A self-check
Should this organization start with AI?
An organization asks whether it should start with AI, and where. Everything is still ahead of them: the strategy, the first pilot, the first person in the building who has done this before. Leadership is curious and careful, the middle is split, and on the floor the same people carry both the fear and the hope.
It is the question I am asked most. The honest answer starts with the work, and the tool comes last.
The five questions below are about your organization. They are the ones I would ask in the first meeting, before anyone names a tool. Answer them and you get an honest read on where you stand, and on the hard part you are most likely to walk past.
Five questions · nothing leaves the page
Answer for an organization you know. Yours, ideally. Keep the AI idea that brought you here in mind, because the five questions circle everything around it. Two minutes, and the read at the end is honest.
Your self-check · where to start, and what to watch
What this argues
Every one of those five questions was about the people and the structures around a tool, and whether they are ready for it to change anything. That is the real subject. The technology is the last line of it.
The pattern under all of them is one I keep meeting. A new system arrives, and the parts that are easy to put in a plan get done: the budget, the license, the launch date. The part that decides whether anyone works differently afterwards, the people whose job it changes, is left for a phase that never quite arrives.
So the check gives you a position instead of a verdict: where you actually stand, and which of the hard parts you are about to walk past. The first real step is the few days you spend finding out what the work actually is.
A note on honesty
Five questions see only the outline of your organization. What is real is the questions themselves, the ones I would ask before any talk of tools. If most of your answers sat on the first option, you already knew to wait. What you needed was someone to ask.