Need advice about moving to business versions of Office365 / Skype / OneDrive

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As the default IT guy for a very small business that started on the consumer offerings for Skype and Office, I’d like to get us onto the business plans, primarily for shared OneDrive space and ransomware protection. We currently use a hosted Exchange service that allows us to move to these plans.

But the transition to the business versions of all these apps and service worries me.

We are not co-located, so walking up to a colleague’s machine and fixing things is out. We do not have any “on-prem” infrastructure or AD. Pretty much all Windows machines.

Our Skype presence is through our personal accounts. (Do we need new accounts? How can we minimize the disruption in terms of contacts?)

Similarly we have dabbled in OneDrive and OneNote, but my one-month experience having my Documents folder on OneDrive a few months ago was terrible. Syncing would frequently stop for no reason, and I would have to stop and start OneDrive to re-start it. And on top of that it made my SSD feel like a HDD – plain old slow! I have about 11 GB and ~30,000 files, but I have 1Gbps up and down. (Next time I would not include any dev-related folders to reduce the OneDrive file count.)

So my questions are:

  1. How much un-installing + installing + configuring would be needed to move over our OneDrive, OneNote and Skype instances presences?
  2. Is noticeably slower SSD performance with OneDrive normal? Does my file count explain the slowness?
  3. Should I just push ahead and do it on faith … or is it as painful a process as it looks?
  4. If not, should we just use Box / Dropbox / something else ?

Thanks in advance!

Comments (28)

28 responses to “Need advice about moving to business versions of Office365 / Skype / OneDrive”

  1. Paul Thurrott

    It's too bad you can't use Outlook.com with custom domains. That would be better and a lot less expensive. And less complex.


    OneDrive performance should be comparable. It's the same client.


    Moving data between the consumer and commercial stuff shouldn't be difficult in any of the cases you mention.


    OneDrive consumer is better/cheaper than Dropbox (not sure about Box). It's been a while since I've used OneDrive commercial now, but it should be a very similar experience for the users.

  2. gregsedwards

    As an employee of a company that uses Box, I can tell you it sucks compared to OneDrive. The web-based UI is decent, but the round-trip editing requires a bunch of flaky browser and/or Office add-ins. It only supports Office document co-authoring if you use the lightweight bundled Office web apps in the browser. Otherwise, it has no clue whether someone else has the document open and will gladly allow you to overwrite each other's changes, unless you manually lock the file first. It has its own note app (BoxNotes) which is extremely basic. Box doesn't really support OneNote at all. There's a local sync app called Box Drive that works pretty much like the OneDrive client, except that search isn't integrated into Windows Explorer at all.

  3. waethorn

    Office 365 Business, if you don't want to migrate your email. It'll give you the OneDrive for Business service but that's it. Uses the same client as mentioned here.


    If you want to consolidate your email into a single plan, you're talking about migrating to Exchange Online, and Office 365 Business Premium would be the plan to get.


    Your contacts would have to be migrated over to Microsoft Teams if you want to make sure all your data is using those Office 365 accounts.


    If you have remote workers or multiple locations, just reconfigure PC's over remote access software. I use and recommend Zoho Assist, since it's available for every platform and also cheap (if you pay for it - but they have a limited free version too). The paid versions include unattended access. But I also find that Zoho Mail has been a better hosted mail service than Exchange Online, and far easier to setup too.


    If you're working for/running a business, using consumer services is a mistake. There are tighter controls on the business Office 365 plans, and they're built for business-level reliability, which the consumer versions are not.


    If your SSD seems slow, look for a vendor firmware update, or else test the SMART status for trouble (some vendor SSD tools will monitor the drive health).

    • ianw789

      In reply to Waethorn:

      Another great reply - thanks! You made me fully realize how Office 365 Business combined with keeping the existing 3rd party hosted Exchange might be the least disruptive path forward. Slightly more expensive, but a much simpler transition. Obvious in retrospect ...


      As for my SSD, it perked up once I put everything in a local folder and disabled/disconnected OneDrive entirely. So there was something about OneDrive ... maybe to do with Patrick3D's suggestion about open/linked files.

  4. BigM72

    It's worth considering G Suite too, depending on your needs. If your staff can get by with Google Apps (Docs, Sheets, GMail etc), I think it's supposed to be a lot easier to configure and maintain. You can run it all in the browser too.

  5. wright_is

    0. You would probably need to enable Azure AD and make new users and add the machines to the domain.

    1. Your Office would need to be de-installed and Office Pro-Plus installed. OneDrive personal and Business can co-exist and you would then need to move all your data from the personal drive to the Business drive. (Theoretically, you cannot use Office 365 Home/Personal for business use, it is purely for private use).

    OneNote should be just switched OneDrive for Business as well.

    Skype will similarly co-exist with Skype for Business or Teams - although as a new O365 business customer, you should only get Teams. You can continue to use both until you have migrated your customers across to contacting you through Teams. Your O365 users will each get a Teams address with the company domain.

    2. SSD performance shouldn't be affected. I have around 500GB of data on my OneDrive and I have everything synced. It runs at full speed. The only time it is slow is if there is a large changed document currently syncing that I try to open. O365 + OneDrive for Business should help for shared documents.

    3. It isn't that painful, but you should plan it out properly before jumping in. Come up with naming conventions for the user accounts and device names, so that it is easier to manage. Work out share document folders etc. and set the rights so that the right people can see the documents - and if you want to ensure the ransomware protection, all documents need to be stored on OneDrive not in local folders.

    Set up a test account and play with that and set it up on a spare machine first and learn what it does and iron out the configuration before pushing it out to everybody.

    4. If you choose to go with Box/Dropbox then you still need Office (or switch to LibreOffice, for example) and you still need a chat client, like Slack, for example. You can mix together different solutions, but it won't be as integrated, you will have to have multiple user accounts on the different services and you will have to learn multiple UIs for managing them.

    I'd go for the integrated solution, especially if you already have hosted Exchange and can upgrade that to O365, some of the work is already done. Just make sure you have the correct O365 subscription, with local Office installation (Pro Plus).

    • ianw789

      In reply to wright_is:

      Very helpful on many fronts - thanks!


      Why would we need Azure AD? Is having each user sign in with their own MSA a non-starter? (Right now we each generally already have an MSA of the form "[email protected]")


      • wright_is

        In reply to ianw789:

        MSA is for home users. Azure AD is for business and it is the Microsoft business equivalent of an MSA and automates the signing on to all the business services.

        You must have an Azure AD (@mydomain.onmicrosoft.com or mydomain,com linked to Azure AD) in order to access Office 365.

        It also allows you to remotely manage your PCs (group policies, remote wipe for stolen devices etc.).

      • AnOldAmigaUser

        In reply to ianw789:

        Azure AD is how Office 365 Business works. If you own your domain, you point the MX records at Exchange online and your users have addresses in the form [email protected], if you do not do this, then the email addresses are [email protected] This is the "work or school" account that is used to access Office 365 resources. Microsoft Accounts do not work with the business offerings as far as I know.

        You might want to invest in Tony Redmonds book "Office 365 for IT Pros", there is a lot of good information and they keep it updated. There is a discount for it at this address: https://gumroad.com/l/O365IT/WindowsWeekly

        • ianw789

          In reply to AnOldAmigaUser:

          Thanks. I'll look at that book. It's a messy topic!


          I was narrowing it down to "Office 365 Business" which explicitly does NOT include email. We'd keep the separate hosted Exchange for that; our MX records point there and everything works fine. That way Azure subscriptions, Skype IDs, etc. tied to existing Microsoft accounts would (hopefully) be unaffected.


          But I fear getting channeled down the "onmicrosoft.com" path. It seems like we might continue to log in to Windows with the "[email protected]" Microsoft account, but would also have to add the corresponding "onmicrosoft.com" account as one we also use so as to be able to use the OneDrive for Business and the Office apps. Does anyone know if this would work?

  6. arnstarr

    Microsoft includes tools to migrate your email from hosted Exchange to Office 365 Exchange Online. if your current inboxes are small (less than 10GB each) you could do a cut over migration, copying all content overnight or the weekend. You would change the MX record just before you start the migration, this way you are only copying old mail to Office 365 and new mail goes direct to Office 365.

    You can sign into OneDrive for Business (OD4B) and the consumer OneDrive at the same time. Then cut and paste the files between the two locations on a computer which has the files, to copy them up to OD4B. You can also use Microsoft's SharePoint Migration Tool to make the copy.

    OneNote migration is a manual process of opening the source notebook and a new destination notebook and moving each section from the source to the destination.

    You will need to keep using consumer Skype because there is no way to migrate contacts to Microsoft Teams or Skype for Business. Microsoft Teams does not support chat with consumer Skype, but it has been announced as an upcoming feature.



  7. Vladimir Carli

    I’m in a similar situation as you, I’m the tech-savvy co-owner of a small business with 8 people. In spite of being 8, we are divided between the US and Europe. Everyone turns to me for tech assistance as we don’t have the resources to hire an IT person.

    We have an office 365 business membership because word, PowerPoint and excel are the primary tools of our work. For everything else we use and pay different services (Dropbox for cloud storage, Evernote for shared notebooks, asana for project management, goto meeting for conferences). It has been my dream to consolidate all these services with office 365 because it would be a significant saving of money. However, each time I tried I had to go back due to technical problems that were extremely time consuming and risked stopping our business. In particular I wanted to give up Dropbox and Evernote and move to onedrive and OneNote. It has been a disaster due to unpredictable and unresolvable syncing problems. They happen all the time for no clear reason and the only way to fix them has been to delete everything and restart from scratch. I am not sure but my guess is that all syncing that happens with Microsoft services is much more sensitive to connection hick ups. We all work on laptops, frequently on the move. Dropbox sync is flawless, never had a problem in any condition, it just works for everyone. I think that if one drive sync gets interrupted at a bad time it’s not able to handle the situation and tends to halt forever. I say this because I have zero problems on my desktop that is constantly connected while problems frequently appear on laptops. It’s a shame, Microsoft should focus on making their services more robust instead of adding tons of features every month,. I guess the the thousands of features are a good selling point.

    Teams is promising and it’s very good for conferencing. The main problem for me it that it forces you to use outlook, which understandably no one wants to use. It would be good for planning team activities if they would only add the ability to manage a calendar from within the teams application itself.

    • ianw789

      In reply to Vladimir:

      Thank you. Your desktop vs laptop sync experience is very informative. We have pretty much all laptops and sadly your OneDrive sync description fits my one-month test with my laptop, and my mobile colleague's experience too. I certainly relate to your wish to simplify all those subscriptions -- without show-stopping technical issues!

  8. Patrick3D

    There are 2 primary questions you will need to answer for yourself (or within the company)

    How will users login to their computers? (local, MSA, Office365, shared generic account)

    What email address will they use for Office365? If you plan on transitioning Exchange accounts to Office365 it is generally recommended to give users new email addresses and use old addresses as aliases to avoid conflicts during the transition.

    As far as your OneDrive slowdown, OneDrive will sync infinitely if there is a database of any kind within a synced folder that is open or actively linked to by a program or file. This includes Outlook Personal Folder files (.PST) which the default location is DocumentsOutlook Files, and can also include Excel files that maintain links to other Excel files for shared data used in calculations/macros.

    • ianw789

      In reply to Patrick3D:

      Excellent point! I'd want users to sign in with their Microsoft Account and keep the same email address, and I'm realizing now that that means converting their MSA from personal to business. Your post makes me doubt that is possible.


      Thanks for the tip about open/linked files/databases with OneDrive. I'll revisit linked Office docs, Git repos and OST/PST file locations in any future testing of OneDrive.

  9. Paul Thurrott

    Also, this may be too much all at once, but moving to a Google infrastructure might make sense too from an ease of use/cost perspective.

    • ianw789

      In reply to paul-thurrott:

      Thanks, Paul. We are happily using Outlook + Exchange apps without issue (yeah - I know you see things differently!) so the disruption of moving to Google would be quite significant, and I'd need to do all the hand-holding. :-)


      Is it normal for OneDrive to make an SSD feel as slow as an HDD? (Specific cases of note: copy or move operations in File Explorer, and C compiler speed.)

      • wright_is

        In reply to ianw789:

        I would look at a GitHub/GitLab account / local server for managing the source code and store that locally, outside of OneDrive. You get proper version history, branching etc. and your protection against ransomware (just be careful not to include your private keys or passwords in the directories that are stored in the repo - yes, you can make private repos, it doesn't have to be public, although I believe you have to pay a small fee for that.

        The last company I worked for was transferring from a locally hosted SVN server to GitHub, with public (for the open source part of their work) and private* (for the commercial part of their work) repositories.

        * The company provides an open source security product, with basic rules and provides paid-for management tools and a paid-for feed of corporate security rules.

        • ianw789

          In reply to wright_is:

          Agreed! I have had Git source code repos for a long time on VS / Azure DevOps. Its the Office docs and various other data files on people's PCs that worry me.

          • wright_is

            In reply to ianw789:

            The normal office documents etc. should work at normal speeds, when synced. If not then there is something wrong with the configuration of OneDrive on the profile. Try creating a new Windows Profile for the user or de-activate OneDrive on the PC and delete the local OneDrive cache and then set it up again.

  10. minke

    We have a small nonprofit that runs on O365 Business Premium for nonprofits. We migrated from G Suite mainly because one user required Excel and also because we do use Word a lot, and some PowerPoint. OneDrive can mysteriously stop syncing for various reasons, though in general it has been reliable. One issue I discovered is that OneDrive will not sync properly if there are special characters in file names or the names are too long, or if somebody has added a wonky extension to the file name. Unfortunately, OneDrive just chokes and doesn't provide any error message as to why it isn't syncing. Microsoft has some pretty slick options for migrating your emails to O365 and I wouldn't worry about that part--it worked smoothly for us moving from G Suite. I suspect moving from hosted Exchange should be even easier. There are many services that will assist with the migration for a one-time fee, and it may be worth your while to pay for that peace of mind and time savings.

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