The PowerShell Podcast

In this episode of The PowerShell Podcast, Andrew Pla is joined by Tara, a longtime IT professional who has officially started her PowerShell learning journey. Tara shares her honest experience transitioning from a GUI-first mindset to learning PowerShell fundamentals, including objects, verb-noun commands, variables, pipelines, and error messages. The conversation captures the real emotions of learning something new later in a career—confusion, frustration, breakthroughs, and growing confidence.

The episode also explores learning strategies like daily practice, flashcards, typing commands instead of copying, and asking “beginner” questions without fear. Andrew and Tara emphasize the importance of community, mentorship, growth mindset, and psychological safety, encouraging listeners that learning PowerShell doesn’t require perfection—just consistency, curiosity, and support.

Key Takeaways:

Learning PowerShell deepens your understanding of IT as a whole, not just scripting, especially through concepts like objects, properties, and methods.

Consistency beats intensity — small daily practice, repetition, and typing commands manually build real confidence over time.

Community changes everything — asking questions, sharing struggles, and learning publicly makes progress faster and far more enjoyable.

Guest Bio:
Tara Sinquefield is an experienced IT professional and PDQ team member who is publicly documenting her PowerShell learning journey. Known for her honesty, curiosity, and willingness to ask the questions others may be afraid to ask, Tara represents the many IT pros who are discovering PowerShell later in their careers. Her journey highlights how learning fundamentals can unlock deeper technical understanding, confidence, and new opportunities. She is also a host of PDQ Live every week

Resource Links:
PDQ Discord – https://discord.gg/PDQ
Tara's LinkedIn - https://www.linkedin.com/in/tara-sinquefield-894a1a215/
Connect with Andrew - https://andrewpla.tech/links
Tara Writes Her First Script: https://www.youtube.com/watch?v=Oa0GYX9_vj8
PowerShell Conference Europe – https://psconf.eu
PowerShell + DevOps Global Summit – https://powershellsummit.org
The PowerShell Podcast on YouTube: https://youtu.be/ZaPoS4mGW7s

Microsoft MVP Harm Veenstra, creator of PowerShellIsFun.com, joins The PowerShell Podcast to talk about productivity, consistency, and why PowerShell really is fun. Harm shares how blogging regularly helped accelerate his learning, improve his workflow, and deepen his connection to the community. He also discusses his recent transition to macOS, how he uses PowerShell across Mac, Linux, and Windows, and why modern PowerShell is far more cross-platform than many people realize.
The conversation dives into VS Code extensions, GitHub Codespaces, WSL, Nerdfonts, and practical terminal setups, along with honest thoughts on AI-generated scripts, learning the hard way, and why asking questions publicly is one of the fastest paths to growth.

Key Takeaways:

Consistency beats perfection – Having a repeatable workflow for writing, scripting, or learning makes long-term progress almost automatic.

PowerShell is truly cross-platform – Running PowerShell on macOS, Linux, WSL, and containers unlocks powerful workflows beyond Windows-only thinking.

Community accelerates everything – Asking questions, sharing small discoveries, and contributing publicly leads to faster learning, confidence, and career growth.

Guest Bio:
Harm Veenstra is a Microsoft MVP, consultant, blogger, and community contributor best known for PowerShellIsFun.com, where he publishes frequent, practical PowerShell content. He is an active participant in the PowerShell community and a regular conference attendee and speaker.

Resource Links:

PowerShell Is Fun – https://powershellisfun.com

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

Install Nerdfonts with PowerShell – https://powershellisfun.com/2026/01/30/install-nerdfonts-using-powershell/

GitHub Codespaces – https://github.com/features/codespaces

PowerShell Conference Europe – https://psconf.eu

PDQ Discord – https://discord.gg/PDQ

Fred's Module Building PS Wednesday – https://www.youtube.com/watch?v=ZAjtbZktL8w

The PowerShell Podcast on YouTube: https://youtu.be/V6kWnmrHOms

Recently retired PowerShell icon Don Jones joins The PowerShell Podcast for a wide-ranging conversation on career ownership, community leadership, and building a life that aligns with what you actually value. Don reflects on the difference between your job and your career, why investing in yourself pays off, and how asking better questions can change the way you influence decisions at work. The episode also dives into Don’s journey as a fiction author, his role in shaping the PowerShell community and Summit culture, and why real success comes from clarity, kindness, and helping others win.
 
Key Takeaways:
• Your employer owns your job, but you own your career—define your destination and build the skills to get there.
• Strong careers are built on outcomes, not tools—focus on saving time, reducing errors, and delivering measurable business value.
• Community scales when you empower others—create space for people to contribute, own wins, and multiply the impact beyond yourself.
 
Guest Bio:
Don Jones is a foundational figure in the PowerShell community, known for his decades of teaching, writing, and advocacy for automation and professional growth. A former Microsoft MVP, Don co-authored the widely influential Learn PowerShell in a Month of Lunches series and helped shape community culture through conferences, mentorship, and leadership. Now retired from full-time work, Don continues writing and publishing fiction, bringing the same clarity and craft to storytelling that made his technical teaching so impactful.
 
Resource Links:
• Don Jones Website and Books – https://donjones.com
Andrew's links: https://andrewpla.tech/links

• PowerShell + DevOps Global Summit – https://powershellsummit.org
• Tech Impact (nonprofit mentioned) – https://techimpact.org
• PowerShell.org – https://powershell.org
• PDQ Discord – https://discord.gg/PDQ
• PowerShell Wednesdays – https://www.youtube.com/results?search_query=PowerShell+Wednesdays

The PowerShell Podcast on YouTube: https://youtu.be/xKh8rqCqMQg

Principal Security Consultant and community favorite Jake Hildreth returns to The PowerShell Podcast to talk about building smarter automation, leveling up through community, and creating tools that solve real problems. Andrew shares his “stop trying so hard” theme for the year, how working smarter applies directly to scripting and security, and why getting involved with others is one of the fastest ways to grow in your career.

The conversation dives into Jake’s recent projects including Deck, a Markdown-to-terminal presentation tool built on Spectre.Console, and Stepper, a resumable scripting framework designed for long-running workflows that can’t be fully automated end-to-end. They also explore presentation skills, avoiding “death by PowerPoint,” and why security work requires constantly re-checking assumptions as threats evolve.
 
Key Takeaways:
• Work smarter, not harder — Whether you’re scripting or building a career, small sustainable improvements beat grinding yourself into a corner.
• Resumable automation is a game changer — Stepper helps scripts safely pause and resume, making real-world workflows more reliable when humans or flaky APIs are part of the loop.
• Community turns into real momentum — Contributing, asking questions, and sharing feedback builds skills, friendships, and opportunities faster than trying to learn alone.
 
Guest Bio:
Jake Hildreth is a Principal Security Consultant at Semperis, Microsoft MVP, and longtime builder of tools that make identity security suck a little less. With nearly 25 years in IT (and the battle scars to prove it), he specializes in helping orgs secure Active Directory and survive the baroque disaster that is Active Directory Certificate Services. He’s the creator of Locksmith, Stepper, Deck, BlueTuxedo, and PowerPUG!, open-source tools built to make life easier for overworked identity admins. When he’s not untangling Kerberos or wrangling DNS, he’s usually hanging out with his favorite people and most grounding reality check: his wife and daughter.
 
Resource Links:
• Jake Hildreth’s Website – https://jakehildreth.com
• Jake's GitHub - https://github.com/jakehildreth

Andrew's Links - https://andrewpla.tech/links

• PowerShell Spectre Console – https://pwshspectreconsole.com/
• PDQ Discord – https://discord.gg/PDQ
• PowerShell Conference Europe – https://psconf.eu
• PowerShell + DevOps Global Summit – https://powershellsummit.org
• Jake's PowerShell Wednesday – https://www.youtube.com/watch?v=YdV6Qecn9v0
The PowerShell Podcast on YouTube: https://youtu.be/rFeoTKLerkA

Newly minted Microsoft MVP David Sass joins The PowerShell Podcast to talk about PowerShell notebooks, terminal tooling, and making automation approachable for teams that are hesitant to touch the console. David shares how he uses Jupyter/PowerShell notebooks as a practical “click-to-run” interface for colleagues, helping them safely run approved automation while keeping the logic documented, repeatable, and under source control.

The conversation also dives into incident response automation, David’s journey from SharePoint engineering into security, and the surprising ways PowerShell can be used across Windows, cloud, and even Raspberry Pi lab clusters—while still staying focused on knowledge-sharing and building systems that don’t depend on one person.
 
Key Takeaways:
• Notebooks can remove friction for teams — combining documentation, code, and saved output creates a safer way for others to run automation without needing deep PowerShell confidence.
• PowerShell scales incident response workflows — David explains how notebooks can log in, pull incidents, enrich data, and even auto-close noise, reducing UI-click fatigue for analysts.
• Teaching makes you promotable — sharing knowledge reduces dependency on you, strengthens the team, and makes it easier for a business to grow your role without risk.
 
Guest Bio:
David is a Microsoft MVP and highly skilled SharePoint Guy who is focusing on Automation, Compliance, Security, Operational Excellence, Quality Assurance and hacking the unexpected out from the technology stack.
 
Resource Links:

David’s link hub – https://davidsass.io/

Andrew's links - https://andrewpla.tech/links

PowerShell Spectre Console – https://pwshspectreconsole.com/

PowerShell Wednesdays – https://www.youtube.com/results?search_query=PowerShell+Wednesdays

PDQ Discord – https://discord.gg/PDQ

ClockworkPi (the handheld device shown/discussed) – https://clockworkpi.com

The PowerShell Podcast on YouTube: https://youtu.be/Y03EJYpZczo