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Your climb to Cloud: Step 3 – Successfully manage the transition

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How to avoid the biggest pitfalls in your Cloud transformation

In our first article, we discussed best practices to be prepared for a Cloud transformation. In the second article, we shared the keys to a successful roadmap. Now, in this third installment, we look at some of the pitfalls you may encounter and how to steer clear of them.

Cloud transformation projects are filled with bumps and bruises and, as we’ve learned, the reality is that no project will ever finish flawlessly. What’s important is how to address challenges, because how you react and adapt will keep problems from stopping or derailing your project. Here are four pitfalls you may encounter in your Cloud migration and how to avoid them.

1. Not starting with the WHY in mind  

“Not recognizing the people and the milestones that contribute to the success of the project can be a dangerous pitfall.” Jeff Kays, Conduent Principal – Management Consulting

A Cloud move can be a truly transformational experience for an organization, but only if you have buy-in from all your stakeholders. These key participants, from many areas of the business, need to understand WHY you’re moving to the Cloud. Consider all the changes that will occur in this transformation: technology, processes, teams, roles and responsibilities, and even the company’s culture.

If they don’t understand WHY — the changes, the processes and the end state — chances are they won’t be as committed to the success of the project. Losing stakeholder support could have negative trickle-down effects including lost leadership support, limited access to subject matter experts and a lack of general organizational buy-in.

That’s why it’s so important for your many stakeholders to understand WHY you’re moving to the Cloud. And you need to share a compelling vision with those stakeholders to make it happen. To capture the hearts and minds of stakeholders, the vision has to be both analytically and emotionally compelling. Your WHY must demonstrate the quantitative and qualitative benefits at both the team level and the company level so that stakeholders act out of a desire for shared success rather than just obligation. Not doing so could be the difference between project success and a huge and embarrassing organizational stumble.

2. Aligning only the organization, not the individuals

Aligning people’s vision is more than simply prioritizing and publishing a roadmap and following a timeline. It also means there will be a new reality for individual employees. To be successful, your plan will need to account for the impact to your employees and understand their individual needs. Failing with your people is a pitfall that could result in culture issues, attrition and difficulty attracting new talent.

To meet your employees on their level, consider things from their perspective:

  • How will the work I do get better, faster and more engaging?
  • How will the change impact organizational structures — the people I work for and with?
  • How will the change impact my ability to grow my career and what I want to do in the future?
  • How will the change impact how I am supported, trained and enabled to do my work and be successful?
  • How will the change influence and impact what I value and how my performance is measured, recognized and rewarded?
  • How will the change influence my work balance, the work environment and how I access my work from a given location?
  • How will the change influence the company’s culture?

3. Ignoring the Roadmap

As we covered in our last article, your roadmap is an overview of your entire Cloud transformation. The roadmap is a necessary, living document that captures and demonstrates (at varying levels of detail) the mechanics of the project in a way that sets expectations and keeps management informed. While you don’t want the roadmap to change at the highest level, the details at the underlying levels will likely change as the project progresses, reflecting the unpredictability of a complex change initiative.

Many projects — even with the best preparation and intentions — fall into the trap of ignoring the changes that will inevitably occur. This corner-cutting creates holes in documentation and problems during implementation and beyond. For all projects, setting up the infrastructure and managing the timelines is the primary activity of the Project Management Office and associated governance. Identifying and mitigating risks and issues early and often, with the overall roadmap-to-value in mind, is critical to business case and project success.

4. Forgetting to identify and celebrate milestones

Speaking of success, a Cloud transformation project shouldn’t be all work and no play. Even though people are at the heart of any transformation, it’s easy to forget they’re more than just robots that are moving parts on the conveyor belt to completion. Not recognizing the people and the milestones that contribute to the success of the project can be a dangerous pitfall. It could impact the quality of outcomes, the satisfaction of impacted employees, the level of engagement and buy-in from Cloud tech users and, ultimately, the long-term value of the move to Cloud.

As a project sponsor, you need to be visible in celebrating the progress and make that celebration tangible for others. A good rule of thumb is: the bigger the change, the bigger the celebration. Consider spot bonuses, “good news” articles and industry events as ways to celebrate the success of the program and its implementation. And most importantly, don’t wait for the end to celebrate. By recognizing achievement along the way, you will help generate momentum, encourage the team and help the people doing the work adapt to a new, Cloud-enabled way of working.


Identifying and avoiding pitfalls in your Cloud transformation can keep your project on track and your organization engaged. Remember that you are not only changing technology but also fundamentally changing how many areas of your company will operate. Change is inevitable, and your roadmap is the key to smoothing out the rough patches you will encounter along the way. Just as important, people matter, whether they are stakeholders or employees affected by the transformation. Keeping these things in mind as you work through your move to the Cloud will have positive, lasting impacts in your end-state and beyond.

Editor’s note: This is the third of four posts from Jeff Kays about moving to the Cloud. More information about Conduent Cloud transformation consulting services can be found here