How to Have a Crappy Conversation

How to Have a Crappy Conversation
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This week brought an interesting theme. Two of my colleagues – and me - all found ourselves in a universally dreaded situation.

We had to have crappy conversations. And they Stressed. Us. Out. (Nooooo sleeping here.)

  • Colleague #1? He had to tell his somewhat-non-performing staff member who really loved working from home…that he would no longer be permitted to work from home.
  • Colleague #2? She had to tell her co-worker that, due to multiple customer complaints, she needed to tone down her very-strong-and-somewhat-mushroomy-smelling perfume.
  • And me? I had to end a relationship with a client who was no longer the right fit.

Crappy conversations can involve our professional lives (like disciplining an employee, leaving a job, or advocating for ourselves in some way) or our personal ones (like ending/addressing a relationship issue, stepping away from a group, or…advocating for ourselves in some way).

For many of us, that moment when we realize a face-to-face crappy conversation is in our future, our stomach seizes up a bit. We put these talks off, yet continue to obsess about the words we’ll use…which all feel wrong.

Why do so many of us hate crappy conversations?

Because we’re nice people, and we don’t want to hurt someone’s feelings or put them in an awkward position.

Also, crappy conversations are uncertain. While we can choose our own words, there is no telling how the other person will respond. There could be crying. There could be yelling. There could be worse (which we’ve imagined while lying awake at night, thinking about all of the possible scenarios).

Yet these crappy conversations must be had. After all, something has told you that it is time to confront someone, and it’s about something important…which is why it’s stressing you out.

So…what to do when the time comes? Just how to have that crappy conversation?

A few steps to help guide the way…

Deirdre’s Guide to Crappy Conversations

  • First, pat yourself on the back. Many people talk themselves right out of crappy conversations, but you’re not. You’ve got guts.
  • Since you can only control what you say (and not how they react) choose your words carefully. Be thoughtful, be kind if you can, but also be firm. Crappy conversations aren’t usually about two-way debate as much as addressing an issue, setting a boundary, or communicating a decision. Plan for “I” statements (“I’ve decided this” or “I need you to address this” works way better than “You aren’t doing this correctly” or “You let me down”). If it's appropriate, start by naming that this is a hard conversation to set the tone. Also, plan for bullet points. A script sounds like a rehearsed scene...not a conversation.
  • Cut to the chase. Crappy conversations can and should often be the quickest talks you have. If you ramble out a long list of reasons or have a huge-build up, you’re true reasoning will get lost. Plus, chances are you’ll lose the other person after 30 seconds anyway as they’ll already be in their own heads, planning their response or rebuttal.
  • Do them ASAP. Don’t obsess for weeks. It’ll drive you crazy. And on the big day, do it early. You’re awesome for doing this, so get it over with.
  • Make it impossible to chicken out. Let the other person know ahead of time that you want to talk to them at a certain time. Don’t make it a big deal, necessarily, because you don’t want them freaking out. And don’t give up the goods ahead of time. Do it on your terms, in your timing.
  • Give them room to respond, but not debate. Avoid defending or justifying yourself over and over. There’s no reason to if you were clear from the start.
  • Pat yourself on the back. When it’s done, no matter how it goes down, give yourself some credit already. You did what others won’t, so feel good if you can.

That’s what we all tried to do this week.

So how did those crappy conversations go? An update:

  • Colleague #1’s went okay. He was thoughtful, kind and firm in his delivery, and – most importantly – his staff member isn’t working from home anymore.
  • Colleague #2’s went okay, though not quite as well. She was thoughtful, kind and firm in her delivery and, while the woman didn’t react quite as positively – most importantly – she won’t be using that perfume anymore.
  • And me? It went okay, too. I was thoughtful, kind and firm. And, while it appears this professional relationship is fairly damaged, I still know I did the right thing.

Whatever the case, we all felt good, if not a bit crappy, when it was over.

And we all slept a whole lot better.

PS: Thanks to Andy G for the awesome pic of our very-awake baby!

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