Boss Wants to Be Your Best Friend? Ask Madeleine

Dear Madeleine,

I manage a small team at a software company. It’s go-go-go, constant crazy all the time, but that’s okay—it’s what I signed up for. I like the work and the atmosphere.

My problem may sound odd to you: my boss wants to be my friend. She is always asking me to lunch and saying things like “We have the same taste, we should totally go shopping together.”

I like her—she is a good boss, she works hard, and I respect her. I am happy being friendly with her, but it just doesn’t seem like a good idea for us to be buddy-buddy. I like all of my team members but keep things very professional with them as well. 

I asked my dad about this and he said I should play along— that it’s always good to be friends with the boss—but it just doesn’t feel right to me. What do you think?

Too Close for Comfort

Dear Too Close,

Not so odd, actually. A lot of people find the dynamics of workplace relationships confusing. And things only get more complicated when we spend more time at work than anywhere else!

I think you are right and your dad is wrong. There is clearly something that feels off for you about this situation, or you wouldn’t be giving it a second thought. If you have an intuitive sense here, I urge you not to ignore it. It is very tricky to be BFFs with the person who has control over your salary, your work assignments, and your professional destiny. I am a big fan of boundaries—keeping things friendly without crossing the line to true intimate friendship.

The question is this: how do you draw a boundary without hurting her feelings or seeming snotty? It sounds as if your boss throws out ideas but doesn’t extend any real invitations that force you to turn them down. So when she throws out ideas like shopping, you can laugh and smile and change the subject. Lunch is trickier; but as long as you pay for your own, you should be okay. If there ever was a good time to start bringing your lunch to work, this would be it. And you’ll save time and money as a bonus!

Even if something isn’t off and your boss just really likes you, it’s best to keep things cordial and professional. Maybe someday if you get promoted to her level and she no longer has any power over you, you can revisit the situation.

Finally, I applaud you for being thoughtful and considerate—and for not seeking to turn this situation to your own advantage.

Good luck,

Love, Madeleine

About the author


Madeleine Homan-Blanchard is a master certified coach, author, speaker, and cofounder of Blanchard Coaching Services. Madeleine’s Advice for the Well Intentioned Manager is a regular Saturday feature for a very select group: well intentioned managers. Leadership is hard—and the more you care, the harder it gets. Join us here each week for insight, resources, and conversation.

Got a question for Madeleine? Email Madeleine and look for your response here next week!

3 thoughts on “Boss Wants to Be Your Best Friend? Ask Madeleine

  1. It’s good to know that still there is employees attached to their moral principles and values. Our society is at saving yet. Congrats to this girl and Madeleine, for her healthy and wise advices too. In our earth we have hopes for a better world yet.

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