Knowing where you are on your digital transformation journey

Peter Maddison
April 19, 2020
Reading time: 7 min

How many of you have been through something labelled as a digital transformation in the past 5 years? Many hands go up, and several people groan. It seems like we are in a constant state of transformation, which is true. Change is the new normal and transformation is the grandiose title given to the work we build around it. 

Yet many transformation efforts stall or even fail. We encounter many reasons for this, including market pressure, hierarchy and blame culture. Even gut instinct being the primary way to make decisions comes into play! Core to most digital transformation efforts is aligning technology to business goals, which often creates problems with delivering the desired change due to their different goals.

When technology departments drive the transformation, they often need help explaining the value. Ensuring stability to reduce rework through innovative techniques and tools may not resonate. Still, we do require change through transformation for our businesses to thrive. Without change, we struggle to keep up with the market and build the adaptive organizations we need. Executing a transformation is a journey, not a destination. Below I discuss three typical stages organizations find themselves in on that journey, how to identify them and what to do next. I call them Getting StartedUnderway, and Where to go next

Getting Started

Sometimes the hardest barrier to cross can be getting started in the first place. Several factors can lead to this, below are some of the most common:

  1. Incentives in the organization are contrary to the transformation, so it is hard to get buy in to begin

  2. There is a desire to change, often from within an area of technology, but they are unsure of where to start

  3. The change needs to be meaningful, but there are too many options of where to start

From here, we start to ask questions to get a feel for what is preventing the change from moving forward. There are some common patterns in the answers:

  1. There is a lot of complexity in processes and technology. Often we hear language like "legacy" or "black box" and find groups or teams that should "be left alone"

  2. Difficulty creating alignment around transformation. Asking the same questions in different parts of the organization is informative. It is common how often we get very different answers.

  3. Unable to establish a sense of urgency. When there is no overriding reason to change, then even if you manage to get started, you will likely stall.

Pushing change forward for the sake of the change itself is difficult to achieve. This is also why change stated in technical terms so often fails to get adopted. It often takes somebody showing the value to the organization to get buy-in to the transformation.

What can you do to counter this? Start by understanding how your organization delivers value. From the decision process through to the customer holding your product. Pick one of these value streams and run a (lightweight) value stream mapping exercise. This will allow you to identify where best to start. Map this to your organizational goals and ensure you can explain the business value. In turn, this helps get buy-in to undertake the investment. Now you can start to execute and bask in the glory of moving your organization forward.


In the second stage, we encounter organizations when their transformation is underway. They have had some initial success and are looking for guidance. Often they express this as an Agile transformation or DevOps adoption. Yet it is also expressed as business process improvement or service management modernization. Whatever the label, it involves changes in tooling, ways of working and org structures. It is also common that they did not get the return they planned.

When we ask questions now we find the following:

  1. There is an unclear vision goal. This occurs from not having taken the time to define what you are looking to achieve from the change. Without initial measurements, it is hard to determine if the change had an impact.

  2. The transformation is process bound, often with a heavy project focus. For changes to the product delivery process, this is especially true. When the organization's financial models expect time-bound project delivery, they struggle funding teams. They are not set up for the continual, team-based, product delivery model. When these two worlds collide, problems ensue.

  3. Transformation operates in isolation. Sustaining the change requires generating engagement within the rest of the organization. If you are part of a team changing the culture of your organization, you cannot be solely accountable. For the change to happen, other parts of the organization need to adopt it without you.

  4. Lack of understanding of the holistic impact. This occurs when you have started the change well but not gone back to verify your impact. You have addressed the initial bottleneck in the value stream. Now you need to go back and remeasure as that may not be the right place to focus anymore. The goal is to find the next bottleneck and start to focus there.

The good news at this stage is that the transformation is salvageable. With a few tweaks in the direction, we can reinvigorate the transformation. When applied in the right way, modern practices allow us to achieve amazing results. Yet it is hard work, and you need to roll up your sleeves and get in there. Don't give up.

Where to go next

In the third scenario, organizations consider their transformation successful, yet they are unsure where to go next. This differs from the second stage, especially when they are unsure whether to continue. We see the following:

  1. Transformation operates in isolation. As with our second scenario, the transformation is in one part of the organization. It has not spread beyond the initial area and is not ingrained into the language of the organization. For example, when delivery teams are referring to changes requiring the "DevOps team". They are not yet talking about how they enable themselves to solve their problems.

  2. Lack of broader strategy. Although the transformation has brought in some new capabilities, they are not tied to a larger vision. There needs to be an understanding of the broader business goals rather than just a desire to bring in the latest industry buzz word. Building a data strategy alone will not generate business value without context.

  3. Limited visibility to the impact of the transformation. Although the transformation has introduced change, we must consider what this enables. Parts of the organization are now capable of going faster, but what does that enable us to do. Sometimes they are unable to due to legacy planning and financial processes. 

To resolve this, revisiting the drivers for the transformation is key. If there is not a strong vision, create one. From there, create a roadmap. Learn how to integrate what you have learned to date into other parts of your organization. Most of all, do not believe that because you reached a certain date, that change is over. Identify your champions and charge them with determining where the transformation should go. This way your transformation will continue once the consultants leave the building.

Find where you are on your journey

Wherever you are in your Digital Transformation, it is important to cut through the buzz. and identify where you need to focus. Work out how to create alignment across the different parts of your organization. The conversation is not about DevOps, Agile or Digitization of process. It is about creating a common understanding of the change across the organization. Especially about how you deliver business value and how the transformation impacts that.

If you are transforming, ask yourself into which scenario you fall. Conduct a Value Stream Mapping exercise and identify where you are today. Learning where to improve is a great way to do this while creating visibility to the process.


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