The Washington Post ran an interesting article by Lois Romano last week on how Hillary Clinton is organizing her staff and leading at the State Department. For me, the kicker came at the very end in this passage:

Shamila Chaudary -- a self-described "backbencher" -- had toiled for years as a faceless expert on the Pakistan desk when one day she found herself invited to brief Clinton. Chaudary, 32, said the two sparred over whether it was prudent to engage non-governmental power centers in Pakistan, with Clinton expressing skepticism.

Chaudary held her ground, making the point that "we've been seen as not engaging with them, and it's hurt us a lot." She said that although she and Clinton "didn't necessarily agree . . . she said that it's very important for us to debate like this. . . . This is how she said she wants to do business."

Within 48 hours of their meeting, Chaudary was promoted to a front-line job in the office of policy planning.

Chaudary’s story came to mind the other day when I was talking with a client who’s getting ready to make a controversial pitch to one of the top executives of his organization. If you have enough responsibility and are doing your job well, you’ll eventually find yourself in a situation where you need to tell your boss something she disagrees with or flat out doesn’t want to hear. As Chaudary found out, hanging tough with your boss can be a career changing moment. Do it poorly too many times, though, and it can end up being a career ending moment. 

How do you do go head to head with your boss and still maintain the access and credibility you’ll need to be effective down the road? Here are some tips:

Know Your Stuff: In order to be heard and taken seriously, you have to be seen as a serious person.  That starts with having a grounded point of view on the important issues you’re advocating. It continues with having thought through the perspectives of different stakeholder groups and distilling that down to a recommendation that considers the different interests at play.

Know Yourself: It takes self-awareness to successfully go head to head with your boss. You need to understand your motivations and ensure that they’re focused on the best interests of the organization and not your own self-interests.

Know Your Boss:  Take your boss’s perspective. What kind of information would you need to know or points of view would you need to hear to be successful in your job? If you can learn to think like your boss and anticipate her needs, you’ll find a much more receptive audience. Another thing to learn is when to hold them and when to fold them. On holding them, be smart about when you go to the mat and when you don’t. If everything becomes a major issue, eventually nothing will be. On folding them, recognize that you’re not going to win every argument. Learn the signals that your boss sends when he has decided the conversation is over. Ignore those too many times and you’ll lose your access.

What else you have learned about hanging tough with the boss? What do you agree or disagree with in my tips? What tips of your own would you add?