Hey everyone! I figured we would deviate from our standard format a bit for this edition for the week of Aug. 17th. I had authored a whole section about my thoughts around the BlackHat conference and my (very good) experiences there, but when i sat back and looked at it, I felt like it didn’t flow well (that’s the perfectionist in me). As such, instead of leaving you with nothing until this following Thursday, I figured I’d curate some content for you from the Podcast.
As regular followers of the show will know, we run the whole list of SysAdmin topics for the show including:
Microsoft’s ecosytem (Especially Hyper-V)
M365 and Azure
Cybersecurity
Some Linux / Open Source stuff
Storage and Networking
And of course… soft skills
Soft skills are often overlooked when viewed with a list of other SysAdmin skills, but they are some of the most important skills in any SysAdmin’s toolbelt. They help you deal with the day-to-day and stay sane and they also help you communicate to a board room and provide customer service effectively as well.
As such, I tasked Claude with parsing the full episode list of the show (all 56 episodes across our back catalog of 15 months!) and had it curate a list of soft-skill episodes that we’ve covered throughout the lifespan of the show, thus far.
If you have a SysAdmin soft-skill topic you’d like to see us cover, do let us know in the comments below!
Here is the list!
Getting In
The on-ramp questions. Worth reading if you are early, or if you are the one doing the hiring and wondering why the pipeline looks the way it does.
Episode 005 - Microsoft Certification in 2025: A Microsoft Certified Trainer’s Take - Paul Schnackenburg is an MCT, so this is the view from inside the machine: the shift from product exams to role-based ones, why the exam names confuse everyone, what applied skills actually prove, and whether the annual renewal treadmill earns its place in your calendar. Useful if you are deciding where a training budget goes. NOTE: this one is a bit dated as far as certs go, but i still contains a TON of useful information for those navigating the Microsoft certification world.
Episode 027 - Is University Worth It for Aspiring SysAdmins? - Clay Tamam is a recent IT graduate in the Netherlands who was in his first SysAdmin role when we recorded, so this is not two veterans speculating about kids these days. Where the degree held up, where it did not, and how certifications and a homelab stack against it. Includes his first real outage, which for once was not DNS.
Episode 033 - Why IT Job Postings Are Completely Broken - Andy solo, scrolling through real postings: unicorn requirements, role creep, and job descriptions that read like four jobs stapled together. Not a recruiter dunk session. The argument is that a posting is a small glimpse into the organization doing the posting, most of them are posting confusion, and both sides can do better.
Episode 056 - How People Actually Get Into SysAdmin Work - Published this week, so it is the newest thing on this list. Andy and Eric Siron trade full origin stories, from a 486 and a VIC-20 through first paid jobs neither of them was qualified for, and land on the same first catastrophe: data gone, no idea if it was coming back. Closes on whether the cheap-hardware-and-time on-ramp that produced both of them still exists in 2026.
The Craft Nobody Tests You On
There is no exam objective for any of this, which is exactly why it separates people.
Episode 009 - What Makes a Great SysAdmin? - The one that started this whole thread for us. Andy and Paul pull apart the technical skills from the traits that actually make someone good at this work: communication over compiling, curiosity as the real fuel, and yes, empathy. Also gets into gatekeeping, and why the best people in this field never stop learning even when they badly want to.
Episode 015 - The Art of Troubleshooting in Tech - Change one thing at a time. That is the entire discipline, and almost nobody manages it at 2am with a queue backing up behind them. Scoping a problem without panicking, when to escalate, surviving vendor support roulette, and how to stop a junior tech from chaotic-clicking their way into a production outage.
Episode 022 - Why IT Documentation Matters (Even if You Hate Writing It) - Writing is a soft skill and this episode treats it like one. War stories where future you had to clean up past you’s mess, plus the honest question of what makes documentation stay alive instead of quietly rotting in a wiki nobody has opened since the last migration.
Getting Heard
Being right is not the job. Being right where someone with budget can hear you is the job.
Episode 014 - How SysAdmins Can Prove Their Value (Before the Next Layoff) - The Visibility Paradox: the better you are at this, the less anyone notices you exist. This one is about fixing that deliberately. Quantifying wins, turning automation into an ROI number somebody upstairs will repeat, and asking who is in the room before the meeting starts.
Episode 050 - How Do You Run a Blameless Incident Postmortem? - A postmortem that ends with a name instead of a root cause wasted everyone’s time in the room. Blameless without sliding into unaccountable, separating root cause from contributing factors, and why the follow-through is the entire point. The discipline scales from sixty people in a war room down to you writing a summary for one nervous boss.
Episode 055 - How Do You Run IT With No Budget? - “No budget” is almost never no budget. It is no budget yet, and what closes the gap is your ability to attach a real dollar figure to the risk you are already carrying, because leadership does not act on fear but it does act on risk management. And if the answer is still no, get the decision in writing.
Staying in the Chair
The long game. Nobody warns you that lasting twenty years in this field is its own separate skill.
Episode 010 - Tips for Tech Conferences in 2025 - Conferences are expensive and most people get them wrong. The hallway track is worth more than the session schedule, the expo hall is not purely a capitalist trap, and speaking at an event is one of the better career moves available to you. Recorded while Andy was still fighting off the conference cold that proves he was there.
Episode 026 - Burnout in IT: Why So Many Tech Pros Are Struggling (and How to Cope) - The heaviest one we have recorded, and the one most worth forwarding to somebody. Imposter syndrome in a field that changes underneath you, always-on culture, notification overload, and what actually moves the needle: boundaries, peer support, and managers who build psychological safety rather than put it on a slide.
Episode 031 - How the IT Community Makes You a Better SysAdmin - Not the corporate version of the word. Mentors who turned up unannounced and changed a trajectory, MVP circles, open source projects that operate nothing like vendor ones, and the case that contributing small things builds a career faster than any credential on its own.
Episode 042 - Should SysAdmins Job Hop or Stay Put? - Four decades of combined experience arguing that the answer is neither one. Staying long term buys institutional depth, ownership, and skill calcification you will not notice happening. Hopping buys pay jumps, breadth, and a reputation you have to manage. Secret Option C is the actual episode.
Episode 053 - How to Survive as a Solo SysAdmin - A listener request. When you are the only person between a working business and total collapse, the job stops being about doing everything and starts being about deciding what not to do this week. Triage before projects, documentation as an insurance policy, buying time back through automation, and speaking business value instead of acronyms.
One Closing Note
Line these up and a pattern shows up that none of us planned.
Every single one of these episodes is about the same thing from a different angle: the gap between doing the work and being understood doing the work. Documentation is that gap in writing. The postmortem is that gap under pressure. The budget conversation is that gap with money attached. Burnout is what happens when the gap never closes and you keep absorbing the difference yourself.
The technical skills get you in the door. This is the set that decides how long you stay and what you get paid while you are there.
Stay Frosty,
Andy
SysAdmin Weekly
Bookmarked this one! Any advice on how to thrive at an MSP?