A Fresh Look at Skype for Business to Teams Migration

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Best Practices and Top FAQ’s for Migrating to Microsoft Teams 

Anyone looking to educate themselves on how to approach a Skype for Business to Teams migration will need patience, lots of caffeine, and the ability to objectively vet reams of data.  In addition to the myriad of Microsoft technical documents which have been devoted to this subject, there have been many Microsoft partners, including the brain trust here at Unify Square, who have zeroed in on this topic. 

Microsoft has been very clear that their UC future is Microsoft Teams. Given the huge Skype for Business install base, the customer interest and demand for this migration topic is not surprising. However, before simply stepping straight into a Teams upgrade framework, our latest take on how to upgrade to Microsoft Teams is a bit unconventional. This blog post details 4 ‘migration’ techniques that are a bit out of the ordinary. It also includes a quick recap of the true Microsoft migration best practices and highlights some of the top migration FAQs. 

Don’t Migrate…For Now 

When the current Skype for Business 2019 Server first appeared on the scene, our initial take on it was that it wasn’t really worth the price of the upgrade.  At the same time, we (like most other partners and UC market experts), pushed the narrative that Skype for Business is Dying.  Our advice was that current Skype customers be quick and nimble in looking to pivot into Microsoft Teams.  And yet, when you think about it, what’s the real rush?  Mainstream support for Skype for Business 2019 Server runs through January of 2024 and extended support pushes the envelope further until October of 2025.  In the high-tech world 4 to 5 years is a virtual lifetime.  So much can happen with the Microsoft UC platform story and other competitive alternatives in that time period. If you can wait, you should hang tight and see how the market evolves. 

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Examine Co-existence Alternatives 

There are all kinds of ways to cut this cake.  You can choose to co-exist between Skype for Business and Teams.  You can also choose to co-exist between Teams and Zoom.  In fact we authored a blog on this very topic quite recently.  If you consider your Office365 migration checklist, you may find that a move to only the collaboration (persistent chat) functionality in Teams is not only easy, but ‘enough for now.’  In parallel then, you may find that the Zoom Video Conferencing and even the Zoom Phone functionality is also easier to roll out vs a more complex Microsoft Teams UC migration. 

Skype to ‘Something Else’ Migration 

If you’re one of those ABM (Anything But Microsoft) mindset people, you may be asking yourself “Why am I looking at a migration to Microsoft Teams?”  There are certainly a very wide variety of different UCaaS platforms out on the market to choose from.  Before just settling into an ‘inevitability’ of a Microsoft Teams migration, you should do your due diligence.  Feature sets, platform stability, pricing, hardware integrations, contact center integrations, ease of support, security and compliance — all of these factors should be objectively examined.  Another great resource to look at is the Gartner Magic Quadrant for UCaaS systems. 

If you have stumbled across our website for the first time, and aren’t sure what we do, then allow us to introduce ourselves and to welcome you to Unify Square. Our software & services optimize and enhance the world’s largest Microsoft Teams, Zoom, Slack, Skype for Business deployments. We are on a mission to enable outstanding experiences for meetings, chats, and calls for enterprise customers. We hope you enjoy this blog post.

Skype Upgrade.

Microsoft has announced its End of Life plans for Skype for Business. Do you have your upgrade plans in place? Planning on Moving to Teams or Zoom? Let us help you take the proper steps to upgrade your current system.

Or Just Migrate to Zoom 

As a partner who focused on nothing but Microsoft for over ten years, it seems strange to say this.  However, Zoom is increasingly making a strong case for video conferencing and cloud phone systems in 2020 and beyond.  Like any migration decision, there are many intangibles to be examined. The overall Zoom story continues to grow stronger and stronger.  We recently examined this subject in a blog post, that you can read here. 

Old School’ Skype to Teams Migration Best Practices 

SfB to Microsoft Teams migration

Organizations determined to push through the migration from Skype for Business to Teams eventually had to end up here. We’ve covered this topic extensively over the past year.  We encourage you to download our comprehensive eBook about the topic.  We’ve authored a top 4 Skype to Teams deployment blunders blog post which also makes a great read.  In summary, when you work through our Unify Square advice (as well as that from Microsoft) it all boils down to the following 6 step method: 

PowerSuite Start provides Actionable Insights and Analytics for Zoom and Microsoft Teams. Summary Reports for FREE.

1. Planning & Strategy:

Carefully create a very strategic set of migration goals, use cases and user types.  Ensure that this strategy, while perhaps driven by IT, incorporates a broad set of stakeholders from across the company. It’s also important to make sure that this strategy is also well socialized and bought into.  

2. Pilot Mode Type and Modalities:

Your 2 biggest decisions as you jump into the migration are: 1) What sort of pilot mode are you going to start with — Islands, Skype Only or Teams Only.  The explanation for what and why of each of this could be the subject of its own blog post, so we won’t go into details here; and 2) What modalities are you migrating to – chat, conferencing and/or cloud phone? 

3. Policies & Governance: 

Especially because of the new and unusual collaboration security issues that Teams introduces, it’s very important to think through your governance model for teams.  Vague policies and limited governance can be the undoing of any initially well-planned migration strategy. 

4. Monitoring:

When you proactively monitor the quality and performance of conferences and calls, you’re better positioned to troubleshoot issues and isolate problems before they impact the user experience. Conversely, failing to measure and monitor and not having a plan in place to utilize a 3rd party tool, even during the pilot phase, can extend and complicate the overall migration process. 

5. Awareness & Training: 

IT departments who utilize what we refer to as the Field of Dreams migration strategy (“Build It and They Will Come”) are playing with fire.  A strong Teams migration plan always incorporates broad end user education and awareness. 

6. Operating @ Scale: 

This last point is the one (with the exception of a neglected Collaboration Security focus) most frequently overlooked.  The complexities of operating Microsoft Teams at scale can (especially for larger organizations) be much more involved than the pilot would suggest. For larger enterprise organizations, looking to involve a managed service once the Teams migration goes mainstream can often be an ROI-saving maneuver, even given the extra costs of the service.  

Top 3 Teams Migration FAQs 

There is no end to the frequently asked questions that we hear from customers about migrating to Teams. When pushed to arrive at our top 3 the result is the following: 

  1. What support does Microsoft offer customers who want to move to Teams? Especially those who have made significant investments in Skype for Business Online? Microsoft and its partners assist customers who want to move users to Teams with tools and guidance to control and manage the process. Prescriptive guidance is at Microsoft helps ease the transition for users new to Teams with a specialized first-run experience and in-product coach marks. FastTrack, instructor-led training, customer support, and partners are available to help guide customers through the transition. In addition, Microsoft hosts ‘Upgrade Workshops to help with upgrade planning. 
  2. Is there a firm deadline by which customers need to move from Skype for Business Online to Teams? Yes. Skype for Business Online will be retired on July 31, 2021.  Beyond which it will no longer be accessible or supported. We encourage Skype for Business Online customers to start using Teams and begin planning their upgrades now. This will allow you and your team ample time to complete upgrade prior to the retirement date.
  3. Why do I need upgrade guidance and assistance? Can’t I just delete/decommission Skype for Business? Upgrading from Skype for Business to Teams is more than just a technical migration. It represents a broad transformation in how users communicate and collaborate, and change is not always easy. The ideal upgrade approach should address the technical aspects and encourage user acceptance and adoption of Teams. This will guarantee a positive user experience and business outcome realization.

Microsoft Teams deployment Next Steps 

There are several options available to any organization as it approaches its next step away from Skype for Business.  In addition to our PowerSuite software and PowerSuite Cloud Managed Services, our set of Unify Square consulting services  coupled with our over ten years of Microsoft UC consulting experience can serve as a valuable asset to your Skype for Business to Microsoft Teams migration experience. 


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