Being Besties with the Boss

Last week a webinar attendee submitted the following question on the subject of critical conversations: “What’s the best way to approach your boss regarding the way they go back and forth between being your “Director” and being your “Buddy”…When they constantly go between being besties and then letting you know that the two of you are really not friends, but it’s a business relationship?”

Figuring out where to draw the line when it comes to boundaries with our teammates or our boss can be tricky, and every leader has different standards. Some are “all business,” and avoid developing any sort of relationships with their direct reports. Other leaders reside at the opposite end of the spectrum where they grant their buddies special privileges or refrain from holding their bestie to the same high standard as other teammates.

Like all leadership traits, balancing our leadership and our friendships requires both care and candor as well as the willingness and wisdom to always put the organization’s and team’s needs first.

My first question that I’d ask this attendee about their particular situation is: What are the “trends” in when they are being the boss and when they are being the bestie? Do they seem to be your buddy to get the scoop on what’s going on with the team, and then go into their titled “boss mode” when they get nervous or scared? Or do you think they’re genuinely just struggling in balancing their relationship with you as a leader and a friend?

If your leader seems to flip between buddy and boss based on their desire to get the scoop or join in on any drama, well, then they’re really not your friend (as harsh as that might sound), and it’s up to you to set those professional boundaries where you strive to serve your leader well but refrain from doing anything that contributes to gossip or drama among the team.

On the other hand, if your leader is simply struggling to figure out where those boundaries lie, perhaps you help make that process easier on them. Here are a couple suggestions:

  • Have a conversation to own your challenge. In your next one-on-one, clear the air by stating your desire to serve the team and your leader. Explain that you would never want to take advantage of your relationship with your leader or the trust that they have in you, and express your commitment to serve the team and perform well.
  • Hold yourself to the highest standards. It’s not uncommon for leaders feel conflicted when they have to hold their teammates with whom they are friends accountable. One way to eliminate this challenge is to hold yourself to the highest standards of performance and accountability. If we hold ourselves accountable, our leader doesn’t have to.

I consider many of my close teammates to be good friends, but those teammates also understand that our friendship doesn’t mean that I won’t hesitate to hold them accountable. In fact, the closer I am to a teammate, the quicker I am to critique them, and the standards I hold them to are even higher than my norm.

A few additional posts you might find helpful on this subject:

5 Relationship Breakers

9 Symptoms of Leadership Groupies


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