Five tips to help having an uncomfortable discussion

How to have the uncomfortable discussion

Today I witnessed not one, but two instances where people chose to have a conversation that they knew would be difficult. In both cases, the message was already contained in a written message the recipient had or was to receive. But in both instances, the person involved thought ‘the right thing to do’ was to have the conversation with the person as well, even though they knew that the conversation was likely to be difficult and possibly quite unpleasant.

Avoiding the unpleasant conversation

Over the years I have observed many conversations avoided because of the very possibility that they may not be pleasant.  But almost always, the end result is the person receiving the message via writing (or very worse case scenario not receiving the message at all), is that they say: “I wish you had told me.”

People, as a general rule, want to be able to ask questions, to test assumptions and the feedback, and they can’t do that with a static written message. Worse, they can read things into a static message that are not there, or that are not meant to be read into it.  And, the person who has sent the message has no way of knowing what messages the person receiving the message has taken from it.

Five tips for having the conversation

  • Think and plan for the conversation before hand. Take some time to think about what message you want the person to take away (one way to think about this is: if the person was to repeat the conversation to a third party, what would they say?)  Also think about possible responses, questions, reactions that the person may have. If you can plan for them, do so. Do some research if you need to, to ensure you have the answers on hand rather than saying (“I will need to get back to you about that”).
  • Think about the best time to have the conversation. In some instances, there is no way of knowing whether the time is the ‘right’ time or a ‘good time’ but you can always check in with the person when you ring or meet as to how they are feeling, whether this is a good time for them.  Be clear with yourself when you are going to have the conversation — put in your diary and do it. No procrastination; no excuses.
  • Write your first few opening lines. This may feel artificial, but it can mean the difference between bumbling your way through a difficult conversation and having a smooth opening that allows for a conversation.
  • Be prepared to acknowledge emotion coming from the recipient. Think about how they are likely to feel, and be prepared to acknowledge the validity of that emotion (even if you don’t agree with the emotion).
  • Think about what outcomes are possible from the conversation. What would represent a good outcome for you? What do you think the other person would consider a good outcome?

None of the above tips need to be time consuming or overly complicated. But taken together, they will give you a framework for having a conversation that may not make it feel much more pleasant, but will make it feel slightly easier. And it is one of those things, the more of these sorts of conversations, the easier it starts to get.

Finally, these conversations (done well) build respect and trust between the parties. Think about this for a second. If you’ve been speaking to someone during the day, and you receive an email from them that night containing a difficult or unpleasant message, one of the first things you would think is “hang on a second, why didn’t they tell me that when we were talking earlier?”

There’s another very good reason to start building a habit of having these conversations. Treat other people as you would like to be treated. So, if (as the recipient of a difficult message), you would like the chance to test that message, to ask questions, to seek additional feedback, then lead the way by doing exactly that in your interactions with others.

Do unto others as you would like them do you.

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