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.

Third there are different styles of dealing with difficult conversations.  But regardless of style, you must have compassion in having the difficult conversation.  You cannot be oblivious to other people’s feelings.

As far as styles of having a difficult conversation there is a difference of opinion.  Some people like to build up to the conversation and leading with information completely irrelevant.  In some sense they are building rapport with the other person and trying to put that person at ease.  Studies have shown that the first four minutes of a conversation has the highest levels of “turbulence” or difficulty and anxiety.  Allowing the turbulence to go by allows the conversation to flow better.

Other people like to take the band aid off quickly.  In other words, they lead off with the bad news. Then they talk about solutions to that bad news.

It is also important that after you have given feedback that is critical or difficult, you need to solicit feedback from the person you are speaking to.  You have to ask them to comment on the issue.  This is not a monologue.  It is a dialogue.

Finally, there are people that like to sandwich the conversation:  Good news, bad news, and then good news.  In other words, the bad news or meat of the conversation is surrounded by good news which is the bread.  By doing so, you can start and end on a good note.  Usually, people will compliment a skill, criticize, and then finish with a compliment.

The reality is that difficult conversations will be just that: difficult.  But if you manage the situation, you can help to make an unmanageable situation less difficult.