How to Be More Memorable in Conversations

Learn to Charm the Socks Off Anyone

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11 years ago I watched a video with Chris Hadfield that was quite literally out of this world. You may have seen it too.

He was aboard the ISS (International Space Station,) casually floating in zero gravity, which was cool enough on its own. Then, the interviewer asked him to wring out a wet towel. Yes, that’s right—a wet towel in space. Sounds like a weird reference to Hitchhiker’s Guide to the Galaxy, but the magic that unfolded (get it?) was real.

As Chris twisted the towel, the water didn’t just drip down; it formed a sparkling, floating halo around it. His enthusiasm was so contagious that I found myself laughing and leaning closer to my screen, completely captivated.

This wasn’t just science; it was a performance, an invitation to see the universe through his eyes. And just like that, a wet towel and a few globules of water became one of my favorite space stories ever.

In the years since I have seen many of his interviews. Not just because I have a deep interest in space, but because he is such a captivating speaker that I get lost in whatever it is he has to say, whether that's describing the delicate art of making a sandwich in zero gravity or recounting the silence that accompanies a spacewalk.

A personal favorite of mine is this video he did for Vanity Fair fact checking famous aerospace movies. If you’re reading this Mr. Hadfield, Top Gun: Maverick is also one of my favorite movies!

Watch him describe the “wildest thing that’s happened” to him in space:

Notice the way he uses his entire body to tell the story, his use of metaphors “It was just like I was surfing on the world’s aurora,” the way he takes deliberate pauses to make sure his audience is following.

Yes, being an astronaut and detailing a spacewalk is undeniably cool, but with his storytelling prowess, I'm convinced Chris Hadfield could make even watching paint dry sound like a suspense-filled adventure.

In fact, I had a chance to meet him earlier this year when we were both speaking at the same event together. He’s as charming in person as he is on camera.

His gift for conversation extends beyond mere information sharing. He weaves a narrative that resonates on a human level, which he does by tapping into universal themes of curiosity, resilience, and the shared bond of experiences, however out of this world they may seem.

But this ability to engage isn’t just for astronauts, poets or Barack Obama. It’s something any of us can achieve with the right approach.

As an introvert, I haven’t always had the skills needed to chat with people. But as I learned how valuable it was (I’m sorry to say fellow introverts, you do need to learn how to talk to people), I took an engineering approach and developed a three-step process for conversation that anyone can follow.

I first revealed my process in my book Humor That Works, and it can help anyone become more memorable in conversations. Here’s how you can implement it:

1. Ask compelling questions

Dale Carnegie is famous for saying that the easy way to be a good conversationalist is to encourage the other person to talk and be a good listener. He claimed you would make more friends in a week by being interested in other people than in a year of trying to be interesting.

The problem is that if you ask the same boring questions, you’ll get the same boring answers. That’s not really a conversation but a performance of things you’ve already rehearsed. Instead of the normal, boring questions, incorporate a little humor and ask questions that are different, effective, and fun.

Instead of “What do you do?” try “What’s the coolest thing you’ve worked on recently?” Instead of “Where are you from?” why not “What do you like most about where you live?” Instead of just “What’s your name?” you could follow-up with, “Is there a story behind your name?”

The goal is to get the person to talk about something they are passionate about. By asking compelling questions, you get the other person to share more about themselves in a way they don’t typically think about.

2. Tell interesting stories

When people ask you a question, it’s not about turning it back around on them. You’re having a conversation, not playing 20 Questions.

So instead of answering with a one-word response, tell a story. Studies have shown that facts are 20 times more likely to be remembered if told in story form. And don’t feel like your story has to be strictly work-related.

“Don’t just tell people your job title and stop there,” says John Garrett, former Big Four accountant turned comedian and culture change expert. “Who you are is more than what you do for work, and what you do outside of your 9 to 5 is what people will remember.”

Your story should be interesting, concise, and actually answer the person’s question.

With the right stories, you can create a deeper bond with the other person by connecting with them through your past and future.

3. Continue the conversation

How do you know what questions to ask or stories to tell when in a conversation? Simply build off the last thing the person said, using a technique from improvisation: “Yes And.”

“Yes And” is the fundamental mindset of improv… and it’s also how I went from being awkward in conversation to never running out of things to talk about (if I need to, believe, I’m still quiet most of the time).

Even a question like “How about this weather?” You can respond, “Yes . . . and if you weren’t at this event, how would you be enjoying the weather?” which turns a conversation about the state of the atmosphere into one about hobbies.

By doing this, you're not just keeping the conversation alive; you're enriching it. You transform what could be a simple exchange of pleasantries into an opportunity to connect on a more personal level.

BONUS! 4. Inject Humor

Humor breaks down barriers and creates a comfortable space for people to open up. When the topic of weather comes up, instead of a standard response, you might playfully comment, “I just learned that there are 1,800 tornados in the US every year. I heard that and was blown away…”

Okay, that might be too dumb of a joke, but adding a bit of levity not only lightens the mood but also shows your ability to share a side of your personality - an ability to see the fun side of everyday situations. And who doesn’t want to be around people like that?

Conversations are more than just exchanges of words and information; they are opportunities to connect, engage, and leave a lasting impression. This approach not only makes others feel valued and understood but also make you more likely to be remembered.

Humor entertainers have a (somewhat natural) knack for injecting humor into conversations effortlessly, but humor is a skill that can be cultivated, not just a trait you're born with.

You can develop your own unique style of humor with a bit of practice and insight. To help you get started, I've created a quiz that you can take to discover your humor persona. This will give you a clearer idea of your natural comedic style and how you can use it to make your conversations more engaging and memorable.

So go out there and channel your inner Chris Hadfield and be out of this world, if not literally, at least in conversation…

Oh, and ready to join a mission that's almost as thrilling as a spacewalk (but with significantly less zero-gravity training required)?

I'm looking for a stellar crew to help launch my latest TEDx talk into the stratosphere of public attention! Sign up to be part of my launch team and not only will you get the chance to be one of the first people that see it, but also win a prize or two in the process. It’s (probably) coming out soon!

Community shout-out

Last week I asked the readers to suggest activities I could do with my toddler.

Cathy sent over this photo and said “My 16 year old daughter and I did a 'yes and' drawing on Saturday.  I drew something and then she added to it.  We went back and forth until we had this. It was so much fun!  It is an adaptation of improv that I learned from you.”

I love it. I tried it with my 3-year old and she just kept scribbling over everything I did, but she had a blast so I’m on board with it.

What about you?

What conversation techniques have you tried that transformed your interactions or what questions do you like to ask to get to know people? Share your stories and tips in the comments below and I might showcase it in my next post.

PS. Oh, and we’ll be talking about conversation and building rapport in next week’s virtual happy hour. Join us here.