You've learned about AI tools, compliance, and technical concepts. Now it's time to implement. But where do you start? How do you get team buy-in? What if something goes wrong?
This roadmap breaks down AI implementation into manageable 30-day sprints. Follow this plan, and you'll go from zero to fully adopted AI tools in 90 days.
Discovery & Foundation
Audit, assess compliance, create policy, train team
Pilot Programs
Test with small groups, measure ROI, iterate
Scale & Optimize
Roll out to full team, monitor adoption, report results
Month 1: Discovery & Foundation
Goal: Understand current state, identify gaps, create policy, get team buy-in
Audit Current AI Tool Usage
Survey team: "Which AI tools are you using?"
Use Google Form or Slack poll. Ask: Tool name, use case, frequency, cost
Check browser extensions
Look for ChatGPT, Grammarly, Copilot, Notion AI extensions
Review expense reports
Find AI tool subscriptions (ChatGPT Plus, Superhuman, etc.)
Interview team leads
Ask: What's working? What's not? What do they need?
Create AI tool inventory
Spreadsheet with: Tool, Users, Cost, Compliance status, Risk level
💡 Use HAIEC for Automated Discovery
HAIEC's GitHub App automatically scans your repos for AI tool usage (OpenAI, Anthropic, Cohere, etc.), saving you hours of manual discovery.
Install HAIEC GitHub AppAssess Compliance Gaps
For each tool: Check BAA status, data location, training policy
Use the 3 critical questions from compliance guide
Identify high-risk tools (no BAA, processing PHI)
Flag tools that need immediate action
Create risk matrix (Critical/High/Medium/Low)
Prioritize which tools to address first
Present findings to legal/compliance
Get their input on risk assessment
Create AI Usage Policy
Draft policy covering: Approved tools, prohibited tools, data handling
Keep it simple (2-3 pages max)
Define approved tools list
Tools with BAA, SOC2, proper data handling
Define prohibited tools list
Free tiers, tools without BAA, high-risk tools
Get legal approval
Have legal review and sign off
Communicate & Train
Email team about new AI policy
Clear, friendly tone. Explain why it matters.
Conduct 30-minute training session
Cover: Approved tools, how to request new tools, compliance basics
Collect policy acknowledgments
Simple checkbox: "I've read and understand the AI policy"
Set up ongoing monitoring
Monthly check-ins, quarterly audits
Month 2: Pilot Programs
Goal: Test AI tools with small groups, measure ROI, iterate based on feedback
Pilot #1: Code Assistant
Select 5 developers (mix of senior/junior)
Choose enthusiastic early adopters
Set up GitHub Copilot Business
$19/user/month, BAA available, compliant
Train on usage (1-hour session)
Show best practices, common prompts, shortcuts
Measure: PR velocity, code quality, satisfaction
Track metrics before and after
💡 HAIEC Integration
HAIEC automatically monitors GitHub Copilot usage for compliance issues, generating audit-ready reports for SOC2/HIPAA. No manual tracking needed.
Pilot #2: Meeting Assistant
Select 3 teams (15-20 people)
Different departments for diverse feedback
Set up Otter.ai Business (if healthcare) or Fireflies.ai
$10/user/month, auto-transcription
Train on note-taking workflow
Show how to review, edit, share transcripts
Measure: Time saved, action item completion, satisfaction
Survey after 2 weeks
Month 2 Review
Analyze pilot results
Review metrics, feedback, issues
Survey participants (5-minute survey)
What worked? What didn't? What do they need?
Calculate ROI
Time saved × hourly rate = value generated
Decide: Roll out or iterate
If ROI > 2x, proceed. If not, adjust and re-pilot.
Month 3: Scale & Optimize
Goal: Roll out to full team, monitor adoption, measure productivity gains, report results
Full Rollout
Roll out approved tools to full team
Phased rollout: 25% → 50% → 100% over 2 weeks
Provide training resources
Video tutorials, documentation, office hours
Set up support channel (#ai-help in Slack)
Dedicated channel for questions, issues, tips
Monitor adoption rate
Track: % of team using tools, frequency, satisfaction
Optimize & Measure
Review usage analytics
Which tools are most used? Which are ignored?
Identify power users (learn from them)
Interview top users, document best practices
Identify non-users (provide extra training)
1-on-1 sessions, pair with power users
Measure productivity gains
Time saved, output increased, quality improved
Report results to leadership
ROI, adoption rate, productivity gains, next steps
Success Metrics
Target Metrics (Month 3)
How to Measure
Adoption Rate
Track: % of team with active accounts, weekly active users
Productivity
Track: Time saved (surveys), output increased (metrics), quality (reviews)
Compliance
Track: Violations detected, audit findings, BAA coverage
ROI
Calculate: (Time saved × hourly rate) / tool cost
Budget Planning
Example budget for 50-person team:
GitHub Copilot Business
20 developers × $19/month
$380/mo
Otter.ai Business
30 people × $10/month
$300/mo
Notion AI
50 people × $10/month
$500/mo
Training & Support
One-time + ongoing
$1,000
Total First Year Cost
Monthly: $1,180 × 12 = $14,160 + $1,000 setup
$15,160
Expected ROI
Time saved: 8-12 hours/week × 50 people = 400-600 hours/week
Value: 500 hours/week × $50/hour × 52 weeks = $1,300,000/year
ROI: 85x investment
Common Mistakes to Avoid
❌ Buying tools before defining use cases
✅ Fix: Start with problems, not tools. What are you trying to solve?
❌ Ignoring compliance until too late
✅ Fix: Check BAA, data location, training policy BEFORE purchasing
❌ No training provided
✅ Fix: Invest in training. Tools are useless if people don't know how to use them.
❌ Trusting AI 100%
✅ Fix: Always review AI output. AI makes mistakes. You're responsible.
❌ Not measuring ROI
✅ Fix: Track metrics from day 1. If you can't measure it, you can't improve it.
❌ Rolling out to everyone at once
✅ Fix: Start with pilots. Learn, iterate, then scale.
Ready to Start Your 90-Day Journey?
Follow this roadmap, and you'll go from zero to fully adopted AI tools in 90 days. Start with Month 1, Week 1 today.
Related Resources
AI Program Management Framework (CSM6)
A structured approach to AI governance. Free interactive checklist, templates, and step-by-step guide for project managers.
Download: Complete 30/60/90 Day Implementation Checklist
Week-by-week action items, budget templates, and success metrics. Everything you need to implement AI tools successfully.
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