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Phil Holland / Blog

Give AI a Checklist Before You Give It a Job

By Phil Holland ·

AI can produce a polished answer before we have finished explaining the problem. That is useful when we need a starting point. It is also a good reason to slow down before treating the answer as a finished job.

When I ask an assistant to help with production work, I want to be clear about the assignment, the boundaries, and how we will know the result is right. A short checklist gives both of us something better to work from than “handle this for me.”

Name the result you actually need

“Help with Sunday” could mean a rehearsal checklist, a volunteer email, a repair list, or a service rundown. Those are different jobs with different consequences. Start with one deliverable and say who will use it.

For example: “Turn these equipment notes into a repair list for our technical team. Keep each issue separate. Include the symptom, the affected area, and the next question we need answered.” That is specific enough to review without requiring a huge prompt.

Give facts a place to stand

Tell the assistant which source should settle a disagreement. A current calendar entry, the actual request, and a manufacturer’s manual are more useful than a confident guess. If the sources disagree, ask it to show the conflict rather than silently choosing one.

Keep observations separate from conclusions. “The screen was black during the opening song” is an observation. “The converter is bad” is a diagnosis that still needs evidence. An assistant organizing your notes should preserve that distinction, even if a tidy diagnosis would make the report sound more complete.

Define what it must leave alone

Preparing a draft and sending it are separate actions. So are suggesting a task and assigning it to a volunteer. Say which actions are authorized and which require a person to decide. Do not assume a tool connection means every possible action is appropriate.

Use only information you are allowed to share with the service you are using. A troubleshooting exercise rarely needs someone’s private phone number, a password, or a complete staff conversation. Remove those details before supplying an example, and follow your organization’s rules.

Ask for evidence of completion

An answer that says “done” should be easy to check. For a document, open the saved document. For a proposed checklist, walk through the steps. For a task entered in another system, confirm the actual task exists with the right details. A plan to do something is useful, but it should be labeled as a plan.

I also want an assistant to be comfortable saying what it could not verify. That gives me a real decision to make. A hidden gap becomes somebody else’s surprise later.

A small prompt you can reuse

Goal: Prepare a repair list from the notes below.
Source: Use these notes only; flag missing details.
Boundaries: Do not contact anyone or change tasks.
Format: One issue per item, with symptom and next step.
Check: Separate confirmed facts from assumptions.
Finish: Tell me what still needs human verification.

Try it on something small

Choose one low-risk job this week: organizing non-sensitive notes, outlining a training session, or drafting a checklist. Decide what a good result looks like before you ask. Then compare the output with your source, not just with how professional it sounds.

The goal is to save attention for people and decisions that need us. Clear instructions and a quick verification step make that a much more realistic goal.