Microsoft 365
Most of the value is in settings nobody has looked at.
Mail that arrives, files only the right people can reach, and an honest answer about what you are paying for every month.
You almost certainly already have it
Nearly every business I sit down with is already on Microsoft 365. So this is rarely a question of whether to buy it. It is a question of whether what you are paying for matches what you use, and whether the parts that protect you were ever switched on.
The defaults were written for an organization with an IT department to tighten them. If nobody has been through yours, they are still sitting exactly as they arrived, which for most of them means open.
Here is the one that pays for itself in an afternoon. A shared mailbox — info@, billing@, office@, the address that belongs to the business rather than to a person — does not need its own license. It is included. I regularly find businesses paying a full seat every month for an address nobody signs into. It is not a large amount of money. It is just money for nothing, every month, for years, and nothing anywhere will ever point it out.
What I look at
Four questions, none of which require changing anything you are happy with.
What you are licensed for
Basic, Standard and Premium are genuinely different products, and the gap between them is mostly security rather than features you would notice. Sometimes the step up is the best money in the whole budget. Sometimes it buys a capability you will never open. I will tell you which one you are looking at.
Who can reach your files
Sharing links that work for anyone who has them, forever, long after the project ended and the contractor moved on. They were created by people doing their jobs, which is why nobody thinks to go back and close them. They are usually the largest unlocked door in the building.
Whether your mail arrives
If your invoices land in customers’ junk folders, the cause is almost always three DNS records that most small businesses have never been told about. It is a half hour of work, it costs nothing, and the difference is whether the people you are billing ever see you.
What happens when somebody leaves
Most organizations do one of two things. They delete the account and lose the person’s files along with it, or they keep paying for the seat indefinitely because nobody is sure what is in there. There is a correct answer in the middle, and it takes about ten minutes if you know it exists.
What the top tier actually contains
The tier names tell you nothing, so here is the part worth knowing by name. Three things account for most of the price difference, and all three are the sort of thing that only matters on a day you were not expecting.
Entra ID is the list of who works for you and what each of them is allowed to sign into. Put like that it sounds like bookkeeping. What it actually buys is rules: require a second factor to sign in, refuse sign-ins from countries you do not operate in, and switch off one person’s access to everything at once on the day they leave. One action instead of remembering nine.
Intune manages the laptops and the phones. It puts the same settings on every machine without anyone walking desk to desk, and it does the thing people ask me for first — taking company mail off a phone that has been lost, or off an employee’s own phone on their last day, without touching a single one of their photos.
Defender for Business is protection you can see. The difference from what is already on the machine is not really detection. It is that one screen tells you which computer has the problem, instead of a warning sitting on a monitor in an office where nobody is standing.
And the honest half. Intune is real work to set up, and it earns that back when the machines belong to the business. If you have six people who each use their own laptop, it may cost you more administration than it saves, and I will tell you so rather than turn it on because it came with the license. The sign-in rules are the opposite case — close to pure gain, cost nothing extra, and take an afternoon. Those I will push you toward.
One more worth knowing about, although it is not included. Teams Phone makes Teams your actual telephone system. The business number rings on the laptop, on the phone in somebody’s pocket and at the desk, voicemail arrives as mail, and there is no separate handset contract sitting underneath any of it. I ran DataStream’s own number on it for years. It is a good product, and it is one of the few cases where consolidating onto something you already pay for genuinely simplifies the week rather than just moving the bill. It costs extra — when I last looked it was around fifteen dollars a month per person with calling included, though Microsoft moves these figures and you should check rather than take my word for it. Whether that is worth anything depends entirely on what you are handing your current phone company every month for the same service. For a good many small offices, that comparison is not close.
OneDrive is not a backup
This is the single most common misunderstanding I run into, and it is an easy one to hold, because for years everything has worked beautifully.
OneDrive and SharePoint are sync. Sync is very good at making sure every copy is identical — including on the day that identical is the problem. Delete a file and it deletes everywhere. Overwrite a good version with a bad one and the bad one travels to every device you own before you have finished regretting it. If something encrypts your files, the encryption syncs too, at the speed of your internet connection.
There is a recycle bin and there is version history, and they are real. They buy you days, sometimes a few weeks. They are a safety net for a mistake you notice quickly, not a copy of your business, and the retention clock is shorter than almost anybody assumes.
Microsoft is responsible for keeping the service running. Keeping your data is yours. That division is written plainly in the agreement and it surprises people every time.
So the question I ask is the same one I ask about everything else: if it went wrong this morning, what would you get back, and has anyone ever tried? More on that here.
If you are moving to it
From a server in the back room, from an old hosting mailbox, from Google. The files are the easy half. The mail is where the risk lives, because there is a window during the switch when a message can arrive at the place you just left, and nobody finds out until a customer asks why you never replied.
So the old system stays running until the new one has been proven, and the cutover happens when nobody is trying to work. Nothing gets turned off to save a few days of overlap.
I have never met anyone who regretted moving their mail. I have met plenty who regretted how it was moved.
A note for nonprofits
Microsoft’s nonprofit program has changed, and not in your favor. Offers that were grants have become discounts, and the number of seats covered is smaller than it was. If your budget was built on the old terms, it is worth finding out where you stand well before renewal rather than during it.
I will check what you are actually entitled to now. That part is free, and it is worth doing even if the answer turns out to be that you are fine.
Not sure what you are paying for?
Hardly anybody is, and it is not a failing. The billing page is written for accountants and the admin center is written for administrators, and neither of them says in plain language what you have got.
Show me what you are subscribed to and I will tell you what it does, what you are using, and what you could stop paying for. No charge, and no obligation afterwards.