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“We need to roll out Claude Cowork but we can't seem to get moving”

Toby White · August 2026

I've had more or less exactly this conversation with ten or twenty large enterprises over the last month. Sometimes it's not Claude, it's Microsoft Copilot Cowork, but anyway — these organizations know that rolling out access to a general purpose agentic AI tool is key to the next step of the transformation — but they've got stuck.

“The head of IT promised me an answer in June.”

“CISO have been redrafting this policy for the last 6 weeks.”

“The business are pushing us hard on this but they can't even tell me which version of Copilot they want.”

“I heard we should be using Cowork but last time I tried to introduce a new vendor it took us 12 months.”

To be honest I think most of the people in these discussions don't even have a shared vocabulary for what they are talking about.

In almost every case these internal conversations have been circling for weeks; only a few organizations have actually managed to break out and get deployments moving, and we saw what made the difference for them.

We've been seeing the same patterns everywhere, giving the same advice to different people in different companies, and digging out the same pieces of vendor documentation again and again. And where we can, we've been advising on how to facilitate and shape the conversation to unblock it and get things moving.

So we wrote it down in this field guide. Download it, read it — give it to Claude to summarize and tell you your next actions to unblock your conversations.