InterviewUC&C26 Feb 2021 · 26 min read

Microsoft Teams Round Table: Migrating from Skype for Business

Skype for Business retirement is pushing Microsoft Teams migrations. Published on UC Today, experts from CallTower, DWS, Giacom, Soluno, Pexip and Qunifi explai

Anwesha Roy

Microsoft Teams round table Skype for Business migration

Microsoft kickstarted February by reminding all of us that there are now 6 months remaining until Skype for Business is retired, releasing a blog on this issue on the very first day of the month. Skype was a pioneer in the video-based collaboration space (almost as synonymous with it as Google is with search engines). So, the retiring of Skype for Business definitely marks a milestone is the eventual evolution and obsolescence of the traditional approach to video calls.

A little bit of nostalgia: Skype for Business officially came into existence in 2015, although it has been around for a while as Lync by Microsoft, and even longer as the original 2003 Skype platform later acquired by Microsoft in 2011. Skype had already started integrating with the Business service since 2013. The product enjoyed a good run for a few years, with several updates, releases, and a Mac client.

In 2017 (the same year Microsoft Teams was released), the company announced it would be gradually phasing out Skype for Business between then and July of 2021. As per the most recent announcements, Skype had over 40 million users last year, growing by 70% due to COVID-19-related WFH.

Sitting in February 2021, there’s now less than six months left in Skype for Business’ lifespan. While Microsoft continues to encourage Skype usage in the personal/consumer space, we’d imagine its days would be numbered once Teams Consumer edition goes live. What does this change of course look like for companies still on Skype for Business, and are there possible bumps on the road ahead? We sat down with Teams experts from CallTower, Digital Wholesale Solutions (DWS), Giacom, Soluno, Pexip, and Qunifi – pioneering Call2Teams™ to discuss Skype’s inevitable yet slightly disheartening fate, and what’s next for UC users.

CallTower is a global UCaaS and collaborations solutions provider, DWS is a communications reseller, Giacom is a cloud-service distributor, Soluno equips small businesses with office phone systems, Pexip is known for its video conferencing capabilities, and Qunifi’s UC platform – Call2Teams™ integrates with Office 365 and Teams.

Scroll down for expert viewpoints on transitioning from Skype for Business in 2021.

What are the major challenges from moving users from Skype for Business?

When asked about the challenges around transitioning users out of Skype for Business, our experts expressed divergent viewpoints. Some like William Rubio from CallTower said it is an infrastructure issue, while others like Steve Law from Giacom believe that the process could be rather straightforward. Overall, difficulties in transitioning users will depend on the size and complexity of your existing deployment, and, of course, the reseller/system integrator you choose to partner on this journey.

Here is what our experts had to say.

William Rubio, Chief Revenue Officer, CallTower

CallTower’s William Rubio admits that it will be quite a challenge moving users out of Skype for Business, a solution that has been around in some way or the other for over a decade. What’s more, SfB often has intricate dependencies with other communication channels in the enterprise. Retrenching the entire ecosystem would take some doing, feels Rubio.

“This could be a tough time for Skype for Business Online users to make an infrastructure change. Many have already moved on to Teams. Some challenges around committing to the move from Skype for Business to Teams is that there may be complex designs that require additional assistance from a Teams Direct Routing partner or an Enterprise Skype for Business provider (in a private cloud environment),” Rubio said.

Our other experts echoed this sentiment, emphasising the need for an experienced partner’s intervention.

Alex Mawson, Product Director, Digital Wholesale Solutions

Alex Mawson from Digital Wholesale Solutions spoke about the specific challenges ahead of companies as they move users out of SfB. In many ways, users could be wary of another learning curve, which can only be assuaged by convincing them of the benefits of the move.

“The challenges when migrating from Skype for Business to Teams will depend on the size of the existing deployment and the level of integration and features that are being used. It is important customers gain a sound understanding of the significant benefits MS Teams brings, quite simply, MS Team is “Skype for Business on steroids” and implemented correctly will become your business collaboration hub,” he noted.

Mawson explained which milestones require attention during user transitioning – “These items include:

The rollout of the applications and widgets (desktop and handheld devices)
Migration of telephony features and PSTN breakout
Ensuring the security controls including federation policies are in place
Teams unification with SharePoint, possibly stretching out the migration

But the benefits are also immense, and will only compound with time. Speaking of the benefits of the move, Mawson mentioned an important caveat – telephony configurations that must be recreated as a “lift-and-shift” migration simply isn’t possible.

“Teams significantly enhances a user’s collaboration and telephony experience but for those using Skype for Business with telephony there are several configuration items which are not migrated and must be recreated when users move to TeamsOnly Mode,” said Mawson.

Steve Law, CTO, Giacom

Giacom’s Steve Law, on the other hand, is quite optimistic about the move away from SfB, mentioning the enablement tools that Microsoft has made available for this journey.

There is no denying that Teams offers a stronger value proposition than Skype for Business. The challenges are around changing user mindset and recreating the technology ecosystem, rather than missing out on any features or capabilities. “Moving from S4B to MS Teams can be straightforward with the right IT partner who has the necessary experience and has done it before,” Law said.

Due to this, Law recommends partnering with an experienced IT service provider and paying close attention to Microsoft’s first-party guidance materials. “MS has produced a significant quantity of materials to try and make the journey as clear as possible, but you can’t beat the experience gained from having done it multiple times before,” he added.

He also mentioned the need for a holistic approach, comprising preparation and post-transition change management – not just the act of moving users out. “I would really recommend following the MS framework which outlines the process very clearly and includes all the things you need to consider before, during and after the migration to get the most out of Teams and to make the experience as painless as possible for all concerned,” notes Law.

Mattias Holmberg, Product Manager, Cloud PBX, Soluno

Mattias Holmberg from Soluno elaborated on the potential challenges when an organisation uproots its user base from one platform in favour of an alternative. This is particularly true for companies with on-premise deployments, as then it would entail the adoption of a whole-new hosting environment and not just a new platform.

“If using Skype for Business on Premise, there are technical parts of the user migration process that some companies will probably feel uncomfortable administering themselves. This will add a level of complexity as timelines will need to be synced with consultants,” Holmberg opined.

On the user side of things, enabling adoption for a large user base concurrently and that too without IT handholding the process in-person will be difficult. Meanwhile, it isn’t like organisations can afford any downtime while users become familiar with the new tools on Teams, as virtual collaboration via SfB and now Teams is mission-critical to your operations in a WFH world.

“I believe the onboarding processes of getting a lot of users to move to a new tool at the same will always pose a challenge. As chat and video-communication has become a central part of the current work-from-home-situation, it is even more crucial that each employee is ready to handle teams from the get-go as the IT department will not be able to over-the-should-help everyone,” he agreed.

Andrew Reitter, Senior Director of Business Development at Pexip

Pexip’s Andrew Reitter highlighted another bone of contention: SfB-Teams interoperability.

User migration from Skype for Business to Microsoft Teams will not happen overnight. The two platforms will have to sit (and operate) side-by-side at least for the first few weeks of the change. This period will be rife with fragmentation risks, and interoperability between Skype and Teams is the only answer.

“One of the biggest challenges we see is meeting interoperability between Skype for Business and Microsoft Teams. During the migration phase, both applications will need to coexist for a period of time. Some users will have Skype for Business as their primary collaboration tool and some will have Microsoft Teams, but everyone will need a way to join meetings together using their own solution to minimise disruptions to the business,” Reitter noted.

Reitter further mentioned that users have gotten used to a certain device usage pattern with Skype for Business. The same flexibility must be there in Teams for companies to achieve the same adoption rates, fast. “Another challenge is Microsoft Teams interoperability with existing video conferencing systems. Users need the ability to join Teams meetings from anywhere – whether from their personal device at home, or from room systems in the office,” he said.

And like Holmberg from Soluno, Reitter spoke about another spate of challenges involved in on-premise to cloud migration. “Lastly, moving to the cloud. Skype for Business is on-premises, and for some, moving to the cloud can pose challenges. The customer may trust Microsoft in their move to cloud Exchange/Teams, but lack trust in the Cloud Video Interop (CVI) provider’s cloud,” he added.

While Microsoft’s value proposition with Teams is globally recognised, trusting third-party-enabled interoperability between the company’s meeting rooms and video devices with Teams on the cloud is another matter altogether.

Richard Carver, CTO, Qunifi

Richard Carver from Qunifi discussed the pros and cons of the move. On the one hand, Teams offers a wealth of features to collaboration users, miles ahead of SfB capabilities. But on the other hand, there cannot be a disruption in services. As Carver put it, “The move from Skype for Business (S4B) to Teams is generally welcomed by users, with the new working environment offering a much richer experience. For enterprises, their workers, and their customers, delivering continuity of service in these challenging times is key.”

With online/virtual communication now being the only way companies can conduct work, disruption in communication services means downtime for the entire business. Like Holmberg, Carver reiterated that careful planning is required so as to make the switch as seamless as possible.

“S4B is primarily a communications platform, so the migration challenges are all about transitioning communications systems. In a business-critical environment where mobility and home working are more important than ever, such a change needs to be planned carefully,” he said.

Finally, to take care of dependencies, partner intervention is essential.

“The ability for Enterprises to retain their existing communication infrastructure and PBX platforms, which may be powering S4B, also presents a challenge and requires solutions like Call2Teamss™ – a UCaaS solution that sits between any phone system, PBX or SIP trunk provider, and Microsoft Teams,” explained Carver.

In other words, companies must plan ahead if they are to avoid sunk costs in their existing systems and ensure continued usability on Teams.

Next, we asked our experts about their thoughts on the potential risks that businesses could be incurring as SfB is permanently discontinued.

Are businesses ready for the discontinuation of S4B later this year, are there risks for businesses?

As with any change, there is always a risk of process disruption and lost opportunities in the meantime. Regarding organisational readiness for SfB discontinuation, our experts said that it depends entirely on if they have a project implementation plan and the team already in place, with less than six months to go. Without this, there is a risk of communication outage, which could lead to a breakdown in an organisation’s ability to build products (internally) and transact with customers (externally).

Let’s explore our expert insights in full detail.

William Rubio from CallTower is of the opinion that organisational readiness will vary from one company to another. Prerequisites for this readiness, he said, is an implementation design and an implementation management team.

“It really does depend on the designs the company has in place around their Skype for Business. Whether a company wants to move their SfB Online to a private cloud environment or move to Microsoft Teams, CallTower empowers them with solution architects to aid with designs + a project implementation management team to make the transition seamless"

Alex Mawson from Digital Wholesale Solutions noted that several organisations have already started their migration journey. This isn’t surprising given that we have known about SfB’s scheduled demise for over three years now. For some, communication is divided between Skype and Teams while others are using each platform for a particular use case.

“Customers are at various stages of migration. More frequently we are seeing businesses running in a mixed mode (coexistence) of Skype for Business and MS Teams. Some are operating Teams for internal collaboration and Skype for external until users are moved to TeamsOnly mode,” notes Mawson.

These companies could have the upper hand during the upcoming migration. But those who are still stuck on pureplay SfB deployments, there’s a massive risk to business continuity.

As Mawson said, “The risks are simple for those who had not already planned their migration, Skype and Teams have become central to a business and without a sound migration plan their ability to trade and communicate internally and externally will be severely restricted.”

One important area that needs attention is telephony. Teams offer a wide range of telephony capabilities, a lot of which requires the intervention of an experienced partner to fully unlock.

“Selecting the correct solution for those using telephony features is critical. Whereas MS Teams offers this functionality via Enterprise Voice services, we are seeing partners taking advantage of our enhanced Direct Routing products which offer enriched call handling services and bespoke call packages whilst allowing hybrid MS Teams and UC deployments”

Companies investing in partner services can see outsized returns from the migration, far outweighing the risks of transitioning from Skype.

Giacom’s Steve Law turned the spotlight on the unique requirements that lie ahead for companies with on-premise Skype for Business deployments. The 31st July deadline doesn’t apply to them, technically, but most on-premise SfB instances tend to rely on cloud services on a hybrid basis, at least to a degree.

“The deadline for migration is the 31st July 2021, which is when Skype for Business Online is retired. If customers are using on-premise Skype for Business then they are not affected by this date but if they are using a hybrid configuration then they are and need to migrate”

Putting off migration planning until the 11th hour will compound the risks involved. “As is common with product end of life dates many customers ignore them until it is too late to plan properly for the migration and end up rushing the process and having a poor experience. My strong recommendation to all Skype for Business customers, both on-premise and online would be to find a good IT partner who is experienced in S4B migrations and start to plan for it now.”

Simply put, it is a good idea to start preparing your roadmap from Skype to Teams at the earliest, regardless of your hosting environment. And as Law mentions, there is not just a stick but also a carrot – “MS Teams is a significantly better product than S4B and will provide them with numerous benefits which they are missing each day they delay.”

When we asked Soluno’s Mattias Holmberg if businesses were ready for the discontinuation of SfB, he agreed with Mawson that most probably are, and some might have even embarked on their migration pathway. “The writing has been on the wall for quite some time now and the buzz around Teams generated by the challenging year behind us has lured a lot of companies and users towards Teams ahead of any imposed deadlines,” he mentioned.

“There will always be some businesses that have been distracted and will be unprepared but the bulk of migrations will most likely be done in time.” The lion’s share of risk will fall on this handful of businesses who waited for the very last months.

The more pertinent issue is whether companies are ready to start utilising Teams’ full potential, rather than if they are ready to leave Skype for Business behind. Teams presents an entirely new user experience and feature architecture, even if it shares some of its core capabilities with SfB.

“Are businesses ready to start working effectively in Teams is perhaps a more pressing question?” Holmberg notes.

“Teams is a different beast completely and it is no problem for an uninvested company to get lost in new possibilities and structures”

Pexip’s Andrew Reitter said that in his experience, most companies have already begun to migrate, in many ways propelled by Teams’ robust set of features. “Microsoft Teams is an extremely powerful collaboration tool, and many of the customers we work with have already started their migration from Skype for Business or are planning to soon,” according to Reitter.

But the risk for those who haven’t is that virtual communications could come to a standstill:

“There are risks to organisations that have not started their planning process yet, though, as failure to plan could result in users not being able to join meetings in the future"

And there are always risks arising due to a transition from on-premise to the cloud. “Migrating to Teams also involves moving to a cloud model, which can bring additional considerations,” he said.

As Reitter previously mentioned, trust in a third-party CVI provider could be a consideration for companies. He shared two parameters to remember when enabling interoperability between SfB and Teams during the early days of the migration:

SfB and Teams certification - “By choosing a CVI (Cloud Video Interop) vendor that is certified for both Skype for Business and Microsoft Teams, organisations can ensure that everyone can simply meet using their familiar workflows.”
Flexible deployment - “In addition, they should look for a CVI vendor with flexible deployment options to support their changing needs over time as they migrate to a cloud environment.”

Richard Carver from Qunifi commended Microsoft for giving organisations quite a long period of notice before Skype for Business is finally discontinued. And the pandemic has only pushed preparedness further, making it necessary to adopt cloud-based communication even among organisations that previously operated on-premise.

“Microsoft has done a good job of making Skype for Business Online users aware,” said Carver.

“We have seen a steady stream of Skype Online customers moving over to Teams in the last 12 months, although many have left it to the last minute. Due to the pandemic, the landscape has changed. Many Enterprises have had to roll out Teams in an accelerated manner”

The journey will be much simpler and less risky for organisations with coexisting SfB and Teams deployment.

“At Call2Teams™ we have experienced dramatic growth in Teams deployments where customers have retained their existing voice infrastructure. With customers running S4B and Teams side-by-side, the migration to Teams-only needs to be done with the service in-flight. Microsoft have made this easy, yet it still needs planning to avoid downtime,” Carver noted, adding that a service like Call2Teams™ to manage the complexity of migrating communication connections removes a huge burden from the IT team.

“With Microsoft Teams, all users are under one collaborative platform, meaning fewer systems to manage and maintain.” Ultimately, the efforts will be worth it as organisations achieve a consolidated communication and collaboration ecosystem with significantly lower IT overheads.

Next up in the discussion, we asked our experts about the nature of the migration journey. What are the possible concerns, and how can one prepare?

What does the migration journey look like from S4B to Teams – what should businesses be aware of?

The transition from SfB to Teams is indicative of a far larger shift – the rise of UCaaS and the inevitability of cloud-based communication systems. Our experts shared with us several useful tips to help the migration along, from detailed implementation guides by CallTower, to device recommendations and user training/onboarding. Telephony could prove to be one of the toughest pieces of the puzzle, while cloud first-timers must consider the benefits of modernisation as part of the process.

Here are the experts’ insights.

[caption id="attachment_33212" align="alignleft" width="200"] William Rubio[/caption]

When we asked CallTower’s William Rubio about the migration journey and its potential roadblocks, he pointed us towards several helpful resources, meant to guide Teams implementations. As per CallTower’s approach, the journey will take place in five stages – initiation, planning, execution, adoption, and acceptance. A partner should ideally handhold the process to ensure that expectations from the change are clearly documented and met.

You can read CallTower’s implementation guide, specific to telephony here.

In one blog, Kade Herbert from the company writes, “CallTower sees Teams as an option for a percentage of the workforce, but not a one-size-fits-all solution for all users.” This pretty much sums up the pragmatic nature of the journey, which should necessarily factor in your organisation’s custom needs.

Alex Mawson from Digital Wholesale Solutions appreciated the fact that Microsoft has made transitioning as easy as possible for its customers. Not only is there a long notice period, but there is also plenty of advisory content from Microsoft.

“Microsoft offers an extensive level of supporting content online for customers to prepare and migrate to MS Teams,” Mawson said.

[caption id="attachment_36090" align="alignright" width="200"] Alex Mawson[/caption]

He shared with us fur recommendations to alleviate concerns during migration:

“Customers should research online and where needed partner with a Microsoft Teams provider to design a migration path and deployment to best meet their business needs”
“MS Teams will quickly become an ecosystem within a business; companies should look at a natural evolution as users adopt a feature-rich way of remote working”
“The migration to Teams may also drive a requirement to replace Skype only compatible devices such as SBC’s and handsets plus a demand for improved hardware and accessories such as faster PCs and HD cameras”
“Businesses looking to add direct routing/enterprise voice should take care to ensure all requirements can be met, a hybrid UC solution may be a better solution”

Apart from these technical aspects, Mawson is careful to note that Teams is better suited for the needs of the modern WFH user than SfB ever was. Companies should take advantage of Teams’ non-work features that also play a big role in productivity.

“A key item of advice for Teams adoption is to ensure focus is put into how the solution can separate work and social interaction whilst ensuring a level of wellbeing for employees,” he added.

[caption id="attachment_36091" align="alignleft" width="250"] Steve Law[/caption]

Giacom’s Steve Law suggests adhering to Microsoft’s first-party migration guidance – “You should follow MS framework for migration from S4B to MS Teams which outlines all the steps from initial planning, technical readiness, through implementation to support.”

He also spoke about two possible ways in which your migration journey could play out. “One thing to decide is whether you are going to take an overlapping capability or select capability approach:”

Overlapping capability - “I would recommend the overlapping capability approach which is where chat, meetings and VoIP calling are available in both S4B and MS Teams, this will accelerate the move to Teams because as soon as users access any of these features, they will quickly realise it is much easier to use and has a wider set of functions and won’t go back.”
Select capability - “An alternative to this is the select capability approach which is designed for a longer coexistence period, where collaboration is in Teams and chat and VOIP are in S4B, this is sometimes required for more complex S4B deployments which have on-premise enterprise voice.”

In other words, companies must decide whether they want to retain SfB and Teams side by side for a while or plan on retiring Skype completely very soon. Needless to say, the former is more advisable given that Skype’s days are clearly numbered and the select capability approach would introduce more complexities than it helps to avoid.

[caption id="attachment_35257" align="alignright" width="200"] Mattias Holmberg[/caption]

Like Law, Soluno’s Mattias Holmberg also advises against the co-existence or select capability approach.

“The first thing to consider is whether to go for a hybrid transitional period with both apps coexisting within the company or to move all users in a cohesive migration. Where possible, it is probably the best approach to move all at once as it keeps everyone on the same track and makes communicating timelines and best practises a lot easier,” Holmberg believes.

A complete migration would prevent fragmentation in the user experience, ensuring that the same capabilities were rolled out to every member of your workforce at the same time.

And to augment this migration model, companies need to invest in user education and onboarding. “The most important step is education and onboarding. Teams is a lot different than Skype for Business and a lacklustre introduction to a tool with such a prominent role in the current state of work could sour the process of adoption for a lot of businesses.”

Without adequate training, users would struggle to apply Teams in their daily workflows, at a time when virtual communication and collaboration is the backbone of work. It would also hold you back from realising a lot of the benefits Microsoft intends to deliver by discontinuing SfB in favour of Teams.

[caption id="attachment_36092" align="alignleft" width="200"] Andrew Reitter[/caption]

Pexip’s Andrew Reitter zeroed in on the user experience and how it’d be influenced by the migration journey. For instance, COVID-19 might have spurred a sudden shift to cloud-based Teams, but requirements for plugging in physical conferencing hardware would remain in the long term.

“While there are a lot of considerations for a successful Teams migration, it’s important to remember how user workflows will be impacted,” he mentioned.

An important part of the migration process, therefore, should be taking stock of what Teams doesn’t do and pre-empt the gap so that user experiences aren’t disrupted. For example, as Reitter says,

“Microsoft Teams brings everyone together in a single meeting, but it does not support third-party calling.”

“Organisations should consider how the migration will affect users’ workflows and interoperability needs and make sure there is a plan to mitigate any unforeseen consequences. We see many organisations that moved to Teams rapidly due to COVID-19, what they don’t realise is that when users return to the office, they will use the conference room video conferencing device and try to connect to their Teams meetings. Now is a great time to implement a CVI solution to prevent this impending disruption in user experience,” he added.

The final consideration is whether you’d want to get two birds with one stone. Given that the discontinuation of Skype mandates an upgrade to cloud-based systems, it might be advisable to take this opportunity and invest in a hardware upgrade as well.

“Microsoft Teams is cloud-based,” said Reitter, “Whereas Skype for Business is on-premises. In moving to a cloud environment, many customers take the opportunity to modernise their video conferencing infrastructure at the same time. This helps them simplify IT while continuing to maximise ROI in their existing room-based video conferencing systems.”

A holistic migration like this will offset any risks to unlock outsized returns.

[caption id="attachment_36093" align="alignright" width="198"] Richard Carver[/caption]

Richard Carver from Qunifi elaborated on the migration journey as it pertains specifically to telephony.

“Many customers have retained S4B (either in the cloud or on-premise) because they have phone services connected to it. This is typically the most difficult piece to move,” explains Carver.

There are three options: port your existing numbers to Microsoft, use direct routing, or use a third-party integration engine that can connect your Skype SIP/PBX systems with Teams. The last option could be the most beneficial as it promises end-to-end migration in a matter of days.

“Customers don’t want to port their numbers over to Microsoft, because in doing so, they may not retain complex, high-functioning set-ups. The other option is to use Direct Routing, but that brings a whole load of complexity if a customer is looking to implement this from scratch. Third, we have Call2Teams™, which will effectively link existing S4B SIP trunks or PBXs into Teams without needing any deployment of software or hardware, providing a seamless transition from S4B to Teams. “

Many of Qunifi’s customers have migrated their entire organisation over a weekend!

And like Reitter, Qunifi’s Richard Carver spoke about the potential of turning SfB-Teams migration into a transformative modernisation project for your communication capabilities. This, he says, would significantly reduce IT burden while simultaneously elevating user experiences.

“Customers are using the migration as an opportunity to consolidate their approach to communications, bringing phone calling into Teams, instead of deploying a separate softphone to users or third-party S4B integrations. This reduces the IT burden and gives end users a more productive working environment,” said Carver.

As we inch closer towards Skype’s retirement, companies must revisit their SfB dependencies and fragmentation within the Microsoft ecosystem. While the July 31st deadline may not blanket-apply to all deployments, it is advisable to start exploring migration options without leaving it to chance, even if you have on-premise systems. Resellers, particularly those specialising in telephony, will play an important role over the next few months, helping organisations align with the new features, the new ecosystem approach, and the new licensing needs that Teams calls for.

The recommendations by experts from CallTower, Digital Wholesale Solutions (DWS), Giacom, Soluno, Pexip, and Qunifi will be instrumental in making your transition user-centric and risk-free.

We hope you enjoyed this edition of the UC Today Roundtable.

We’d like to thank William Rubio, Alex Mawson, Steve Law, Mattias Holmberg, Andrew Reitter, and Richard Carver for joining us and sharing their invaluable insights. For more such exclusive discussions with experts and specialists, please follow our YouTube channel, where we regularly share videos speaking with some of the leading industry names today.

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