The CEO's First 90 Days of AI Adoption

You’ve decided to transform your company with AI. Now what? Here’s the concrete roadmap we used at Trilogy - broken into 90-day, 6-month, and 12-month milestones.

First 90 Days: Build the Foundation

Week 1-2: Set the tone.

• Talk about AI in every meeting. Every all-hands. Every 1:1.
• Sign up for enterprise AI tools yourself. Use them daily. Show your work.
• Announce that AI proficiency is now part of everyone’s job.

Week 3-4: Buy the tools.

• Enterprise ChatGPT and Claude subscriptions for every employee.
• GitHub Copilot for engineering teams.
• Don’t negotiate on this - the cost is trivial compared to the cost of delay.

Week 5-8: Launch weekly AI sessions.

• Block a recurring 5-hour slot: 4 hours building + 1 hour demos.
• Make attendance mandatory. Video on. No exceptions.
• Start with the base of Slowinski’s Pyramid: repetitive tasks.

Week 9-12: Set guardrails.

• Work with legal to establish data security policies for AI tools.
• Define what data can and cannot be shared with external AI services.
• Create acceptable use guidelines.
• These guardrails enable speed, not restrict it.

6 Months: Build Momentum

Quarterly hackathons. Expand beyond weekly sessions. Full-day events focused on specific business problems. Cross-functional teams. Prizes for impact.

Celebrate wins publicly. Every AI success story gets company-wide visibility. Make heroes out of early adopters. Create a wins channel. Share metrics.

Monitor usage rates. Check who’s using the tools and who isn’t. If someone isn’t logging into AI tools regularly, have a direct conversation. Find out if it’s resistance, confusion, or lack of relevant use cases.

Start building Second Brains. Begin with one team’s knowledge base. Create custom AI assistants that know your company’s context. Iterate over 30 days. Then expand.

12 Months: Lock It In

Deal with skeptics. The “wait and see” period is over. Everyone has had tools, training, time, and support. If someone still isn’t on board, have the direct conversation.

CEO at 10-25%. You should be spending this percentage of your time on AI evangelism, learning, and doing. Not delegating it. Doing it.

AI in hiring. Add AI proficiency to job descriptions and interview processes. New hires should already be AI-comfortable, or at minimum, AI-curious.

Board reporting. Present AI transformation metrics to the board. ROI, headcount efficiency, tool usage rates, customer impact. Make it concrete.

The Non-Negotiables

Throughout all 12 months:

• CEO participates personally (not delegates)
• AI time is mandatory (not optional)
• Real business problems (not exercises)
• Demos and accountability (not silent adoption)

This roadmap isn’t complicated. Execution is what separates the companies that transform from the ones that just talk about it.