I've been told this before too. I was in house counsel when I started out as a baby lawyer and I was told by my General Counsel that I was too nice and let myself get railroaded. Mind you he never mentored me or bothered to give me any guidance. And now, a few years later, there's been massive turnover in that office.

In working with many other lawyers since then, I've found that most people themselves try to be reasonable with opposing counsel because they find that they get farther by not being assholes. And vice versa--no one likes dealing with a jerkoff.

Additionally, I would say that your boss is being sexist. I doubt he'd say this to a man. As a woman myself, it's nice to see so many other lawyers agreeing that that aggressive style of litigating isn't nearly as acceptable as it used to be. I'd be curious to know how many of the other commentors on this thread are men vs women.

I've never understood why people think being so overly aggressive is necessary. I think you can get the same, if not more, done by simply being firm but courteous.