Build an M&A diligence question list organized by risk category instead of a generic due-diligence template

I'm preparing diligence questions ahead of an M&A conversation and I don't want a generic due-diligence checklist pulled from a template — I want questions organized around the specific risk categories that matter for this deal, given what I already know and don't know about the target.

DEAL TYPE AND STAGE
Acquiring a competitor's book of business, early-stage conversations before an LOI

TARGET COMPANY OVERVIEW
~$4M ARR, 40 customers, founder-led, 12 employees, no external funding raised

WHAT WE ALREADY KNOW
Top 3 customers make up roughly 35% of revenue based on what the founder mentioned informally; no known litigation

SPECIFIC CONCERNS GOING IN
Customer concentration risk, whether key engineering staff would actually stay post-acquisition, and whether the founder-led sales process would transfer to our sales team

Organize the diligence questions into risk categories relevant to this specific deal — likely including financial (revenue quality, customer concentration, working capital), legal/contractual (change-of-control clauses, litigation exposure), operational (key-person dependency, systems and process maturity), and any category suggested by the specific concerns I named — do not just default to a generic four-category template if the concerns I listed point to something else that deserves its own category (e.g., a specific regulatory exposure). For each category, generate questions that probe what we don't already know rather than re-asking what's in the target overview I gave you — a diligence list that re-derives publicly known facts wastes the limited time available with the target's team. For the specific concerns I named, make sure at least one pointed, hard-to-deflect question directly addresses each one — not a soft version of the question that could be answered evasively without actually resolving the concern.

WHAT NOT TO DO
Do not invent a specific red flag about this target that I haven't given you evidence for — frame concerns as things to verify, not as findings, since you have no actual access to the target's real financials or legal history. Do not pad the list with generic questions that would apply to any company being acquired if they don't connect to what's actually known or unknown about this specific target.

OUTPUT FORMAT
Sections by risk category, each with 3-6 pointed questions. A short "highest priority" subsection at the top pulling out the 5 questions across all categories most directly tied to the specific concerns named. Close with one line noting this is a structuring aid to prepare for diligence conversations and does not substitute for qualified legal, accounting, or M&A advisory review of the actual target materials.