90-Day Legal AI Strategic Roadmap
From First Pilots to Scaling Across the Business
How to Use This Roadmap
This template provides a proven framework for moving from AI readiness to measurable value in 90 days. Customize timelines, owners, and deliverables based on your organization's maturity level and resources. Each phase builds on the previous one—don't skip foundational steps.
Phase 1: Foundation & Planning
Days 1-30✓ Establish AI Task Force & Governance
Charter a cross-functional AI Task Force with clear mandate, roles, and meeting cadence. Define decision-making authority and escalation paths.
AI Task Force Charter
Meeting Schedule
✓ Complete AI Readiness Assessment
Conduct comprehensive assessment across Strategy, Data, Governance, Talent, and Technology dimensions. Identify current maturity stage and critical gaps.
Readiness Scorecard
Gap Analysis Report
✓ Draft AI Use Policy & Governance Framework
Create formal AI Use Policy covering acceptable use cases, data protection requirements, human oversight mandates, and escalation protocols. Align with ABA ethics and regulatory requirements.
AI Use Policy (Draft)
Risk Register
✓ Prioritize Quick-Win Use Cases
Apply prioritization matrix to identify 2-3 high-value, low-risk pilots. Focus on measurable ROI, data availability, and team adoption likelihood.
Prioritization Matrix
Pilot Proposals
✓ Secure Executive Sponsorship & Budget
Present business case with ROAI projections, cost of inaction analysis, and pilot roadmap. Secure budget approval and visible executive support.
Business Case
Budget Approval
Phase 2: Pilot Execution & Validation
Days 31-60✓ Launch Vendor Selection Process
Issue RFPs to shortlisted vendors. Conduct weighted evaluation across performance, compliance, integration, and cost. Execute proof-of-concept testing with real workflows.
Vendor RFP
POC Test Results
Vendor Selection
✓ Execute Data Preparation & Integration
Complete data inventory and classification. Implement data minimization protocols. Configure integrations with DMS, CRM, and core legal systems.
Data Inventory
Integration Architecture
✓ Launch First Pilot with 10-15 Users
Deploy AI solution to small pilot group. Capture baseline metrics before launch. Implement daily check-ins and feedback loops. Ensure human oversight protocols are followed.
Pilot Kickoff
Baseline Metrics
Weekly Progress Reports
✓ Deliver Role-Based Training
Provide tailored training for lawyers (responsible use), ops/IT (governance), and leaders (ROI tracking). Emphasize ethical guardrails and escalation protocols.
Training Materials
Completion Tracking
Phase 3: Measurement, Optimization & Scale Planning
Days 61-90✓ Measure Pilot ROI & Document Learnings
Compare post-pilot metrics to baseline. Calculate ROAI across operational, financial, cultural, and strategic dimensions. Document successes, failures, and optimization opportunities.
ROI Dashboard
Lessons Learned Report
✓ Refine Workflows & Governance Based on Feedback
Incorporate user feedback to optimize workflows. Update AI Use Policy based on real-world issues encountered. Strengthen oversight and escalation protocols.
Updated AI Use Policy
Optimized Workflows
✓ Present Results to Leadership & Board
Deliver executive presentation showcasing pilot results, validated ROI, lessons learned, and recommended next steps. Secure approval for enterprise-wide scaling.
Executive Presentation
Scaling Approval
✓ Develop Enterprise Scaling Plan
Create detailed roadmap for expanding successful pilots across the organization. Define rollout phases, resource requirements, training plans, and success metrics.
Scaling Roadmap
Resource Plan
Change Management Strategy
Key Milestones Summary
| Milestone | Owner | Timeline | Status |
|---|---|---|---|
| AI Task Force Chartered | General Counsel | Days 1-7 | Planning |
| Readiness Assessment Complete | Legal Ops | Days 5-10 | Planning |
| AI Use Policy Drafted | Risk/Compliance | Days 8-20 | Planning |
| Budget & Sponsorship Secured | General Counsel | Days 20-30 | Planning |
| Vendor Selected | Legal Ops + IT | Days 31-50 | Execution |
| First Pilot Launched | Pilot Lead | Days 40-60 | Execution |
| Pilot ROI Measured | Legal Ops | Days 61-75 | Scaling |
| Board Presentation Delivered | General Counsel | Days 75-85 | Scaling |
| Scaling Plan Approved | AI Task Force | Days 80-90 | Scaling |
Critical Success Factors
- Visible executive sponsorship throughout all 90 days
- Cross-functional AI Task Force with decision-making authority
- Baseline metrics captured before any pilot launch
- Human oversight integrated into every AI workflow
- Weekly progress reviews and rapid issue escalation
- Continuous user feedback and workflow optimization
- Transparent communication about successes and challenges
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