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Microsoft Teams vs Skype for Business: Preparing for your Skype for Business upgrade and migration

When Microsoft Teams was first rolled out, Microsoft announced that Skype for Business would be retiring—and now we have a timeline: July 31, 2021. How should organizations start planning for this transition? And can Teams and Skype for Business coexist in the interim?

According to a recent Forrester study, shared workspaces like Teams can save users time—from one to eight hours per user per week, depending on their role. The wins from making the Skype for Business upgrade to Teams are clear: faster, more efficient working and collaboration.

And now businesses have another reason for migration that increases that urgency: a firm timeline for when Skype for Business will finally be phased out. This past July, Microsoft announced they'd be "retiring" Skype for Business Online on July 31, 2021. As of September 2019, all new Office 365 customers are onboarded directly to Microsoft Teams—the new default for chats, calls, and meetings.

Now that the clock's well and truly ticking, the ShareGate team has had to start thinking seriously about our own migration from Skype for Business Online to Teams—especially as we developed ShareGate Apricot, our Microsoft Teams management tool.

So how should you approach the transition? And how can Teams and Skype for Business coexist in the interim? Read on for some key advice on making the move.


Microsoft Teams vs Skype for Business

Some may be wondering what the big deal is. You may be thinking: "Why shouldn't I just delete Skype for Business and start using Teams instead?" Here's the official line from Microsoft:

Upgrading from Skype for Business to Teams is more than a technical migration. It represents a transformation in how users communicate and collaborate, and change is not always easy. The ideal upgrade approach should address the technical aspects of your upgrade as well as encourage user acceptance and adoption of Teams, driving a positive user experience and business outcome realization.

Official Microsoft documentation

Although Teams takes much of its DNA from Skype for Business, the two are very different solutions. When you put them side-by-side—Microsoft Teams vs Skype for Business—you'll see that Teams offers much more, bringing together files, chats, and apps in one place for a more complete, integrated collaboration solution.

For the purposes of this article, we’ll often use Microsoft’s term “upgrade”, but it doesn’t entirely reflect what a big change this will be. Teams is an entirely new tool, not the “next version of Skype for Business.”

For Microsoft Teams adoption to be smooth and successful, your people will need to learn what it actually is and how to use it. This is why a planned migration journey—rather than simply “flipping a switch”—is necessary.


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Skype for Business upgrade journey: Two methods

As an existing Skype for Business customer, the full transition to Teams might take a bit of time. Luckily, the overlapping capabilities of the two apps mean you don't have to do it all at once—there are a few different coexistence and upgrade modes to consider when deciding on your personal path to migration.

Administrators manage their transition using the concept of mode, which is a property of the TeamsUpgradePolicy cmdlet:

Grant-CsTeamsUpgradePolicy
     [-Identity] <UserIdParameter>]
     [-PolicyName] <string>
     [-Tenant <guid>]
     [-Global]
     [-MigrateMeetingsToTeams]
     [-Confirm]
     [<CommonParameters>]

Coexistence mode lets you configure the user experience—such as where incoming calls and messages will land, and which service new meetings will be scheduled in—and governs which functionalities you want to make available in Teams.

Users who have been fully migrated to Teams are considered to be in "TeamsOnly" mode, with the ultimate goal being migration of all users to TeamOnly mode.

Whether you're migrating from Skype for Business Online or on-premises, there are two methods of migrating to Teams:

  1. Overlapping capabilities method (using Islands mode) means that users in your Skype for Business organization are introduced to Teams and use both side-by-side during the transition period. They are provided with most of the Microsoft Teams functionality and are able to familiarize themselves with it and adopt the platform. Islands configuration is the default mode of any existing organization with Skype for Business, and this mode can be used until the migration is complete. Then the administrator can move users to TeamsOnly mode.
  2. Select capabilities (using one or more Skype for Business modes) means the administrator must personally manage the transition of individual chat, calling, and meeting scheduling functionality for their users—making each switch when the users are ready, via TeamsUpgradePolicy. Admins manage the transition by progressively migrating more and more users into TeamsOnly mode. Users who are not yet in TeamsOnly mode will continue to use Skype for Business for their chats and calling and will communicate with users already on Teams using inter-op functionality, which will be available in the first quarter of calendar year 2020.

For full details on how to implement these two methods, you can read Microsoft’s article on choosing your upgrade journey from Skype for Business to Teams.

The aim is to make this transition less of a battle of Microsoft Teams vs Skype for Business and more of a smooth handover from one tool to the other. We recommend a pilot is conducted to judge which of the methods will work for your organization.


Migration from Skype for Business Online to Teams

The entire upgrade process begins with good planning. To ensure success in the long-term, you need to leave yourself time to prepare beforehand. And that means creating an upgrade plan with clearly defined stakeholders and goals.

Microsoft has created an upgrade success framework for planning your migration from Skype for Business Online to Teams: a series of steps they suggest following, in order, to successfully implement your upgrade in stages.

There’s a lot of information available to help you make the change, so to simplify things, we’ll run through some of the main points and best practices here.

When planning for your migration, you should consider and define your:

  • Project stakeholders
  • Project definition
  • Technical readiness
  • User readiness
  • Deployment and implementation
  • Operational excellence

Project stakeholders

Ensure that all the right stakeholders are involved from the get-go. Microsoft recommends assigning two key groups of stakeholders:

  1. A sponsorship coalition: This includes executive and business sponsors, as well as project managers, all of whom have a vested interest in (and influence on) the project's ultimate success.
  2. The project team: These are the people responsible for ensuring technical and user readiness, as well as actually carrying out the tasks laid out in your project plan.

Make sure everyone knows their roles and responsibilities, and assign project team members to be accountable for driving the success of the upgrade.

Project definition

Have you defined the scope of the project, the end goals, and how you’ll measure its success? What is the situation right now, and what will it be at completion? What level of Teams adoption and deployment have you already reached? What method will you use for your Skype for Business upgrade to Teams?

It's important to define your project vision and scope at this point, as well as identifying potential risks and establishing a mitigation plan to get you back on trick if issues arise in the process. From there, you can design a timeline for your upgrade, and choose the appropriate coexistence strategy to employ.

For more info Skype for Business and Teams interoperability and the different upgrade journeys available to you, check out the official Microsoft documentation.

Technical readiness

Once you have a blueprint for your upgrade, you still need to prepare for it by evaluating your organization's readiness for Teams.

Can your IT staff manage the migration from a technical standpoint? Does your environment meet the requirements for Teams? Are your network and endpoints ready? How will you configure Teams for your end-users?

It's important to assess your current network and environment, and prepare your IT staff for the pending transition. If you're going to be deploying audio, video, or meetings, that might mean taking some extra steps to optimize your network for that functionality.

And make sure your IT technical and support staff have everything they need to support the technical environment of Teams.

User readiness

How do your people handle change? What value does Teams adoption offer the individual user? Which key people or types of teamwork will benefit most? What will you offer in terms of communication, training and support channels? Will you build a Champions program?

Prepare a user readiness plan that provides users with proper training; that way, you'll reduce confusion and boost user adoption of Teams when it's eventually deployed.

Deployment and implementation

Will you run a pilot? If so, define its participants, timeline, and goals. How will you gather feedback and network stats? Decide how you'll assess learnings and analyze success of the pilot against your goals.

You also need to determine a 'go-forward' plan: how will you evaluate whether to expand the pilot into a wider deployment? And how many users will you migrate at once as part of that wider deployment?

Microsoft recommends deploying Teams in coexistence with Skype for Business Online at first. That way, users have a chance to get familiar with the new tool and IT is eased into the transition gradually.

Make sure you follow the correct steps to set the right coexistence modes for your organization.

Operational excellence

When you do decide to officially upgrade—moving your users into Teams only mode and disabling access to Skype for Business—consider the effect the change might have on the user experience.

Allow users enough time to transition all their activities from one app to another. Microsoft recommends limiting the official transition period to around 45 days in order to limit confusion.

But before fully flipping the switch, have you thought about how you'll measure the success of the migration and manage day-to-day service operations after deployment? What’s your plan to grow Teams adoption throughout your business? And how will you promote and maintain effective use of Teams over time?

Microsoft’s Coffee in the Cloud YouTube channel includes a video that explores this topic in greater depth: Plan your upgrade from Skype for Business to Microsoft Teams. It’s useful viewing for anyone planning the change.


Governance at every stage of planning

Whether you're undergoing a Skype for Business upgrade, or just getting ready for your Teams deployment, we can't stress enough the importance of planning for governance beforehand.

The good news? If you followed the upgrade framework outlined above, then you're already using a governance mindset at each stage of planning—from user education to official implementation. IT governance is just a formal framework to help organizations ensure that its IT investments support its business objectives.

Now that you've already started thinking about governance, why not consider other aspects—like creating an effective naming policy, or devising a way to stay on top of inactive teams and groups—that will help keep your tenant organized and secure long past the moment of deployment?


In today’s digital workplaces, sharing content is an important piece of the collaboration puzzle—especially when working with clients, vendors, or anyone else outside your organization.

Download our latest eBook, Sharing is caring: A ShareGate guide to creating a productive and secure guest sharing environment in Microsoft Teams, to learn how you can leverage the power of self-service to keep sensitive data secure.

book cover sharing is caring

Secure collaboration in Microsoft Teams—without limiting productivity.

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