I find that as I move up the career ladder, my biggest challenge is that I don’t know when to negotiate, and I have no one to ask re: when this is ok or not ok. Most of the senior leaders in my industry are men, so I’ve personally failed to build a network of mentors in the same way my male colleagues have. I try to negotiate when I start a job because I know the value I will add to a business. However, I believe men ask for raises much more frequently than women do. I don’t feel comfortable asking for a raise out of the blue, especially without a very significant accomplishment that I largely or entirely contributed to. Come to think of it, I don’t think I’ve ever asked for a raise at work. I’ve been given raises by good bosses who value the work I bring to the table — but perhaps those raises would have been larger if I had been more assertive, or been more frequent. I personally find that the more senior I get in an organization, the more uncomfortable I am negotiating for a higher salary. I’d prefer to be fairly rewarded for my contributions when the time is right, but I’m not sure a man (slash most men) would feel the same way.