Building a Successful Roadmap

When I first started working as a team lead, most of my days were filled with solving urgent problems raised by customers and colleagues. There was no hiding from it – I was firefighting a long list of problems, with no end in sight. My team resolved many issues, but new ones kept coming. There was always more to do than could be done with the existing resources. My reactive approach kept us busy but didn’t move the team forward.

I knew that not all issues were true emergencies and that better planning was needed, but didn’t have enough experience to be able to separate genuine incidents needing urgent attention from chronic underlying problems that needed a more thorough review. In the first three months of my job my instinctive approach was to ‘just get on with it’, and it had its merits. Maintaining status quo in the short term gave me breathing space to establish relationships with key stakeholders and to get a good understanding of the culture of the organisation – something that is fundamentally important for long term planning. Once this was done, I was in a good position to start working on a roadmap.

What is a roadmap?

A roadmap is a communication and stakeholder management tool which defines milestones required to reach strategic goals over a medium to long term. Roadmap usually includes strategic goals, milestones on a timeline and rationale. You can start working on a roadmap by filling out a simple table with milestones against each calendar quarter. The roadmap can later take form of a PowerPoint presentation, a Word document or an infographic. The way the roadmap is presented will be most effective if it reflects the culture of the organisation. A formal document can work well in regulated industries, whereas scribbles on a napkin can be just as good in a newly founded start-up.

The main focus of the roadmap is on medium term goals. The timeframe goes beyond what is typically covered in development backlog, but doesn’t go as far as long-term vision and strategy.

Key milestones

Roadmap milestones represent important deliverables: projects, releases, digital marketing campaigns, software upgrades. All milestones need to be linked to strategic objectives, have a significant impact on the business and deliver value. Capture this information by adding a short narrative with rationale for each milestone, which aims to answer why the milestone is important, why it is necessary at this point in time, and what its benefits are to the business.

The way milestones are positioned on a timeline reflects a rough estimate of how long these initiatives will take, but it is important to understand that these estimates are not commitments – they are best guesses. It may be useful to add markers on the timeline with important dates that influence business targets – for example seasonal events, trade shows, end of a fiscal year and so on.

Stakeholder alignment

Ultimately the goal of the roadmap is to achieve stakeholder alignment on what needs to be delivered over the next year or two and in what sequence. The roadmap represents features and services that your customers are looking for, initiatives that your project sponsors are willing to support and projects that satisfy security, legal and compliance requirements – all aligned beautifully in a single document.

The roadmap document however is simply the evidence of the stakeholder alignment. That’s why a roadmap on a napkin can be just as effective as a long Word document with three appendixes. If all stakeholders are happy with it, it works.

To ensure stakeholder alignment, follow these steps:

  • Identify stakeholders and arrange 1:1 meetings to gather input;
  • Allow sufficient time for stakeholders to provide information and feedback;
  • Send updates to all stakeholders as the roadmap evolves;
  • Hold a meeting with all stakeholders to secure alignment.

Resist the temptation to use intuition in order to cut corners and produce the roadmap faster. Roadmaps created by one or two people in isolation from the rest of the organisation lack stakeholder buy-in that’s fundamental to the roadmap success.

Benefits of the roadmap

Roadmap shifts the conversation between stakeholders from arguing to collaboration, which in turn makes it easier to unblock barriers to delivery. For example, problems with funding or skills gaps can be discussed and addressed ahead of time. Roadmap helps teams to prioritise their work too – knowing that there is a plan for all important activities makes it easier to focus on the task at hand and avoid the overwhelm. It also means that there is a clear snapshot of the ‘bigger picture’ which allows teams to challenge the value of unexpectedly complex tasks against the strategic goals and re-prioritise if necessary.


Roadmap is a communication tool and a living document, which aims to make strategy a reality. The end result – whether it’s a powerpoint presentation or a document – should be simple, but the process of creating an effective roadmap takes time. Once the roadmap is done, keep sharing. Communicate key milestones to teams that haven’t been involved in the roadmap creation, but are impacted by these decisions. This way everyone is on board and working together towards a common goal.