2026.24: You Took Your Team Hostage

Written By Jason Tate

Happy Friday friends, this week from a smoky Toronto.

You may have noticed there was no letter last week. I spent ten days at the Calgary Stampede, where I’ve had the honour of hosting the music festival at Nashville North for eighteen years now. 33 of the best bands and the best crowds on earth. I came home to a city smothered under forest fire smoke. And to a heavy heart for the families losing so much this fire season. If that’s you, I’m thinking of you.

Now, back to work.

Standing on a stage for eighteen years teaches you one thing fast. You cannot force a room. You can set the stage, hold the mic, prep the bands, own the schedule. None of it makes people lean in. The second a crowd feels stuck there, they reach for their phones, and you’ve lost them. You just don’t always know it yet.

Seth Godin wrote something this week that struck that nerve. “The moment you start treating your customers as captives, they begin to make other plans.” He was talking about customers. I couldn’t stop thinking about my audience at Nashville North, and the teams I work with in my corporate life.

Because that’s exactly what a lot of leaders have been doing with AI. They bought the tool, dropped it on every desk, and called it adoption. Or worse, an “AI transformation.” They could do it because their team is a captive audience. Nobody quits over a clunky tool, the way they would walk out of a music festival. Captive is never the same as engaged. So they did what trapped festival-goers and employees do. They checked out and reached for their phones.

Let’s break it down.

Signal:

YOUR TEAM ALREADY LEFT. THEY JUST DIDN’T TELL YOU.

Here’s the number that’ll ruin your Friday. WalkMe surveyed 3,750 workers across 14 countries this spring. Roughly 80% are avoiding or flat-out rejecting the AI their own company handed them. More than half quietly did the work by hand in the last month instead of touching the tool. A third haven’t opened it at all.

You didn’t roll out AI. You rolled out a very expensive “thing” your people skirt around.

And the trust gap underneath it is worse. Only nine percent of workers trust AI with a complex decision. Among executives, it’s sixty-one. The people who bought the tool believe in it. The people who have to use it every day do not. That is not an adoption problem you can train your way out of. It’s a whole room quietly reaching for their phones.

Gallup put a second number on the mood this year. Sixty-nine percent of employees are disengaged, the highest since 2014. Sit with that. Engagement actually peaked in 2020, in the thick of the pandemic. Your people were more bought in during lockdowns than they are today. Some of that is from AI dropped on people who never got a say. You cannot mandate belief. You can only mandate compliance, and compliance quietly routes around you.

Scale:

YOU CAN’T ORDER SOMEONE TO GET BETTER.

Here’s where most leaders got the goal wrong on day one. They bought AI to make work faster. Speed was never the prize.

A sharp piece in Harvard Business Review this week, from David Duncan and Tyler Anderson, makes the case cleanly. The machine hands you a first draft in seconds. So the value stopped being the draft. It became the judgment to look at that draft and say what’s wrong with it. Faster is cheap now. Better is the whole game. And better only happens when a human with taste is in the loop, not when a human is told to get out of the way.

A second HBR piece, built from three CHROs who have actually run this, points at the fix. It isn’t a better tool. It’s how you bring people in. Connect the AI to work they already care about. Give them space to test, experiment, and get it wrong without a penalty. Ask for their input and let them shape how it gets used, not just on the receiving end of the memo. Tell them the truth about what you don’t know yet. Trust gets built by being straight, not by being certain.

Read those two side by side and the pattern jumps out. The captive route treats your people as a cost to remove. The other route asks for their judgment, which is what you actually pay them for.

I wrote about this back in May, in Let the Machine Lift. You Lead. (2026.17). AI compresses the time a task takes. It does not compress the responsibility for getting it right. The moment you forget that and treat your team as furniture to work around, they start making other plans. Same as Seth’s customers. Same as any room that feels trapped. They reach for their phones.

Deep Dive:

YOU CANNOT FORCE A ROOM. YOU CAN ONLY GIVE THEM A REASON TO LEAN IN.

So here’s what to do this week.

Pick one AI tool you have already rolled out. In your next team meeting, don’t tell them how to use it better. Ask them one question. “What is this thing getting wrong, and what would you change?” Then shut up and write it all down. Before the meeting ends, pick one thing they said and change it, out loud, in front of them.

That’s it. One tool. One honest question. One change they can see. You are not asking for buy-in. You are handing back the pen. People don’t find workarounds for the tools they helped implement.

Thanks for reading!

Hit reply and tell me one thing your team would change about the AI you gave them. If you don’t know the answer, that is the answer.

The newsletter isn’t the conversation. The conversation is the conversation.

See you next Friday.

Best,

JT

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Sources

From Signal to Scale

  • 2026.17 - Let the Machine Lift. You Lead.

Jason Tate https://jasontate.ca
Next

2026.23: Name Your AI and You Just Built the Perfect Scapegoat!