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Most AI adoption fails because teams are scared to experiment.
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Play is the missing link — safe, structured, and surprisingly effective.
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This guide shows CEOs how to turn “just try it” into ROI and repeatability.
Why Your AI Strategy Needs Play Before Policy
Most corporate AI strategies are missing the one thing that works: permission to play.
We don’t mean sending staff a list of approved apps or making them sit through another webinar on responsible AI use. We mean creating low-stakes, high-reward spaces where people can mess around with tools like ChatGPT, Microsoft Copilot, and Gemini, with zero fear and a lot of laughter.
Remember the bubble wrap popping app from the iPhone launch days? Pointless, right? And yet, it showed millions how to tap, swipe, and interact with a touchscreen. That moment of play unlocked mass adoption.
AI needs its own version of that.
The 3-Phase CEO Play Framework
We’ve worked with dozens of exec teams trying to get generative AI off the ground. The ones who succeed all follow some variation of this framework — even if they don’t call it that.
Phase 1: Permission to Play
Start here. Not with policy. Not with fear. Just with permission. Most employees are already dabbling with AI tools on the side — but they’re hiding it. They’re unsure if they’ll get in trouble. CEOs need to blow that door wide open.
Announce publicly that your company supports playful, responsible AI exploration. Even better, share your own experience — maybe the time ChatGPT helped you draft an awkward client email, or write a birthday poem in the style of Shakespeare.
Celebrate silly use cases. Create a Slack or Teams channel for AI wins and weirdness. Run a meme contest: “Most Useless AI Output.” Give out stickers. Yes, stickers.
The goal here isn’t productivity. It’s psychological safety. Adoption begins where fear ends.
Phase 2: Structured Playground
Now that your people feel safe to explore, give them a structure to do it well. Call it an AI Play Sprint, a “Hack-A-Week,” or “Promptapalooza” — whatever feels on-brand for your culture.
Here’s a teaser of what this might look like:
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Teams challenge themselves to use ChatGPT, Copilot, and Gemini for something, anything.
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They remix real work: summarise a board paper, rewrite a cold email, generate ideas for the next campaign.
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They share the best, worst, and weirdest outputs.
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They reflect on what surprised them: “Did AI make my job easier, or just funnier?”
You’ll be shocked at what surfaces. We’ve seen teams cut report writing time in half, reduce customer support tickets, and even discover new product ideas — all from play.
Want the full sprint plan, ready to run with your team? We’ve built it. And that’s just the beginning for subscribers. (More on that below 👀)
Phase 3: Turn Play into Practice
This is where you move from chaos to capability.
Some teams will have stumbled into actual productivity gains. Some will have just had a good laugh. Both are valuable. Now it’s time to harvest and scale the useful stuff.
Start with simple asks:
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“What AI use case did you actually keep using?”
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“Can we turn that into a repeatable process?”
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“Can you teach it to someone else in 10 minutes?”
Use ChatGPT or Gemini to turn one team’s prompt into a template. Use Copilot to automate an Excel process they prototyped. Build a library of “AI Plays” anyone in the company can browse and remix.
You’re not building an AI strategy. You’re building AI fluency. At scale.
Where This Gets Real
What we’ve shared so far is the open playbook. But for subscribers, we go full tilt:
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How to run each phase with detailed activities, tools, and templates.
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20+ ideas to make AI part of real work — without killing the fun.
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Agendas, cheat sheets, CEO talking points, and even internal comms templates.
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The exact prompts and playbooks teams are using to generate real value with AI tools today.
Oh, and there’s an AI Slam Day at the end — with trophies. Because if you’re not having fun, you’re doing it wrong.
Final Thought for Leaders
If your team hasn’t had its “bubble wrap pop” moment with AI, it’s not because the tech isn’t ready. It’s because your culture isn’t.
You don’t need another strategy deck. You need a playground. Start with play. Then systemise what sticks. The future of AI adoption isn’t just technical — it’s cultural.
Your job? Give your people permission to try, screw up, laugh, and learn.
Then stand back and watch what happens.
👉 [Subscribe to unlock Part Two: The AI Play Sprint Toolkit for Leaders]
Includes agendas, prompts, templates, and bonus activities for Phases 3 & 4. Because the best way to lead AI is to play with it first.
