Summary
The stakes
Two classification systems on one column
Who this was for
The Tech and Data Compliance (TDC) team with 17 analysts. Each analyst owns a set of domains and is accountable for the classification accuracy of every table in them.
The workflow looked something like this for each analyst.
What the users asked for
The compliance team came to us asking for a spreadsheet. They wanted every column for their domains exported to Excel, so they could mark it up and send it back for us to upload.
There were two problems…
The back-and-forth
The back-and-forth put the engineering and product teams into a monthly compliance process they had no reason to be in.
Sensitive data out there
It also put sensitive classification data into email attachments. The compliance team acknowledged this, but they wanted something built quickly so they could start fixing classifications.
The direction I was given
Product's direction was to give users a self-serve export of the full table list, let them work in Excel, and let them upload it back.
But it did not address the audit itself…
So I reframed the goal.
Three directions
2. Classification and mismatch filters.
3. Classification wizard
The constraint and the decision
The team preferred option 3, but engineering could not build it inside the deadline, which was driven by a compliance commitment.

What shipped
This is how the Phase 1 design looked.
This is the final design, where the user can either upload or edit all the data.
Early Results
What I took from it
Pushing back on a direction works better when you bring alternatives with you. Rejecting the export-only approach was only useful because I came back with three flows and a reason for each one.
When a constraint rules out the best solution, it is worth treating it as a sequencing problem rather than dropping the solution. Engineering's timeline meant option 3 could not ship in that release, but splitting the narrowing from the editing meant the most useful part of it still shipped first.
We only showed the compliance team the design at the end, once it was resolved. That was late enough that they could give feedback on the design itself, but not on which of the three directions we picked, because that decision was already made.