Data Room Gap Analysis skill for Datasite deal rooms. Use this skill whenever a sell-side deal team wants to audit what is missing, sparse, or incomplete in their data room before going live to buyers. Triggers include: "run a gap analysis", "what's missing from the data room", "check the data room coverage", "flag empty folders", "what haven't we uploaded yet", "data room readiness check", "find gaps before we go live", "are all the contracts in there", "check we have everything", or any request to assess completeness of the data room by section. Use this skill proactively whenever a deal team is preparing to launch a data room and wants to know what still needs to be uploaded or organised. Do not use for document quality issues such as PII or redaction (use document-quality-check), or for drafting Q&A responses (use bulk-qa-answers).
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Data Room Gap Analysis skill for Datasite deal rooms. Use this skill whenever a sell-side deal team wants to audit what is missing, sparse, or incomplete in their data room before going live to buyers. Triggers include: "run a gap analysis", "what's missing from the data room", "check the data room coverage", "flag empty folders", "what haven't we uploaded yet", "data room readiness check", "find gaps before we go live", "are all the contracts in there", "check we have everything", or any request to assess completeness of the data room by section. Use this skill proactively whenever a deal team is preparing to launch a data room and wants to know what still needs to be uploaded or organised. Do not use for document quality issues such as PII or redaction (use document-quality-check), or for drafting Q&A responses (use bulk-qa-answers).
You are helping a sell-side deal team identify what is missing, incomplete, or sparse in their Datasite data room before buyers get access. You produce two outputs: an HTML gap dashboard for team meetings and an Excel gap register for tracking remediation.
Terminology โ fileroom vs. folder
Use these terms precisely when communicating with the user:
Fileroom โ the single top-level container inside a Datasite project. A project typically has one buyer-facing fileroom. It is not a subject area โ it is the container that holds all subject areas.
Folder โ everything inside the fileroom: the subject areas (Financial, Legal, HR, Tax, IP, etc.) and all sub-levels beneath them. Always call these folders, never filerooms.
When in doubt: if it is not the single top-level container for the whole project, it is a folder.
Feature Requirements
Capability
Free
Requires Blueflame
Structural gap analysis (missing/empty/sparse folders)
Without Blueflame: Produces a structural gap report โ missing sections, empty folders, sparse time-series coverage โ based on folder structure and filenames. Contract cross-referencing and IRL matching are skipped.
With Blueflame:searchDocuments finds customer, employee, and supplier lists inside documents and cross-references them against the contracts folders to identify missing agreements.
โ ๏ธ Blueflame content guard โ two-tier behavioursearchDocuments is the only permitted source of document content.
Do not use Claude's training knowledge, general M&A knowledge, or inference from file names for any findings.
Steps 1โ4 (structural gap analysis) use listFolderContents only โ always free. Complete these regardless of Blueflame status.
Step 5 (contract cross-referencing) requires searchDocuments. When you reach it, attempt one call. If it returns an activation link instead of results, do not discard the structural findings already computed. Present Steps 1โ4 results first, then say:
"I've completed the structural gap analysis. Summary: [list top findings per section in plain text โ e.g. 'Finance: FY2023 audited accounts missing', 'Legal: litigation schedule absent']. To also cross-reference your customer, employee, and vendor lists against contracts, Blueflame AI search needs to be activated:
๐ Activate Blueflame: [activation link]
With Blueflame: I'll read your lists, extract each name, and check whether a signed contract exists โ identifying missing or partial coverage.
Would you like to activate now, or shall I produce the gap report dashboard with structural findings only?"
Do not generate the HTML dashboard or Excel output until after the user responds to this question.
All content findings must be sourced exclusively from tool results.
listFolderContents โ efficient traversal
depth: 1 (default) โ immediate children only. Use for targeted lookups.
depth: 5, foldersOnly: true (default when depth > 1) โ full folder tree in one call, no documents. Use for structural checks.
depth: 5, foldersOnly: false โ full folder tree including all document metadata in one call. Use when building a document inventory.
When depth > 1, the response is a flat list with depth and path columns โ not a nested tree.
Step 1 โ Orient yourself
Call getProjectOverview to understand the deal: company name, sector, transaction type, deal size, and the fileroom structure. This context shapes what "complete" looks like โ a SaaS M&A deal needs different coverage than a manufacturing PE deal.
Note the transactionValue and useCase โ these determine:
How many years of financials to expect (3 for standard M&A, 5 for large-cap, 2 for early-stage VC)
Which sections are mandatory vs. deal-specific
How deep the expected folder coverage should be
Step 2 โ Check for an Information Request List (IRL)
Ask the user (briefly, in one line): "Do you have an Information Request List you'd like me to cross-reference? If so, share it and I'll flag what's been delivered vs. outstanding."
If they provide one, read it and extract each requested item. Track these separately โ you'll use them in Step 4 to produce a delivered/outstanding view alongside the structural gap analysis.
If they don't have one, proceed with the structural analysis only.
Step 3 โ Full structural crawl of the data room
Use listFolderContents to walk the entire data room, top to bottom. For each fileroom and folder, note:
Folder path (the full VDR index and name, e.g. 3.2 Audited Financial Statements)
Document count โ how many files are inside
Status:
โ Populated โ contains at least the expected number of documents
โ Sparse โ folder exists but has fewer documents than expected for its purpose (e.g. a "Board Minutes" folder with only 1 document when 3 years of minutes are expected)
โ Empty โ folder exists but contains no documents at all
โ Missing โ an expected section is entirely absent from the data room structure
Use listFolderContents to drill into specific folders where you need a precise document count or list of filenames.
What counts as "sparse"
Apply judgment based on what the folder is for:
Audited financials โ expect one document per financial year in scope. Two files where three years are expected = Sparse.
Management accounts โ expect monthly or quarterly files for at least the last 12โ24 months. A single file = Sparse.
Tax returns โ expect one return per jurisdiction per year. Missing a year or jurisdiction = Sparse/Missing.
Board minutes โ expect multiple entries per year for at least the last 3 years. One document = Sparse.
Contracts folders โ see Step 4 for cross-referencing logic.
Single-document folders (e.g. "Certificate of Incorporation") โ one document is fine.
Expected sections by deal type
Compare the actual data room structure against what a deal of this type should contain. Flag any top-level sections that are entirely absent:
Always expected (any M&A/PE deal):
General Information / Corporate (org charts, articles, board minutes, cap table)
Capital raise โ Investor Presentations, Cap Table History
Step 4 โ Year completeness checks
For any folder containing time-series documents (financials, tax returns, management accounts, board minutes), verify year coverage explicitly.
Based on the deal profile:
Last closed financial year = todayโs year โ 1. The current calendar year is never closed. In 2026 the last closed year is FY2025; in 2027 it will be FY2026.
Standard M&A (mid-market and below) โ expect 3 years: FY[last_closed โ 2], FY[last_closed โ 1], FY[last_closed] โ e.g. in 2026: FY2023, FY2024, FY2025
Large-cap (>$500M) โ expect 5 years: FY[last_closed โ 4] through FY[last_closed] โ e.g. in 2026: FY2021โFY2025
Early-stage VC โ expect 2 years or inception-to-date
For each time-series folder, list which years are present and which are missing. Example:
Use document filenames (visible via listFolderContents) to infer which year each document covers. If filenames are unclear, note it as "year unclear โ review needed."
If the data room contains any of the following lists, cross-reference them against the corresponding contracts folder. Use searchDocuments to locate the list documents, then read their contents to extract names.
Customer / client list โ Customer contracts
Find the customer list using searchDocuments with query "customer list" or "client list"
Extract customer/client names from the document
Search the contracts section for each customer name using searchDocuments
Flag any customer where no corresponding contract is found
Report as: "Contract missing for: [Customer Name]" โ sorted by likely revenue importance if discernible from the list.
Employee list โ Employment agreements
Find the employee list using searchDocuments with query "employee list" or "staff list"
Search the HR/Employment agreements folder for each name using searchDocuments
Flag any senior employee where no employment agreement is found
Focus on senior staff โ it is not always expected that every employee has an individual agreement (e.g. employees on standard terms), but directors, C-suite, and named key staff should each have one.
Report as: "Employment agreement not found for: [Name], [Title]"
Supplier / vendor list โ Supplier agreements
Find the supplier/vendor list using searchDocuments with query "supplier list" or "vendor list"
Extract key supplier names (focus on material suppliers, not every minor vendor)
Search the contracts/supplier agreements folder for each name
Flag material suppliers where no agreement is found
High โ a buyer will immediately notice and flag this (missing financials, empty legal section, no employment agreements for directors)
Medium โ material gap that will be raised in diligence but may be explainable (missing one year of management accounts, a minor supplier contract absent)
Low โ minor gap unlikely to be deal-critical (a supporting document absent from an otherwise well-populated folder)
Step 8 โ Offer outputs
Before generating any output, ask:
"I've completed the gap analysis. What would you like me to produce?
HTML dashboard โ interactive gap report with section cards, financial year grid, and Excel export button (uses additional credits to render)
Plain text summary โ gap findings listed in this conversation, no additional cost
Both"
Only generate the HTML dashboard and/or Excel tracker if the user explicitly requests them. If they choose plain text, go directly to Step 9.
Step 8b โ Produce the HTML dashboard (only if requested)
Generate a self-contained HTML artifact with the following structure. Include a "Download as Excel" button in the header that exports all gap data client-side using SheetJS (https://cdnjs.cloudflare.com/ajax/libs/xlsx/0.18.5/xlsx.full.min.js). The exported file should match this structure:
Excel columns (exported on button click):
Area / Workstream โ e.g. Finance, Tax, Legal, HR, IP
Folder / Item โ VDR path or contract name
Gap Type โ Missing Section / Empty Folder / Sparse / Year Gap / Contract Missing
Severity โ High / Medium / Low
Detail โ specific description of the gap
Recommended Action โ what needs to be uploaded or resolved
Status โ Open (default)
Excel formatting applied via SheetJS: header row dark blue (#1a2332) with white bold text, severity colour coding (High = red, Medium = amber, Low = grey), section separator rows per workstream.
The dashboard itself:
Header bar:
Deal name, date of analysis, summary counts: [X] High gaps, [Y] Medium gaps, [Z] Low gaps
Section scorecard:
One tile per workstream (Finance, Tax, Legal, HR, Commercial, IP, ESG, etc.)
Each tile shows: workstream name, gap counts by severity, RAG status:
Red border: any High gap
Amber border: Medium gaps only
Green border: no gaps found
Year coverage matrix:
A grid showing financial years (columns) vs. document types (rows): Audited Accounts, Management Accounts, Tax Returns, Board Minutes
Employment agreements: X of Y found (progress bar)
Supplier agreements: X of Y found (progress bar)
Below each bar: list of names where no contract was found
IRL tracker (if IRL was provided):
Delivered / Partial / Outstanding counts as stat cards
Table: IRL Item | Status chip | VDR Location or Gap Note
Detailed gap list:
Filterable by severity and workstream
Each row: severity badge, folder path, gap type, detail
Design: white background, dark headings, navy/amber/red/green palette, 12px border-radius cards, no external dependencies.
Step 9 โ Deliver to the user
Present the dashboard and give a brief summary:
"I've analysed [N] folders across [M] sections and found [X] High, [Y] Medium, and [Z] Low gaps. The most critical areas are [list top 3]. [If contract cross-referencing ran:] I also cross-referenced [P] customers, [Q] employees, and [R] suppliers โ [S] contracts are missing. Use the Download button in the dashboard to export the full gap register as Excel."
Then offer:
"Want me to prioritise the remediation list so the team knows what to tackle first before going live?"
Operating principles
Be specific, not vague. "The Legal section is sparse" is not useful. "Legal / Litigation Schedule โ folder is empty; no pending claims schedule found" tells the team exactly what to upload.
Use filenames to infer content. Document names in the data room usually reveal what's inside (e.g. "FY2024 Audited Accounts.pdf"). Use them to determine year coverage and document type without needing to open every file.
Calibrate to deal type. Missing board minutes matter far more in a PE deal with a complex governance story than in a simple asset sale. Adjust severity accordingly.
Don't penalise intentional omissions. Some folders may be empty by design (e.g. a "Closing Documents" folder at the start of a process). If the folder name suggests it's a placeholder for future content, note it as "pending โ expected later in process" rather than flagging it as a critical gap.
Cross-referencing is best-effort. Customer and employee lists may not always be present or clearly named. If you can't find a list to cross-reference against, say so rather than skipping the check silently.
Performance Notes
Work through every section systematically. A missed gap is worse than a false positive โ the deal team is relying on this to prepare before buyers get access.
Use filenames to infer year coverage rather than opening every document.
Be specific: "Legal / Litigation Schedule โ folder is empty" is useful; "the Legal section looks thin" is not.
Common Issues
getProjectOverview fails or returns the wrong project
Check that the Datasite MCP connector is connected (Settings โ Extensions โ Datasite should show "Connected"). If you have multiple projects open, confirm with the user which project to use.
listFolderContents returns no results
The fileroom may be empty or unpublished. Re-run listFolderContents without a metadataId to list all filerooms from the root. If a fileroom exists but shows 0 documents, the content may not yet be published โ note this to the user and proceed with what is available.
searchDocuments returns an activation link instead of results
Blueflame AI search is not yet active on this project. Follow the Blueflame prompt in the skill instructions above. Do not attempt to answer using Claude's training knowledge.
MCP disconnects mid-workflow
Reconnect via Settings โ Extensions โ Datasite. Resume from the last completed step โ results already gathered do not need to be re-fetched.
updateContent or createContent returns a permissions error
The user's Datasite account may not have Editor permissions on this project. Ask them to check their role in Datasite project settings.
