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The AI Transformation Guide.
The playbook 91% of C-Suites admit they’re faking. In 21 pages.
By Paul Cheek · MIT Sloan · AIDE Institute
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Inside the guide
A complete, self-serve 18-step transformation plan
Designed so any CEO of a 10–250 person organization can run it with their leadership team and board, no consultant required, with a step-to-step dependency map and full Gantt across 13 weeks plus ongoing loops.
A 12-week structured training program for every employee
Including the CEO — mapped to whichever AI ecosystem the org runs on (Anthropic, Microsoft Copilot, Google Gemini, or OpenAI/ChatGPT), with weekly modules, real-job experiments, reflection prompts, and Show & Tell rituals.
Ready-to-send templates for the political work
Board-approval email for the AI Use Policy, CFO budget memo, all-team kickoff announcement, baseline and end-of-program surveys, weekly training emails, office-hours intake, and Show & Tell agendas — drafted so leaders can adapt and send within days, not months.
Frameworks for the hard structural moves
The four non-negotiable CEO conditions, org chart audit and the Chief Node Officer concept, the AI Opportunities Workshop with its four evaluation characteristics (human-vs-AI, risk, business impact, feasibility), the systems audit feeding a central data repository, and the Living Wiki regenerated daily from source data.
Built-in measurement and a path beyond Loop 1
Baseline + resurvey using a single shared instrument, impact report outline for the board, monthly opportunity accountability reviews, CEO scheduled tasks as an "always-on internal consulting firm," and quarterly loops (Depth → Reach → Restructure) so the work compounds rather than stalls after the first 12 weeks.
of C-Suite execs admit faking AI knowledge
Median S&P 500 top-management AI literacy score
of today's Fortune 500 projected to vanish in 20 years
Source: AIDE Institute proprietary research, 2025.
“The risk is not that people using AI will replace your people. It’s the risk that your business will become obsolete because organizations that use AI will replace your organization.”
Paul Cheek— MIT Sloan · Author, No One Works Here
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About Paul Cheek
Paul Cheek is a global expert on AI-driven enterprises and enterprise innovation. He is a Senior Lecturer at the MIT Sloan School of Management and Senior Advisor for Entrepreneurship & Artificial Intelligence at the Martin Trust Center for MIT Entrepreneurship. As founder of the AI-Driven Enterprise Institute and Entonomy, he develops data systems and software that power AI agent-run businesses. A Forbes 30 Under 30 honoree, bestselling author of Disciplined Entrepreneurship: Startup Tactics, and recipient of MIT’s Monosson Prize for impact on entrepreneurship education, Paul has advised and built ventures from seed to scale, with his work featured in The Wall Street Journal, Bloomberg, and Forbes.
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AI strategy and AI-Driven Enterprise transformation advisory for C-Suite teams, boards, PE firms, and operating companies. Engagements range from board-level AI literacy workshops to multi-month or year-long AIDE transformation sprints.
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