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Success With Skype: Key Decisions to Make Now

The first stop of the Enterprise Connect Tour: Implementing Microsoft Lync/Skype for Business in Your Enterprise successfully wrapped up in San Francisco last Thursday. I am now back home after a whirlwind couple of days that saw me flying from the East Coast to the West Coast, and then departing almost exactly 24 hours after I landed. (Note to self: This is likely too much travel in too short a period of time.)

Speaking of being short of time, based on the discussions in San Francisco, here are several key questions that many organizations need to ask right now. (During the San Francisco keynote I discussed these features and more.)

1. When should we upgrade to Skype for Business server?
While you may have already upgraded to the Skype for Business client, which brings a streamlined user interface, many of the benefits associated with Skype for Business are only available after you upgrade your server infrastructure. These include:

Even though Microsoft supports an "in place upgrade" when moving from Lync 2013 to Skype for Business Server, for any medium or large enterprise, this upgrade process will require careful planning and execution. If your organization isn't comfortable with the risk associated using the in-place upgrade mechanism, then you may need to buy new servers -- and that requires a budget.

2. Should we wait for the new Microsoft cloud PBX services?
Microsoft has begun offering a number of interesting cloud services that extend the capabilities of Office 365 and potentially could complement or supplant on-premises deployments of Skype for Business for some organizations. These are available in "preview" to some U.S. customers:

In San Francisco, Skip Chilcott, a product marketing leader with Microsoft UC, took the time to outline the upcoming rollout roadmap with expected release dates for the various services both in the U.S. and internationally.

Given these new services, if you are just planning an upgrade to Lync 2013, should you wait? Should you put your on-premises Skype for Business upgrade on hold? Should you consider a hybrid deployment with some on-premises workloads and some workloads in the cloud?

Keep in mind that using any of these cloud services likely requires an Azure ExpressRoute connection to Office 365 in order to provide consistent voice quality. ExpressRoute enables customers to create private connections between their premises and Microsoft data centers. Microsoft has announced that its myriad partners -- tour sponsors AT&T and Tata Communications, plus BT, Colt, Equinix, Level 3 Communications, Orange Business Services, Telstra, Verizon, and Vodafone -- will deliver direct connections.

One of the key challenges is that Microsoft has not published service pricing, likely to be bundled into a new E5 client access license. Without pricing you cannot perform a financial analysis of options.

3. Do multivendor integrations make sense with Skype for Business? Specifically, is splitting call control between Microsoft and Cisco a viable solution?
With Office Communications Server, Cisco created a client integration called CuciMOC that relegated the Microsoft platform to IM and presence and kept call control on the Cisco platform. With Lync, Cisco gave us CuciLync. As far as I know there is no CuciSkype.

Splitting call control between the Microsoft and Cisco voice platforms has worked, with varying degrees of success, for some organizations by creating a direct SIP connection between the platforms. This on-premises link is the approach often used to connect legacy IP PBXs.

Skype for Business offers a new integration opportunity, called "Call via Work," that allows a contact or number to be dialed in the Skype for Business client and then have the Skype for Business server first ring your legacy Cisco desk phone. Once you answer the inbound call, the Skype for Business Server then executes the outbound leg of the call. This approach also ensures the called party sees your work number as the caller ID, regardless of the phone you are using for audio.

The new Call via Work feature requires you to have upgraded to Skype for Business Server and allows Microsoft to fully deprecate the previous remote call control feature, which in my experience was rarely beneficial.

These are important questions with answers that will differ based on the specifics of your defined UC goals and your existing infrastructure.

As San Francisco illustrated, the Enterprise Connect Tour brings together a great collection of experience, insight, and opinions. Lots of great discussion and debate is packed into a single day that can help get you started on finding the answers to your important UC questions.

Next stop: New York, where the apples are big and the discussion should be lively. Don't miss out! Join us for the Enterprise Connect Tour: Implementing Microsoft Lync/Skype for Business in Your Enterprise, a free, fantastic, all-day event that brings together a powerful collection of experts to assist you on your Skype for Business journey. Following New York, on Thursday, Sept. 10, we hit Orange County, Calif., and Chicago on the next two consecutive Thursdays.

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