The Boss Who Takes Spa Vacations With Her Employee

Can managers really be friends with the people they manage?

Two women in white bathrobes chatting at the spa.
Photo illustration by Slate. Photos by Thinkstock.

Few people are as knee-deep in our work-related anxieties and sticky office politics as Alison Green, who has been fielding workplace questions for a decade now on her website Ask a Manager. In Direct Report, she spotlights themes from her inbox that help explain the modern workplace and how we could be navigating it better.

When you spend a lot of time with colleagues, it’s natural to develop warm relationships with them, and maybe even some genuine, outside-of-work friendships. That’s a good thing—obviously work is more pleasant when you have friends in your office. But when you’re the boss, or when your co-worker is, the rules are different: You can be friendly, but you can’t be friends.

The power dynamics in a boss-employee relationship make true friendship impossible. For starters, a manager’s job is to judge employees’ work and make decisions that affect their livelihoods, so the relationship is inherently unequal. And it’s tough to give someone critical feedback on a project or, say, warn them that their job is in jeopardy when you were gossiping over drinks together the night before. Even if you’re one of the few who can pull it off, other employees are likely to be skeptical of the relationship—and will assume favoritism, whether or not any really exists.

But it’s incredibly common for managers to overstep these boundaries—forming friendships with staff members that other people on their team feel insecure about or suspicious of or pushing for more intimacy than their employees want.

Here’s how one person who wrote into my advice column described the situation on her team:

In my department, my manager and coworker have a very intense personal relationship. They work out together during the week and on weekends, they attend all sorts of sporting events, they dine together, they take expensive vacations together (spas/vacations out of the country—one of which was financed by my manager), they text, they are in each other’s offices all day, they take selfies and post them on Facebook, and they share clothing. It is a very close friendship.

As a result, the coworker has a LOT of power in our group. She has unlimited access to our boss, and she is able to direct her own narrative. Our boss maintains that she can be objective. I disagree. There have been a number of instances where this coworker’s behavior was excused instead of addressed. She can act, essentially, with impunity.

And while being the boss’s favorite might sound like a good position to be in, it can be horribly awkward when the boss wants more of a friendship than you do:

[My boss] has repeatedly drawn me into conference rooms to confide in me about her private dilemmas, frequently breaking into tears. She seems genuinely grateful for this attention and, in return, feels like she’s returning the favor by inviting me to events she hosts for her family.

I don’t know her family. I’ve met her sons a few times. I don’t want to spend any time with this woman. I have my own family/friends I want to spend time with. I just got an invitation to her son’s wife’s baby shower. I don’t want to spend money on a gift and I don’t (and won’t) attend. How do I put a fork in this for the last time? I always refuse the invitations, citing something I need to do with my own family, knowing she won’t criticize that. But I’m tired of feeling like I have to buy her kids baby/wedding/shower gifts.

Moreover, when a manager pushes for more intimacy than an employee wants, the power imbalance makes it tough to push back and set boundaries:

Our COO is new in his role, but not new with the company. I get the feeling he does not have a lot of leadership experience, and he certainly has never led at this level before now. The issue is that he feels the need to share drama about his ex-wife, his two teenage daughters’ antics, and his current wife’s hatred of his ex-wife. This sharing goes on and on when it occurs—and it occurs during meetings occasionally, where it is totally inappropriate and wastes valuable time. Once in a while, we leave the office together at the end of the day, and I actually have stood outside waiting to walk to my car while he finishes another tale. … I know I need to say something, but I do not want to appear insensitive. How do I tell this guy to back off without making it seem like I am cold and heartless?

These dynamics can be especially hard to navigate when you’re friends with a peer and one of you gets promoted to manage the other and the relationship necessarily has to change:

After my friend got promoted to be my boss, he didn’t recognize that our relationship would need to change and that now that he was my boss, I wouldn’t want to gossip about coworkers or complain about the management above us anymore or talk to him as much as I used to about my personal life. He was the person in charge of my evaluations and raises, and I wasn’t going to share things with him that could come back to bite me, but when I tried to cool our friendship, he took it really personally and there was a lot of tension between us. It made me really worried that it would harm me professionally and I actually ended up changing jobs to get away from it.

To be clear, it’s not that managers and employees can’t have warm, supportive, friendly relationships. They can, and good managers will strive for that. But managers who ignore the distinction between friendly and friends put their staff members in a virtually impossible position and lose the credibility they need to manage effectively and be seen as impartial.

Employees whose managers aren’t setting appropriate boundaries aren’t always able to push back as forcefully as they might like to. Some people can pull off a cheerful “If you weren’t my manager, I’d love to talk about this (or hang out outside of work, etc.), but I’m old-fashioned about boundaries with the boss!” But other times, there’s not much one can do beyond being vigilant about changing the subject or leaning heavily on vague answers when things get overly personal.

That means that it largely falls to managers to navigate these relationships appropriately—and they should see setting appropriate boundaries with the people who work for them as just as much a part of the job as, say, delegating responsibilities or giving feedback. Conveniently, doing that will make the rest of their work go more smoothly, because it’s much easier to manage when you’re not sending mixed messages about whether you’re a boss or a friend. And it will free employees from the stress of trying to hint “I don’t like you that way” to the person with power over their paychecks.