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Diligence Question Bank
The questions a ten-person deal team would ask without thinking, organised by area (financial, commercial, operations & people, legal & the deal), plus a...
$9
Diligence Question Bank
Example session with this skill installed
Use the Diligence Question Bank skill. Tailor the bank to Project Sentinel (Sentinel Fire & Safety, Inc.) using my gaps and red flags below. Keep what matters, add deal-specific questions, cut the irrelevant, mark the deal-critical ones, and group by Financial, Commercial, Operations & people, and Legal & the deal.
Red flags: Northgate about 22% (CIM p.9) vs "no customer above 15%" (CIM p.8). Founder-held licence (CIM p.14). Add-backs $340,000 (FS p.4). Tax receipts $5.95M vs TTM $6.21M (Tax p.1). 2009 system, untested export (CIM p.16). Change of control unreviewed (CIM p.19). Settlement in prior year (CIM p.17).
Gaps: no price, margins, cash flow, contract terms, customer list beyond the top five.
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- Compiled the diligence question bank
Diligence questions: Project Sentinel
[DC] means deal-critical: the answer could end the deal.
Financial
- [DC] Which twelve months does the $6.21M TTM cover, and how does it reconcile to the $5.95M of 2025 tax receipts (Tax p.1)? Are the prior years of $5.78M and $5.34M fiscal years, and which?
- [DC] Walk me through each add-back (FS p.4). For the $210,000 owner pay: total compensation and the cost of a replacement manager. For the $65,000: the agreement, date and booking period.
- Show ledger lines for the $41,000 vehicle and travel and the $24,000 charitable items.
- What is reported EBITDA for, and what are gross margin and cost of services? (FS p.2 refers to later pages that contain no figures.)
- What does the balance sheet look like, including vehicle financing? How much working capital does the business need?
- Who prepares the accounts, and have they been reviewed or audited? (Unaudited, FS p.5.)
Commercial
- [DC] Northgate Property Group, $1,366,000 (CIM p.9): contract term, renewal date, pricing, termination and change-of-control rights, and who holds the relationship?
- [DC] The CIM says no customer is above 15% (p.8) and shows 22% (p.9). Which is correct, and which accounts are above 10%?
- Provide the full customer revenue schedule: accounts 6 to 10 (together about $0.76M, mine) and beyond.
- Of the 78% "recurring" (CIM p.7), what share is fixed inspection fees alone, and what share is repair and call-out? (Definition at CIM p.22.)
- What are contract lengths, renewal terms, churn and rebids in the last three years?
- What price increases were made, and what happened to churn?
Operations & people
- [DC] What does the founder do day to day, and what happens the day after he leaves? Who holds key customer relationships?
- How many licensed technicians and what certifications? Are they staying, and on what terms?
- What breaks if volume rises by 20 percent? What are the next two years of capex?
- [DC] Has a full data export from the 2009 system ever been run, and what does it contain? What would migration cost?
Legal & the deal
- [DC] How does the fire protection contractor licence (CIM p.14) transfer or get replaced at close? Who else could hold it?
- [DC] Has anyone reviewed change-of-control and assignment provisions (CIM p.19)? Provide the Northgate clause first.
- What was the legal settlement, and are other claims pending or threatened (CIM p.17)? Provide the agreement.
- Why sell, and why now? Are you open to a seller note or earn-out?
- What is not in the data room that I should know about?
Cut as not relevant yet
Intellectual property ownership, supplier concentration and pipeline questions: the materials give no sign they matter here. Revisit if the data room shows otherwise.
This is an analytical aid and not investment, legal, tax or accounting advice. The Project Sentinel documents are synthetic test data.
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About this skill
The questions a ten-person deal team would ask without thinking, organised by area (financial, commercial, operations & people, legal & the deal), plus a prompt that tailors the bank to your specific deal. Use to build a management-meeting list or information request, when asked 'what should I ask', 'build my diligence questions', or 'prep my management meeting'.
Works with
Any agent that reads the SKILL.md standard and can read attached documents. No scripts, no network access, no installs.
Known limitations
It works only from the documents you provide and cannot verify anything outside them. Analysis, not investment, legal, tax or accounting advice; check the output against the source documents.
About the author
Original work, listed by its author: part of the free, MIT-licensed open-deal-kit,
https://github.com/MariusGithub13/open-deal-kit
The hosted version that writes a fully cited diligence brief across a whole data room is Deal OS:
How to use
Skills on Agensi run inside your AI agent. Copy the prompt, paste it into your agent, and it connects to Agensi and installs this skill for you. If a payment is needed, your agent shows it to you first.
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