Guessing is not a strategy: How to build decision velocity with AI and real-time data
June 10, 2026 | Live Webinar
When the Inmates Run the Asylum
Doug is the author of the landmark book, Extreme Project Management®: Using Leadership, Principles and Tools to Deliver Value in the Face of Volatility. He works with clients who undertake projects in very demanding environments: those settings that feature high speed, high change, high unpredictability and high stress. Doug has lived in the trenches—from Bethlehem, Pennsylvania to Beijing, China—with over 275 project teams with budgets that ranged from $25,000 to over $25 million. He is one of the founders of the Agile Leadership Network, an organization dedicated to connecting, developing and supporting great project leaders. He is known for his hard-hitting and humorous keynote speeches that address vital issues facing today’s project-based organizations. You can visit Doug at www.dougdecarlo.com.
It's one thing for the inmates to be running the asylum. But it gets really interesting when nobody realizes that it's happening. The insanity I'm referring to involves a subtle juxtaposition of roles that can blindly take place between the project manager and the project's business owner.
To see what I'm getting at here, you need to be aware of the Four Business Questions of Extreme Project Management. The Four Business Questions form the framework around which the Flexible Project Model is built. The purpose of the Flexible Project Model, which operationalizes the four questions, is to structure the project so that the business owner receives perceptible value each step of the way, as well as to set it up so that the intended business benefits are ultimately realized after the project is over.
The Four Business Questions are:
1. Who needs what and why?
2. What will it take to do it?
3. Can we get what it takes?
4. Is it worth it?
Regarding the first question, it's the responsibility of the business owner to define what is needed out of the project, why it's important to have it and who the stakeholders are who will be expected to use and benefit from the project deliverable. Although the project manager and/or business analyst may use tools and techniques to help the business owner come up with answers, it's ultimately the business owner's "house" that …
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