How To Deal With Awkward Interviews & Conversations

Awkward ConversationI’ve been told that I’m not the best conversationalist. Even my current wife said that early on in our relationship there were times that she felt a little awkward.

Over the years I think I’ve gotten better. I know I’m still not the best. Especially on the phone.

But I’ve been aware of things and have sought out ways to be better.

So let’s say you’re experiencing awkward interviews or conversations. Here are some of the things I’ve learned that can help.

1. Listen More

Do you listen to some podcasts?

They have exploded in popularity. I love them.

One thing I’ve noticed is that there are some really good interviewers and some really poor ones.

The key differentiator?


The best interviewers are the ones that listen the most. The worst ones interrupt and talk. They want the focus to be on themselves.

It’s the same in real life. The people that are most awkward in conversations are the ones that do too much talking. They just wait for their “turn” to talk. Sometimes they don’t even wait. They definitely don’t listen.

A good general rule of thumb is to listen more in interview settings and in conversations. When asked a question give your answer, but don’t go on too long.

Obviously you don’t want to be a mute, but in most cases you’re probably talking too much.

2. Ask More Questions

Let’s say the awkwardness comes from too much quiet. Instead of jumping in with rambling, start by asking questions.

You’ll find that people like talking about themselves. Even in an interview setting you’ll find that the interviewer will like talking about their business. They’ll like talking about their story in the business. They’ll tell you so much information about the job, the business, etc. if you just ask a few questions.

Ask them to describe things. Ask them to tell stories and provide examples. Things that make for detailed answers vs. things that more yes/no.

3. Dig Into Their Excitement, Interests

Building on the last one is the idea of digging into what the person is interested in. One thing is themselves, but it’s deeper than that.

Their work. Their hobbies. Their family. Their friends. Their history and experiences. What they’re looking forward to in the near future and in the long-term future.

One reason for awkward conversation is the lack of things to connect on. Or a lack of interest in what the other person is interested in.

To be interesting, be interested in what the other person wants to talk about. Even if you don’t know what they’re talking about take on a curiosity mindset. People like teaching. They like being experts.

You don’t know anything about lacrosse? Fine, ask them to fill you in on the details. When did they start? Why do they love it? How often do they play? How many players do you need? Where do you play?

Dive into what the other person is interested in and the conversation will flow and they’ll love it.

4. Practice Storytelling

Now, there are times when you have to do some talking. You can’t be a mute like we said earlier.

A great way to be more interesting is to focus on storytelling. To practice it.

Some people are really good. They know how to build to a climax in a story. Keeping listeners on the edge of their seats waiting for that climax to hit.

Other people fumble with their storytelling. They forget details. They go back and forth and jump across the story arc. They use phrases like You had to be there or You know what I mean.

No, I don’t know what you mean. That’s your job as the storyteller to make me understand.

Storytelling improves with practice. Practice storytelling with your spouse or kids. Practice in the mirror. Practice with friends.

The key is to watch for their reactions. What makes them ask a question? What makes them maintain eye contact? And what makes them reach for their phone? What makes them glance toward the door?

You’ll learn when you lose them and the types of stories and ways of telling them that keep attention.

5. When Rambling: Stop

It’s a natural reaction to want to keep talking to “fix” the situation, but you’re just making it worse.

When I listen to storytelling a big issue is rambling. The person will lose their place and fumble around. Then they’ll fumble around more and make the situation really awkward.

If this happens it’s totally okay. Just stop. Say, “You know what, this story isn’t really that interesting let’s talk about something else.”

The person will love that.

People can be forgiving. Especially if you stop an awkward situation and look for another way to restart the conversation. Ask them a question. Find another interest of theirs to talk about.

6. Create A List Of Topics To Avoid

The big ones are politics and religion. And if you’re with the wrong crowd you probably won’t want to discuss your work. Maybe not even your kids or your pets.

It partly depends on the company you’re with.

Look for your hot button items. The things that bring out the biggest emotions in yourself.

When these topics come up let the red flag go up. Swallow your pride and go against your inclination and look for a way out.

Change the conversation. If they keep coming back to it just say that you’re not really that interested in those topics.

The topics on this list work best with the people you know the best. Family and friends. Ones that won’t judge you based on one conversation.

7. Act

Finally, you can pretend you’re an actor. Think about how a great conversationalist would go about this situation. Pretend you’re an actor from a TV show that is great with people. Take on their persona and let your instincts takeover.

It works.

It’s weird, but it works.

I think sometimes we get these ideas in our heads that we’re bad conversationalists. And it kind of becomes a self fulfilling prophecy. We believe we’re bad at it and then we’re bad at it.

One way around this type of thinking is to pretend to be someone else. The more you do that the more you’ll switch your thinking. Even if you’re acting you’re still the one succeeding in conversation.

Try it and see what happens. It’s worked for me in more than a few situations. To me, it’s not being fake. It’s learning more about my own capabilities.


Nobody likes awkward conversations or interviews. But they do happen. I think it all starts with self awareness. Knowing that you’re having some struggle in this area. If you’re reading this post then you’ve passed that first step.

Now try some of the tips above. They’ve worked one former awkward conversationalist improve. Me.

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