Updated 20 September 2026: first published on Elite Agent in May 2025. The article has been refreshed as an AI basics guide to writing clear advertising hooks from a factual brief.
One of my early ChatGPT experiments involved asking Don Draper, the fictional advertising executive from Mad Men, to write an opening hook.
It was a fun way to get started. Watching the show, I could imagine him enjoying a listing campaign, although he didn’t always seem to spend much time working while he was at work.
A famous name can suggest a creative direction. The useful improvement is giving AI a clearer account of what you are advertising, who needs to understand it and which facts you can support.
How do I get AI to write a better opening line?
Here was the original experiment:
Could you please act as a copywriting expert - for example - Don Draper - and write me an opening hook that will stop the scroll?That historical prompt gives the tool a role and a task. But it leaves out the property or service, the reader and the evidence. A model can fill those gaps with polished language that says very little.
For your first exercise, choose one advertisement. Write down the actual features, the reader’s practical question, the platform and what you want someone to do next.
Add a short example of your own writing if you want the result to sound like you. Leave out private client information and use only property details you have checked.
Try a brief with three different angles
Help me draft opening hooks for one real estate advertisement.
Property or service: [DETAILS]
Reader and what they need to know: [DETAILS]
Verified features or evidence: [FACTS]
Platform and length: [DETAILS]
My voice: [DESCRIPTION OR SHORT EXAMPLE OF MY WRITING]
Next step for the reader: [ACTION]
Ask up to three questions if important information is missing, then wait for my answers.
Write three distinct hooks: one led by a specific benefit, one by a useful question and one by a concrete detail. Use my voice. Do not copy a slogan or present the result as the work of a famous advertising person.
Do not invent features, prices, scarcity, demand or results. Avoid generic superlatives and flag claims that need evidence.
Explain the angle of each hook in one sentence. Suggest one to test based on its fit with this brief. Do not predict performance without results.Compare the ideas against the facts
Imagine a fictional property with a covered outdoor area, confirmed in your fact sheet. One opening might lead with the feature itself. Another might explain how that space connects with the living room, if the layout supports it.
“Entertain outdoors in every season” goes further. Does the space really support that promise? The attractive sentence still needs to survive a factual check.
Likewise, “everyone is looking for a home like this” is a demand claim, even if the AI treats it as harmless advertising language. Replace it with something specific you can show.
Test one opening, then learn from the response
Read the three hooks with the rest of the advertisement. The opening should lead naturally to useful information and a clear next step. It should also make sense on the platform where it will appear.
Ask a colleague which property detail they remember after reading it. If the answer is only “it sounds impressive”, your brief may need a stronger concrete detail.
Compare the early Don Draper prompt with the fuller brief using the same task. Look for relevance, accuracy and your own voice. Longer is not automatically better; the extra information has to help.
When you use a hook, record where it ran and what happened. Treat enquiries and other responses as evidence to learn from, rather than proof that a chatbot has found a winning formula.
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.