Once Upon a Time, a Smart Team Got Stuck

A smart team. A serious problem. A hidden failure in the room: the collaboration had become heavier than the work.

“This shouldn’t be this hard.”

And it wasn’t the work making it difficult.

The Room That Found Something Better

A university group, mid-discussion on an AI initiative that had real implications. Marketing wanted to move. An opportunity to improve the applicant experience, reduce friction, and stay competitive. IT wanted to be careful: systems, data, obligations that don’t tolerate shortcuts. The registrar kept pulling the conversation back. Their responsibility stretched across years. Records that don’t get a second chance. And the provost held the institution’s name, whatever happened.

They had been moving. Something honest had started in the room. Then one voice pulled it backwards – not circling, backwards. The big questions came back up again, questions the group had already moved through. Relevance. What gets lost when automation moves in? Whether the institution would recognize itself on the other side.

One leader leaned back, did his best Al Pacino, and quoted the Godfather: “Just when I thought I was out, they pull me back in.”

The room laughed. It was the most honest thing that had happened in an hour.

I stopped the work and worked on the team, specifically with the registrar. Not in front of the room. With her. Because underneath what she kept raising wasn’t opposition to AI. It was something sharper: what happens to her staff when this lands. People she had hired, trained, and was responsible for. That fear hadn’t been named yet. It had been showing up as friction.

Once it was named, I asked the room: What future are you trying to avoid here, and why does that future feel inevitable to you?

Different question. They answered it differently.

What came out wasn’t opposition. It was expectation – each person carrying a version of how this ends badly, shaped by something they had seen before.

Once the room understood what the registrar was actually carrying, something shifted. The annoyance dissolved. They stopped debating around her and started moving toward her. Someone said, “We’ve got your back.”

That’s when the work could continue.

“Tim, if it’s that straightforward, what gets in the way?”

Complexity isn’t the issue. This isn’t rocket surgery, but it does require someone who can open up a team.

What gets in the way? If you’re the leader – or an HR rep, sorry to say – it’s likely you.

You can mean well, but you can’t always make it safe. You have an agenda – don’t feel bad, that’s your job.

Peers compete for attention, contractors protect margins, bosses sign the cheques, and HR represents the organization first.

People in the room know this. It determines what they’ll hold back.

As a leader, you’re better off contributing to the discussion than trying to lead it.

Best,

T

P.S. If your team, partnership, or project is working harder on each other than on the work, or is getting started and wants to set up for success, let’s talk. I’m neutral, I build trust quickly, and I’ve practiced this dozens of times a year.