The First Essential Microsoft 365 Migration Questions: Why?


Our first Microsoft 365 Migration Question: Why? ‘Why’ is sometimes one of my most difficult questions to answer. It certainly was when writing that essay I mentioned in the introduction post to this blog series. It’s not always obvious as to what motivates other people to do the things they do. Sometimes it’s even difficult to know why we do things ourselves.

But, unless you’re running a one-man band of a company, you’re going to want to take a stab at answering these questions. If you do, you’ll be well on your way to convincing your users and/or leadership why this needs to be done.

The First Essential Microsoft 365 Migration Questions: Why?

Why Would We Migrate?

The answer(s) to this question may be somewhat easy to answer. It could be new features that your business has been sorely missing in your current aging environment, or that you’re finally ready to make the jump from an on-premise system to the cloud. It could just be that you’ve realized you could save money by jumping aboard a new ship.

There are plenty of valid reasons to take on a migration. Being able to identify your reasons, though, is essential to being able to convince others.

Why is This an Awesome Idea?

At one point or another, we’ve all had an idea or opinion that we just knew everyone would agree with. The intrinsic rightness of it was just self-evident. But it’s hard to be able to explain to others all the reasons why this direction will lead to a better and brighter future for your business.

Why is This an Awful Idea?

Remember that opinion from the last section – the one that we just knew everyone would agree with? And then you state said idea/opinion, people look at you like you just grew horns, and you stammer on for a bit trying to defend what you didn’t think needed defending.

While it’s certainly fun to focus on the new & shiny PROs, migrations can be quite a double-edged sword. It’s important to be pragmatic and to understand your CONs. All migrations have similar challenges. Cost, time, risk, etc.…but your organization might have unique challenges that should be identified. You should develop a list of PROs and CONs and see where that leads you.

Why Should Anyone Else Care?

This is kind of a mean sounding question, but it’s a good one to ask if you’ll need to explain why you’re moving everyone’s cheese at some point. It’s easy for techies to get excited over new stuff and just assume that everyone will appreciate them as well. However, as it turns out, most people tend to not like changes and can be quite cranky when you force it on them. Being able to explain and demonstrate how the migration is going to make their lives better and easier will greatly help increase user buy-in…and you’re going to need a lot of that during a migration effort.

On an editorial note, this could also be considered the WIIFM (What’s in it for me) sales question, but I was short a ‘Why.’

Why Now?

You’ve been on your current system for a while now. What’s changed that’s really got you considering making the move? Why not wait until next year? Being able to answer the questions can help define your sense of urgency, which will only further help you to explain why you want to do this.


Why is certainly a question that needs to be answered before making decisions. It’s no coincidence that it was chosen as the opening entry into this series, as it greatly influences other questions. You might walk away from these questions with a firm “No”, which is valid decision. But, if you’re still on the path to a migration, you’ll be well equipped to promote and defend the decision.

William HollandThe First Essential Microsoft 365 Migration Questions: Why?

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