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What's the best approach / process to advise users of when discussing how to keep their document libraries and sites within their site quotas? (OnPrem instance)

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it is little very much open ended question. When user asked us about the quota increase, here what i do

  • If versionning enabled then limit it( i forced them for max 4 version)
  • delete the unused data(documents, sites etc)
  • Empty the recycle-bin.
  • if they are using SharePoint as storage place you may force them to different tools(if you company has)

  • Ask them why they need more storage.

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