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Happy Tuesday,
This is the written version of today’s podcast episode. If you’d rather listen, it’s on Spotify and Apple Podcasts.
Next week... I'm closing out the Startup People Summit hosted by none other than Matt McFarlane.
The program is 🤯, and I'll wake up a bit (too) early so I don't miss anything.
My talk will center around that you can just...do things now. Build things.
And how you do them. And why you need to do them.
And why you shouldn't do pilots.
See you there? —>
And on Friday this week, I’ll do an update on the latest in the world of AI from a leadership perspective. What do you need to know? What’s the latest updates?
100% free and you only need to be subscribed to this very newsletter.
(Which I hope you are!)
In May, I wrote that AI is a work tool, not a perk. The argument was simple. If you buy Copilot, give everyone the full license, because the alternative is building an A-team and a B-team inside your organization.
Three months and a lot of client work later, I want to come back to it. Not because I’ve changed my mind, but because I expected (hoped?) to see the gap start to close by now. I don’t see that. What I see is organizations fuelling it.
Nobody is doing this out of malice
I don’t think this is done out of “evil”; there is no bad intent anywhere in the chain. Nobody sat in a meeting and decided who should be allowed to pull ahead. (I sincerely hope this at least) Instead, it’s a budget line, a pilot that never ended, a license count that made sense in October 2025. Good people, sensible decisions, and an A-team and a B-team at the end of it.
And I get it. We’ve always had fast adopters. People who are extra curious, extra invested, who want to learn new things, whether that’s to have an easier day at work or to stay ahead. That part isn’t new and isn’t a problem.
The problem is what the organization does with that difference, and right now, most of them are widening it rather than closing it.
Enter almost any organization, and you can sometimes visibly see or at least feel both groups from the same spot. One group is far ahead; they’re running fast, they have superpowers, and they either pay for their own Claude and ChatGPT accounts or they’ve nagged their employer into giving them a proper license.
The other group has barely started, or they’ve tried it once or twice but haven't found lasting results for various reasons.
Same company, same floor, sometimes the same team, yet so different results or thoughts.
So how do we end up here?
Someone knocks on the door and asks for a business license. They get it, because they asked and because they clearly know what they want it for. The person who didn’t knock doesn’t get one. Nobody made a decision about who pulls ahead. The distribution follows who was comfortable asking.
If you call yourself an equal opportunity employer, that has to include the tools. Not only for the ones who are loud and vocal about wanting a paid license. You roll it out universally, or you’re letting confidence decide who gets to be productive.
When I look at the organizations where this has gone sideways, the common denominator isn’t budget. It’s that nobody defined why this matters.
Why do we care about AI? Why is this an investment we need to make? Because it is an investment, a conscious one, and it has two halves. The tooling is the easy half. The other half is helping every person answer the question “what does this mean for me and my job on Monday morning?”
Without that second half, you’ve bought licenses and called it a transformation. (yey!)
You can’t be strategic if you can’t be practical
And before we talk about this, please keep my sample in mind. My sample is organizations that want to work with AI in this shape and form. The organizations I work with lean forward by definition, so don’t draw too many conclusions from what I see.
But what I will say is that the ones doing this well share one trait. Leadership has a working understanding of what AI can and cannot do. Not a vendor deck; hands-on with the tools. (If you’ve been reading this newsletter since the dawn of time, this is hardly a surprise, but I will keep repeating this until we have all lead teams onboard. Current estimate is May 2057.)
But yes, that’s my firm belief after many (many) lead team sessions this year. If you can’t be practical, you can’t be strategic. Without a basic, rudimentary grasp of how the thing works, it’s close to impossible to get any of this moving.
And the pace right now is punishing. It’s been fast since ChatGPT launched, but the last six months are something else. Every month you leave the B-team where it is, the distance grows.
The fix hasn’t changed since May. Give everyone the full tool, train everyone, and tell people why. What has changed is how much catching up your B-team has to do once you finally decide to.