The Real Estate Pro’s Guide to Supercharging ChatGPT
There are tens of thousands of AI tools on the market today, with hundreds of AI tools relevant to commercial real estate. Some are niche, others are general-purpose. But nearly all of us (whether brokers, investors, analysts, or operators) have used or actively use ChatGPT.
Why? Because it was the first (and change is hard!). ChatGPT introduced the world to generative AI in a way that was accessible, intuitive, and, frankly, mind-blowing.
Whether you’ve stuck with it or moved on to a competing LLM interface (like Claude, Gemini, or Grok), it’s still the one most of us know best.
That said, ChatGPT is constantly evolving. The interface changes regularly. New features appear overnight. What was once paid becomes free, and what was once free may become paid. Trying to write a comprehensive “guide” to ChatGPT is like mapping a road system that’s still under construction. It will be outdated the moment you hit publish.
So instead, we’ve decided to maintain a running list of Tips for Getting 2x More Out of ChatGPT, with a special focus on the audience we care most about: commercial real estate professionals.
This list will evolve as ChatGPT evolves. Bookmark it. Share it. Check back often.
And with that, here’s a list of tips you can start using today to get dramatically more out of ChatGPT:
Tips for Getting 2x More Out of ChatGPT
In no particular order, here are tips from the A.CRE team, which on average starts over 25 new ChatGPT conversations every day and has used the tool daily since December 2022.
1. Use the ‘Edit Prompt’ Button Often
When ChatGPT misses the mark, skip the follow-up corrections that bloat your context window. Instead, click the Edit Prompt button on your last input, refine it, and resend. This gives you a clean, fresh response without carrying forward confusion from earlier misfires.
2. Toggle Browsing—or Tell ChatGPT to “Browse the Web”
Don’t assume ChatGPT will fetch live data. Either switch on the browsing/search feature or include a directive like “browse the web for today’s yield on 10-year UST.”
3. Give It a Role
Want sharper output? Begin your prompt with “You are a CRE acquisitions manager,” “You are a leasing broker,” or “You are an underwriting analyst.” This primes ChatGPT to draw from the most relevant patterns in its training.
4 Use the Team or Enterprise Tier for Confidential Files
When handling sensitive information (e.g. property data, rent rolls, financial models, lease abstracts, etc), stick with Team or Enterprise plans. They offer enhanced privacy and protection for sensitive documents, unlike Free where uploads might be retained temporarily or used for training.
5. Max Out Custom Instructions
Use the full 3,000 characters to preload ChatGPT with everything you want it to know about you. Ask ChatGPT itself to draft these instructions but require it to be exceptionally concise (i.e. no wasted words). Ignore the labels (“What traits?” / “Anything else?”) and instead pack those boxes with the details about you and how you work that you want ChatGPT to know in every conversation.
6. Get GPT-5 to Reason without Toggling on ‘Thinking’ Mode
Asking ChatGPT to “Think hard” about a topic can nudge GPT-5 into its Thinking mode, which has usage limits and may consume credits.
7. Say “Please remember …” to Save Things to Memory
To add something to ChatGPT’s Memory, literally tell it “Please remember …” For example, “Please remember I focus on Sunbelt industrial, 14 to 16 percent levered IRR targets, and 10-year holds.” You can review and delete memories in Settings.
8. Define Success Upfront
Vague asks waste time. Instead of “Summarize this deal,” say: “Create a 1-page investment memo for this offering memorandum. Include purchase price, stabilized yield-on-cost, and three downside risks. Limit to 500 words.” Clear criteria make outputs useful.
9. Don’t Treat it Like Google! Give Directives, Not Questions
ChatGPT isn’t Google. Don’t ask, “What are good tenant retention ideas?” Assign a job: “Draft a 90-day tenant retention plan for a suburban office asset. Include outreach cadence, KPI targets, and one cost-effective incentive.”
10. Split Big Asks into Steps
A giant prompt produces noise. Break the job down:
- Step 1: “List 5 key risks for acquiring Class B industrial in Atlanta.”
- Step 2: “Turn those risks into lender Q&A bullets for IC.”
- Step 3: “Write a 1-paragraph mitigation plan for each risk.”
Each step builds cleanly on the last.
11. Iterate Like a Real Conversation
Treat ChatGPT like a junior analyst. First: “List 5 angles for a thought-leadership post on AI in CRE underwriting.” Then critique, pick one, and ask for title options, then an outline. Iteration beats one-shot prompts every time.
12. Show Great Examples
Don’t just tell ChatGPT what you want but show it. Paste a sample of an IC memo, quarterly report, or investor letter that reflects your tone, density, and structure, and optionally include one anti-example to avoid.
13. Fix grammar without rewrites
For quick polish, use: “Fix grammar without changing wording.” If you want visibility into the edits, add “bold the changes” so you can scan adjustments instantly.
14. Ask for sources with links
Require citations with live URLs, then actually click through and spot-check the claim. Tell ChatGPT which sources you prefer, for example primary data, statutes, filings, broker research.
15. Tell it what to do, not what not to do
Skip negatives like “don’t be generic.” Specify the deliverable, structure, tone, and constraints, for example “250-word IC risk section with one cited data point and a clear recommendation.”
16. Verify when it sounds confident
If a response reads too certain, ask “Is that actually correct?” and force it to surface assumptions and sources. Then verify against your authority of record, for example code sections, assessor pages, lender term sheets, or the OM.
17. Start fresh when it stalls
If quality slides, looping appears, or the thread gets noisy, open a new chat. Paste a three-line recap of objective, role, and constraints, then re-issue the request.
18. Use Projects When…
You need to organize everything related to one initiative and want a consistent output for that initiative, but don’t need to share it with others. For instance, a Project for IC prep, another for deal underwriting, a third for research, etc. Projects include unique instructions and files while keeping related chats tied together, so you get consistent output and shared memory across that project.
19. Use Custom GPTs When…
You want ChatGPT to behave consistently and want to share that with others. For example, build a “CRE Lease Abstractor” GPT that always extracts key terms from uploaded leases, or a “Debt Sizing GPT” that applies your firm’s leverage rules. Share that with an analyst to use to abstract leases consistently.
20. Use Deep Research to Start a Conversation
Instead of diving straight into a chat, first run Deep Research so ChatGPT pulls in facts, data, and perspectives from across the internet on your chosen topic. Once it lays out the sourced foundation, you can have a far richer back-and-forth—asking questions, challenging assumptions, or exploring scenarios. The research fuels the conversation, making it more accurate and productive.
21. Paste Screenshots to Chat About Your Work
Use screenshots for fast, visual context. Hit Win+Shift+S in Windows to snip what’s on your screen, then paste it directly into ChatGPT with CTRL+V.
22. Use Voice Mode to Brainstorm on the Go
When you’re away from your desk, fire up Voice Mode in the ChatGPT mobile app to capture ideas as they come. Talking through thoughts can spark faster, freer brainstorming than typing.
23. Dictate the First Prompt in a Conversation
Instead of typing out a long setup, use voice dictation to speak your opening prompt. This makes it faster to frame context, objectives, and constraints in one shot.
24. Turn Off Canvas
Personal preference, but in our experience, Canvas just adds friction. Disable it and stick to iteratively editing drafts in the chat interface.
25. Regularly Review and Clean Up Memories
ChatGPT memory fills up fast, and once it’s packed with outdated details, the quality of responses drops. Make it a habit to open the memory manager, scan what’s stored, and delete anything no longer accurate or useful. A lean, up-to-date memory ensures ChatGPT works off the right context instead of recycling stale information.
26. Branch Into a New Chat to Explore Angles
Use the Branch in new chat option when you want to chase an idea without derailing your main thread. This feature spins up a fresh conversation that inherits all context up to the split point, letting you explore a side angle while preserving the original flow. It’s especially powerful for brainstorming or testing scenarios, and even better when paired with Projects to keep related threads organized.
27. Selectively Edit Images with the Selection Tool
When working with ChatGPT’s image generation, you don’t need to regenerate the entire picture to make a tweak. Click the image, choose the Selection tool in the top-right, highlight the area you want to adjust, and then prompt for the edit. This lets you refine specific sections without impacting other areas of the image.
