Why CEOs Fail at AI Implementation (And the Simple Fix That Works)
You know AI could transform your business. You’ve heard the success stories. You understand that ChatGPT and similar tools represent a massive opportunity. But every time you think about rolling it out to your team, you hit the same wall: Where do I even start?
If you’re a business leader feeling overwhelmed by AI implementation, you’re not alone. Most executives make the same critical mistake that dooms their AI initiatives before they begin. But there’s a surprisingly simple fix that successful companies use to unlock AI’s potential.
The core insight: Stop trying to figure out AI yourself. Instead, give your team permission to be curious and discover what’s possible.
The Fatal Flaw Most Leaders Make
Here’s how most AI rollouts fail: A CEO attends a conference, gets excited about AI’s potential, and returns to the office declaring, “We’re implementing AI!” Sound familiar?
Chris Duprey, lead coach at Impact and veteran business consultant, sees this pattern repeatedly. “Think about every failed project you’ve ever had as a business leader,” he explains. “You hear a new idea, run back to your company and go, ‘Team, I just heard the best thing ever. Here’s what we’re gonna do.’ And they all look at you and go, ‘What are we talking about?'”
The problem isn’t the technology—it’s the approach. When leaders try to become AI experts before empowering their teams, they create bottlenecks that kill momentum.
The fix: Recognize that your job isn’t to master AI. It’s to create the conditions where your team can discover how AI solves their specific challenges.
Give Permission, Then Get Out of the Way
The most successful AI implementations start with a simple but powerful strategy: organized experimentation.
Instead of dictating how AI should be used, smart leaders establish guidelines and let their teams explore. Duprey’s approach at Impact is telling: “We said, ‘Hey, go run experiments. Go 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.'”
This works because the people doing the daily tasks understand the pain points better than anyone in the C-suite. Your customer service team knows where they waste time. Your marketing team knows which processes frustrate them. Your sales team knows where they need better tools.
The key insight: It’s not you who’s going to figure out how your business uses AI—it’s the person doing the tasks over and over again.
Start with the Simplest Question
Before your team can experiment effectively, they need to understand what’s possible. Duprey recommends the most straightforward starting point: “Go to ChatGPT, tell it what you do, and ask it, ‘How can you help?'”
This isn’t about becoming an AI expert overnight. It’s about removing the mystery and helping people see concrete applications. When team members understand that AI can help with real problems—writing clearer emails, summarizing long documents, brainstorming solutions—they start seeing opportunities everywhere.
For Duprey personally, this approach transformed a daily struggle: “LinkedIn posts would take me about 20 minutes to get something worth posting. I gave ChatGPT three or four of my good posts, told it to learn my style, and now I just stream-of-consciousness type and it generates posts in my tone. That saves me about 19 minutes every day.”
Small wins like this build confidence and momentum across your organization.
The Bottom Line
AI implementation fails when leaders try to control every detail from the top. It succeeds when you create space for discovery, establish clear guidelines, and trust your team to find solutions.
Your role as a leader isn’t to become an AI expert—it’s to think strategically about where your newly empowered team can take the business. The tactical discoveries will come from the people closest to the work.
This insight comes from a conversation with Chris Duprey on The ChatGPT Experiment podcast. Want to hear the full discussion about AI implementation strategies? [Listen to the complete episode here.] If you’re exploring AI for your business and want practical guidance without the technical overwhelm, subscribe to the podcast for more conversations like this.