Do you have IT budget to pay for a new system with a lot of money up front?
Do you currently use any cloud services such as: Dropbox, Netflix, WebEx, Salesforce.com, Apple iCloud, iTunes, etc?
Do you have dedicated on-site or IT people to manage your phone system?
Can your current system easily handle mobile workers, and regional office locations?
Is your current telephone system end of support or end of life?
Do you have custom integrations to other systems or databases, such as an advanced contact center?
Do you have seasonal variations in staffing levels or going through a high growth curve?
Does your current telephone system always have the latest features as long as you own or rent it?
Are you interested in being able to have your phone system extend to your mobile and PC?