Roadmap Thinking – How to Build a Strategy Using a Roadmap | Roadmap Crafting Checklist Included

What is a roadmap and why do you need one?

Of course, since the 80s, many other definitions and views were expressed. But they have some things in common – they all agree that a roadmap should provide a high-strategic view of the plan using means of graphical representation. Roadmap planning provides numerous vital benefits for a business, including:

• Aligning investments and research with the organization’s goals and strategy
• Reaching a consensus regarding priorities and required actions
• Promoting communication across various key stakeholders, which facilitates ongoing action and dialogue
• Keeping participants on the same page and preserving the dominance of the big picture over present-day problems

Now let’s discuss the strategic roadmap structure. Any roadmap should answer three fundamental questions:

1. What do we want to achieve?
2. Where are we now?
3. How do we reach our goals?

These questions naturally define the structure of the roadmap. Below, you will see how to answer them properly and how to build your strategy around them.

How to define goals for a roadmap?

This first step is arguably the most vital. After all, if you don’t set your targets right, it won’t matter how well you perform other steps – you will be heading in the wrong direction altogether. That’s why it’s crucial to grasp a couple of important concepts when you start planning your own strategy.

1) Vision

Vision is all about imagining your organization reaching its goals. Understand how this will affect it, what implications this might have, how the business environment will react, etc. Why is this so essential? Because you don’t want your aims to be set in a vacuum, not bound to real problems and background. Envisioning your company having achieved its targets may help you come up with important related questions, like “what if we actually get there?” and “is this really what we need?”.

Take heed – developing a Vision hides a certain pitfall. Seeing how it is usually a mental product of a business owner or a CEO, Vision can be subject to cognitive biases. This is a topic for another day, but for now – double make sure your goals pass the reality check.

2) Structural thinking

Many of us have heard about Pareto-efficiency – a principle that 20% of our efforts generate 80% of the results, and vice versa. Well, you could say that structural thinking is what you use to determine those most efficient 20% of efforts. This is how it works (don’t forget to set KPIs for each level!):

• choose your grand goal (for instance, earn X amount of $)
• derive subgoals that are integral to the success of the grand one (let’s say, sell Y amount of goods and reduce product cost by Z)
• derive sub-subgoals, and so on (the number of levels can vary depending on the size of the system; for SMBs 3-4 levels should be enough)
• use subgoals to define milestones for your roadmap (more on that later)

The pitfall of structural thinking is in how difficult it is for us humans to conduct proper induction. In general, you can’t be 100% sure that whatever subgoals you’ve derived are actually the crucial ones. That’s why it’s always recommended to double-check them by performing a reverse operation to see if your trains of thought come back to the initial point.

3) Black Swan theory

The state of modern markets can be easily described by the VUCA concept. That is, they are Volatile, Uncertain, Complex, and Ambiguous. Any old-school long-term planning becomes nigh-impossible in such an environment. It takes a business Vision, Understanding, Clarity, and Agility to have a chance to succeed in these markets.

In this regard, no wonder why the Black Swan theory by Nassim Nicholas Taleb becomes more and more popular nowadays. In this theory, a black swan is an event that has a major effect on business results, yet occurs unpredictably. What’s important is that you don’t have to try and forecast such events, but rather to build up the robustness of the business – being able to withstand the negatives while still exploiting the positives. Be sure to plan for big swans when deciding on your goals.

How to define your current position for a roadmap?

Once you know where you want your business to get, you should analyze its current state with the end goals in mind. Take a look at your resources, market niches, competitive environment, understand which of them can influence your path towards the targets, and how. Think about what factors in the past brought you to the present situation.

This stage, while obviously important, is highly subjective and depends on the organization and its goals. So, alas, there isn’t much we can add here – you’ll have to figure out your current state yourself.

How to outline the path towards your goals in a roadmap?

Now that we know where we are and where we wish to get, it’s high time we decided how. At this stage, we’ll once again use structural thinking, but now – to determine which steps and tasks will result in reaching milestones. Which, in turn, will facilitate the accomplishment of the aims.

The first important concept to understand at this stage is GAP Analysis. Using this method, you can identify critical… well, gaps between your current and desired states. This is a broad topic that we recommend you delve deeper into, but this is how it works in general:

• Define your business’ key components that affect the dimensions in which your goals and subgoals lie. For instance, your customer goodwill may be influenced by product quality, helpfulness of client support, and post-sale marketing activities – those are the components.
• Determine how these components must be changed to promote objective fulfillment.
• Analyze organizational capabilities to affect the components. Perhaps, you outsource your customer support, so there’s little you can do to increase its quality, but you employ your own marketers and have full control over their activities.
• Choose the technical solution. Basically, this is answering the hows of your strategy. Will you update your developers’ devices so they can work more efficiently, or would you rather hire a manager who can optimize their work?

Now that we’ve conducted GAP Analysis, how exactly do we craft the roadmap? A universally applicable standard for building any kind of Roadmap, whether you develop it in a dedicated planning service, like Goals by KeepSolid, or draw it on a sheet of paper, is a Balanced Scorecard (BSC).

It is an instrument that, whatever the form you choose, allows setting activities and goals AND (this one is important!) helps to keep track of the task execution. On the principle of BSC, any strategy should:

1. Be incremental. Never build a long-term plan so rigid that it doesn’t allow ad hoc changes in case of unpredicted events (black swans, remember?).
2. Include:
   • List of components or dimensions
   • List of what must be changed about them
   • Specific actions to change that
   • Expected outcome or benefits of these changes
3. Visualize dependencies between tasks.
4. Get updated systematically to always represent the current situation and the business’ chosen direction
5. Be available for key stakeholders at any time for them to be able to align their actions according to the global goal, not only their ongoing tasks.

Roadmap Crafting Checklist

1. Develop a Vision of the future that you want your organization to get to.
2. Translate your Vision into a concrete, measurable global goal
3. Derive a number of subgoals that lead towards achieving the global goal (3-4 levels should be enough for an SMB)
4. Plan for an excessive robustness of your business to resist black swans
5. Analyze your business’ current state with the end goals in mind
6. Conduct GAP analysis:
   • Define your business’ key components
   • Determine how these components must be changed
   • Analyze organizational capabilities
   • Choose the technical solution
7. Draft a roadmap on the principle of Balanced Scorecard. Make sure it includes:
   • List of components or dimensions
   • List of what must be changed about them
   • Specific actions to change that
   • Expected outcome or benefits of these changes