The First Rule of AI Club - Make It Fun
One of my earliest Copilot sessions at Microsoft was nothing like the typical training most employees were used to. A few hundred curious, and let’s be honest, skeptical, people joined the call, most of them expecting a technical deep dive, maybe some feature walkthroughs, or a safe list of best practices. Instead, they got something else entirely.
Everyone showed up expecting a training. What they got was chaos, creativity, and a little rebellion.
It was one of my first Copilot sessions I led at Microsoft, and things didn’t go the way most people expected. And that was the point.
We weren’t there to go over bullet points or watch slides. We were there to play with AI. And not everyone appreciated that shift.
10 minutes into the session, someone typed in the chat, “Why isn’t this a technical overview?” The tone wasn’t curious; it was clearly frustrated. But I didn’t flinch. I responded plainly, “This is an experiment. We’re here to explore prompting in creative ways. If this isn’t for you, feel free to drop.” A few seconds later, I heard it; beep, beep, beep, then more beeps.
People were dropping from the call like it was a fire drill.
But I didn’t change course. Not because I was trying to be provocative, but because I knew we were dealing with something different. Copilot wasn’t just another tool to be mastered. It wasn’t a new spreadsheet function or a platform you could learn with a few walkthroughs. It was a new way of working entirely, and that meant we needed a new way of learning.
The Magic of the Ones Who Stayed
The people who left wanted structure. They wanted a clear syllabus, a checklist, a familiar sense of control. The ones who stayed? They were the builders. The explorers. The ones willing to feel a little uncomfortable in order to see what was possible.
What happened next still lights me up. I guided the group through a series of playful prompts, ones I had carefully chosen to stretch their thinking while keeping it fun. It started with a few brave souls typing their results into the chat. Then something shifted. People couldn’t type fast enough. The chat window exploded with screenshots, reactions, and custom prompt variations. It became this energetic swirl of creativity where everyone was building on each other’s ideas.
It didn’t feel like a corporate training anymore. It felt like we were in on something. Like we’d discovered a secret club where work could be both joyful and bold. That shared spark created a kind of belonging that slides and checklists never could. People weren’t just learning, they were connecting. And it stuck. Many of those folks became internal AI champions. They kept showing up to learn, to experiment. They brought their coworkers, their teams, and their manager. Week by week, my audience grew like wildfire.
When Learning Becomes a Movement
That spark ignited something more powerful than a polished demo ever could: community, curiosity, and creative momentum. People messaged me afterward saying things like, “This blew my mind,” or “I didn’t know AI could do this,” or “I can’t wait to share this with my team.” Many of those attendees became some of the strongest AI advocates within the company. They kept showing up week after week, and the audience kept growing.
That day taught me something I now thread into every workshop, coaching session, and course I lead: play is not optional. It’s the secret ingredient most corporate learning environments forget.
Because play creates psychological safety.
It signals to people that it’s okay to try, to stretch, to fail, and to keep going. That’s how real learning sticks. Especially with AI, where the biggest hurdle isn’t the tech; it’s giving yourself permission to take that first awkward step.
And that step becomes a lot easier when the prompt is, “Give me a superhero persona based on my Teams messages,” instead of, “Write a three-point executive summary of this report.” One sparks interest. The other reinforces fear of being wrong.
Why Serious Work Needs a Little Weird
Since then, I’ve worked with global enterprises, trained executives, and helped build large-scale Copilot adoption strategies. Every time, I bring in fun. Not because I’m trying to be cute, but because I know it works. The leaders who engage in the weird, creative prompts are often the ones who go on to lead the most transformative use cases. They see beyond email summaries and meeting recaps. They imagine what’s possible.
I once disguised an advanced prompting workshop as a creative writing challenge. The prompt was to invent an alien species and describe their workplace culture. In reality, I was teaching chain-of-thought prompting, variable use, and role simulation, but no one was intimidated. They were too busy having fun. And that’s the point. When learning is joyful, adoption becomes natural.
Don’t Know Where to Start? Try These.
To get started, here are a few prompts that have delighted and surprised even the most skeptical teams:
“Based on my work emails and calendar events from the past 7 days, give me a superhero name, backstory, and signature catchphrase. Include my arch-nemesis too.”
“Turn my job into a movie plot. Cast a famous actor to play me. Write the movie trailer script with dramatic narration.”
“Pretend you’re an alien trying to understand my job based only on my last 10 emails. Translate them into your alien language and explain what you think I do.”
“Given my current skills and interests, create a futuristic job title for me in 2035, complete with job description and company perks.”
“Write me a note from ‘future me’ in 5 years, telling me what I’m doing well right now and what I should be less stressed about.”
These prompts aren’t just gimmicks. They’re cognitive entry points. They disarm skepticism and invite people to engage. From there, you can introduce more advanced concepts, connect them to business workflows, and scale from delight into ROI.
Don’t Start With the Features. Start With the Spark.
If you’re rolling out Copilot or any AI tool in your organization, don’t start with the feature list. Start with a spark. Make room for laughter. Build a sense of community. Let people see themselves not just as users of AI, but as co-creators of what’s possible. The ones who stay through that discomfort? They’re the ones who’ll shape the future with you.
Prompting like a rebel,
Yen Anderson