Avoiding Cloud Migration Pitfalls:

Why Projects Fail and How to Succeed

Many cloud projects focus too much on technology and not enough on transformation. It’s not just about swapping one system for another—it’s about reimagining workflows, improving user experience, and driving internal adoption.

How to Succeed: Treat cloud migration as a business transformation, not an IT upgrade. Engage end users, redesign processes, and focus on outcomes—not just technology. Get user input along the way, engaging employees in the transformation and getting customers ready to adopt a new look and feel. This is also a way to keep your employees engaged in the future strategy of your company and feeling a part of their workplace.

Without leadership support, cloud projects lose momentum. When executives aren’t involved, adoption lags, and the project risks becoming a sunk cost.

How to Succeed: Secure executive sponsorship from the start. Show leadership how the cloud aligns with business objectives and keep them engaged throughout the process. Schedule and keep regular leadership check-ins, even when the project stalls. Partnering with a tech strategist is a great way to make this a reality as they can be instrumental in creating a plan for your leadership team.

Many assume employees will just ‘figure it out.’ The reality? 85% of users need training and support to adopt new systems effectively.

How to Succeed: Plan for training within change management framework from the outset. Provide training events, anticipate resistance, and give teams the support they need to embrace new workflows. (link to case study for Riordan when ready with a sentence about discovering what one of clients did).

Cloud projects aren’t ‘set it and forget it.’ Customers who assume the vendor handles everything often find their needs aren’t met. Vendors work in their silos; tech strategists see the larger picture. The benefit of going to the cloud is the flexibility of connecting systems to maximize business efficiency.

How to Succeed: Work with a tech strategist who can bridge the gap between business goals and technology implementation. Also, assign an internal project manager to oversee the rollout, ensure all business units are engaged, and work closely with your tech strategist. This one-two punch creates a dynamic duo in creating an alignment between the two organizations.

A single email announcing a new system won’t lead to a successful implementation. People need to hear a message multiple times before it sinks in.

How to Succeed: Create a schedule of planned emails, videos, chats, and live sessions to foster a sense of community and, more importantly, transformation. This approach not only keeps users informed but also provides necessary training and gathers critical feedback to optimize system adoption.

Just because the system is live doesn’t mean the project is over. User adoption, ongoing optimization, and feedback loops are crucial.

How to Succeed: Monitor adoption by tracking usage metrics and gathering input from different user groups. Conduct regular check-ins and surveys to identify pain points and areas for improvement. Use this feedback to refine workflows, enhance system functionality, and ensure long-term success. A proactive approach to continuous improvement will maximize the value of your cloud investment.

Unexpected costs like misaligned licenses, duplicate services, and unplanned contract fees can derail cloud projects.

How to Succeed: Partnering with a tech strategist helps align costs by conducting a thorough needs analysis alongside an experienced solutions architect. This ensures the right licenses are purchased, unnecessary costs are avoided, and the total cost of ownership is clearly understood before implementation. By taking a strategic approach to budgeting, businesses can prevent financial surprises and optimize their cloud investments. Remember the best part of a tech strategist is they are free and don’t have a line item on your budget!

No documentation means no roadmap for troubleshooting, scaling, or optimizing the system.

How to Succeed: Remember that internal project manager? Here is where they can make the biggest difference by structuring a document flow from vendor to customer. They will be able to help maintain comprehensive documentation, from network diagrams to user workflows, ensuring smooth operations and future improvements.

Even the best-laid plans can go awry due to simple human errors. Database errors, porting mistakes, and spreadsheet miscalculations can derail cloud projects, causing costly delays and frustration.

How to Succeed: Implement strong quality control processes, including multiple layers of review and testing with an IT advisor before final implementation. Leverage automation where possible to reduce manual input errors, and ensure teams are trained to recognize and mitigate potential mistakes early in the process.

One of the biggest reasons cloud projects fail is because they never get started at all. Technology procurement is harder than ever, with more tools, more marketing fluff, and more uncertainty about making the right decision. The fear of change and doubt about choosing the best solution often leads businesses to stick with the status quo rather than moving forward with transformation.

How to Succeed: Work with a tech strategist to cut through the noise and develop a clear, confident strategy for cloud migration. A tech strategist helps businesses assess options, understand true capabilities versus marketing hype, and create a roadmap that ensures long-term success. Don’t let indecision hold your business back—take a proactive step toward innovation with expert guidance.