Your Boss Can't Be Your Bestie

Well, not without some boundaries in place.

This topic comes up regularly in my work with organizations. It’s nuanced, messy, and very tricky. If you're lucky enough to feel a strong connection with your supervisor, that’s great. But that bond can easily blur into something dysfunctional.

Here’s what "too close" can look like: 

Constant communication: Days, nights, weekends—it doesn’t matter. Work stuff, personal stuff, memes, you name it. You’re accessible 24/7. Texts slowly replace emails, and the lines start to blur.

Disproportionate fear of letting them down: If you drop the ball on a project, you're not just disappointing your supervisor. You’re letting down your friend. This creates added anxiety about both performance and preserving the relationship. 

Gossip or triangulation: If your supervisor vents to you about coworkers, that’s not just poor modeling. It puts you in a triangulated spot. Now you’re bonded over dysfunction, and that never ends well. 

About a year ago, I worked with a supervisor-supervisee duo, and I could viscerally feel the stress of the employee when she described disappointing her boss. This wasn’t just about a typical mistake. There was real anxiety about betraying her boss-slash-bestie. If her supervisor was on the outs with someone professionally, she felt she had to be too. She even feared getting the cold shoulder if she talked to someone she "wasn't supposed to." 

It’s hard to unravel where the friendship ends and the working relationship begins...especially when there was a friendship before the reporting structure. She told me she sometimes took sick days just to cope with the emotional strain.  

When I asked if they had ever talked about boundaries or their dynamic at work, she said, “Oh, no way. I could never do that, it would probably be seen as a betrayal.” When someone is in this deep, they often feel like their only options are to quit in order to make a clean break, or to betray themselves by staying quiet and maintaining the status quo. My role is to help introduce a third option: clearer, more courageous communication. Not to end the relationship- but to strengthen it. Sometimes people mistake boundaries for walls, or pushing someone away. In reality, they’re guardrails. They say, “I care about this relationship so much that I want it to work better for both of us.” What a gift. 

Insight:The responsibility to model a healthy dynamic primarily falls on the supervisor. They hold more power, and with that comes the duty to protect boundaries, not blur them. If your employee brings up a boundary, try to stay open and curious. It took real courage to speak up. 

That said, employees still have agency. Setting a boundary, even when it feels uncomfortable, can shift the tone. I once told a supervisor I wasn’t comfortable listening to gossip. It was awkward at first, but it eventually changed everything for the better. 

Takeaway:If you’re a leader, check the tone you're setting. Are you making bids for connection that could make it hard for your employee to say no? For example, inviting them to an after-work happy hour to vent about other colleagues. It might be time to rethink how you build connection. 

If you’re an employee, protect your peace. I know it can feel risky to set a boundary, but if you don’t do it early and often, it becomes harder later when a pattern is already in place. A great start to a simple communication boundary could sound like this, "Hey, I feel overwhelmed when we text about work in the evenings. I'm going to put my phone on Do Not Disturb after hours so I can disconnect. I appreciate you understanding!"  

If you're navigating this dynamic and not sure where to start, I help teams and leaders create healthy, connected, working relationships. Sometimes that means role-playing what a boundary conversation could sound like and other times it means helping you advocate for more support through HR. Either way, I’m here to help. 

Send me a message. Let’s talk.