Overview
Most AI rollouts fail not because of the technology, but because of the implementation. This checklist covers the five phases of successful AI adoption, based on what we've seen work across dozens of enterprise implementations.
15%
Typical adoption rate (poor rollout)
70%
Achievable adoption rate
90
Days to sustainable adoption
The Key Insight
Don't train people on "how to use AI." Train them on "how to do this specific task faster with AI." The specificity is what drives adoption.
1
Assessment
Week 1
- Identify 3-5 high-pain workflows that consume significant time
- Estimate current hours spent on each workflow per week/month
- Rank workflows by: frequency × time × pain level
- Select ONE workflow to start (resist the urge to do more)
- Identify 2-3 early adopters who are naturally curious about AI
- Document the current process in detail (you'll need this for training)
2
Tool Selection
Weeks 1-2
- Evaluate Claude and ChatGPT for your specific use case
- Review security certifications and data handling policies
- Confirm enterprise features: SSO, admin controls, usage analytics
- Verify data is not used for training (if required)
- Get IT/security approval
- Set up accounts for pilot group
- Document approved use cases and any restrictions
3
Pilot
Weeks 2-4
- Train early adopters on the specific workflow (not generic AI skills)
- Create step-by-step recipes with exact prompts to copy/paste
- Schedule daily 10-minute check-ins to troubleshoot issues
- Document time savings and quality outcomes
- Refine prompts based on what actually works
- Build a shared prompt library for the workflow
- Collect feedback on friction points
- Adjust the workflow based on real-world usage
4
Team Rollout
Weeks 4-6
- Share pilot results with the broader team (specific numbers)
- Have early adopters demo their workflows live
- Train the full team using refined materials from pilot
- Pair each new user with an early adopter as a buddy
- Set clear expectations: this is the new standard process
- Schedule weekly office hours for troubleshooting
- Create a Slack channel or Teams group for AI tips and questions
5
Optimization
Weeks 6-12
- Track adoption metrics weekly
- Address blockers immediately (within 24-48 hours)
- Add the second workflow once the first is habitual
- Celebrate and share wins publicly (all-hands, Slack, etc.)
- Build AI into standard operating procedures
- Update onboarding materials for new hires
- Measure and report ROI to leadership
- Identify next workflows to implement
Metrics to Track
Adoption Rate
Active users ÷ licensed users (target: 60%+)
Time Savings
Hours saved per workflow per week
Task Completion Time
Before/after comparison on target tasks
Quality Metrics
Error rates, revision cycles, stakeholder satisfaction
Common Mistakes to Avoid
- ✗ Training everyone at once before proving the concept
- ✗ Teaching generic AI skills instead of specific workflows
- ✗ No follow-up after initial training
- ✗ Measuring queries instead of outcomes
- ✗ Making AI optional instead of the default
- ✗ Ignoring middle managers (they determine actual adoption)
Need Help With Your Rollout?
Book a free AI Workflow Audit. We'll assess your current state, identify the highest-impact opportunities, and help you build a rollout plan that actually drives adoption.
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