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8 Questions to Ask on Your Journey: Upgrading from Skype for Business to Microsoft Teams

By Mike Hanks -->

In our last post, we looked at nine questions you’d probably ask while planning your transition from Skype for Business to Microsoft Teams. Those questions were meant to highlight the end of life for Skype for Business Online on July 31, 2021 and make the case for why you should upgrade. This time around, we’ll be looking at questions that address what upgrading from Skype for Business to Teams should look like.


1) How do I know when my organization is ready for the change to Teams?

While it wouldn’t be incorrect to say, “you’ll know when you’re ready,” it’s a bit of a non-answer. The truth is, being ready for the change will look different for every person and every organization. 

Time for change One major sign that your organization is ready to make the change is when you notice that you’ve outgrown Skype for Business. Your teams are too wide and varied, spread too far around the world, and demanding a kind of working standard Skype for Business simply can’t live up to. This is an obvious sign that it’s time to make a change, but you might not want to wait until it’s gotten to this point to do so.

It would be best to make the transition when your organization wants to rather than when it needs to. If your users (especially the more influential ones) have already started to champion the idea of implementing Teams, it’ll be that much easier to make the change. That’s not to say that the process of changing communication methods on a fundamental level is simply a matter of “wanting it badly enough,” but it’s a good place to start. Identifying your key influencers to be “evangelists” for this transition will be priceless. 

Another sign that you’re ready to move to Teams? If your organization is prioritizing security, the cloud is the safest place to be. Teams is a cloud-only solution, whereas most Skype for Business users are utilizing an on-prem solution. There will be an extreme advance in technology in the next ten years, and these advances will be happening in the cloud. Make sure you’re there to take advantage of all those security benefits. 

The important thing to remember with the change to Teams is that there are two kinds of readiness: technical and business readiness. Though they function differently, each one is vital to the process, but there will be more on that later.

Questions about Skype for Business Online coming to End of Life?

Learn more about the transition from Skype for Business to Microsoft Teams

2) What does it mean to have Teams “be ready” for my organization?

It means nothing short of operational excellence. When Teams is ready for you, you’ll have all your users in one place, easy to contact and organized into various teams. It won’t happen overnight, but when it does, it’ll signify the end of your journey.

3) What should I do to prepare for my upgrade?

Preparing for the upgrade is an involved process in and of itself; one that we refer to as the “pre-upgrade.” It begins simply by gathering information. Identify important people, stakeholders, who will help the process along. Visualize the scope of the solution and all you’ll need it to do. Make sure to stay educated as well, so that you understand the upgrade and Coexistence Mode (temporarily utilizing both Skype for Business and Teams as a tool for on-ramping). 

Next you need to prepare. Get the environment and organization ready and make the big announcement that Teams will be launching soon. You’ll need to make sure that your help desk knows to be ready to support Teams. The help desk might wind up working harder than others, but it’s what must be done to make sure everything runs perfectly. During this process, it would be wise to host a launch event so you can set aside time to make sure everyone knows what’s going on and can get on board.Preparation and Planning

After that comes testing. Get a user pilot set up with Teams alongside Skype for Business. Let people see some of Teams’ features in action and get a chance to use it themselves. This is a great way to enlist key individuals to help spearhead user readiness. We can call these elites “Teams Champions”. This process will likely take the longest out of all of them, so be ready to spend up to a month piloting Teams.

Finally, it’s time to begin. Get your champions together, set the right coexistence mode, and you’ll be ready to start. As the upgrade begins in earnest, make sure to continue monitoring the Teams upgrade roadmap to make sure everything goes according to plan. While that goes on, feel free to send out messages to get your users anticipating something great. Switching to Teams can be an exciting event, and your users should be just as excited as anyone.

4) When should my organization upgrade from Skype for Business to Teams?

Given all the questions asked so far, there are two different ways this can be answered.

When should you begin the process or at least begin thinking about upgrading? You should make plans to take advantage of the many benefits of Teams as soon as you’re able. You may have heard it in the previous article, but Skype for Business’ days are numbered. With an official end of life date published, July 31, 2021, it would be unwise to wait until that date gets closer to begin the process. Do it sooner rather than later, so that you can take your time and make this transition with purpose and excellence. 

When should you begin the upgrade? For that, you’ll need to wait until the “pre-upgrade” is finished. Both the pre-upgrade and upgrade processes can take time, so be sure not to rush it. Once you’ve validated your completion of the pre-upgrade, you can move on.

5) How long will the transition to Teams take, from start to finish?

There’s a good chance it will take longer than you think. With so much to consider in terms of both business and technology, the time you’ll need to dedicate to the process could just as easily be measured in months as it could in days. 

It should take around 45 days to complete the pre-upgrade process, then another 45 to complete the actual upgrade. Additional time will be needed to monitor post-upgrade success, time to mitigate any potential problems or shortcomings, and time to acquire any necessary licenses. Chances are, the whole transition will take about four months.

A crucial part of this timeline is conducting a thorough network assessment to evaluate whether your back-end infrastructure can handle the video and network load of Teams. The results of this assessment will determine whether your road map will be shorter or longer and more involved.

6) How long should we stay in Coexistence Mode?

This is largely dependent on what kind of coexistence mode you choose. If your organization is struggling to let go of Skype for Business, you may need to utilize a coexistence mode with more features of Skype for Business than Teams, making that journey to Teams a little longer. 

Alternatively, if your organization is ready to kiss Skype for Business goodbye, you would then opt for a coexistence mode with mostly Teams features, or better yet, no coexistence mode at all. In this case, the process would be much faster.

7) How do I plan my upgrade process?

Start with a proven framework. Afterwards, you need only follow a series of steps:

Framework Meeting
  • Gather your team of project stakeholders. Such a team will likely include an executive sponsor, an IT pro, a Teams Champion, and two or three key individuals to oversee the project and user adoption.  
  • Define the project, taking into consideration the scope of the project, your baseline, your end goal, and your desired path.
  • Make sure your environment is technically ready.
  • Make sure your users are ready.
  • Implement your upgrade plan. Make sure you have a clearly defined pilot plan for your testing and upgrade strategy.
  • Operate and amplify your Teams adoption.

Remember, this isn’t simply a replacement for the calling and messaging functions of Skype for Business. Teams brings with it a whole evolution of communication, and it’s worth your time to consider how your organization can fully take advantage of everything that Teams brings to the table. 

8) How do I navigate this journey?

As with any other journey, you’ll need a map and a guide. The more in-depth and easier to follow your road map is, the better the transition will go. Fortunately, we at Continuant specialize in creating unique road maps to fit the needs of each individual customer, and we can function as the guide to effectively get you from the starting point to that all-important finish line.

Hopefully, more of your burning questions have been answered. If you have a different question that didn’t appear on this list, check out Part 1 and Part 3 of our FAQ series, or give us a call and talk to one of our Teams Deployment experts. 

Skype for Business End of Life

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