Rethinking Migrations: Why Prioritizing the Employee Experience Enables AI Strategy Faster

Rethinking Migration: It's About People

Think about the last time your company moved or upgraded a major technical platform. Was it treated like a checklist project to migrate the data, flip the switch, and hope everything works? In the world of enterprise IT, migrations have too often been seen as purely transactional projects. Move the content, turn off the old system, and assume people will just adapt overnight.

At Rightpoint, we’ve learned that a successful digital workplace migration is fundamentally about people. Yes, moving data and configuring technology is critical, but if your employees aren’t on board and empowered, the project can fall flat. Research backs this up: enterprises lose an eye-opening $1.14 million per week in productivity because employees struggle with poorly adopted digital tools.

In fact, 38% of digital transformation investments are wasted due to lack of user adoption. If your migration approach ignores the human factor, you’re leaving a lot of value on the table. Why would you risk migrating an underperforming or underwhelming experience when you could be using it to drive that value back into your people?

So, what does a people-first migration look like and why is it important? 61% of leaders say poor digital experiences can drive employees to quit. It’s clear that every technical decision needs to be made with the employee experience in mind. Instead of asking, “How do we move this data?” we ask, “How will this make work better for our teams?” It’s a shift in mindset from IT-centric to human-centric. This shift in the approach enables a forward-facing approach, one that is intentional and strategic. AI is moving faster than anyone can predict, so the ability to move the right content and data into the right places is the most important step in that journey.

Getting Started With a Migration: Blending Data With Empathy

Planning a migration is both an art and science. On the data side, Rightpoint leverages decades of experience and analytics to scope and sequence the work with precision. But the secret sauce in our execution is the user-focused art: we factor in how each choice will impact employees day-to-day.

• Content Audit & Mapping: We start by auditing the content and collaboration spaces people use today. Rather than a blind “lift-and-shift” of everything (which just drags along clutter), we identify what content truly matters. On many projects, we end up paring down 60% or more of legacy content, streamlining information so employees find what they need without wading through ROT (redundant, outdated, trivial content). Why migrate a thousand outdated pages no one has touched in 10 years? We’d rather focus on the content that keeps the business running daily. This curation makes the new environment less chaotic and more useful from day one.

• Stakeholder Engagement: Ever seen an IT project derail because a key department felt left out? We have, and it’s not pretty. That’s why we hold workshops and interviews with stakeholders early and often and specifically not just IT owners, but business sponsors, power users, and content admins across the organization. These conversations surface critical insights: which business goals need to be supported, where the pain points are, and what “success” looks like in human terms. By building alignment up front, our plans reflect real operational realities and user priorities. Stakeholders who feel heard become champions for the project, which is invaluable when it’s time to roll out changes.

• Technical & Cultural Readiness: A migration plan isn’t just about counting terabytes or site collections; it must account for people’s readiness. We assess technical complexity and the cultural complexity. Do employees have the skills and appetite for a new tool? Is there executive support for change? We bake in time and resources for change management, training, and support, not simply stopping at an Minimal Viable Product (MVP) or only adding the “nice to haves.” For example, if a company’s workforce is used to a very different legacy platform, we might plan extra hands-on coaching. This way, when launch day comes, both the systems and the people are prepared.

All of this means our recommended migration plans might feel a bit more extensive than a purely technical proposal. And that’s the point – we’re estimating the effort to do it right. By being thorough, we avoid nasty surprises late in the game (like discovering critical content wasn’t migrated for a team, or that nobody budgeted for training, etc.). In the long run, a user-centric plan saves time by preventing rework and frustration.

Proven Track Record: Experience You Can Trust

This isn’t just theory for us, Rightpoint has a deep well of experience in digital workplace transformations, and decades of delivering results at scale. We bring the credibility that comes from having “been there and done that” in some of the toughest migration scenarios.

We’ve encountered and overcome the common pitfalls, from tricky legacy data formats to skeptical user bases. Each migration is its own mountain, and we’ve scaled it in diverse environments for financial services, healthcare, retail and more, all of which have industry specific processes and guidelines that need to be factored into the process.

Rightpoint’s expertise is also recognized by the industry. We’re proud to be Microsoft Gold Partners, multiple time Microsoft Partner of the Year, and are recommended by Microsoft as experts in digital workplace adoption and migration. Our work has even caught the attention of analysts: our employee experience transformations have been recognized by HFS Research and others. But the best proof is in the outcomes for our clients. Many have seen tangible improvements like a double-digit increase in employee engagement scores post-migration, faster project delivery times thanks to better collaboration tools, and significant reduction in maintenance costs by retiring old systems and most recently a quicker adoption path to AI tools and productivity gains.

Why Migrate Now? (Looking at 2026 and Beyond)

If you’re thinking, “This all sounds good, maybe we should plan this for next year or the year after,” it’s worth noting the clock is ticking for many organizations. There are some compelling industry trends that make a strong case not to wait too long on your digital workplace migration:

• Legacy Platforms are Sunsetting: A number of older collaboration and intranet platforms are reaching end-of-life or end-of-support in the next couple of years. For example, Meta has announced it will shut down the Workplace from Facebook platform by June 2026. Microsoft has a timeline to disable SharePoint Add-In model for the “classic” sites in April of 2026 and retire SharePoint 2016 and 2019 features by July 2026. If your company relies on any tools that are being phased out or heavily altered, moving sooner avoids the scramble of a last-minute migration to avoid downtime or security risks. It also means you won’t be forced into a hasty move on someone else’s timetable but instead can migrate on your own terms, strategically.

• Stay Ahead of Disruptive Updates: Even if a platform isn’t being outright killed, major updates can be disruptive if you’re not prepared. Think about how Microsoft is rapidly rolling out new updates to Copilot and Viva, or how Teams keeps evolving with new integration capabilities. By migrating to a modern, flexible environment now, you position your organization to absorb these innovations smoothly. Delaying might mean missing out on new features that can increase ROI and employee satisfaction, while removing shadow IT concerns. Early adopters of modern platforms are currently leveraging things like AI-enabled search and advanced analytics increasing productivity and talent retention.

• Boosting Adoption & Engagement: Companies with modern digital workplaces have an edge: their employees are more likely to feel connected, informed, and able to do their jobs effectively. For instance, a recent global survey found that employees waste 353 hours per year due to poor digital experiences. That’s almost 9 weeks of lost productivity annually per employee. A well-executed migration can recapture a lot of that lost time by providing tools that are easier to use and knowledge that’s easier to find. And by orchestrating a migration now, you’re telling your workforce, “We hear you, and we’re investing in making your day-to-day work easier.” On the flip side, if you wait until 2026 and rush a migration only because the old system is finally shutting off, you miss the opportunity to frame it as an employee-centric improvement.

• Maximize ROI on Microsoft 365: Your company is likely already paying for M365 licenses but aren’t fully utilizing the tools to their maximum potential. Migrating from legacy systems into a consolidated digital workplace lets you turn on powerful new capabilities you already have at your fingertips. Microsoft Viva Suite, SharePoint and Teams offer advanced analytics, knowledge sharing, and AI integration that simply didn’t exist a few years ago. The sooner you migrate, the sooner you can start taking advantage of these features and the sooner they start paying back in terms of productivity and insight. According to industry data, organizations that prioritize user adoption of new digital tools achieve 18% higher ROI on those investments, because the tools get used as intended and designed. In short, you want your employees using modern tools now, not two years from now.

Waiting too long to modernize your digital workplace can put you in a risky position but by planning a migration before mid-2026, you are seizing the initiative: avoiding external pressure and capitalizing on current technology trends under your own strategic plan.

Migration Is Your Strategic Opportunity

For technical leaders, a digital workplace migration is one of those high-stakes projects that can either be seen as a headache or as an opportunity. In looking at the positive, focus on using a chance to lead a transformative change that resonates across the entire business. Yes, it’s complex. Yes, it involves coordinating tech, people, and processes. But with a human-centered approach, it’s a challenge you can tackle with confidence and turn into a game-changing, AI forward company initiative.

Rightpoint’s approach is all about marrying the technical excellence (so things work) with the human touch (so people care). By going beyond the transactional view, we ensure the investment you make in a migration yields a more connected, efficient workforce. The trends in the industry underscore that this is the right time to act. Employees are craving better digital experiences, executives are looking for measurable ROI, and the technology itself has matured to enable truly modern workplaces that were pipe dreams a decade ago, with the focus on using AI to actually solve problems.

In the end, a migration done right is not just a technical win, but a business win. It can improve how your teams collaborate, how your culture thrives, and how your company performs. As you consider the road ahead, remember that every migration is fundamentally a story about people.

Ready to lead your organization’s digital workplace into the future? By embracing a human-centered migration strategy, you can ensure that when you flip that switch, your people are not only prepared but excited about what comes next.