We Started in the Middle, and It Cost Us Months

We started in the middle of the org, on the sales team, because that is where the appetite was and because sales is the one place where nobody has to justify the project. You say the word “pipeline” and everyone nods. So that is where we went first, and I want to be clear that the work was good. We built real things. People used them. If you had asked me at the time whether it was going well I would have said yes, and I would have believed it.

What I could not have told you is why it wasn't spreading.

It stayed inside the sales team like water in a bucket. Nothing leaked sideways into marketing, nothing climbed. The senior team was aware of it in the way you are aware of a project happening two floors down, which is to say they could have described it in a sentence and would not have been able to tell you what it changed. And the reason, which took me longer to see than I would like, is that I had been treating this as a technology rollout. Pick a team, prove value, expand. That is how you install software. It is not how you change the way a company works, and this is a change in how a company works.

The turn came when I stopped trying to spread it outward and started working directly with the VP of sales, the VP of marketing, the COO and the CEO.

Not on prompts. Not on writing better emails, which is what most executives are doing with these tools and which is roughly equivalent to buying a car and using it to sit in the driveway and listen to the radio. We connected Claude to the things they actually live inside: their calendars, their email, their meeting transcripts. Then we gave it a persistent memory, so it remembered them week to week, and we called the whole arrangement a chief of staff, because that is what it turned out to be.

Here is what it does, and I want to warn you in advance that it is going to sound small.

It tells them what is going on. What did people commit to in Tuesday's leadership meeting. Who is waiting on me right now, and how long have they been waiting. What did I promise three weeks ago that has quietly fallen off the edge of my own memory. Who did I say I would follow up with, about what, and did I. It is not clever. It is bookkeeping. And it turned out to be the most powerful thing we built, because the thing senior people are starved for is not analysis, it is visibility. They are sitting on top of an organization they cannot see into, running on a memory that ends about four days back, and everyone below them assumes they know things they do not know.

Once they had that, the whole thing changed character. It stopped being an initiative that sales was doing and started being how the leadership team worked. And that is the moment adoption becomes somebody else's problem, in the best possible sense, because now the COO is in a meeting saying hang on, let me pull up what we actually said about this last month, and eleven people watch that happen, and no change management deck in the world is worth what those ten seconds are worth.

The other unlock, and this one still delights me, was design.

You have a senior person who has been asking for a dashboard for eight months. Or an annual report, or a one-pager for the board, or a piece of collateral for a customer, and it has not been built, not because anyone is lazy but because the person who would build it has forty other things and this keeps landing at number forty-one. The exec knows exactly what they want. They can see it. They just cannot make it, and they have spent their entire career translating what they can see into a brief for somebody else, losing about a third of it in the handoff every single time.

Now they describe it out loud and it exists.

Watching that happen to somebody who has never made a thing in their life is genuinely something. Their judgment was never the bottleneck. Their taste was never the bottleneck. The bottleneck was that they had no hands, and they had made peace with that so long ago that they had stopped noticing it was there. Give an executive hands and you do not have to sell them on any of this. They are already gone.

So the pattern, stated plainly, because I think it is the most useful thing I know right now:

This is not a piece of software you install somewhere and grow. It is a change in how people work, and changes in how people work do not travel upward through an organization. They never have. They flow down, from people who are visibly doing it themselves, or they do not flow at all. When the leadership team has not touched the thing, they cannot tell the difference between a real use and a demo, they cannot tell which risks are serious and which are vendor theater, and they cannot back it when it gets hard, because they have no instinct for it. What you get instead is exactly what I got at first: a good pocket of adoption, sealed shut, going nowhere.

The reason people hand this to the middle of the org is not stupidity. It is that senior calendars are the most defended real estate in any company, and asking a CEO to spend six weeks learning a new way to work is a genuinely expensive ask. I understand it. I just think it is the wrong trade, and I think the six weeks come out of your hide either way, later, in the form of a rollout that never quite takes.

If the answer makes them uncomfortable, you have found the thing.