PowerShell Wisdom from 35 Years in the Trenches with Jeff Hicks

With PowerShell + DevOps Global Summit 2026 opening this Monday, April 13th, this episode brings back one of the most respected names in the PowerShell community: Jeff Hicks. Andrew sits down with Jeff to dig into what makes the Summit special, the organic community that grew from those earliest events, and what it actually feels like to watch people go from struggling beginners to confident PowerShell practitioners. They also get into the big question hanging over everyone in IT right now: what does AI actually mean for the future of PowerShell professionals? Jeff shares his take on the "squishy bits" of scripting that AI still can't replicate, why learning the core PowerShell paradigm matters more than ever, and how he personally uses AI as a collaborator rather than a shortcut. It's a conversation about community, craft, and what it means to actually know your tools. 
 
Key Takeaways: 

• Learn the foundation first, tools second. Jeff's consistent message over decades of teaching: don't start with Azure commands or specific modules. Start with the PowerShell paradigm — objects, the pipeline, managing at scale — and the rest becomes much easier to pick up over time. 

• AI is a co-pilot, not a replacement. Jeff uses AI to get over specific technical hurdles, not to generate finished code. His concern isn't that AI will write bad scripts — it's that the next generation may skip the foundational learning that lets you recognize when AI gets it wrong. 

• The PowerShell community is genuinely welcoming, and showing up matters. Whether it's Summit, a local user group, or Discord, getting into rooms with other PowerShell people can be a career changer. The hallway conversations are half the value. 

 

Guest Bio: 
Jeff Hicks is a veteran IT professional with 35 years of experience, a long-time Microsoft MVP, and one of the most recognized voices in the PowerShell community. He's the author and co-author of several foundational PowerShell books, a Pluralsight course creator, and the publisher of the premium newsletter Behind the PowerShell Pipeline. He's been teaching and writing about PowerShell since the very beginning and continues to focus on the human side of scripting — the parts that go beyond syntax and into craft. 
 

Resource Links: 

• Jeff Hicks' hub (links to everything): https://jdhitsolutions.github.io 

• Behind the PowerShell Pipeline (newsletter & book on Leanpub): https://leanpub.com/behind-the-pspipeline 

• Jeff's Pluralsight courses: https://app.pluralsight.com/profile/author/jeff-hicks 

• Connect with Andrew: https://andrewpla.tech/links 

• PowerShell + DevOps Global Summit 2026 (April 13-16, Bellevue, WA): https://www.powershellsummit.org 

• PDQ Discord (PowerShell scripting channel): https://discord.gg/pdq 

• PowerShell Wednesday (weekly on PDQ's YouTube/Discord): https://www.youtube.com/watch?v=5vdfFswmREQ&list=PL1mL90yFExsix-L0havb8SbZXoYRPol0B&pp=0gcJCbcEOCosWNin 

• The PowerShell Podcast on YouTube: https://youtu.be/ceB-3QGbvBA