Most people decide what to paste into an assistant by instinct, in the moment, while trying to get something done. That is how material ends up somewhere it should not be — not through a decision, but through not quite making one.
Here is a checklist worth running first. It takes a minute, and it is designed to be used rather than admired.
One: is this mine to share?
Not do I have it. Do I have the right to give it to somebody else.
Material that arrived from a client, a customer, a patient, an employer or a counterparty is usually held for a purpose. If you would hesitate to forward it to a stranger by email, pasting it into a hosted service deserves the same hesitation, because it is the same act with better branding.
Two: is anyone identifiable?
Names are the obvious case, and the least of it. People are identifiable from an address, a date combined with a place, a job title in a small organisation, or a set of circumstances that is unusual enough.
A useful test: if this appeared in a newspaper with the names removed, would the person still know it was them? Would their neighbour?
Three: what happens to it after I press send?
Worth actually finding out rather than assuming, and the answer differs by service and by plan on the same service.
- Is it retained, and for how long?
- Is it used to improve the provider's model?
- Can a human at the provider read it?
- Can you require deletion, and get confirmation?
A free consumer tier and a paid business tier of the same product often answer these differently. People routinely assume the business answer while using the consumer one.
Four: would I be comfortable explaining this later?
The most practical question in the list, because it sidesteps the technicalities.
Imagine telling the person the material concerns exactly what you did with it. Not defending it — just describing it plainly. If that sentence is uncomfortable to say, the discomfort is information, and it usually arrives before the technical analysis does.
Five: is there a version of this that does not need the material?
Often there is, and it is quicker than the alternatives.
You rarely need to paste the whole document. You can frequently ask the general question — how such an arrangement usually works, what such a clause typically means — and apply the answer yourself. You get most of the help and share none of the material.
This is the habit worth building. It is not a compromise so much as a realisation that a lot of what people paste in was never doing any work.
Six: the one people skip
Is this going to become a habit?
A single considered exception is one thing. What actually happens is that the first exception makes the second easier, and within a month the assistant has seen a great deal of material nobody ever decided to share. The decision was made once, casually, and then inherited.
So the real question is not whether to paste this. It is whether you are comfortable with the pattern that starts if you do.
When the honest answer is no
For some material, running this list produces a clear no every time — and that is the point at which people either give up on AI for their real work, or change where the computer is.
If the material cannot leave, an assistant that reads it in your own building is not a workaround. It is the only arrangement in which the question stops being asked at all, because nothing is being shared with anybody.
Why some work cannot use public AI at all →
Personalisation without sending anything away →
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