Cloud Migration in 2026: The 3 Critical Questions Every Business Leader Must Answer

Cloud migration used to primarily involve simple decisions such as, “Should we move our email to the cloud?” Today, cloud migrations are major business decisions tied to growing revenue, reducing risk, controlling costs, and staying competitive. Companies are actively and routinely leveraging the cloud to modernize IT systems with the goal of supporting everything from meeting regulatory requirements to creating better customer experiences.

No matter your industry, a cloud migration in 2026 requires thoughtful decisions from business leaders. To help your thinking, here are three questions every business leader should ask when considering the cloud.

1. Can my business operate smoothly if the internet goes down?

In the cloud era, remote work, cloud‑based phone systems, and real‑time collaboration tools (such as Microsoft Teams) rely on steady connectivity for smooth calls, meetings, and daily work. When the connection is unstable, productivity and service quality drop.

Unfortunately, while some areas of North America fare better than others, your business may operate in an area where a reliable internet connection is challenging. However, such a situation doesn’t mean you shouldn’t move to the cloud. It just means you need a plan for disruptions.

Whether your internet connection is strong or not, it’s best to:

• Use more than one internet provider. Redundant connections keep your business running during outages.
• Prevent “traffic congestion.” Ensure that high-bandwidth activities such as video calls don’t slow down your other cloud tools. Your IT resource can work to make sure that high-priority, high bandwidth activities get their own “lane” to ease congestion.
• Assess your office locations. By proactively testing the internet connections at your various office locations, you can see if you have enough speed and stability to support cloud tools. 

2. How much will the cloud really cost me?

 A decade ago, the cloud was widely marketed as cheaper. Today, the truth is more nuanced depending on usage, configuration, business growth, and ongoing IT discipline. Some issues include:  

• Consumption-based pricing: Cloud services charge based on how much you use, which sounds efficient but can become unpredictable without strong oversight. As more users log in, more applications run in the background, and more data gets stored or processed, costs can scale rapidly. 

• Subscription creep: The cloud makes it easy to add users and services, but licenses often remain active long after employees or teams stop using them.

• Data transfer fees: While cloud storage is relatively cheap, moving data out of the cloud (known as an egress fee) can be unexpectedly expensive. You may pay these fees when you back up large datasets, transfer data (to a partner, vendor, or client), or run analytics.

• Underutilized resources: Cloud platforms make it easy to spin up servers, storage, and databases, but it’s just as easy to forget about them. Over‑provisioning and “zombie resources” (systems running without purpose) are major contributors to runaway cloud bills. 

   

As a result, a growing number of organizations are moving some workloads back to on‑premises to better control costs. They aren’t abandoning the cloud but rebalancing it.

The cloud is not automatically cheaper or more expensive. It’s all about fit. When evaluating whether the cloud makes financial sense, it’s important to look beyond subscription costs and take a holistic view of both operational and capital expenses.

• Treat the financial management of your cloud resources as an ongoing discipline and not just as a one‑time estimate. Cloud costs change as usage changes, so your financial team should forecast, monitor, and review cloud spending with the same rigor as any major investment.

• Evaluate each system individually while factoring in your on-premises refresh cycle. Some workloads run more efficiently in the cloud while others may remain more cost-effective on your own hardware. For example, if replacing a physical server costs $15,000 every five years, that’s a known cost you can model. Contrast this cycle of ownership with the cloud’s ongoing operational fees.  

• Plan for business growth and not just today’s needs. AI adoption, rising data volumes, larger file storage, and new cloud applications can increase cloud usage (and costs) over time. Anticipate these future growth factors so you aren’t surprised by unexpected cost increases. 

3. How will I protect my data and stay compliant in the cloud?

Two of the biggest worries for businesses about the cloud are cybersecurity and compliance. Naturally, business leaders have many questions about these non‑negotiable areas when thinking about cloud migrations, especially when you handle sensitive information.

Cyberattackers go after cloud targets just as easily as on-premises targets. While cloud vendors generally do an amazing job keeping their data centers secure, those data centers are not usually where cyberattackers find weaknesses.

• Human error is responsible for 55% of cloud data breaches.

• Misconfigurations—businesses accidentally configuring something incorrectly—are one of the leading causes of cloud breaches.

• Cyberattackers can steal cloud access credentials with the same tactics and techniques they use to steal email or administrative credentials.

• Misunderstanding the shared responsibility model is a major contributor to breaches. Cloud providers secure the infrastructure of the cloud, while businesses must secure what they configure in the cloud (such as identity, access, data protection, and settings). 

One of the biggest cybersecurity issues that can catch a business off guard is when a ransomware attack affects cloud backups. The assumption that “the cloud protects us from ransomware” is outdated because cyberattackers now explicitly target cloud environments. Unless your backups are “immutable” (meaning they are completely separated from your network and unable to be modified, deleted, or overwritten), they are susceptible to a ransomware attack. 

Obviously, these cybersecurity issues also affect compliance. A vendor saying “our platform is compliant” does not mean your implementation is compliant—where you have responsibility for continuous visibility, documentation, and proof of controls. Cloud environments expand your attack surface and introduce new risks. Remember, you must produce evidence of security control effectiveness to auditors—not the vendor.  

So…is moving to the cloud the right choice in 2026?

For most organizations, the answer is yes…if done strategically. The cloud can help your business with scalability, offer better collaboration tools (especially for remote workers), and accelerate innovation. But business leaders must navigate cost management, connectivity issues, and cybersecurity risks thoughtfully.

If you’re evaluating cloud options, take the following steps:

1. Assess your business needs, not just your technology. This will help ensure that your investments are aligned to goals and objectives.
2. Identify any internet and bandwidth issues that could limit the effectiveness of using the cloud.
3. Model cloud costs including taking future growth into account.
4. Review your security, compliance, and data backup strategies. Don’t assume the cloud vendor is taking care of all these needs. (An IT professional can help you independently assess your gaps and risks.)
5. Create a phased migration plan that prioritizes your highest‑value systems first.
6. Engage a trusted partner who understands both your business needs and technical requirements.

Common Questions about Cloud Migrations for Businesses

Is the cloud actually more secure than on‑premises IT?

It can be, but only when configurations, access controls, and backups are properly managed.

How long does a cloud migration usually take?

Timelines vary based on your system complexity, but most organizations phase cloud migrations over months, not weeks.

What are the biggest hidden costs of cloud migration?

Ongoing usage fees (such as storage, data transfer, and compute time) and subscription creep.

How do I know which systems should move to the cloud first?

Start with high‑value, high‑impact systems or on-premises systems nearing end of life or lifecycle refresh.

All of my applications are currently cloud-based. Do I need to consider a cloud strategy, or am I good?

Even if all your applications are cloud‑based, you still need a cloud strategy that ensures you’re managing costs, performance, cybersecurity, compliance, data protection, and long‑term scalability.

TL;DR

Cloud migration in 2026 is no longer a simple IT upgrade—it’s a strategic business decision tied to cost control, operational resilience, cybersecurity, and compliance. To make the right choices, leaders should evaluate whether their internet connectivity can support cloud‑based operations, what the cloud will truly cost over time, and how they will protect data and meet compliance requirements in a cloud environment. With proper planning, cloud adoption can enhance productivity, scalability, and security—but only when organizations assess their risks, model long‑term costs, review their cyber and compliance posture, and partner with experts who understand both business and technical needs.