Software is supposed to make work faster. But sometimes the system the business runs on stops fitting the way the business actually works — and the team starts quietly working around it.
You usually don't see it on a dashboard. You see it in three places.
1. The spreadsheet that nobody talks about
There's a master spreadsheet — maintained by one or two people — that's somehow more authoritative than the system of record. The official tool has the data, but the spreadsheet has the truth. That's a signal.
2. The handoff that needs an explanation
Watch what happens between two teams who share data. If the handoff requires a Slack message (“hey, just so you know, the field in record 4521 actually means…”), the system isn't doing its job. People are.
3. The new hire who gets a hidden curriculum
Onboarding includes the official training — and then a quiet aside: “OK, so the system says X, but what we actually do is Y.” If new joiners need a hidden curriculum to be productive, the gap between the software and the work has grown too wide.
None of these are tooling failures, exactly. They're signs the work has evolved and the system hasn't kept up. The fix isn't always replacement. Sometimes it's automation, sometimes a thin layer of AI-assisted plumbing, sometimes just deciding what the source of truth actually is. But the first step is admitting the workaround exists.
