Why Choose It, Which Plan to Buy, and How to Migrate Email Smoothly
If you’re running a small business, your “office suite” isn’t just Word and Excel—it’s your email, calendar, files, meetings, and how your team actually gets work done. Microsoft 365 (formerly Office 365—sometimes people say “Office 360”) is still the default choice for a lot of organizations for one simple reason: it’s the most universally compatible stack for documents + business email.
Below is a practical guide to (1) why you might pick Microsoft 365 over alternatives, (2) how to choose the right plan and what it costs per user, and (3) what it takes to move email from something like Google Workspace—DNS and all—with help from Chesley Software.
Why prefer Microsoft 365 over alternatives?
Here are the common “real world” reasons we see clients choose Microsoft 365:
- Best-in-class compatibility with Word/Excel files
If you exchange documents with clients, accountants, banks, attorneys, or government agencies, Microsoft formats are the lingua franca. You’ll spend less time fixing formatting drift. - Outlook + Exchange for business email
Many organizations specifically want Exchange-hosted mailboxes and Outlook workflows (shared calendars, delegation, scheduling, etc.). Microsoft 365 business plans include “custom business email” (you@yourbusiness.com) with Exchange on most tiers. (microsoft.com) - Desktop apps when you need them (not just web apps)
Some teams truly need the installed versions of Excel/Word/PowerPoint/Outlook for advanced features, offline work, or performance. (Not all plans include desktop apps—more on that below.) (microsoft.com) - Integrated collaboration (Teams, SharePoint, OneDrive)
One subscription can cover meetings/chat plus file storage and sharing in a way that’s consistent across devices. (microsoft.com) - Security and device management when you’re ready to level up
If you want stronger protection (phishing/ransomware defenses, endpoint protection, device controls), Microsoft 365 Business Premium adds enterprise-grade security and management capabilities like Intune and Defender features. (microsoft.com)
How to choose the right Microsoft 365 plan (and what it costs per user)
Microsoft’s small-business plans are typically licensed per user, and most business plans are aimed at organizations up to 300 users. (microsoft.com)
Quick “which plan is right?” cheat sheet
- Microsoft 365 Business Basic → Best when you want business email + Teams + web/mobile Office apps (and don’t need the desktop apps). Includes custom business email and 1 TB OneDrive storage per user. (microsoft.com)
- Microsoft 365 Apps for business → Best when you want the desktop Office apps + 1 TB storage, but you already have email elsewhere (or don’t need Exchange). (microsoft.com)
- Microsoft 365 Business Standard → Best “most common” choice: desktop Office apps + business email + Teams. (microsoft.com)
- Microsoft 365 Business Premium → Best for organizations that want Business Standard + advanced security/device management (Intune/Defender-style protections). (microsoft.com)
Current pricing (US list pricing shown by Microsoft)
As of February 2026, Microsoft lists these per-user prices on its plan pages (annual commitment vs month-to-month):
| Plan | Best for | Price (annual commitment) | Price (month-to-month) |
|---|---|---|---|
| Microsoft 365 Business Basic | Email + Teams + web/mobile apps | $6.00/user/mo | $7.20/user/mo |
| Microsoft 365 Apps for business | Desktop apps + storage (no hosted email) | $8.25/user/mo | $9.90/user/mo |
| Microsoft 365 Business Standard | Desktop apps + hosted email + Teams | $12.50/user/mo | $15.00/user/mo |
| Microsoft 365 Business Premium | Standard + stronger security/device mgmt | $22.00/user/mo | $26.40/user/mo |
Source: Microsoft plan pages for Business Basic, Apps for business, Business Standard, and Business Premium. (microsoft.com)
Note: Microsoft also shows “no Teams” variants in some markets. If Teams is important for you, confirm you’re buying the right SKU for your region. (microsoft.com)
Email setup: DNS configuration essentials
When you move email to Microsoft 365 (Exchange Online), DNS is the steering wheel. The exact record values vary by tenant, but the building blocks are consistent:
The “must do” records for Exchange Online mail flow
- Domain verification TXT (Microsoft 365 admin center provides the value)
- MX record pointing to your tenant’s Microsoft protection hostname (
<MX-token>.mail.protection.outlook.com) (Microsoft Learn) - SPF TXT record (often starts with
v=spf1 include:spf.protection.outlook.com ...) and must be combined with any existing SPF senders (Mailchimp, website forms, CRMs, etc.) (Microsoft Learn) - Autodiscover CNAME (helps Outlook/mobile clients find settings automatically) (Microsoft Learn)
Strongly recommended email authentication
- DKIM (Microsoft provides two CNAME records when you enable DKIM for the domain)
- DMARC (TXT record that tells receivers how to handle messages that fail SPF/DKIM)
Microsoft’s DNS guidance and record requirements are documented in their domain/DNS setup resources. (Microsoft Learn)
How Chesley Software helps: we’ll review your current DNS (and any existing email services), design a cutover plan that avoids downtime, and implement the records in your DNS host (GoDaddy, Cloudflare, Namecheap, etc.), including SPF “merge” work so you don’t accidentally break outbound sending.
Migrating existing mail (example: Google Workspace → Microsoft 365)
Most businesses don’t just want “new mail going forward”—they want historical email, and often contacts + calendars too.
Microsoft supports an automated batch migration approach through the Exchange admin center that can migrate email, contacts, and calendars from Google Workspace. (Microsoft Learn)
A typical migration approach (minimizing disruption)
- Pre-migration assessment
- Users, aliases, groups/shared mailboxes
- How people access mail today (Gmail web, Outlook, Apple Mail, phones)
- Compliance/retention needs
- Set up Microsoft 365
- Create tenant, add users, assign licenses
- Verify your domain (TXT record)
- Prepare Google Workspace for migration
- Configure access/permissions required by the migration method (Microsoft documents both automated and manual paths). (Microsoft Learn)
- Run batch migrations
- Start syncing mailbox data before the cutover (staged approach)
- Validate sample users first, then migrate in waves
- Cutover (DNS switch)
- Change MX to Microsoft 365 so new inbound mail lands in Exchange Online (Microsoft Learn)
- Keep a short “watch window” for stragglers and forwarding rules if needed
- Post-cutover cleanup
- Ensure Outlook profiles and mobile devices connect cleanly (Autodiscover)
- Turn on DKIM/DMARC, confirm SPF alignment
- Confirm shared resources and calendaring behavior
Microsoft notes you can migrate in batches/stages, which is especially helpful if you want to reduce risk and keep the business running during the transition. (Microsoft Learn)
How Chesley Software helps: We manage the project end-to-end—tenant setup, licensing guidance, DNS updates, migration execution, and the “last mile” support (Outlook setup, mobile mail, shared calendars) so your team doesn’t lose time fighting configuration issues.
Want Chesley Software to scope your Microsoft 365 move?
If you tell us:
- number of users
- whether you need desktop apps
- whether you want to migrate calendars/contacts (or email only)
- your current email platform (Google Workspace, IMAP host, etc.)
…we can recommend the best-fit plan and outline a clean migration plan with minimal downtime—plus handle the DNS and migration execution for you.
