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How to Have an Awkward Conversation: 5 Steps

You know that feeling you get when you need to talk to someone about that uncomfortable topic and it’s just time to finally address it? Yeah, I hate that feeling too.

When you know it’s time to have that conversation, you should have an idea of where you want the conversation to go. Don’t start the conversation without an end in mind. It’s like the difference between cutting someone for the purpose of surgery versus cutting someone and walking away leaving them to bleed and fend for themselves. Don’t do that. If it’s going to hurt at least know you’re doing it for a good reason and be prepared to stitch them up at the end.

Here’s an outline of how you might enter into your next awkward conversation:

1. State the Obvious

I like to take a straight forward approach to starting the conversation. If I need to have a difficult conversation with Joe I would find a time and place where we can talk privately and I would literally start the conversation like this: “Joe, we need to have an awkward conversation.” I’ve found that leading with that brings a touch of levity to the whole situation but also makes it clear that it’s about to get serious and you’re not going to hold back.

2. Don’t Give Compliments

When someone knows you have something serious to say they’re ready for you to get to the point. Any compliment you say in an effort to delay the real reason for the conversation is going to be ignored because they’re waiting for the hammer to fall. Just skip the compliments. Those can come later in the conversation. You said it was going to get awkward so go ahead and get awkward as fast as you can.

3. Assume There May Be Facts You Don’t Have

The nice thing about the awkward conversation is that you will feel awkward too. You’re in the same boat as the person you’re talking to. After you say what you need to say ask them if there’s a side of the story you’re missing. It’s possible there’s more going on than you know. Giving them a chance to clarify or inform the conversation shows that you’re willing to listen and haven’t already shut the door on the opportunity for them to redeem themselves.

4. Now Give Compliments

By now you’ve said all the hard things you needed to say and the other person may have as well. This is a great time to compliment the person. You might compliment them for their attitude or candidness or overall contribution to your organization. Find something to say and be as specific as you can so they know you really mean it.

5. Don’t End Awkwardly

While you start the conversation with awkwardness you don’t want it to end that way. Throughout the conversation you will be stuck in the middle of what you’d like to happen and listening to them for additional, potentially contrary, information. You may need to adjust your expectations or desired outcome on the fly, but whatever the case conclude the conversation with something that isn’t awkward. Depending on how the conversation goes you may have additional conversations that need to take place with other people. If so, make it clear to the person you’re meeting with to state that you need to do that. Do you need to think further about the situation in light of this conversation? If so, tell them. Do you need to apologize? Do it. Find a landing spot and try to land as smoothly as possible.

The awkward conversation should ultimately serve a purpose and if you can enter into it with clear purpose and a willingness to hear the other pe