Best way to conquer difficult conversations: just do it!

There are numerous books and courses that will teach you the best way to approach those difficult conversations whether it’s:

  • firing an employee,
  • asking for a raise,
  • asking for money that someone owes you,
  • telling a loved one that their behavior is hurting you,
  • and so on.

First off, if you are avoiding a conversation, consider how important it is. If Bob picking his teeth at lunch bothers you but you only have lunch once a month, then maybe you better work on your tolerance instead. If Shelly leaves her co-worker’s office crying every month, then maybe it’s worth getting up the nerve to talk to your co-worker. (And Shelly.)

The single best thing for getting better at those conversations is to have those conversations. The first few might not go so well. Don’t worry. Be sorry, apologize, take notes, learn. The next time you are avoiding a conversation, think about the past experiences, rehearse it in your head, practice with a friend, and then JUST DO IT. Avoiding a difficult conversation will not make the problem go away and the more practice get with them, the better you’ll get at them. (They never get easy. When they get easy, you’ve stopped caring. It’s time to get some help yourself.)

Oh, and have these conversation in person. If you are feeling chicken, and depending on the nature of the problem, you might resort to the phone (I’ve done that – especially when people owe me money) but never resort to email. Only use email as a follow-up to remind the person what’s been agreed to and to create a "paper trail" that you can refer to. Difficult conversations go much better in person where you can read body language. It’s not such a bad thing if the other person can see how hard it is for you too.

And always remember, it’s not easy for the other person either.

Now, if you have any advice on how to engage people that are avoiding you, I’ll take that.