My Thoughts on Skype for Business & Transitioning to Microsoft Teams

Microsoft has announced that Microsoft Teams is the future for their Unified Communications (or “Intelligent Communications” as they coined at Ignite) vision. While I believe Microsoft Teams is indeed the future, it maybe too much too soon for some. This article provides my thoughts on how you might move forward based on where you are at in your journey to the Cloud.

For more information on this announcement and the features coming in Microsoft Teams see my post WOW Microsoft Teams! and the official Microsoft FAQ page.

Microsoft’s Positioning

At Ignite 2017 Microsoft pushed four key messages as I see it:

  1. Regardless of where you’re at in your Cloud journey, you should start trialing Teams
  2. If you are already planning your move to Skype for Business Online and do not require Phone System capability, considering moving directly to Teams
  3. If you are already planning your move to Skype for Business Online with Phone System capability, continue to do so, and when you are ready there will be a simple in-cloud migration path to Teams
  4. If you are not yet comfortable with Cloud, Microsoft is continuing to invest in Skype for Business On-premises

I’m going to elaborate on these points and how they might effect your decision making.

1. Trial Microsoft Teams

This is a great idea and one I totally agree with. There’s no harm in looking at the technology and seeing whether of not it fits your business, and at least getting your head around where Microsoft sees the future to be. This puts you in a position to decide;

  • This is for me!
  • This is for me, but not just yet
  • I’m jumping ship!

The key to a successful trial is picking a group of users who will get the most out of the technology. Because Teams is centered around persistent chat, it suits project work or where a lot of cross-department collaboration needs to occur; Teams allows users to participate in conversations that are important to them, catch up with past conversations, collaborate on documents and join rich audio and video calls.

Teams is also a great place to start your Office 365 journey. Because Teams aggregates Skype for Business, SharePoint and Exchange services, it provides a single simplified window to your Office 365 future, allowing your uses to get a taste of all these services without having to bit off more than they can chew.


2. Already Planning Skype for Business Online

If you are already planning to move to Skype for Business Online, this is a great time to look at whether Teams is right for you. Over time Skype for Business will roll in to the Teams experience, so you may as well start there if the feature set meets your immediate needs.

Key points:

  • Ultimately the Teams client will replace the Skype for Business client, however I do expect that at at some point there will be a lightweight version for those who will never participant in the full Teams experience, and want something that matches more closely to what they have now; in-particular I hope such a client has a smaller foot print
  • Teams currently does not support federation (the ability to chat with other businesses using Skype for Business, Teams or Skype Consumer), and guest access is an immature feature
  • Teams does not offer the full Phone System capabilities that Skype for Business Online offers. These features have started to surface with Dial-in Conferencing being released, with full calling capability slated for the second quarter of 2018


3. Already Planning Skype for Business Online with Phone System

If you are planning to move to Skype for Business Online Phone System, continue to do so. With Teams not yet supporting all Phone System features, this is your only option for now, however Microsoft have stated that the transition from Skype for Business Online to Teams will be a simple one; Teams and Skype for Business Online both share common back-end services, so a lot of what you get used to in Skype for Business Online, will be the same when you move to Teams. In fact, it’s likely that your only main concern will be the change of client for your end users.

Key points:

  • Microsoft plan to support all calling capabilities in Teams over time. This includes voicemail, call queuing, auto attendants, PSTN calling, PSTN conferencing etc
  • Microsoft plan to simplify Cloud Connector Edition by allowing you to “bring your own SIP trunk” using a supported gateway. As an example, Sonus have already said they will support this via a firmware update to their SBC1000/2000 SBC’s
  • Microsoft do not plan to support co-existence with Cloud Connector Edition (CCE) and existing versions of Skype for Business and Lync Server. For those who currently have Skype for Business or Lync Server on-premises, this makes things difficult if you want to migrate and decommission; your only option would be to migrate your users to the Cloud using Hybrid, and continue to leverage the on-premises server to breakout to the PSTN (if you where feeling daring you could spend the weekend decommissioning Server and replacing with CCE, but that’s just not going to be possible for large deployments). Hopefully this story evolves for the better!


4. Prefer an On-premises Solution

On-premises is clearly still on the Microsoft road map, with Skype for Business 2019 being announced for release at the end of 2018. Microsoft also said that it would be “very unlikely” that there were not further release of Skype for Business Server after that. Microsoft is promising to provide greater hybrid integrations, so that on-premises deployments can take advantage of Cloud only features, but has stated that hybrid will not be compulsory.

Key points:

  • Skype for Business Server 2019 will support hybrid with Teams, but there will be no Teams functionality built in; this will be delivered from the Cloud
  • The Director and Persistent Chat roles will no longer be included
  • Standard Edition will no longer be included, however a single server Enterprise pool will be supported, but it will still require a SQL backend. A 2 server pool will no longer be supported so you will need at least 3 servers for High Availability
  • In-place upgrade will not be supported to allow Microsoft to roll in Cloud born features to Skype for Business Server 2019
  • A “CCE like” “bring your own SIP trunk” solution will be supported to co-exist with Skype for Business Server 2019, allowing for an easy migration path to Cloud


Summarising My Thoughts

Microsoft Teams and Cloud UC is clearly Microsoft’s focus, where possible they want you to consider this path, however they understand that some customers are not yet ready. Being a heavy user of Microsoft Teams, I truly believe this is the future of communications and you should at least be considering it. Skype for Business Server 2019 provides on-going support for the Server version, however it is clearly targeted at larger customers, with Standard Edition (single server, no SQL back-end required) no longer supported, and Persistent Chat is dropped in favor of Hybrid with Teams.

With Cloud not quite being mature enough to offer all UC capabilities, and with on-premises Server being target at the upper end of town, it’s a tricky place to be if you’re a decision maker. Microsoft have promised a clearer road map to be released in October, so the story may become a whole lot clearer soon. I believe we are close to a tipping point where full Cloud UC will become a very attractive option (my guess is we are 12-18 months off this). There are some great capabilities in preview and more coming that will bring Cloud and on-premises to a level paying field – for example, third party solutions such as contact center and call recording will be a real possibility soon. Additionally, services such as Call Queuing (Cloud Response Groups) and call monitoring and reporting are about to get much better than their on-premises equivalent.

My view, which largely mirror’s Microsoft’s position:

  • Start trialing Teams so that you see how it might fit with your business. It’s where Microsoft is going, so you my as well assess this sooner rather than later
  • If you don’t need Phone System capability considering moving directly to Teams
  • If Phone System capability is a requirement, and you are already planning your move to Skype for Business Online, continue to do so. Once the capability meets your requirements and you are ready to do so, move to Teams
  • If Cloud isn’t for you right now, Skype for Business On-premises will be continue to be a viable option, and will allow you to leverage some Cloud only features if you want to

That’s all for now. If you found this article useful please considering sharing it, or subscribing to my blog at the top of this page.


Related Resources

This is a great comparison table by Luca Vitali of the various Skype for Business and Microsoft Teams features.

Skype for Business and Teams features comparison table

Mark Vale – Plan To Move Your Skype For Business Workload To Microsoft Teams




Andrew Morpeth
Andrew Morpeth
Andrew is a Modern Workplace Consultant specialising in Microsoft technologies based in Auckland, New Zealand; Andrew is a Director and Professional Services Manager at Lucidity Cloud Services and a Microsoft MVP.

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  1. Hi Andrew, this is a really good, honest look at the facts at this point in time. Very much appreciate the effort you put into this. I will be referencing this to help customer make educated decisions.


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Andrew Morpeth
Andrew Morpeth
Andrew is a Modern Workplace Consultant specialising in Microsoft technologies based in Auckland, New Zealand; Andrew is a Director and Professional Services Manager at Lucidity Cloud Services and a Microsoft MVP.

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