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Welcome to the Department. This is your "pinned post".
You just found The Department of First Things First. Maybe someone forwarded you a post. Maybe you caught me on Unsafe Harbor or Workday Gold. Maybe you Googled “why does Workday hate me” and ended up here.
Either way, welcome. Here’s the quick version of what this place is:
I’m Mike Domingo. I’ve been in HR technology for over twenty years. I’m currently a Sr. Manager of HR Technology at CVS Health. I co-organize the Philadelphia Workday RUG. I have a PMP, a DASM, and four Workday Pro certifications. I have opinions, and this is where I put them.
This newsletter is for the people who actually configure, architect, and maintain enterprise HR systems. Not the analysts. Not the buyers. Not the people who attend conferences and nod. The people who go back to their desks on Monday and have to make it work.
I publish weekly. No paywalls. No sponsors. No vendor cheerleading.
Here are five posts that will tell you whether this is your kind of place:
1.
My son Justin asked me for $10 to buy a cosmetic skin for his video game character. It didn’t make him faster or stronger. He just looked cool while falling off a cliff. Then Workday released their Sana-driven UI and I realized they’d done the exact same thing for a billion dollars. This post breaks down what the new UI actually means for practitioners, where the security nightmares hide, and why a search bar on top of a messy warehouse doesn’t clean the warehouse.
2.
Josh Bersin published a piece about AI “orchestration” that made it sound like the future was already here. I wrote the practitioner’s rebuttal. This one hit a nerve — 21,000 LinkedIn impressions, 233 reactions, 44 saves, and it doubled the newsletter’s subscriber count in a week. If you’ve ever sat in a meeting where an executive waved an analyst article at you and asked “why aren’t we doing this yet?” — this post is the answer you wished you had.
3.
Bersin argued that enterprise software is protected by a moat of decades-deep business rules. He’s right about the moat. But for the people actually using the system, that moat feels like a ten-lane tollbooth. This post introduced the framework I keep coming back to: the ERP isn’t going away. But the future is the ERP becoming headless infrastructure, buried so deep under experience layers and AI agents that the end-user forgets it exists.
4.
The hardest part of moving from Workday analyst to architect isn’t learning a new module. It’s the psychological shift from fixing tickets to navigating politics. I break down what that transition actually feels like: the muscle memory trap, the instant gratification desert, and why the Kitchen Table Test (can you explain your architecture to an 11-year-old?) is the only metric that matters.
5.
I Let My 11-Year-Old Audit Workday’s UI. He Lasted 3 Minutes.
I handed my son Justin a Workday tenant and asked him to request a day off. He’s a digital native who can navigate any app in seconds. He lasted three minutes before giving up. If a kid who grew up with an iPad needs a Quick Reference Guide to use your system, your design is broken. This post is the one that makes non-technical leaders finally understand the UX problem.
If any of those landed, you’re in the right place. Subscribe and I’ll show up in your inbox weekly with architecture takes, vendor accountability, and the occasional story about my son accidentally explaining enterprise strategy better than a $50,000 consultant.
— Mike
Director HR Tech | Keeper of the Layer Cake
P.S. If you want to hear me talk instead of read me type, I’ve been a guest on:
Talent Experience Live with Devin Foster at Phenom — “Speed Meets Experience” (to be published)
Unsafe Harbor with Christian Delcid — Episode 14
Workday Gold with Keith Bitikofer — December 19th, 2025
All are worth your commute.