Session Prep
Real estate decisions involve large sums and long commitments. Coming into a session with the right questions turns a general conversation into a specific, actionable analysis of your deal, property, or market question. This guide is organized into three sections: evaluating the specific opportunity, structuring the negotiation and deal terms, and navigating due diligence and next steps. Before your session, prepare the key numbers: asking price, your target return or budget, comparable properties you've looked at, and any concerns you've already identified. The most important thing to walk in with is a clear articulation of what you're trying to decide — buy or pass, how much to offer, or whether a specific investment thesis holds up. Advisors who specialize in real estate can move quickly when you come prepared with specific data rather than a general question.
1.What do the comparable sales or rental data say about whether this is priced fairly?
Gets you into the actual analysis immediately — not general market commentary.
2.What's the realistic cash-on-cash return for this investment, using conservative assumptions?
Forces a stress-tested number, not a best-case scenario that ignores vacancy, maintenance, and financing costs.
3.What are the top three risks specific to this property or deal that I might be underweighting?
Surfaces the non-obvious risks that only come from seeing many similar transactions.
4.Is this market likely to support the rent growth or appreciation assumptions in the underwriting?
Tests whether the deal's economics depend on favorable assumptions that may not materialize.
5.What terms beyond price are worth negotiating in this deal?
Most people focus only on price; experienced advisors know that closing timeline, contingencies, and inclusions can be equally valuable.
6.What would make you walk away from this deal?
Forces a clear articulation of deal-breakers — which often reveals risks you hadn't considered.
7.How does this deal compare to others you've seen in this market recently?
Gets you a real benchmark from current market experience, not just what the listing materials say.
8.What should I prioritize in my due diligence, and what would you pay particular attention to?
Experienced advisors know which due diligence areas are most likely to surface material issues for your property type.
9.Are there any red flags in the listing or deal structure that I should investigate further?
An independent expert reviewing a deal often sees things that motivated buyers or their agents overlook.
10.If this were your money, would you proceed on these terms?
The direct opinion question — forces a clear recommendation rather than endless considerations.