My friend and fellow executive looked slightly sheepish as he came into my office and closed the door. As soon as I saw him, I knew what was coming.
"Diane," he said with a pained expression, "I have to ask you to talk to one of my people."
I nodded, "Okay. Who is it, and what is she wearing?"
As one of few female executives in what is still a male-dominated industry, I've been called on countless times by male colleagues to speak to female employees about appropriate work attire. I've had awkward talks with women about casual clothes, tight clothes, rumpled clothes, short skirts, too much makeup, too much cleavage, overdone hair, over-dyed hair, and much more.
Despite what some of my male counterparts seem to think, the fact that I'm a woman doesn't necessarily make it easy to talk to another women about her appearance at work. But if someone has taken the trouble to come to me on her behalf, I know it's important that she hear this feedback, so I push past the awkwardness and endeavor to deliver my message in the most positive and encouraging way I can.
These kinds of talks are hard and they don't always go well. The best experiences I've had come when I'm able to establish a level of connection and trust with the person so that they feel safe and supported rather than judged. So I always arrange to meet in person and privately, outside of work. If I don't already know the woman personally, I make an effort to get to know her and to share some of myself as well.1