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·6 min read·Adam Roozen

The carry

On AI pilots, AI strategies, and the results nobody can keep alive

Most AI pilots start the same way. There's a defined scope, a bounded budget, a specific technology, and a time horizon. Inside that fence, a pilot can look great. It can produce impressive demo results. Then it leaves the fence. It meets live systems, actual users doing things nobody planned for, data that shows up messy or late, cases that were never in scope, and the slow organizational work of getting people to change how their week goes. Often the pilot doesn't survive that contact.

Let's look at how that seems to happen, and then take it somewhere that isn't AI.

The carry

"The carry is the distance between a result that impresses people and a result someone is allowed to keep alive."

I think the useful word in there is allowed. Not able. Allowed. A pilot can genuinely work and still have nowhere to go. The tight scope, the small budget, the single technology, the clock - those are what make the test possible to run at all. They're also what keep the result contained. When the window closes, the structure that held the pilot closes with it, and nothing in that structure was built to hold what comes next. I don't think anyone designs it that way on purpose.

The pilot

Maya runs pilots for a living. Let's put her inside one and walk through the steps.

(a) She picks a specific technology.
(b) She draws the scope tight enough that the thing can actually be tried.
(c) She holds the budget to a fixed number.
(d) She sets a time horizon, so everyone knows when the window closes.

Then the demo lands. Maybe the room goes quiet in the good way. Maybe someone says the sentence that should make you a little nervous: this basically works.

Does it? Sort of. It worked inside the fence. Outside the fence it hasn't met anything yet. Actual users type things nobody planned for. Real data arrives late, or messy, or in a shape the pilot never had to accept. Edge cases show up in production in ways the pilot scope didn't include. And then there's the change-management part, where someone's ordinary week gets rearranged: training, new steps, a person who liked the old way. That part doesn't demo at all. It just takes months.

Here is where I think it usually breaks. Maya's results are real. But Maya doesn't hold next year's budget, and the people who do weren't in the room. This is the orphaned pilot: results that work, owned by nobody with the authority or the budget to operationalize them. One reason it hides for a while, I think, is that the demo genuinely was good. When people see a working result, they relax a little, and the question of who carries it starts to feel smaller than it is. Maybe most pilots die this way - not on the technology, on a handoff that never happens. There usually isn't a dramatic postmortem. The review meeting goes fine, everyone agrees it was promising, and then the calendar fills with other things.

The flip side is simple. Pilots seem to succeed when someone owns them and has a mandate to scale them. Ownership here isn't a name on a slide. It means somebody can keep spending after the demo is over, can sit through the follow-up meetings, can say yes to making the thing part of the day job, and can put it in front of a budget that renews.

The strategy

A strategy sounds like the bigger thing, but I think it's mostly just more honest earlier. It requires a clear problem statement tied to a specific business outcome. Not "we should do AI" - reader's choice on the exact wording - but a problem pointed at a result somebody already cares about.

It also needs data infrastructure that can support production-scale deployment, which is a polite way of saying the plumbing has to work when you run the thing for real and not just for the demo. That piece is easy to nod at and hard to fund, probably because nothing about it claps. When it isn't funded, the working result has nothing to stand on. The gap lands on a data or engineering team that wasn't part of the pilot and wasn't budgeted to close it. The work still has to happen either way, so the schedule stretches.

Then two more pieces:

(a) organizational ownership
(b) a sequencing plan

As far as I can tell, that's the practical difference. A pilot asks whether the thing works. A strategy asks what has to be true after it works. That second question is the carry. Most of what answers it doesn't demo well, so it tends to get skipped. A sequencing plan, once you strip the word down, is just admitting that some things have to exist before other things can, and writing the order down where people can see it.

Pulling the pattern out

Alright. Let's back away from the servers. We're hunting the carry.

A school tries a new reading block in one grade, with one excited teacher and a small grant. Scores move. Parents notice. Then the term ends, the grant ends, and next year's timetable belongs to a committee that was never in the classroom. The teacher can't set the schedule and the grant can't renew itself, so the result stops even though it worked.

Or a city paints a bike lane on a few streets and calls it a pilot. Riders show up. But the traffic lights are still timed for cars, the road-maintenance money lives in a different department, and the person who ran the paint can't approve anything permanent. When the pilot window closes there is no next decision attached to the result, so the lane stays temporary.

Closer in: someone changes how they eat for a month. Defined scope. Bounded budget, tbh. Specific technology - maybe just a grocery list. Time horizon. It works, which might be the sneaky part. Then travel shows up, a birthday happens, one bad Tuesday undoes the rhythm, and if nobody owns the scaled version - a plan for ordinary weeks, not just the sprint - the result was real and it still doesn't stick.

The pattern is not "pilots are bad." I don't buy that. Pilots seem to be how you find something out without lying to yourself too early. What decides whether the win survives? Not quality. Permission. A bounded win needs a carrier with a mandate, and the unanswered question is plain: who is allowed to carry the result past the fence, and has anyone actually handed them that permission yet?

The unresolved bit

I keep circling ownership - not as a job title, but as permission that outlives the demo. Who is allowed to keep a good result alive after it stops being cute? I don't always know. (I've probably been Maya at least once. Always practicing.)

Written by

Adam Roozen

Strategic Advisor. AI Strategy, Digital Commerce, Technology Transformation

Nearly 30 years of operating experience · Walmart · Sam's Club · Echidna

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