Updated 20 September 2026: first published on Elite Agent in April 2025. The article has been refreshed as an AI basics guide to exploring a decision with Six Thinking Hats.
Before real estate, proposals were my world: multi-million dollar proposals, mostly in technology. It was a good grounding in sales and writing.
One technique we used was to ask several executives to review a proposal from different perspectives. Giving each person a different “hat” helped the bid team notice questions we had overlooked.
You can use an AI chat to organise a similar exercise. It can suggest angles to investigate, but those are simulated perspectives. It does not tell you what a client or colleague actually thinks.
For a beginner, choose one bounded question: “What should we establish before deciding whether to take on this challenging listing?”
What are the Six Thinking Hats?
Edward de Bono’s Six Thinking Hats separates a discussion into different kinds of thinking. Here is a brief guide:
- White: the information you have and the facts you still need.
- Red: feelings and intuitions, expressed by the people who hold them.
- Black: difficulties, risks and reasons an idea may not work.
- Yellow: potential benefits and the reasons they may be achievable.
- Green: alternative ideas and approaches.
- Blue: the process, including what to consider next.
Original illustration: Claude.
The framework gives your conversation structure. It does not remove your biases or the model’s tendency to agree with the way you frame a question.
How can I use AI to examine a listing decision?
Describe the decision and the options. Provide checked information about the property, your team’s capacity, the seller’s stated expectations and the information still missing. Use an anonymised scenario and keep confidential documents out of tools not approved for them.
For the White Hat, you might need comparable sales and confirmed campaign costs. For the Red Hat, ask your colleagues and the seller about their concerns. An AI cannot supply their actual feelings.
Help me structure a real estate decision using Edward de Bono’s Six Thinking Hats.
Decision to consider: [QUESTION]
Options: [OPTIONS]
Checked facts, dates and sources: [INFORMATION]
Constraints and decision deadline: [DETAILS]
Known gaps: [GAPS]
Start by checking whether the question and options are clear. Then work through one hat at a time and wait for my response.
White: separate supplied facts from assumptions and missing evidence.
Red: ask what I feel and suggest questions for the people involved; do not invent their feelings.
Black: identify possible risks and the evidence needed to assess them.
Yellow: identify possible benefits and the conditions they depend on.
Green: suggest alternatives within the constraints.
Blue: summarise open questions, who should answer them and the next review step.
Do not invent property facts, costs, laws or likely sale results. Challenge my preferred option and explain what evidence could change the assessment. End with a decision checklist for human review, not an instruction to proceed.Check what the different hats reveal
For a fictional challenging listing, a Black Hat concern might be whether the team can deliver the proposed campaign alongside existing commitments. A Yellow Hat possibility might be gaining experience with a different property type. Neither is established merely because the AI lists it.
The next useful question is what would support or weaken each point. Check the workload with the people doing it. Discuss expectations directly with the seller. Investigate the property facts rather than letting an attractive scenario stand in for evidence.
A Green Hat alternative might be changing the campaign timing or narrowing the service you can offer. That suggestion still needs to fit the client’s needs and your actual commitments.
Turn the discussion into a next step
Ask for a short summary of what is known, what remains uncertain and who will check it. Keep that record with the decision date so you can see why you reached your conclusion.
If the model agrees too readily, ask it what you may be overlooking and which assumption carries the most weight. Then take those questions to a real colleague.
The value is in preparing a more thoughtful discussion. The decision, and the responsibility for it, remain with the people involved.
The original version appeared in Samantha McLean’s AI Powered Agents newsletter. Read the refreshed source article on AI Powered Real Estate by Samantha McLean on Substack.