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Roadmap

From AI-Curious to AI-Capable: A 90-Day Roadmap for Executives

Sequential, tangible milestones. Doubles as the outline for our intro-call conversation.

John Biske·April 2026·12 min read·For Executives

You don't need a transformation program. You need 90 days.

This roadmap is what I walk through on most intro calls. Every milestone is sized for a real executive's real calendar — not a dedicated project role — and every one produces a tangible artifact you can point at.

Days 1–30 — Grounding

The goal of this month is judgment, not output.
  1. 01Week 1: One hour of honest conversation about where AI actually fits in your role. Not hype-adjacent. Real work, real limits.
  2. 02Week 2: Pick one recurring task — the one you find yourself doing every Tuesday. Document what "good" looks like.
  3. 03Week 3: Try doing that task with AI assistance. Write down what was faster, what was worse, what surprised you.
  4. 04Week 4: Write a one-page note to yourself: "Where AI fits in my role, as of this month." Date it. You'll revise it often.

Days 31–60 — Building

Now you can make things. Not before.
  1. 01Week 5: Turn the Week-2 task into a Claude Project or Custom GPT. Yours. On your account.
  2. 02Week 6: Use it every time that task comes up. Keep a running list of where it fails.
  3. 03Week 7: Fix the top three failures by refining the prompt and adding examples.
  4. 04Week 8: Show it to one trusted colleague. Have them try to break it. Keep fixing.

Days 61–90 — Extending

This month is about proving it can spread.
  1. 01Week 9: Pick a second task, or a task from a colleague's role. Apply what you learned.
  2. 02Week 10: Write the first version of your personal AI operating principles — three to five rules you'd want everyone on your team to share.
  3. 03Week 11: Share the principles with your team. Have one conversation, not a presentation.
  4. 04Week 12: Decide what's next. Coaching, a team workshop, or a specific custom tool — or none of the above and you stay at this pace.
“Ninety days is enough to build real capability. Less is luck. More is a project.”

How coaching fits (if you want it)

Most executives do this roadmap with 4–6 coaching sessions spread across the 90 days — one at kickoff, one per milestone, one at the end. That's roughly $2,500–$3,500 depending on cadence, and it's the fastest way through the curve.

You can also do it alone. The roadmap is the roadmap. The value of coaching is speed, judgment shortcuts, and someone to show your drafts to who won't be polite about them.

Want to talk about where this fits for you?

Thirty minutes. No pitch, no slides. Tell me where your team is. I'll tell you honestly whether I can help.

Schedule Your Free Intro Call
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