Communication is the lifeblood of every business, from simple chat messages through to video calls and conferences. Microsoft continues to drive the way in which business communications are conducted, as its leading Skype for Business product slowly transitioning to Microsoft Teams. When Teams was first made available, Microsoft announced that Skype for Business would be retiring. Now, we have an end-date: July the 31st, 2021.

How should your organization start planning for this transition? In the meantime, can Microsoft Teams and Skype for Business coexist, or do you need to make a choice?

Microsoft Teams vs Skype for Business

Skype for Business extends the capabilities of Skype to support the communication needs of modern businesses. It supports chat messages, voice calls, and video conference calls for up to 250 people. In addition, users can transfer calls and dial using a real phone number if the other person isn’t online. Across the board, Skype for Business has proved itself as a robust and highly useful communications tool.

While Microsoft Teams offers similar capabilities, it was designed specifically as a collaboration tool to enhance business productivity. Skype for Business is primarily a communications tool, but Teams offers better integration with other Microsoft products and a deeper collaborative environment for group work. While there’s a significant overlap in functionality, the design philosophy is very different.

Microsoft Teams is full of integrated external apps and collaborative features which leverage the power of the Office 365 package. As the leading global provider of office applications and productivity tools, Microsoft is in a unique position to design communications software that integrates seamlessly with the rest of its product range. Teams takes your business’ communication to the next level and is intended to be a platform on which you can communicate and collaborate, but you can also build productivity scenarios and tools. Additionally, the platform is designed to enhance data safety and security through Microsoft’s strict enterprise-grade compliance and security.

Microsoft Teams vs Skype for Business: No need to choose yet!

As advertised, Microsoft Teams will take over from Skype for Business as Microsoft’s internal communications and collaboration platform. However, organizations are not required to make the move for the next 18 months. If you are using Office 365 for your business, however, making the transition to Microsoft Teams as soon as you can is definitely advised.

If you’ve decided to migrate now, or are planning to migrate soon, it’s important to differentiate between the following two Skype products:

Skype for Business Online

Skype for Business Online is already getting ready to end on the 31st of July, 2021. During the lead-up period, existing features will be supported but no new features are likely to be added. While Microsoft Teams is not a direct replacement for Skype for Business, customers will be expected to make the move when Microsoft disable their support.

Skype for Business Server

In contrast, Microsoft has committed to its Skype for Business Server product for many years to come. This software service provides infrastructure for enterprise messaging, presence, VoIP, ad hoc and structured conferences, and PSTN connectivity among others. Skype for Business Server continues to see enhancements on a regular basis, with the following new features added in February 2019:

  • Cloud Voicemail
  • Call Data Connector
  • Side-by-side migration

However, the below features were announced as end-of-life for Skype for Business Server last November:

  • XMPP Gateways for Skype for Business Server
  • Persistent Chat for Skype for Business Server (functionality available in Teams)
  • SQL Mirroring for Skype for Business Server
  • In-place upgrades
  • Mobility Service (Mcx)

Why is Microsoft transforming to Teams?

As Microsoft continues to focus on collaboration, they want to provide businesses with a single platform for teamwork. Future updates to Teams will combine the business communications of Skype for Business with the collaboration tools, sharing capabilities, and app integration of Microsoft Teams. The use of collaboration and cloud infrastructure will create new opportunities for communication and allow users to make better use of their resources and time.

How to prepare for the Skype for Business transition

Microsoft wants all Office 365 users to start using Teams together with Skype for Business while they get accustomed to the Teams platform. Once you are ready to move fully to Teams, they’ve come up with two separate upgrade paths to help with your migration:

If you are an existing Skype for Business customer, your complete transition to Teams might take some time. However, you can begin exploring the value of Teams today by using Teams alongside Skype for Business.

Given the overlapping functionality between these two apps, it’s important to review how they work together in order to solidify your upgrade paths and determine which path is right for your organization.

Two methods

There are two methods for migrating from Skype for Business to Microsoft Teams:

  • Overlapping capabilities method, which uses Islands mode – In this mode, existing users in a Skype for Business organization are introduced to Teams during a transitional phase. During this period, most of the functionality of Teams is made available. This mode is known as Islands and is the default mode for any existing organization with Skype for Business.
  • Select capabilities method, which uses Skype for Business mode – In this mode, the administrator manages the transition of chat, calls, and meetings for users in the organization. Each of these functions is available, and administrators control when the shift occurs. Users can continue to use Skype for Business for chat and calling, and administrators manage the transition by progressively migrating more users into Teams.

Microsoft has created an upgrade success framework for planning the migration process from Skype for Business Online to Microsoft Teams. The following steps are suggested in order:

1.         Identify project stakeholders

2.        Define project needs

3.        Assess technical readiness

4.        Assess user readiness

5.        Carry out deployment and implementation

6.        Refine plan to ensure operational excellence


What to expect when transitioning from Skype to Teams?

Moving from Skype to Teams is truly an evolution for organizations and involves a learning curve from the end-user perspective as the user interface (UI) is quite different. If you are going through this transition, make sure you have a good adoption and change management plan in place to be able to train your staff and roll out this new way of working.

Additionally, you might need to plan for internal support as many questions will arise from your users (e.g.: I used to be able to do this in Skype how do I do this in Teams? Why doesn’t this work the same way in Teams vs. Skype? Etc.)

Want to learn more about Microsoft Teams? Get a Teamwork assessment.

Softlanding specializes in professional and managed IT services for demanding businesses. As a multi-award-winning Microsoft Gold Partner, we can manage the implementation of Teams and other Microsoft solutions. Whether you’re just starting out with Teams or making the transition from Skype for Business, we can analyze your communications needs and find efficient new solutions that work for your organization.

Contact us if your want to learn more.

Written By:

Caroline Blivet

As Softlanding's Marketing Lead, Caroline and is responsible for driving lead generation, developing a go-to-market strategy and, delivering marketing campaigns. Outside of work, Caroline enjoys hiking the beautiful trails of British Columbia.

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