“Do you use AI?” measures nothing. These five questions do.
Move beyond polished tool lists. Ask one practical question per AIMM maturity level, then look for the operating evidence—and warning signs—behind the answer.
No technical background required. Free to use in operational due diligence with attribution to AgenticInvestor.
Five diligence questionsEvidence to requestRed flags to recogniseBuilt on AIMM v1.4
Why these questions
Separate institutional capability from individual experimentation.
Most managers can name similar AI tools. The useful distinction is whether adoption is personal or repeatable, improvised or governed, invisible or auditable.
The question bank gives allocators a structured way to test those distinctions in a diligence conversation.
The question bank
Five questions. Five operating signals.
Ask for demonstrations and records where appropriate. Treat confident language as a prompt for evidence, not proof.
Q1Repeatability
“Show me one AI workflow your whole team runs to a single standard.”
Evidence to expect
A written workflow, defined human sign-off points and evidence that more than its author can run it.
Red flags
A tool list, a workflow held in one enthusiast’s head or reliance on a single advanced user.
Q2Ownership & boundaries
“Who owns your screening workflow, and what may AI never do without human sign-off?”
Evidence to expect
A named owner, written boundaries and consistent answers from senior and junior team members.
Red flags
Ownership belongs to ‘everyone’, boundaries rely on common sense or different people describe different controls.
Q3Audit, live
“For a recent deal, show me what AI produced, its sources and who approved it.”
Evidence to expect
A live deal record with run history, sources attached to claims and a visible approval trail.
Red flags
A policy document instead of a demonstration, or no answer about which models can see the firm’s data.
Q4Improvement loop
“What changed last quarter because an AI workflow underperformed—and how did you know?”
Evidence to expect
A specific example with a measure, the change made and the result that followed.
Red flags
Improvement described as philosophy, with no numbers, events or examples of anything being rolled back.
Q5Sovereignty
“Whose AI accumulates your manager’s judgement—and could they take it with them?”
Evidence to expect
A contractual answer covering data rights, exportable memory and portable workflows.
Red flags
Unclear ownership of accumulated knowledge, data or workflows—or no considered answer at all.
Using the bank
Read trajectory, not just position.
Add the questions to the operational section of the DDQ.
Always ask the sovereignty question; it is rarely rehearsed.
For significant claims, request a live workflow demonstration.
Ask whether the manager has self-assessed against AIMM.
Value a candid improvement plan over unsupported perfection.
The model underneath
Built on the AIMM maturity staircase.
The Agentic Investing Maturity Model gives operational-diligence intuition a five-level structure. LPs are welcome in the free AgenticInvestor community.