The 90-Day Legal AI Pilot-to-Production Plan (With Checklists)

Why pilots stall

Most legal AI pilots die of the same causes:

• No defined success criteria, so "it's promising" becomes the permanent verdict
• Too many use cases at once
• Pilot users chosen for enthusiasm, not representativeness
• No baseline, so there's nothing to compare against
• No decision date

This template forces each of those decisions before day one.

Before day 1: the pilot charter

Fill this out and get GC sign-off.

• Use case (one, maybe two): e.g., first-pass review of inbound NDAs
• Business problem: e.g., NDAs take 3 days; sales is frustrated
• Pilot users (5–10): Mix of enthusiasts and skeptics
• Executive sponsor: Name
• Pilot owner: Name (legal ops or legal engineer)
• Baseline metrics: Cycle time, touch time, volume, quality
• Success criteria: e.g., 40% faster, no drop in quality, 70% weekly usage
• Go/no-go date: Day 90
• Budget if we go: Estimated annual cost at full rollout

Days 1–30: set up and baseline

Week 1: Foundations

• ☐ Security and privacy review complete (no training on our data, retention settings confirmed)
• ☐ SSO and access configured for pilot users only
• ☐ Baseline metrics captured for the last 30–60 days
• ☐ Kickoff meeting: explain the why, the what, and the decision date

Week 2: Configuration

• ☐ Playbook or clause positions loaded
• ☐ Workflow connected to where work arrives (intake, email, CLM)
• ☐ Verification standard written: what must a human check before output is used?

Weeks 3–4: Guided use

• ☐ Short, use-case-specific training (30 minutes max)
• ☐ Office hours scheduled twice a week
• ☐ Feedback channel created (a Slack or Teams channel works)
• ☐ First usage report reviewed

Days 31–60: use it for real

Weeks 5–6: Full volume

• ☐ All pilot-scope work runs through the tool
• ☐ Track exceptions: where did AI get it wrong, and why?
• ☐ Refine playbook rules based on real misses

Weeks 7–8: Mid-pilot checkpoint

• ☐ Compare metrics to baseline
• ☐ Survey users (satisfaction, trust, time saved)
• ☐ Identify non-users and find out why
• ☐ Decide: continue as planned, adjust scope, or stop early

Days 61–90: prove it and decide

Weeks 9–10: Measure

• ☐ Final metrics versus baseline and success criteria
• ☐ Quality review on a sample of AI-assisted work
• ☐ Cost model at full rollout (seats, usage, implementation, admin time)

Weeks 11–12: Decide and plan

• ☐ Write a one-page results memo for the GC
• ☐ Go/no-go meeting held on the date set in the charter
• ☐ If go: rollout plan, training plan, and owner named
• ☐ If no-go: document what you learned and share it

Week 13: Communicate

• ☐ Share results with the department, including what didn't work
• ☐ Thank pilot users by name

Go/no-go criteria template

Go if all of these are true:

• Hit at least 80% of the primary success metric
• Quality equal to or better than baseline
• At least 60–70% of pilot users are active weekly
• Total cost is justified by time saved or spend avoided

No-go or extend if any of these are true:

• Accuracy issues that the vendor can't resolve
• Usage concentrated in one or two enthusiasts
• Security or contract terms still unresolved

The results memo (one page)

1. What we tested and why
2. Results versus success criteria (a simple table)
3. What users said (two or three quotes)
4. Cost at full rollout and expected return
5. Recommendation and next steps

The bottom line

A pilot without a decision date is a subscription. Set your criteria before you start, measure against a real baseline, and make the call on day 90. Need candidates to pilot? Compare options across the legal infrastructure and contracts categories on CorporateLegal.tech.