Strategic Management

A Roadmap is Worth More Than a Thousand Words

Failing to plan is planning to fail is the saying, but to what degree is a plan relevant in a dynamic environment with multiple stakeholders and multiple sources that can impact the organization and strategic plan. The organization’s environment is adding to complexity and the bigger the organization, the more likely the decision makers will experience a high degree of complexity when it comes to the decision-making processes. 

A  roadmap is in other words a great artefact to use, when the decision makers need an overview of how the individual activities and decisions impact the organization and its possibility to deliver on the decided strategy, and likewise can roadmaps deliver the relevant “framework” for making the relevant decisions. But what is needed in order to build a roadmap that can deliver the overview? And is the roadmap the most important delivery?

Complexity in Decision-Making Processes

Medium-sized and major organizations will eventually experience that decision making processes are becoming increasingly complex, which has impacts the time for when and how the decisions are made. The delay of implementing the decisions does the added complexity e.g., in the layers of the organization impacts the organization’s ability to adjust to its environment.

The sources of complexity in organizations are many, but you will most likely experience complexity increase when:

  • New hierarchies are introduced, meaning decisions have to be made by people far away from actual production of the organization.
  • New comprehensive rulesets are implemented and enforced.
  • New structures of the organization e.g., the enforcement of new department structures and new ways of communication.
  • New services, products and processes are introduced and leads to new ways of working where limited existing knowledge is available.

The increasing level of complexity in organizations cater for the establishment of roles like enterprise architect, business architects and solution architects who can coach the different stakeholders of the organization to navigate the complexities and to enable coherences. One method to assist with the guidance of the stakeholders is the use of roadmaps.


A roadmap has to be individualized for the specific organization and its specific industry. A good roadmap includes perspective for market orientation, business related themes and technical deliverables. It is almost needless to say, but the roadmap must include a time perspective and the perspectives, those earlier mentioned, have to be connected. 

The enterprise architect would have to consider a few different themes before the development of the roadmap takes place, and the primary concern to address during the planning is to consider that the roadmap itself is not the value adding component. The primary value adding component of the roadmap is the process of delivering it. The artefact as such is valuable for communication to different groups of stakeholders, though the value of creating clarity is mainly developed during the roadmapping process, since the activities in most cases would involve executive stakeholders.

The Roadmapping Process

The enterprise architect will have to act as the facilitator and as a subject matter expert, when or if, questions are asked during the sessions in the process by the different stakeholders. Likewise, the enterprise architect can as such not own the roadmap, except, if he or she is a member of the executive committee of the organization.

First and foremost the enterprise architect has to ensure executive sponsorship for the process. When the sponsorship has been ensured, then the relevant stakeholders have to be identified and engaged. The first meetings will likely have to be done individually with the stakeholders, so they are prepared for what will be done during the workshops where groups of the stakeholders are engaged. One of these group workshops would include the kick-off session, which will have to provide alignment and commitment to the process, since without the “geist” or “spirit” to take part in the process for developing the roadmap, then it is likely very little will happen. 

The enterprise architect will also have to work on ensuring a vision is articulated as part of the roadmapping process, and the vision is captured, so the participants in the process can support the mapping of the roadmap towards achieving the vision. The vision and the prework to the roadmapping process can be captured by using scenarios and undergo a specific process for this with the executive committee, so they have an aligned view of the vision, before the roadmapping process is commenced. 

During the roadmapping process the enterprise architect has to ensure that the participants do not begin to suffer from group thinking, since the best possible outcome of the process will be produced by a diverse group of stakeholders, who can challenge different hypotheses and perspectives in the roadmap. This is to be done through the first round of workshops. The enterprise architect will also have to consider engaging the stakeholders individually before the second round of workshops is commenced, since there likely will be a different group of stakeholders involved in these.

The second round of workshops will usually include the subject matter experts e.g., software engineers, solution architects, logistics specialists, sourcing specialists, operations specialists, security specialists and a like. The specialists will during these workshops provide clarifications on how the different deliverables are interconnected, and what impediments have to be dealt with as-well.

The third and last round of workshops in the process of developing the roadmap will be concluded by a presentation for the members of the executive committee. They will have to commit to the roadmap before the organization as such can begin executing as according to it. Before the presentation to the executive committee the deliverables in the roadmap will have to be described as a portfolio of projects (in some cases as portfolios) so program managers and project managers can assist in delivering the projects.

After the last round of workshops have been completed, then it is time to involve the stakeholders in the organization that did not take part in the workshops. This can be done creating a few rounds of presentations so the stakeholders are informed and they can ask questions regarding how to proceed with the roadmap. The stakeholders can prove to be regular employees as well as middle managers like head of departments and senior vice-presidents. Besides the presentations, then “company town hall” meetings can be made use of in-order to spread the knowledge of the roadmap, and in the case of this, the enterprise architect should take part of these to assist answering the questions.

The roadmap has to be published, e.g., at the organization’s intranet, so the executives, middle managers and the employees can look information and “navigate” accordingly. Afterwards, the enterprise architect will have to pivot to a “Plan – Do – Check – Act” approach to make sure the roadmap is kept updated and implemented through the project portfolios. 


The primary value adding activity of developing the roadmap is the process where the different stakeholders take part in developing the roadmap. The roadmap will have to include a market perspective, include business related themes and technical deliverables.

The second most important outcome of the process is the roadmap, which can be communicated to the relevant stakeholders in the company, and in some situations to stakeholders outside of the company. With the roadmap in hand it will become easier for the stakeholders in the company and its environment to navigate the complexity.