We spend a lot of design effort on how data gets into a system — the forms, the validation, the transactional database quietly recording everything in neat rows. We spend far less on how it comes back out. And when the person who needs a weekly report is a loss prevention officer rather than a software engineer, "just use the API" turns out to be no answer at all.

In this episode, Andrea Magnorsky and Kenny Schwegler are joined by Kat Hempstalk, a data and AI professional who has been doing machine learning "since before it was cool." She brings what she calls "a bit of a tragic tale" from her time as head of data and AI at a company handling retail crime reports. Before she arrived, the company had solved the export problem by hiring a graduate to write Python and SQL scripts and email spreadsheets to customers by hand. It worked — until that person went on holiday and literally handed their laptop to a colleague so the reports could keep going out.

An engineer eventually received that laptop, thought "this is a bit scary," and added a little automation: a Windows VM, scripts synced through GitHub, scheduled tasks, files dropped into blob storage. The manual button-pressing stopped. The underlying problem just got faster to reproduce. Within a few years, three or four people spent their days copy-pasting scripts into 200 bespoke customer reports — reports that turned out to be five or six shapes wearing different hats. Collapsing them was the easy part. Telling customers their format was about to change, when the customer success team said "No, I'm out — I don't wanna give the customer bad news," was not.

This conversation is about where data engineering and software engineering stop talking to each other, and what leaks through the gap. We dig into invisible contracts (a column heading is an API), why the order you migrate customers in is an architectural decision that cost this team a year, what embedding data people into software teams actually requires, and Kat's discovery that most of the customers fighting to keep their scheduled email had never once opened it.

Key Discussion Points

• [00:01] A Bit of a Tragic Tale: Kat introduces the retail crime platform — reports go in easily, and getting them back out was never designed
• [00:03] Your Users Know Excel, Not APIs: Why loss prevention experts don't want a programmatic endpoint, they want a spreadsheet
• [00:05] The Laptop Handover: The graduate goes on holiday and passes the laptop along so the reports keep flowing
• [00:06] "A Bit of Automation" Becomes Load-Bearing: A Windows VM and scheduled tasks make the problem faster to reproduce, not smaller
• [00:07] Three People Copy-Pasting Scripts: 200 custom reports, an unhappy analyst team, and customers waiting months to add a column
• [00:11] The Query That Came Back Too Fast: Moving to a data warehouse, and the insights analyst who assumed the speed meant they'd made a mistake
• [00:13] Two Hundred Reports That Were Really Five: Consolidating into templates — and why that's a conversation problem, not a technical one
• [00:19] The Emails Nobody Opened: Customers insisting on scheduled reports they'd never clicked, because they wanted reassurance, not data
• [00:24] "No, I'm Out": Customer success refuses to deliver bad news, so the data team has to own the conversation
• [00:26] The Order You Migrate People In: Starting with friendly customers built momentum, but the resistant ones set the pace for everyone
• [00:29] A Column Heading Is a Contract: Customer-defined attributes reordering spreadsheets, and moving to nested JSON so nothing downstream breaks
• [00:34] Clear Fences Make Good Neighbours: Andrea on the boundary between data and software teams, and Kat on embedding people across it
• [00:39] What Goes With the Person, What Stays: The handover conversation they skipped, and the systems that broke silently as a result
• [00:42] Collaboration in the Agentic Era: Why the people best at sharing context and contracts are also the people getting the most out of coding agents

Guest: Kat Hempstalk

Hosts: Andrea Magnorsky, Kenny Schwegler