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Dear Captain,

About two years ago, I was hired to work at an awesome but small non-profit. I spent my first year in a low-end administrative position that quickly became mundane. However, after taking on additional projects and consistently showing my skill and desire for more intensive work, I received a huge promotion to a development position. I now answer directly to the CEO, and things are going pretty well. I just brought a new donor on board, and everyone is singing my praises.

However, a huge mess of awkwardness has arisen.

The woman who held the position before me had years of experience in writing and development. She had a VERY good salary (from what I hear) and was close friends with the CEO. However, her performance was less than stellar. In an entire year in the position, she never brought a donor on board and failed to document most of her contacts. Because of this, the organization asked her to resign early last year. Since I took over eight months ago, I have been trying to fill in the informational gaps. In some cases, I’ve had to start from scratch.

Now, this woman had a list of potentials she was trying to develop, and my CEO (still hung up on how “experienced” she was, IMO) wants me to pursue them. However, I do not know (because of the utter lack of documentation) what the other woman’s relationship to these entities were, and some of them appear to be real long-shots. So now the CEO is asking me to CALL THE TERMINATED EMPLOYEE and ask! I’m so uncomfortable with this request, you have no idea. When she worked here, I was just a low-level associate. Now I’m supposed to tell her that not only have I taken over her old job, I want access to her contacts, too?! It seems insulting. I’m thinking about telling my boss that I just can’t do it. It’s not just an affront to her pride, but also to mine. What do you suggest?

Sincerely,

Too Appalled to Call

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Hi Captain Awkward,

A few months ago, I met a guy who works in my field through a professional networking event. Since then, I have noticed that he has such a brutal case of White Knight Syndrome that he will actually create Drama just to “save” the women who happen to be in his presence, including myself.

I only see him at business events (barely once a month), but it’s becoming more and more of a problem for me since 1) it is a small scene professionally, 2) he believes our passing acquaintance means we are BFF and thus FEELINGSDUMP and DRAMA in public from him every time I see him, 3) I’m just starting off in this field, and 4) because of 2), other networking attendees believe he and I are friends, thus making any attempts at networking that much harder for me. (Did I add that I am an introvert?) They see his unprofessional conduct, believe we are friends, and believe I am just like him. I don’t want him in my life at all! When I met him I was polite, but I didn’t know he would repeatedly try to violate my boundaries and neither do most of the organizers of these events. These events are also happening in public spaces such as bars and restaurants.

Any tips on what I could do next time he shows up?

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