Why wait? The top 10 things you need to know about upgrading from Skype to Teams
Published Feb 19 2020 09:00 AM 39.6K Views

Skype for Business versus Microsoft Teams

While it might be tempting to wait for a deadline, there’s less and less reason to postpone the upgrade to Teams. Microsoft Teams gives brings capabilities that your users already enjoy with Skype, like messaging, calling, managing contacts, or hosting online meetings, but it goes beyond to deliver all of this in a single hub for teamwork that can connect to your favorite apps and enhance productivity. Of course, some of the biggest differences between Skype and Teams are under the covers. Teams is built on a modern platform for audio and video and uses the latest cloud infrastructure on Azure for optimized global coverage, which brings several performance and networking benefits. For example, meetings get started faster and user ratings show that call quality in Teams.  For an IT Admin this means you can expect fewer helpdesk calls related to meeting experiences and calling.  

Also, because Teams is cloud-native, it benefits from ongoing innovation such as whiteboard sharing, background blur and in-line translation, which allow for a more inclusive collaboration experience. Best of all for you in IT, we give you a comprehensive admin experience for day to management, security and compliance. We covered more on this in previous Essentials episodes at aka.ms/MicrosoftTeamsForIT.


Choosing your path to Microsoft Teams

Another good reason to start your upgrade to Teams now is that whether you are coming from Skype for Business Online or Skype for Business Server on-premises, with or without Enterprise voice, we have a number of robust options to help in your journey to Teams. If you follow our guidance as you make the transition, you trust that no user will miss a chat message and meetings will always be accessible either from Skype or Teams. Here are some pointers on the top things to get started:


1. You may not need to do anything at all: 

For smaller organizations that do not have hybrid or on-premises dependencies and are using Skype for Business Online only, Microsoft offers an automated upgrade for your Office 365 tenant. We will notify you in advance in the message center and via email if your tenant has been selected for this automated upgrade. This is a great benefit if you don’t have dedicated IT staff. Learn more about this at aka.ms/TeamsAutomaticUpgrade.


2. Upgrading from Skype to Teams is more than just a technical upgrade:
Aside from specific architectural considerations, the rate at which users adopt Teams will impact your timeline and influence the success of your upgrade the most. Managing change across your users is imperative to any successful adoption strategy. Your roll out team needs extend beyond IT to incorporate the right sponsors and stakeholders such as executive sponsors; a project lead to help instigate and keep track of training and roll-out milestones; and various champions that can share user feedback. We explain this in more detail in our video.


3. Microsoft Teams comes with built-in upgrade options and interoperability: 

This applies whether you are coming from Skype for Business Online, Skype for Business Server on-premises, have a hybrid configuration, or have an enterprise voice plan.


4. We allow you to incrementally get your organization on board:
Skype and Teams can coexist during your upgrade. This way, while you gradually onboard users or groups of users to Teams, you have flexibility to ensure the pre-requisites are in place with SharePoint, OneDrive, Exchange, Azure AD synchronization, and network optimization requirements.


5. There are two main upgrade paths to choose from:

  1. The first path has overlapping capabilities across Skype and Teams and is enabled with “Islands mode”. This is our recommended path to start with. Note that by default, this will be the coexistence mode for your tenant. Because chat, meetings, and VoIP calling are available in both clients, your users can get familiar with Teams while still being able to access all the features from Skype at the same time.
  2. The second path is where you can pick select capabilities selecting from two interoperability modes. “Skype for Business with Teams Collab and Meetings” mode, also known as our "meetings-first approach", allows to have chat and calls initiated and received in Skype while scheduling and collaboration capabilities are handled by Teams. Otherwise, you can keep chats, calls and meetings in Skype while collaboration capabilities remain unique to Teams with team conversations, file sharing, and co-authoring enabled with “Skype for Business with Teams Collab” mode.
  3. Once your organization is ready, you can turn on Teams only mode, which means all incoming calls and chats land in the Teams client. In fact, if you have PSTN calling configured, users will receive all incoming voice calls in Teams, and PSTN connectivity is enabled with a calling pad that lights up in Teams.


6. You can mix and match your coexistence modes:

Modes can be set organization-wide or for specific users in the Teams Admin Center or using PowerShell. You’ll want to use PowerShell if you have a large number of users that you want to assign specific modes to, and we have a range of cmdlets that enable you to perform bulk actions, such as setting modes with or without user notifications. This allows you for example to have subsets of users still on Skype for Business with select capabilities, or on overlapping capabilities, or just Teams only based on the upgrade strategy for your organization.


7. A hybrid configuration is required if you are coming from Skype for Business Server on-premises:

User accounts in Skype for Business Server need to also be present in Skype for Business Online for interoperability with Teams to work. If you are already using Office 365, you probably have this in place already. Also, a hybrid configuration with Skype for Business Online needs to be in place to ensure that chat and calling traffic between Skype and Teams is automatically transferred via our gateway service. You’ll need to use PowerShell for that, and you can learn more about the steps at aka.ms/TeamsSfBHybrid.


8. There are two voice options to enable integration between your PSTN or Voice over IP services:

• A Microsoft calling plan: If you are using a phone system and a Microsoft calling plan where Microsoft provides your phone numbers directly, once you enable Teams only mode traffic is routed to Teams automatically, or
• Direct Routing, which can be configured in a few ways.. If you have an on-premises Session Border Controller device that connects directly with your PSTN trunk line from your telecommunications provider or ISP, you’ll need to route the connection to your Microsoft 365 tenant. Or, if your Direct Routing is done off-site by your telecommunications provider via their Session Border Controller, you will need to work with them to direct PSTN traffic to your Microsoft 365 tenant.


9. There are tools to help you to track organizational readiness:

You can track Microsoft Teams usage in your environment with built-in usage reports and dashboards available in both the Microsoft 365 admin center and the Teams Admin Center. We also recommend circling back with your onboarding team and conducting regular end-user surveys using Advisor for Teams. This will help you to capture user feedback and sentiment and ensure you have a comprehensive perspective on the readiness of your organization to upgrade to Teams.


10. Your users’ contacts and upcoming meetings can also be upgraded to Teams:

The migration of your data and meetings, like interop, for the most part happens behind the scenes. There are options to automatically upgrade upcoming Skype for Business meetings across all your users’ calendars to Teams.

If you want to learn more, I encourage you to watch our Skype to Teams Upgrade Tutorial. Also keep checking back to aka.ms/MicrosoftTeamsforIT for our next Essentials show on best practices for getting your organization to adopt Teams broadly. Check out additional resources at aka.ms/SkypeToTeams and our instructor-led workshops at aka.ms/SkypeToTeamsPlanning. Lastly, stay tuned and keep watching our full series at aka.ms/MicrosoftTeamsforIT.


Thanks and happy upgrading!
Nydia (connect on LinkedIn at: https://www.linkedin.com/in/nydia-cavazos/)


Regular Visitor

@Nydia Cavazoscould you please take a look at the formatting of this article? It is a pain to read with such messed up formatting.


Thank you for letting me know, @mdicha ! It got messed up with the headings, i think i fixed it =).

Regular Visitor

@Nydia CavazosLooks solid now, thanks.

Occasional Contributor

@Nydia Cavazos Articles like this at microsoft REALLY need to mention the major shortcomings with the voice api. Almost all common voice integrations or functions that people depended on for a decade with lync/sfb are DEAD and due to the extremely lacking api there is simply no way to replace them with teams as of today. Every single gold level microsoft partner says the same thing and everyone is getting smoke screens from microsoft on this. It is frustrating ms continues to ignore this issue with no response to many users and continues to push teams as if it supports all sfb features. Can MS PLEASE provide a response to the thread where everyone is complaining about this or the uservoice detailing all of the gaps in functionality? See the comments here for example: https://techcommunity.microsoft.com/t5/microsoft-teams-blog/what-s-new-in-microsoft-teams-january-20...

Occasional Contributor
Thing #2: Buy another monitor. The Teams chat UI is far larger than even Skype 7's. A compact chat mode has been the #1 UI request on the user forums for most of the last 3 years. (https://microsoftteams.uservoice.com/forums/555103-public/suggestions/17408641-please-create-a-profe...) For most of that time, the Teams team said they were "working on it", but progress recently has all been backwards.
New Contributor

We can't deploy Teams as we use Citrix and each teams session uses 1gb of Ram which is way to high compared to SfB. This needs to be addressed before we can even think of migrating.

Senior Member

I'm disappointed that partner services were not even mentioned. Particularly for Phone System, few customers can make the PBX migration journey on their own, and the rest probably shouldn't even try.

Occasional Contributor

Microsoft continuing to gloss over the limitations of Teams voice compared to Skype for Business Online and relentlessly pushing them to upgrade now does their customers no favors. 


- Teams has a very poor front desk/operator workflow. Skype wasn't great; Teams is worse.

- No Better Together functionality - this creates islands between physical phones and the PC client.

- Teams Mobile app is unusably slow - it takes 10-15 seconds for the Teams app to start ringing, even on WiFi. I miss 3 out of 4 calls.

- Migration of Skype delegation to Teams is broken - there's no way to clear Skype delegates once users have been moved over to Teams Only mode. This affects 3PIP phones that still run Skype through the gateway - those Skype delegation relationships still appear and mess up boss/admin coverage.

- Service reliability of Teams/Skype for Business Online is still really poor. The expired certificate issue was a human error black eye, but check out the Service Health history - something has been going down at least once a month for a long time. We have periods where we can't receive or make calls, can't sign in, or whatever. Sometimes they are related to certain numbers not being able to call. Support is almost nonexistent in tracking down issues like this.


Don't get me wrong - Teams is doing some really cool stuff with online meetings, but you guys can't just focus on the shiny stuff; you need to make the basic things work, too. The top 5 UserVoice requests are YEARS old, and in a couple cases the status has actually regressed.


These are some of the reasons to "why wait".


Teams still cannot replace our simple VC workflows, where we connect to publicly hosted virtual meetings hosted by Pexip for example. Until this is fixed we will stick for s4b for all Voice and Video

Senior Member

@Nydia Cavazos is there a PowerShell available to enable "Notify Skype for Business user that an upgrade to Teams is available?" For example, enabling for a group of users instead of whole tentant all at once. 

Regular Contributor

@ShareGuru It's the same command you use to change the coexistence mode: Grant-CSTeamsUpgradePolicy . Just choose one of the coexistence modes that ends with WithNotify, e.g. IslandsWithNotify instead of Islands.


Thank you, @Ryan Steele !

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‎Jan 26 2021 10:41 AM
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