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Before You Sign

Six questions to ask before you sign off on AI-assisted work, with a printable checklist

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What's Inside

→ Could I catch a wrong answer here without asking another AI? AI output reads clean and confident whether it's right or not.
→ What input would turn this check red? A pass is a statement about a specific set of conditions.
→ Who learns something from doing this work today, and where else would they learn it? The hard cases turn up while someone is working through the ordinary ones.
→ Where does the reasoning behind this workflow live, and is it written down? The exceptions, the approvals and the judgment calls won't show up in the data on their own.
→ Could the next person name the three decisions behind this without asking anyone? The ticket was written before the real decisions got made, and almost nobody goes back to update it.
→ Does this agent's permission expire, and can a named person shut it off? A good answer has a date and a name.

Why I wrote it

Most of the work that crosses my desk now has a model somewhere in it: a draft, some code, the first pass at a plan. It shows up looking finished, and nothing in the tone tells you where a person got unsure. Then I have to sign it, send it on, or leave an agent holding the access I gave it. The signature only means something if I can still see what’s wrong with the work.

Between September 2 and October 27, 2026 I wrote six essays about that moment. Each one came down to a single question I’d want answered before I sign, and the guide gives you all six with what a good answer and a weak answer sound like.

Who it’s for

It’s for people who sign off on work that goes to the board, a regulator or a customer, and for whoever decides whether to automate work or give an agent access. You don’t need to ask all six about everything. Ask them once per workflow. When a workflow’s answers hold up the first time, the next document through it needs much less of your attention.

The guide ends with a printable checklist in two groups: one for signing off on output (a report, a deck, a finished branch) and one for deciding to automate work or give an agent access. If a line stays blank, hold the signature until someone can fill it in from the work itself.

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About the Author

Written by Eric D. Brown, D.Sc., after 30 years of technology consulting, helping leadership teams decide what to trust before they sign off.

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