data-room

When the user wants to prepare a due diligence data room for fundraising, or when an investor has requested additional materials after a pitch. Also activates for "data room", "due diligence", "DD checklist", or "what documents do investors need?".

Quality

51%

Does it follow best practices?

Impact

—

No eval scenarios have been run

Securityby

Passed

No known issues

Optimize this skill with Tessl

npx tessl skill review --optimize ./skills/data-room/SKILL.md

Quality

Content

64%

Reviews the quality of instructions and guidance provided to agents. Good implementation is clear, handles edge cases, and produces reliable results.

This is a strong, domain-rich skill with highly actionable content — the master checklist, stage-specific scoping, access control guidance, and red flags section provide genuine value that Claude wouldn't know by default. The main weaknesses are the monolithic structure (could benefit from splitting detailed reference material into separate files) and the lack of explicit validation/feedback loops in the workflow. Overall it's a well-crafted skill that would produce useful outputs.

Suggestions

Add explicit validation checkpoints in the workflow — e.g., after step 4 (audit), confirm findings with the founder before proceeding to draft missing items; after step 5, verify drafts meet investor-specific requirements.

Split the master checklist and stage-specific scoping into a referenced file (e.g., DD-CHECKLIST.md) to keep the main SKILL.md as a concise overview with clear pointers to detailed materials.

Dimension	Reasoning	Score
Conciseness	The content is mostly efficient and well-organized, but includes some unnecessary verbosity — for example, the 'When to Use' section largely restates the skill description, and some checklist items could be more compressed. The master checklist is detailed but justified given the domain complexity.	2 / 3
Actionability	Highly actionable with concrete checklists, specific folder structures, exact criteria (e.g., '409A <12 months old', 'customer concentration <20%'), specific tool recommendations (Carta, Pulley, DocSend), and clear examples of good outputs. Claude can directly generate useful artifacts from this.	3 / 3
Workflow Clarity	The 6-step workflow is clearly sequenced and logical, but lacks explicit validation checkpoints or feedback loops. For a process involving document auditing and completeness checking, there should be a verify/fix cycle — e.g., after auditing existing materials, validate findings with the founder before drafting missing items.	2 / 3
Progressive Disclosure	The content references related skills (pitch-deck, investor-research) and external context (startup-context.md), but the skill itself is a long monolithic document (~120 lines of substantive content). The master checklist, stage-specific scoping, and red flags sections could be split into referenced files to keep the main skill leaner.	2 / 3
	Total	9 / 12 Passed

Description

37%

Based on the skill's description, can an agent find and select it at the right time? Clear, specific descriptions lead to better discovery.

This description is heavily lopsided: it provides excellent trigger terms and activation conditions but completely omits what the skill actually does. A skill selector would know when to activate it but not what capabilities it provides, making it impossible to distinguish from other fundraising-related skills. The description needs to lead with concrete actions before the trigger clause.

Suggestions

Add a leading clause describing concrete actions, e.g., 'Generates due diligence checklists, organizes data room folder structures, and drafts document summaries for investor review.'

Restructure to follow the 'what it does + when to use it' pattern: start with specific capabilities, then follow with the existing trigger guidance.

Ensure the description uses third-person active voice for capabilities (e.g., 'Prepares data room templates', 'Creates DD checklists') to clearly communicate the skill's function.

Dimension	Reasoning	Score
Specificity	The description does not list any concrete actions or capabilities. It describes when to activate but never says what the skill actually does — no verbs like 'generates', 'organizes', 'creates checklists', etc.	1 / 3
Completeness	The 'when' is thoroughly covered, but the 'what' is entirely missing. The description never explains what the skill actually does — it only describes activation conditions. This is the inverse of the typical gap.	1 / 3
Trigger Term Quality	Excellent coverage of natural trigger terms: 'data room', 'due diligence', 'DD checklist', 'what documents do investors need', 'fundraising', 'investor', 'pitch'. These are terms users would naturally say.	3 / 3
Distinctiveness Conflict Risk	The trigger terms like 'data room' and 'DD checklist' are fairly niche, but without specifying what the skill does, it could overlap with other fundraising or investor-related skills. The domain is somewhat specific but the lack of capability description creates ambiguity.	2 / 3
	Total	7 / 12 Passed

Validation

90%

Warnings & errors only

Checks the skill against the spec for correct structure and formatting. All validation checks must pass before discovery and implementation can be scored.

Validation — 10 / 11 Passed

Validation for skill structure

Criteria	Description	Result
frontmatter_unknown_keys	Unknown frontmatter key(s) found; consider removing or moving to metadata	Warning

	Total	10 / 11 Passed

Repository: shawnpang/startup-founder-skills
Commit: 4ad31b4

Reviewed: 3 months ago

Table of Contents

Discovery Implementation Validation

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