Five tips to avoid cloud migration failure

How to gain employee buy-in and set realistic stakeholder expectations

Mike Ryan, Managing Principal Consultant; Robin Morrison, Head of Cloud Solution Offerings


12 Jun 2023

Five tips to avoid cloud migration failure

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Cloud migrations often pose daunting technical challenges, but the work doesn’t end there.

A lack of focus on organizational and political considerations can lead to suboptimal outcomes or worse, outright failure. Here are five factors that you need to keep in mind:

  1. Gain momentum by addressing others’ viewpoints upfront
  2. Paint and communicate a vision for the future
  3. Proactively manage business stakeholders’ expectations
  4. Integrate DevSecOps into your structure
  5. Adopt agile now, before cloud migration

We work with company leaders who are eager to forge ahead in the cloud. However, some decisions can cause a cloud migration to fail before it ever gets off the ground. In this blog post, we expand on the above tips to help ensure your cloud migration takes off.

Tip one: Gain momentum by addressing others’ viewpoints upfront

First off, it’s important to understand that not everyone is as excited as you about adopting cloud. For technology leaders, moving to the cloud means a bright future where enhanced organizational agility and superior quality let you win in the marketplace, free up money for new investments, and attract the best engineers in today’s tough labor market. Unfortunately, not everyone will share this vision or enthusiasm. Many will worry about change to their day-to-day jobs or a lack of skills and knowledge to handle what’s coming. Some will fear for their jobs and be tempted to slow walk or even sabotage your efforts. Cloud journeys inevitably transform employee experience across the board, promising a radically different work environment for testers, developers, and managers. This can be jarring.

You can help your vision become reality by having and communicating empathy for employees, finance leaders and other stakeholders. Take the time to understand their concerns so that you can address them upfront and sincerely.

  • Communicate early and often about training programs for all affected roles.
  • Emphasize that cloud technologies often result in better application performance and almost no downtime, which means no late nights or weekend work trying to bring up systems that have crashed.
  • Stress how learning new technologies makes employees more valuable in the marketplace.

Tip two: Paint and communicate a vision for the future

For your vision to become reality, you first must communicate it. Explain your cloud vision widely and often. Convey it in a way that helps everyone see how they can help to achieve, and benefit from, the cloud journey.

  • Describe how managing a public cloud rather than a virtualized datacenter changes day-to-day work for employees, positioning it as something exciting for them and their careers.
  • Talk about new roles that will be needed, like SREs (Site Reliability Engineers).
  • Ensure the cloud journey plan includes skill and role development training and share widely that skills training is part of the cloud journey plan.

It’s crucial to back your vision up with concrete plans. Be armed with case studies and testimonials from engineers at other companies about how cloud migration has helped them learn new skills and improve their day-to-day work life. Honestly assess your team’s current skill sets and lay out a detailed learning path for them. Identify the most tedious parts of their current workday and then show how cloud technology can eliminate them.

After these detailed training plans are developed, communicate them in multiple places. Discuss training plans in all-hands meetings, and guide managers on how to communicate details in smaller team meetings and one-on-ones. Be sure to address how managers and employees can sign up for and participate in training to make this feel real for everyone.

Tip three: Proactively manage business stakeholders’ expectations

In their excitement, company leadership can sometimes exaggerate expectations of a fast return on investment. The cloud transformation may even have been sold to senior management as a ‘quick win’ with little risk and massive financial gain. Everyone assumes there will be radical savings in going to the cloud. Public cloud providers themselves emphasize savings in their marketing materials. You can and should save costs, but to do so you must implement cloud computing best practices across the business.

Ensure your transformation goes the distance by outlining the true scope of additional change and work required to business stakeholders. Also explain that there are many more benefits to a cloud migration than just saving money. The ability to rapidly pivot to meet changing customer demands, improved quality and uptime of existing workloads, the financial benefits of operating expenses vs capital expenses, and the opportunity to recruit top technical talent are all widely experienced benefits of cloud migrations.

  • Help VPs and business owners understand that simply moving workloads to the cloud will not automatically save money or improve velocity. Changes in architecture and engineering practices will likely be required to achieve the full benefits.
  • Help business stakeholders understand the difference between the various paths to cloud:
    • Rehost means doing a ‘lift and shift’ now and modernizing later. This strategy may result in minimal savings, or no savings at all, because existing applications aren’t architected to truly take advantage of the cloud. Lift and shift efforts are best used as a precursor for future migration efforts. Read this blog to learn 3 situations where a lift and shift is right, and 3 where it isn’t.
    • Re-factor / Re-architect means redesigning the architecture and code to build a cloud-native application. With this approach, you essentially rewrite all or part of your application. An example would be moving from a monolithic application to a microservices architecture that can more easily take advantage of the cloud.
    • Re-platform (sometimes referred to as ‘lift, tinker, and shift’) means moving from on-premises to cloud with only modest enhancements to the application. These enhancements can include things like making specific pieces of your application more horizontally scalable.

Some types of workloads provide more opportunities for savings than others. Cloud lets you increase capacity to meet times of peak demand and then scale down when demand lessens. This is where cost savings can be found. If a workload experiences constant load, there are fewer opportunities for savings.

Successfully scaling up and down to meet fluctuating demand often requires changes to an application’s architecture. We typically find that a microservice architecture is appropriate in these circumstances.

Tip four: Integrate DevSecOps into your engineering processes

Enable teams to move faster in the cloud by building and integrating DevSecOps into your cloud pipeline. DevSecOps is not a role. Rather, it is a set of practices built on a philosophy of integrating security practices within the DevOps process itself. ‘Zero trust’ security principles are a highly recommended offshoot of DevSecOps.

  • Proof of Concepts are important both technically and organizationally. You’ll need an initial team who understands the cloud to develop best practices and implement a good pipeline. Make sure each successive round of teams who join the migration know how to leverage it.
  • Implement DevOps processes by organizing your teams in such a way that testing and deployment can be fully automated. Engineering time spent on wonky, one-off, manual processes is time taken away from developing new features, infrastructure, and automations. This sort of work is demotivating and frustrating for engineers.
  • With investment in DevSecOps practices and pipelines, the organization can quickly respond to customer demand by rapidly and securely making changes to the infrastructure and applications.
  • Just as important as financial and competitive considerations is the ability to recruit top technical talent. Most technology professionals want to work in the cloud! These skills are relevant to building their career. Offering work on cloud-native applications is a big recruiting tool if you want to attract top talent to your company.

Tip five: Adopt agile now, before cloud migration

If you’re not already agile, start here! Migrating to the cloud is more than simply moving a datacenter to another location. You will not be able to exploit the ability to deploy faster and improve time to market without also adopting an agile workflow. Also, keep in mind that agile methodologies require training, new processes, and transparency into work. These may create as much uncertainty for employees as the cloud itself.

Migrations benefit from having a solid and detailed plan, and most follow a similar path. But in our experience, migration programs also benefit from scrum and other agile methods. Cloud migrations have similar complexities to new software development, where seemingly simple applications become more complex, dependencies need to be managed, and close collaboration with business owners and end users is necessary. Most migrations experience frequent pivots and changes to the original plan. Constant focus on continuous improvement and supporting teams by removing impediments is as valuable to cloud migrations as it is to new software development.

You don’t have to learn through trial and error

There’s no need to reinvent the cloud journey for your own company. A trusted cloud consultant can help guide you through the myriad people and process considerations. Having an experienced consultant on the journey will help you gain the most from your cloud investment and ensure you have the organizational readiness to capitalize on your newfound agility and scalability.

Learn more about our cloud migration services.


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