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Analyst: Skype-to-Teams Transition Could Take Microsoft 3 Years

A recent talk by independent consultancy Directions on Microsoft gave organizations a look at what to expect from Microsoft's plan to transition its Skype for Business product to the newer Teams client.

Microsoft outlined some of its Skype-to-Teams roadmap plans last month. Previously, it had updated its "intelligent communications" announcement from September's Ignite conference which described plans for the Microsoft Teams client to eventually replace the Skype for Business client. Microsoft had given assurances back then that Skype for Business Online and Skype for Business Server unified communications products would both continue into the near future. A new Skype for Business Server 2019 product is expected to arrive in late 2018, according a talk this month by Mark Kashman, a senior product manager at Microsoft.

The shift to Teams, an Office 365 service, has lots of implications for organizations, particularly if they use Skype for Business Server in their datacenters (so-called "on premises" installs). In a Web presentation last week titled "Skype for Business Online and Teams Roadmap," Jim Gaynor, research vice president for enterprise infrastructure at Directions on Microsoft, offered some advice on what to expect in the next few years and how organizations can proceed.

Teams Plans
Gaynor quoted Microsoft as saying that there won't be an on-premises version of Teams. It means that the Teams Office 365 capabilities will eventually diverge from what can be supported on-premises, he indicated. With the Teams integration, Microsoft is using a newer infrastructure for voice and video that's shared with the consumer version of Skype. It's not the one used for Skype for Business Online, he explained.

The Teams infrastructure is being expanded to include capabilities on par with Skype for Business Online. Microsoft's goal is to achieve feature parity before calendar-year 2019, Gaynor said. Microsoft will continue to support Skype for Business Online hybrid voice, Gaynor said, but its features are being deferred in favor of a simpler PSTN connection model planned for Teams. He added that it's Directions on Microsoft's assessment that the Skype for Business Online service will be around at least until 2020.

Gaynor is a new member of Directions on Microsoft. He had years of experience, both as an IT practitioner and educator, before joining Kirkland, Wash.-based Directions on Microsoft. His talk outlined what's known about the transition to Teams, but also included a Q&A session.

Expectations and Directions
Based on Microsoft's announcements, Gaynor offered the following assessments:

  • Current Skype for Business solutions are expected to work at least until Oct. 2020.

  • Skype for Business Online customers should start evaluating Teams now.

  • Organizations should hold off on any major transition projects now to avoid having to go through a second transition.

  • On-premises Skype for Business customers should keep their environments current to ease later upgrades.

  • Organizations should start to work now with providers of customizations and third-party integrations if they use them.

Microsoft needs to bring several technologies together in mid-2018 to complete its move to Teams, Gaynor noted, but the risk of a schedule slip likely will be high. He added that 2020 likely will be the transition year to mark, both for Office 365 customers and on-premises Skype for Business Server customers.

Key Questions
During the Q&A part of the talk, Gaynor was asked a couple of key questions for organizations coming to grips with Microsoft's Teams roadmap plans.

He was asked whether an organization should delay carrying out a migration and wait for Teams if it were looking to migrate to Skype Online with Phone System and Audio Conferencing in 2018.

"Absolutely," Gaynor said, "if at all possible, unless there were things set in motion that required you to go. You'd go through that full migration. You're talking about training users, moving all the systems, getting everything set up -- I've done migrations in my past lives as work -- that takes anywhere like six months to a year, depending upon the size of your organization. To do that, and then to think that Skype for Business Online could possibly be end of life in 2021, I just don't see the value in that. I'd wait."

Gaynor also was asked whether Skype for Business Server 2015 users should upgrade to Skype for Business Server 2019 and then move to Teams, or if they should stay on Skype for Business 2015 until migrating to Teams.

"You're on 2015 now," Gaynor said. "You're going to need to evaluate what 2019 is going to bring you because we don't know if it's going to support the full feature set. And I don't know what your use case is for being on 2015. So you're going to need to take stock of any customizations you've done; how you have it interoperating with anything you've got -- call centers and that thing. And then, if you're on 2015 now, and you were doing that in preparation to make it easier to move to Skype for Business Online, then you might want to look at 2019 as your stepping stone to Teams at some point in the future. But that really depends upon what you've implemented, what your reasons are for being on-premises, and what your timeframe is for moving to a hosted service."

In response to a similar question from a Skype for Business Server user, Gaynor noted that the Microsoft likely wants organizations to move to its online services. There will be increasing pressure on organizations toward that end.

"It's going to be more and more like trying to swim upstream to avoid it," Gaynor commented regarding the shift to Teams and Microsoft's online services. New features will come online first, he added.

Roadmap Plans
Gaynor based his advice on statements from Microsoft, as well as consultations with the company, in which it outlined its Teams roadmap plans.

In late 2017, Microsoft will add meetings and basic calling support to Teams. The additions will include audio conferencing (in public preview now), application sharing, browser support for meetings, basic telephony support and calling interoperation with Skype for Business Online.

In early 2018, Microsoft's Teams plans include adding chat interoperation, unified presence, contact groups, federated chat with Skype for Business, Skype for Business interoperation with persistent chat, and messaging policies for retention and interoperation.

In mid-2018, Microsoft plans to add support for advanced meetings and telephony. The supported features will include:

  • Broadcast meetings, including large meeting support (approximately 250 users)
  • PowerPoint, whiteboards and Skype Room System support
  • Delegation support
  • Call Queues, Auto Attendant
  • Hybrid connections to Teams
  • Calls between Teams and the Skype consumer service
  • eDiscovery enhancements

Skype for Business Server 2019 is expected to arrive in mid-2018 as a preview, according to Microsoft's Kashman. However, Gaynor suggested that Skype for Business Server 2019 would preview in early 2018, with a mid-2018 product release.

Gaynor added that Skype for Business Server 2019 will be based on the Skype for Business Online code base, and its arrival will extend server "Mainstream" support phase to 2023. The new server will support the core functionality of Skype for Business Server 2015, but its improved hybrid functionality and management will be an on-ramp to Office 365. Skype for Business Server 2019 will require having Windows Server 2016 and SQL Server 2016 in place, he said.

In addition to the details in his talk, Gaynor noted that Direction on Microsoft has published supporting materials for its members. They include the publications "Skype for Business Online Functionality Moving to Teams" and "Microsoft Teams Capabilities Roadmap," he said.

About the Author

Kurt Mackie is senior news producer for the 1105 Enterprise Computing Group.

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