Wendywoman on Conversations With the Boss…

Reporter query:


What’s the most uncomfortable work conversation your boss has had with you? How did you respond, and what did you learn from it?

The cocktail party was in full swing when my boss, with whom I was immersed in a conversation,  started to lean to the right until his head was level with my waist.  Then he popped the question.  Is that  a bellybutton ring?  I was wearing a black lace top over a black camisole.  Apparently the light caught the gem on the end of the ring and it caught his attention, despite the fact that nobody else noticed.  It was an awkward moment, but now what?  I really hoped he never brought the subject up.  By this time I had a Senior Vice President title and there was a bit of a bad girl personal side to me that I didn’t share at the office and didn’t want to start now.  It had taken me too long to get to the executive suite and I didn’t want to get shot down for a bellybutton ring.    But he didn’t forget.  That incident turned out to be a lead-in to a broader discussion around the appropriateness of my dress in the workplace.  I never was going to be a navy blue suit kind of a girl, but if I wanted to advance, it was important that I took his comments to heart.    I worked with a style coach to find a look, including my hair and makeup, that would allow the authentic “me” to show up, while at the same time reflecting the smart, sophisticated look required in the executive suite. That was 12 years ago and it has worked well for me ever since.