How using Cranky Conclusions makes tough conversations easier

Ever needed to tell a teammate something tough but fear they’ll get too defensive? Here’s one way that’s proven to work.

You’re going to say the technique I’m about to share is just a glorified way of manipulating someone. Hear me out though.

Not all conflict is easy to address. We’re by no means perfect. We put so much of ourselves into our work that it’s hard to not take some feedback personally. Telling someone they’re under-performing or having a negative impact on a team can put them on the defensive quicker than you blink an eye.

How are we supposed to talk to someone about the sticky things? Sure, we could just dive right into it and risk them getting defensive. Or we could be a little more pragmatic.

Introducing Cranky Conclusions #

Let me introduce you to my favorite preparation tool for hard conversations. It starts with a simple question:

What’s the worst thing they can say about me? #

This is helpful for two reasons: it primes your brain for empathy and prevents you from being caught off guard when you go talk to the other person.

How’s it prime your brain? By visualizing the worst places they can go, you’re putting yourself in their shoes. You’re also exploring what they might think when they hear this news.

Cranky Conclusions help you be better prepared for a conversation that could get weird. It works because you’ve you anticipate the negative places they might go even before you breathe a word of it them . They give you the chance to tailor your conversation and route around those bad thoughts . If you use them in a conversation, you’re going to short-circuit them thinking the worst case scenario.

Putting it into practice: the smelly teammate #

For example, let’s say you’re working with someone who smells like the inside of a moldy, smoke-filled motel that’s recently been unsealed after years of being shut off from any kind of fresh air. You appreciate them as a person and respect their work but the smell is oppressive and makes concentrating or staying next to them for more than a few moments difficult. If this example sounds really specific, it’s because it actually happened to me. I still remember the smell to this day.

If I do go and talk to them, I use Cranky Conclusions find the worst thing they can say. Here are a couple things that come to mind:

  • I’m an asshole, they smell just fine
  • I shouldn’t try to tell them what to do

Armed with those thoughts, I can now go talk to them. Hopefully, I can prevent them from thinking the worst so they can actually hear what I have to say. I usually say something like this:

You’re going to think [the really bad thing]. Hear me out though. #

Note that this statement doesn’t include “but.” Cranky Conclusions are just like apologies: if you include a “but,” you negate everything that comes before it.

Back to the smelly teammate: once I made my Cranky Conclusions, I went up to them one-on-one to talk. I said “hey, I’m gonna sound like an asshole who’s trying to control you when I say this. Please hear me out: I’m very sensitive to the smell of smoke. When someone smells of it, it makes concentrating really tough. Is there any way that before we work together that you can do something about it?”

Luckily, they were cool about it and offered to use some mouthwash before working together. Problem solved, but that was hard to broach for me because I know how touchy people can get when it comes to hygiene.

Once you’ve used a Cranky Conclusion in your conversation, you’ve likely short-circuited their brain from thinking its worst thoughts. Now you can have a more productive conversation.

I’ve used this technique with my direct reports, my teammates, stakeholders, (and even family members). It’s been very successful in helping me talk about hard topics.

Going even deeper #

You can go even deeper with Cranky Conclusions by asking how you might’ve contributed to the situation.

It gets a little harder from here. Looking at your role requires a mountain of honesty and willingness to be wrong. It’s like that because this exercise often highlights how selective your perceptions of a situation are. While we want to believe we’re being fair, we often aren’t; it’s because we forget to look at how we might’ve contributed.

Claire Lew (CEO of KnowYourTeam) has a great perspective here:

It’s perfect that she asks you to think about what might be common sense to you but not to them. I have been lucky to have a few managers who operated that way. They were the most effective ones I ever had, by a long shot. While this applies well to the manager/direct report relationship, it’s also incredibly effective for teammates.

What if I I don’t have any responsibility here? #

You won’t always find that you have any responsibility for the situation being what it is.

This is especially true if you’re on the receiving end of harassment or abuse. I’d like to think that’s obvious but there are always one or two dudebros reading along that still don’t get it (hi, dudebros!), so I’m going to say it again: victims bear no responsibility for someone else’s actions. If you disagree, [Joshua points behind you] there’s the door.

Overall #

Cranky Conclusions are really helpful because at its core it’s a tool to build empathy. After all, you’re putting yourself in their shoes and asking yourself what they might say in response to some hard news. Cranky Conclusions also make it harder to get surprised in a conversation. You can even use it to start a conversation with one (for an example, go back and read the first line of this article).

If you want to go deeper, you can ask yourself how you might’ve contributed. It’s a great way to help you be fair in your perceptions because we’re often selective about our facts and the roles we play.

Try this before your next conversation #

  • Ask yourself “what’s the worst thing they can say about me?”
  • If you think it’s going to be a hard conversation, use something from your Cranky Conclusions to start the conversation
  • Take a moment and look at how you might’ve played a role in things being like they are

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