Episode 440: The J Factor: Bringing Your Experience to Generative AI

Welcome to Episode 440 of the Microsoft Cloud IT Pro Podcast. Recorded live at the North American Cloud and Collaboration Summit in Branson, Missouri, this MS Cloud on the Road conversation has Ben sitting down with Jay Leask of Microsoft and Microsoft MVP Norm Young. Norm turns host and asks what their work looked like before generative AI: hand-written PowerShell, manual conditional access reviews, and deliverables that took two weeks instead of 45 minutes thanks to transcripts and Copilot Cowork skills.

From there it gets philosophical. They talk about whether your own experience (the “Ben factor” and the “J factor”) still shows up in AI-assisted work, why Ben feels some of the fun and creativity of the job slipping away while billing for faster work gets harder, and what automation means for people whose jobs cannot simply be reskilled. They close on whether models trained on AI-generated content will plateau or regress, whether the current spending pace can last, and why the sooner AI becomes just another feature, the better.

Show Notes

• North American Cloud and Collaboration Summit
• Copilot Cowork overview
• Use Copilot Cowork: Cowork skills
• Connect with Jay
• Jay Leask on LinkedIn
• Norm Young on Sessionize

Jay Leask

Jay Leask is a Principal AI Workforce Engineer at the Washington DC Microsoft Innovation Hub, where he works with customers on Microsoft 365, Copilot, and modern IT practices. He brings more than 25 years of IT experience, much of it with public sector organizations, and is a familiar voice at community events like the North American Cloud and Collaboration Summit.

Norm Young

Norm Young is a Microsoft MVP and solution architect who focuses on Microsoft 365 and the Power Platform, with a particular interest in Power Platform governance. Based in St. Catharines, Ontario, he is a regular community speaker and blogger on how Microsoft 365 and the Power Platform work better together.

Prior podcast context

• Ep 432: AI-Era Consulting Billing for Microsoft Cloud Delivery

• Ep 427: Copilot Cowork Hands-On Experiences

• Ep 417: Workplace Ninjas US, Zero Trust, and Conditional Access!

• Ep 410: Joy and Jay take over and talk Change Management

About the sponsors

Nasuni is a leading unstructured data platform for enterprises where file data is mission-critical for both people and AI. Nasuni powers the operational file layer where work happens — helping organizations manage, protect, and activate data so teams can work smarter, reduce costs, and operate securely without limits.

Intelligink designs, secures, and modernizes Microsoft 365 and Azure environments for organizations of every size, working alongside your internal IT team or MSP. From security audits and Copilot readiness to migrations and ongoing fractional cloud services, it’s the same production-tested advice Ben shares on the show, applied to your tenant. Book a conversation