Prepare YOUR data room for a fundraise, acquisition, or bank diligence -- builds the checklist for your deal stage, sweeps your folders for what you already have, produces a gap report, and organizes everything into the structure buyers and investors expect. The sell-side complement to cowork-deal-room.
SkillScore82Maintained
Automatic
◆Finance & Accounting pack
Last verified 8/24/2026
What it changes
Passed 17 of 21 test cases with the skill, and 11 of 21 without it.
Without skill50%
With skill82%
Checks it passed that the model alone missed
Frames judgment calls for legal counsel decision.
Classifies the draft file under the status HAVE-BUT-DRAFT.
Uses the status code HAVE-BUT-STALE to classify outdated documents.
and 10 more in the full report
8 fixed10 passed either way3 still failing1 broke
Pass-rate lift
+32 pp
Tokens
+44%
Agent turns
0%
Response time
+11%
Model gemini-3.6-flashMeasured 8/24/2026v118 of 22 cases passed with skill · 21 comparable
Tokens, turns and time describe resource use, not a dollar price.
See it in action
One of 8 test cases the skill fixed. Same model, same prompt, with and without the skill.
1 of 8
Prompt
We are preparing for an acquisition deal. Please process our documents in `/company_records`, build a structured data room directory with numbered sections matching the deal checklist, copy the files over using clean standardized file names, and generate a master INDEX.md file mapping each requirement to its file path. Please make sure our source folder remains untouched.
What was checked, without and with the skill
Checked
Without skill
With skill
Copies documents to the data room directory rather than moving source files.
Missed
Passed
Prefixes destination filenames with section numbers matching the checklist.
Missed
Passed
Generates an INDEX.md file mapping checklist requirements to document paths.
Missed
Passed
case-02 · gemini-3.6-flash · 8/24/2026 · answers are capped and redacted
What's inside
The instructions your model reads when the skill loads.
SKILL.md27 linessingle file
Cowork Data Room Builder
Prepare a data room the way a banker's analyst does: know what the other side's diligence team will ask for before they ask, find it or flag it, and present it in the structure they expect. Inputs: the deal type (seed/Series A/growth round, acquisition, loan) and one or more folders of company documents.
Workflow
Build the request list. Generate the diligence checklist for the stated deal type and stage: corporate records, cap table and securities, financials, material contracts, IP, employment, tax, insurance, litigation, and (for later stages) customer concentration and compliance. Present it for approval -- the user may know their acquirer's quirks.
Sweep. Walk the provided folders and match every document to a checklist item. Classify each match FINAL (executed/signed), DRAFT, or STALE (superseded or older than the period requested). One file can satisfy multiple items.
Gap report. Output the checklist with status per item: HAVE, HAVE-BUT-DRAFT, HAVE-BUT-STALE, MISSING. Rank the missing items by how early diligence will hit them (corporate formation docs and cap table before customer contracts). This report is the deliverable that saves the deal timeline.
Organize. On approval, build the data room folder structure (numbered top-level sections matching the checklist), copy -- never move -- documents in with clean names (3.2-msa-acme-corp-executed-2025.pdf), and write INDEX.md mapping every checklist item to its file.
Red-flag pass. Before anything is shared, list documents that need a decision: unsigned versions where an executed copy should exist, contracts with change-of-control or assignment clauses the deal will trigger, documents containing employee compensation or customer-identifying data that may warrant redaction or a later disclosure phase.
Rules
Copy, never move. The data room is a curated export; source folders stay untouched.
Never place a draft where a final belongs without labeling it DRAFT in the filename and index.
Never redact or exclude documents silently -- list redaction candidates and let counsel decide.
The gap report states what was searched, so "MISSING" means "not in the provided folders," not "does not exist."
Stage-appropriate depth: do not demand SOC 2 reports from a pre-seed company; do not omit them for a growth round.
This is preparation support, not legal or securities advice. Frame judgment calls for counsel.
Quick Commands
"Build the checklist for [deal type]" -- step 1 only
"What am I missing?" -- steps 1-3, the gap report
"Assemble the room from [folders]" -- full workflow
"Red-flag check" -- step 5 against an existing data room