3 Simple Questions to Decide if Office 365 is Right For You

Recently, a colleague here at Entrance told me about an IT department looking for help with SharePoint totally unrelated to Office 365. The company has 400 employees and contract workers both out in the field and in the corporate office, and that they tend to collaborate with vendors and customers outside of their company. As he went on the describe the company to me, I realized that they have all the characteristics that make any company a perfect candidate to move to the cloud (and they didn’t even know it).

Your company may be just like these guys, too, so I thought it would be helpful to break down the parameters that make them such a good candidate so that you can use them to ask yourself a few questions that will allow you to get a quick idea of whether or not a move to Office 365 is worth more consideration.


One of the nicest things about Office 365 is that your employees are connecting to the service over the internet, which means it really doesn’t matter which computer they’re using or which domain they’re on. This is especially beneficial for clients with workers onsite with clients and not usually on the company’s domain. What in the past had been a complex exercise of setting up extranets or using VPNs is now a simple matter of pointing your favorite browser to the company’s O365 tenant URL.


Office 365 significantly reduces the complexity and security vulnerabilities associated with collaborating with external parties, be they clients or vendors. External sharing is managed from the Office 365 administrative console, and you can enable sharing in one place and disallow it elsewhere. You also have control over who is allowed to share with external parties, and if they can access content anonymously through a link or if they must authenticate using a certain login. The only drawback with external sharing right now is that it’s difficult to get a holistic view of what is being shared externally across all sites and whom it’s being shared with. Third-party tools can be purchased to help monitor this, and we offer this sort of monitoring as a service using such tools. The benefits to this external sharing are manifold and mirror the benefits of using SharePoint within the organization; namely, to reduce the friction that users experience when managing, sharing, and finding the data and documents that they need to do their jobs.


When we deploy SharePoint for a client, we do it in a way that is scalable, highly-available, and allows for robust disaster recovery. This means three tiers of servers representing the web-front-end that handles requests from clients, the application layer, and the database layer . Additionally, we will use at least two load-balanced web-front-ends and two database servers. This configuration can scale wonderfully and accommodate thousands of users, depending on the size of the servers and their processing ability. To us, this is a base configuration for the enterprise. It can scale up to handle even the largest clients, but for small clients, it can be overkill . The hardware, licenses, and services dollars that it takes to stand up an environment like this can get pricey. If have a few hundred people at your company who will access Office applications, it’s typically much more sensible to go with Office 365 instead.


I admit that these three questions are not sufficient to support a major decision about the future of your IT systems.

If your answers to these questions point to value in exploring this option further, your next step would be to dig into your use cases and non-functional requirements and compare the feature sets and all-in costs of on-prem versus Office 365.

If you have any questions, or need help with any of this, just let us know. We’ve helped many clients with just this sort of selection, and I have a guide on disciplined software selection which you can find here.

Originally published on the Entrance blog by Benjamin Smith