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I
have been an assistant for about five months at a non-profit organization that
is governed by a board of directors. Currently, the board is involved in a
search process for a new CEO to replace one that left last year.
One month ago, I was asked to assist the chairman of the board with making phone calls and such regarding the search process. It is a very confidential matter and I have not, and would not, discuss it with anyone but the board chairman, whom I’ll call Bill. As Bill and I began working together, we started to become friends. We are both in our late 20s and just seemed to hit it off. Although I was very guarded in the beginning and never once suggested that we have any kind of relationship outside of work, he did ask me out to lunch after a few weeks and indicated it was not business. I spoke to my boss about the situation, and she recommended that I not “date” him because it may reflect poorly on both of us. I told Bill this and he accepted.
We continued to work together and develop a friendship, and now I am finding myself very attracted to him. I feel something special forming between us, but am still hesitant about whether or not to get involved. Bill has since asked me out again to a business banquet function, not a “date date.” He has also talked with the Interim CEO about the issue who does not have a problem with what I do “on my own time.”
My concern stems from the fact that the opinion of my boss and that of the Interim CEO is in conflict. I also fear that I may develop the reputation of “having gone after the board chairman.” Last, I am still concerned with the issue of dating him while we are working on a confidential project together, which is scheduled to go on for three more months minimum. My questions are: should I discuss this with my boss again? Should I go to the banquet? If I shouldn’t date him, what options do we have to continue our friendship? Lunch only?
Signed,
Dating Dilemma
Dear
D.D.:
You are already involved. Now the question is whether to continue. I assume that the Chairman of the Board is single. You are new to the organization. What if the budding relationship sours? Will your chances of doing well in the organization also sour? What if the relationship flowers? Will there be the ever present rumor that you are sleeping your way to the top? These are the questions you must ask, and apparently you already have asked since the relationship is a subject you discussed with your boss. Her advice was not to date him. So now you want me to advise you differently?
You would like me to side with the Interim CEO who does not have a problem with it according to Bill. My advice is to discretely cool it. For the time being, make all your work with Bill professional. Work with him at work. If your developing attraction grows, in time, say three months or more, you and he can then decide whether to risk extracurricular romancing. You might find of interest several Q&As in our Archives under the section on "Workplace Values--Dating."
WEGO is larger that one-on-one communication; it is the by-product of many people working together.
Bill Gorden
Workplace Doctors