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7 tips for a successful digital roadmap

In this post, Digital Strategist Emma Andrews breaks down the elements that make up a successful digital roadmap.

Emma Andrews

By Emma Andrews, 1 March 20197 minute read

In an earlier post, ‘Creating a digital strategy roadmap’, we provided an overview of the roadmapping process. Here, we take a deeper dive into what makes a roadmap really have an impact. We’ve broken it down into seven key elements.

1. Start with a strategy

Companies fail to make the change they intend approximately 70 percent of the time due to lack of stakeholder engagement, according to the Project Management Institute.

Before you can embark on creating a digital roadmap, you need a strategy. A strategy creates the big picture and long term objectives; while a roadmap lays out the details behind how you will get to where you intend to go. Your strategy is your reference point that you can always go back to and get an answer whenever you have doubts about the point of any initiative. 

If you don’t have a digital strategy (or a clear one) then you’re not alone. According to a study by Smart Insights, 46% of brands don’t have a defined digital marketing strategy, while 16% do have a strategy but they haven’t integrated it into their marketing activity.

If you find yourself among the 54% of brands without a digital strategy, here are some tips to keep in mind when creating one:

  • link your strategy to your business values and mission
  • identify how you will measure success with a few important KPIs 
  • outline how you will get there with some very high-level initiatives.

2. Allow enough time

On average, the process of putting together a roadmap takes between one and three months. You’ve got to be willing to start on your plan knowing that you won’t know everything at the outset. You’ll find surprises, challenges and opportunities along the way. Your roadmap needs to factor in these uncertainties — and needs to be flexible enough to allow you to change course when necessary, something we discuss in step 7 below.

3. Don’t overlook the gold at your fingertips

The good news is you already have a lot of what you need to get started. Compare your knowledge base against the checklist below and highlight what’s missing. Decide how you are going to fill the gaps, get additional information, or create workarounds where information is missing. Review what you know now and the data collected. What trends do you see? What are the unique links between the core insights? Are there areas of obvious weakness or strengths? You’ll need input from experts across a variety of teams and departments. That includes, for example, customer support, product teams, sales and marketing.

Internal resources checklist

A sample internal resources checklist. Download our roadmapping templates, including an editable version of this checklist.

4. Make your initiatives actionable

Many people think that having a few digital initiatives constitutes a digital roadmap. But a digital roadmap is more than that. It’s an integrated set of initiatives; not just a series of ad-hoc projects. Your roadmap should provide a step-by-step path to achieving your strategy – through channels, messaging and processes. And it should be tangible, actionable and immediately applicable.

Digital roadmaps should be created and maintained as part of collaborative workshops that involve all relevant stakeholders. This is key to creating an integrated digital roadmap that factors in all relevant initiatives and is focused on achieving an agreed, shared business goal, rather than delivering a series of isolated digital initiatives. 

The template below will help you break down the detail of each initiative to ensure that it’s actionable. Initiatives should be addressed individually and treated as (almost) discrete projects when planning, as some may be interlinked or interdependent on each other. 

Some things to be wary of when completing this template:

  1. Target audience – this is never ‘everyone’ / all of them / the whole database
  2. Responsible – this should only ever be just one person who is ultimately accountable for getting it done. Having three names against an initiative is a sure-fire way to get nothing done.
  3. Impact/KPIs – keep it simple with just one or two measures per initiative; otherwise you’ll end up drowning in data that you find impossible to put into action.
Actionable initiatives worksheet

This worksheet illustrates one way to set out your actionable initiatives. Download our roadmapping templates, including an editable version of this worksheet.

5. Prioritise all the initiatives

If you’ve got to this stage and your roadmap contains 1000 initiatives, you need to prioritise what should be included. A list of that many initiatives would be more accurately described as a project backlog than a roadmap. Only those initiatives that serve your strategic goals and vision, and that always relate back to business goals, should earn their place in the roadmap. Be ruthless about which initiatives to include and which to leave out. 

Greg McKeown, author of Essentialism, suggests that there are three steps to prioritisation:

  1. Deliberately distinguishing the vital few from the trivial many
  2. Eliminating the non-essentials
  3. Removing obstacles so the essential things have a clear, smooth passage.

Instead of just jumping into a project, look for obstacles that hold the whole system back and make a list. Prioritise the list using the question, “What is the obstacle that, if removed, would make the majority of other obstacles disappear?” Once you’ve identified your obstacles, start to brainstorm ways to remove them.

Another way to prioritise initiatives is to create a priority matrix (see below). This matrix allows you to compare cost vs time vs expertise (i.e. people resources to undertake the work). Assess each digital initiative’s value against complexity, cost and risk. This helps to establish whether a digital initiative is worth delivering, and its capacity for achieving results against the pre-defined goals.

Alternatively, when we plan with clients, we make it interactive and use Monopoly money as a proxy for actual budget and every stakeholder “invests” in what they think are the top priority initiatives. 

Priorities matrix

A priorities matrix, comparing cost and time to execute, can be an effective way to prioritise initiatives.

6. Represent your roadmap visually 

You are likely to show your roadmap to many different stakeholders, in many different meetings. Each stakeholder group will have a unique focus and set of priorities, and each meeting will call for you to delve into different aspects of the roadmap.

A roadmap is a communication tool — an execution strategy you will use to convey your plans and goals to a variety of stakeholders. And the best way to communicate a complex set of initiatives is visually. To avoid creating separate roadmap documents for each stakeholder group, build a single roadmap and simply zoom in to the stream or initiatives that are relevant to each group. 

For more detail on how to represent your roadmap visually, download our Digital Roadmap Toolkit.

Structure 1 - By theme

The aim of this approach is to create fewer, more manageable categories that the initiatives sit under. Themes are a great way to keep your roadmap high-level. It’s an especially useful way to present your roadmap to your C-suite, to help them quickly understand where you’re going with the plans and why — without bogging them down with specific details.

Roadmap diagram

Structure 2 - By initiative across time

A typical timeline-based roadmap is organised by months or quarters according to when you’re delivering the initiatives. Like theme-based roadmaps, timeline-based roadmaps are also typically used when presenting to executives — because executives want to see deliverables and milestones. This format is indicative of work over time; not a stick to beat you with if something moves out. It’s designed to create an order. In fact, things should move as you learn what’s working – which brings me to my next point…

Roadmap diagram - by initiative

Download our roadmapping templates, including an editable version of this roadmap.

7. Be prepared to review and evolve the plan 

Before you begin implementation, make sure mechanisms are in place to track and measure performance so that you can compare actual metrics to your KPIs. Review your roadmap on a regular basis and update it in line with real-time analysis, changing business requirements, and external influences such as what competitors are focusing on, market forces, and disruption attempts. A successful roadmap will be one which is able to constantly evolve in line with continuous insight. 

Ideally you should be reviewing your roadmap on a monthly basis. These monthly meetings don’t need to take a lot of time – 30 to 60 minutes should suffice. But it is important that key team members report on their progress toward the goals they are responsible for – including reporting on metrics. 

Your specific roadmap priorities might need adjusting in light of new information. You should be prepared to adjust focus in your roadmap, reallocate resources or otherwise change direction only if doing so is in alignment with the business's high-level strategic goals and vision. The aim is to optimise and sequence those interactions over time, and identify areas for future investment.

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