Things to consider before buying Office 365

If you are considering buying Office 365 or Microsoft 365 for your business here is a quick checklist to run through of some of the things to consider. This is by no means a comprehensive list – and as a consequence I may come back to this over time to add to it.

I should also note – this isn’t meant to put anyone off migrating to Office 365 / Microsoft 365 but simply to help organisations to think intelligently about the scale of the project they are undertaking.

Anyway – enough of an introduction – here is my list of things to consider.

Are you a business or an enterprise?

Microsoft split their customers into two groups depending on whether you require more or less than 300 “seats” or licenses.

  • If its 300 or less you fall into the “Business” camp.

  • If its more than 300 you fall into the “Enterprise” camp.

However – the Enterprise products are available in any number of users so if you don’t like the offers / bundles in the “Business” packages and you have less than 300 users then you can always choose the Enterprise packages anyway.

Do you want your licenses to include the OS & an MDM?

In general Microsoft’s base bundles are either just the Office suite, or the Office suite, Operating System and a Mobile Device Manager (MDM). Those that include only Office are called “Office 365” and those that include Office, the OS and a MDM are called “Microsoft 365” with the notable exception of Microsoft 365 Apps for Business and Microsoft 365 Apps for Enterprise.

Do your users use dedicated devices?

Microsoft have a small number of license bundles at a lower price for those users who either don’t have a dedicated device or only access the Office suite using a tablet or smartphone. If this matches some of your users you should consider if you could use the F type licenses for them – for example Microsoft 365 F1 and F3, and Office 365 F3.


How will you manage Licenses?

Capacity in Office 365 -i.e. how any emails can be stored, how many documents can be stored in Onedrive and Sharepoint etc – is generally managed by the choice of product – once you’ve chosen the product the capacity is set. But buying more licenses than you need will lead to unnecessary cost to the organisation. So you will need to match again and again over time the number of licenses you hold to the number of users you have. Similarly there is a financial tipping point in regards to feature licenses vs an upgraded bundle containing that feature license. This may be a new discipline for the organisation. Who will have responsibility and budget to do this?

How will you access Office 365?

A bit of leading question here – historically there have been two ways to access Office 365 – over a dedicated ExpressRoute circuit or over the internet. If you haven’t heard of ExpressRoute let me explain; it’s a dedicated network circuit (or pair of circuits) from you to a Microsoft Data Centre via an approved intermediary. You can access both Azure and Office 365 through the ExpressRoute but accessing Office 365 required an ExpressRoute Premium circuit at higher cost.

Microsoft no longer recommend any organisation accessing Office 365 over ExpressRoute – they recommend accessing it over the internet and to be honest this is much simpler and a lot cheaper than the required ExpressRoute Premium.

Specifically Microsoft say here:

Microsoft authorization is required to use ExpressRoute for Office 365. Microsoft reviews every customer request and authorizes ExpressRoute for Office 365 usage when a customer’s regulatory requirement mandates direct connectivity.

So unless you have a regulatory reason requiring access to Office 365 over a private circuit you should not be using an ExpressRoute to access Office 365. I can’t think of many UK based organisations that would have a regulatory reason to access Office 365 privately – most organisations that had such a requirement would probably not be allowed to use Office 365 being as its a publicly hosted multi-tenant service.

Do you have sufficient internet bandwidth?

If you are not currently using Office 365 then your internet bandwidth requirement will inevitably increase. Ideally you should profile your users to get an indicative view of the impact and then run a pilot to check your predicted per-user bandwidth matches real world experience.

Remember not to just consider the internet bandwidth however – but also the network elements in the path to the internet feed – can your firewalls and proxy servers handle the increase in bandwidth?

Do you have sufficient internet RESILIENCY?

Its fairly normal for a business to consider their email system or their document management system as a business critical system. If you are moving it to the internet then you need to verify that you are happy with what happens in the event your primary internet feed fails. But not just your internet feed; your internal firewall, your external firewall, any proxy you have etc.

Does your hardware meet the requirements to run Office 365?

I think its fairly likely that your devices – your laptops and PCs – will meet the minimum requirements to run Office 365 but you should check that you are happy with the user experience this will give. For example if you have devices with older Intel i3 processors and only 4GB memory and a 5.4k HDD you might want to check what the user experience feels like.

Also – you might want to consider where you are on your roadmap to upgrade devices to Windows 10. Office 365 will run on older versions of Windows but its designed to work best on Windows 10.

You will also need to consider your mobile devices – will they run Office 365 and do you have an effective way to manage them?

Have you thought how much time your staff will have to spend on remediation, installation and migration?

Imagine for a moment that the introduction of Office 365 to a large enterprise is the simultaneous upgrade of Exchange, Sharepoint, all file servers, active directory, your firewall and proxy service, your load balancing solution, and the introduction of around 20 new services that you never previously had…

Doing this will require a lot of time from your internal ICT staff – it will not be a simple activity. You should work with a MS partner to identify all the remediation activites that are required before migration and then plan what the remediation, installation and migration will look like. This will require a project manager or project managers depending on your organisation size.

Do not underestimate the complexity of this task – especially if you are a large enterprise.

Have you thought about how Office 365 will affect future staffing?

Let’s suppose for a moment that you have a team managing your on-premise email service, another team managing the file servers, another team manages sharepoint and so on. Have you considered what effect migrating to Office 365 will have on these teams if suddenly there is either no on-premise or minimal on-premise Exchange environment, sharepoint environment and file server environment?

Microsoft position Office 365 as a SaaS offering meaning that these staff will no longer have to manage the low level elements of these services. Some analysis will need to be done into which parts of their roles will vanish, which will change, and what new things they will need to take responsibility for.

You need to consider whether you want your staff to fully administer Office 365 or whether you want to engage with a partner and ask them to manage some elements.

Have you thought about training for ICT staff?

Once you have worked out what administrative tasks you want your staff to complete and what you would like a partner to complete it is important to consider training.

There are a number of formal training courses that ICT staff can consume covering a range of topics from Office 365 security through to Sharepoint. There are also a range on free and paid online training courses covering most topics.

You need to work with a Microsoft partner here going through the different administrative tasks and identifying who will complete them and whether or not there is a knowledge gap. This should develop into an ICT training plan for Office 365.

Have you thought about training for all your other staff?

Your team needs to understand how to use the Office 365 product – how will their experience be different to what it was previously? What will be new to them? Again there are a range of options here – from remote learning, classroom training, floor walking and mentoring that can be considered.

However, our recommendation is that training for non-ICT staff should integrate into and form a part of an adoption plan. This will help to ensure that the necessary training for a particular element of Office 365 aligns with when the feature is enabled and promoted within your organisation.

Have you thought about adoption?

The Office 365 suite of products is massive and complex. As such to get the most out of your investment you should plan how and when it gets given to your staff. You should know which features will be made available on what dates and what is the aligned messaging and training for the feature. Additionally, you should be monitoring the usage of the feature and providing wide ranging support to staff both from peers, online, and from your ICT staff.

Setting this up properly is complex and needs to be properly invested in.

Have you considered what evergreen means?

Office 365 is not a static product – its not that you install it and leave it for 10 years and then upgrade it. It is constantly changing. Microsoft add features regularly, try out new things, remove those that don’t work. You need to be ready for this. How will you test the regular updates that are issued? Will you even test them? How will you keep up to date with the changes? How will you inform users about the changes?

The “Evergreen” nature of Office 365 will affect how you manage the product – you will need to work out whether you will let some groups in your organisation get new features first to become champions to the changes. Keeping up will be challenging.

Have you thought about having a Office 365 Network Assessment Completed?

We would recommend you have a Office 365 Network Assessment completed before migrating as this would allow any roadblocks to be identified before users encounter problems and complain.

We can provide a Office 365 Network Assessment for you – this would consider your TCP-IP configuration, DNS configuration, network latency and jitter, available internet bandwidth, WAN and many other areas and include recommendations around what action to take to fix any issues encountered.


This isn’t a particularly structured list but more a brainstorm of things to think about. There are many more things to think about than I’ve listed here. Key takeaways from me here are:

  1. The network is really important – especially bandwidth as it needs sorting early due to lead times and the associated costs

  2. Licensing is complex – you need to know what you staff do and how they work but also what they will do with Office 365 in order to make the right decisions – again it has a cost

  3. Don’t under estimate how much time it will take your ICT staff to assist in a Office 365 migration – time costs money – to free your staff to do migration may require backfill which has a cost

  4. Adoption planning and the associated user & ICT training need to be factored in and cost time and money to get right.

Whatever you do don’t look at the price of Office 365 and think “That’s all I need to spend” as it really isn’t.

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