Prompt · Role Prompting · Advanced

Pipeline of Roles: Stress-Test a Listing Agreement Before You Sign

Build it. Attack it. Argue back. Then decide.

This version adds the agent’s side and a test of your own risk ratings. You finish with one page of must-change terms and questions for an attorney.

About This Prompt

Author: Adam Bloom
AI Technique: Role Prompting
Level: Advanced
Best For: Small property owners · Stress-testing a listing agreement
Last Updated: 2026-11-14
Last Reviewed: 2026-11-14

Pipeline of Roles Prompt Template

Work in seven steps, one role at a time. Context I’m giving you: – Property: [PROPERTY TYPE AND LOCATION] – Goal: [MY GOAL AND TIMELINE] – What worries me: [MY WORRIES] – My priorities, ranked: [MY PRIORITIES] Step 1, Builder: explain my listing agreement in plain words. Cover the term, the fee, the exit options and any follow-on period. Define legal jargon. Step 2, Adversary: list the 12 terms most likely to trap or cost me, ranked as my top risks. Name the clause for each. Rate each low, medium or high, with one reason and a worst-case cost. Step 3, Advisor: turn those into questions to ask my agent, most important first. Add what I should push to change, and a fallback if the agent refuses. Step 4, Builder: argue the other side. For each of the top five risks, give the agent’s likely reason for the term and when it is fair. Step 5, Advisor: revise your questions in light of Step 4. Drop any that Step 4 answers well. Step 6, Adversary: say what would change your mind. For each top risk, name the fact or clause that would lower its rating. Step 7, Advisor: give a final one-page list: must-change terms, nice-to-have changes, questions for a licensed attorney. Rules: – Quote the clause behind every claim. – Flag anything you can’t support from the text, and mark any guess. – If the agreement is silent on a topic, say so rather than assume. – Don’t give legal conclusions. Agreement: [PASTE AGREEMENT]

Free to use. Copy it, change it, share it. No credit needed.

What to Fill In

[PROPERTY TYPE AND LOCATION]: what you are selling and where. Example: “Small rental duplex, mid-size city.”
[MY GOAL AND TIMELINE]: what you want from the sale and by when. Example: “Sell in about six months.”
[MY WORRIES]: what you fear most. Example: “A long lock-in, and fees if I find my own buyer.”
[MY PRIORITIES]: what matters most, in order. Example: “1. A fast sale. 2. Low fees. 3. Freedom to find my own buyer.”
[PASTE AGREEMENT]: the full text of the agreement. Remove names, addresses and ID numbers first.

Example: A Seven-Step Pipeline of Roles Prompt on a Listing Agreement

Illustrative example, not a client result

Input: A small duplex owner wants to sell in about six months. The draft agreement sets a 6% commission, a 12-month term and a 180-day follow-on period. All figures and clause numbers are invented.

Context lines as sent (Steps 1 to 7 and the rules are unchanged from the template):

Context I’m giving you: – Property: Small rental duplex, mid-size city – Goal: Sell in about six months – What worries me: A long lock-in, and fees if I find my own buyer – My priorities, ranked: 1. A fast sale. 2. Low fees. 3. Freedom to find my own buyer. Agreement: (full text of the draft agreement pasted here)

Output (shortened to the top 2 risks):

Step 1, Builder: The agent sells your duplex over 12 months for 6%. A fee also applies for 180 days after the term ends. You have no stated way to exit early.
Step 2, Adversary: (1) Clause 7, Protection Period: high. Worst case, you owe 6% on a buyer you meet after the term ends. (2) Clause 3, Term: high. Worst case, 12 months locked in with no cancellation right.
Step 3, Advisor: (1) Can I cancel if the marketing isn’t done? Push for a 30-day cancellation right (guess). Fallback: a shorter term. (2) Who counts as the agent’s buyer during the 180 days? Push for a named-buyer list.
Step 4, Builder: The agent’s likely reason for Clause 7 is to stop owners dodging the fee by closing with a buyer the agent found. That is fair if it covers only named buyers.
Step 5, Advisor: No questions dropped. The Clause 7 question now asks for a named-buyer list instead of a shorter period.
Step 6, Adversary: Clause 7 drops to medium if the fee covers only named buyers. Clause 3 drops to medium if a 30-day cancellation right is added.
Step 7, Advisor: Must change: Clause 7 and Clause 3. Nice to have: a lower rate than 6%. For an attorney: how the fee applies if I find my own buyer.

Flag: The 6%, 12-month, 180-day and 30-day figures, and all clause numbers, are invented. Check your own agreement for the real terms.

Why the Pipeline of Roles Prompt Works

The agent’s side shows why a term exists and when it is fair. Testing your own ratings shows which risks hold up. The final list separates must-change terms from nice-to-haves.

When the Pipeline of Roles Prompt Doesn’t Work

This is not legal advice. Have a licensed attorney or your local regulator review anything you sign.
The AI may argue the agent’s side weakly, or lower a rating at the first pushback. Read Steps 4 and 6 with that in mind.
The three roles are one AI, so it can still agree with itself.
Seven steps in one chat is long. If a step is skipped, ask for it by number.
Rules differ by place. Say where you are in your property line.

Research Behind This Prompt

Kim et al. (2024), DEBATE: Devil’s Advocate-Based Assessment and Text Evaluation. Supports. A critic told to attack the other agents’ answers beat a standard baseline in text-evaluation tests. Gains levelled off after about four rounds.
(2024), Debating with More Persuasive LLMs Leads to More Truthful Answers. Mixed. Debate recovered the most performance of the setups tested. Models often conceded their assigned side, even when told not to.
(2025), Measuring and Mitigating Identity Bias in Multi-Agent Debate via Anonymization. Challenges. Agents deferred to a peer’s answer far more often than they stuck to their own.

What the Evidence Says

Mixed. A critic role helped in text-evaluation tests, but models often concede an assigned side or defer to a peer. None of these studies tested listing agreements. Use Steps 4 and 6 to find gaps, not to reach verdicts. Check each reason against the document.

Sources last checked 2026-11-14.

Pipeline of Roles FAQ

Why does the Builder argue the agent’s side in Step 4?

Terms usually exist for a reason. The agent’s likely reason shows which terms are fair and which are one-sided.

What does “say what would change your mind” do?

It names the fact or clause that would lower each rating. You can then ask your agent for exactly that.

Why does the Advisor appear three times?

Step 3 drafts the questions. Step 5 revises them after the agent’s side. Step 7 turns everything into one final list.

What if the AI skips a step?

Ask it to redo that step by number. Seven steps in one chat is long, so a skipped step is common.

Can this replace a lawyer?

No. It helps you arrive with better questions. A licensed professional should still review the agreement.

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