The Sideways Door
An HR Technology origin story involving a temp job, a stack of time clocks, and conversational analytics in 2006.
tldr;
Nobody in this field chose it. We got matched to it, usually by a single keyword on a job posting.
Mine was SQL, in 2004. Within a couple of years I had upgraded an entire HRIS by myself, wired physical time clocks, and shipped plain-language HR analytics before the iPhone existed.
The sideways door isn’t random. It selects for exactly the people this work needs.
Also: the “revolutionary” conversational analytics your vendor demoed last quarter? I ran it in the mid-2000s. It was called EasyAsk. Hold that thought.
Reply with your origin story. I read every one.
In 2004 I was a temp.
SQL work for an e-discovery client. Paid the bills. Zero long-term plan, because I was in my twenties and the long-term plan was “keep having a job.”
Then I saw a posting. Somebody wanted strong SQL skills for something called an HRIS Specialist role.
I want to be honest about the decision process here. I did not feel a calling toward human resources technology. I did not have a vision of enterprise systems. I went to college for finance. I recognized one keyword. I applied because the ad said SQL and I spoke SQL. That’s the whole story. That’s everyone’s whole story.
I got the job (mainly because at the time, I was volunteering on a Linux project called MythTV and shipping code, and of course, SQL). And then the job got interesting.
Purple squirrel, first rodeo
If you’ve been in this field a while you know the term “purple squirrel”: the candidate who impossibly matches every requirement at once. Recruiters hunt them for years and never find one.
Here’s what nobody tells you: purple squirrels aren’t found. They’re manufactured, on the job, by small teams with big systems and no budget for specialists. You don’t match every requirement. You become every requirement, one emergency at a time.
At that first HRIS job I ended up doing everything, because there was nobody else to do it. I upgraded the HRIS itself (Personnel Data Systems) from an aging Windows 95 application to their web-based platform. Alone. Integrations included (lots of DTS and stored procedure work). I wired up Kronos time clocks, and I mean physically wired, as in “why is the HRIS guy holding a drill.”
And now the part that’s going to sound made up: I shipped conversational HR analytics before the iPhone existed.
I stood up an analytics package that let regular humans ask HR analytics questions in “plain language”. Type “what’s our headcount” in English, get an answer from the HR data. No report writer. No training class. Just ask.
The tool was called EasyAsk (holy cannoli, It's still around too). This was the mid-2000s. Flip phones. The natural-language query was “translated” (i.e. — mapped to SQL in the backend), ran against the HRIS and it worked, (mostly), which is roughly the same reliability rate as the version being demoed to your executives right now.
I need this audience to absorb that for a second.
“Ask your HR data questions in plain English” is the marquee demo of the 2026 AI era. Every vendor keynote. Every analyst deck. And a temp-turned-HRIS-guy was running it against a client-server HR system two decades ago, back when the revolutionary technology was a BlackBerry.
The technology underneath is different now, and genuinely better. But the lesson stands, and it’s the same lesson this newsletter beats weekly: the demo is never the hard part. The hard part in 2006 was the same as the hard part today. Whether the data underneath could survive being asked a question (and the mapping. Always with the mapping).
Everything old is new again. The people who’ve been here since the old version can tell you exactly where the new version is going to hurt.
The industry doesn’t let go
In 2008 the financial crisis (and a poorly timed back injury) did to me what it did to a lot of people. Laid off.
And here’s the detail I love in hindsight: two weeks after the layoff, I went to work for PDS. The company whose software I’d spent 4 years upgrading and wiring and interrogating from the customer side.
I didn’t escape the field during the worst job market of my lifetime. The field just moved me to the other side of the software. That’s the thing about HRIS: you don’t leave. The door only opens inward.
Twenty-plus years later I’ve been on the customer side, the vendor side, the implementation side, and whatever side “writes a newsletter about it” is. Every move traceable to one keyword on a job ad in 2004.
The sideways door is the point
There’s a podcast in our world, the HRIS Careers podcast, whose whole tagline is that no one gets into HRIS on purpose, but it sure is interesting to find out how they did. It’s the truest sentence anyone has said about this profession, and every origin story I’ve ever heard confirms it.
The person who “knew where the Access database lived.” The HR generalist who was “good with computers” and got handed the ATS. The payroll analyst who fixed one integration and was never allowed to do anything else again. The temp who knew SQL.
Nobody chose this. We got chosen, by proximity and competence, one weird problem at a time.
And here’s what I’ve come to believe about that: the sideways door isn’t a bug in how this profession staffs itself. It’s Ollivander’s shop (strap in Harry Potter fans).
The wand chooses the wizard. You walk in assuming you’re the customer, you wave a few sticks around, things explode, and then the right one finds you. And the old man’s explanation for why is the honest part: it’s not always clear. Not your transcript. Not your five-year plan. Something in the wiring.
That’s how this field recruits. Nobody picks HRIS off a shelf. The temp who knew SQL, the generalist who was good with computers, the payroll analyst who fixed one integration and was never allowed to do anything else again: the wand found every one of us, usually mid-explosion.
(Our ecosystem does contain one actual practicing wizard, the Workday Extend Archmage himself, Chris Humphrey, and I trust he’ll certify this framing as canon. The robes work because the magic is real.)
It only admits a specific kind of person. Someone curious enough to say yes to a job they can’t define. Someone unafraid of a system everyone else is afraid of. Someone who can stand between IT and HR and Finance and translate, all day, without belonging fully to any of them.
You can’t hire for that with a requisition. The wand has to choose you.
So no, we’re not failed IT people, and we’re not technical HR people, whatever that means. We’re the people who said yes to the weird job. Twenty years in, I’ve decided that’s not an accident to be embarrassed about. It’s the credential.
How’d you get in? Reply and tell me. I read every origin story, and I’ve never once heard a boring one.
— Mike
Director HR Tech | Purple Squirrel, First Rodeo
P.S. I told Justin I was writing about how nobody plans to end up in my field. He pointed out that he didn’t plan Justin’s 3D Lab either: “I just kept insisting you buy printers.” So there it is. Twenty years in HR Technology and the door still only opens sideways, even in my own basement.
The Department of First Things First. For the people who do the work.