ASK TOBY

Say when it should ask.

The words When to ask beside an agent window with a raised hand and a question box.

Tell each agent when to stop and ask: what it cannot decide, what it cannot undo, and what it cannot find. Write the rule down.

An agent needs a stop rule

An agent that never asks will guess. An agent that always asks will not get far. A short stop rule sits between the two. It says plainly when the agent should pause and put a question to a person.

Three reasons to stop

Keep the rule to three parts.

  • Cannot decide. The choice belongs to a person, or the brief does not cover it.
  • Cannot take back. The step leaves no easy way to reverse it.
  • Cannot find. The thing the job needs is missing, or two sources disagree.

Say where the question goes

Name one place for questions. The agent leaves its question there and moves on to work it can still do. You know where to look, and the agent is not left waiting on a reply in a chat.

Make the question easy to answer

Ask the agent to write each question so you can answer it cold. State what it was doing, what it needs from you and the options it sees, with its pick first. Then your answer can be one word. See the approval workflow.

Keep the limits list beside the stop rule

The stop rule works with the three lists from agent permissions. Anything on the Never touch list is a reason to stop and ask, not a reason to guess.

Show waiting questions in the daily report

Put every open question under the Waiting on you heading of your daily report. Then one page shows you what needs your answer.

Check it: a made up stop rule

  • Cannot decide: two headlines both fit, and the brief names no favorite.
  • Cannot take back: the step would replace a published page.
  • Cannot find: the source file is not where the job says it is.

Three reasons. One place. One easy question.

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Jeff Sperandeo. Video editor. I ran the paid ads side and the organic side of a big YouTube channel at a Fortune 500 company. I saw how ads and AI find people from the inside. Now I build agents on my own machines, and I show you how.