9-minute read
Quick summary: Learn how to build a tailored Agile transformation roadmap that drives sustainable growth and adaptability across your organization.
Agile transformation is a powerful journey—one that’s also fraught with challenges. Organizations turn to Agile not just for faster software delivery, but also to foster a culture of flexibility, adaptability, and efficiency across the board. A successful Agile transformation is a deep shift in how a company operates, requiring structural and cultural changes that support ongoing improvement.
In this article, we’ll explore what Agile transformation truly is, why it’s more than just adopting frameworks, and how a tailored Agile transformation roadmap can assist and guide your journey. We’ll cover the essential steps, cultural shifts, and strategies for scaling Agile practices and sustaining progress over time.
What is Agile transformation?
Agile transformation is a comprehensive process that involves shifting an organization to Agile ways of working, which is not always easy. Transformation is not just about adopting Agile software development methodologies such as Scrum or Lean. It is a complete overhaul of the organization’s culture, processes, and structure to embrace agility, adaptability, and efficiency.
Every transformation is different; this is not a one-size-fits-all kind of process. You will need to review your business practices, culture, maturity levels, and processes long before you start implementing the transformation plan.
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Key benefits of an Agile transformation roadmap
An Agile transformation roadmap acts as a structured guide, breaks down the transformation into manageable phases, and ensures everyone understands their roles and responsibilities during the process. It helps with high-level planning, aligning stakeholders, securing resources, and creating a roadmap to achieve the desired future state of the Agile transformation. The clarity it imparts can help encourage buy-in from leadership and team members. Further benefits of having a roadmap include a clear vision of success, improved collaboration, and prioritization of essential aspects.
Every transformation is unique; this is not a one-size-fits-all kind of process.
Prerequisites for a successful Agile transformation
First things first: Is Agile transformation right for your situation? Many believe it’s a “one and done” kind of process; however, I am here to say it is not. It is a journey, and sometimes it’s costly in ways leaders may not understand if they have not done this kind of work previously.
One of the biggest reasons Agile transformations fail is that the organization’s management and leadership don’t understand what it takes. Many don’t comprehend they must give up their command-and-control mindsets to make it work.
Do your company’s strategies align with Agile? If not, you may have to make some significant realignments to support the change.
Often when people hear “Hey, you have to change,” there is significant resistance to the process. Therefore, your approach will have an enormous impact on the outcome of your Agile transformation.
Many companies also assign people to work for many different teams to save costs. Agile requires persistent teams that don’t change—or at least don’t change often—so additional people may be needed to make the teams work.
And finally, if your culture is already broken, don’t expect Agile to miraculously change it. You will need to overhaul your culture, building trust and transparency, if you expect to gain buy-in from your workforce and reap the benefits of Agile transformation.
Building an Agile transformation roadmap
Building an Agile transformation roadmap is a critically important step in a successful journey. The roadmap should include as many steps along the way as you can plan for, knowing that if your organization is truly going to be Agile, changes and updates along the way may be needed.
Building out an Agile transformation roadmap begins with a review of nearly everything the company or organization is doing, to determine what needs updating. You may find practices and processes in place that don’t require change.
For example, in a recent Agile transformation, one of the teams we met with was already using Agile principles and delivering on a regular cadence. That team was the reason the CEO wanted to pursue a full transformation and thus didn’t need many changes. Only when it came to the group planning—which they had not been doing since none of the rest of the organization was Agile—did they need any assistance and training.
The Agile transformation roadmap should include as many steps along the way as you can plan for, knowing that if your organization is truly going to be Agile, changes and updates along the way may be needed.
Adopting an Agile culture
Before even starting to think about an Agile transformation roadmap, consider your culture. If it needs help, this is the place to start. Do you have toxic team members? Do you have inexperienced leadership at any level? People must be ready for the transformation before “liftoff.”
Here are some of the steps we recommend for creating an Agile transformation roadmap:
Assess current organizational maturity
An Agile maturity model is a framework that helps organizations assess their proficiency in Agile practices. By evaluating key areas such as team collaboration, adaptability, and process efficiency, the model identifies strengths and areas for improvement, guiding organizations as they advance in their Agile transformation journey. There are many maturity models available, and each has its own merits. When we work with clients, we direct them to the model that works best for their organization.
As mentioned above, organizations must take an honest look at what they have in place already before they start making any changes. Understanding their maturity level is a key step. There are many ways to do these measurements, but often I recommend a team-by-team assessment, including all the leadership teams as well. This is a great place to start.
If leadership teams are mature enough on the scale, you can then start planning, but until they reach a reasonable maturity level, you need to slow down.
Leaders must be able to work together effectively. I have seen many companies where leadership took more time and effort than non-management employees in getting up to speed and trained in Agile ways of working.
This is a crucial step that is often missed or ignored. If leadership isn’t on board with the process, failure of the Agile transformation program is almost guaranteed.
This is also one of the most challenging parts of the transformation. Leaders are usually short on time, so they rarely get to sit with their teams as decisions are being made. This new way of doing business, based on decentralized decision making, can feel like they are losing or giving up control. This can feel extremely uncomfortable if they are used to calling the shots.
Powerful Agile leaders can make a huge difference in your transformation.
By evaluating key areas such as team collaboration, adaptability, and process efficiency, the maturity model identifies strengths and areas for improvement, guiding organizations as they advance in their Agile transformation journey.
Define your vision and purpose
Without a sharp vision of the destination of your Agile transformation roadmap and the purposes for pursuing it, you may not end up where you want to go. This disconnect also falls to leadership, and it can take time for these guiding elements to become clear.
Secure support from senior stakeholders
After leadership is set up and ready to go, engage with senior stakeholders to get their buy-in and help them understand the importance of their roles in Agile transformation. All too often, stakeholders stand outside of the process, not attending demos or not providing adequate feedback for teams to make forward progress.
As with leadership, these people are often quite busy, and it may be difficult to find time to bring everyone up to speed—but it is a step that must not be missed.
Build a cross-functional transformation team
Once leadership and stakeholders are ready to go, the next step is to build the “dream team” that will bring this transformation to life. You will want a diverse team covering all levels of the organization, from leadership to those who are doing the day-to-day work. Make sure you have enough coaches available to assist the teams you want to work with.
The people on the transformation team should want to get involved—not ordered to do so—and they should also be Agile proponents.
Once leadership and stakeholders are ready to go, the next step is to build the “dream team” that will translate the Agile transformation roadmap into reality.
Develop a tailored transformation strategy
A tailored strategy includes a pilot program that allows you to see how things go with the first team to onboard your Agile transformation plan. This team should comprise willing participants who are excited to be on the cutting edge and who will provide honest feedback. At the end of the pilot, your group use this input to make any required changes in helping the second group succeed.
It is critical to do retrospectives after each team goes through its process and a few weeks have passed to find out what’s working and what isn’t, especially before you kick off another team.
I find that rolling out the changes to one to two teams at a time is often more effective than trying to roll out to a vast number of teams at once. By keeping the transformation smaller and more manageable, you won’t need as many coaches to keep all the plates spinning at once.
Also, if you start small and keep it small, if you do run into roadblocks, you can see them early and work with those outcomes, to keep them from snowballing and creating mayhem.
This transformation strategy will change over time as the cross-functional transformation team learns more along the way from the different teams as they transform.
Prioritize quick wins
Creating a few quick wins and fun initiatives—things you can share with the large group as the changes roll out—is always a good idea, so that other team members can feel good about the whole transformation. Then you can get a bit of “FOMO” going, so when it’s time for the next team to go through their transformation, they are more likely to be excited about it.
Scale Agile practices across the organization
Once teams are up to speed and transformed, you can then embark on the next phase of the process: scaling or group planning. Often teams will do “practice” group planning on their own to start.
Scaling is the second hardest thing to do in the Agile transformation. It can be a challenge to figure out the different value streams in diverse groups and which teams have dependencies on others. Some transformations I have worked with have started at the value-stream level rather than the team level.
Group planning can take a while to get used to, so let teams know they will get the hang of it even if things don’t go perfectly the first couple of rounds. Agile is also about learning along the way.
Measure progress and adapt the plan
Measuring progress can provide many insights into how the process is going and whether the transformation is successful. Of course, it takes time to become adept at anything new, so look for baby steps in your progress to start.
Deciding what to measure can also be somewhat daunting. Most transformation leaders measure the amount of work getting done and how consistently it gets done. However, an equally important measurement is the morale of your workforce. It’s easy to become so focused on the output that you forget about the people. And the happier the people are doing the work, the more work they can accomplish and the better the outcomes.
Sustain transformation with continuous improvement
Finally, Agile is about continuous improvement. Opportunities will become apparent in the process of doing retrospection or reflection practices, often at the team level.
One misstep I often see is leadership not making time for this practice. It’s important that all teams involved in the transformation do these reflective practices. If leadership isn’t improving as the teams improve, a mismatch will eventually arise, and it’s important for everyone to stay on the journey together.
Scale Agile practices across the organization
Creating an Agile transformation roadmap is an ambitious undertaking, but with a sturdy foundation, thoughtful planning, and ongoing commitment, your organization can thrive in a more Agile environment. Each step, from assessing readiness to measuring progress, is part of a continuous cycle of improvement that supports flexibility, efficiency, and collaboration. Remember, Agile transformation is a journey, not a one-time change. With a focus on incremental progress and cultural alignment, your organization can not only adopt Agile practices, but also sustain them, fostering resilience and innovation at every level.
Samantha Sieverling is a Solution Manager in Logic20/20’s Digital Transformation practice. A senior Agile coach with over 20 years of experience in coaching, transformation, and product management, Samantha is known for fostering psychological safety and high-performing teams. She combines deep Agile expertise with compassionate leadership to help organizations develop adaptable, collaborative cultures. Samantha’s extensive credentials and hands-on experience across multiple industries have made her a trusted guide in helping teams and leaders navigate their Agile journeys successfully.
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