This is part of a series of articles on Social Excellence in the workplace called “The Relationship Business Series.” Because after all, we’re all in the relationship business. For more helpful content like this, sign up for (free) The 21 Days of Social Excellence.

by Matt Mattson

I asked ChatGPT for some Socially Excellent ideas to start up more meaningful conversations at work. I said, "Be playful with your ideas."

As predicted, the robot's ideas are kind of dumb.

But maybe there’s something we can learn. Read my commentary. And read to the end for some practical takeaways.

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Me: “Hi ChatGPT. Would you please generate a list of mundane, boring, cliche workplace conversation starters along with better alternative ideas that might lead to more meaningful human connection? Be playful with your ideas! Thanks!”

Robot: Sure! Here are 10 playful alternatives to mundane workplace conversation starters:

Robot: Instead of "How about this weather?" try "What's your favorite bizarre weather phenomenon? I'm partial to spontaneous cloud formations shaped like famous celebrities."

Me: No. Don’t ask that or say that. But maybe offer a story about a weather-related memory and ask if they have any similar memories.

Robot: Instead of "Did you catch the game last night?" try "If you could create a new sport combining any two existing sports, what would it be called and how would it be played? I'm thinking underwater basketball with synchronized swimming halftime shows."

Me: OK. I guess this is fine. But maybe instead of going straight to ridiculous 7th grade camp level ridiculous icebreaker prompts, maybe try asking for a story about their favorite sports team, or what turned them into such a fan.

Robot: Instead of "What are your plans for the weekend?" try "If you could teleport anywhere in the world this weekend, where would you go? And more importantly, can I stow away in your teleportation pod?"

Me: This isn’t the worst.

Robot: Instead of "Did you see the latest episode of that popular TV show?" try "If you could be a character in any TV show, which one would you choose and why? Personally, I'm torn between becoming a dragon-riding wizard in a fantasy epic or a talking pizza delivery guy in a quirky sitcom."

Me: Dude. What? This is just the weird version of “are you more of a Miranda, Samantha, Carrie, or Charlotte?” That’s just fun stuff. Fun is good. But half dragon, half pizza guy is a little out there, AI overlord.

Robot: Instead of "How was your commute today?" try "What's the most creative way you've ever avoided rush hour traffic? I once rode a unicycle through a secret underground tunnel."

Me: The alternative question here is good. Also, “How do you make the most of your commute?" is good. But the unicycle thing is just stupid, Chatty.

Robot: Instead of "Can you believe it's only Wednesday?" try "If you could invent a new day of the week, what would it be called and what kind of shenanigans would be allowed on that day? I vote for 'Friyay Jr.' with mandatory karaoke breaks every hour."

Me: Sure. Whatever.

Robot: Instead of "Any plans for the holidays?" try "If you could have an unlimited budget for a dream vacation, where would you go and what extraordinary experiences would you have? I'm thinking a trip to the moon with zero-gravity ice cream tasting sessions."

Me: You can dial it back just a notch, robot. Goodness. People have wonderful and complicated emotions related to holidays and family gatherings. You don't have to bring in zero-gravity ice cream to find something to connect about. How about you just CARE about people's complicated relationships with holidays.

Robot: Instead of "How about them [local sports team]?" try "If you could create a mascot for our office, what would it be and what would its superpower be? I'm envisioning a fearless coffee bean with the ability to teleport caffeine directly into our mugs."

Me: Silly icebreaker questions and demonstrating genuine curiosity are, in fact, two very different things.

Robot: Instead of "Any exciting updates on your projects?" try "If you could work on any fictional project from a book, movie, or TV show, which one would you choose? I'd love to be a part of a secret spy mission led by a genius sloth."

Me: I don’t even know how to answer that question, robot! I actually thought the first one you asked here was better.

Robot: Instead of "Do you have any pets?" try "If you could have any legendary mythical creature as a pet, which one would you choose and how would you take care of it? I'm torn between a baby dragon that sneezes glitter and a phoenix that doubles as a personal alarm clock."

Me: No. Stop. Just ask about their pets. Just wonder about their relationship with their animals. Just dig deeper about how their pets bring them joy. Stop with the mythical creature stuff.

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If you made it this far through the ChatGPT Robot's goofy recommendations, congratulations!

As a real human, here are three takeaways I hope you'll implement in your workplace interactions.

1) Sincere is Better Than Silly. You don't have to be wacky to be someone who cultivates real connection.

2) Mundane Might Lead to Meaning. Don't feel pressure to "never do small talk." Small talk is fine. Just keep going with it. Go one level deeper. Ask simple follow up questions.

3) Fun Fuels Friendships. Being fun and playful is actually great. People are craving it in their lives and in their workplaces. Don't take "networking" or "building culture" too seriously while you're working. Fun fuels friendships, and friendships are the foundation of functional teams.

For now, we are more human than the machines. May we all make daily choices about our interactions so that we might stay that way.