From The Vault: Don't Overthink It - Just Ask ChatGPT 'How Can You Help?' With Chris Duprey

Episode Summary

From the Vault: Originally recorded in December 2023

In this episode of The ChatGPT Experiment, Cary pulls a powerful conversation from the archive with Chris Duprey, partner at The Question First Group. Chris is a leadership coach with a unique background—former Army officer, business leader, and someone who's deeply passionate about helping people grow. Together, Cary and Chris unpack how AI—especially ChatGPT—can be used in real, practical ways to save time, boost productivity, and supercharge teams.

This episode is all about cutting through the noise. Forget the cheat sheets and buzzwords—this is about how AI actually fits into day-to-day business. Chris shares his approach for helping leaders get curious, empower their teams, and run small experiments that lead to big breakthroughs.

3 Key Takeaways

• Break AI down into real life: AI doesn't have to be complicated. If you've used Google or Netflix, you're already using it. The key is making it accessible and useful for your team—not overwhelming.

• Let your team run experiments: Don't dictate AI from the top down. The real magic happens when you let people on the frontlines test it out, discover what works, and then share those wins across the company.

• Start with one simple question: Open ChatGPT and ask, "Here's what I do—how can you help?" You'll be surprised how many ways it can support your work, from summarizing notes to crafting social posts to organizing messy ideas.

About Chris Duprey

Chris Duprey is a partner at The Question First Group, where he helps leaders and teams unlock better conversations, stronger connections, and meaningful breakthroughs. A former Army officer with the 82nd Airborne Division, Chris brings a deep leadership foundation built on presence, discipline, and self-awareness. After his military service, he transitioned into business and coaching, working with and learning from mentors like Marcus Sheridan and Adam Barlow. Today, he blends his experience in leadership, mindfulness, and communication to guide others in becoming the kind of leaders who create more leaders. Chris is also a musician, a dad, and a firm believer that every person has untapped potential just waiting to be discovered.

Connect with Chris:
LinkedIn: https://www.linkedin.com/in/cduprey/
Website: https://questionfirstgroup.com

Want To Level Up With ChatGPT?

Cary offers customized one-on-one ChatGPT training in 60 minute sessions. Find out more information on the sessions, answers to frequent questions, and how to register at www.ChatGPTExperiment.com

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ChatGPT Podcast Website: www.ChatGPTExperiment.com
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LinkedIn: https://www.linkedin.com/in/caryweston

LINKEDIN NEWSLETTER
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https://www.linkedin.com/newsletters/the-chat-gpt-experiment-7110348839919702016/

MUSIC CREDITS
The instrumental music used in this podcast is called "Curious" by Podington Bear.