The Best CRE Prompts Are Built Around Workflows

By Drew McWilliams, Doug Banerjee & Lacey Willard | The New CRE Edge

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The structure you bring to the AI is what creates the value. Brokers use that structure to win and move deals. When you own the asset, the job changes. You are protecting the value of what you already hold, and you answer to the people whose capital is in it.

Here’s what that looks like in three of the moments where it matters most.

Worth saying before those three. Everything below runs inside a permissioned environment, on records we already hold. Investor data and fund materials do not go into public tools. The people whose capital is in these assets expect that standard, and it applies to the inputs the same way it applies to what reaches them.

Catching the Problem Three Months Before the Valuation Does | Drew McWilliams

Every month an operating statement lands on my desk that looks basically fine. Fine is the word that gets people in trouble. A property can sit right on budget at the top line while something underneath it is quietly going structural.

So I stopped reading statements and started interrogating them. I built a prompt that pulls the month against budget, the prior month, and the original underwriting, then forces a call on every variance that matters: temporary, or structural. Last quarter it caught a payroll and insurance creep on one asset that we wouldn’t have seen until refinance. We fixed it while it was still small. That stack includes the rent roll, which is one reason the whole workflow lives inside our own systems.

Advanced Prompt Example

You are a skeptical institutional asset manager. Review the attached current operating statement, rent roll, trailing budget, prior-month statement, and the original underwriting model. Identify the five variances with the largest effect on NOI. For each, tell me whether it’s temporary or structural, give your reasoning, estimate the annualized impact if it holds, and recommend one action to protect value. Return a table with columns for Issue, Dollar Impact, Temporary or Structural, Likely Cause, Recommended Action, and Urgency. Flag anything that would change the exit valuation.

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Ending the Circular Hold-Sell-Refinance Debate | Doug Banerjee

Every investment committee has sat through this one. Do we sell now, or refinance and wait. Everybody’s got an instinct, nobody’s got a framework, and forty minutes later we’re right back where we started.

Now I run all three paths through the same structure before we sit down. The part I actually use is the last section, where it names the two or three assumptions that would flip the answer and how far they would have to move. That turns an argument about opinions into a conversation about a handful of numbers we can pressure-test.

Advanced Prompt Example

You are an investment committee analyst. Using the attached operating data, current debt terms, market comps, projected capital needs, and our return targets, compare three strategies for this asset: hold, sell now, and refinance. Score each on projected value, risk, liquidity, capital required, timing, and investor outcome. Then name the two or three assumptions that, if they moved, would change the recommendation, and state how far each would have to move. Be conservative and show your reasoning.

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Writing the Investor Letter That Holds Up | Lacey Willard

Investors can handle a soft quarter. What costs you their confidence is a thin explanation. The quarterly update is where a lot of that trust gets won or lost, and it’s usually written last, late, and under pressure.

I use AI to get to a strong first draft straight from the numbers, in plain language, with the temporary noise pulled apart from the structural story. Just as useful, it flags the one or two items that need a real partner-level explanation before anything goes out. The judgment stays mine. The draft just puts it where it belongs, on the substance. All of it runs inside a permissioned environment. LP-facing performance data and fund materials stay in our systems, and a person owns every number before it reaches an investor.

Advanced Prompt Example

You are drafting a quarterly investor update for a private real estate fund. Using the attached asset performance summary, budget variance, leasing activity, and capital events, write a clear, plain-language update for limited partners. Lead with what changed and why. Separate temporary noise from structural change. Flag any item that needs a partner-level explanation before this goes out. Keep the tone confident but not promotional, and don’t overstate results.

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A Few Things You Can Start Doing

• Make the model call every number temporary or structural. Summaries hide the story.
• Feed it the original underwriting alongside this month. The gap between them is the story.
• Always ask what would change the answer. The assumptions matter more than the output.
• Keep a person between the draft and anything an investor sees.
• Run it where the records already live. Investor and fund data stays inside a permissioned environment.

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This is the kind of work we teach in Greysteel’s CRE MBA program, drawn from live deals. The first cohort opens the second week of June. If underwriting discipline at scale is where you want an edge, reach out or keep an eye on the site.