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Understanding Roadmaps

What is a roadmap?

A roadmap is a tool that assists in the development and communication of plans. It visually represents planned investments over time with the ability to distinguish between different types of work, different business areas, etc. Roadmapping – the process of developing and managing a roadmap, is a strategic planning technique that makes it easy to visualize, adjust and communicate the plans represented by the graphical roadmap.

Roadmaps must support both the ability to plan, and the ability to communicate. Therefore they cannot simply be thought of as a visual representation of proposed and planned activities, they must also contribute to the ability to develop, evolve and adjust those planned activities.

Why do organizations need roadmaps?

In today’s world everyone has to be engaged in strategy execution. Organizations succeed when the right priorities are backed up by the right investments, delivered in the right way to achieve the best possible outcomes. For that to be achieved there needs to be clarity in the strategic portfolio management elements of planning, prioritizing and funding. An effective roadmap provides that clarity by allowing all strategic portfolio management stakeholders to review plans collaboratively, to make adjustments instantly, and to assess the implications of those potential changes.

Gathering current and accurate data to build portfolio roadmaps is often a time-consuming and arduous task.

There must also be clarity in the adaptive project management elements of an organization – the delivery of work using each of the tri-modal realities and all possible work structures (projects, programs, products, etc.). A visual roadmap provides that clarity by being easy to communicate and easy to understand – providing all stakeholders with the ability to understand how their work contributes to the organization and where the relationships and dependencies are.

When implemented appropriately, roadmaps provide a top-down approach that consolidates all change that is occurring in the business, regardless of how that change is structured, which work methods it is being delivered through, and where it is occurring. This integrated and centralized view, and the ability to manage using it, is critical to success. It effectively becomes an approach for the entire organization to envision and orchestrate change.

Types of roadmaps

All roadmaps are physically similar in appearance – a timeline or phased based graphical representation with categorized elements distributed across that timeline or those phases. The categorization can be as simple as different ‘swim lanes’ for different characteristics, or as complex as those swim lanes plus different shapes, sizes and colors indicating additional elements of the contents.

However, while the look of a roadmap won’t vary much, the information that can be communicated will be vastly different, and the way that the roadmap is used for planning will also vary enormously. Roadmap examples that are commonly produced include :

  • Product roadmap
  • IT / technology roadmap
  • Feature roadmap
  • Project roadmap
  • Strategy / portfolio roadmap

Let’s consider each of those with a brief explanation of the information they can display and the way they can be used.

Product roadmap

The product roadmap is perhaps the most common example, and in various forms it has been around for the longest. A product roadmap can be used to identify the development approach and product strategy for a single product. Product management will include new major and minor versions for example; they’ll graphically represent the lifecycle of a product – the various phases from launch to retirement; and product management will show the overall organizational roadmap for all organizational products across all business areas and markets.

A product roadmap can be used both as an internal planning and communications tool, and as an external communication and marketing tool – helping customers understand how products will evolve, when significant evolution will occur, etc.

IT / technology roadmap

In some ways the IT or technology roadmap supports the same concepts as the product roadmap, just applied to technology assets rather than products. It can be used to show the macro level evolutionary plans of IT services, infrastructure, etc.; the evolution and upgrade path for a particular technology asset; and everything in between.

IT roadmaps often include additional graphical indicators to identify platforms, supported business areas and so on. They also tend to have a higher number of dependencies between items on the roadmap to reflect the inter-connectivity of technology assets. Technology roadmaps are useful for all stakeholders but are often relied on by internal teams within the IT function.

Feature roadmap

This can be thought of as a drilled down or more detailed view into a technology or product roadmap. it takes an individual product or asset and identifies when various features, functionality or upgrades will be added. Feature roadmaps are often used as communication tools with external stakeholders to quickly convey the plans for development and the expected availability of new functionality.

Feature roadmaps convey an understanding of how an individual item will develop and demonstrate an organization’s understanding of what is important to the consumers of that product or asset. These tools are often used to support marketing efforts in external products.

Project roadmap

A project roadmap is a useful project management tool for project stakeholders. Unlike a project plan, which can be highly detailed, a project roadmaps is a simplified summary of key features and deliverables. It is often displayed by team member to provide an additional level of information.

Project roadmaps tend to be more informative for stakeholders than status reports, communicating key information (expected completion date, percent complete, etc.) in a way that is easy to consume without a detailed knowledge of how the project is being run.

Strategy / portfolio roadmap

This is the type of roadmap that is most commonly being referred to today when organizations talk about roadmapping. It represents the highest level summary of the strategic priorities, the top-down perspective of the planned investments that are aligned with those priorities to deliver business goals, and key information around those investments. It will also identify all of the dependencies between strategies and investments to allow for effective planning and adjustments, or the use of what-if analysis software and so on. The strategic roadmap can be drilled into to create departmental, product, technology and more roadmaps to allow for complete integration of work from top to bottom of the organization.

The strategic roadmap is actively managed by executive leaders as part of the strategic portfolio management process to ensure that they are focused on the right priorities and that current and planned investments align with those priorities. The portfolio roadmap represents a subset of the strategic roadmap that represents the initiatives that are currently funded or that have planned funding approvals for execution within the current business cycle.

The strategic and portfolio roadmaps are the core communication vehicles used to convey information on strategy, and the work being done to execute on that strategy, to all stakeholders.

What makes a good roadmap?

All of the roadmap examples above achieve something different. But, to be effective, all styles of roadmap must communicate a lot of information in a clear and concise manner. They must be easy to maintain, easy to understand, accurate, and complete. To achieve that, they should have a number of common features.

  • Time phased view
  • Dependencies
  • Functional integration
  • Milestones
  • Automatic Updates

Time phased view

This is at the heart of all roadmaps. While there can be additional views into the information – by phase, status, ownership, strategic alignment, etc.; and there isn’t just a timeline presentation method (card based is also common, and other formats like radar maps are also possible); the ability to see current and planned strategies and work across a timeline is key for easy communication of lifecycles, growth and related progress.

The time phases must be flexible – annual and quarterly at the more strategic level, monthly and perhaps weekly at more detailed levels such as with a project level roadmap. The timeline may also extend several years into the future to represent long-term strategies and intentions, and it may include the recent past to add context to current work and near-term plans.


Organizations don’t deliver work in isolation. Every strategic priority, every investment, every piece of work is dependent on other work areas, and has other elements dependent on it. Those dependencies must be managed effectively, which means they must be understood. Displaying those dependencies on a roadmap is therefore critical.

Dependencies can be created with simple lines between tasks, creating a relationship that can then be further explored and managed. Dependencies are the first step in understanding how to manage milestones and relationships between work areas, how to address risks around those dependencies, and understanding the implications of any adjustments that are made. They also helps to portray dependencies around resources (financial and human) and add depth to what might otherwise be an overly simplified view of the work.

Dependency management is an important part of strategic planning and execution. There aren’t just single dependencies between two tasks, investments or assets. Rather the entire organization is interconnected in a six degrees of separation like network of interdependencies. It is therefore essential that the display and communication of dependencies through roadmaps is accurate, timely and complete. This is another reason why roadmapping capabilities should be integrated with the other elements of an organization’s strategic portfolio management approach and software, rather than separate, standalone functionality.

Functional integration

While organizations will use many different types of roadmaps across the enterprise, there must be relationships between them. There must be the ability to drill down from the strategic roadmap to the IT roadmaps, to the macro level product roadmap and to individual products and services, and so on. The roadmapping software must allow for the connection between priorities, investments, capabilities and functionality, and for that journey to be traveled by executives seeking more details, or by frontline workers looking to understand the purpose behind their efforts.


Milestones are important elements of roadmaps at all levels and granularities. They represent key targets and serve as a measurement tool that confirms progress towards longer term goals, or identifies the potential need to adjust plans and strategies.

Milestones combine with the timeline element of roadmaps to allow for the representation of the success criteria for a portfolio, program, project or other element at a certain point. They can also be viewed in combination with dependencies to improve understanding of what must be achieved to deliver each of the milestones, and to assess where barriers to progress are occurring.

Automatic Updates

Roadmaps are intended to be actively managed by individuals – adjusting plans in response to evolving circumstances, changing priorities and new opportunities. But the roadmap tool being used by the organization must also integrate with other enterprise solutions to automatically update performance and completion information on strategic initiatives, changes in IT assets, and so on. This ‘agile roadmap’ ability, driven by automatic updates is key to effective roadmapping.

How to create effective roadmaps

The mechanics of creating a roadmap are easy – or at least they are if you use the right tool (we’ll get to that later). But that doesn’t mean that the process is straightforward. Effective roadmaps are dependent on an organization having clarity in a number of areas:

Let’s consider each of those.

The alignment of strategy and execution

Roadmapping is first and foremost a strategic planning tool. It must be used by the very highest level of the organization to develop and adjust proposed investments in order to successfully execute against strategic priorities. More than that, it must support detailed analysis of those investments. We’ll look at each of these elements in more detail below. But once those strategic plans, and the roadmap that visually represents them, is in place, there must be the development of initiatives to deliver on those strategic priorities.

It is up to department heads, line of business executives, product managers, etc. to develop and adjust their own roadmaps in such a way that the work being delivered, across all structures and each of the tri-modal realities, aligns with those strategic roadmap elements. Planning and work definition must relate back to the strategic and portfolio level roadmaps. Dependencies must support the strategic dependencies while still enabling effective and efficient work execution, resource utilization, and so on.

Organizations must drive strategic portfolio management from the top of the organization through the funding, prioritization and scheduling of work and that process must be reflected in the roadmaps that support the ability to drill down into each priority and investment, journeying from the top planning layer through the funding and delivery work until individual capabilities and functionality are defined – for all asset types, all work methods, and all team structures.

Furthermore, those teams and individuals must be able to journey up through the aligned roadmaps to tie their individual contributions directly to the strategic priorities that those efforts support. That can’t happen with a standalone visualization tool. It requires roadmapping to be an integral part of an organization’s strategic portfolio management and adaptive project management approach.

Continuous and adaptive planning

Strategic planning can no longer be a ‘set it and forget it’ approach. Plans must be constantly reviewed and updated in response to events and circumstances within and beyond the organization. A roadmap allows those changes to be represented graphically with very little effort, but more than that, it also enables continuous planning to be effective and efficient.

Organizations must continuously reassess their decisions around strategic priorities, funding, prioritization, scheduling and execution of all work methods. They must be able to understand how emerging opportunities and new threats are impacting the ability to deliver as well as the appropriateness of previous decisions. But most critical of all, they must be able to understand what’s possible within the confines of previous decisions, and what the impact of changes to those decisions will mean.

That’s where roadmapping becomes a critical planning tool for executives. When completely integrated as part of a strategic portfolio management solution, it becomes a powerful way of considering different options, understanding the impacts of possible decisions and driving improved decision making. Organizational leaders can explore multiple alternatives quickly and easily, rejecting those that will be incapable of supporting business priorities or that can’t be delivered within the confines of existing organizational resources.

This allows them to quickly develop a short list of possible adjustments that can then be subjected to the next level of consideration – something which also happens through roadmapping. That’s the portfolio analysis element that we’re going to look at next.

Portfolio analysis

When a roadmap is an extension of the organizational data leveraged by a strategic portfolio management platform, it becomes not just a powerful planning or communication tool, but also a way to accurately and quickly analyze options and develop recommendations for the most appropriate solutions. Whether it’s the result of continuous and adaptive planning, a response to challenges in investment delivery, or a fundamental shift in organizational priorities, portfolio analysis is critical to ensuring the right decisions are made and implemented in a way that can achieve results.

Using a roadmap, a portfolio manager can easily assess and compare the impacts of different models, adjust models by shifting schedules or priorities, and understand the compromises required to balance what’s needed with what’s possible within the confines of the organization. Additionally, portfolio managers can understand where those limitations exist and feed the strategic resource management tools, funding and investment process, or other related processes to alleviate those bottlenecks.

This level of analysis simply isn’t possible without integration with strategic portfolio management – standalone visualization tools will allow for quick changes to proposed investment plans, but will provide no insight into whether those changes can be delivered. The portfolio is the vehicle that has to deliver strategic change to the organization; roadmapping is the tool that ensures that change is orchestrated in the most effective and efficient manner by allowing rapid, detailed and accurate analysis of options.

Visibility and transparency

Roadmaps have the ability to communicate potentially complex concepts quickly and in a straightforward manner that is easy to understand. But there’s more to communication than simply a pretty diagram and a few buzzwords. The audience receiving that communication has to believe that the information is accurate, up to date and relevant for them. That’s where a roadmap can excel by providing visibility and transparency in a context that is relevant for everyone.

Everyone in organizations today understand that priorities are constantly shifting and evolving. Product management functions expect to have to shift in response to emerging capabilities and competitor actions. Benefits realization software is one way organizations can ensure that every strategic initiative delivers the expected benefits or be subjected to adjustment or cancellation. And at the front line, every worker on every team, regardless of the structure or delivery method of that work, know that there are likely to be adjustments to keep the work being done aligned with business goals.

What each of those individuals and roles needs is to know what those changes are and how they themselves are impacted. That’s what they can have when roadmaps are integrated through common data fueled by both the planning-focused elements of portfolio management and the execution-focused adaptive project management elements.

Changes driven by planning and strategy flow down to technology and product roadmaps. Adjustments to business goals are directly represented in program and project roadmaps and feed work structures and adjustments across all delivery methods. And the reverse is also true. When roadmapping is fully integrated with adaptive project management and strategic portfolio management platforms, variances in work delivery flow up to the more strategic layers, allowing relevant stakeholders to analyze the impacts and consider whether further adjustments are needed across the portfolio to maintain alignment between plans, investments and delivery.

Roadmapping tools & software

There are no shortage of roadmapping tools capable of producing clear, concise, well-presented roadmaps. But that is not where the focus should be when choosing a roadmap tool. Standalone presentation preparation software can produce a roadmap, but that will only ever be a single snapshot in time with no ability to integrate with anything else, nor to effectively drive performance.

Organizations must ensure that their roadmaps are living, evolving things, responding to changes in organizational strategy without requiring excessive amounts of manual changes; and driving those adjustments where appropriate. They must also ensure that performance information is reflected in the roadmap tool, again without the reliance on manual changes.

To achieve this, roadmapping functionality should be viewed as an element of the integrated strategic portfolio management and adaptive project management suite that the organization uses to manage strategic planning and delivery. By integrating roadmapping as a strategic tool with strategic portfolio management, a visual roadmap can be produced directly from those strategic planning activities with just a few simple clicks.

And by integrating that same functionality with the adaptive project management components of the tool, automated updates of performance information can be captured without any manual intervention. That allows executives to focus on leveraging roadmaps for the benefit of the organization – focusing their attention on modeling and analyzing the most appropriate adjustments, supporting the business vision, and so on.

Integrating roadmaps with Strategic Portfolio Management

Producing an effective strategic roadmap, and then aligning other roadmaps with it can go a long way to providing clarity in the strategic planning process, in the management of strategy execution and the communication of strategy to all stakeholders. But roadmapping is just one element of strategic portfolio management. To deliver a sustainably high performing enterprise requires consideration of all the strategic imperatives.

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