.

Samantha, who did some freelance work for her friend’s start-up, said that the dynamic brought out negative qualities in both of them. “She was very non-confrontational, and that’s okay in a friendship but it doesn’t work professionally,” she said. Her boss would redo projects that Samantha had done without ever telling her why. Even worse, Samantha, who also has a full-time job in banking, had agreed to work for free with the understanding that she’d be paid back “eventually” once the business was up and running. “I don’t think you would ask this of a non-friend or family member,” she said, “so it did start to feel unfair.” Samantha resigned after a year and a half without ever getting paid, though somehow she and her former boss were able to stay on friendly terms.

But plenty of other people I talked to had good experiences with friend-bosses. Kate, a freelance filmmaker, got a six-month contract to work for another filmmaker friend, who coached her to become a bolder negotiator. “He pushed me to be more confident in communication,” she said. He also trusted her with his full project budget and told her to ask for more money if she was putting in more time than they agreed on. A marketing consultant, Tory, worked for several years for a friend who launched a women’s apparel brand, and said that her boss always paid all her employees fairly. “I don’t think my friendship with Sarah affected my compensation in any way.”

When I asked Julie Zhuo, author of The Making of a Manager, how to navigate the financial component of working for friends, she said her advice would be the same even if you didn’t know your boss at all. “First, ask your boss what the criteria is ahead of time, and what they’d like to see from you to reach that level. When you feel like you’ve demonstrated that criteria, you should bring up the topic of the raise with them.” She also recommends researching the fair market rate before broaching the conversation and bringing it up if you think like you’re not making what your job is worth.

As for splitting the bill: If you’re discussing work, Zhuo says, your boss should always pay. But if you’re hanging out socially, it’s fine to split the bill or whatever you’d normally do. And if you don’t know whether it’s a work or a social hang, well, that’s a bigger problem.

“It’s important to set boundaries,” Zhuo says. “If you do go out for a social breakfast, aim to discuss nothing work related, and be aware of how it would seem if other members of your team caught wind of it. How would other teammates feel if they saw you both broadcasting the breakfast on social media?” In other words, you don’t want your friendship to put you in a compromising position, salary-wise, but it’s also important that other people don’t see you as having an unfair advantage.

Listening to Zhuo made me realize that there have been times when my friendship with Julia has affected how I do my job. There was the story I edited that Julia didn’t like; rather than push back, I killed the piece. And I’m more apt to side with Julia in a debate — honestly because I think she’s usually right, but there’s probably some friend bias in there too. These micro effects of having a friend-boss are hardly catastrophic, but they’re worth thinking about.

I also haven’t had to ask her for a raise. (It’s actually her boss who’s in charge of my salary, and while Julia could certainly advocate on my behalf, I’ve never asked her to and never would.) I know she knows what I make, but I have no idea what she makes. In fact, the only time I talked to Julia about salary was when I first got the job offer from HR, and I wanted to know how much I should try to negotiate. (Her answer: Not much, so I didn’t.) When we go out, she always insists on paying, but I swear I’m going to stop letting her do that. And we definitely need to work on setting those work/life boundaries, though as food editors, “broadcasting a social breakfast” is basically in our job descriptions. Overall, the benefits of working for Julia have far outweighed any mild awkwardness. She’s helped me become a better writer, editor, and manager, and I think of her as a mentor as much as a friend.

Zhuo confirms that my friend-boss situation sounds pretty good. “There may be deeper trust and assurance that your boss cares about you, you may better understand each other’s values, strengths and quirks,” she says. “And there’s the simple pleasure of getting to work with a person you like, which makes going to work more fun.”

But it’s good to remember that, even if our work relationship is great, my friendship with her needs to be cultivated separately. It’s been a long time since Julia and I smoked weed together in a dorm room or anywhere else, but we did find an hour for drinks on a recent work trip. We talked about our families, our relationships, and, yeah, our jobs. But, for that hour at least, I didn’t think once about her being my boss.

How Awkward Can It Get When Your Friend Becomes Your Boss?