Every one of us has to have a difficult conversation with someone at some time. How and when we have that difficult can make the difference between escalating the problem or finding a solution.

The first thing to think about is when to have that conversation. Most people want to procrastinate the conversation as long as possible. Maybe someone else will tell the person, maybe if I wait long enough I won’t need to have that conversation. The problem is that the longer that you wait to have the conversation, the harder it gets for both you and the other person. In fact, I have seen legal cases where procrastinating a difficult conversation not only made the problem worse, but also created an additional legal liability and cost the organization hundreds of thousands of dollars. The reality is you have to have the conversation as soon as possible. The longer you wait, the worse it will be for you.

Second, it is also important to understand that the conversation is going to be unpleasant. You have to get used to that fact, and learn to accept that fact. Worrying that the conversation is going to be difficult or hard isn’t going to do anything to solve the problem. It also won’t change the fact that it will still be unpleasant. As I learned from my mother, a vegetable that I didn’t want to eat for dinner, was still unpleasant in the morning when I had to have it for breakfast. Just like athletes, you have to get used to living with a little pain and being uncomfortable.

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