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As Microsoft officially ends support for Skype in 2025, Microsoft Teams has become the go-to platform for communication and collaboration within businesses. Migrating from Skype to Teams, particularly in larger organizations, requires careful planning, configuration, and execution. This guide will walk through the essential steps and technical considerations for administrators in the migration process.

While Skype revolutionized real-time communication, it lacks some critical features required by modern businesses. Microsoft Teams extends beyond chat and calling; it is an all-in-one collaboration suite that integrates with Microsoft 365 applications, including SharePoint, OneDrive, and Outlook. Teams also provides robust enterprise security and compliance capabilities, making it the ideal successor to Skype.

Additionally, Skype for Business is being phased out, and Microsoft Teams now supports business-critical functionalities such as:

• VoIP calling

• Meetings and video conferencing

• Advanced file sharing and collaboration

• Tight integration with the Microsoft 365 ecosystem

Steps for Migrating from Skype to Microsoft Teams

1. Preparation and Assessment

Before starting the migration, a comprehensive Skype usage assessment should be conducted. Administrators need to identify the features being used, such as:

• Chat and messaging

• VoIP calling and conferencing

• Presence information

• Screen sharing and file sharing

Once this assessment is done, the next step is to determine the necessary Teams configurations that will meet these needs. It’s also crucial to ensure that the Teams licensing aligns with your organization’s requirements, as different Teams plans offer varying levels of access to features like calling, meetings, and collaboration.

2. Teams Configuration

To configure Microsoft Teams for your organization, you must enable Teams in the Microsoft 365 Admin Center and set it as the default communication platform. This involves:

• Configuring Teams policies for messaging, meetings, and calling.

• Enabling features such as Teams Calling Plan, Direct Routing, or Operator Connect for VoIP services.

• Setting up Security & Compliance Center policies for data retention, eDiscovery, and legal hold for Teams communications.

• Integrating Azure Active Directory to manage user authentication and access to Teams resources.

For organizations that previously relied on Skype for Business, you’ll need to manage coexistence modes, which dictate how Skype and Teams will interact during the transition. The coexistence modes include:

• Islands Mode: Skype and Teams operate independently.

• Teams-Only Mode: All communication occurs exclusively through Teams.

• Skype for Business-Only Mode: Skype is the primary platform, with Teams disabled.

3. User Migration and Transition

Once Teams is configured, it’s time to start the migration of users and data. Microsoft offers Skype to Teams Migration PowerShell Scripts and the Microsoft Teams Upgrade PowerShell Module to help automate the migration process. Key tasks during the migration include:

• Migrating user chat history from Skype to Teams

• Migrating users from Skype for Business Online to Teams

• Ensuring all user profiles are updated in Active Directory

• Transferring group chats, scheduled meetings, and file shares.

A phased migration approach is often recommended, where users can operate both Skype and Teams simultaneously (using Teams Only or Skype for Business modes) until all users are transitioned.

4. Configuring Teams Calling

If your organization relies on Skype for Business calling features (e.g., PSTN calls, voicemail, etc.), you will need to configure Teams to support Teams Calling Plans, Direct Routing, or Operator Connect. This involves:

• Purchasing and assigning Teams Calling Licenses for users who require external calling.

• Setting up Direct Routing with a Session Border Controller (SBC) if you’re using your own telephony infrastructure.

• Configuring Teams Calling Policies for call forwarding, voicemail settings, and emergency calling.

5. User Training and Adoption

User adoption is critical for the success of the migration. Administrators must ensure that training materials and resources are available for end users to get acquainted with Teams. Microsoft offers Teams Training and Adoption Guides that can help users transition seamlessly. Key features to train users on include:

• Navigating the Teams interface for chat, meetings, and file sharing

• Understanding the difference between Channels, Teams, and Private Chats

• Configuring Teams notifications and managing user presence

• Sharing files and collaborating using OneDrive and SharePoint within Teams.

6. Testing and Validation

Before completing the migration, it is crucial to test key functionalities, including:

• Call quality and reliability for VoIP and video conferencing

• Message and file synchronization between Skype and Teams

• Meeting scheduling and calendar integration with Outlook

• Compliance and security controls to ensure data protection policies are met.

Testing should be done with a small group of users first, to identify any issues before rolling out Teams organization-wide.

7. Decommissioning Skype

Once Teams has been fully implemented, and all users have transitioned, you can begin the process of decommissioning Skype. This includes:

• Disabling Skype for Business services

• Archiving Skype data according to company compliance policies

• Ensuring that users no longer rely on Skype for communication and collaboration.

Key Technical Considerations for Admins

• License Management: Ensure the correct Microsoft 365 licenses are assigned to users based on the features they require (e.g., Teams Calling Plans, Office 365, Enterprise Mobility + Security).

• Bandwidth Requirements: Teams calls and video conferencing may require significant bandwidth, especially with larger teams. Ensure your network infrastructure is prepared to handle Teams traffic.

• End-User Experience: Teams offers a richer collaboration experience than Skype. It’s crucial to monitor the end-user experience and optimize configurations for performance and usability.

• Compliance and Security: Teams offers advanced compliance features like information barriers, retention policies, and legal hold. Make sure these are configured according to your organization’s compliance needs.

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