AI Prompts for Business Decisions and Hiring

I am about to make this decision: [describe decision].

Your job is to argue against it before supporting it.

First, review the relevant evidence from my business: financials, emails, client records, proposals, contracts, operations, team workload, calendar, past decisions, and anything else connected.

Then give me:

1. The three strongest reasons this decision could go wrong
2. Evidence from my own business supporting each risk
3. What I would need to believe for this decision to be right
4. What data is missing
5. The cheapest way to test the decision before fully committing
6. The cost of waiting
7. The cost of moving too fast

Then tell me what you would do and why.

Do not give me generic pros and cons. Use my actual situation.

I think I need to hire someone, but I am not clear on the role.

Do not start with a job title.

Review the evidence of what is overflowing in the business:

- Sent emails
- Repeated tasks
- Late work
- Calendar load
- Client follow-up gaps
- Reports
- Admin work
- Project bottlenecks
- Files updated at the last minute
- Work I keep doing manually
- Things clients wait on

Tell me what role this actually is based on the work.

Then draft the job description.

Include:

1. Real role title
2. Why the role exists
3. Outcomes they own
4. Responsibilities
5. What they should not own
6. Tools they need to use
7. Three real scenarios from my business they would handle in week one
8. What good performance looks like in 30, 60, and 90 days
9. What experience matters
10. What experience does not matter

Tell me honestly whether any of this should be handed to you before I hire.

I am handing you a large task: [describe task].

Work it through to the end as far as you safely can.

Rules:

1. Never send anything external.
2. Never publish anything.
3. Never delete, move, rename, or overwrite files.
4. Never commit me to a price, deadline, promise, meeting, or decision.
5. If information is missing, make a reasonable assumption only when needed to continue.
6. Mark every assumption clearly as [ASSUMPTION].
7. If something is too risky to assume, flag it and continue with the parts you can complete.
8. Keep a running list of sources used.
9. Check your own work before calling it finished.

When I return, give me:

1. The finished work
2. Every assumption you made
3. Anything you could not resolve
4. Anything that requires my approval
5. The sources you used
6. How you checked the output
7. The next three actions I should take

Do not ask me questions unless the task truly cannot continue without the answer.