Office Upgrade vs. Office 365 Migration

Is Office 365 the right solution for my business? This is a common question and deciding between migrating to the Office 365 subscription service or upgrading Office licenses is difficult until you understand what is involved with each alternative. The available solutions include new integrations as well as software upgrades and there are many factors to evaluate as you determine the best path forward for your organization. This article provides an overview of the options as well as pros and cons to consider.

Getting Started

The fundamental difference between Office 2016 and Office 365 is a license vs. a subscription. Microsoft Office 365 is a cloud-based version of the Microsoft Office Suite that is purchased as a subscription and includes more advanced capabilities and some additional software. Microsoft Office 2016 is the perpetual-licensed version of the Microsoft Office Suite which typically includes the purchase of one license per computer. Which version you select depends on the needs of your business both technically and financially.

Before You Begin

Functionality, responsibility, and investment level are three initial areas to consider. Based on the needs of the organization you must determine what functionality is required to meet your business need, where responsibility for maintaining the system falls within the organizational structure, and what the right investment level is for your business.

The first step is to conduct a complete assessment of your current Office implementation. Key areas to evaluate as part of the assessment include:

  • Configuration: How is your email system configured? (For example, Microsoft Exchange, IMAP, POP, and etc…)
  • Data: Where is your data? This includes documents, email archives, files, and databases that were created or need a Microsoft Office application to access.
  • Security Considerations: This is a good opportunity to assess security needs like email encryption, single sign on (SSO), and network connectivity like VPN.
  • Costs: Review costs including any infrastructure, hosting and other related costs in addition to the licensing costs.
  • Number of Users: Review the number or users. Organizations can provide a quick sum for the number of users, but you should go a step deeper and understand how each user is using Office applications. It is also wise to consider your future hiring plans.

These are just some of the considerations your organization should make before taking the leap to upgrade. Ninestone can assist you by completing a thorough assessment to help you minimize your costs and achieve the most value from an upgrade.

Picking the Right Option

While an assessment is being conducted you should take the time to understand the key differences between the two Office platforms.

Office 2016

Office 365

Upfront purchase is required to obtain a perpetual license to one specific version of Office per computer.

Subscription is purchased on a per user basis, per month/year, and provides greater flexibility to pay for only the applications each user needs.

Storage options are limited to user’s machines and/or file shares, but the ability to integrate third party cloud storage options or Microsoft cloud storage is available.

Depending on the subscription, storage options are flexible with Office 365 cloud first platform. Users will have access to cloud storage and file sharing with Office 365.

Future upgrades will require new licenses and an additional upfront purchase requirement. Users that need to switch or add additional Office applications will also be required to purchase a new license.

Because it is subscription-based, access to all future upgrades or features is included for the duration of your subscription. More features are included, and users can quickly and seamlessly switch between subscription offerings as often as needed.

Installation requires considerable IT support and possibly downtime for each user upgraded since the software must be individually installed on each device.

Is a cloud first platform that allows users to immediately begin using applications through their web browser. In addition, Office 365 allows users to download and install a local copy of Office as necessary with minimal IT support.


Whether you have an in-house resource or choose to engage an external partner, we suggest you work closely with your IT contact to complete a thorough assessment of your needs before making a final decision. It is important to go through the process with an IT partner that can both help define your organizational requirements and recommend the appropriate Office software components your organization will need. It is easy to overlook the process impact of upgrading regardless of which option you may choose.

Next Steps

As you determine what the right Office solution is for your business, consider the pros and cons of each option, the current needs of your business, your existing technology landscape, as well as upcoming and future initiatives. The right solution may require the purchase of new equipment but may also allow retirement of old equipment resulting in cost savings.

Ninestone consultants have extensive experience providing technology assessment services for both small business and non-profit organizations and can work with you on an assessment of your current systems and provide recommendations for moving forward. In addition, we have supported both large and small businesses through their Office 365 implementations and upgrades.

Case Study

Office 365 Implementation for a Non-profit Organization


Five factors to consider when moving to Office 365

The Ninestone Team

May 2018