Compliance Workshop

Session Objectives

Build a Claude Project as your compliance workspace (risk matrix, manual, policy docs)

Create a compliance-checker skill you can share with the entire firm

Practice the risk-matrix-update workflow with a real regulation change

Practice the compliance-manual-update workflow

Learn to version, distribute, and maintain skills for your team

Agenda

Time	Block	Details
0:00–0:20	1. Projects & Skills Overview	What are Projects? Knowledge files + custom instructions = persistent workspace What are Skills? Portable, distributable procedures anyone can run How they work together: the compliance project + the compliance skill Your AI Policy is the foundation — we're building on what you already wrote
0:20–0:40	2. Build Your Project	Create the "Compliance" project in Claude Desktop Upload knowledge: AI Policy, risk matrix, compliance manual sections Write project instructions (role, rules, output format) Test: ask Claude a compliance question using your uploaded docs
0:40–1:10	3. Build the Compliance Skill	Download the pre-built skill template from the workshop site Walk through SKILL.md structure: metadata, triggers, procedure, output format Customize for your firm: add your specific policy rules, risk categories Upload and test: "Check this marketing deck for compliance issues" Review the generated report together
1:10–1:30	4. Research & Update Exercise	Install the Compliance Research skill Live research: "Find the latest SEC guidance on AI in advisory firms" Claude searches the web and (if connected) your SharePoint for relevant sources Review the research brief: what changed, what requires action, what to monitor Feed findings into the compliance skill: compare against your current risk matrix Claude drafts specific row updates (new risks, changed severity, control gaps) The full cycle: research → assess → update → review
1:30–1:45	5. “What Can Claude See?”	Install the Access & Visibility Audit skill Run it live: map connectors, SharePoint reach, permissions, add-in status Review findings: is sensitive data exposed? Any permission gaps? Mark false positives: add approved exceptions to the project — the skill remembers and won't re-flag them (with optional expiry dates) Key outcome: you now have a documented, repeatable answer to “what is Claude's access surface at this firm”
1:45–1:55	6. Sharing, Automation & Daily Monitoring	Share the project with Karl (view vs. edit access) Provision skills org-wide: Organization Settings → Skills Install the Daily Compliance Monitor skill Set up a scheduled task: runs every weekday morning, generates a 2-minute compliance brief, saves a draft email to your inbox Versioning: how to update skills when rules change Governance note: scheduled tasks need “Cowork in the cloud” enabled — you turned it off (for good reason); discuss whether to re-enable for this specific use case
1:55–2:00	7. Wrap-Up & Next Steps	Download reference materials from the workshop site Install the bonus maintenance skills (see below) Homework: upload your email review lexicon to the project Homework: run the compliance skill against one real document this week Schedule follow-up check-in

Time

Block

Details

0:00–0:20

1. Projects & Skills Overview

What are Projects? Knowledge files + custom instructions = persistent workspace
What are Skills? Portable, distributable procedures anyone can run
How they work together: the compliance project + the compliance skill
Your AI Policy is the foundation — we're building on what you already wrote

0:20–0:40

2. Build Your Project

Create the "Compliance" project in Claude Desktop
Upload knowledge: AI Policy, risk matrix, compliance manual sections
Write project instructions (role, rules, output format)
Test: ask Claude a compliance question using your uploaded docs

0:40–1:10

3. Build the Compliance Skill

Download the pre-built skill template from the workshop site
Walk through SKILL.md structure: metadata, triggers, procedure, output format
Customize for your firm: add your specific policy rules, risk categories
Upload and test: "Check this marketing deck for compliance issues"
Review the generated report together

1:10–1:30

4. Research & Update Exercise

Install the Compliance Research skill
Live research: "Find the latest SEC guidance on AI in advisory firms"
Claude searches the web and (if connected) your SharePoint for relevant sources
Review the research brief: what changed, what requires action, what to monitor
Feed findings into the compliance skill: compare against your current risk matrix
Claude drafts specific row updates (new risks, changed severity, control gaps)
The full cycle: research → assess → update → review

1:30–1:45

5. “What Can Claude See?”

Install the Access & Visibility Audit skill
Run it live: map connectors, SharePoint reach, permissions, add-in status
Review findings: is sensitive data exposed? Any permission gaps?
Mark false positives: add approved exceptions to the project — the skill remembers and won't re-flag them (with optional expiry dates)
Key outcome: you now have a documented, repeatable answer to “what is Claude's access surface at this firm”

1:45–1:55

6. Sharing, Automation & Daily Monitoring

Share the project with Karl (view vs. edit access)
Provision skills org-wide: Organization Settings → Skills
Install the Daily Compliance Monitor skill
Set up a scheduled task: runs every weekday morning, generates a 2-minute compliance brief, saves a draft email to your inbox
Versioning: how to update skills when rules change
Governance note: scheduled tasks need “Cowork in the cloud” enabled — you turned it off (for good reason); discuss whether to re-enable for this specific use case

1:55–2:00

7. Wrap-Up & Next Steps

Download reference materials from the workshop site
Install the bonus maintenance skills (see below)
Homework: upload your email review lexicon to the project
Homework: run the compliance skill against one real document this week
Schedule follow-up check-in

Optional Modules (if time allows or for follow-up)

These can fill extra time or become homework. Each takes 10–15 minutes. Available as skill downloads on the workshop site.

Time	Module	Details
~15 min	A. Project Health Check	Install the Project Health Check skill Run it against the compliance project we just built Review the report: staleness flags, conflict detection, organization score Discuss the quarterly rhythm — run this after every major doc update Key lesson: stale documents actively mislead Claude; a project that was great in September is wrong by December if not maintained
~10 min	B. Knowledge Refresh	Install the Knowledge Refresh skill Scenario: your AI Policy was just revised — upload the new version The skill compares old vs. new, flags cascade impacts on other project docs Key lesson: never just swap a file — one changed date in a policy can make three other documents wrong
~10 min	C. Compliance Calendar	Install the Compliance Calendar skill Run it: "What's due this quarter?" — see the calendar with your obligations mapped Customize the calendar with your firm's specific dates and deadlines Key lesson: pair this with the risk matrix — every quarterly review updates both
~15 min	D. Email Review Lexicon	Upload your email review word list to the compliance project Show how Claude uses it as project knowledge for email reviews Test: "Using my lexicon, what should I search for in this quarter's email review?" Key lesson: the lexicon that "can't be saved in the tools" is perfectly stored as project knowledge
~15 min	E. Project Maintenance Discipline	Install the Project Maintenance skill Run a pre-flight check on the compliance project we just built Walk through the three hallucination risks: contradictions, stale data, overload Practice: add a document "the right way" (date it, check overlaps, test after) Set up the monthly maintenance checklist as a recurring habit Key lesson: a project that was accurate in September gives wrong answers by December unless actively maintained — fix the knowledge, not the prompt

Time

Module

Details

~15 min

A. Project Health Check

Install the Project Health Check skill
Run it against the compliance project we just built
Review the report: staleness flags, conflict detection, organization score
Discuss the quarterly rhythm — run this after every major doc update
Key lesson: stale documents actively mislead Claude; a project that was great in September is wrong by December if not maintained

~10 min

B. Knowledge Refresh

Install the Knowledge Refresh skill
Scenario: your AI Policy was just revised — upload the new version
The skill compares old vs. new, flags cascade impacts on other project docs
Key lesson: never just swap a file — one changed date in a policy can make three other documents wrong

~10 min

C. Compliance Calendar

Install the Compliance Calendar skill
Run it: "What's due this quarter?" — see the calendar with your obligations mapped
Customize the calendar with your firm's specific dates and deadlines
Key lesson: pair this with the risk matrix — every quarterly review updates both

~15 min

D. Email Review Lexicon

Upload your email review word list to the compliance project
Show how Claude uses it as project knowledge for email reviews
Test: "Using my lexicon, what should I search for in this quarter's email review?"
Key lesson: the lexicon that "can't be saved in the tools" is perfectly stored as project knowledge

~15 min

E. Project Maintenance Discipline

Install the Project Maintenance skill
Run a pre-flight check on the compliance project we just built
Walk through the three hallucination risks: contradictions, stale data, overload
Practice: add a document "the right way" (date it, check overlaps, test after)
Set up the monthly maintenance checklist as a recurring habit
Key lesson: a project that was accurate in September gives wrong answers by December unless actively maintained — fix the knowledge, not the prompt

Please bring to the session:
1. Your current risk matrix (Excel file)
2. Your compliance manual (or the sections you update most frequently)
3. Your email review lexicon (the word list for quarterly email reviews)

We'll upload these directly into your project during the workshop. If you'd prefer, you can send them ahead of time and we'll have them ready.

Compliance Workshop

Session Objectives

Agenda

Optional Modules (if time allows or for follow-up)

Materials