Charting a Digital Transformation Roadmap

This content originally appeared on the W2O company blog

When it comes to digital maturity, there is no more reassuring concept than a well-conceived roadmap. Roadmaps are designed to bring clarity to an inherently uncertain process. A roadmap also suggests a specific destination, but, as we’ve already discussed in the first section of this series, digital maturity is an ongoing process.  

In practice, a roadmap can be very different. Often a grand vision is presented to senior leadership as a roadmap, leaving the team on a path forward that is difficult to negotiate. Conversely, a roadmap can become overrun with minutia to the point where it’s unreadable and susceptible to the smallest pivot. 

We advise clients on drafting a roadmap that is clear enough to communicate the vision of digital maturity, but flexible enough to hold up to any changes in environment, priority, or technology.   

1. Start with Goals, Strategic Initiatives, and Tactics

In last week’s section of this series, we discussed how to set up goals. Conveniently, these goals, strategic initiatives (SI), and tactics will inform your roadmap directly. Start by laying out your high-level goals and prioritizing them. Assign SI to the goals they support. If you do not think your current set of SI will complete your prioritized goal, don’t worry, you’ll have an opportunity to add more in later. Here is an example of what one digital maturity goal might look like.  

Goal 1. Move approval process from paper to digital  

SI 1—Complete RFP of digital approval vendors 

SI 2—Onboard vendors 

SI 3—Pilot with one department 

SI 4—Roll out 

2. Create a Backlog

You may hear a backlog referred to in different ways, but the general idea is that you need a place to store ideas that are not fully formed. You’ll regularly go back to the backlog and flesh out these concepts. To put meat to the bones of these ideas, you will need the major stakeholders and the people executing the digital maturity to work in one room. We often see that these sessions can contain a lot of back and forth, but the end result is an entire team that has a single vision of the path forward. Once this is achieved, these new items can be inserted into the roadmap. 

3. Be Flexible

The number one mistake when constructing a roadmap is locking a team into a year’s worth of work that is likely to change in three months’ time. To avoid this, make sure to align the specificity of the roadmap item with the timing of its execution. In the example above, the high-level goal of “Move approval process from paper to digital” can be scoped out to twelve or eighteen months. However, specific tasks under any of the SI, for example, “Open ticket with IT” will only be brought into the roadmap weeks in advance. The result will be constant goals with SI that span a few months and tasks that quickly come into the roadmap before they are completed.  

4. Socialize with Frequent Updates

Once the roadmap is in good shape, it should be socialized with management to gain alignment. Additionally, we often work with clients to use roadmap socialization as an opportunity to gain excitement with other internal stakeholders. Because the roadmap is updated frequently, it should also be shared on a regular basis—usually quarterly—to show how the digital maturity journey is evolving. In this way, the roadmap becomes not only the path forward for the team(s) involved in digital maturity efforts, but also the main socialization vehicle.   

Key Takeaways:

  • Formulate a clear plan that is flexible enough to tolerate any unforeseen changes. 
  • Establish goals, strategic initiatives, and tactics. 
  • Create a backlog of underdeveloped ideas that can be revisited and enhanced. 
  • Frequently share updates with interested parties.