I think that you have the right idea in by getting them comfortable with new software before switching to a new operating system. However, I think LibreOffice for Window$ would be a better next step than Screwgle Drive.
Ethics aside, it is possible they will disklike Google Drive because working in a browser is less familiar and also terrible because a slow internet connection + Google's bloated JavaScipt can slow down their workflow, making them even more closed-minded to new software. I have a friend who is working up to switching to GNU/Linux from Windows. When I told her that LibreOffice will replace Microsoft Office, whe was skeptical because people had told here that Google Drive was a good replacement and she hated it. The other possibility is that they will like Google Drive, which will do nothing to break the misconception that proprietary software is better than free software and might make them reluctant to revise their workflow a second time. It is also a step in the wrong direction freedom-wise. With Microsoft Office they were dependent on proprietary software. Now they are dependent on proprietary software and cloud computing. I understand the logic behind your strategy. Migrating one piece of software at a time is a more managable task than abandoning all proprietary software immediately. There are also situations in which I might suggest a piece of non-free software as an intermediate step. For example, if someone used an iPhone and was not comfortable immediately switching to Replicant. I might suggest temporarily switching to Android on a Replicant-supported phone, and installing Replicant on it once they have adjusted to some of the differences between iOS and Android-based OS's. I might even suggest LineageOS as an additional step between Android and Replicant. However, I would not suggest that an Android user swtich to iOS to get used to the idea of a different operating system, because that would be a step in the wrong direction. They'd be better of switching to LineageOS or Replicant next. I think this is a simialar situation. Google Drive is not a step in the right direction, but LibreOffice for Windows might be a good step before LibreOffice on Trisquel.
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