90-Day Legal AI Strategic Roadmap

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.
Owner: General Counsel / Legal Ops Lead
Timeline: Days 1-7
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.
Owner: Legal Ops / Innovation Lead
Timeline: Days 5-10
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.
Owner: Risk/Compliance + Legal Ops
Timeline: Days 8-20
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.
Owner: AI Task Force
Timeline: Days 15-25
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.
Owner: General Counsel
Timeline: Days 20-30
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.
Owner: Legal Ops + IT
Timeline: Days 31-50
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.
Owner: IT + Data Governance
Timeline: Days 35-55
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.
Owner: Pilot Lead + AI Champions
Timeline: Days 40-60
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.
Owner: Learning & Development + Legal Ops
Timeline: Days 45-60
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.
Owner: Legal Ops + Pilot Lead
Timeline: Days 61-75
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.
Owner: AI Task Force
Timeline: Days 70-80
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.
Owner: General Counsel
Timeline: Days 75-85
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.
Owner: AI Task Force + Legal Ops
Timeline: Days 80-90
Scaling Roadmap Resource Plan Change Management Strategy

Key Milestones Summary

Milestone Owner Timeline Status
AI Task Force CharteredGeneral CounselDays 1-7Planning
Readiness Assessment CompleteLegal OpsDays 5-10Planning
AI Use Policy DraftedRisk/ComplianceDays 8-20Planning
Budget & Sponsorship SecuredGeneral CounselDays 20-30Planning
Vendor SelectedLegal Ops + ITDays 31-50Execution
First Pilot LaunchedPilot LeadDays 40-60Execution
Pilot ROI MeasuredLegal OpsDays 61-75Scaling
Board Presentation DeliveredGeneral CounselDays 75-85Scaling
Scaling Plan ApprovedAI Task ForceDays 80-90Scaling

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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