5 Tips to lay the groundwork for a successful migration to Teams Phone – Ep.76 | SS1

Changing to a new collaboration solution may seem impossible at first. But it doesn’t have to be.

Migrating to Microsoft Teams Phone is more than a simple technology upgrade — it’s a transformation that can redefine how organizations communicate and collaborate. 

With its seamless integration into the Microsoft 365 ecosystem, Teams Phone offers businesses the tools to empower users, improve efficiency, and modernize workflows.

You already know this.

However, as with any large-scale migration, success depends on thoughtful preparation and strategic execution. 

In Episode 76, Segment 1: Laying the Groundwork for Migrating to Teams Phone, Teams expert Matt Carlson shares: 

• Expert insights from three major Teams Phone migrations 
• His personal experience across education, healthcare, and enterprise sectors 
• Key lessons for organizations planning their own transition

#1: Take a softphone-first strategic approach

One of the first lessons Matt emphasizes is the shift from physical desk phones to a softphone-first strategy. While his early migrations replaced like-for-like hardware, the limitations of traditional devices quickly became apparent.

“A softphone-first approach simplifies deployment, reduces costs, and gives users the flexibility to work from anywhere,” Matt explains. Whether on a desktop, laptop, or mobile device, Teams Phone empowers users to handle calls seamlessly across platforms.

While there are exceptions—such as common area phones or executive offices—Matt stresses that these should remain the exception, not the rule. By minimizing desk phones, organizations can focus on providing a streamlined, modern communication experience.

#2: Get executive sponsorship as early as possible

Strong leadership is critical to driving change, and Matt highlights the role of executive sponsorship in setting the tone for a successful migration.

“When leadership supports the move and frames it as a positive evolution, employees are much more likely to embrace the change,” he notes.

Effective sponsorship helps cascade messaging throughout the organization and fosters trust and buy-in at every level. In Matt’s experience, leaders who position the migration as an opportunity to modernize and improve workflows see greater acceptance across departments.

#3: Upskill your IT Teams for success

IT professionals know how important upskilling is today.

For IT teams managing legacy systems, the transition to Teams Phone can be a challenge — but it’s also a chance to grow. Matt’s approach has always focused on empowering IT staff through upskilling and training.

“Encouraging staff to embrace the new skills they’re learning makes all the difference,” Matt says. 

By providing hands-on training and positioning the migration as an opportunity for professional development, organizations can retain institutional knowledge and build team confidence. 

The end result: higher adoption rates and a boost in user satisfaction.

#4: Frame the message for end-user adoption

End-users often resist change. 

This is especially true when it means giving up familiar tools. 

Matt emphasizes the importance of framing the migration in a way that highlights its benefits.

“This isn’t just a replacement—it’s an upgrade that empowers you to work how you want, where you want,” Matt shares as part of his messaging strategy.

By showcasing tangible benefits like flexible device options, custom voicemail settings, and seamless Outlook integration, his team turned initial skeptics into advocates. 

The key is balancing positive messaging with realistic expectations and ongoing support.

#5: Define real business needs

Every organization is unique, and successful migrations start with understanding the specific needs of the business. 

Matt emphasizes the importance of site audits, stakeholder interviews, and workflow analyses to identify priorities.

“It’s not about recreating the old system — it’s about modernizing processes to align with today’s technology,” he explains. By collaborating with departments to simplify outdated call flows, Matt’s team delivered a migration that not only met expectations but exceeded them.

This process is discover-driven in nature, but by the end of it, you should be able to answer:

• What processes does the phone system need to support and enable?
• How do teams communicate and collaborate, internally and externally?
• What methods of communication are must-haves?
• What methods of communication are nice-to-haves?
• What features do power users need?
• What integrations are essential?

Why Teams Phone over-delivers

Matt believes Microsoft Teams Phone consistently exceeds expectations, thanks to its flexibility, scalability, and user-centric features that make it a powerful communication tool. Popular features include:

• Multi-Device Access: Use Teams on desktop, mobile, or web browsers.
• Streamlined Call Management: Features like simultaneous ring, call forwarding, and voicemail integration empower users without IT intervention.
• User Empowerment: Teams Phone allows users to customize their communication experience in ways that legacy systems cannot match.

“Teams Phone empowers users to handle their calls how they want, without being boxed in by outdated systems,” Matt says.