Here’s something your boss will never tell you: Sometimes, in order to be successful in your career, you’re going to have to manage. Your boss is a human, and with all human interactions, you’ve got to figure out what makes them tick and understand them as a person. When you have to ask them to make a difficult decision, you have to understand when the right timing is.

I had a boss and every now and again I had to ask my boss for some special concessions for things that were out of the box. I wanted to have those discussions with him at the best time, but we worked in separate offices. I would call his assistant, who was also my friend, and say, “Hey, how is he doing today? I need to ask him for X, Y, and Z, and I want to make sure that I’m not catching him at a bad time.” Sometimes she would say, “you know, Chris today is not a good day to ask that. Why don’t you try him tomorrow?”

Every time I did that, it helped me because I ended up getting a lot more yeses than I would have if I approached him at the wrong time.

That is what I mean by managing up, being conscientious, and understanding the person that you’re dealing with. AND understanding when is the right time and the wrong time to have a difficult discussion with them.

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