The Secret to Better Awkward Conversations: Lead With Humility

Who loves awkward conversations? 

You have something you need to say, or something you need to hear, and there’s just no getting around the fact that starting the conversation is going to be super uncomfortable. Maybe it’s defining your relationship with that certain someone special. Maybe it’s ending that relationship! It could be that you have to confront a friend about something you’ve seen in their life, or something you need to confess about yours. You might just need to clarify something, and you’re not sure how to go about it without sounding like a total doofus. Maybe it’s… 

Maybe it’s one of a thousand other things that precipitate those gulp-inducing, anxiety-producing, pray-as-you-go conversations. The point is that life is full of them, so you’d better find a way first to get used to them. You should probably also get good at them because there’s usually something riding on them—that’s what makes them awkward.

Humility to the rescue!

Here’s the deal: awkward happens. There is no way around that. You can pray about it all you want, but awkward is a fact of life. Like gravity, you can avoid it for a little while, but according to NASA, the long-term side effects of living in free fall aren’t healthy. 

In the same way, avoidance of awkward conversations isn’t a good long-term strategy (and, by the way, texting and IMing is just another form of avoidance. Nobody really wants to hear that, but that doesn’t make it less true. How you communicate matters; keep that in mind). Unfortunately, the best way to get used to awkward conversations is to suck it up and have them. That’s the bad news. 

The good news is that there is a way to have these conversations so that you can walk away feeling at peace even if you don’t get the exact outcome you wanted: lead with humility.

The key to making awkward conversations easier is buying grace. Grace lessens the pressure to be perfect. With a little grace, you can stumble around until you get it right. With a little grace, smoothness is no longer an issue. With a little grace, awkward gets easy. Well, easier anyway. And the way to buy grace is to start humble. So, here is how you lead with humility…

1. Ask for permission. Something along the lines of, “Hey, can we have an awkward conversation?” usually works well. It’s clear and to the point, but it also lets the other person have input into the conversation, buy-in. If they say yes, they know what they’re getting into.
2. Apologize and declare your intent. You’re about to say awkward things, likely personal, probably messy. There’s a good chance you’ll fumble what you want to say, possibly say something offensive. Admit all that before you do it. “I’m going to try to say this right, but there’s a good chance I’ll get it wrong. If it hurts you or offends you, I totally apologize, that isn’t what I’m trying to do. I just want to…” You get the idea. This is humility and it is endearing. You’re asking the other person to lower their defenses so you can get personal. Lower yours first and make sure they know you’re doing it!
3. Plead for grace. “Please bear with me, I want to figure this out together and I need your help to do that.” You may have noticed by now that little by little you’re baring your heart. That’s because when you’re vulnerable (which is an aspect of humility) like that, it’s hard for people to get angry or offended right away. You’re inviting them into the conversation in such a way that they’re unlikely to get upset even if the subject itself is upsetting.
4.  Make it about you. Psychologists will often tell you to make “I” statements, not “you” statements. “I have a problem and I need your help,” or, “I think you’re amazing, and…” The idea is to assume ownership of the situation, not shift blame or put undue pressure on the other person. 

Much of what makes conversations awkward is tied up in knowing what to say and how to say it. If you knew all the right words to say, awkwardness wouldn’t be awkward; it would be easy. 

What we’re after here is an easing of the anxiety of awkward—but necessary—conversations in your relationships. By leading with humility and vulnerability, you give yourself and the other person a blueprint of where to start. From there, you can lean into awkward knowing you’ve at least begun well. 

This isn’t a recipe for success—no one has that, since awkward conversations are, after all, a two-way street, only one of which you can control. But leading with humility is a great way to start off toward the best possible outcome—which is pretty cool when you consider that when it comes to awkward conversations, you might not even know what that outcome is.