40 years of IT leadership,
distilled for the seat you're aiming at.
Five eras of technology — mainframe to client-server, the first web wave, the outsourcing cycles, cloud, and now AI. Six CIO seats. One program built so the next generation doesn't have to learn the expensive lessons the expensive way.
"I've spent 40 years leading technology — from the data center floor to the boardroom. This program exists so the next generation of CIOs doesn't have to learn the expensive lessons the expensive way."
Three seats. Three moments in a CIO career.
VPs and senior directors one move from the CIO seat
You're the internal candidate. Sharpen the executive presence and vocabulary that separate 'ready' from 'chosen'.
New CIOs in the first 18 months
The window when patterns get set — good or bad. Compress the learning curve without the public tuition.
Specialty healthcare and dental support organizations
Complex clinical/operational realities, PE pressure, and consolidation. A peer who has actually sat in those seats.
Pick the format that matches the seat.
Private, direct, six months.
- · 12 bi-weekly 60-minute working sessions
- · Async access between sessions (email + short-form review)
- · Two anytime "hot-seat" crisis calls
- · Capped at 6 concurrent mentees to protect depth
A curated peer table with sharp elbows and Chatham House rules.
- · 8 CIOs, non-competing organizations
- · Six months, monthly 2-hour sessions
- · 1 hour taught · 1 hour peer case clinic
- · What's said in the Circle stays in the Circle
Six modules. Every one produces something you keep.
No slideware graveyards. Every module ends with a keepable artifact — a board narrative template, AI governance one-pager, incident command card, 90-day plan — that lives on your laptop after the program ends.
First 90 Days & the Operating Rhythm
Establish credibility, cadence, and the operating system the org will judge you by. Artifact: 90-day plan.
Board & CEO Fluency
Speak in outcomes, not tickets. Own the narrative before someone else writes it. Artifact: board narrative template.
AI from Slideware to P&L
Move from demos to durable value. Governance that ships, not stalls. Artifact: AI governance one-pager.
Security as an Executive Discipline
Frame risk in dollars and reputational surface, not CVEs. Artifact: incident command card.
Talent, Turnover & the Bench
Build the team the strategy actually needs — and the succession no one will thank you for building.
The CIO's Own Career
Search, negotiation, board seats, the next chapter. The part nobody teaches CIOs.
Limited seats.
Pricing shared on application.
Applications are read personally. If there's a mutual fit, I'll come back to you with cohort dates, pricing, and next steps.
Apply to the founding cohort.
A few honest paragraphs beats a polished CV. Tell me the seat you're in, the challenge you're wrestling with, and what a successful six months would actually look like.