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Skype for Business – Death Exaggerated, but on Life Support

Microsoft announced that it’s retiring Skype for Business Online on July 31, 2021, a little under two years from now, as I covered in my “RIP: Skype for Business” article, yet the on-premises version, Skype for Business Server, will continue on. However, I would argue that Skype for Business Server is now suffering from a potentially fatal wound.
When I started this article, I desperately hoped to incorporate the famous quote attributed to Mark Twain, “The reports of my death are greatly exaggerated”; however, researching the origin of the quote, it turns out that Twain simply wrote:
“I can understand perfectly how the report of my illness got about, I have even heard on good authority that I was dead. James Ross Clemens, a cousin of mine, was seriously ill two or three weeks ago in London, but is well now. The report of my illness grew out of his illness.”
Details matter. And so too with the retirement of Skype for Business Online.
In theory, as highlighted by Microsoft, Skype for Business Server isn’t affected by the retirement of Skype for Business Online. In theory!
In reality, retiring Skype for Business Online impacts Skype for Business Server in two critical ways:
1. Emotionally: It feels like Skype is dead.
Consumer Skype
Skype isn’t dead. As a consumer brand Skype, acquired by Microsoft in 2011 for $8.5 billion, is alive and well:
Skype for Business
Skype for Business Server, the business-focused solution, continues to provide voice and meeting services for many medium and large organizations. Moving from a traditional PBX to Skype for Business Server for voice and conferencing often saved organizations millions or tens of millions of dollars, at least for the ones I helped migrate. Skype for Business continues to deliver excellent voice and conference quality and reliability for over 10 million active users and likely more than 100 million licensed enterprise seats. (While Microsoft recently announced Teams has 13 million daily active users, a vast majority of these users aren’t using Teams voice services, yet.)
So, Skype for Business is still providing voice and meeting services for many organizations, and yet almost all the news and marketing coming from Microsoft focuses on Teams.
Microsoft Ignite
Microsoft Ignite is an annual conference for developers and IT professionals at which Microsoft communicates its future direction and works to convince attendees to move in the same direction. Ignite session topics provide good insight into future focus areas for Microsoft.
  • 254 session descriptions include a mention of “Teams,” such as:
    • “Meetings made simple with Microsoft Teams”
    • “Microsoft Teams Rooms deployment for an inclusive and enhanced meeting room”
    • “Intelligent communications in Microsoft Teams”
    • “Streamline business processes with the Microsoft Teams development platform”
  • Only 16 sessions include a mention of “Skype,” and over half of these are sessions focused on helping you move from Skype for Business to Teams. These include:
    • “Upgrade from Skype to Teams,” slotted at five different times
    • “Designing your Path from Skype for Business to Teams”
The message couldn’t be clearer: Teams makes things simpler, inclusive, enhanced, intelligent, and streamlined. Skype for Business is something to be moved away from.
While digital technology is based on binary decisions and logic, the truth is that most enterprise technology strategies are driven, at least initially, by opinion and emotion. Few organizations have the resources to evaluate every viable option, and so, “feeling” Skype for Business is dead stands a good chance of becoming a self-fulfilling prophecy.
2. Technically Skype for Business is being left behind
Beyond opinion and emotions, several quantitative factors are making Teams a stronger long-term platform when compared to Skype for Business.
Microsoft investments are fully focused on Teams (at the expense of Skype for Business). Microsoft as early as 2017 stated that 95% of its engineering effort is focused on Teams, along with 100% of its sales efforts.
Teams Capabilities Match and Exceed Skype for Business
As early as July 2018, senior Microsoft representatives declared that Teams had complete feature parity with Skype for Business. This stretched the truth and was comparing Teams features with those of Skype for Business Online, as opposed to Skype for Business Server. Now over a year later, it’s reasonable to suggest that Teams can provide calling and meeting features comparable to those of Skype for Business Server. Beyond parity, Teams delivers features that exceed those of Skype for Business and Microsoft has no announced plans to ever add any of these new features to Skype for Business:
  • 2 x 2 video display
  • Background video blur (and customized backgrounds)
  • Content capture (transforming an ordinary whiteboard into a digital marvel)
  • Live captions (with real-time translation in the future)
  • Cloud-based meeting recording and meeting transcriptions
  • Notification when someone joins an upcoming meeting
  • A greatly improved mobile client that better maintains chats between desktop and mobile and can do more, such as sharing screen during a meeting
Skype for Business Server 2019 Brings Almost Zero New Features
While Microsoft did release a 2019 version of Skype for Business, the update provides no end-user focused features. The list of what’s new doesn’t include any on-premises features. The list of what’s deprecated is much longer.
Stepping-Stone to the Cloud Eliminated
Many larger organizations that had success with Skype for Business were beginning to look at the opportunity to home some users in the cloud using Skype for Business Online. While the capabilities of Skype for Business Online never matched those of the on-premises version, this type of hybrid arrangement provided a low-risk way to test the capabilities of cloud-based communications ahead of moving to Teams.
Skype for Business Online thus was a step toward Teams. With the elimination of Skype for Business Online, the hop, skip, and a jump becomes a very long leap.
Skype for Business’s death may have been exaggerated, but only slightly. Both emotionally and technically, Skype for Business is dying. Even if Skype for Business is providing excellent benefits to your organization, it can only be kept on life support for so long; you need to start saying your goodbyes and planning your transition to Teams now.