This one can be a little contentious at times. There are people on either side of the fence on why I should use it, or even if I should use it. There are several arguments that I often hear about Office 365 that I’ll address as well as several benefits I see from going to the cloud. This isn’t an attempt to convince you one or the other is bad, but merely helping make you aware of what you may hear.

The Benefits

  1. Servers – Frankly, you just don’t care anymore. You don’t care about the OS, you don’t care about security patches, you don’t care about the hardware, the storage, the performance, etc. With Office 365 Microsoft has relieved you of that burden.
  2. No More Patching – I’m an IT Pro (with a SharePoint background). This is a big one for me. I spent a lot of time as a SharePoint admin applying and testing cumulative updates and patches to the farm. This is also true for Skype for Business and Exchange. By going to Office 365, you get a lot of your time back simply due to the fact that you don’t care about applying and testing server updates.
  3. Users Focus (solutions, not maintenance) – This directly ties into the first two. Take the time you used to spend patching and maintaining servers and help roll out solutions to improve the business. This could be additional Office 365 services or solutions you create leveraging components or Office 365.

Some Common Arguments

  1. Return on an Investment – This can be tricky to calculate and there are a lot of variables that may go into calculating this. I hear a lot of arguments on ROI. My short answer is, if you purchase the whole suite and only leverage a fraction of what you bought, you may not see any ROI or if you don’t ever upgrade your on-premises environment. If you really take advantage of the whole suite, I don’t know how you can’t see an ROI. When calculating it, think about: Time applying updates, time updating hardware, cost of the hardware, cost of the on-premises licenses, cost of the data center (electricity, generators, space, security, failover data center, etc), the benefit you’ll get by admins helping with new solutions for the business rather than spending all their time maintaining what you have.
  2. Security – This could be a topic all of its own, I’ll just leave you a few things to think about here. First, I would maintain there are only a handful of companies (maybe) that have better security than Microsoft. Think about it like this, who can secure your money better, you or a bank? One of Microsoft’s primary jobs is to secure your data. They have more people dedicated to securing Office 365, they have way more knowledge about attacks due to the scale of the environment, and they have WAY more to lose if they would get hacked. They are going to MAKE SURE you’re data is safe. Their business depends on it.

A Few Disadvantages

  1. Errors/Issues almost always require opening a ticket – Your access to back-end log files or fixing issues on your own is greatly reduced. My experience has been, if you’re getting an error doing something in Office 365, just open a ticket right away. If you want to spend some time researching on your own after opening the ticket, go for it, but to get any details (or server fixes) taken care of, you’ll need a ticket.
  2. Updates can come if you want them to or not – Microsoft is always updating the various products that are a part of Office 365. If you’ve ever listened to our podcast and more specific the “News” episodes, you’ll get an idea of how much the cloud is always updating. While you usually have plenty of heads up about an upcoming update, it’s very rare, if ever that you can prevent it from coming. Your job changes from choosing when and how to apply updates, to when and how to alerts your end users that the updates are coming and to get ready for them.

There are many more advantages, disadvantages, and arguments that people have about if they should go to Office 365 or not. I can’t cover them all here, I just wanted to give you a few of the big ones I hear. If you want to talk about these in more depth or discuss other ones, feel free to reach out and I’m happy to help you think through additional points.

Things to think about

While the above section hopefully helped you think about if/when you should roll out Office 365, in this next section I want to cover some things you’ll want to consider once you’ve decided to roll out Office 365. These are considerations and aspects to think about before you push the button to deploy Office 365 to all your users.

  1. Bandwidth – This is a big one that not many people initially think about. When making the switch to Office 365, the amount of bandwidth that will be consumed by your internet connection will increase. In a typical on-premises environment, a significant portion of traffic would stay internal to your network. Communication between users would route through your on-premises Exchange server. Files would be saved and retrieved from internal file servers or over the local network to your on-premises SharePoint server. Skype for Business calls would take place internally between employees over your corporate network. Unless you have multiple locations or users working remotely over VPN, most of this network stayed within your corporate network and all stayed on your internal switches and network equipment. Now, all of this traffic must travel from your internal network, across your public internet connection to the Exchange servers, Skype for Business servers, and SharePoint servers all hosted in the cloud. As you work with files in SharePoint, send email to other teammates, initially, voice/video calls in Skype for Business, all the network traffic associated with those actions must travel over your internet connection.
  2. Firewalls/Proxy Servers – Closely related to bandwidth is your firewalls and proxy servers. These devices are the gateway to the internet and are controlling your connections and traffic flow from internal computers and workstations over the internet to Office 365.Firewalls may block traffic over certain ports. They may be filtering out the content or certain URLs. A firewall could even turn into a bottleneck if it can’t handle the influx of traffic caused by moving to Office 365, be aware of how your firewalls are configured and the traffic they can handle.

    Proxy servers are right there with firewalls. A common issue with proxy servers is the number of connections they allow. If you are a large enterprise, it’s possible that a proxy server may hit a connection limit when everyone goes to connect to Office 365. Outlook, Skype for Business, OneDrive for Business and your browser all create connections from your local workstations to Office 365. Make sure the number of connections isn’t going to hit limitations on any proxy servers you may have in place.

  3. Users – There are a couple things to be aware of here. First, the number of users. Again, relating right back to points 1 and 2. The number of users you have at a single location will affect both bandwidth as well as proxy servers and firewalls. On the flip side, if you have a lot of remote works that used to connect via VPN, they may not have to anymore and you might actually lighten your internet traffic.The second thing to be aware of here is a precursor topic to Lesson 5. This is where your users will be sourced and how they will authenticate to Office 365. You have three options here that we’ll look at it more detail later.

    Cloud only users: You don’t have any users on-premises or any local Active Directory you want to sync with. The ONLY place your users will live is in Office 365

    Active Directory, Authenticating to Office 365: Users live in a standard Active Directory environment and need to be synced to Office 365. These users still authenticate again Office 365 but their usernames and passwords are synced to Office 365.

    ADFS/Federated: Users are still synced to Office 365, but have a federated identity. This could be ADFS, Okta or some other Identity Provider (IdP). When a user goes to sign in to Office 365, they are authenticated against the federated IdP rather than Office 365.

  4. Other Current On-Premises Solutions – This is another two-part topic to think about. The first is related to the bandwidth point we mentioned above. While you can use bandwidth calculators to figure out how much bandwidth moving to Office 365 will consume, don’t forget that you may have other workloads running as well that will consume bandwidth. You need to account for bandwidth consumption from other applications + bandwidth consumption by Office 365.Second, you may have other workloads or applications that are integrating with services you are moving to the cloud. Maybe you use third-party workflows with SharePoint or a third-party email archive service. You might have conference rooms and devices integrated with Skype for Business on-premises. As you move all these services to the cloud, how is it going to impact these integrations?


That wraps up lesson 2 of the course. A quick recap we covered:

  • Some benefits of Office 365
  • A few common arguments against the cloud
  • Disadvantages that do exists with Office 365
  • Other considerations before jumping into the cloud feet first
    • Bandwidth
    • Firewalls and Proxy Servers
    • Users (numbers and authentication)
    • Current Solutions and Integrations