In this episode of The Help Desk, host Kevin Coleman sits down with John Matthews, legendary Seattle-area IT veteran, former CIO at F5 Networks and ExtraHop, and longtime Microsoft leader, for a candid, no-BS conversation about the future of IT, AI, and internal services.
John pulls back the curtain on what it’s actually like to run technology at scale: why “all software kind of sucks,” why no one cares about the help desk until everything breaks, and why AI is both the most exciting and terrifying shift CIOs have faced in decades.
Drawing from decades of experience, he shares practical guidance on how leaders should approach AI, not as a hype-driven cost-cutting exercise, but as a tool to grow capacity, empower teams, and make work suck less.
You’ll hear John’s sharp takes on:
Why AI should be deployed first in low-stakes, high-impact operational workflows
The hidden power (and politics) of the help desk and ticketing systems
How CIOs can safely learn AI before rolling it out to revenue-critical teams
The “find it, fund it, fit it, fix it” framework for adopting new technology
Why automation should unlock growth—not just eliminate headcount
If you’re a CIO, IT leader, or operator navigating AI pressure from the board while still trying to keep the lights on, this episode is packed with hard-earned wisdom, practical advice, and refreshingly honest perspective.