The PowerShell Podcast

In this episode, host Andrew Pla sits down with Mark Littlefield, VP of Product at PDQ, for a wide-ranging conversation about product management, the PowerShell community, and what it looks like to deeply learn a technical domain when you're not coming from a traditional sysadmin background. Mark shares his journey from tech support to product management, what drew him to PDQ and the challenges facing IT admins, and what surprised him about PowerShell once he started paying close attention. The two also dig into the history behind PDQ Connect's PowerShell Scanner, how product teams learn from customers, the art of storytelling as a PM and sysadmin skill, and more.

Key Takeaways:

Product management and PowerShell automation share a core philosophy: solve problems at the root, not just on the surface. Whether you're writing a script or building a feature, the goal is to eliminate a challenge entirely rather than patch around it.

Understanding your customer requires more than data — it requires immersion. Mark describes going deep into the sysadmin world through customer interviews, internal usage, and community engagement to truly understand the problems facing IT teams.

Great storytelling is a transferable skill. Andrew draws a parallel between how Jeffrey Snover used the Monad Manifesto to get internal buy-in at Microsoft and how to use narrative to align teams and push ideas forward.

Guest Bio:
Mark Littlefield is the VP of Product at PDQ, where he leads product strategy and development for PDQ Connect and the broader PDQ product suite. With over 15 years of product management experience, Mark previously served as VP of Product Management at InsideSales.com, where he oversaw product management and design across the platform. He holds a Bachelor of Science in Information Systems with a focus on Business Intelligence from Utah Valley University and is based in Salt Lake City, Utah.

Resource Links:
PowerShell Event: https://www.pdq.com/save-time-with-powershell-pdq-connect/
PDQ Connect: https://www.pdq.com/pdq-connect/
PDQ PowerShell Scanners GitHub repository: https://github.com/pdqcom/PowerShell-Scanners
The Monad Manifesto (Microsoft Learn): https://learn.microsoft.com/en-us/powershell/scripting/developer/monad-manifesto?view=powershell-7.5
Monad Manifesto blog post by Jeffrey Snover: https://devblogs.microsoft.com/powershell/monad-manifesto-the-origin-of-windows-powershell/
Mark Littlefield on LinkedIn: https://www.linkedin.com/in/mark-littlefield/
Connect with Andrew: https://andrewpla.tech/links
PDQ Discord: https://discord.gg/pdq
The PowerShell Podcast on YouTube: https://youtu.be/fo2V5LC-EZo

It's PowerShell After Dark. Recorded live at the PowerShell & DevOps Global Summit in Bellevue, Washington, host Andrew Pla takes his mic to the hotel bar for a series of candid conversations with attendees. The episode features four guests: Josh Gratton, an OnRamp scholarship recipient whose career pivot to junior systems engineer was fueled by PowerShell and the podcast; Mark Go, a first-time Summit speaker and attendee; Craig Mileham, a fellow podcast listener and Summit first-timer working in higher ed IT; and Matt Zaske, a longtime community member, conference speaker, and IoT enthusiast who ran a Home Assistant lightning demo. What connects all four conversations is the same thread Andrew keeps pulling on: community makes everything better. Beginners belong here. Reach out. Take the risk. Start now.

Key Takeaways:

The OnRamp scholarship program is genuinely life-changing for early-career IT professionals. Josh Gratton's story, from service desk to systems engineer to Summit attendee, is a direct line from PowerShell to career transformation, and it started with applying for a scholarship he poured his heart into.

Showing up in person changes something. Every guest in this episode described the in-real-life version of the PowerShell community as warmer, more welcoming, and more accessible than they expected. The gap between "online community" and "your people" closes fast when you're in the same room.

Reaching out is not just encouraged, it's the move. Andrew makes the case clearly: the people who message him, who post in Discord, who ask questions in public, those are the ones he sees succeed. Suffering in silence is optional. So is waiting.

Guest Bios:
Josh Gratton is an IT professional who made a mid-career pivot from 15 years in a different field to the service desk, then leveraged PowerShell automation to earn a promotion to his company's systems engineering team. A 2026 OnRamp scholarship recipient, Josh attended his first PowerShell & DevOps Global Summit in Bellevue and left planning to present at a future Summit and bring a colleague along next year.

Mark Go is an IT professional and active member of the PDQ Discord community who attended the 2026 PowerShell & DevOps Global Summit. He served as Andrew's cameraman during the Summit's After Dark session and is known in the community for his IoT work, including speaking at Summit. He's a returning podcast guest, Powershell Wednesday and Summit speaker. Mark brings a hardware-forward perspective to PowerShell, with interests in soldering and embedded systems.

Craig Mileham is a PowerShell Podcast listener and Summit first-timer who works for an MSP in the higher ed space. He attended this year's Summit to absorb as much as possible and left energized to build internal tools for his help desk team and share what he learned at PowerShell Wednesday. This guy is really awesome

Matt Zaske is an IT professional, conference speaker, and community member based in Minnesota. A regular presence at events like MMS, Matt is also an avid Home Assistant enthusiast who bridges the gap between PowerShell and IoT hardware. He ran a lightning demo at the 2026 Summit, taught attendees how to solder, and blogs regularly at mzonline.com. You can also find him on LinkedIn and Bluesky. 3d printing legend. GET ON HIS LEVEL

Resource Links:

PowerShell & DevOps Global Summit: https://www.powershellsummit.org

OnRamp Program and Scholarship: https://www.powershellsummit.org/on-ramp/

The PowerShell Podcast on PDQ.com: https://www.pdq.com/resources/the-powershell-podcast/

PDQ Discord (Learn PowerShell channel): https://discord.gg/PDQ

PDQ Careers: https://www.pdq.com/jobs/

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

Matt Zaske's Blog: https://www.mzonline.com

The PowerShell Podcast on YouTube: https://youtu.be/Y_GDB0e8xHY

Jess Pomfret returns for her third appearance on the PowerShell Podcast and brings the same energy that keeps people coming back. She and Andrew cover a lot of ground, starting with her upcoming "Chase the Sun" charity cycling event where she'll attempt to ride 205 miles coast-to-coast across the UK in a single day, starting at sunrise on the longest day of the year and racing the sun to the finish line. It's a big undertaking, and she's riding to raise money for Momentum in Fitness, a charity her wife works for that brings fitness opportunities to older adults, kids in non-traditional school settings, and children with cancer.

On the technical side, Jess makes the case for PowerShell splatting as an underrated beginner concept that makes code dramatically more readable. She walks through the idea of pulling parameters out of a long command line, organizing them into a hash table, and passing that hash table to the command instead. It's one of those things experienced scripters take for granted, but seeing it for the first time is genuinely useful.

The conversation also gets into Desired State Configuration (DSC), where Andrew and Jess dig into what it is, how it works, and why it matters for sysadmins who want to maintain consistent configuration across their environments. Jess also opens up about managing a packed schedule between her day job, speaking, podcasting, LinkedIn Learning courses, and serious bike training. Her answer is honest and relatable: she's still figuring it out, but Todoist and a very supportive partner help a lot.

Key Takeaways:

Splatting is one of the most readable improvements you can make to your PowerShell code. Instead of chaining parameters into one long command, you load them into a hash table and pass that to your command with an @ symbol. Cleaner to write, easier to read, and especially useful when you're sharing code on a screen.

DSC lets you define what a system should look like and PowerShell handles the work of getting it (and keeping it) there. It's a mindset shift from scripting manual steps to declaring an end state, and it's particularly powerful in large environments where consistency matters.

Having a support system is one of the most underrated factors in being able to sustain a high-output career alongside community contributions. Whether it's people around you who help carry the load or finding your people in the data and PowerShell communities, you can't do it alone indefinitely.

Guest Bio:
Jess Pomfret is a Data Platform Engineer and a dual Microsoft MVP. She's been working with SQL Server since 2011, is a maintainer on the dbatools open source project, co-host of the Finding Data Friends podcast, and a LinkedIn Learning instructor. She grew up in the south-west of England and now lives in the US. Outside of tech, she's an avid cyclist, padel player, and a devoted fan of proper football.
 
Resource Links:

Connect with Jess on LinkedIn: https://www.linkedin.com/in/jpomfret

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

Jess's blog: https://jesspomfret.com

Support Jess's Chase the Sun ride for Momentum in Fitness: https://www.justgiving.com/page/jess-pomfret

Finding Data Friends podcast on YouTube: https://www.youtube.com/@findingdatafriends/videos

dbatools – PowerShell module for SQL Server automation: https://dbatools.io

Jess's previous episode on the PowerShell Podcast (Ep. 164): https://powershellpodcast.podbean.com/e/from-proper-football-to-databases-with-jess-pomfret/

Jess's first appearance on the PowerShell Podcast: https://powershellpodcast.podbean.com/e/dbatools-with-jess-pomfret/

Join the PDQ Discord: https://discord.gg/pdq

The PowerShell Podcast on YouTube: https://youtu.be/M2XvvCKs1Ls

Paula Kingsley, a senior IT leader, longtime consultant, automation and PowerShell enthusiast, eight-time Microsoft MVP for Exchange Server, and happy generalist, joins Andrew for a wide-ranging conversation about her tech journey and what it actually looks like to grow from deep hands-on work into technology leadership. They kick things off with a topic near and dear to a lot of PowerShell folks: the ISE-to-VS Code migration. Paula was terrified of it, put it off for as long as she could, and now uses VS Code every single day.

From there, the conversation opens up into what consulting taught her about solving problems, how being a generalist can be a genuine advantage, why documentation and communication matter as much as technical skill, and what it means to keep the human side of technology alive as you move up. Paula also drops some solid practical PowerShell wisdom along the way, from always including WhatIf support in your functions to the very important reminder that Get is safe and Set is something else entirely.

Key Takeaways:

Making the jump from ISE to VS Code feels daunting, but the move is absolutely worth it. The secret is forcing yourself to open it first and just leaving it open until the habit takes hold.

Being a generalist isn't a weakness. The ability to see across systems, communicate up and down, and translate technical work into business outcomes is a real and undervalued skill.

Always build yourself an escape route. WhatIf and ShouldProcess aren't just best practices, they're the difference between a confident deployment and a very bad afternoon.

Guest Bio:
Paula Kingsley is an outcome-driven senior IT leader, technology operations and engineering expert, eight-time Microsoft MVP for Exchange Server, and self-described happy generalist. Her path into tech started with a liberal arts degree and eventually led through boutique IT consulting, enterprise infrastructure, global production operations, automation, cloud, AI, and a deep appreciation for PowerShell. Paula has built her career around solving problems, simplifying workflows, removing friction, and helping technical teams work better at scale. She is senior enough to shape strategy and steer practices, still hands-on enough to fix things herself, and yes, she even likes regex. You can find her on GitHub as lanwench and on LinkedIn.

Resource Links:

Paula Kingsley on LinkedIn – https://www.linkedin.com/in/paulakingsley/

Paula Kingsley on GitHub – https://github.com/lanwench

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

PDQ Discord – https://discord.gg/pdq

The PowerShell Podcast on YouTube: https://youtu.be/WLNVCW7S8BE

This episode of the PowerShell Podcast After Dark captures two candid bar-session conversations from the PowerShell and DevOps Global Summit, centered on community, career growth, and the real-world value of putting yourself out there. In the first segment, Josh Dearing talks about attending his first Summit, building PowerShell modules, learning from failure, and using automation to improve systems and processes in higher education.

In the second, Jeff Wardlaw reflects on finally attending the event in person, the impact of meeting the people behind the tools and community, and the broader lessons around perspective, technical leadership, communication, and problem-solving. Across both conversations, the theme is clear, PowerShell is not just a toolset, it is a way into a generous technical community where curiosity, experimentation, and shared learning can meaningfully shape a career.

The PowerShell Podcast on YouTube: https://youtu.be/NyT_A1hSH_M