Well, everyone talks now about their telephony core system located in “THE CLOUD” and they want to convince you it is the best and clearer decision you may take recently.

But, should you?

First and foremost, before you jump into the the technical and price discussions or analysis, there is a simple question YOU need to ask yourself:

What is motivating the person in front of you? Is she or he understanding your business context and are you sure they will sell you a solution that matches YOUR interest and not theirs?

Supposing you answered … YES, then here you have a lot more questions for you:

– Are you sure you want to change your current phone service for a another comparable phone service? or you want to come closer the way the businesses, partners and employees communicate nowadays? I mean, percentage wise look at the voice communications, voice mail, versus chat or SMS and video and conferencing? How about presence information (knowing when a person is available to talk or not)? or Mobility inside vs outside the enterprise? or integration with your existing other voice communication devices, like cell phones and softclients, think Skype.

– Now, supposing you don’t need all those communication channels right away, please do acknowledge that your investment in the current phone services change you are planing will be lost if you have no clear road-map for adding those new features and services to your communication strategy. I don’t know if you’re old like me… If yes, please picture the people that 25 years ago were looking at the techies talking about a new thing called Internet and questioning the necessity to connect to it. Believe me, it is not a matter of IF but a matter of WHEN all this new communication channels will converge and become the way of exchange between companies and customers, please be prepared and have a plan. A such, if you want to move your phones to a Cloud core, please make sure you understand what will be the cost and the feasibility to add the future services to it. Will you have a cloud solution (and an extra client installed on the client computer) for each and every added feature – hmm, at this point the sales person in from of you might throw you some terms that you need to google – API, REST, SIP, TLS, OPUS, WebRTC, etc…

– Talking about SIP, make sure that ALL your company DID PSTN numbers are portable to the Cloud services provider. Is this provider covering all Canada? How about US? Don’t be shy to ask about the long distance cost on the new contract and what will happen to the existing 1-800 numbers once the DIDs are ported. Will faxes and DTMF still work after transition?

– And check if your former on premise solutions are portable to cloud as well ( Paging, call recording, CDR, receptionist customer software).

– Be sure you clearly understand what will happen to your enhanced 911 services. The costs will likely remain high if you need to keep a local voice gateway with couple of analog lines only for the 911 presence.

– How will you save money if you centralize your phones to a core reachable via IPVPN and need a lot of QoS bandwidth? What? You say you do not need private lines or QoS? Have you done a pilot for those 300 users in you head office – please collect the user feedback at the end of the pilot?

– Oh, lastly, but not less important, please make sure the transition strategy is clear and feasible. The success rate of transition projects in big-bang mode is very little ( the ones that succeeded costed double because of extended planning, tests and amount of people involved at the switch time). It is highly possible you will get through a hybrid solution where half of the users will be still on the legacy telephony while the other half is now in the cloud, please make sure you understand how those two hals are still communicating without disrupting your business.

As my father always asked me, before signing the contract, check and verify if you have an easy way to get out of the contract and what is the associated cost ( just in case…).