By Miles Pearson · 18 October 2026 · 5 min read
Most leadership teams I speak to have already tried AI in some form. A licence was bought, a pilot was run, a few people found it useful, and then the momentum faded. Nobody can quite say what the business gained, and the next AI proposal is met with polite scepticism.
That pattern is not a sign that AI does not work. It is the predictable result of treating AI as a product to install rather than a capability to build.
The shortcut that looks like progress
The shortcut usually starts with a tool. Someone sees an impressive demonstration, a subscription follows, and the organisation is asked to find uses for it. The question being answered is 'what can this tool do?' when the question that matters is 'where is our business losing time, money or quality, and could AI help there?'
Starting from the tool feels fast, and it produces visible activity. It rarely produces measurable value, because the work it touches was never chosen for its importance.
Three reasons shortcuts disappoint
- No clear problem. Without a defined business outcome, there is nothing to measure success against, so success is never declared.
- No change to the workflow. AI added on top of an unchanged process often creates extra steps rather than removing them.
- No ownership. When AI belongs to everyone in general, it belongs to no one in particular, and it drifts.
A better first move
Begin with the work, not the technology. Identify two or three processes where delay, rework or manual effort is costing the business something you can name. Agree what 'better' would look like in numbers, and who owns the result.
Only then ask which tools fit. Often the answer is simpler and cheaper than the original pilot, because it is aimed at a specific job rather than a general aspiration.
This is the core idea behind Chess Not Checkers: strategic advantage comes from thinking several moves ahead, not from reacting to whatever is newest. If you would like the full argument, you can request the complete guide below, or book a call to talk through where AI could make a measurable difference in your organisation.