How to Ensure the Best Skype for Business to Microsoft Teams Migration

Written by: Chloe Kearin Willeford

Updated: 07/10/2021

Soon, another shift will come in the already quickly changing work communication and collaboration landscape. Microsoft’s widely used unified communications (UCaaS) platform, Skype for Business Online, will be retired on July 31, 2021. Meanwhile, Skype for Business Server, their UC on-premises version of the software, will receive mainstream support only through January 9, 2024 and extended support through October 14, 2025. As a result, Microsoft is encouraging all current Skype for Business users to migrate to its successor platform: Microsoft Teams. But a Skype for Business to Microsoft Teams migration can seem daunting. 

So, why is it worth considering Microsoft Teams as an alternative to Skype for Business? Microsoft Teams is catching on in large enterprise environments. The platform already boasts 145 million users across 500,000 organizations, and Teams’ functionality across video calling, file sharing, and chat means that these numbers are only going to increase with time. Plus, Teams’ chat and file sharing functions means that migrating to Teams helps to reduce users’ email volume. A study commissioned by Microsoft in April 2019 showed that using Teams reduced the number of emails by 17.3%.  

It is crucial that company leaders thoroughly think through a Skype for Business to Microsoft Teams migration. Upgrading from Skype for Business to Teams is more than just a technical move. It represents a broad transformation in how users communicate and collaborate.  In a hybrid work environment, company leadership needs to ensure that all users enjoy excellent unified communications and collaboration experiences. A migration between platforms signifies a radical change in how employees can imagine themselves in the company’s community. This means choosing the right communications platform for your organization.  

In this blog, we’ll explore pre-migration considerations, the benefits and challenges of moving from Skype for Business to Microsoft Teams, and best practices for Skype to Teams migration. Finally, we’ll cover how third-party software, managed services, and consulting services like those from Unify Square can ensure your migration’s success.  

Microsoft Teams Policies Best Practices How to Implement Flexible Governance with Adaptive Scopes

Pre-Migration Considerations 

There is a lot to think about before a huge migration like that from Skype for Business to Microsoft Teams. 

  • Time: While organizations that use Skype for Business Online will have to think quick before the service’s end of support date in July 2021, anyone that uses the Server (on-premises) version of the platform will have a little longer to consider their next move before its 2024-2025 end of support date. Server users don’t have to rush to migrate away from Skype for Business. Instead, they should start slowly preparing to ensure a smooth transition for end users.  
  • Coexistence Options: You also don’t have to completely move away from Skype for Business to Microsoft Teams just yet. You might consider using Skype for Business’ video conferencing feature but Teams’ chat function, for example. Zoom is also a great coexistence option; their video conferencing and Zoom Phone can integrate well with the messaging and file-sharing abilities of Teams.  
  • Alternative Platforms: If you are looking for a complete migration away from Skype for Business, Microsoft Teams is not the only option. Zoom is becoming an increasingly strong alternative to Skype for Business and Teams in the unified communications market — it offers group chat, conference calling, and Zoom Phone calls and constantly adds new collaboration features. However, Zoom is not as seamlessly integrated with email or file sharing as Teams. Slack, with its great chat and file-sharing features, is also a contender to replace Skype for Business. However, Slack does not have built-in video or audio call functionality. An organization that adopts Slack for communication purposes would also have to use a conferencing service like Zoom or Teams. 

Overall, Microsoft Teams stands out in the unified communication market for its chat and file-sharing capabilities, excellent integration with Outlook email, and ability to facilitate video and audio calls.  

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Benefits of Migrating from Skype for Business to Microsoft Teams 

It’s important to understand how the potential platform might be better than what you currently use. Skype for Business certainly provides some challenges. So, in this section, we outline the ways that Microsoft Teams compares favorably to Skype for Business.  


Cloud Functionality 

One way in which Microsoft Teams stands out from Skype for Business is in its cloud functionality. Microsoft Teams is, as Microsoft likes to say, born in the cloud. Unlike Skype for Business, Microsoft Teams offers a rapid cadence of service and feature enhancements. This faster pace of changes means a more efficient response to customer feature requests. It also means that it is more difficult for organizations to keep up with end-user training. 

Microsoft Teams also supports three types of cloud phone functionality. Direct Routing integrates a carrier phone plan into cloud phone services. Microsoft Calling Plans are fully managed and supported by Microsoft 365. Operator Connect provides a mix of the two through routing an existing carrier phone plan through the Teams admin center. This range of functionality provided to cloud phone services means that companies can either integrate an existing phone plan into the cloud or purchase a new phone plan from Microsoft; this further eases the transition from Skype for Business to Teams. 

Microsoft evolved Teams to support improved unified communications meeting performance using a Regionally Hosted Meetings service integrated with Azure. This capability allows users to host online meetings from their “local” geo as opposed to the organization’s home-tenant geo. The ability to leverage the large footprint and greater density of Azure data centers enables users to host online meetings that are closer in proximity to their work locations. 


End-User Experience 

As well as improved cloud functionality, Microsoft Teams also offers a better end-useexperience compared to Skype for Business.  

  • Teams Chat: In contrast to the Skype for Business instant message feature, where messages disappear over time, Teams’ chat feature offers permanent messages. That means employees can refer to colleagues’ ideas in future, further encouraging a reduction in email volume.  
  • Mobile App: Teams offers an excellent mobile app, making it easier for remote workers and people on the go to connect with their in-office teammates.  
  • One Software for All: Because of Teams’ ease of communication, the platform increases productivity, collaboration, and teamwork between workers, especially in a remote or hybrid work environment. Teams incorporates all or most work apps a person might use — notes, files, chat, and third-party apps — into one software. This creates more of a virtual office space than a system in which users are switching between different platforms might.  
  • Connection between Workers: Further, Teams effectively connects remote workers to in-office workers. Many of the apps that remote workers use to communicate, like email and chat, are also available to in-office workers. So, the experience difference between in-office and remote workers is not quite as different as it might be without Teams.   
  • Reliability: Because of its integration with Office 365, its legacy of Lync and Skype for Business learning and experience in the UC space, and its creation by a well-established company, Microsoft Teams is extremely reliable.  

Challenges in Migrating from Skype for Business to Microsoft Teams 

While Microsoft Teams has many benefits compared to Skype for Business, it isn’t perfect.  

  • Teams Adoption Process: Teams’ ‘swiss army knife’ Office Hub orientation allows for a huge range of functionality but can also lead to confusion, especially for end-users accustomed to the simple user interface of Skype for Business. Multi-tasking across different apps within Teams, like Outlook, Word, and SharePoint, involves having several tabs open in a browser at once and can be overwhelming. This lack of a simple client will require significant change management from IT for end users. A simple client was the hallmark of Skype for Business since its early OCS and Lync days. IT teams will also need to pay attention to the adoption process: adoption of Teams tends to be decentralized, potentially slowing down the migration as a whole.  
  • Team Sprawl: Another Teams function that could be confusing for Skype users is the ability for end users to create teams themselves. This ability can create team sprawl, a proliferation of teams created by many similar users and covering many similar topics, creating redundancy and choice overload. IT and business divisions need to find a way to manage sprawl within Teams (e.g., through provisioning guidelines or tools). Otherwise, the sheer number of teams become unworkable and overwhelming for end-users.  
  • Collaboration Security and Governance Risks: Migrating to Microsoft Teams can cause other huge risks to company information security as well. There are two primary security concerns involved in the switch to a different unified communication and collaboration platform: how are end users communicating sensitive information (are they using cell phones or personal email accounts), and how is the platform itself tracking or using sensitive company data? Without strict security and governance policies, end-users might do what is easiest for them without regard for security risks.  

Our expert consultants can work with you on platform selection and create deployment plans to ensure a successful roll-out.

Best Practices for Skype for Business to Microsoft Teams Migrations 

If your organization is ready to migrate from Skype for Business to Microsoft Teams, there are multiple factors to take into consideration before taking the plunge. How you plan, publicize, and secure your migration are key elements in the migration’s ultimate success.  

  • Planning: The most important step for a successful migration to Microsoft Teams from Skype for Business is making a detailed plan. This plan should include end goals, use cases, user types, and use modalities of Teams. Now, run a pilot test of the new software in one specific group to iron out kinks before introducing it to the whole company.  
  • Publicization: A wider introduction of a new platform to an entire company is also difficult for IT teams. Without wide publicization of the availability of new software, employees are not going to make the change. One effective strategy for the introduction of a new platform is the use of “champions.” A champion is a department leader, subject matter expert, or manager who is already successfully and happily using the new software. They can encourage the use of the new software and answer questions that colleagues may have during the migration.  
  • Security and Governance Conventions: As mentioned above, security and governance issues are always a concern during platform migrations. While Microsoft Teams is a secure platform, the lack of a concrete governance policy can lead to data security risks. It is important for IT teams to have strict governance rules for the review of number and existence of teams (to mitigate team sprawl), for naming conventions (to make it clear who is in that team and whether it’s internal- or external-facing), for the review of who is in which teams (to prevent guests overstaying their welcome). And, IT teams should continue to carefully monitor how information is communicated between employees and tracked by the platform itself.  

Evidently, there are areas of concern and potential confusion when migrating from Skype for Business to Microsoft Teams. How is your organization going to handle the migration process? How will the migration operate at scale? One migration strategy might work great for a company of ten people. On the other hand, migrations at enterprises require significantly more thought and planning. Often, Microsoft Teams’ native governance tools aren’t enough for a company to ensure its information security. And, using third-party unified communication management software can often save companies money in areas like monitoring and administration.  

Microsoft Teams Policies Best Practices Naming Conventions in PowerSuite

How PowerSuite Can Help 

PowerSuite is Unify Square’s integrated unified communications governance software. PowerSuite can help your organization successfully and efficiently migrate to Microsoft Teams from Skype for Business; key features enable benchmarking, usage and adoption, help desk, tracking, problems and insights, and policy management,. 

  • Single Pane of Glass View: When it comes to supporting a migration, PowerSuite offers a single pane of glass view to manage both Skype for Business and Microsoft Teams in the migration transition state, which can last multiple years for enterprise customers. The Insights Center, Operations Dashboard, and Help Desk, PowerSuite allow IT teams to quickly discover and troubleshoot migration issues. Other migration administration tools, like Phone Number Management and User Management, make it easy to transition users to Teams Phone.  
  • Security Overview: PowerSuite empowers IT teams to easily navigate new issues. Our Security Analytics tool helps IT teams to discover collaboration security issues, which were previously not a concern with Skype for Business. This dashboard is a fantastic place to get started with Teams governance with full blind spot visualization.  
  • Measuring Success: PowerSuite tools also enable IT teams to measure overall migration success. Its Usage and Adoption function lets IT teams compare usage between platforms to measure the adoption of Microsoft Teams. Additionally, the Executive Dashboard compares quality between the platforms to identify areas that require further optimization.  


Unify Square Consulting Services and PowerSuite Managed Services 

Still unsure about your Skype for Business to Microsoft Teams migration? Unify Square can help. As a Microsoft gold partner, and because our portfolio of expertise in all things UC and Collaboration extends beyond software into consulting and managed services, we are able to support many different transformation and runtime scenario issues and questions. 

If you want to guarantee the success of your migration, engage our Cloud Managed Services to have us drive all IT operations relating to Teams on a 24×7×365 basis. Or, check out our set of Unify Square Consulting services, powered by our over ten years of Microsoft UC consulting experience, to utilize us as a valuable asset to your planning, architecting and migration work for Skype for Business, Microsoft Teams and Zoom. You can read more about all the details of our complete Skype for Business support here and our Teams support here. 

Our PowerSuite Software, Consulting Services, and Cloud Managed Services are a power trio; take control over your unified communications experience and make your Skype for Business to Microsoft Teams migration a resounding success. We hope this article has set you on the right path to migration.  

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