This post will be a bit of a confession, but I don't think I am alone in this problem. I am making a big push to go paperless - saving documents online, doing everything online, etc. My goal is a clean and efficient system.
However, I've discovered that over the years, I have not had a consistent naming convention or organizational system. It has made finding documents difficult. Fortunately, advanced search capabilities are helping reduce this problem, but it still exists.
The best example I can think of has to do with dates. I've noticed that I have gone back and forth between using numeral conventions (4-12-21) and typical conventions (April 12, 2021). Which means when I search based on date, I have to do both to ensure I find the document. This is just one of many examples.
This problem gets magnified when it is more than just one person naming files. For example, someone else on the team might put the date convention as Apr12, 21.
It isn't reasonable to go back and rename all the files - that would just take too long for a limited benefit. However, it is a good idea to set up a convention that you will use and then as you go through old documents, adjust the name to the convention. Don't forget to share that convention with the team and set the expectation that they will use it as well.
It seems like a little thing, but it makes a huge difference when trying to find that one document from 5 years ago.