Nobody decided to make it this complicated
Software gets messy the same way most things get messy. One reasonable decision at a time, with nobody watching the whole.
There's usually a moment, somewhere in the middle of trying to understand how an organization actually works, where you realize nobody chose this.
The CRM exists because someone needed to track customers. The spreadsheet exists because the CRM was too slow. The Notion doc exists because the spreadsheet wasn't shareable. The Slack channel exists because the Notion doc was always out of date. And somewhere in a manager's inbox is the information that ties all of it together, invisible to everyone else.
Nobody designed this. Each piece solved a real problem at the time it was added. What nobody tracked was the system they were building together.
This is how software gets complicated. Not through bad decisions. Through good decisions that didn't know about each other.
Why consolidation doesn't fix it
The obvious answer is to pick one tool, migrate everything, and start clean. This almost never works.
Migration is expensive and slow, and the reason the old system got messy is usually still true when the new one shows up. The CRM is still too slow. The data is still inconsistently entered. The people who were supposed to use it still find it easier to keep a personal spreadsheet. Give it two years and you're back where you started, just with a newer logo on the login screen.
What actually helps
Find the person everyone asks.
In most organizations there's someone who knows how everything actually connects. Usually not a manager, usually not in IT. They know which system has the real numbers and which one is usually wrong. They know the workaround for the thing that broke in 2022 and never got fixed. They know why the report takes three hours on Tuesdays.
That person is a single point of failure. They're also a map.
Start there. Ask them to walk you through how the work actually gets done. Not how it's supposed to get done. How it does. The gap between those two things is where the real design problem lives.
You don't fix this by consolidating. You fix it by making the connections intentional. Fewer assumptions, clearer handoffs, less weight on the people who hold it all in their heads.