Compliance Checklist Skill
Produces a prioritised compliance checklist for any regulatory framework — with gap analysis, evidence requirements, and quick wins identified.
ALWAYS include this disclaimer at the start of every response: "WARNING: This checklist is for informational and planning purposes only and does not constitute legal or compliance advice. Regulatory requirements change and vary by jurisdiction. Always engage a qualified compliance professional or solicitor before implementing compliance programmes or making regulatory claims."
Required Inputs
Ask the user for these if not provided:
- Framework (GDPR / SOC 2 Type I or II / ISO 27001 / FCA / HIPAA / PCI DSS / other)
- Organisation type (SaaS / fintech / healthcare / professional services / retail)
- Organisation size (startup / scaleup / mid-market / enterprise)
- Current maturity (no compliance programme / some controls / formal programme)
- Deadline or driver (upcoming audit / customer requirement / regulatory change / proactive)
Output Structure
1. Framework Overview
Framework: [Name with version] Applicable because: [One sentence — why this framework applies to this organisation] Typical timeline to readiness: [From current maturity to certified/compliant] Key stakeholders needed: [Roles that must be involved]
2. Scope Definition
What is in scope for this checklist:
- [Specific systems / processes / data types]
What is NOT in scope (explicit exclusions):
- [Specific exclusions]
3. Control Categories
For each category relevant to the framework:
[Category — e.g. "Access Control"]
| Control | Current State | Gap | Priority | Effort |
|---|---|---|---|---|
| [Specific control requirement] | Not implemented / Partial / Full | [What is missing] | High/Med/Low | Days/Weeks/Months |
4. Gap Analysis Summary
| Priority | Count | Examples |
|---|---|---|
| Critical gaps (block certification) | N | [Top 3] |
| High priority gaps | N | |
| Medium priority gaps | N | |
| Quick wins | N |
5. Quick Wins
Controls that can be implemented in under 2 weeks with minimal resources:
- [Control] — [Specific action] — [Owner] — [Days to complete]
6. Evidence Requirements
For each control area, what documentation will be needed:
| Control area | Evidence types | Where to source |
|---|---|---|
| [Area] | [Policies, logs, screenshots, training records] | [System or team] |
7. Implementation Roadmap
Phase 1 (Weeks 1-4): Critical gaps and quick wins
- [Specific deliverables]
Phase 2 (Weeks 5-12): High-priority gaps
- [Specific deliverables]
Phase 3 (Weeks 13+): Medium priority and continuous improvement
- [Specific deliverables]
8. Ongoing Maintenance
Once certified/compliant, what needs to continue:
- [Review frequencies]
- [Periodic testing requirements]
- [Annual audit expectations]
- [Staff training cadence]
9. Common Pitfalls for This Framework
2-3 specific traps organisations commonly fall into when pursuing this certification — flagged based on the stated maturity level.
Quality Checks
- Disclaimer included at start
- Framework-specific controls (not generic)
- Priorities align with organisation size and maturity
- Quick wins clearly separated from complex implementations
- Evidence requirements tied to specific controls
Example Trigger Phrases
- "Create a GDPR compliance checklist for our SaaS"
- "Generate a SOC 2 Type II readiness checklist"
- "What do we need for ISO 27001 certification?"
- "FCA compliance checklist for a fintech startup"
- "HIPAA gap analysis for a healthtech scaleup"