Age of the Hardware Platform
The most important consideration on when to migrate to Office 365 depends on the age and capacity of the hardware platform on which your email system is operating. If your organization moved to Exchange Server 2010 early, your server hardware is now 5 or 6 years old. This suggests a planned and orderly migration to Office 365 should occur over the next 6 months.
However Exchange Server was still being actively deployed as late as 2014 (especially as part of SBS 2011), so your hardware platform may only be two or three years old. This means it is still covered by the original manufacturer warranty and is still recorded in your financials as an asset. In most cases then, it is probably best to defer your migration to Office 365 until at least 2016.
Expected Growth of Staff Numbers
The above hardware based decision process assumes a reasonably static number of users within your organization. If that is not the case and you are expecting to increase staffing numbers by 10% or more over the coming 12 months, then a move to Office 365 before those numbers increase is recommended. There is no point in spending more money on either hardware capacity nor on CALs (client access licenses).
Do You Have Small Business Server 2011?
If you are running Small Business Server 2011 (SBS 2011), you might actually be able to maximize the return on your capital investment by continuing to run SBS 2011 into 2016. This assumes of course that you are running a Tier 1 brand server (for example HP) that is still covered by the manufacturer’s extended warranty and that you also have a Microsoft certified IT support expert monitoring and tuning your system on a regular basis.
Consider Your Office 365 Migration Options
Migrating from Exchange Server 2010 to Office 365 is the right decision for almost every sized business – especially those with less than 200 email users. The real decision is when and how to migrate. As mentioned above, the “when” depends largely on the age and capacity of your hardware as well as the expected growth of your business over the next 12 months. The “how” involves careful consideration on whether it is worth using internal staff to learn and perform a one-off complex project. It may well be that the best way to assure your organization of a successful Office 365 migration is to use the services of a Microsoft Silver Partner that has Office 365 certifications and real-world experience in performing Office 365 migrations.