Table of contents
About this episode
Plenty of companies buy AI and then wonder why the return never shows up. Stephen Rose, Chief Technology Officer at Envision Technology Advisors, has a blunt answer: they skipped the prep. Fifteen years of duplicate files, no change management, and no acceptable use policy will sink a rollout faster than any limitation in the model.
His fix starts before any tool goes live. Clear out redundant and outdated content, define what success and ROI look like before you buy anything, and put an acceptable use policy in place. AI is only as good as the data and the guardrails you give it.
Then there are the people. In any change, Stephen sees about 15 percent who wanted it yesterday, 15 percent who will fight it forever, and 70 percent in the middle who decide whether the whole thing works. That middle group is where leaders should spend their energy.
“To move one person in that negative column, you’re going to spend so much effort and really not get much reward from it.”
Stephen and Matt Peters also dig into why so many AI projects are being paused or killed right now, and often it’s the bill, not the model. Token spend is becoming the new runaway cloud bill, and a single agent can rack up tens of thousands of dollars. Stephen’s advice is practical: set limits, ask people how they’re actually using AI, and run a quick cost check after prompts, because the dashboards won’t always tell you.
Stephen brings an unusual path to the conversation. He graduated as a film and video major and went on to spend 15 years at Microsoft shaping how the world adopts new technology. He closes with how quickly AI adoption has really moved and where AI should and shouldn’t be used.
What you’ll learn in this episode
- Why most AI rollouts stall because of preparation, not the model
- Why you should clear out redundant and outdated content before turning on AI
- Why to define success, ROI, and acceptable use before buying any AI tool
- How to win over the 70 percent of people in the middle of any change
- Why token costs are becoming the new runaway cloud bill
- How to keep AI spending under control
- Where AI should and shouldn’t be used
About Stephen Rose
Stephen Rose is the Chief Technology Officer at Envision Technology Advisors, a Rhode Island managed services and technology firm focused on secure, future-ready workplaces across cybersecurity, cloud, managed services, and digital innovation.
He spent 15 years at Microsoft, most recently driving global IT pro readiness for Modern Work and Copilot, and worked on products including Windows, OneDrive, and Office. A three-time Microsoft MVP with more than three decades in technology, he advises organizations on AI adoption, change management, and cloud strategy, and speaks regularly at industry events like TechCon365.
Resources mentioned
- Azure cold storage
- Microsoft Purview sensitivity labels
- Harvey (AI for legal)
- TechCon365
- Envision Technology Advisors
- Connect with Stephen Rose on LinkedIn
About the host
Matt Peters is the CEO and Co-Founder of Fixify, where he’s redefining the IT help desk for the AI era. Before founding Fixify, he was Chief Product Officer at Expel and held senior leadership roles at FireEye and Mandiant, where he helped pioneer some of the earliest managed detection and response services.
