Engaging Every Team Member in Your AI Journey

This post is inspired by a great comment from

in our community who shared:

“Getting people on board is interesting in our small team agency of just 7. I thought it would be easier... I’ve been showing each of them how it can be a win in their area of focus. A few have jumped right in… others still stay on the outside.”

If you’re in a small team, you’ve probably felt this too. You show someone an amazing AI shortcut and expect them to be all in, but instead, they hesitate, nod politely, and move on. Totally normal. Here are a few things I’ve seen work to move the needle, without forcing it.

Start with Personal Pain Points:

It’s easy to default to a general “AI is the future!” pitch—but people don’t adopt because of trends. They adopt when something helps them solve a daily frustration.

Ask, “What’s one part of your job you’d love to spend less time on?”If someone dreads writing reports, show them a template that drafts it in minutes. If they’re stuck in repetitive brainstorming, introduce an AI tool that gets the creative juices flowing. When AI solves something that matters to them, they lean in.

Pair Up Your Champions:

Instead of trying to win over skeptics yourself, let your early adopters do the talking. Pair a curious-but-hesitant teammate with someone who’s already made a win using AI. A short screen share, a quick demo, a simple “Hey, look how I used this” moment goes a long way. It feels way more relatable than a formal training session.

Celebrate Micro-Wins:

Create a simple #ai-wins channel to share quick success stories. Even a one-line win like, “Used ChatGPT to draft our first blog outline in 10 mins 🙌” can spark ideas. Visibility is key—when people see their peers making progress, the barrier to trying it themselves drops.

Make Space for Exploration:

Host 30-minute “AI office hours” each week. No agenda—just a space to share questions, wins, or even flops. It lowers the pressure and turns learning into a conversation. Some of the best ideas we’ve tried started in these casual sessions.

Keep the Momentum Going with Monthly Shares:

One of our favorite rituals is our monthly What’s New with AI meeting. We invite one person from each department to share (just 5 minutes) something they’re testing, learning, or building with AI. We rotate the speakers so everyone gets a voice—regardless of role or experience. It’s been one of the most powerful ways we’ve kept energy, inspiration and ideas flowing across the org.

Getting your whole team on board with AI isn’t a one-time push—it’s a rhythm. A mix of small wins, shared learning, and consistent encouragement. When each person sees AI as theirs, not just yours, that’s when the magic happens.

Let them go at their own pace—but don’t stop planting seeds. You never know when one spark will catch.

2 comments

MyZone AI Accelerator

skool.com/myzoneai

Where entrepreneurs and AI enthusiasts learn, share and transform into AI-first organizations—together in a friendly peer community. No-solicitations!

Leaderboard (30-day)