Upgrade Pro

Designed for larger organizations or those with complex deployments of Skype for Business (for example, hybrid or cloud voice deployments), Upgrade Pro accounts for a longer upgrade lifecycle along with a variety of upgrade scenarios, including running Microsoft Teams alongside Skype for Business until Teams is ready for your organization.

Segmented into three phases, Upgrade Pro covers:

Pre-Upgrade Upgrade Post-Upgrade
Realize the value of Teams
  • Ready your environment
  • Adopt Teams for collaboration, meetings, and/or calling
  • Plan for your Skype for Business to Teams upgrade over time
Migrate users from Skype for Business
  • Notify and ready your users
  • Move users into Teams-only mode
  • Track usage progress against goals
Amplify your ROI
  • Monitor your network health/quality
  • Maintain user excitement
  • Plan for ongoing Teams innovation


We understand that your journey to Teams might involve leveraging multiple modes and upgrading groups of users at different times, which will enable you to control the user upgrade experience while maintaining momentum with Teams.

To help demonstrate how your upgrade journey might unfold, we’ve provided a sample plan below that defines a journey going from Skype for Business to Islands mode to Teams only. In addition, the sample plan outlines an organization that has divided their users into four upgrade groups, or cohorts. Using this as a template, customize the plan to encompass your specific journey to Teams, incorporating the various modes you’ll use and the number of upgrade groups you’ll segment your users into.


Prepare your organization for Teams. To help ensure a successful upgrade to Teams, it’s important to allocate adequate time for preparation. Not only will your organization be able to quickly start realizing the value of Teams, you’ll be able to accelerate your upgrade from Skype for Business as soon as Teams is ready for you. Monitor the roadmap for the enhancements that are planned for Teams; this will help you identify the right upgrade timeline for your organization. If you’ve already enabled Teams alongside Skype for Business, use these pre-upgrade activities as a checkpoint to validate your organization’s readiness before you upgrade users to Teams.


Download the Upgrade Success Kit for template user readiness materials, such as communications and user surveys, in addition to a sample upgrade project plan and pilot test plan. Items that are available in the kit are marked with an asterisk (*) in the lists below.

Days 1–7: Create your upgrade plan to help ensure your organization is set up for long-term success

Step Summary Resource
1 Define your stakeholders Consider the scope of your project and identify the relevant stakeholders across technical readiness and user readiness to drive accountability and success. Enlist your stakeholders
2 Define your project vision Your vision is the “big picture” or eventual end-state that answers the question, “Why are we doing this project?” An ideal vision addresses your organization’s business drivers and user value-add perspectives. Project vision
3 Define your project scope Your vision might only be realized over time, through various phases. The project scope defines the focus of your project at this time and serves to keep your project team focused on their current tasks, enabling you to realize your long-term vision. Project scope
4 Define your project goals Your goals define the outcome you want and enable you to measure the success of the project. Goals can be defined as objectives and key results (OKRs), and the measures of project success can be defined as key success indicators (KSIs). It’s essential that you get full participation from project stakeholders in defining OKRs and KSIs, to help ensure they feel a sense of ownership and align these measures of success to defined project tasks. Goals should include a mix of technical and user-focused success. Project goals
5 Identify risks and mitigation plans It’s important to proactively assess potential risks and define a mitigation plan for overcoming the issues that might arise, so your project can continue toward your goals. A risk register is an excellent tool for tracking project risks—along with how likely they are and their potential impact—and capturing your mitigation plan. The following table shows a sample risk register. Risks and mitigation
6 Define your timeline Set a timeline for key milestones (for example, enabling Teams alongside Skype for Business for all users or starting phased upgrades of users) in addition to the completion date. A defined timeline helps your project team drive toward a consistent end state and informs the right work-back schedule, helping to ensure that your project stays on track. Consider a timeline that’s not too accelerated (where tasks might be list). Timeline

Upgrade Success Kit
7 Define the appropriate Skype for Business and Teams upgrade and coexistence strategy As an existing Skype for Business customer, your complete transition to Teams might take some time. However, you can begin realizing the value of Teams today, by enabling your users to use Teams alongside Skype for Business. Given that there’s some overlapping functionality between the two apps, we recommend that you review the available coexistence and upgrade modes to help determine which path is right for your organization. For optimal experience, pilot your planned coexistence strategy before deploying broadly to all users. Understand Microsoft Teams and Skype for Business coexistence and interoperability

Choose your upgrade journey

Days 8–15: Evaluate your organization’s readiness for Teams

Step Summary Resource
1 Evaluate your existing environment to identify risks and requirements By evaluating your environment, you identify risks and requirements that will influence your overall deployment. By identifying these items proactively, you can adjust your planning to help ensure success. Evaluate your environment before upgrading to Teams
2 Complete Office 365 and Teams technical onboarding Leveraging existing onboarding checklists to identify tasks and activities to complete technical readiness for collaboration and voice capabilities with Teams. Prepare your service for upgrading to Teams
3 Optimize network for Teams, particularly for real-time media scenarios If you’re deploying audio, video, or meetings, you can take some additional steps to optimize your network for that functionality. Teams uses audio and video technology (codecs) that can adapt to—and therefore perform better under—most network conditions. To ensure optimal and consistent performance, you should prepare your network for Teams. Prepare your network for upgrading to Teams
4 Assess organizational change readiness To realize value from Teams, users must actually use it. Simply enabling Teams doesn’t guarantee that you achieve your goal. Users have different use cases and varying learning styles, and they adapt to new technology at different speeds. Understanding your user base enables you to prepare the right level of education to facilitate and accelerate user adoption. Organizational change readiness
5 Prepare a user readiness plan to define how you will communicate, train, and support users To ensure optimal receptiveness to the new technology, use a combination of broad-reach messaging (incorporating the vision/value messaging and universal use cases) and messaging, training, and support tailored to the personas and cohorts you’ve defined and also to your laggards, as appropriate. This personalized plan will help facilitate user adoption by enabling users to more quickly relate to Teams, while demonstrating that you understand their needs. This can be used as you pilot, onboard, and upgrade to Teams. Prepare a user readiness plan

Upgrade Success Kit

Teams video training

Switch to Teams from Skype for Business
6 Announce the pending launch of Microsoft Teams Communicating with your users early helps users feel included, reduces confusion generates excitement about Microsoft Teams, helping accelerate the upgrade from Skype for Business over time. Upgrade Success Kit
7 Prepare your IT staff for Teams Your Office 365 tenant admins, technical leads, and support desk are accountable for driving a high-quality user experience. This includes ensuring that your network is ready to support Teams, configuring Teams for your users, and being able to effectively troubleshoot and resolve issues that might arise. Prepare your IT staff for Microsoft Teams

Upgrade Success Kit

Days 16–60: Run a pilot to confirm that your organization is ready and inform your optimal journey to Teams

Step Summary Resource
1 Outline pilot logistics A successful pilot has defined start and end dates, and clearly defined goals for measuring success. These goals should align with the scope of your broader project and will be used to inform your path forward after your pilot is over. Outline pilot logistics
2 Select your pilot participants and test scenarios Select pilot participants not solely based on roles or personas but also based on their project and cross-team work. The pilot should extend to key people in IT, training, and your helpdesk, so you can thoroughly validate the solution while fully optimizing project management resources Be sure to include top Skype for Business users. Select your pilot participants and test scenarios
3 Design your test plan and feedback survey Identify clearly defined tasks for participants to complete and a way for them to share their feedback. Group tasks together to offer real-world scenarios to your users, demonstrating relevancy to their daily activities. Design your test plan and feedback survey
4 Create your pilot communications plan Educate pilot participants on what’s happening, when, and why, and what’s expected of them. To drive excitement and maximum participation, be sure to include user value messaging in addition to links to training and support where users can get additional information as they progress through the pilot. Create your communications plan

Upgrade Success Kit
5 Conduct your pilot Conducting your pilot includes communicating with your users, monitoring your network and usage to ensure your network performance and call quality remain healthy, gathering feedback from participants, and reviewing helpdesk tickets for questions related to Teams. Conduct your pilot
6 Assess learnings and evaluate your go-forward plan Gather all feedback surveys, final network stats, and support tickets for analysis against your goals and determine whether you’ll implement your go-forward plan. Assess learnings and evaluate your go-forward plan

Day 60 until upgrade: Deploy Teams in coexistence with Skype for Business

Step Summary Resource
1 Announce the official launch of Teams Communicate with your users about the start your organizational launch of Teams to ensure awareness and land value and benefit with users. Consider multiple forms of communication including a launch event and email. Upgrade Success Kit
2 Enable the appropriate coexistence mode for your users Follow steps to set the right coexistence mode(s) for your organization. Setting your coexistence and upgrade settings
3 Stay informed about the Teams roadmap Monitor the Teams roadmap and continually assess organizational readiness to identify the right time for your organization to move to Teams. Teams roadmap
4 Send additional communications and engage Teams champions to drive excitement and adoption of Teams Encourage user adoption and maintain excitement for Teams with ongoing communications and Champions. Microsoft 365 Champions Program


Make the official move to Teams. When you upgrade your users, you move them into Teams only coexistence mode. Teams becomes their primary app for chat, meetings, calling, and collaboration, and access to the Skype for Business app is disabled. Although the technical aspects of this phase are quite simple, consider the effect the change might have on user experience and allow time for users to officially transition their activities from Skype for Business to Teams. To reduce users’ having different experiences with different clients, try to limit the end-to-end upgrade window to 45 days or so.

Days 1–45: Implement your upgrade from Skype for Business to Teams

Step Summary Resource
1 Validate that you’ve completed the pre-upgrade activities described above Help ensure your upgrade success by confirming completion of all planning and preparation activities. All the above
2 Initiate communications to users in your first upgrade group Start executing your pre-, during- and post-upgrade communication plan to drive awareness, set expectations, and share the benefit of Teams with users in advance of their upgrade. Prepare a user readiness plan

Upgrade Success Kit

Teams video training

Switch to Teams from Skype for Business
3 Enable the coexistence mode to Teams Only for users in your first upgrade group Follow steps appropriate to your Skype for Business environment to perform the technical user migration. Upgrade from Skype for Business Online to Teams

Upgrade from a Skype for Business hybrid deployment to Teams

Upgrade from a Skype for Business on-premises deployment to Teams
4 Repeat the preceding upgrade activities for the remaining upgrade groups on a rolling cycle Continue to drive your ongoing communications plan and upgrade user groups based on your plan.
5 Send post-upgrade feedback surveys to all users Leverage a feedback survey to capture feedback and insights from users. Upgrade Success Kit


Maximize business value with Teams. After your organization is fully upgraded to Teams, take time to evaluate your success against your goals and implement a plan to continue forward momentum.

Days 1–14: Measure the success of your upgrade

Step Summary Resource
1 Assess your initial upgrade success Evaluate progress against the goals you established in the pre-upgrade phase. Project goals
2 Implement a mitigation plan for any goals that aren’t on track. Define mitigation or course-correction strategies for goals that are not being met. Project goals


Step Summary Resource
1 Monitor for network health and quality Implementing a plan to monitor and mitigate network health will help ensure a positive user experience in addition to reducing calls to your support desk. Monitor for network health and quality
2 Drive user momentum and adoption Encourage user adoption and maintain excitement for Teams with an ongoing adoption plan. Drive user momentum and adoption
3 Prepare for new functionality Establishing a change cycle within your organization will ensure you’re ready to manage continual collaboration improvements and realize maximum value. Prepare for new functionality


Our Upgrade Pro content is continually evolving. Be sure to check back for the latest guidance, and read the Teams blog.


Skype for Business Online will be retired on July 31, 2021, after which it will no longer be accessible or supported. To maximize benefit realization and ensure your organization has proper time to implement your upgrade, we encourage you to begin your journey to Microsoft Teams today. Remember that a successful upgrade aligns technical and user readiness, so be sure to leverage the guidance herein as you navigate your journey to Microsoft Teams.