Skype is Retiring. How to Upgrade to Microsoft Teams.

When was the last time all of your employees were physically together in the same room? 

Maybe your employees work from home as-and-when required; perhaps you have a handful of remote employees, or maybe you’re a geographically distributed business with offices in multiple locations. 

Today, countless businesses rely on communication and collaboration tools to keep their employees connected to one another, and to third parties such as customers. 

There’s no shortage of communication tools on the market, but Skype is one of the most popular - and it’s being discontinued!

If you’re one of the many businesses who rely on Skype, then Microsoft recommends that you upgrade to Microsoft Teams, and that you start the upgrade process now. 

In this article, we share a clear, step-by-step plan for how your business can migrate from Skype for Business Online, to Microsoft Teams. By working your way through each phase, you’ll be able to deploy Teams across your business with minimum disruption, and then optimize your Teams environment to ensure you’re getting the most out of your new communication tool.

Phase 1: Pre-Upgrade

Skype for Business Online will be discontinued in 2021. While this may seem like a generous deadline, your communication and collaboration tool is crucial for keeping everyone connected and productive in the workplace, so you’ll need to plan and execute your migration carefully - and successful migrations don’t happen overnight! 

In this pre-upgrade phase, you’ll need to plan every part of your migration, including building your upgrade team, defining project goals, setting a timeline and clarifying your overall project vision. 

Step 1: Build your team 

Your stakeholders will be responsible for driving the project, and are therefore critical to your business successfully migrating to Microsoft Teams. 

As a minimum, you should create the following stakeholder groups, which should include representations from both business and IT: 

● A sponsorship coalition. This should include executive and project sponsors who have a vested interest in the project’s success. 

● An executive sponsor. This will typically be a senior manager or executive who will act as the final decision-maker, and has the authority to hold others accountable. 

● The project team. These people will be responsible for ensuring technical and user readiness, and for executing your project plan. 

● A project manager. This person will ensure that tasks get completed on time, and will report back to the sponsorship coalition. 

Depending on the size of your organization, you may also want to create a steering committee who will be responsible for coordinating the various stakeholder groups.

Step 2: Define your project vision

This is where you focus on the “big picture.” 

What exactly do you hope to achieve by migrating to Microsoft Teams? Perhaps you want to eliminate legacy technology; maybe the migration will form part of your digital transformation initiative; or perhaps you want to cut your corporate spending? 

When defining your project vision, it can help to focus on the challenges you’re experiencing with your current communication and collaboration tool. How is Skype holding your business back? And what are the tangible, measurable benefits you’d anticipate, if you successfully overcame all of these challenges? 

Step 3: Set some goals

How will you know that your migration was a success? 

In this stage, you should define clear objectives and key results (OKRs), and key success indicators (KSIs). For example, an OKR might be to successfully pilot teams alongside Skype for Business, and the KSI could be to achieve a 75% satisfaction rating from pilot participants. 

Migrating from Skype to Teams is a multi-step process, so you should define a mix of short-term and long-term OKRs and KSIs. By continuously monitoring the success of your project, you can identify issues as they occur, and make any adjustments that are necessary to keep your project on track. 

Step 4: Create a risk mitigation plan

If your migration is going to be a success, then you need to prepare for the worst case scenario. By creating a risk mitigation plan, you’ll have measures in place to overcome any obstacles that you may encounter along the way. 

Once you’ve identified a risk, you should consider logging it in a formal risk register. For each risk, you should record the following information: 

● The likelihood of encountering this risk. 

● The impact it would have on your migration. 

● Your mitigation plan for overcoming this risk, and getting your project back on track as quickly as possible. 

Step 5: Create a timeline

To help keep your project on track, you should define a timeline and assign a completion date to each of your short-term and long-term goals. 

Phase 2: Define a Skype for Business and Teams coexistence strategy 

For most businesses, abruptly switching your entire workforce from a purely Skype environment to Microsoft Teams isn’t practical, or even advisable! Instead, you should plan for an interim period where your staff use Teams alongside Skype for Business Online, as this gives them the opportunity to explore Teams’ features while retaining access to Skype. 

This kind of staggered rollout can also take the pressure off your IT department, and give you the opportunity to address questions, concerns or issues as they emerge slowly over time. 

Microsoft offers several “coexistence modes” where you run Skype and Teams side-by-side, so you can choose the approach that makes the most sense for your business. For a detailed breakdown of the various coexistence modes, check out Microsoft’s coexistence and interoperability guidelines

Phase 3: Is your business ready for Teams?

During this phase, you should gauge whether your organization is ready to implement Microsoft Teams, by evaluating technical readiness and user readiness. 

The good news is that there’s plenty of steps you can take, to help Microsoft keep your data safe.

Step 1: Evaluate your technical readiness

You should determine whether your technical infrastructure can support Microsoft Teams, by performing a detailed environment discovery, including an in-depth network assessment. If you identify any difficulties or potential blockers, then you can incorporate this information into your risk register, or adjust your migration plan if necessary. 

You should also take this opportunity to optimize your network, particularly if you’re a large enterprise, have known network limitations, or plan to deploy audio, video or meetings. For more detailed advice on how to optimize your network, check out Microsoft’s Office 365 Network Connectivity Principles

Step 2: Prepare a user readiness plan

Upgrading to Teams is more than just a technical migration! If your migration is going to succeed then your employees need to be completely on-board with the move to Microsoft Teams. 

In this step, you should identify and analyze all the different communities who will be impacted by the migration, and determine how receptive they are to adopting Teams. You can then use this information to define how you will communicate, train and support each group of users, in order to proactively address their concerns and encourage them to view the migration as a positive, rather than an inconvenience. 

When communicating with your employees, it often helps to use a combination of universal messaging, such as generic use cases, and messaging that’s tailored to each specific user group, as this will help individuals visualize how Teams will benefit them.

Step 3. Announce the impending launch of Microsoft Teams  

By making your announcement early, your employees will feel more included, and they will have ample opportunity to ask any questions, or raise any concerns they may have regarding the planned upgrade.

Phase 4: Put your plan to the test  

Next, you should pilot your migration plan with a select group of participants. A pilot program can help you identify any areas of difficulty or potential blockers, and provide data that you can use to refine your migration plan. 

Step 1: Define your pilot logistics 

Your pilot should have clear start and end dates, goals for measuring success, and test scenarios. 

When defining your pilot logistics, it may help to liaise with stakeholders and department managers, to identify real projects and tasks that you can use in your pilot. 

By using real-world projects and tasks, you can test Teams in a way that’s relevant to your business, rather than testing theoretical, generic scenarios that your employees may never encounter in their day-to-day work. 

Step 2: Create a communications plan

While the pilot is in progress, you should stay in close contact with all participants, rather than automatically assuming you’ll receive useful post-pilot feedback. In addition, all pilot participants need a communication plan for requesting any additional information, training or support they may require as they progress through your pilot. 

Step 3: Create post-pilot resources  

Ideally, your pilot will generate a wealth of information that you can use to refine your migration plan - so you need to make sure you capture this information! 

Before launching your pilot, you should create all the surveys, feedback forms, and any other resources you’ll use to gather information from participants after they’ve successfully completed your pilot.

Step 4: Inform pilot participants

You need to ensure that each pilot participant understands exactly what the pilot will entail, when it will take place, and what’s expected from them. You should aim to inform participants about the pilot as early as possible, as this will give them the opportunity to ask questions and raise any concerns they may have. 

Step 5: Run your pilot program  

You should be constantly gathering data throughout the duration of your pilot, for example you might monitor network usage, review any support queries relating to Microsoft Teams, and keep in close contact with pilot participants. By monitoring your pilot, you can adjust it on-the-fly, to ensure you get the maximum value from your pilot scheme.

Step 6: Was your pilot program a success?

Now’s the time to gather all the data and analyze it against the goals you defined during the pilot logistics stage. 

If you’ve achieved all your goals, then you should typically progress to the next phase. If you haven’t met all the goals defined in your pilot logistics, then you should address any areas of concern or blockers, and then schedule a follow-up pilot. 

Phase 5: Upgrade

It’s finally time to upgrade to Microsoft Teams! The steps will vary depending on your migration plan, but as a general outline you should: 

● Notify your employees that you’re commencing the upgrade, and keep them informed throughout the upgrade process. 

● Start deploying Microsoft Teams features without disabling Skype for Business. To avoid broken communication, you shouldn’t remain in this coexistence mode for longer than 45 days. 

● Drive Microsoft Teams adoption until it’s saturated across your organization. 

● Once everyone is using Teams, you can perform the technical migration by switching to Teams Only mode, and then disabling Skype for Business Online. 

Phase 6: Post-upgrade

Congratulations, you’ve successfully migrated to Microsoft Teams - but we’re not finished yet! This is the perfect opportunity to ensure you’re getting the most out of your new communication and collaboration tool. 

To optimize your Teams experience: 

● Evaluate your upgrade against the goals you established during the pre-upgrade phase, and define a course correct strategy for any goals that are still outstanding. 

● Monitor the quality of your network to identify any opportunities to improve the user experience. 

● Keep the momentum going! Continue gathering employee feedback, including monitoring any support tickets that relate to Microsoft Teams. You can use this information to continuously evaluate and improve how your business is using Teams, which will reduce the chances of employees slipping back into their old ways of working. 

● Prepare to implement Teams’ upcoming features and improvements by establishing a change release cycle based on Microsoft’s roadmap - make sure you include technical and user readiness activities in your change planning form! 


Do you want to find out more about Microsoft Teams, before migrating from Skype? Or do you want a helping hand, to ensure your migration runs as smoothly as possible? You can book a free, one-on-one consultation with our specialist engineers, who will be happy to answer any questions you may have regarding Microsoft Teams, and explore what this change may mean for your business. 



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Speak to a member of our team today 0114 292 2911 or email sales@systemsassurance.com if you need any assistance.

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