Get the Right Microsoft 365 Fit in Minutes
The Licensing Advisor I Wish I Had
For years, I had the same conversation over and over.
A partner would call about a customer deal. An IT lead would forward me a quote. Someone newer to the field would ask, half embarrassed, what the difference between E3 and E5 actually was. Every time, the question underneath was the same one: which Microsoft 365 license is the right fit here, and how do I know?
And every time, my honest answer started with “it depends,” followed by twenty minutes of explaining the same trade-offs. Business or Enterprise. With Teams or without. What you get at each tier. What you give up if you go cheaper. When it makes sense to step up. The exact same map, drawn from memory, again and again.
I kept thinking the same thing. There should be one place I can send people. A clear advisor that points you in the right direction in a few minutes instead of twenty. I looked for it. I never found one that did what I needed. So I built it.
It is called WhichM365, and it is free. This is the story of why it needed to exist, what it actually does, and the value it is built to deliver.
The problem nobody really fixes
Microsoft 365 licensing is genuinely hard to navigate. Not because the people who buy it are not smart. Because the surface area is enormous and it keeps moving.
Think about what someone has to hold in their head to make a good call. There are Business plans and Enterprise plans, and they behave differently. There are Frontline plans for deskless and shift staff that almost nobody explains clearly. There are security and compliance suites that sit on top. There are add-ons stacked on add-ons. There is Copilot, and now newer bundles arriving on top of all of it. And then the prices change, which they did again this year.
Most people do not have that whole picture memorized. They are not supposed to. A partner closing a deal does not have time to re-derive the entire ladder for every customer. An IT lead checking a renewal quote does not have a clean way to confirm they are looking at the right plan. Someone learning the stack for the first time is staring at a wall of acronyms with no obvious place to start.
So what happens? People guess. They copy what they bought last time. They ask the one person they know who seems to understand it, which for a long stretch of my career was me. None of that is a real system. It is a series of workarounds for a problem that should have a clear front door.
The reference material exists. Microsoft publishes detailed feature comparisons, and there are excellent maps of what every plan includes. But a reference table answers “what is in this plan.” It does not answer the question people actually walk in with, which is “what should I choose, and why.” Those are two different jobs. The map shows you the territory. It does not tell you which road to take.
That gap is the thing I kept running into. Plenty of places to look up features. No clear place to get a decision.
Why I finally built it
I have spent fourteen years in enterprise tech. A lot of that time was partner-facing, helping people make sense of exactly these kinds of choices. I know the stack. And even with that background, I still found myself wishing for a simpler way to give someone a fast, trustworthy answer.
That is the part worth sitting with. If someone who does this for a living wants a clearer tool, imagine how it feels for the person doing it once a year at renewal time, or the newcomer trying to learn it at all.
So I made the thing I wished I had back in those roles. Not a course. Not a gated download you trade your email for. A working tool that anyone can use in a few minutes.
The goal was never to replace a real licensing conversation. A good conversation with a partner or a Microsoft expert is still where the final, exact decision should land. The goal was to make that conversation start from a smarter place. To get someone from “I have no idea” to “here is the plan I think fits, and here is why” before they ever pick up the phone.
That is a better starting line for everyone. The buyer comes in informed. The partner spends less time on the basics and more time on the real nuance. Nobody wastes the first twenty minutes redrawing the same map.
What it actually does
WhichM365 asks a few quick questions and lands you on a clear recommendation. Not a maybe. An actual plan to consider, with the reasoning attached.
Here is what you get on the other side of those questions.
A clear recommendation. The license to look at first, for the situation you described. Not five options to compare in a panic. A starting point, named.
The estimated price. So you know roughly what you are looking at per user, before you ever talk to anyone. Estimates, clearly labeled as estimates, because pricing should always be confirmed with your partner. But enough to plan around.
What you get and what you give up. Every tier comes with trade-offs. The tool is honest about them. If a cheaper plan saves money but drops a capability you need, it says so. If stepping up a tier is worth it, it tells you when and why.
When to upgrade. The signals that mean you have outgrown your current plan. So the decision holds up not just today, but as the team changes.
And it covers the full range, not just the easy middle. Business. Enterprise. Frontline, for deskless and shift staff, which is the track people most often get wrong. A nonprofit pricing view, because eligible organizations pay far less and a lot of them simply do not know it. And a government cloud section for the GCC, GCC High, and DoD questions that always come up and rarely get a straight answer.
On top of that, two things keep it from going stale. There is a live feed of what is shipping next from the Microsoft roadmap, so you can see what is coming. And every feature links straight to Microsoft’s own resources, so when you want to go deeper on a specific product or capability, you are one click from the authoritative source. The tool points you in the right direction. Microsoft’s documentation takes you the rest of the way.
That last part matters to me. WhichM365 is not trying to be the final word on everything. It is trying to be the fastest path to the right answer, and an honest guide to where to learn more.
The value, in plain terms
When I think about what this is actually worth to someone, it comes down to three things. The same three things most of us would like more of in our work, every single day.
You save time. The twenty-minute explanation becomes a few minutes of answering questions. The hunt across a dozen browser tabs becomes one screen. For a partner sizing up several customers, or an IT lead checking a renewal, that time adds up fast.
You can save money. Not by playing games, but by making a better-informed decision. When you can see what each tier actually includes and what you would give up by going cheaper, you stop overbuying out of caution and you stop underbuying out of confusion. You buy what fits. And if you are an eligible nonprofit, you find out about pricing you might have missed entirely.
You make a better decision. This is the real one. A clear recommendation, with the trade-offs spelled out and the upgrade triggers named, means the choice holds up. Not just at purchase, but six months later when someone asks why you picked what you picked. You have an answer, and it is a good one.
Save time. Save money. Decide better. That is the whole point. Those are the outcomes the tool is built to deliver, and they are the reason it exists.
What it is not
I want to be straight about the boundaries, because that honesty is part of the value.
WhichM365 is an advisor, not a quote. The prices it shows are estimates to help you plan, and they should always be confirmed with your Microsoft partner before you buy. Pricing moves, and the tool tells you to verify rather than treating an estimate as gospel.
It does not replace a licensing expert. For the final, exact, contractual decision, especially for government scenarios where there are real handling rules involved, you still want a real conversation with someone who can quote you properly. The tool gets you ready for that conversation. It does not pretend to be it.
And it is not finished. It is live, it works, and it covers a lot. But there is a clear list of what comes next, and I would rather ship something genuinely useful now and keep improving it than wait for some imaginary complete version that never arrives.
That last point is really how I try to work in general. Practical over perfect. Get something real into people’s hands, learn from how they use it, and make it better.
Try it, and tell me what is missing
If you quote Microsoft licensing, buy it for your organization, or are still learning the stack, this was built for you. It is free, there is no signup, and you can use it right now at whichm365.com.
I built it for the version of me in those partner-facing years who kept wishing this existed. If it saves you some time, helps you spend with more confidence, or just points you in the right direction, then it did its job.
And if you use it and something is missing, I genuinely want to hear it. The best version of this tool comes from the people who actually use it telling me what would make it more useful. That is how it gets better.
Take a look. Let me know what you think. whichm365.com
Always Be Learning.
*Tech Simplified is an independent business and is not affiliated with, endorsed by, or representing Microsoft. Sly Gittens works at Microsoft in a separate capacity.*