How to plan ahead for cloud migration frustrations

Moving furniture into your friend’s new dorm usually involves beer and pizza as a reward. Let’s hope the IT team that helped Babson College’s big digital move in 2023 got enough slices.

Over the span of about six months that summer, the Massachusetts-based school, according to its CIO Patty Patria, migrated more than 20 terabytes of data for 6,000-plus campus employees. The emails and documents—and all the links and connections associated with them—went from multiple cloud environments, including Google Workspace, to one consolidated platform: Microsoft 365.

Patria and two IT pros who’ve conducted similar migrations shared with IT Brew how to prepare so data arrives safely at its new destination—and how to respond effectively if it doesn’t.

“Any time you change an interface that somebody’s been using for five, 10, 15, 25 years, that’s a challenging thing for them, and so you have to be very careful of planning,” Patria told us.

Let’s get moving.

Software-as-a-service (SaaS) migrations are common during mergers and acquisitions, when the consolidating companies have clashing platforms. Babson, however, migrated data to reduce storage costs and improve collaboration between students and teachers, Patria said.

BetterCloud’s 2025 “State of SaaS Security,” which polled 568 US-based IT pros, found that the average company reduced their SaaS apps from 2022 to 2024 and orgs now have fewer SaaS applications than in 2021.

Clean it up!

Digital storage can be a bit like your old closet: filled with years of stuff. Patria and her team monitored active and inactive users and made decisions regarding which data would make the trip—and how much mail to bring over, for example. “It’s really reviewing, if we haven’t accessed this data more than two years, three years, five years, do we need to keep this data?” Patria said.

Richard Harbridge, CTO at 2toLead, recommended companies perform a security and compliance audit of existing data to find sensitive, regulated content like PII, financial numbers, or health info across your SaaS repositories like Google Drive and Slack.

“If you find, for example, documents subject to GDPR or HIPAA, you’ll want to ensure equal or better protections in M365 or decide if that data should even move at all,” Harbridge wrote to us in a follow-up email.

Everything is different now

A manual file copy from Google Drive to Microsoft’s OneDrive will not retain sharing permissions, version history, or external share links; migration tools (like ShareGate for migrating permissions) help with the effort, in theory. Some elements still must be reconfigured at the destination.

One of the toughest days for Patria and her staff, she said, occurred when documents arrived in unexpected condition. A third-party vendor had capabilities to migrate files over with unique permissions, Patria said, but the permissions were so unique that they didn’t carry over and required ongoing maintenance and discussions.

Each non-Microsoft SaaS has elements that don’t have a one-to-one counterpart in Microsoft 365. Google Forms, for example, cannot be auto-migrated and must be recreated in Microsoft Forms or exported to a PDF before transfer, Harbridge noted in his follow-up email, and Slack emoji reactions won’t always export into Teams. Email formatting may change, and connection points, like a Jira ticket pointing to a Google file, may break.

Mapping, however, leads to a possibility for upgrades and opportunity, Harbridge said, like upgrading to multi-factor authentication or activating data-governance features in, say, Microsoft Purview.

“It’s a great opportunity, since you have disruption, to change things and improve your security posture,” he told us.

Phase closed

Migrations can occur in phased content batches or a “big bang” option—one preferred by Will Thomas, managing director and cloud optimization lead at Protiviti—that stages and loads up all content for migration while tests and pilots occur. Then the team can spend a weekend syncing a smaller workload: any updated, new, or removed data since that primary staging execution. That kind of “bang,” also known as a cutover, still requires “hypercare” to assist users with questions. Thomas said this support can include “ask me anything” sessions, or even a proactive, concierge-style treatment where the IT pro contacts users.

Harbridge, however, says there is no big bang: “Everything is phased and everything is scheduled.” When migrating file data from file shares to SharePoint, one might do an initial bulk transfer over a weekend, according to Harbridge, followed by incremental “delta” changes, which migrate any data that changed since the last transfer.

He recommends extra padded support hours for global users and the employees catching up after hours. “A lot of this stuff doesn’t happen during core time,” he said.

In a follow-up email to IT Brew, Patria said the IT team performed 65 training sessions, including office hours, and instructed a total of 96 people during the initial roll-out; she said the school offers ongoing training.

Babson users moved from Google Drive to Microsoft’s combination of OneDrive for personal data and SharePoint for shared documents.

Learning how to access documents in a new platform proved to be a tough challenge for some users, Patria said.

“Every time you do any one of these projects, as much change management and communication that you do, you could probably always do a little bit more,” Patria told us.

The next move

A big driver for SaaS migrations is that companies want to use AI—and they can’t as easily with data fragmented across legacy SaaS tools, according to Harbridge. Patria said the migration ultimately allowed them to standardize in Microsoft’s cloud and more easily work with Microsoft’s Copilot tool—another big move.

“I think cloud platforms set you up for greater transformations in other areas,” she said.