How to have awkward conversations you don’t want to have

It’s those convos that you really don’t want to have. You know you have to have them but at the same time it’s not the end of the world if you don’t. So what usually ends up happening? You delay, delay, delay until shit hits the fan.

The types of awkward conversations I’m talking about are:

  • I hear that you’ve been applying for other jobs
  • We can’t meet your unrealistic expectations and no longer want you as a client
  • So are we more than just friends?

Having to have all these awkward conversations in the last week or so, I thought I’m surely not the only one that struggles with them. After years of avoiding awkward conversations, I now know how costly it is not to have them earlier on.

Here are some steps that will help you get these hard conversations outta the way to save time, money and heartache.

1. It is what it is. Awks. 
“Jessica, we need to have an awkward conversation”.
Stating the obvious seems counter-intuitive but if it’s going to be awkward and you’re frank about it — it’s actually genius to get it out on the table, straight off the bat. Firstly, find a time and a place where you can both speak privately. Opening up with this line will bring a touch of levity whilst keeping the serious tone you need so they know you’re going to have an honest conversation with them (and possibly not hold back).

2. Skip the nice stuff.

Well, you’ve started off by saying it’s gonna be awkward, so get straight to the point. Let’s not delay it, we can get on to the nice stuff later.

3. Be awkward and honest together.

So it’s out in the open, you can both bask in the awkwardness together. By having this feeling in common, you can now have an honest chat. Ask them if there is anything they would like to share, add or clarify to what you’ve just said. This shows you’re willing to listen and both arrive at an outcome together (or not, and that’s ok).

4. Now the nice stuff.

After all the hard things are said, this is the perfect time to give compliments, encouragement or show your appreciation. Best to say something specific to show you are genuine and that you really mean it.

5. Walk away not so awks please.

Starting an awkward convo does not mean you need to end it that way. Finish the conversation with something that isn’t so awkward. If you need to take some time to think further, tell them. If you need to apologise, then do it. If you need to have conversation with other people before getting back to them, let them know what you need to do. Now walk away with a sense of purpose and not doing the side crab walk thing where you want to disappear into a sand hole.

It certainly makes it easier if you enter these conversations with a clear purpose and willingness to listen to the other person. These awkward conversations need to serve a purpose and ultimately lead you to find clarity, resolution or action.

Stay Peachy,

Sheryl Thai, CEO

League of Extraordinary Women

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