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B
Hey. For this week's show, I'm bringing an interview out of the vault. This originally aired December of 2023 and I'm struck by how relevant and salient the points are now, just as much so as they Then the conversation you're going to hear is going to help you break down AI into real life. It doesn't have to be all that complicated. We're going to hear about the benefits of experimenting and sharing those experiments as we test our curiosity. And the one question to start with to get the Most out of ChatGPT for your personal or professional use. If that sounds interesting to you, then stick with me and I'll join you on the other side of the music.
C
Hey gang.
B
Welcome to the ChatGPT experiment. This is the podcast designed to help you better understand what ChatGPT is and get a nugget that you can use for your personal or professional needs. My name is Kerry Weston. I'm your host. Holiday break going on now. So I'm bringing out some episodes from the Vault and this is a good one. And if you've been with me for a while, you know that I have both solo episodes and people on to join me for interviews. And this one that I'm sharing with you now is the very first time that I had an interview on the show. And I think one of the things I want to share was just how nervous I was. I had no idea what I was doing. I'd never talked to anybody on air and recorded it. And I was basically just kind of finding my way down a dark hallway. And thankfully Chris Dupre, who joined me, was a pro and could take any question I was giving him and give me some remarkable nuggets. And this turned out to be one of the episodes that I got a tremendous amount of feedback on because of Chris's direct and simple approach. He breaks things down so that you can understand it from the easiest angle. There's a lot of good nuggets here that I mentioned, the intro. They're just as relevant now as they were two years ago. And as I continue to talk to people, individuals, teams and leaders, the points that Chris brings out, the points and experiences that Chris share, I think is going to be relevant and meaningful to a lot of folks. Right? So Merry Christmas, happy Holidays, all of those things. I will be back at the new year with some new stuff. The website address for the show chatgpt experiment.com you haven't been there. You'll find archives of the episodes, some guides and articles, ways of getting a hold of me. If you want to do training with either myself or with your group or you go to workshop, you'll find ways of getting a hold of me there. And as always, if you've got an interesting nugget to share, please do and perhaps we can get you and it on the show to share with our listeners. Okay, so yeah, the very first, very first interview with Chris Dupre. Chris is the partner of a company called the Question First Group where he helps leaders and teams unlock better conversations, get stronger connections and make meaningful breakthroughs. The cool thing is he's a former army officer in the 82nd Airborne Division and he brings a deep leadership foundation built on presence, discipline and self awareness. And he's just an all around good guy, Ted Lasso and West Wing fan. So I hope you enjoy the episode and get something from it. So here is my conversation with my friend Chris Dupre. And as always, stay curious.
D
Okay, talk soon. So, hey, Chris, how you doing?
C
I'm good, Gary. Thanks for having me.
D
It's good to have you, and I really appreciate you joining me. So we could talk a little bit about some of the practical ways that ChatGPT has come in. So there's background. You probably see it too. Like, there's an awful lot of folks just kind of spewing out chatgpt nuggets, and they're saying all these technical things and they're giving cheat sheets. Right. And these. Yeah. And it really flies over the head of most people. Right. So are you finding something similar? Like you're having conversations and utilizing this thing? What are you finding out in the work that you're doing?
C
So I'm lucky. Now I work with a very small handful of clients in my little group. We are sort of pushing AI to look like. So in a they ask, you answer realm, we're going, okay. How can ChatGPT Generative AI change some of the dynamic of how we bring this to life? Right. So that's one segment. But then when I get to my peer groups, when I go out and talk to other executives in other places, it's more like you said, they know that it's here. They don't really know what it means. They hear things like CHAT GPT, they hear things like generative AI. And honestly, more often than not, people like, is John Connor gonna come back to try to save us?
D
That's exactly a little Terminator, like flying car jets and kind of things, Right? That's right. And yeah, and you're probably saying those.
B
Those are.
D
Those are some smart people you're talking to. And even those folks hear a lot of Charlie Brown teacher. Right. When this stuff starts talking, it's just like, I don't know, these are just buzzwords. They don't mean anything to me. And not quite sure how to process.
C
Those, but because we don't break it down into like. Like, the reality is, anybody that's used Google in the last few years, when you type in restaurants near. And then it puts me or the town that you're in, that's artificial intelligence. It's just a different wavelength of it. Right.
D
Baked into something we know. That's right.
C
Yeah, yeah. So, like, your Netflix, like, the algorithm is based on the same stuff that all this generative AI, large language. But, like, all that stuff is. And so I think as an industry, whether it's in marketing, in sales, in tech. It stayed in the nerd realm almost. And like, I say that with all the love in the world, but it's like, break that shit down Barney style for the people that are actually going to take it to use versus the coders who are like. Like, if you're a coder, you probably aren't listening to this and you probably are already eons ahead of the rest.
D
Of us and you're using a part of your brain that I don't even know exists in my.
C
Yeah, like, I don't know that that's a part of the brain. But for those business leaders who you're sitting there like, I know that AI is a thing, there's probably a couple thoughts going through your head, like, can I become more efficient? What does this mean for the workforce? Is this something that's going to help me? Or you're like, I don't like change and I don't want to do anything, so I'm going to pretend it doesn't exist. Like, I think those are sort of what's probably going through a lot of people's minds right now.
B
Right?
D
So you just opened some doors and let's go through it, man. I appreciate that. So let's get rid of the grumpy trolls, because we don't want to talk to the grumpy trolls. So we've got a couple options here. We've got, is this even worth looking at? Will this add any benefit to my business? And then the subsection of that is, if the answer is yes, I still have to understand how and what it means to my daily work, right? Not the big picture. So let's dig into a few for instances. So let's say, let's talk to the business leader for a second. What are you saying to the executives that are asking this question, Should I have my employees do this? Is this right for my business? Are there ways this would benefit me? So what are you saying?
C
Well, I mean, the, the answer is 100% yes. You have to think about this in terms of. This is a once in many lifetime transformation of the way in which data, the way in which work gets done. This is like much bigger than even probably the Industrial Revolution, right? Like, this is, this is huge. Now, that's all grandiose and blah, blah, blah, Cool. But the reality is, think about it like this. If you had 10,000 super smart workers that could work 24 hours a day, seven days a week, 365 days a year, that could do specific tasks that you told them, what would you have them do? Right?
D
And that's where most people just go to go, right? Because I don't know. I don't live in a world we don't know.
C
So. So we have to get to this point. It's like anything else. If, if you just hear we need to go do AI, you're like big, huge elephant, right? Can you eat a big huge elephant all together?
D
Listen, last week was Thanksgiving. I came pretty close.
C
You came close. You came close, right? But to eat your. So let's get.
D
The answer's supposed to be no.
C
Yeah, yeah. So, so like you got to carve that turkey up. Like nobody's just sitting there going, well, here's the bird. So I'm just going to throw the whole thing in my mouth, right? So you climb it up, you chop it up. The same thing's true with any new adoption of stuff. So before we can just go, hey team, here's AI. We have to.
D
And so just, just pause, right? Because how. Just AI aside, right? How often do you see that happening just in general, like, here's our new software, like, here's our new CRM. Like, here's good luck, you know?
C
Yeah. So, so, so think about every failed project you've ever had as a business leader. It probably went some way like this. So let's say that you're evolved and you go to Vistage, right? So you sit in a Vistage group or an e. You know, an entrepreneurial organization group or like any of those business owner groups and you hear a new idea and you run back to your company and you go, team, I just heard the best flipping thing ever. Here's what we're going to go do. And they all look at you and go, what?
D
What are we talking about?
C
Right? And, and, but you're like, no, we're doing it. And then it just comes crash and burn. Like we can take the ask, you answer. So somebody goes out and sees our friend Marcus speak. They are so fired up. We are going to answer our buyers questions. They're going to find us on search. Our salespeople are going to use it in the. Oh my God, this is going to be life changing like it was for Marcus. I can't wait. And then your sales manager goes, we're not putting pricing on the website. And then your marketing leaders, like, I don't think we should write three articles a week. I think we should. And it's like. And you sit there and your head.
D
Explodes or the phone rings, you know, Right. I Mean just this slight distraction and we all reassign our duties and then we wonder why nothing happened. All right, so let's.
C
So you.
D
You're a grandler, dude. Let's go through here. So let's talk about. Let's talk about two or three ways in which that average CMO marketing manager, someone responsible for content, someone's responsible for promoting and actually executing a strategy for business, could look at this as a problem solving model. Let's get into a few things here. So what do you say? Give me, give me one. What's the top of your head? What's the first thing that comes to top of your head when I say how this could be used as a problem solving partner in that realm?
C
So let's put some, let's put some caveats in here. We have done some sort of education, some sort of workshop to get everybody to understand what AI actually is. And they understand that it's not here to take their job, it's here to make them. I like to use the word supercharged. So it's like, how do we make everybody better? How do we gain momentum by using it right? So if those caveats are there and people get what we're doing, we have a system in place, all that stuff. For me, the first bit is literally, it's like so simple. Go to chat, GPT, tell it what you do and ask it, how can you help? That was one of the first things I ever did, Carrie. And it's because I didn't know, like, I had asked it at one point, like, write me a. Write lyrics for a cheesy love song in the key of C&4. Like, like I'd done that right? And then. But I didn't know what else it could do. I just hear all this stuff. So I just asked it that and it gave me this list. Okay, this is a good starting point. And then it's like, what's the hardest thing for me? So as a coach, as a speaker, like, I need to be present on LinkedIn, right? That's hard for me, brother. Like, it's just really like, I speak, I don't speak in well thought out LinkedIn posts. I speak in 10,000 sticky notes that I clearly see how they all connect. But if I were to just type it out, it's crazy, right?
D
And you're not alone there. There's a lot of people that, that can speak all day long, but can't organize a thought for a post that scares the heck out of them, right?
C
So it would take me let's call it, let's just call it 20 minutes to get something that would be worth typing, like worth posting, that you know, people would comment on, that would actually.
D
Help me or even just to organize and simplify with clarity what it is that you're trying to say.
C
Right. So here's the deal. So that would take me about 20 minutes. Well, I gave chat GPT three or four of my posts that were good like that said learn my style and now I just stream of consciousness type in and say generate, you know, hey, let's write another post. And I put it all in and it generates in that tone and that thing and it takes my ramblings into a message that's built out the way that I built it out when I've taken the time. But so what does that say? That saves me about 19 minutes every day.
B
Yep.
C
I, yep. And so that's like a very small example.
D
Yeah, it reminds me of, we have a residential service client and they have a call center that takes after hour calls. And you can imagine that most of the after hour calls, they're not pleasant. You know, they're not calling to say, hey, I just want to say congratulations on a fantastic company. No, there's usually an issue. Either it's an emergency or a complaint or something of that nature. So they had five years of these calls and what ends up happening is the call center actually logs them into a data note.
B
Right.
D
And then sends it over. And so they put all that note five years into a document and I said, hey, watch this. We threw it up into ChatGPT in 30 seconds. It took five years of notes, categorized it by category, summarized the issues and gave us things that we should probably look at and focus on. So to your point, rambling, just unconnected or just various notes thrown in together, it's very good at processing, summarizing and then giving you clarity.
C
Yeah, so, so the idea, so what's the first thing you do? I don't know. If you're trying to build your brand of your LinkedIn like that, that's a use case. If you're thinking about how do you use it in your, like it's, how can it supercharge your team? And this is, this is, I think the, the, the biggest mistake companies can make is thinking that it's a top down. Here's how I want you to use AI. That's not going to work. Right. Listen, I'm, I'm, I'm a gray beard at this point. Right. I'm going to use it the way that I'm going to use it and I'm going to learn from others, but I don't do some of the practical work that our team does at Impact anymore. Like, I talk to people, I. Right, but so we said, hey, go run experiments. Go, go, you know, mess around and see what you find. And oh, by the way, you run a great experiment that saves time. We're going to give you a bonus for, for all that time in there. Right? So it's like go play around, go test stuff. If you need to buy a tool, make sure it's all documented and you have, you know, like, go back to like seventh grade science where you've got the scientific method, like your hypothesis and all that stuff and see what happens. Because it ain't you and me, Kerry, that are going to figure out how a business is going to use AI. It's going to be the person that does the tasks over and over and over again.
D
And so I want to pause there because what you just said, there's an incredible value statement in what you just said. So the theme that I think a lot of folks need to hear is to give your employees permission to be curious. Right? So that's the first thing I just heard. Permission to be curious. Go try. Right?
C
Yeah.
D
But number two, and I know when we went through, when I went through the coaching program with you, when you were guiding me through the they ask you answer certification process, we did a lot of role playing and sharing. And so the other thing you just said is beyond just giving folks permission to be curious is once you learn something, don't have it be isolated in your mind and at your desk. Let's bring it out, let's share it and let's teach. Right?
C
Yeah.
D
So those are two, those are two nuggets that are fantastic for most companies to hear because they don't think that way. You know, it's amazing to me how many folks are frozen. You're, you're, you're a musician. I started sharing that AI for me, you opened by saying, you know, are we going to have the Terminator come back with this whole AI thing? Artificial intelligence. Those two words together scare the heck. They create a lot of anxiety and a lot of folks. And so early on when I started doing trainings, I said, AI, let's just, let's have a stand for amazing instrument. You know, this is a tool. But you still got to bring your perspective, your skill, your experience, your expertise. Just like the piano, Right. You can make it sound a thousand different ways. You don't have to play like Beethoven or Billy Joel. You can do your own. Yeah, but it still needs your input. Right. So that whole thing, I love that. Giving folks permission to be curious and then once you find something, come and share it. Good.
C
Yeah.
D
Good stuff.
C
Well, here's, so here's, let's just on this note, let's again go big CEOs, VP, like CM. Like, our job is not to go figure out the thing. Our job is to empower the folks that we work with to go figure out the things and then for us to maximize, to think about, okay, so now we can do this. So where can, where can the ship go now? Not like, how is everybody going to use, but like, like it's not that. Now you have to have some governing principles to make sure you. Of course, like, so there's, so there's nuance and things have to happen. But if you're a CEO going, I got to figure out this AI thing before I give it to my team, you will fail. Like, and listen, you're, you're super smart, you've been super successful, but the reality is if you're tinkering in day to day crap, you're not looking far enough out. I mean, you're only going to get so far.
D
And the perspective of the different positions you have in your company varies and the ability for folks to see how it applies to their work, to their customers, to their service, to their needs and their goals. Right. That's the, that's the key here. Yeah.
C
And so all of this just comes back to if you're a business leader who is like, how do I even get started? You have to understand the, what's possible and then you need to take it to your team and they need to understand before you go, we're going to run all these experiments, we're going to do all this stuff. You need to educate them on what artificial intelligence is and how you think it may be able to help your organization. And then you have to come up with how are we going to run experiments and what are our guidelines? That's business leaders. That's where your heads need to be. Not, not in the minutia yet. Get past that and you're then going to start playing the game of oh, wow, I didn't know my team could figure things out like this.
D
Yeah.
B
Awesome.
D
Hey man. So good. There's some gold nuggets here. I'm so glad you got to spend some time with me this morning and, and share your insights and your experience. It's always good talking to you.
C
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Podcast: The ChatGPT Experiment – Simplifying ChatGPT For Curious Beginners
Host: Cary Weston
Guest: Chris Duprey
Episode Title: From The Vault: Don’t Overthink It – Just Ask ChatGPT “How Can You Help?”
Original Air Date: December 2023 (Rebroadcast December 16, 2025)
This episode focuses on demystifying ChatGPT and AI adoption for business leaders and everyday users. Host Cary Weston revisits his very first podcast interview, featuring Chris Duprey—leadership consultant and partner at the Question First Group. Their discussion centers around practical, approachable strategies for integrating AI tools like ChatGPT into personal and professional workflows, emphasizing experimentation, curiosity, and real-world value over technical jargon.
“Go to ChatGPT, tell it what you do and ask it, ‘How can you help?’ That was one of the first things I ever did, Cary. And it’s because I didn’t know…”
– Chris Duprey, 12:35
“Permission to be curious. Go try. Right? ...once you learn something, don’t have it be isolated in your mind and at your desk. Let’s bring it out, let’s share it, and let’s teach.”
– Cary Weston, 17:53–18:15
“You still got to bring your perspective, your skill, your experience, your expertise. Just like the piano, right? You can make it sound a thousand different ways. You don’t have to play like Beethoven or Billy Joel. You can do your own. Yeah, but it still needs your input.”
– Cary Weston, 18:15
“Our job is not to go figure out the thing. Our job is to empower the folks that we work with to go figure out the things and then for us to maximize… where can the ship go now?”
– Chris Duprey, 19:06–20:10
Conversational, down-to-earth, and filled with practical wisdom and humor. Both Cary and Chris focus on demystifying AI and offering relatable ways to embrace technological change, with a heavy emphasis on real-world experimentation and continuous learning.
Stay Curious!