Talk&Tinker

notes · October 2026

The questions nobody wanted to answer.

A while back I ran IT and security for a healthcare company. About ninety people. Three of us on the team, doing the work you’d normally hire ten or fifteen for.

Every time we signed a new customer, a spreadsheet showed up. Security questions. How do you protect data, who can log in, what happens if a laptop gets stolen. Row after row.

Here’s the thing: we’d answered nearly all of them before. Last month. For the last customer. The answers were sitting in old spreadsheets, policies, and somebody’s memory. So every new one meant digging, copying, and rewording. A full questionnaire took three to five days.

Nobody wanted that job. Everybody had to do it.

What we did

We gathered everything we’d already written down: a couple dozen finished questionnaires and a few hundred past questions and answers. Then we gave it to an AI assistant that could read all of it. A new questionnaire comes in, the assistant drafts every answer from what we’d already said, and a person reads it and signs off.

I was the one filling these out, so I saw the change firsthand. About nine in ten questions answered themselves. Of the rest, about half the time the assistant’s suggestion was already right, and the other half needed a tweak or a correction from me.

Three to five days became a few hours of review. Nobody timed it with a stopwatch, but I felt every one of those days come back. And the hours that were left were the part that should stay human anyway: reading it over and signing off.

Why a café should care

You probably don’t get security questionnaires. But you almost certainly answer the same questions over and over. The catering inquiry: do you do gluten-free, what’s the minimum, can you deliver to the beach. The contractor’s insurance-certificate request. The salon’s “how long does a balayage take and what does it cost.”

The answers already exist. You’ve already typed them, in old emails, in texts, on a laminated sheet by the register. You don’t have to sit down and write them all out again. We can pull them from what you’ve already sent, gather them in one place, and let something draft the next reply so you only have to read it and hit send.

That’s the whole pattern: if you’ve answered it twice, you shouldn’t have to type it a third time.