ChatGPT 5 PRO User Series No. 1: Policy Overhauls and Compliance
Or Why a $200 a Month Plan Can Be Worth It
Today, I’d like to launch a series in which we take a closer look at how, when, and why to use more advanced models, such as ChatGPT 5 PRO (yup, the model that only $200-a-month types have access to).
That may seem like a steep price to pay, but consider the complexity that it can tackle. We’re talking thousand- or even million-dollar jobs.
When you save that much in time, money, and/or frustration, the costs can totally be worthwhile.
Ask any C-Suite executive or small business owner. So, without further ado, let’s get started!
Today’s Problem
You’ve got a pile of outdated policies. They contradict each other, reference dead programs, and don’t reflect current regulations. Here’s how I’d use ChatGPT 5 PRO to turn that mess into a clean, compliant, human-readable policy set—quickly and safely.
0) Prep (15–60 min)
Scope: List the policy families (HR, IT/security, finance, safety, data/privacy, procurement).
Authorities to map: Identify the frameworks/laws you care about (e.g., FMLA, FCRA, ADA, HIPAA, PCI-DSS, SOC 2, ISO 27001, NIST 800-53, state regs, union contracts).
Inputs: Gather source docs: current policies (PDF/Word), prior redlines, org chart, risk register, incident postmortems, and any “non-negotiables” from Legal/Compliance/HR.
Why 5 PRO here? It tolerates messy, mixed-format corpora and keeps long-range context straight—so you can load a lot at once without losing the thread.
1) Intake & Canon Build
Goal: Create a single source of truth (the “canon”) and a map of what’s missing.
How (prompts you can copy):
You are my Policy Canon Builder. Ingest the attached policies and produce:
1) A policy catalog: title, owner, effective date, status, last update.
2) A dependency map: what each policy references (laws, standards, other policies).
3) A coverage matrix: which requirements from [list your frameworks/laws] are covered, partially covered, or missing.
Flag duplicates/near-duplicates and any “zombie” references (obsolete programs/roles).
Return as: a) executive summary, b) CSV tables, c) a visual outline.
Ask 5 PRO to normalize titles, date formats, and owners; export a CSV you can open and share.
Why 5 PRO: It can absorb hundreds of pages and still produce a coherent crosswalk (coverage matrix) without collapsing into shallow summaries.
2) Contradiction & Risk Pass
Goal: Surface conflicts, ambiguity, and outdated guidance.
How:
Act as a Policy Auditor. Using the canon, list:
- Direct conflicts (A says X, B says not-X), with quotes and page refs.
- Ambiguities (undefined terms, vague enforcement).
- Outdated/illegal guidance.
- Operational conflicts (what we say vs. what our incident history shows we actually do).
Rank each item by risk (regulatory, legal, operational, reputational) and likelihood.
Propose a resolution leaning toward current law and least operational friction.
Output: A risk-ranked fix list with page-level citations and a “who needs to sign off” column.
Why 5 PRO: Better at structured critique and risk ranking, not just calling everything “problematic.”
3) Compliance Crosswalk
Goal: Prove alignment to external requirements.
How:
Create a requirement-by-requirement crosswalk for [frameworks/laws].
For each requirement: cite where we meet it (policy name/section), where we partially meet it, or where we’re missing coverage.
For gaps, propose specific policy language that would close them, with rationale.
Ask for a gap list that includes: “sample clause,” “owner,” “dependencies,” and “rollout considerations.”
Why 5 PRO: It keeps the traceability chain intact—requirement ➜ clause ➜ owner—across a large corpus.
4) Rewrite with Guardrails
Goal: Rewrite for clarity, consistency, and enforceability.
House style & constraints (tell it once):
Readability target (e.g., Grade 8–10).
Consistent terms (“employee” vs. “associate,” “will” vs. “must”).
Standard sections (Purpose, Scope, Definitions, Policy, Exceptions, Enforcement, Review Cycle).
Jurisdictional variants if needed (multi-state/multi-country).
How:
You are my Policy Rewriter. For each policy:
- Keep intent, fix contradictions, insert gap-closure clauses.
- Apply house style and definitions.
- Produce: a) clean draft, b) redline summary showing what changed and why, c) 1-page “What Changed & Why It Matters” explainer for employees.
Why 5 PRO: Stronger at long-form consistency—definitions, cross-references, and terminology don’t drift mid-document.
5) Internal Red Team & Readiness Check
Goal: Break it before Legal has to.
How:
Act as a Policy Red Team. Stress-test the drafts against real scenarios:
- Edge cases (unionized vs. non-union roles, remote vs. on-site, contractors).
- Conflicting jurisdictions.
- Past incidents: would these drafts have prevented, detected, or mitigated them?
List failure modes and edits needed. Return a QA checklist we can reuse.
Optionally, run a plain-language check: “Rewrite the Summary for a non-expert.”
Why 5 PRO: Better at multi-scenario simulation and spotting hidden side effects.
6) Rollout Kit
Goal: Adoption, not just a pretty binder.
How:
Package each policy with:
- 150-word employee announcement
- Manager talking points
- 5-question comprehension quiz
- “Day 1” checklist for affected teams
- 30/60/90-day metrics to confirm adoption
Ask for a versioning plan (owners, review cadence, renewal dates) and a sunset plan for obsolete docs.
Why 5 PRO: It can draft nuanced comms for different audiences without losing policy fidelity.
What to Ask 5 PRO to Deliver (Artifacts)
Policy Catalog CSV and Coverage Matrix (framework × policy).
Contradiction/Risk Report with citations.
Gap-Closure Clauses with rationale and owners.
Clean Drafts + Redline Summaries.
Rollout Kit (announcements, talking points, quiz, checklists).
QA/Red Team Checklist you can reuse.
Why Use 5 PRO (Not a lighter model)
Depth & planning: Handles multi-step plans and keeps them aligned across dozens of outputs.
Long-context integrity: Tracks definitions and cross-references over hundreds of pages.
Traceability: Cites where requirements are met or missing; preserves an audit trail.
Risk reasoning: Prioritizes changes by business risk, not just word edits.
Audience-aware rewrites: Produces exec summaries and frontline explainers that stay true to the policy.
Guardrails (Use them every time)
Keep privileged or sensitive docs out of any system you can’t govern.
Human-in-the-loop: Legal/Compliance must approve final language.
Preserve change history (versioning, owners, next-review dates).
Pilot high-impact policies with one department before org-wide rollout.
Try It: Mini-Pilot in Your Org (1–2 weeks)
Choose one policy family (e.g., Acceptable Use or Leave of Absence).
Gather 5–10 related docs + your chosen framework(s).
Run Steps 1–3 to get the catalog, crosswalk, and gap list.
Rewrite one policy via Step 4, red-team it, and ship the rollout kit.
Measure: review time saved, contradictions eliminated, support tickets reduced.
Call to Action
Want to find a specific 5 PRO use case in your domain?
List 3 policy pain points (contradictions, confusion, compliance exposure).
Name the external authority you answer to (regulator, standard, contract).
Pick one pilot policy and run the mini-playbook above.
Quantify wins (hours saved, risks removed, clarity gained) and decide whether to scale.
For more hands-on prompts and templates like the ones above, subscribe to my mAIn Street newsletter for weekly, practical AI workflows tailored to real teams.
And if you’ve found 5 PRO or any other model to be of value, I’d love to see how you’re using it. Feel free to share in the comments section below!