Skype Means Business

Redmond's decades-long quest to become a force in universal communications begins its latest chapter with the integration of Lync and Skype.

Now that Microsoft has started rolling out Skype for Business, the company is hoping IT decision makers will find a clear connection with its latest stab at becoming enterprises' primary universal communications provider. It's indeed a tall order, but the company appears poised to put significant resources into making Skype for Business a key pillar of its "platforms and productivity" mission.

Skype for Business, which marries Lync 2013 and Skype, brings to enterprises the best features of both. Microsoft has long aspired to upend the traditional market for communications systems. Microsoft's work to develop universal communications technology dates back to the mid-1990s, but Skype for Business roots trace to the company's introduction of Live Communications Server in 2003.

When Microsoft released Lync Server five years ago, the company argued it would up the ante on providing core universal communications experiences in a field dominated by Avaya Inc. and Cisco Systems Inc. thanks to much broader acceptance of VoIP to replace legacy telephony systems, notably PBXes, and the willingness to run voice and data on the same networks.

With the release of Lync Server 2013, Microsoft added Lync functionality to a major revision to its top-tier enterprise editions of Office 365. While Lync Server 2013 arguably became more competitive and has become more widely implemented than previous releases, it's yet to become the go-to communication for core corporate communications within many organizations.

Having made Skype for Business available to Office 365 customers earlier in the year, the company in May released Skype for Business Server 2015 as an "in-place upgrade" to Lync Server 2013. Customers can control when and how they roll out the Skype UX in their individual organizations. The new Skype for Business Server 2015 includes support for the Microsoft SQL Server AlwaysOn feature, interoperability with Cisco Tandberg VTC videoconferencing systems, a new call-quality dashboard and the ability to connect with anyone in the Skype directory.

If you're wondering how to explain the justification for implementing Skype, you don't have to. This is Skype for Business -- think OneDrive for Business versus OneDrive. It's been four years since Microsoft purchased Skype for $8.5 billion. Since then, Microsoft has offered two overlapping universal communications offerings, but in ostensibly separate universes -- public and private. Skype exists just as it did before as a consumer VoIP, videoconferencing and instant messaging service, but Skype for Business brings with it more administrative control for organizations and allowances for much larger calls and meetings. While both applications encrypt VoIP conversations, Skype for Business gives administrators stronger control over the userbase and the feature sets allowed by organization users.

New Interface
Perhaps most visible to end users is the Lync interface is replaced by the Skype experience. There's no need to fear Skype for Business from an interface standpoint. It's just not different enough to give most users any distress. The desktop application is slightly modified, but still recognizable and intuitive. The client, like its predecessor, offers a status bar, a color-coded system designating a user's presence online, an icon-based navigation, and the ability search, configure and build contact lists.

Integration with Outlook and setting up and administering meetings via the application remain nearly the same -- it's actually the under-the-hood improvements that make Skype for Business the more powerful communication tool.

Once a user launches a Skype meeting the new voice and video options (see Figure 1), including enhanced third-party video call interoperability, and a consumer-­pleasing Rate-My-Call feature have large organizations and productivity in mind.

[Click on image for larger view.] Figure 1. The Skype interface replaces the Lync UI for call control and videoconferencing.

Skype for Business encourages communication across all Office platforms, particularly Outlook. Presence shows in Outlook and Skype for Business indicating a unified experience, and conversations can be saved into Outlook. The presentation options include sharing PowerPoint presentation files, attachments and notes files. Additionally, meeting administration features such as adding additional contacts on-the-fly and recording lend themselves to impromptu collaboration sessions.

The Skype for Business people search allows users to search for organizational contacts by name or skill set, and administrators can allow users to search the entire Skype userbase for out-of-organization communication.

"One of the things that's cool about this search is that we actually use a part of the Bing search engine heuristics to be able to go through the graph -- this graph is huge, several hundred million users," says Jamie Stark, Microsoft's Skype for Business product manager. The Bing connection allows for a more phrase-like people search -- for example, a search for "Mike Jones in Seattle, Wash." is going to return more limited and reasonable results than a search for all the Mike Jones in the entire Skype userbase (see Figure 2).

Figure 2. Users can search their contacts and the Skype directory.

Most of these changes exist on a micro-level -- users interact with them in their individual machines, potentially on a smaller meeting scale -- but many organizations are strategically extending the Skype technology to completely recreate the online meeting experience.

In March Microsoft announced two initiatives targeted at transforming physical meeting spaces into effective virtual spaces. The first, Skype Room Systems, reimagines conference rooms and conference room technology. The new experiences -- built in conjunction with Microsoft partners Crestron Electronics Inc., Polycom Inc. and Smart Technologies -- are all built on a Windows 10 platform and will be rolling out in line with Windows 10. The Microsoft Surface Hub, coming in September, continues to move organizations in this direction. The Surface Hub is a large screen, whiteboarding and video device created for conferencing (see Figure 3). Given its size, it's aimed at conference rooms. It comes in 84- and 55-inch Ultra HD displays with Skype for Business built-in. It will include sensors, cameras and the ability to mark up content with any phone or device.

[Click on image for larger view.] Figure 3. The Surface Hub is Windows 10-based and brings Skype for Business into the conference room.

Knowing not every organization is going to install a full Skype meeting room, Microsoft is also working with Polycom to create a line of audio and visual devices aimed at leveraging the Skype experience at a variety of price points.

On-Premises vs. Office 365
The Office 365 and on-premises feature conversation continues to permeate the landscape -- and it's no different when you turn your attention to Skype for Business. Until recently, Office 365 was lagging behind the on-premises implementations, but last month Microsoft released three new feature previews that put Office 365 back in the mix.

Perhaps most notable is the rollout of PSTN calling capabilities running out of Office 365. On the flip side, Lync Server 2013 clients, who already partnered with third-party public switched telephone network (PSTN) providers, didn't see any break in landline to VoIP transition when they upgraded to Skype for Business. Using the Microsoft Azure ExpressRoute Service, partners such as AT&T, BT, Colt, Equinix, Level 3 Communications, Orange Business Services, TATA Communications, Telstra, Verizon and Vodafone will be able to provide dedicated and high-speed Skype for Business connectivity services.

In early June Microsoft announced Skype for Business integration with Outlook -- both inbox and calendars -- and OneDrive. Users will be able to start conversations and calls directly from these applications -- this contextual experience is the hallmark of Office 365 and it encourages quick and efficient collaboration. The new integration will appear in the top navigation, and Microsoft expects to roll this out to its First Release clients starting in just a few weeks. Add to that the recent preview of Skype Meeting Broadcast, which allows for up to 10,000 users to attend a worldwide town hall from any device, and suddenly the enterprise communication landscape has shifted.

Also coming later this year are Cloud PBX with PSTN Calling, which lets Office 365 subscribers initiate or receive calls from any landline or mobile phone and the ability to use common voice-calling features such as hold, resume, forward and transfer.

Mobile Connections and the Web App
Many organizations continue using alternative screen and Web-meeting software when including users outside the organization. Many IT decision makers have found Lync Server 2013, like its predecessors, unreliable, particularly with external users.

"True or not, I just felt like Lync Server 2013 was unreliable for meetings with external users," says my colleague Jen Miller, director at Protiviti Inc. This perceived unreliability, shared by many, is exactly what Microsoft promises to address with Skype for Business Server.

The Skype for Business Web application doesn't require external users to install anything other than a Web app plug-in on their local machine. Given myriad settings on different organization's users' machines, a first-time user may have to do a bit of troubleshooting, but once the Web application is launched it can be launched again and again without additional setup time. The older the users' systems, however, the more difficult it typically is to join the Web application. Users who have a particularly difficult time joining the sessions should refer to the matrix provided by Microsoft and determine if basic hardware and software are the root cause.

Attending Lync meetings via apps is nothing new, and while updated mobile applications are on the Skype for Business roadmap, they aren't debuting in the near future. In the meantime, the Lync 2013 app for Windows Phone, iOS and Android is compatible with Skype for Business. Attending meetings via the app only requires an Internet connection -- users can designate how they join calls via their actual phone number or via VoIP.

Roll-out Strategy
While upgrading to Skype for Business Server 2015 is Microsoft's recommended path for most organizations, Skype for Business is supported on all Lync Server 2013 environments running at least the December 2014 cumulative updates. Infrastructure limitations, such as phone system support of Skype for Business, might force organizations to run in dual mode until those limitations are addressed.

Once the technical infrastructure (see the minimum hardware and software requirements) is in place, there's no reason to wait on rolling out Skype for Business. Skype's best-in-breed functionality was what attracted Microsoft in the first place, and its already-robust userbase is certainly an added bonus. For organizations that want time to socialize the change internally and produce training and transition documents, there's an option to control the end-user experience and continue to leverage the Lync experience until the time is right to make the full switch.

Users from companies previously running Lync Server 2013 are finding the transition to Skype for Business Server 2015 relatively quick for large companies where other enterprise technology upgrades take months, if not years.

For Office 365 users there are far fewer decision points with Skype for Business. One morning you'll wake up and Skype will just be there at your disposal. Microsoft has released a few Windows PowerShell scripts that'll allow administrators in an Office 365 environment to control the UI until the organization is ready to officially "make the change."

Office 365 users should review their plans carefully; different subscription levels can include different features. E3 and ProPlus licenses now include PSTN capabilities, but Office 365 Business doesn't include the Skype for Business app at all.

Until now, many organizations have been reluctant to replace their traditional PBXes -- in most cases due to real (or perceived) bandwidth issues in rural areas or international offices. Microsoft published recommended network standards (see to mitigate bandwidth issues. As Skype for Business grows and continues integrating more and more with Office applications, the larger strategy piece for many organizations is predicated on Skype for Business governance and how far organizations want to take the VoIP and video experience. And even once IT decision makers decide they want to implement its core features, organizations will still want to see whether implementing it with the rest of the Microsoft stack offers the economic benefits and is as useful as their existing communications infrastructures -- or if a mix-and-match strategy is the best route.


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