The Costs of Oversharing With Your Boss

Photo-Illustration: by The Cut; Photos: Getty Images

I used to work at a large corporate office with a rigid top-down structure. My boss made it clear she wasn’t interested in how we spent our free time. There was no “How was your weekend?” or “Where did you go for the holidays?” We were there to work for her, period.

I first heard the phrase “Bring your whole self to work” at my next job, a start-up where we were matched with mentors and given a budget to go out to dinner with our teams. My manager became (and still is) a good friend. Every quarter, we attended boisterous off-sites where we did bonding exercises about our Myers-Briggs types. It was way more fun than my previous workplace, and I was a lot more productive there in no small part because I felt so supported.

This all-embracing approach to mixing your personal and professional lives had a particular renaissance before the pandemic, spurred on by popular TED Talks, Harvard Business Review articles, and books about the benefits of showing your “full humanity” at work. The idea makes sense in a utopian sort of way: Create an environment where employees can express themselves, show vulnerability, and ask their bosses for what they need, and you’ll build a happier, nimbler, more innovative workforce.

The pandemic tested this notion to the extreme — many of our bosses are now beaming into our homes every day. I’ve had to cut meetings short because my infant son was screaming in the next room. My friend, let’s call her Jessica, an account manager at a homeware company who manages a seven-person sales team, told me five of her employees have standing therapy appointments blocked out on their calendars every week, a fact they probably wouldn’t have shared with her two years ago.

Even public figures have become more transparent about personal challenges that impact their jobs. Last year, sports broadcaster Erin Andrews told her bosses she was undergoing her seventh round of IVF and had to start work late on certain days. She then made the announcement public so other people might feel more emboldened to ask for similar accommodations.

“The boundaries between the personal and the professional have eroded to the point that they’re very thin if not almost meaningless,” says Ben Michaelis, a psychologist and co-founder of the Group, which offers business and leadership coaching.

For many people, normalizing this shift has been healthy. Sharing intimate information can strengthen relationships, not to mention trust, during an isolating time. “I’ve cried on Zoom with my boss twice in the past month, and while both times were embarrassing, the way she handled it made me more comfortable asking for more guidance on projects when I need it,” says Jessica. Several people I spoke to said they’ve asked for (and been granted) more flexibility in their hours to cope with COVID-related gaps in child care.

But transparency with higher-ups can backfire. A woman in her 40s I’ll call Shauna, who holds a senior position at a corporate nonprofit, was concerned when one of her direct reports asked to take a mental-health day. “I respect that everyone needs to take time for their well-being, but it seemed a little unprofessional for him to call it that,” she says. “I would have just called in sick or asked for a day off for a health issue. It made me worried that he wasn’t able to handle the pressures of the job.”

Another time, Shauna called an employee on her team to find he was shopping at Costco during the workday. “Not only was I annoyed that he was doing it, I couldn’t believe he told me,” she says. “It made me feel a little disrespected as a manager. I told him it was inappropriate.”

In other cases, opening up about yourself can result in being tokenized. I spoke to a consultant in her 30s who once found herself in a meeting with a client who expressed confusion over a queer-identity term. “I mentioned that I was actually queer myself, and all of a sudden I became the person who is asked to weigh in on anything involving queer identity,” she says. “On the one hand, I’m happy to provide that perspective. But on the other hand, it’s like, Okay, do you want to pay me extra for that emotional labor?

Personal disclosures are particularly risky when you’re not part of the company’s dominant culture, explains Manpreet Kalra, the founder of Art of Citizenry, a consulting firm that helps companies improve their social impact and equity missions. “The truth is, everyone has a certain level of unconscious bias that influences how you interact with your employees, which can create potential risks for an employee’s ability to be successful, especially if their background is different from yours,” she says. “You place your own judgments on what they can and cannot do, and what success does and does not look like.”

That doesn’t mean you have to be buttoned-up all the time. Instead, it’s a matter of treading carefully and following your boss’s lead. “What’s appropriate to tell one boss could be totally different from what you tell another,” says Kalra. For example, she once had a manager who was open about the fact that she was in couples therapy. “Then when my husband and I decided to try it, I felt comfortable telling her,” she recalls. “My boss was like, ‘That’s awesome. I’m so glad you’re doing it.’”

Later, that boss left the company and was replaced by “someone who I could not in my wildest dreams imagine being that vulnerable with,” says Kalra. However, she did feel okay asking him if she could sign up for a weekly HIIT class at noon on Wednesdays. “He was very into working out, so when I brought it up, he was like, ‘That’s great!’ And it’s funny because I would never have asked my previous boss for that. She would have been like, ‘Why aren’t you working out at 6 a.m. like I do?’”

There’s no one-size-fits-all rule for sharing personal information, but there are ways to determine whether it’s appropriate, says Michaelis. “When you’re deciding whether or not to reveal something to your boss, it helps to take a moment to ask yourself, ‘Does this make me more of a person or more of a problem?’” If it’s the latter — or if you’re not sure — then maybe hold off, he suggests.

What if you make a mistake and cross that line? “The best way to repair anything is through behavior,” says Michaelis. “If you try to explain yourself, you could end up in a quicksand situation. Whereas if you simply perform well, that can make up for saying something that didn’t land.”

Of course, there are times when your personal life does infringe on your work performance, and you need to let your boss know. Holly Howard, the founder of the business-coaching firm Ask Holly How, recommends being up front and as clear as possible. “Never leave these conversations open-ended,” she says. “For instance, if you have a sick relative and you’re operating at 40 percent capacity, try something like, ‘I want to let you know that this is happening, and it’s affecting me, but let me check in with you about it two weeks from today.’”

Then there’s the opposite scenario: Sometimes sharing personal details about yourself can advance your career because it makes people — including your boss or your underlings — like you more. And being too tight-lipped can be damaging if it makes you un-relatable. “Ideally, you want to share enough of yourself that you invite connection with other people without sharing so much that your co-workers feel like they have to take care of you in a way that they might not want to or be able to,” says Dr. Emily Anhalt, a psychologist and the co-founder and chief clinical officer of Coa, a platform that offers therapist-led “emotional fitness” classes.

Knowing the difference between under- and oversharing is “more of an art than a science,” Anhalt continues. “I describe it as too tight or too leaky. When you’re too tight, you’re not sharing any part of yourself and you appear closed off. Too leaky means you’re a puddle on the floor that everyone else has to clean up.”

Ideally, you want to be in the middle. But how to get there? Anhalt suggests the following litmus test: “If you tend to be a little bit leaky, then I recommend you ask yourself two questions before you share something personal at work. One: Is this the best person or situation in my life for this information? Would it be better suited for a conversation with my best friend or my therapist or my partner? And two: If the person I shared this with just gave me a nod and then moved on, would I feel okay? Or would I feel abandoned and hurt?” If the answer is yes to either of these questions, then stop — you can’t expect bosses to meet you in emotional places if they’re not willing or able.

If you’re on the other end of the spectrum (“too tight”), Anhalt recommends asking yourself, “If I share this, will I have offered an opportunity for this person to step a bit closer to me and to create connection?”

Ultimately, the balance is always situational — a vibe, if you will. “We all have instincts,” says Michaelis. “We’ve been living together in small groups for 20,000 years. If you’re thinking about saying something but the energy is off, that’s useful information, and you should pay attention to it.”

More From This Series

See All
The Costs of Oversharing With Your Boss