Agile Roadmapping — Planning for Success

Having a clear vision is key when working in an Agile setting. However, translating this vision into a strategy, whilst still allowing room for an agile way of working that enables flexibility, creativity, and ownership, is challenging. In this article, I show how to set up an Agile ‘goal-oriented’ roadmap that will provide you with the best of both worlds: a strong focus on succeeding and achieving your goals and still remaining agile for the unexpected.

Teams and stakeholders sometimes feel lost when it comes to translating a long-term vision to short-term objectives and real measurable outcome. This is where a product roadmap is typically used to provide clarity by visualizing the product strategy for stakeholders and teams. Roadmaps can thereby end up being used as ‘wish lists for Santa’: they promise that certain features and deadlines will be delivered by a particular moment in time. Sales departments use such roadmaps to attract and entice prospects. This could impart a great deal of pressure on companies, who are now forced to deliver particular features, and may lead to frustrated customers when a feature is not delivered on time.

A more agile way of communicating your strategy is by creating a so-called ‘goal-oriented’ roadmap, which visualizes the business goals you are aiming to achieve and their ordering. Goal-oriented roadmaps provide focus and clarity to your teams and your stakeholders. Unlike most roadmaps, which usually present groups of features, goal-oriented roadmaps deal with goals.

Instead of debating features and their technical realization, goal-oriented roadmaps are allow you to focus on strategic objectives, strategies for investment, and stakeholder management. In other words, rather than being preoccupied with technical implementation and building the product right, goal-oriented road- maps allow you to concentrate on building the right product. Technical details can be sorted out at a later stage by the members of the development team and should not be in the spotlight at this point that’s where your USPs, exciters, and innovative features should be!

How to get started?

One of the easiest techniques I have experienced to get started with an Agile roadmap is inspired by the book ‘Innovation Games’ by Luke Hohmann, which is based on a workshop technique called ‘Remember the future’. This technique is successful because it describes the outcome of your vision in a detailed manner, which makes it more tangible and plausible for all of the participants. Hohmann’s technique approaches your roadmap as if all of your plans became a reality and all of your assumptions were true. Of course, in reality, this is hardly ever the case. That is why, like everything else in Agile, creating a goal-oriented roadmap is an iterative process driven by evidence-based insights rather than speculation.
To prepare and run a ‘Remember the future’ workshop, you’ll need the following:

  • A cross-functional group of people who have knowledge of what
    should be on your roadmap and how to reach these goals;
  • A (clear) vision for your product;
  • Good understanding of your customers’ needs (i.e. pains and
    gains), your position in the market and your competitors;
  • A basic workshop kit (containing Post-its, Sharpies, a timer, etc.)
    and a suitable space to run a workshop.

4 steps to create your Agile Roadmap

Once you have all the ingredients required to get started, use the following 4 steps to create the first iteration of your Agile roadmap:

Product vision

Step 1: Connect to the vision
The first step you’ll take as a group should be that you reach an agreement on what your vision entails. This can be done by discussing:

  • What your vision means;
  • What customer group(s) you are focusing on;
  • What customer needs you are planning to address;
  • How these customer needs can be translated to actual measurable business goals?

Your discussion can be facilitated by using a template such as Roman Pichler’s Product Vision Board.

Product Vision Board - Roman Pichler

Step 2: Teleport to the future
With your Product Vision Board in mind, move yourself a couple of years into the future. Imagine that your vision was spot on and that all of your assumptions were true, which has made your product and company very successful. Describe the big picture of what your

product has become and what you have achieved. Make sure you have a good understanding of the market and its developments and try to incorporate these insights into the outcome of your vision. Capture the outcome of your efforts by creating a cover story (see Figure 3), so you’ll have a physical artifact you can reflect on with your stakeholders.

Step 2.5 (optional): Validate the outcome
Validate the outcome of your vision by asking yourself (and others) the following question: “what can we do with this outcome that we cannot already do today?” By answering this question, you’ll be able to verify that your vision will actually achieve the desired outcome for you and, more importantly, for your customers.

Step 3: Identify milestones
Now that you are in the future and have already described what im- pact your product will have, look back and see what business milestones have been achieved to get you to this point. Think of at least 2–3 major business milestones and describe them as detailed as possible. When describing these milestones, try not to focus on features, but actual business objectives. For example, “100k paying users, active in 5 different countries outside the US”, or “fully automated production process”, etc.

Cover story - Grove tools

Step 4: Describe features
Describe what features your product needs to support in order to achieve each of the previously identified milestones. You could
use any brainstorming technique here, but my preferred method is creating a story map together with your team(s) and stakeholders for each of the milestones. Try not to go too detailed in this step, as these will probably change once you actively start pursuing the milestones.

Agile Roadmap based on Business milestones

Step 4.5 (optional): validate the milestones
Double check with your team(s) and stakeholders to see how much of the described milestones and features are already in your current product backlog, and check if you are actively working on the right initiatives to get you to where you want to be in the near future. In my experience, this step can be very confronting due to the fact that product leaders can come to the realization that they are like most of us: absorbed by short-term plans, day-to-day tasks, and investing too little in achieving their vision and remaining relevant to their customers in the imminent future.

Conclusion: rinse and repeat!
By following these steps you’ll have the first version of your goal oriented Agile roadmap. Do not expect it to be perfect the first time. The value of the first few versions is that they give you a good starting point for approaching the future, using visual and easy to understand artifacts that can be used to talk to stakeholders and customers, leading to further refinements of your roadmap. What makes this approach specially suitable in an Agile setting, is that it results in a goal-oriented roadmap and that it is created with the notion that it will be revised as we learn more later in time.

Gino N. Shahidi

Gino is a Product management coach and trainer, with vast experience in Product owner and Product management roles in both startup and corporate environments.

Gino’s area of focus is Agile Product management and Innovation. Inspired by Agile and the Lean Startup methodologies he is driven to make innovation a part of organization’s culture, minimizing the risks and uncertainties involved with innovation by applying validated learning techniques.

Gino is an product management coach and trainer. Inspired by agile and lean startup methodologies he is driven to embed innovation in the organizations culture