Microsoft 365 or Google Workspace for a small office: how to choose and how to switch

The answer depends on how your office already works

Microsoft 365 is usually the better choice for an office that lives in Outlook, Word and Excel, exchanges Word documents with clients, or runs legal, dental or insurance software that integrates with Microsoft. Google Workspace is usually the better choice for a team that already works in Gmail and Google Docs in the browser and wants a simpler setup. Both can be secured to the same standard, and neither is a backup on its own. The right pick is the one that fits your software and your people, not the one with the longer feature list.

I am Anthony Omini, owner of Cross River Tech. We set up, migrate, license and manage both platforms for offices across Dallas–Fort Worth, and we are a Microsoft Cloud Solution Provider. I do not push one over the other. This guide covers the questions I ask before recommending either, and what a switch really involves.

Start with the software you cannot change

Before comparing email features, list the programs your office cannot work without: the case management system, the dental practice software, the agency management system, the accounting package, the CAD tools. Then ask each vendor which email and document platform it supports and how. Some line-of-business software expects Outlook on the desktop, some works best with one platform's calendar, and some does not care at all.

This one question settles more decisions than anything else. If your practice software sends documents straight into Outlook and Word, moving to Google means fighting your most important tool every day. If everything you use runs in a browser, the decision opens up, and comfort and cost take over.

How each one feels day to day

Microsoft 365 business plans center on the familiar desktop apps, Outlook, Word, Excel and Teams, with files in OneDrive and SharePoint. People who have spent years in Word and Excel, and offices that trade heavily formatted documents with clients, courts or carriers, tend to be happiest there. The desktop apps are powerful, and that power comes with more settings to manage.

Google Workspace is built around the browser: Gmail, Calendar, Docs, Sheets, Drive and Meet. Several people editing the same document at once feels natural, there is less installed on each computer, and new staff usually find their way around quickly. The tradeoff shows up when a client sends a complex Word file or a spreadsheet full of macros, and someone has to make sure it survives the round trip.

Neither is wrong. A design studio that collaborates in the browser all day can do very well on Google, and a law firm built around Word templates and Outlook folders would struggle anywhere else. Ask your staff which tools they open first thing in the morning, and take the answer seriously.

A quick way to decide

If you want a shortcut, run through these questions with whoever knows the office best. Most offices land clearly on one side after five minutes, and the ones that do not usually have a software requirement that settles it once they call the vendor.

• Does our most important software require or prefer Outlook on the desktop? Lean Microsoft.
• Do we exchange heavily formatted Word or Excel files with clients every week? Lean Microsoft.
• Do most of us already work in Gmail and Google Docs in a browser? Lean Google.
• Do several people edit the same documents at the same time all day? Either works, Google feels simpler.
• Are we already on one platform and mostly happy? Stay, and fix the configuration instead of moving.
• Is the real complaint slowness, spam or confusing sharing? That is usually a setup problem, not a platform problem.

Licensing: where small offices overpay

Both platforms sell several tiers, and most small offices end up paying for more than they use. The four patterns I find most often when I review a license bill are everyone placed on the top tier, shared mailboxes such as info or billing using paid seats when they do not need them, former employees still licensed months after leaving, and desktop Office paid for on accounts that only ever use webmail.

We source licenses through a distributor and pass them through at the published subscription price, and because we see every invoice we can match each person to the tier they actually need. Whichever platform you choose, ask for licenses as their own line on your IT bill. My guide on what managed IT costs a small office explains how to compare the service fee separately from the subscriptions.

Security is the same job on either platform

The platform you pick matters much less than how it is configured. A default tenant on either service leaves gaps that attackers know about, and the same handful of settings close most of them.

Microsoft states that, based on its own experience, more than 99.9 percent of common identity-related attacks are stopped by using multi-factor authentication and blocking legacy authentication. CISA puts it more plainly: people who turn on multi-factor authentication are significantly less likely to get hacked, and any form of it is better than none. Those two settings cost nothing extra on either platform, and they are still missing in a surprising number of small offices I take over.

If an account in your office has already been taken over, the steps are different and time matters; see the warning signs of a hacked business mailbox and what to do first. For everyone else, this is the baseline we apply to both platforms before anyone starts working in them.

• Multi-factor authentication on every account, including administrators
• Older sign-in methods that cannot use multi-factor authentication switched off
• Spam and phishing filtering, with links and attachments checked
• SPF, DKIM and DMARC records so criminals cannot easily send mail as your domain
• Alerts for unusual sign-ins, new forwarding rules and mass deletions
• Remote wipe of company data on a lost or stolen phone or laptop

Neither platform is your backup

A common assumption is that because email and files live in Microsoft's or Google's cloud, they are backed up. The services are built to stay available, which is not the same thing as protecting you from a deleted folder, a ransomware infection that syncs encrypted files to the cloud, or an attacker with administrator access. We back up both platforms with a separate service outside the tenant, several times a day. I go into the details in the backup myths that leave small offices exposed.

When you compare quotes for either platform, check whether that separate backup is included or quietly left out. It is one of the easiest items to drop from a price to make it look lower, and one of the most expensive to discover missing after someone empties the wrong folder.

What a switch actually involves

Moving email and files sounds risky, and done carefully it is mostly invisible to staff. We move offices from hosting-company mailboxes, personal Gmail or Outlook.com accounts, on-premises Exchange servers, and from one platform to the other. The process has four parts.

• A short conversation about where email lives today, how many people there are, current spend and what is not working, ending in a recommendation
• Building the new tenant, verifying the domain, applying the security baseline and copying mail and files in the background ahead of time
• A cutover that usually happens in one evening, followed by a final sync that catches the last few hours of mail
• Connecting Outlook or Gmail, files and phones for every person, with a walkthrough, while the old system stays readable for a while as a safety net

Should you run the migration yourself?

A two-person office moving from one simple mailbox to another can do it with patience and the platform's own tools. Beyond that, the risks multiply. Domain records have to change at the right moment or mail bounces. Shared mailboxes, calendars, contacts and permissions do not always come across on their own. Phones keep trying the old settings. And if the security baseline is not applied before people start working, the new tenant opens with the same gaps as the old one.

The most common problem I am called in to fix after a self-run move is not lost mail. It is the quiet leftovers: the old provider still billing for mailboxes nobody uses, a printer that can no longer scan to email, a shared calendar that half the office cannot see, and an administrator account with no multi-factor sign-in because it was created in a hurry on migration night. None of these stop work on day one, and all of them cost time or money later.

Law firms have retention and litigation holds to respect, and medical and dental offices need the new mailboxes set up with HIPAA-oriented safeguards from the start. The platform alone does not make an office compliant; the configuration and the habits do. We quote setup and migration as a fixed project, and after the move, adding a new person is usually done the day you ask.

Getting a recommendation for your office

If you are deciding between the two, or you suspect you are on the wrong one, call and tell me what software you run, how many people you have and what frustrates them. That conversation is usually enough for a clear recommendation and a fixed quote for the move. We do this for offices across Dallas and the rest of Texas remotely, with on-site help in the metroplex when a migration day needs hands at the desks.

If you are already on the right platform and simply want it configured and looked after, that is part of a managed plan, or we can handle one-off changes hourly with no contract.

Questions people ask me