"We should move to the cloud."
It's one of those phrases that gets tossed around in business meetings like everyone agrees on what it means. But when you dig in, the picture gets fuzzy fast. What exactly are we moving? Where is it going? How much will it cost? And what happens to our stuff during the transition?
If you're running a small or medium business and wondering whether cloud migration makes sense, you're asking the right question. The answer isn't always yes — but when it is, doing it right can transform how your business operates.
Here's how to think through it.
What "moving to the cloud" actually means
Let's cut through the jargon.
"The cloud" just means someone else's computers. Instead of running software on a server in your office closet or on individual machines, you're running it on servers owned by Microsoft, Google, Amazon, or another provider — accessed over the internet.
Cloud migration is the process of moving your data, applications, or infrastructure from local systems to these hosted environments.
This can mean different things depending on your situation:
Moving files and documents — From a local file server to Google Drive, Dropbox, or SharePoint.
Moving email — From an on-premise Exchange server to Microsoft 365 or Google Workspace.
Moving applications — From software installed on a local server to cloud-hosted versions (like QuickBooks Desktop to QuickBooks).
Moving custom systems — From servers you own to cloud infrastructure like AWS, Azure, or Google Cloud.
Most small businesses aren't doing that last one. If you're running a 20-person company, "cloud migration" probably means moving from local file storage and on-premise email to something like Microsoft 365 — not spinning up virtual machines on AWS.
The real benefits (not the marketing hype)
Cloud providers love to promise the world. Here's what actually matters for most small businesses:
Access from anywhere. Your team can work from the office, home, a coffee shop, or an airport. No VPN headaches. No "I left that file on my work computer." This isn't a nice-to-have anymore — it's how people expect to work.
Someone else handles maintenance. No more server updates at midnight. No hardware failures to troubleshoot. No "the IT guy is on vacation and the email server crashed." The provider handles uptime, security patches, and backups.
Predictable costs. Instead of big capital expenditures for hardware every few years, you pay monthly per user. Easier to budget, easier to scale up or down.
Better collaboration. Real-time document editing. Shared calendars that actually work. Integrations and automation between tools. Cloud-native software is built for teams working together.
Automatic backups and disaster recovery. Your data isn't sitting on a single hard drive that could fail tomorrow. Cloud providers replicate data across multiple locations. If their data center has a problem, you probably won't even notice.
When cloud migration makes sense
Not every business needs to rush to the cloud. But these are strong signals that it's time:
Your team works remotely — even sometimes. If people are emailing files to themselves, using personal Dropbox accounts, or complaining about VPN connections, you've already outgrown your local setup.
Your hardware is aging. Servers typically last 5-7 years. If yours is approaching end-of-life, you're facing a choice: buy new hardware or migrate to the cloud. The cloud often wins on total cost.
You're worried about data loss. If your backup strategy involves a USB drive or "we should really set that up," you're one hardware failure away from disaster. Cloud providers handle this automatically.
You're paying for IT firefighting. If your IT support spends more time keeping old systems running than helping you move forward, that's a sign your infrastructure is holding you back.
You want to use modern tools. Many of the best business applications today are cloud-only. If you're stuck on old versions of software because your infrastructure can't support the new ones, migration opens doors.
When to think twice
Cloud isn't always the answer:
Extremely sensitive data with strict compliance requirements. Some industries have regulations that make cloud complicated — though not impossible. Healthcare, finance, and government contractors need to be thoughtful about which cloud services they use and how they're configured.
Unreliable internet. Cloud-dependent workflows need solid connectivity. If your location has frequent outages or slow speeds, you'll need to solve that first — or plan for offline scenarios.
Massive data volumes. If you're working with terabytes of video files or scientific data, the economics might favor local storage. Moving huge amounts of data to and from the cloud can be slow and expensive.
Systems that just work. If you have a stable, well-maintained on-premise setup that meets your needs, migration for its own sake isn't worth the disruption. "If it ain't broke" is a valid argument — sometimes.
How to approach it
If migration makes sense, here's how to do it without chaos:
Start with a clear inventory. What systems are you actually using? Where does your data live? What applications depend on what infrastructure? You can't plan a move if you don't know what you're moving. This is exactly what a technology roadmap helps you figure out.
Prioritize by pain and risk. You don't have to migrate everything at once. Start with the systems causing the most problems or posing the most risk. Email and file storage are often good first moves — high impact, relatively straightforward.
Pick the right destination. Microsoft 365 and Google Workspace are the two big players for small business productivity. Microsoft tends to win if you're already a Windows/Office shop. Google often wins on simplicity and price. Either works. This is similar to build vs buy decisions — the best choice depends on your specific situation.
Plan the transition carefully. How will data move? What's the cutover plan? How do you handle the period where some things are migrated and some aren't? What training do people need? These details matter more than which cloud you pick.
Test before you go all-in. Pilot with a small group first. Find the problems before you've migrated everyone.
Don't forget the humans. Technology migration is also a change management project. People need to understand why you're doing this, how it affects them, and where to get help when they're confused.
What it typically costs
For a straightforward small business migration (email, files, basic productivity apps):
Microsoft 365 or Google Workspace: $12-20 per user per month for business tiers with adequate storage and features.
Migration services: $500-5,000+ depending on complexity, data volume, and how much cleanup is needed. Simple moves can be DIY; complex environments with legacy data need professional help.
Training and change management: Often overlooked, rarely free. Budget time even if you don't hire outside help.
Ongoing: The subscription becomes your new normal. But you're also eliminating server hardware costs, maintenance, and a lot of IT headaches.
Compare that to a new on-premise server ($5-15K hardware, plus setup, plus ongoing maintenance) and cloud often wins — especially when you factor in the risk and hassle you're offloading.
How we help
At DGK Technologies, cloud migrations are one of our core services.
We start by understanding what you have and what's actually causing problems. Sometimes the answer is a full migration. Sometimes it's a partial move. Sometimes it's "your current setup is fine, just needs some cleanup."
When migration is the right call, we handle the planning, execution, and transition support — including the parts most providers skip, like data cleanup, permission structures, and making sure your team actually knows how to use the new tools.
We scope it properly upfront so there are no surprises. And we stick around to make sure everything actually works, not just that the boxes got checked.