10 Fatal Mistakes that Kill Conversations

And how to avoid them.

Jessica Wildfire
Dec 26, 2019 · 6 min read
ND 3000

Think about the people you enjoy talking to most. They make everyone feel better — a little smarter, a little calmer.

Now think about the ones you enjoy talking to least. It feels like a chore. The entire time, you just want it to end.

Afterward, you need a drink.

A good conversationalist is a good listener. They’re responsive. The best conversations have a few things in common — a mix of funny stories, factoids, anecdotes, observations, and questions. Or if they’re serious, they show sincerity and respect. That’s pretty much it.

A good conversation is simple, and it’s actually not hard with a little practice. You don’t have to light everyone’s minds up with witty banter. You don’t have to be a conversation genius.

In fact, trying to is what normally kills conversation.

Mainly, you just have to avoid irritating people. Like great conversations, the worst ones also have a handful of things in common — usually it’s someone using conversation as a means to another end.

1. Trying too hard to get something out of it

The worst thing you can do in a conversation is push an agenda. People know when you’re talking to them just to get something.

How to fix it:

Don’t ask for anything. Even if you’re talking to someone you want something from, don’t ask. Wait for them to offer.

If you have to ask, do it later.

2. Trying to bullshit everyone

Some wannabe entrepreneurs call this a skill. It’s not. The second you pretend to know more than you do, people can tell. They’re usually just too polite to call you on it. Or they just write you off.

Here’s how to fix it:

Get comfortable with asking questions, and saying, “I’m not sure.” Faking expertise loses way more respect than taking on the role of a novice. Besides, that’s how you become an expert in the first place.

3. Making it all about you

A selfish talker will use anything you say as a jumping off point into their own stories. They’ll ask the most random questions like, “Have you ever been to Egypt?” or “Have you read Infinite Jest?” Because they have, and they want to tell you all about it. They also offer way too much information, and name drop like crazy. Anyone who does this only wants a spotlight.

Here’s how to fix it:

Don’t walk into a conversation with the goal of telling your favorite stories or sharing your most precious knowledge.

Let a conversation follow its own path. Let other people talk and tell their stories. Responses will pop into your head. If you remember a story or some piece of information in the moment, that’s the thing you should share. It should come spontaneously.

4. The dreaded humble brag

Everyone feels tempted to share good news, or just promote themselves. We’re all good at something. We’ve all done exciting things. Most of us get engaged, married, or promoted.

The problem is when you get so focused on your good news, you assume nobody else has ever done anything meaningful with their lives. You assume up front they won’t be happy for you. That’s when you immediately try to downplay the big news you just shared. Trying to be humble usually comes off as arrogant and condescending.

Here’s how to fix it:

If you have good news, just spit it out. Humble bragging doesn’t work because it’s false modesty, and therefore a form of bullshit.

5. Kissing invisible ass

The person you’re sucking up to isn’t even there, but you’re talking about them in 3rd person like they’re Genghis Khan. There’s literally no point here except you’re so delusional you think this person is omnipotent, or you’re so paranoid you think they bugged the room.

Most of us have probably crossed this line at some point.

Here’s how to fix it:

If you feel compelled to praise someone, try keeping it under one sentence. Be specific, and use understatement.

6. Dancing around the point

Everything you say should have a goal, and not just a selfish one. You should be trying to inform, entertain, or persuade.

We all hate it when someone tells long stories with a bunch of random details that don’t matter, or treat random trivia and gossip like some kind of groundbreaking truth or revelation.

Here’s how to fix it:

Remember that advice for writers — show don’t tell? Well, the opposite applies to conversation.

Keep your anecdotes short. If you’re worried about offending someone, then just don’t say what’s in your head. Say anything else.

7. Ignoring all body language

At least half of conversation happens through facial expressions and other cues. Misreading or ignoring a cue could mean you trap someone who’s trying to politely excuse themselves.

Here’s how to fix it:

Learn how to pick up on subtle cues. Buy a book on body language and facial expression. If someone looks uncomfortable, give them an easy out — or excuse yourself.

8. Refusing to ever pause

This is one of easiest mistakes to make. You get carried away with yourself and then don’t let up. One idea bleeds into the next. Before you know it, the person standing in front of you has turned to stone.

Here’s how to fix it:

Actually pause. Take a breath every now and then. See point #7. If someone opens their mouth, and you’ve been talking a lot, then wrap up your story and let them interject something.

Practice asking more questions. Actually wait for an answer. Stop trying so hard to fill all the little gaps.

9. Pointing out the super obvious

We all know that one guy who can’t seem to stop talking. Instead of coming up with new topics, though, he’ll fixate on something like the temperature. He’ll even turn political debates into the simplest black and white issues — something you really can’t discuss. You find yourself saying things to them like, “Yeah the impeachment really is nuts, Bob.”

How to fix it:

If you can’t think of anything to say, then just stay quiet and listen. Trying too hard is what kills a conversation.

State the super obvious to yourself inside your head. Wait for something with a little more depth.

Get comfortable with silence.

10. Forcing advice on someone

When someone’s venting, they usually don’t want advice. There’s a good chance they’ve already tried what you’re about to suggest anyway. It’s even worse when someone pretends to know every detail about your situation, or trivializes it by saying something like “All you have to do is…”

How to fix it:

Just listen and prompt them for details. If you have a suggestion, then preface it by saying, “Have you tried X?”

Wait for them to actually ask for advice, or say something like “I just don’t know what to do.”

If you really want to help someone having a rough time, then offer to talk to them more about it later. Be modest. Say something like, “I’ve been through something similar, and I’d be happy to tell you what worked for me.” That last part is crucial — it’s what worked for you.

Conversation isn’t that hard

All you have to do for a good conversation is show up and let go. Ask simple questions. Weekend plans. Hobbies. Books or articles they’ve read. Places they’ve been. Old jobs.

What’s their favorite drink?

It’s not the first question you ask, it’s the follow ups — the five Ws (who, what, when, where, why). Get the other person to expand and elaborate. Why is it their favorite drink? When they did first try it? Then you tell them your favorite drink. Before you know it, you’ve learned a lot about someone in just an hour — more than you thought possible.

The problem is that we walk into conversations with grand plans and expectations. We want to promote ourselves and look smart. A conversation isn’t a dance off. It’s a waltz. Some conversations are better than others. Sometimes they just die. But if you avoid these 10 flaws, at least you won’t be the one who killed it.

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