How to manage a hybrid cloud migration with employee training

You can move your technology to the cloud. But what about your people? For many organizations, this is where the real challenge lies. 

After all, cloud transformation doesn’t happen all at once. Some workloads move to the cloud while others remain on premises. This means organizations become responsible for managing identity, networking, security, data, and operations across both types of workloads. 

This creates a hybrid environment and a hybrid workforce of sorts. Some employees may have years of experience managing on-premises infrastructure. Others have deeper experience with cloud platforms, managed services, automation, and cloud-native ways of working.

A successful cloud transformation needs both kinds of expertise. And while most organizations have a plan for the technical side of cloud migrations, many lack a corresponding skill development strategy that helps people work across on-premises and cloud environments. Here’s how to build one.

Before you build an upskilling plan, understand the business and technology goals driving your cloud strategy. These goals should shape your approach to skill development.

This might include plans to:

• Migrate existing applications

• Modernize certain workloads 

• Improve disaster recovery

• Build new applications in the cloud while keeping important systems on-premises

• Reduce data center capacity 

• Standardize security and governance

Consider a team moving an internal application to the cloud while keeping its primary database and part of its identity infrastructure on-premises. In this scenario, the cloud specialists can deploy, secure, and monitor the application in the cloud. The infrastructure team can manage the existing network paths, authentication dependencies, firewall rules, database requirements, and operational history. But neither group can complete the transition successfully on its own.

The key is to combine their strengths through strong collaboration. Gather both groups and walk through a project on your organization’s roadmap. Ask each side what they need from each other to get it done.

Open dialogue can help you identify gaps before starting critical projects. It also helps teams build cloud skills relevant to real outcomes, not just general knowledge.

Next, look at the skills your team already has. Just because someone is new to cloud computing doesn’t mean they’re unfamiliar with the problems cloud solves. 

For example, an experienced network engineer already knows routing, connectivity, firewalls, DNS, and troubleshooting. A systems administrator brings expertise in operating systems, identity, patching, monitoring, and reliability. Security professionals bring experience with access controls, risk, governance, and incident response. 

The skills still matter, but how and where they’re applied may change. 

To get started, look at your team's capabilities as transferable skills, cloud-specific skills, and bridge skills.

Transferable skills are capabilities your people already have that remain valuable in a cloud or hybrid environment. 

Examples include: 

• Networking

• Identity

• Security

• Databases

• Operating systems

• Monitoring

• Resilience

• Troubleshooting

Consider a network engineer. They don’t need to relearn routing or segmentation. They just need to see how those concepts show up in the cloud or how their responsibilities might change.

When you identify transferable skills, experienced employees don’t need to relearn concepts they already know. You also make it clear that cloud transformation builds on existing expertise rather than replacing it.

Some capabilities are genuinely new. Your strategy may require people to learn: 

• Cloud service models

• Managed services

• Cloud governance

• Consumption-based cost models

• Automation

• Infrastructure as Code

• Containers

• Serverless computing

• New approaches to application deployment and operations

But not everyone needs the same level of expertise. An infrastructure specialist may need deep knowledge of cloud networking and only a working familiarity with serverless services. An application engineer may need the opposite. 

At the end of the day, you don’t want to turn everyone into the same kind of cloud professional. Instead, you want to help them develop expertise relevant to their specific roles.

Bridge skills are the capabilities that connect what happens on-premises with what happens in the cloud. This includes:

• Hybrid identity

• Connectivity between environments

• Workload migration

• Shared monitoring

• Security across infrastructure boundaries

• Data movement

• Troubleshooting applications with dependencies in multiple locations

These skills are easy to overlook because they don't belong neatly to one team. But they're critical to solving hybrid cloud problems. This may include scenarios like:

• An application is running normally in the cloud but users can't sign in because of an identity dependency

• A cloud service is healthy but an on-premises database is unreachable

• Monitoring shows a symptom in one environment even though the cause sits in another

After identifying the skills that matter, decide who needs to learn what. Some teams will benefit from specialists. Some will be fine with basic fluency. 

Everyone is working in the context of a larger environment. Cloud specialists should be familiar enough with the existing on-premises environment to recognize dependencies and constraints. On the flip side, on-premises specialists need enough cloud fluency to understand how services are deployed, secured, monitored, and operated. That shared knowledge leads to better decisions. 

Picture this: A cloud specialist and a network engineer design a solution together. Instead of treating an infrastructure dependency as unrelated to cloud migration, they can see how it affects the workload as a whole. It’s all about balance.

Unsurprisingly, shared knowledge develops faster when people interact with each other. For that reason, teams need opportunities to solve cross-environment problems together. 

You might set up a training scenario where employees can no longer access a business application that depends on identity and other services across both environments. Ask them:

• Which signals they would check

• How they would narrow down the origin of the issue

• What information each specialist needs from other people

• How they would coordinate the investigation

Other exercises can help teams develop bridge skills and improve their collaboration. You might task them with: 

• Maintaining consistent security policies across environments

• Planning disaster recovery for an on-premises workload using cloud resources

• Maintaining consistent architecture as teams introduce automation in the cloud while continuing to manage some on-premises systems 

Hybrid cloud skills aren't tied to one architecture, and these exercises help teams navigate across environmental boundaries.

Practicing in scenarios is one thing. Working together on real projects is another, and training alone won't close that gap. 

Take a look at your existing ticket routing, project ownership, architecture reviews, and incident response plans. If you make small changes to these processes, like changing who participates in a review, you can create more opportunities for teams to use their skills together.

You could also pair people with different backgrounds on migration projects. For example, bring on-premises infrastructure specialists into relevant cloud architecture reviews, and include cloud specialists in discussions about on-premises services that cloud applications depend on. 

Joint incident reviews can also help. Instead of focusing only on the team that owned a problem, examine how the issue moved across the environment, which signals were available, where the investigation slowed down, and what knowledge would have helped the team diagnose it faster.

The same principle applies to design work. If a new cloud application depends on an existing identity service, database, or network path, involve the people who know those systems before the architecture is finalized. The more your technology crosses boundaries, the more collaboration should, too.

When it comes to measuring the success of upskilling initiatives, it’s easy to count learning hours, completed courses, or assessment results. Those metrics can tell you if learning is happening, but not if it’s actually moving the needle.

To better understand the impact of upskilling, look at the work itself:

• Are fewer cross-environment incidents being escalated?

• Is the time required to diagnose hybrid incidents improving? 

• Can more employees follow a migration or recovery runbook without depending on one expert? 

• Are networking, identity, security, and cost issues being identified earlier during architecture reviews?

Specialist dependency is another useful signal. For example, if only one or two people can perform a critical process in your hybrid cloud and on-premises environment, that creates an operational risk. Increasing the number of people who can confidently handle that work is a significant outcome, even if their job titles haven't changed.

As your cloud roadmap and operating environment change, revisit these signals alongside your traditional upskilling metrics. The capabilities your team needs today may not be the same ones they need for the next migration, modernization project, or phase of hybrid operations.

Cloud transformation doesn’t mean your on-premises and cloud specialists learn the same things. Their unique expertise is valuable. 

But when you’re dealing with a cloud migration or new platforms, services, and ways of operating that cross the boundary between cloud and on-premises, your people need the skills to cross this boundary, too.

This is why upskilling is so important: It turns separate functions into one team that can operate in a hybrid cloud and on-premises environment together.