Diligence Question Builder
Build a prioritised diligence list that attacks the thesis, not a generic checklist.
Seat
PE · IB
Level
Associate
Runtime
~25 min
Output
Prioritised diligence question list by workstream
What this helps you accomplish
Generate and rank diligence questions from the investment thesis: for each pillar and each key risk, what evidence would confirm or kill it, who has that evidence, and what to ask first when management time is scarce.
Delegate · Verify · Decide
The core L3VLUP principle: AI output is never automatically correct. Know what to hand off, what to check, and what only you can own.
Delegate
AI is good enough to do this.
- • Generating candidate questions per workstream from the thesis
- • Grouping and deduplicating into a tracker format
- • Drafting data-request lists in standard form
Verify
AI accelerates you here, but a professional checks the work.
- • Questions are answerable from the named source
- • No question already answered in materials you hold — that costs credibility
Decide
Judgment the human owns. This is the skill.
- • Which three questions matter most — the kill-power ranking
- • What you’re willing to take on trust vs must verify
- • When you have enough to advance vs walk
Inputs required
- Thesis pillars and key risks (or the teaser/CIM)
- Process stage and access level (management meeting, data room, expert calls)
The workflow
- 1
Map thesis to evidence
For each pillar: what would have to be true, and what data proves it?
- 2
Map risks to tests
For each risk: what’s the cheapest fastest way to size it?
- 3
Rank by kill-power
Questions that could kill the deal go first — you want bad news early and cheap.
- 4
Route by source
Management vs data room vs experts vs desktop. Don’t burn a management meeting on data-room questions.
- 5
Draft the asks
Specific, answerable questions — "walk me through churn by cohort for FY24-26", not "tell us about retention".
Run this skill
Any listed company, anywhere. Ticker or name.
Quality checklist
The output isn’t done until every box ticks.
- Every thesis pillar has at least one confirming and one killing test
- Top-5 list fits a 45-minute management meeting
- Each question names its source and owner