Expert: Dr. Dennis W. Neder - 5/7/2009

Question
I own a small business and have a woman 12 years younger than I working
with me.  She is a single mom and has a history of bad relationships.  I am in
the midst of a divorce but have come to recognize that this woman is the one
for me (I suspect).  We've been friends for 3 years, coworkers for 1 year and
get along well (common interests, likes and such).  I respect her, admire her
and care for her deeply.  She is currently dating a guy who berates her for her
traits; the same traits that I admire most.  How do I tell her/let her know that
I would like more than to be friends.  I think there is potential here --- but I
am concerned she will compromise and give in to the schmuck boyfriend out
of fear of being alone.  She is an incredible woman and I just don't know how
much to share and how much to push.  She knows this guy is not the one for
her - but she is tired of always starting over.  I just need an opening --- it
would break my heart to see her settle for someone who is absolutely not
good enough for her.

Help -- suggestions would be greatly appreciated.

Answer
Hello Mick!

You have to decide whether you want an employee or a girlfriend. It looks like you're not going to have both. If you do what you have to do to get her (and that's a pretty big if right now) you're going to blow her right out of your company - especially if she doesn't feel the same way.

In general, you have a couple of things to do here. First you have to open her eyes about the boyfriend. You need to undermine who he is and what he's doing to her. Don't do this however by saying things like "You deserve better." She doesn't know this and if you say it, it'll just separate you and she even further. She'll think you're wrong because she doesn't see it.

Instead, tell her that the guy is a jackass and that you can't believe that she'd settle for someone like this. You can even tell her that being with a guy like him makes her look bad - even like a loser. Her self esteem has to be pretty low if she'd tolerate this abusive jackass, so you have to use that to your advantage.

Next, you have to express to her that she has other options and choices. Those are you, but don't say that yet. Eventually, when she starts to see it, you can start to make moves on her.

Remember this too: she's not going to make a pass at you. You're her boss. You have to do these things instead. You have to take the risks and realize that if she's not on the same page, you're going to lose her as an employee.

Best regards...

Dr. Dennis W. Neder
President
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