Five Key Stages in Building a Digital Strategy Roadmap

Posted / 30 April, 2019

Author / Enginess

Five Key Stages in Building a Digital Strategy Roadmap

In this article, we share our five-step process for creating a digital strategy roadmap.

Last week we kicked off the series "Digital Strategy Roadmaps: A Step-by-Step Approach to Success". Over the next couple of weeks, we will post articles sharing best practices around digital strategy roadmaps. This week we continue the series with the key stages in building a digital strategy roadmap.

Stage 1: Evaluate your current state and gather objectives

The first step is to evaluate and document your current state and gather objectives against the problems that are experienced, felt or foreseen today. In this stage you are asking:

“How does the process / service / system work today?”

“What’s not working so well?”

“How do we want this to work better?”

The current state evaluation forms the basis for your future state recommendation and roadmap. It is all about building the business case for the future plan and setting up realistic expectations around the execution of that plan. In no particular order, the following kinds of activities are typically undertaken:

  • Discovery with business owners and customers to identify sets of problems and objectives
  • Study and/or audit of existing systems, technology, and processes
  • Review of existing analytics and performance metrics

When an evaluation is done thoroughly, you can feel confident that you have identified all the existing “moving parts”. Knowing the whole picture, you’ll be able to start linking vision and objectives to concrete initiatives.

Digital Strategy Roadmaps Ebook

Stage 2: Vision a future state based on business and user objectives

Next, define the future state through problem-solving against key objectives. Aim for a well-rounded picture that is well balanced and not just the view or opinion of a single business owner or individual.

Business Stakeholders

The first step is to identify and gather objectives from your business stakeholders. The aim is to understand the high-level “desired and required” requirements for the organization as a whole.

End users

The second step is to gather objectives from your end-users. By now, you should have a good idea of what the organization feels is a need or priority. Talking to customer end-users about what they want and need may give you a slightly different result.

Business stakeholders and end-users represent two sides of the same coin. Both sets of feedback should add up. Combined with earlier steps and you have a complete vision of what your digital strategy roadmap needs to deliver. Depending on the complexity of the transformation, the task may take more or less time, be more or less complex with more or fewer groups of stakeholders and end users to solicit input from. In the end, you are looking for insights that support your future vision. It can be as simple as saying: “This digital project is going to have a positive impact on X business goal.”

Stage 3: Bring together the objectives and the initiatives

Now that you know what your current and future states are, you need to link all you have learned so far to initiatives (things to action) that meet the objectives AND capabilities of the business.

The complexity of this stage is often underestimated or skipped altogether.

It is assumed that a digital project will magically drive an organization’s objectives, but that is not always the case. The right technology will drive business objectives only if the business can and will support the change(s) you are proposing.

Who is responsible, accountable, or otherwise involved?

Who is championing the project? Who can make directional decisions?

Who will be impacted by the changes proposed?

What factors need to be considered to ensure the change is accepted and successful?

When you are building your digital strategy roadmap, you need to consciously link it back to the business’ goals and objectives and consider feasibility and viability (capability). Capability is an important factor that will influence your sequencing and prioritization of discrete initiatives within your strategic plan.

Stage 4: Synthesis

Once you have got your requirements, objectives, and initiatives in place. Now, it is time to map it out. Your map can be visual, textual, or something in between.

You will need to organize everything you have gathered into a single communication that is easy to read and understand. This might look like a simple side-by-side comparison; a spreadsheet list; a table or chart; or a visual diagram. Regardless of format, your digital strategy roadmap is a summary of:

What the current state is

What the future state could / should / must be

What business objective(s) you are hoping to achieve

What the needs of stakeholders and end-users are and how to solve for them

Digital Strategy Roadmap: White Board Scrum Style

Figure 1: You can organize your roadmap in Scrum board fashion the old fashioned way, or with software in a variety of different ways (Excel, Word, card sort software, scrum software, swim lane diagram, mind map, flow diagram, etc). It should be simple enough to be understood by technical and non-technical audiences.

Stage 5: Roadmap

Finally, stage five –  putting it all together into a step by step plan to execute.

Sort / Weight Priorities

Assigning priority to your initiatives can be complicated. There are many prioritization methods that can help with sorting. A simplified version of the MoSCoW method usually works well if your group of stakeholders is on the smaller side: Must, Should, Could, Won’t Do.

You can also try Now, Later, Not Doing. Or a basic priority numbering system: 1, 2, 3.


There are often dependencies within complex projects. If these go undocumented, then it’s easy for projects to stall or become derailed. A detailed, prioritized roadmap enables your team to work in the smartest possible way while delivering the future state. An e-commerce experience cannot be redesigned until the inventory management database is updated with additional product attributes. Clean data is a dependency on an optimal front-end experience. 


What must be done in “waterfall” style and what can be done concurrently, in dual track, or agile? Sequencing is all about assigning your initiatives to a viable order of execution.


Check back here over the coming weeks to see more tips on digital strategy roadmaps. 

Can't wait to see more tips? Download the complete guide today.


Digital Strategy Roadmaps: A Step-by-Step Approach to Success

Part 1: Foundations
Part 2: Five Key Stages in Building a Digital Strategy Roadmap
Part 3: End Deliverable
Part 4: Why Bother?

Plan your project right - a step-by-step guide to ensure a successful digital project launch. Read now.
Digital Strategy Roadmap - Free XLS Template. Download.


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