We deploy Microsoft 365 for a lot of clients — and we steer some away from it. This isn't a Microsoft sales pitch. It's the assessment we'd give a business owner who called us before signing up: here's what you actually get, here's what you don't, and here's the honest answer to "is this right for us?"
What You're Actually Buying: The Three SMB Tiers
Microsoft offers three plans for businesses under 300 users. The differences matter more than the price gap suggests.
Web and mobile Office apps only — no desktop Word/Excel. Exchange email, Teams, SharePoint, 1 TB OneDrive. No offline apps.
Everything in Basic + full desktop Office apps (Word, Excel, PowerPoint, Outlook on up to 5 devices). Webinar hosting, Bookings.
Everything in Standard + Defender for Business (EDR), Intune MDM, Conditional Access, Safe Links/Attachments. Enterprise security for SMBs.
Business Basic goes from $6 → $7/user/month (+17%). Business Standard goes from $12.50 → $14 (+12%). Business Premium stays at $22. If you're evaluating now, factor in the new pricing for your annual budget.
Where M365 Genuinely Earns Its Cost
These are the reasons we recommend M365 — not because Microsoft pays us, but because these specific capabilities are hard to match at this price point.
Business Premium's security stack is a genuine deal
At $22/user/month, Business Premium bundles capabilities that used to require enterprise-tier licensing:
- Defender for Business — full endpoint detection and response (EDR) on Windows, Mac, iOS, and Android. Automatically isolates compromised machines, hunts for behavioral threats, and manages vulnerabilities. This alone cost $15+/user/month as a standalone product two years ago.
- Intune Plan 1 — mobile device management. Enforce screen lock, encryption, minimum OS version. Remote wipe a lost or stolen device. Push apps to company phones. App protection policies that keep M365 data inside managed apps.
- Conditional Access (Entra ID P1) — block sign-ins from untrusted devices or unexpected geographies. Require MFA dynamically based on risk. For a healthcare practice or law firm handling sensitive data, this is the policy layer that prevents unauthorized access even with a stolen password.
- Defender for Office 365 Plan 1 — Safe Links checks URLs at click time, not just delivery. Safe Attachments detonates suspicious files in a sandbox before they reach the inbox.
For a 20-person professional services firm — accountants, attorneys, insurance agencies, financial advisors — deploying all of this correctly at $22/user/month is genuinely the best security-per-dollar available for small businesses.
Desktop Office apps still matter for some workflows
Google Workspace's browser-based Docs and Sheets are excellent for most tasks. They're not adequate for everything. If your team does complex Excel models, mail merge to formatted Word documents, client-facing PowerPoint decks with custom formatting, or works offline on the road — the desktop apps are not optional.
Teams is a genuine Slack + Zoom + file storage replacement
If you're paying separately for Slack, Zoom, and Dropbox, switching to M365 Business Standard frequently nets savings even before the productivity argument. The integration isn't perfect, but for a 10–50 person business that doesn't have extreme workflow requirements, the consolidation pays for itself.
Compliance tooling for regulated industries
If your business handles HIPAA data, financial records, or legal documents — the eDiscovery, legal hold, audit logging, and sensitivity labeling tools in M365 have a depth that Google Workspace doesn't match. Not relevant for a landscaping company; very relevant for a 15-person law firm.
The Costs Nobody Mentions at Sign-Up
Microsoft's retention policies and recycle bins are not backup. Deleted emails recover for 30–93 days. There's no point-in-time restore for accidentally overwritten files. Ransomware that encrypts your SharePoint in-place will encrypt the synced "recovery" copies too. The Microsoft 365 Backup add-on — if you want it native — costs $0.15/GB/month billed through Azure. For a 25-person firm averaging 100 GB per mailbox, that's roughly $450/month in Exchange backup alone, before SharePoint and OneDrive. Third-party alternatives (Veeam, Datto, iDrive) typically run $3–$8/user/month all-in and are the better choice for most SMBs.
Add-on costs that add up fast
| Add-on | Cost/user/mo | What it adds |
|---|---|---|
| Defender Suite | $10 | Defender for Endpoint P2, Defender for Identity, Defender for Cloud Apps, Entra ID P2 |
| Purview Suite | $10 | Advanced DLP, insider risk, communication compliance, advanced eDiscovery |
| Defender + Purview Bundle | $15 | Both suites at a discount (~68% vs. purchasing individually) |
| Entra ID P1 (standalone) | $6 | Conditional Access — already included in Premium; needed if you're on Basic or Standard |
| Third-party backup | $3–$8 | Point-in-time restore for Exchange, SharePoint, OneDrive, Teams |
The shared mailbox trap
Shared mailboxes (info@, orders@, billing@, support@) are free up to 50 GB and are a legitimate way to manage team inboxes. The trap: if any user in your tenant ever acquires an E5 license — even temporarily, even a consultant's account added during an IT project — Microsoft's licensing terms require Defender for Office 365 P2 licenses on every shared mailbox in the tenant at $5/mailbox/month. A business with 20 shared mailboxes suddenly owes $1,200/year in unexpected licensing. We've seen this catch clients completely off guard.
Contractor and part-timer licensing
Each person who accesses M365 apps needs their own license — no sharing accounts (this violates Microsoft's terms and creates security gaps). For hourly workers who only need email and Teams, Microsoft 365 F3 at ~$8/user/month is the right fit. For shift workers who only need scheduling, M365 F1 at $2.25/user/month covers it without email. Don't pay $22/user for a seasonal employee who reads shift schedules.
Migration costs are almost always underestimated
Tooling licenses are only 15–25% of a typical migration's actual cost. The rest is IT labor, licensing overlap while both systems run, user training, and the inevitable first-week support surge. Specific gotchas for moving from Google Workspace:
- Gmail labels don't map to Outlook folders — messages with multiple labels duplicate or lose labels on import
- Google Shared Drive permissions must be rebuilt from scratch in SharePoint (completely different permission models)
- Calendar events with Google Meet attachments frequently fail Exchange's import limits
- ApplicationImpersonation (the authentication method older migration tools used) was deprecated in August 2024 and fully disabled February 2025 — any tooling not updated since then will fail silently
Do the MX record cutover on a Friday evening, not a Monday morning. Budget for 2–3x your expected support tickets in week one regardless of how smooth the migration appears.
Microsoft 365 vs. Google Workspace: The Honest Comparison
Google Workspace pricing (annual billing, current): Business Starter $7/user/month, Business Standard $14/user/month, Business Plus $22/user/month. Google increased prices 17–22% in 2025 when they bundled Gemini AI into all tiers.
| Category | Microsoft 365 | Google Workspace | Edge |
|---|---|---|---|
| Desktop apps | Full offline suite (Standard+) | Browser only | M365 |
| Real-time collaboration | Good, but secondary feel | Native; Google pioneered this | |
| Admin experience | Complex; 10,000+ settings | Simple, clean console | |
| Security (premium tier) | Business Premium: EDR, MDM, Conditional Access, DLP | Business Plus: solid but no equivalent to Defender + Intune | M365 (significantly) |
| Compliance tooling | Deep; eDiscovery, legal hold, HIPAA/FINRA tooling | Adequate; less mature enterprise stack | M365 |
| Mobile/browser-first | Works but feels like a compromise | Purpose-built for web; native feel | |
| Adoption speed | Significant training investment | Near-zero learning curve for Gmail users | |
| Total cost of ownership | Higher complexity = higher real TCO including admin time | Lower complexity; less hidden cost |
The Honest Verdict: Which Businesses Should Choose Which
- You're in a regulated industry (healthcare, legal, financial, insurance) and need compliance tooling, audit logs, or sensitivity labels
- Your team does complex Excel or Word work that browser apps can't match
- You need device management (Intune) for company phones and laptops
- You're willing to fully configure the security features — deployed correctly, it's enterprise-grade protection at an accessible price
- You have or are getting an MSP to manage the tenant — the complexity pays off with expert administration
- Your team is 2–15 people with simple email, docs, and video call needs
- Staff already use Gmail personally and adoption speed matters
- You're on Chromebooks or mobile-first — Google's ecosystem is native
- No IT person internally and you need something manageable by a non-technical owner
- Budget is the primary constraint and compliance mandates don't apply
You're a 2–3 person solo-practice firm that needs email and nothing else — a standalone Exchange Online plan at $4/user/month or a cheaper email host may be the right answer. Paying $22/user for Business Premium and using only Outlook is poor ROI. Don't buy the suite you don't need.
What does "fully deployed" actually cost?
Be honest with yourself about total cost, not just license cost:
| Component | M365 Business Premium | Google Workspace Business Standard |
|---|---|---|
| Base license | $22.00/user/mo | $14.00/user/mo |
| Backup (third-party) | ~$3–6/user/mo | ~$3–5/user/mo |
| Admin/MSP (amortized) | ~$5–15/user/mo | ~$3–8/user/mo |
| Year 1 training | ~$2–5/user/mo | ~$1–2/user/mo |
| Realistic all-in Year 1 | ~$32–48/user/mo | ~$21–29/user/mo |
The gap is real, but so is the security delta at the premium tier. For a 15-person law firm, $22–$26/month difference per user in exchange for enterprise-grade EDR, device management, and Conditional Access is a reasonable trade. For a 5-person landscaping company, it isn't.
Before You Decide
The single most common mistake we see is businesses buying Business Standard when they should be on Premium — paying $12.50/user for the apps but missing all the security features — or buying Premium and never configuring Defender, Intune, or Conditional Access, which means they're paying $22 for a $12.50 plan with an unused security layer.
Microsoft 365 is a powerful platform. When it's sized right and fully deployed, it's worth the cost. When it's bought based on a sales pitch and left at default settings, it's an expensive email service with a false sense of security.
If you're unsure which tier fits your workflow — or you're on M365 already and want to know what security features are sitting unconfigured in your tenant — we're happy to take a look.