We’ve covered some “Why” questions and the “What” questions in our Essential Microsoft 365 Migration Questions blog posts. Two Ws down, three to go. Next up are “When” questions you should be asking.

Essential Microsoft 365 Migration Questions: When?

When should we start?

As soon as possible, right? It seems obvious enough. However, before you ever get started actually moving your content, you’re going to want to make sure you include several weeks – maybe even months – of planning, analysis, design and development activities. If you’ve answered the “What?” questions, then you should have some idea of the scope of your content that needs to be migrated. Depending on your scope, you may require some future state design or automation scripts. You’ll certainly need some time to make sure you have any migration tools, scripts or processes in place.

When do we need to be finished?

This question, in many cases, can provide a lot of pressure on the previous question. Especially when it’s being driven by a need to be off your current platform to avoid additional licensing costs or some other date based deadline. The answer to this question will help not only determine the start date but also staffing questions. If you have 10,000 sites to move and 10 weeks to do it…you’re going to need a small army (and maybe a miracle or two).

If you don’t have a “drop-dead” date, that’s great too, as it removes some pressure from the situation and allows you to focus less on speed and more on quality.

When can’t we migrate?

Almost every organization has some period of time that just isn’t a good time to be shuffling people’s stuff around. Be it end-of-month reporting, corporate “blackout” periods, or the fact that the office turns into a ghost town after the first week of December…there’s always something. These factors should be considered into any migration schedule and plans.

When do we send out communications?

Another communication question – it’s a theme; and for good reason. Migrations are disruptive and, by their nature, imperfect projects. Regardless of what kind of migration you’re doing, things are never the same at the end. Things are better, hopefully, but they’re certainly different and if there’s one thing people generally aren’t fans of it is massive changes. The most technically successful migration can be a complete failure if users aren’t happy.

Knowing what communications to send, and when to send them is often half the battle. Keeping your users informed of what is happening, what they can expect, and what they need to do is a critical component of a migration – especially for larger organizations.

When do we need to involve users?

Keeping your users informed is important, but sometimes their direct involvement is going to be required. For instance, if you’re planning a trial or pilot migration to end-to-end test your migration plan, using real sites with real owners can help identify rough edges. After all, no one will know their site better than the people who use them.
You’ll also probably want to include users in some sort of validation or “UAT” period. Maybe involve some “champions” by inviting them to some “train the trainer” sessions.

The specifics of when you should get people involved is largely dependent on your organization but should be considered. After all, anything you can do to improve user experience and adoption is going to do wonders for improving your chances of success.


Migrations can be an unwieldy and chaotic kind of project. Through careful planning and time management skills, and by understanding the questions asked in this blog post, you can add some process to help quell the beast and ensure that everyone makes it to the finish line in one piece.

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