If you’re a business owner, IT decision-maker, or C-suite exec, this isn’t just a software update. It’s a chance to modernise how your organisation communicates, collaborates, and connects with customers. But it’s also a moment where a rushed or poorly planned move can cause unnecessary disruption.
In this guide, we’ll walk you through how to plan, execute, and optimise your migration to Microsoft Teams so you maintain business continuity, boost collaboration, and set yourself up for the AI-powered workplace of tomorrow.
Why is Skype for Business being phased out?
In July 2019, Microsoft announced the retirement of Skype for Business Online, with services ending on 31 July 2021. While on-premises Skype for Business Server versions are on extended support until October 2025, the direction is clear: the future is Microsoft Teams.
The decision aligns with Microsoft’s strategy to unify chat, meetings, calling, and app integrations into one platform, enabling smarter workflows, integrated security, and continuous innovation.
Put simply: Microsoft isn’t just replacing Skype. They’re moving the market towards a platform that’s built for hybrid work, cloud collaboration, and AI-led productivity.
Key considerations before migration
Like any technical project, you can’t just plug and play. You’ll need to carefully plan and consider several factors before you get started. It’s critical that before you touch a single user account, you address these areas:
Technical readiness
Before migrating to Microsoft Teams, you need to ensure your infrastructure can handle the demands of the platform. A smooth experience relies on more than just installing the app – it needs robust network performance, compatible devices, and integrated systems that talk to one another seamlessly.
Assess network bandwidth, latency, and QoS for voice and video
Check devices and meeting rooms are Teams-certified
Map any third-party voice integrations or contact centres
User adoption and training
Technology only delivers value if people actually use it. Transitioning from Skype for Business to Teams means helping users understand what’s changing, why it’s changing, and how they can get the most from the new tools. It’s important to emphasise what the benefits are for them, and not just the business advantages.
Build a comms and training plan to avoid resistance
Use champions networks, self-help resources, and live training sessions
Security and compliance
While Microsoft Teams introduces new capabilities for your business, it also changes the way data is stored, shared, and managed. You’ll need to ensure these shifts align with your organisation’s security standards and regulatory obligations.
Align Teams policies with ISO27001, GDPR, and your compliance frameworks
Review and update data retention and lifecycle policies
Feature comparison
Not every Skype for Business feature has a one-to-one match in Teams, so understanding what to replace or reimagine before migrating is key. This is particularly important for specialised workflows and hardware.
Identify Skype features that need a Teams equivalent
Plan for analogue devices, response groups, or niche call workflows
In one legal sector migration, we identified an old fax-to-email gateway no one had documented. Catching it early meant we avoided a last-minute scramble.
Step-by-step guide to migrating from Skype for Business to Microsoft Teams
When you migrate from Skype for Business to Teams, it’s not just a technical change, it’s a shift in how your organisation communicates and collaborates. By following a structured approach, you can reduce disruption, build user confidence, and maximise the benefits of Teams from day one.
Preparing for the transition
A successful migration, for any project, starts with knowing exactly where you are today and who will be affected. The means taking stock of your current environment, engaging the right stakeholders, and setting clear project goals. Without these foundations, even the best technical execution can fall short.
Audit Skype usage: call volumes, devices, user profiles
Engage all stakeholders - IT, HR, operations, frontline teams
Define what success looks like - speed, adoption, cost savings, or feature gains
Choosing a migration path
Every business is different, and the way and pace of one organisation will differ from the next. Microsoft offers several coexistence and migration modes, and choosing the right one depends on your timelines, user readiness, and technical requirements. The goal here is to balance speed with stability, while minimising confusion for your end users.
Microsoft supports three modes:
Islands mode (coexistence - short-term only)
Skype with Teams collaboration
Teams Only (recommended)
Think of Teams Only as moving fully into your new office, not just setting up a desk in the lobby.
Executing the migration
This is where the planning turns into action. Here, you’ll configure the right modes, transition users in stages, and connect the telephony components that make Teams a true SfB replacement. The execution phase also demands thorough testing and ongoing monitoring to ensure the change sticks.
Configure coexistence modes in Microsoft 365 Admin Center
Depending on the size of the organisation, migrate users in waves, starting with pilot groups
Enable telephony via Operator Connect, Calling Plans, Direct Routing or Teams Phone Mobile
Update services such as DNS (If required), configure SBCs (If Direct Routing), and test thoroughly
Monitor usage and adoption analytics in real time
How to minimise downtime and ensure business continuity
Downtime during migration can be costly when it comes to productivity and user confidence and morale. Maintaining uninterrupted operations while transitioning to Teams requires meticulous planning, phased execution, and early issue detection.
Our expert-backed roadmap can help you keep the lights on throughout your migration.
Pilot with a cross-section of users
Start small and safe. Launch your migration with a representative group of users spanning departments, seniority levels, and technical fluency. They should also be on board with the change so they can support user advocacy when you roll out to a larger group.
By piloting with a smaller group of users, you can validate coexistence settings, catch functional or compatibility issues early, and collect targeted feedback.
Communicate early and often
Transparent communication is vital for reducing surprises and managing expectations. Keep your teams looped in with:
Clear timelines and role-based FAQs
Policy change alerts
Leadership briefs
Provide training tied to real-world workflows
Training isn’t just about features and ensuring your users know how to use Microsoft Teams. It also spans transition and change management. Consider running workshops or creating video guides that replicate day-to-day activities. Be sure to include chat, calls, meetings, and file sharing as a minimum.
It’s also worth creating a bank of on-demand resources that users can refer back to. For example, FAQs, quick reference guides, champions etc. By planning this training and carrying it out effectively, you’ll support hands-on learning that maintains productivity and confidence.
Keep hybrid environments stable until full cutover.
Maintaining a stable coexistence is critical for avoiding a breakdown in communication. You’ll need to:
Leverage hybrid connectivity - a prerequisite for transitioning users to TeamsOnly
Carefully manage coexistence modes for seamless communication
Test external interoperability, particularly when migrating external users or legacy integrations
If all of this seems a bit complicated, partnering with an expert like Nasstar lets you tap into proven processes, rapid troubleshooting, and lessons learned from complex, multi-site migrations.
Strategies for a smooth transition
Planning to migrate from Skype for Business to Teams is as much a cultural shift as it is a technical one. Ensuring the process is smooth comes down to preparing your people, tightening your governance, and creating a rollout sequence that suits your risk tolerance and change appetite.
Champion networks
Internal advocates can dramatically accelerate adoption and reduce resistance. Select respected individuals from across departments who are willing to test early, share best practices, and support colleagues informally. Provide early access to Teams features, tailored training, and recognition for their role in the change.
Shadow IT discovery
Before rolling out Teams across your business, identify any unauthorised collaboration or messaging tools already in use. If left unchecked, these can pose compliance risks or fragment communication. You can use IT discovery tools or carry out a network traffic analysis to spot unauthorised tools. Then, you can either migrate those workflows into Teams or provide alternatives.
Device strategy
Teams performance is only as good as the hardware supporting it. Standardising on Teams-certified headsets, webcams, conference phones, and room systems will improve call quality and reduce troubleshooting complexity. If your budget allows, it’s worth refreshing older devices as part of the migration so users start fresh with optimised equipment. Plus, who doesn’t love a new bit of kit!
Staggered rollouts
Deploying Teams to everyone overnight can cause chaos unless your culture thrives on rapid change. A staggered rollout allows for targeted training, easier troubleshooting, and lessons learned from each wave. The exception? If your business has a strong appetite for change, a well-prepared “big bang” can deliver faster benefits but only with flawless preparation.
Post-migration best practices for success
Getting to the end of your migration from Skype for Business to Teams is an achievement, but it’s not the end of the journey. The post-migration phase is about optimisation, adoption, and continuous improvement.
By actively monitoring performance, listening to users, and evolving your setup, you can ensure Teams remains a reliable, secure, and valued platform long after go-live.
Here are some top tips for success:
Monitor call quality via Teams CQD
Keep feedback loops open and act on them
Review and replace legacy integrations
Deploy Teams Rooms for meeting equity
Maintain governance and lifecycle policies to prevent sprawl
Common challenges in migrating from Skype to Teams and how to overcome them
Even with the best planning, migrations rarely happen without a bump or two in the road. Understanding the common pitfalls ahead of time, and having migration strategies ready, can help you avoid disruption, reduce frustration, and keep your project on track.
Resistance to change - Engage early, train often, and tailor training to user roles
Feature mismatch - Document all required features pre-migration and implement workarounds or replacements before cutover
Legacy infrastructure - Use Direct Routing or Operator Connect to extend existing telephony investments
Poor call quality - Optimise networks, enforce QoS, and mandate certified devices
Skype to Teams migration checklist
Before you press “go” on your migration, make sure you’ve covered the essentials. This Skype to Teams migration checklist distils key steps from planning through to post-migration follow-up, giving you a quick reference to keep your project on track and your users supported.
Stakeholders identified and engaged
Skype usage audited
Migration path selected
Network & infrastructure assessed
Comms & training plan created
Teams voice strategy defined
Migration waves planned
Post-migration support in place
Feedback loop enabled
Final word
Migrating from Skype for Business to Teams is a strategic opportunity that can really modernise your communications, improve resilience, and position your organisation for the future of work. Plus, with the right plan and the right partner, you can deliver a seamless, disruption-free migration that actually boosts productivity from day one.
Nasstar has delivered successful SfB to Teams migrations in sectors from retail to legal and finance to the public sector, always with an eye on business continuity, security, and adoption.
If you’re ready to make Teams the foundation of your workplace, now’s the time to act. Contact us today.
