Verified against ChatGPT · 2026-08-14
Build a due diligence question list scoped to what actually makes this specific deal risky
Produces a prioritized due diligence question list for a specific acquisition or investment, organized by which questions matter most given the deal's actual shape, rather than a generic due diligence template.
The prompt
Ready to copy — highlighted parts are example details you can swap.
Build a due diligence question list for the deal described below. I need this scoped to what actually matters for this specific transaction, not a generic due diligence checklist copied across every deal type. DEAL TYPE AND STRUCTURE Acquiring a majority stake (70%) in a privately held software company, cash and stock mix. TARGET COMPANY DESCRIPTION 20-person B2B SaaS company selling to mid-market logistics companies, roughly $3M ARR. OUR BIGGEST CONCERNS GOING IN Customer concentration — we suspect a large share of revenue comes from just a couple of clients. WHAT WE ALREADY KNOW We know their top client is a logistics firm that's been with them 3 years; we don't know contract terms or renewal history. BUILDING THE QUESTION LIST Organize questions by category (financial, legal/contractual, IP, employment, operational, customer concentration — whichever categories the deal type and target description actually make relevant, not every possible category by default). Within each category, prioritize the questions that follow from the concerns stated above rather than treating every category as equally important — if customer concentration is the named worry, that category's questions should be sharper and more numerous than a category nobody flagged as a concern. Write each question as something you'd actually ask the target or their counsel, specific enough that a vague or evasive answer would itself be informative — "describe your customer contracts" is weak; "what percentage of revenue comes from your top 3 customers, and do those contracts have change-of-control termination rights" is a real question. Do not repeat what's already known — if I told you we already know something, don't ask a question that just re-asks it; ask the follow-up question that goes deeper from that known starting point. WHAT NOT TO DO Do not answer the due diligence questions yourself or predict what the target's answers will likely be. Do not assess deal risk or recommend proceeding or walking away — this is a question-generation task, not a deal recommendation. OUTPUT FORMAT 1. Question list by category, prioritized within each category by relevance to stated concerns. 2. A short flagged list of any category where you have too little information about the deal to write specific questions, with a note on what's needed. 3. A closing note stating this is a due diligence question-preparation aid, not legal or financial due diligence itself, and the actual diligence process, document review, and risk assessment should be conducted by qualified legal and financial advisors before any decision to proceed with the transaction.
Customize
Optional — swap in your own details for the highlighted parts above.
Why this works
A generic due diligence checklist treats every deal identically, which is exactly wrong — a customer-concentration worry in a $3M ARR SaaS acquisition needs sharp, specific questions about top-client contract terms and renewal history, while the same checklist applied to a manufacturing asset purchase would waste effort on categories that don't actually carry the deal's real risk; requiring the deal structure, target description, and named concerns up front is what lets the model weight categories by actual relevance instead of listing all of them with equal, shallow coverage. Instructing the model to write questions specific enough that an evasive answer would itself be informative targets a real weakness in how models default to writing diligence questions — "describe your customer contracts" is the kind of question a target's counsel can answer with three vague sentences that sound complete but reveal nothing, while a question asking for a specific percentage and a specific contract term structurally can't be answered evasively without the evasion itself being a signal worth noting. The instruction not to re-ask what's already known and instead go one level deeper is what keeps the list from wasting the actual diligence conversation's limited time restating things the buyer's team has already established, and pushes the model to produce the harder, more useful follow-up question instead of the easy first-level one. The prohibition on predicting answers or recommending whether to proceed is the necessary boundary here: due diligence question generation is a legitimate prep task, but assessing the deal itself requires the actual documents, financials, and legal review that this exercise explicitly hasn't done, and a model volunteering a walk-away recommendation from a short description would be substituting a guess for the entire diligence process this list is meant to kick off.
What you get back
Customer Concentration: What percentage of total revenue comes from your top 3 customers individually and combined? For your largest customer specifically (the 3-year logistics client), what does the current contract term look like, when is the renewal date, and does it include a change-of-control termination right that could be triggered by this acquisition? Flagged: too little information provided about the company's cap table to write specific questions on equity structure — need target's cap table before that category can be scoped. This is a due diligence question-prep aid, not the diligence process itself — qualified legal and financial advisors should conduct the actual review before any decision to proceed.
Verified against
ChatGPT GPT-5.1 · 2026-08-14
Changelog
- 2026-08-14 — Initial publish, verified against ChatGPT GPT-5.1.
Need this built into your business?
If a prompt isn't enough — what Scult builds, built and maintained for you — that's Scult's day job.
EXPLORE WHAT SCULT BUILDS
