
Dear Madeleine,
I recently joined the accounting group for a company that runs family offices. I like the work and am learning a lot after simply working as an accountant for many years.
My boss is very invested in my success, which is great. My problem is that she seems to want to be friends. I moved to a new city for the job, but I had a lot of connections from school and have found a solid friend group. Even if I hadn’t, it just doesn’t seem like a great idea to spend a lot of social time with one’s boss.
She has asked me to go for a drink after work, get together to go to the farmers’ market on weekends, go to the movies. For a while I could claim unpacking and getting settled as justification, but I am running out of excuses.
She is about 25 years older than me and seems lonely. I don’t want to turn her against me, but I am worried if I keep declining invitations, I will. What do you suggest?
Out of Excuses
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Dear Out of Excuses,
Hmmm. I understand your concerns and I think your instincts are good. The last thing you want to do is offend your boss. Here’s the thing, though: you don’t really know what her motives are. It is possible she is lonely and hoping you might fill gaps in her social calendar. But what if she genuinely wants to get to know you?
What if you accepted one invitation, just to get a sense of what is going on? I suspect she may stop inviting you once you have done a social thing together. Of course I could be wrong, and if you accept once, the floodgates will open. But if you enjoy her company, what’s wrong with spending a little bit of social time with your boss? You don’t have to spill your deepest, darkest secrets; just enjoy one another’s company and get to know each other a bit.
If the invitations start coming fast and furious, tell her the truth—you prefer to keep social time with someone who is your boss to a minimum; you enjoy her company but feel it is better if the relationship stays friendly and professional; and you believe a little distance is wise because it keeps things simple.
Yes, she may disagree—or even retaliate. So I would suggest keeping a detailed and accurate record of her invitations to show HR, should you ever need it. I appreciate that you don’t want to naively walk into something that could become emotionally fraught and complicated. But you also don’t want to overthink this.
I guess I tend to err on the side of giving people the benefit of the doubt and assuming best of intentions, and it has served me well. Of course, it also makes life a little more interesting. Maybe find out a little bit more before you draw boundaries?
I am trying to pinpoint a principle to explain my view. I guess my role model is Ken Blanchard, who has never failed to invite everyone in his vicinity to join him to do anything. And he has more friends than anyone I have ever met. Can one have too many friends in life? I don’t think so.
Trust but verify. Have some fun but stay sober and keep detailed notes. And stay curious. You never know when life will present you with something delightful.
Love, Madeleine
About Madeleine

Madeleine Homan Blanchard is a master certified coach, author, speaker, and cofounder of Blanchard Coaching Services as well as a key facilitator of Blanchard’s Leadership Coach Certification course. 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.
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