We are in the process of moving all our files (sitting on windows file servers) to Google Drive. I anticipate that the users will be using more of the search capabilities of Google Drive than navigating the path like they are doing right now in the windows file server. Since the file structure has been here for a long time (there are many many files, with same name, with same info, etc..), I don't want users to have difficulties finding the files they want to work on but at the same time have all the files they need.

What are the best practices regarding a file structure migration? Should we copy everything to the cloud? Or should we take this opportunity to clean up and ask a department "leader" to move the files he feels are necessary? Or should we copy only files that have been accessed since X years? What are the options and recommendations?

2 Answers 2


You should use the chance to make the structure better, but not without providing enough knowledge for everyone so he can find the things he is looking for.

You should "layout" a new better structure and work together with the different departments so everyone can give his input.

You should migrate all files to your new host if you aren't limited with hosting capacity.

  • Hi @Pectoralis, is your answer based on your experience or some theory/documentation? Oct 10, 2017 at 16:34
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    Speaking from personal experience, on my last company the system admins started to migrate all our (before hosted locally) files to dropbox (around 3 terabyte) without changing anything and not really asking the different departments about the structure (keeping the old one). Soon after most departments said they would like to change the structure and the whole process was redone while this time asking the departments. It showed that most departments had issues with the structure because it was old and they just kept using it because of time reasons. Oct 11, 2017 at 7:24
  • This is something we wanted to avoid for sure, so the structure part has been discussed with the users already and it will be changed a little. The main question is do we copy all files or not. Have you ever been in that situation? Oct 11, 2017 at 12:52

In my experience, it is always better to take the opportunity to cleanup your file structure - perhaps even reconsider the structure all together. There are many advantages in moving to Cloud-based storage but this can be undermined by poor file structure that some users (if not most) would find tedious to work with.

What I would advise is that you make an in depth analysis of the current structure on Windows, identifying areas that can be improved, abandoned or perhaps even introduced, just to make the structure better and more intuitive to the users.

Once you identify this, propose to the users and work with them to agree on the new structure. Once agreed, upload that to the Cloud.

In a nutshell, it is easier to clean up before you move to the Cloud rather than after.

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