Welcome to the Department
This is your "pinned post" - TOLA edition.
You just watched me talk for ~20 minutes about RAG, MCP, agents, and a 12-year-old who called the future of HR AI "the Wikipedia of work." If you scanned the QR code, you're already here, so I'll spare you the bio you just sat through.
Here's what this place is:
The Department of First Things First is a weekly-ish newsletter for the people who actually have to make Workday work. Not analysts. Not buyers. Not the conference circuit. The people who go back to their desks on Monday and configure the business process, audit the security model, and explain to a CFO why the agent demo isn't shipping in their tenant by Q3.
The talk you just sat through is what this newsletter sounds like every week. Same voice. Same lens. Same anti-encyclopedia stance.
Applied to whatever the ecosystem is doing this week.
Here are five posts to tell you whether to subscribe:
1.
Workday Didn’t “Fix” Their UI. They Just Bought a $1 Billion Skin.
Jan 28
Justin came to me yesterday asking for $10 to buy a “skin” for his video game.
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.
April 27
I promised I’d share this during the talk. Workday rebranded their entire AI strategy in nine months. Again. Here's what's actually shipping under the Sana banner, what's still slideware, and why the Illuminate-to-Sana pivot doesn't change a thing about what you need to build in your tenant.
3.
The Moat is a Tollbooth: Why the AI Panic Around ERPs is Only Half Wrong
Feb 25
tldr; Josh Bersin published a piece today arguing the market is irrationally punishing enterprise software (like Workday) over AI fears.
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.
Put Down the Wrench: The Psychological Shift of Becoming a Solutions Architect
Feb 23
tldr; Transitioning from a Workday builder to an Architect isn’t about learning new modules. It’s a brutal psychological shift from fixing technical tickets to navigating corporate politics.
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.
Feb 9
We talk a lot about “User Adoption” in HR Tech.
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.