How to Have a Crappy Conversation

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

  1. First, pat yourself on the back. Many people talk themselves right out of crappy conversations, but you’re not. You’ve got guts.
  2. 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.
  3. 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.
  4. 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.
  5. 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.
  6. 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.
  7. 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.

Now go do good…and do it well.

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

10 thoughts on “How to Have a Crappy Conversation

  1. Mark says:

    Crappy conversations are like pruning a plant to enable it to grow. A righteous firing is good for both sides. Enlightened self interest dictates match your guide, I think. The person not performing at home at some level knows they aren’t getting it done. In other ways, calling in over-scented employee enables future conversations that person has with customers in ways they will likely be grateful to have…whether they know it or not. And a bad client fit is bad for client and supplier and enables both to move on productively. In the end, crappy is better than undone.

    1. SO true, Mark. I have actually been on the other side of crappy conversations and HATED hearing the feedback at the moment, yet I know for a fact that it made me better in the long run. Crappy beats undone every time.

  2. Tina says:

    Great title and advise. Funny thing is that right before I saw and read this I had to have my own crappy conversation. I didn’t fret over it because it was a situation that came up with an employee that needed handled immediately. Unfortunately I seem to have this conversation with him every year at the beginning of tax season. But I was nice (to start), then firm when needed and end result is he is doing what everybody else is doing, following the process that was set out to make things work more smoothly. He may not be happy immediately, but I am, and he will come around, like he always does.

    1. Sounds like you could’ve written this one, Tina! The other good thing is that it probably wasn’t a surprise for him that this was coming. Once you have a crappy conversation, it puts the other person on notice that more could be on the way…frustrating for us, but still valuable.

  3. Patty says:

    Thank you Deirdre. Such well-needed tips on unpleasant conversations. I think being kind and thoughtful and making “I” statements are really good ideas. No sense adding fuel to the fire.

    1. And it’s so easy to add that fuel, Patty! Thanks for your great comments!

  4. Dave Oates says:

    Crappy Conversations is the name of my new band!! Great write up!!

    1. Ha! Love it! You MUST allow me to play in it!

  5. Sandy Mayberry says:

    Well done. Now I need to modify your suggestions for the reality conversations with most of my clients. Kind, firm and thoughtful helps, but sometime we’ll have to talk about helping them move forward even after hearing the bad news related to their divorce. Then, how to handle when they take their anger and frustrations out on their lawyer. 🙂

    1. Ha…great point! Sometimes you have to deliver the crappy news, and then deal with their response in a whole different way. Thanks for the great comment!

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