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AI Enablement

How to Get Buy-In From Your Team on AI Adoption (What Worked With a 15-Person Team)

Rob Cressy
TL;DR
  • The short answer to how to get buy-in from your team on AI adoption: make the first project a gift for a teammate instead of a task for the business.
  • Set the floor low enough that your least technical person clears it. Thirty minutes, no quality bar, no wrong answer.
  • Create a second award for the biggest leap, so the person furthest from AI has something to win.
  • Let the team redesign the thing live. What they change becomes what they own.
  • Measure participation, not enthusiasm on the call.

If you are looking for how to get buy-in from your team on AI adoption, the move that works is smaller than a rollout plan. Give the team one project where the point is a person, not productivity. People who do not care about AI still care about the teammate whose name they drew, and adoption shows up as a side effect of that.

I watched this land last week on a call with a fifteen-person team I coach. Their founder had told me two days earlier that they wanted a team game with AI where everyone created something in seven days. No other context. So I built one, brought it to the call, and by the end the least technical people in the room were the ones talking loudest about what they were going to make.

How Do You Get Buy-In From Your Team on AI Adoption?

Make the first use case a gift.

Here is the game I brought them, which we called The Gold Drop. Seven days. Every person secretly draws one teammate's name, like a secret Santa. They read that teammate's personal manifesto, which the team had already written together in a previous session. Then they use AI to create one thing that makes that person feel seen.

The principle underneath it is simple. See the gold in others.

Notice what that structure does to the resistance. Nobody has to believe AI will make them more productive. Nobody has to sit through a tool demo. They have to make something for a colleague, and AI happens to be the fastest way to do it well. By the end of the week, every person on that team will have run a real prompt, iterated on a real output, and shipped something they cared about.

That is the whole shift. Most teams get handed a tool and asked to find a use for it. This hands them a reason and lets the tool follow, which is the same instinct behind everything I have learned about how to get your team to actually use AI.

Why Does AI Training Fail to Create Team Buy-In?

Because training is aimed at the wrong thing.

A training session teaches capability. Buy-in is about motivation. The gap between them is where most AI rollouts die, and you can hear it in the feedback. The founder on this call said the exact failure mode out loud when I asked what would make the game great. They said participation. Then they described the pattern they were worried about: an hour where everyone says that was so cool, followed by one-on-one reports where the best part of the week was learning from Rob, followed by not much happening.

That is what a great training session produces. Enthusiasm with no artifact.

A challenge with a deadline, a recipient, and a public reveal produces artifacts. The distinction matters enough that I treat it as the difference between teaching a team and changing one, and it shapes how I structure every session, including what an AI workshop for executive teams actually looks like.

What Is a Good First AI Project for a Team?

One with a human recipient, a short deadline, and no possible wrong answer.

When the AI generated the idea menu for this game, it came back with options running from simple to ambitious:

  • A poem or spoken word piece built from the person's own lines
  • A playlist where every song connects to something they wrote
  • A movie poster or trading card of their life
  • A letter written from their future self, five years in
  • A one-page website they can send to their family
  • A comic strip, a short song, a highlight reel write-up

The team picked the spoken word piece first, so we built it live. Sixty seconds, generated from a manifesto, then read out loud on the call by a teammate who said they like dramatic reading and try to feel what they are reading.

The room went quiet. That is the moment buy-in actually happens, and no slide deck creates it.

How Do You Get Team Members Who Are Afraid of AI to Participate?

Set the floor low and give them their own award.

The floor first. Thirty minutes is enough. No minimum quality bar. No wrong answer. When you have one person on the team building dashboards with AI every day and another person who does not know where to start, design for the second person. The star will exceed the bar no matter where you set it.

Now the award, which is the part most leaders skip. We created two on purpose.

Gold Standard goes to the creation that made its recipient feel the most seen, voted by the team.

Zero to One goes to the biggest leap by whoever was furthest from AI when the week started, chosen by the founder.

That second award is the entire buy-in mechanism for your beginners. Your most advanced person is going to win any quality contest, which means everyone else has already lost before they start. Give the beginner a category they can win and they show up. I tied both awards to a recognition program the team already ran every month, so the game plugged into culture that existed instead of asking for new attention. That kind of grafting is most of what building an AI culture in a small company comes down to.

One more guardrail worth stating out loud to the room. If you get stuck, type into the AI that you are stuck and ask it to keep asking you questions until it understands what you want. And asking a teammate for help is encouraged.

How Long Should a Team AI Challenge Last?

Seven days, with a thirty-minute expectation inside it.

Long enough that a busy week does not kill it. Short enough that nobody forgets it started. A thirty-day challenge with a new task every day sounds ambitious and produces dropouts by day four.

The deadline does something else too. It forces version one out the door, and version one is where the real lesson lives. On the call I built a small interactive game in about ninety seconds, looked at it, and immediately started listing everything wrong with it. The founder stopped me. Nine months ago, they said, we would have estimated a day or two for that. We just built it in ninety seconds from a blank concept.

They were right, and they were using my own rule on me. We do not disqualify the thing. Your team will do the same thing to their own work, so name it before the week starts.

What Prompt Should Someone New to AI Start With?

Give them the whole prompt, written out, so the blank page never happens.

Here is the starter prompt I handed the team:

I am creating a gift for a teammate using their personal manifesto. Here is their manifesto. [paste it] Here are three things I know about them. [list them] I want to create something that makes them feel seen and celebrated. First, ask me five questions to understand them better. Then give me five different ideas for what I can create, from simple to ambitious. I am new to AI, so for each idea tell me exactly how I would make it.

Three things are doing the work in there, and they are worth teaching your team as separate moves.

Lead with the outcome. The first sentence says what you are making and who it is for. Everything after it is context.

Ask the AI to ask you questions. This is the single biggest level-up for a beginner. AI does the thinking about what it needs, and the person only has to answer. On the call, the team answered five questions about their teammate in under two minutes and the output was dramatically better for it.

Say you are new. Adding I am new to AI, so tell me exactly how I would make it turns every idea into instructions. Most beginners never think to say it.

One routing note to save your team time. Send anything visual to ChatGPT, since it generates images. Send anything interactive, like an artifact or a small web page, to Claude. Match the tool to the gift. Getting that kind of practical routing in front of people early is most of training your employees to use AI effectively.

How Do You Measure AI Adoption Buy-In on Your Team?

Count creations shipped, not hands raised.

Participation rate is the honest number. How many people out of the total actually made and delivered something by the deadline. Everything else is a proxy that flatters you.

Two secondary signals tell you whether it will stick.

The first is whether the team started redesigning the thing without being asked. On this call, three people changed the game live. One wanted it visual rather than only spoken, so we built a visual, interactive version on the spot. One wanted variety, since fifteen poems would get repetitive. One wanted to hand-draw the names themselves and add their own creative touch to the draw. I folded all three in during the session. Participation gets manufactured at design time, and a game people helped build is a game they show up for.

The second signal is whether anyone transfers it. Late in the call, the youngest person on the team said the thing that mattered most. It is so easy to make someone's day, especially with the ideas we have with AI. That is the sentence you are fishing for. Once someone can do this for one person, they can do it for anybody, and that muscle walks straight into how they handle customers, vendors, and hiring. Leaders reach this point without any technical background at all, which is the whole argument for how you lead AI transformation without a tech background.

Run This With Your Team This Week

  1. Pick the human. Everyone secretly draws one teammate. Randomize it, or let someone on the team own the draw and make it their own.
  2. Give them source material. A personal manifesto works. So does a set of values, a bio, or three sentences each person writes about themselves.
  3. Hand out the prompt. Copy the starter prompt above. Do not make anyone write their own on day one.
  4. Set the floor. Seven days, thirty minutes is enough, no wrong answers, ask a teammate for help.
  5. Create two awards. One for the best creation by team vote, one for the biggest leap from whoever started furthest from AI.
  6. Ask what would make it great. Go around the room, let each person answer and call on the next, and change the design based on what you hear.
  7. Do the reveal together. Live, out loud, on a call. The reading is the moment.
  8. Count the creations. Participation rate is your number.

Why the Gift Frame Works

One person on that call made an observation about how targeted everything has become. Ads follow you off the platform, personalization follows you into every app, and shutting the noise off has gotten close to impossible. They were right, and it gave me the frame for the whole game.

We live in a world of manufactured personalization. The human answer to it is real-time personalization. Here is what I know about you. Here is what I appreciate about you. Here is a thing I made for you, this week, because I thought about you.

AI makes that cheap enough to do for an entire team in a week. Your people will feel the difference immediately, because almost nobody is doing it.

Getting buy-in from your team on AI adoption stops being a persuasion problem the moment the first person hears their own words read back to them and understands that a colleague spent thirty minutes making them feel seen. Nobody argues with that. They just ask when they get to make one.

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Rob Cressy
Rob Cressy
AI Enablement Coach helping entrepreneurs and leaders go from AI curious to AI dangerous. 1,000+ days of daily AI usage. Host of The Undeniable Leader podcast.