Office 365: the gotchas

Ready to use Office 365? Great. But with such a large product there are invariably things you should know before you set out on your new collaboration adventure.

I was recently asked, “what should an organisation be aware of when looking to use Office 365?”. Essentially, what are the gotchas?

As an IT consultant I could talk all day on this topic, but instead I’ll try to boil it down to a few simple points, things to consider as you embark on your new great adventure…

Ideally, have some semblance of a plan

There is a sliding scale for how you can use and manage Office 365. This ranges from a “free-for-all” (‘organic’) model, where anyone can use it as they wish, to a tightly managed (restricted) model, where everything is locked down.

Once you’ve had a look through the different products during your trial period, I would encourage you to think how you might want to use and manage this in the business. Given what you know of the product and your business, where on the scale would suit you best? Even if you do change your mind later, it's still good to have a plan. Also, stating the obvious, make it a positive plan, i.e. how you can use 365 to benefit your business.


If you don’t already have your own Active Directory then Office 365 includes a way to create and manage user logins purely within the cloud. However, if you do already have one (or several) then you can choose between:

  • Synchronising your user login and password hashes with Office 365, you then use Microsoft provided login screens to login.
  • Using your own federated login (i.e. where you host the login screen and authenticate users), in Microsoft AD circles this will likely be ADFS.

You can just start of using the inbuilt logins if you want and then add in your own AD. But, you may find that your “limited trial, to see how things go” quickly snowballs into many people using it throughout the organisation, in which case sorting permissions and merging accounts after the fact may cause a headache or two.

Related note, I encourage you to make use of multi-factor authentication for your Office 365 logins, particularly administrators.

Data, Data, Data

Of course, boiled down to its simplest form, Office 365 is just a new shiny repository for your data. So all the normal rules apply as they would anywhere else. There are three things to consider:

Security of Data

What security requirements do you have for your data? Do you need to consider who can access it internally? If you plan on using the external sharing features, are there any particular restrictions? Do you need to apply retention policies?

Office 365 has a wealth of features for managing your data, from basic access control through to sophisticated security and compliance features. If security and compliance is a big concern then ensure you review each part of the Office 365 suite as some parts have more features than others.

You should also consider the wider ecosystem, do you encrypt your laptop hard drives for example? What happens if a user leaves their laptop on the proverbial train? Are there any really restrictive data residency requirements?


An interesting one, Microsoft perform their own backups to ensure current data is not lost (aka RPO). They also provide additional functionality within certain products to provide versioning (so you can go back in time) and recycle bin functionality (so you can restore deleted documents for a limited time).

However, Microsoft will not restore data beyond a couple of weeks — and even then it is not guaranteed. So, if you need to keep historical backups or want to ensure a quick SLA then you should look at third party backup solutions.


No system is good without something useful in it, and chances are you already have a lot of data in your business you would like to use. Therefore, you need to consider what data you want to migrate (perhaps now would be a good time to do a spring clean?) and how you want to migrate it.

For your method of migration, you could do a lot of it by hand or use a migration tool. Microsoft provide a few different tools of their own, but you may find if you have any complicated requirements you might be better off using a third party product.

Amount of storage is also a factor in migration. Microsoft does supply you with a lot of storage out of the box, but once you run out you are then charged extra per month for additional storage used. Therefore, if you already have a large amount of data (maybe a hoarder’s paradise of a network share?) then think about what amount of data you need and/or how much additional storage you may need to purchase.

Desktop Clients

Hopefully you are already using the latest Office clients, in which case skip this step. If not then you should ideally upgrade as soon as you can. Currently Office 365 supports previous clients (with reduced functionality depending how old your version is), but soon they will only support the clients still in mainstream support.


Although Office 365 contains many products that your users may be familiar with or can pick up quickly, you should consider what training is required and how you will deliver it. Microsoft provide a wealth of training material and there are a number of training providers who can help you further if necessary.

I’ve written a separate article that covers the change management considerations in more detail. Put simply, don’t leave your users high and dry and expect them to flourish.


Office 365 requires a decent internet connection, particularly if you have many users sharing the same line. It will work on poor connections, but obviously the more people sharing a poor line the slower things will become. This may be particularly acute if you have previously been hosting a server on-premises in your own data centre. Consider, therefore, if your connection is adequate or if now is a good time for an upgrade.

Also, you may read that you can set up a direct connection to Microsoft using ExpressRoute, but, Microsoft already has a large number of peering connections worldwide to get people onto their global network as soon as possible. Therefore I advise you not to waste your money on this — although you may wish to check your internet breakout points, particularly if you’re routing traffic away from your Office 365 data region (see below).


Office 365 is a global product and is split into different regions. When you create your tenancy you have to pick a region and this can’t be changed, except in very, very limited circumstances. If you have highly restrictive data residency requirements then you should check carefully as data may be geo-replicated to a different country, usually the USA. Most organisations will be covered under the standard legal arrangements that Microsoft have in place.

More relevant for region choice is latency, although Microsoft do their best with caching, CDNs and peering, fundamentally your data and servers are in the particular region you chose. If you are based in Europe and have an office in Sydney then you may find the performance is slightly lower in Sydney. If this becomes a big issue then you either have to create a separate tenancy on a different active directory domain (this can get complicated) or you can use a local server running in hybrid mode, for that office to use instead.


Office 365 is always being updated. The good news is that this means your environment is always patched and you don’t have to wait years to make use of new features. The flip side of this is that the environment is rarely static, certain things may change and new features are added.

This means you should be aware of the changes and how they may affect you. Microsoft does provide regular updates in your Office 365 admin centre to keep you informed. If necessary, for certain changes, you can trial this with a set group of users first. This also includes considering how you can benefit from the new changes to make the most of your Office 365 subscription.

Swiss Army Knife

As there are many ways to cook an egg, so in Office 365 there are often different ways to accomplish what you want. Want to communicate with your team? You could use Outlook, Teams (Skype) or Yammer. Want to store files? You could use OneDrive or SharePoint.

My advice is familiarise yourself with what each part does then, as per my planning advice earlier, sketch out how you will direct people to use each element. For example:

  • Sharing a file with the company? Use SharePoint.
  • Sharing a file with your immediate team? Use Teams.
  • Sharing a file with 1–3 people: Use OneDrive.

You should look at Office 365 as a Swiss army knife. It has many different elements you can use in different situations – some of which you may never use — for example, StaffHub may not be useful to your organisation, but PowerApps might be.

If you find Office 365 doesn’t do something you want, there is a rich API and development ecosystem that would allow you to develop or purchase something that might accomplish it. Alternatively, you can post a suggestion on the UserVoice feedback site and they may add it — though this tends to be a long shot.

Licenses and Add-Ons

As you will have seen, Microsoft offer a range of licences for Office 365. Most companies will be purchase E3, or E1 as these give you a lot of “bang for your buck”. Smaller businesses may be better suited to the business plans.

In addition to this, you can buy individual products, for example “just email”, or “just SharePoint”. There are also then a wide array of add-ons you can purchase, to name a few:

  • Power PI Premium
  • Dynamics CRM
  • Intune
  • EM+S
  • Visio
  • Project
  • …and many more

If you already have an IT or licencing partner it would be worth checking what they can offer. Sure, you can pay for it all on your credit card should you wish, but you will likely find your partner may offer preferential payment methods and terms. For example, most if not all subscriptions through Office 365 require yearly commitments, whereas your partner may be able to offer a month to month contract.


For different reasons you may find that you need to keep Exchange, Skype or SharePoint on-premises. In this case you should investigate a ‘hybrid’ configuration. This allows you to have a connection between Office 365 and your data centre, rather than just choosing one or the other.

Be wary of elements that may not work as expected, and only configure this if you know what you’re doing — if in doubt seek expert advice. If you are considering hybrid, I would suggest that Microsoft’s (unofficial) view is that hybrid is a means of providing a stepping stone to the cloud and that realistically on-premises isn’t here to stay in the long term, at least not in its current guise.

Not Your Servers

If you’ve come from a self-hosted environment you may be used to jumping on to a server to fix something. Unsurprisingly, you can no longer do this. In many ways this is good and in most cases you can still accomplish what you need through the Admin portal or PowerShell. If you can’t fix it through either method, then you have to go through the guardians who are Microsoft support. On the whole they’re very good, though if your issue is transient or limited to one or a few users then be ready to have a few calls to reach a resolution.

The big upside to this however is patching, data storage, resource usage and scaling are no longer your concern.

Is it worth it?

Absolutely. Of all the collaboration offerings on the market Office 365 is the most comprehensive, and has seen a lot of innovation in recent years. Is it the best of everything? No. Is it perfect? No. But if you’re looking for a collaboration platform that you can tailor to benefit your business then Office 365 is, in my opinion, the leading contender.

Final word, as with most things in life, you only get out of it what you put in to it, so be bold and make the most of it!

Jisc | Data Matters

26 January 2021

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