Hey leaders – Let’s get one thing out of the way: your team doesn’t need you to be a polished, professional prompt whisperer.
What they really need? To see you open up that AI tool, throw in a slightly awkward prompt, and say, “Well, that didn’t go how I planned.” (Side note: if you’ve attended one of my keynotes or workshops, you’re prompt won’t be awkward!)
🎉 Congratulations. You’ve just led out loud.
When it comes to AI, one of the issues I see too often is leaders talking the talk but not walking the walk. Many have barely touched a ChatGPT or Copilot, despite claiming how important AI is to their business. Others are quietly experimenting with AI behind the scenes, waiting until they’ve got it “figured out” before they bring their team in.
And while you’re off debating the perfect prompt, your people are sitting there thinking:
- “I guess this isn’t a priority.”
- “Maybe it’s risky?”
- “Or… maybe we’re just waiting for the AI fairy to show up with laminated instructions.”
Spoiler: she’s not coming.
Also: laminated anything is the BEST. I desperately miss my laminator.
The Real Risk? Staying Silent
You could have the most impressive AI policy known to HR-kind. You could be sitting on enterprise-grade tools and enterprise-grade budgets.
But if your team never sees you use AI, all they’ve got is speculation.
They’ll assume it’s not for them. Or it’s only for the data people. Or that if they try and fail, someone will give them “that” look over Teams.
“Silence doesn’t create safety. It creates suspicion.”
And here’s the wild thing: you don’t have to get it right. You just have to get it going.
Why “Show & Fail” Is a Leadership Power Move
Recently, while speaking to over 1,000 senior leaders at a global bank, I asked how many of them felt confident using AI in their everyday work. Most did NOT. In fact, fewer than 10% felt they were rockin’ the whole AI thing.
When I asked another group of leaders how many of them were waiting until they “understood it better” before showing their teams – they laughed…and almost every hand went up.
The problem isn’t tech. It’s hesitation.
And hesitation is contagious.
Let’s say you try prompting ChatGPT to write a client email.
You forget to include tone. Or context. Or… you know, a point.
And it sends you back something that sounds like it was written by a caffeinated intern who’s watched one too many TED Talks.
Excellent. You now have a teachable moment.
“Your team doesn't need a genius. They need someone brave enough to go first.”
FIVE Ways to Practice “Show & Fail” Leadership
Ready to model a culture of confident imperfection?
Start here:
✅ 1. Narrate your AI usage like a cooking show
Next time you use AI, say what you’re doing out loud—yes, even if you’re talking to yourself on Zoom. (We’ve all been there.). Remember you’ve got my PREPARED prompt framework so that should be your foundation.
“So, I told it the persona, stated my request, explained the context, added an aim…and asked it to keep it punchy but polite. Let’s see what we get.”
Let your team hear how you think through it. You can even make it a game that everyone claps when they see “gamechanger” or “synergy” in an output.
✅ 2. Launch a “Fail of the Week” tradition
Kick off your next team meeting with your most gloriously weird AI result. Encourage others to bring theirs.
“Last week, I asked Copilot to write a report summary. It turned into a Shakespearean sonnet. So… not quite what I was after.”
“Failure isn’t weakness—it’s the proof you’re experimenting.”
Make it a ritual. Make it safe. Make it funny. Just make it ok to share and demonstrate struggles so you can help each other work through them.
✅ 3. Use the 20-60-20 framework like a pro
Your job:
✅ First 20% – Set the task, provide context, write the prompt. BE A LEADER.
🤖 Middle 60% – Let AI do the heavy lifting, drafting, data crunching.
✍️ Final 20% – Review, refine, and add your sparkle. BE A HUMAN.
Say it out loud:
“I gave it the context, it spit out the draft, and I made it sound like I wasn’t a robot raised in a conference room.”
“AI isn’t plug-and-play. It’s poke-and-tinker.”
✅ 4. Build “Show & Fail” into meetings
Try this prompt at the start of a weekly team sync:
“What’s one thing you tried with AI this week – good, bad, or totally bizarre?”
Everyone shares. No pressure. No judgment.
Just humans learning how to work with machines… and each other.
✅ 5. Celebrate the awkward middle
Remind your team that you are still figuring it out. When they see you iterating, they stop expecting perfection and they start participating.
Try It This Week
Your Homework
Pick one moment - just one - where you’ll “Show & Fail.”
- Narrate a prompt.
- Share a flop.
- Ask someone what they’ve tried.
- Let your team know it’s not about getting it right. It’s about getting started.
“You don’t need to be the AI expert in the room. You just need to be the first one willing to fail out loud.”
And if you or a leader you know is still hesitating? Let’s talk about a talk. I work with teams and organizations to help shift the mindset, build confidence, and create real momentum with AI.
Because it turns out, leading through change doesn’t mean having all the answers.
It means showing up, trying something new, and inviting others to do the same—awkwardly, imperfectly, enthusiastically.
That’s how we move from AI-aware to AI-empowered.
