Chapter 11. Strategic Roadmapping
“Map out your future—but do it in pencil. The road ahead is as long as you make it. Make it worth the trip.”
Jon Bon Jovi
“All you need is the plan, the roadmap, and the courage to press on to your destination.”
Earl Nightingale
“A good plan is like a roadmap: it shows the final destination and usually the best way to get there.”
H. Stanley Judd
“I can’t change the direction of the wind, but I can adjust my sails to always reach my destination.”
Jimmy Dean
“Follow what you are genuinely passionate about and let that guide you to your destination.”
Diane Sawyer
“The essence of strategy is choosing what not to do.”
Michael Porter
Have you ever been working with the business and started to realize that a new vision was emerging, one that is radically different from where you are today? A vision that would be a real game changer and, if realized, would have a significant impact on your business, possibly your industry, and maybe even the world?
Your mind begins to swirl with all of the things that would need to happen to make this vision come to life. There are what appear to be endless dependencies that would need to align for this to become a reality. Over the course of weeks and months, you begin sorting this out with the business, and you begin to realize that there is a glimmer of hope that if things aligned reasonably well, the vision has a real shot (albeit a long shot) at becoming a reality.
This chapter unveils one of the essential skills needed by a software architect: the ability to lay out a roadmap for how a potential destination can be reached.
Strategic Roadmapping Defined
Strategic roadmapping is the process of laying out major milestones that are likely to be required for a particular vision to be realized. The exact sequence of the milestones may not be well defined, but their general order is roughly correct.
Roadmaps make strategies actionable.
Representing roadmaps visually can give a sense of the steps, dependencies, and their approximate ordering to achieve a particular vision (see Figure 11.1).
Figure 11.1. Roadmap visualization
Elements of a Strategic Roadmap
Strategic roadmaps tend to incorporate the core elements described in the following sections.
Strategically Focused
The roadmap should be aligned with the strategies, mission, and goals of the organization. There should be an end state toward which the roadmap is driving. Some level of fuzziness in the end state is normal and can be clarified along the way.
Time Sequenced
The roadmap itself should target a specific time horizon. Typically, it can range from six months to 36 months depending on the nature of what is being pursued and how urgent the end result is to the organization.
Organized by Swim Lanes
The swim lanes on the roadmap typically represent groups that will do or oversee the work, strategies being pursued, or some other logical grouping that is highly relevant to the group to which the roadmap is targeted. Within each swim lane, you should include key items that need to be addressed, their approximate start and end dates, and key milestones that need to be achieved to demonstrate that progress is being made.
One useful organization of swim lanes is
• A product swim lane (key capabilities, features, or releases)
• A technology swim lane (key technology deliverables that are dependencies for the product or products)
• An infrastructure swim lane (key third-party and operational dependencies)
Dependency Aware
There are typically many dependencies among the items that are represented on the roadmap. These dependencies need to be clearly called out to help the audience that is consuming the roadmap understand their relative order. The items should be sequenced according to their relative start and end dates in relation to the other activities and dependencies that exist.
Visually Represented
The roadmap is best represented in a visual manner. The use of time spans, sequencing, colors, shapes, symbols, and icons can help make the dense amount of information being presented more consumable and relevant to the audience.
Collaborative in Nature
The development of the roadmap is collaborative in nature. It typically requires input from a wide group of individuals with expertise in varying areas. This collaboration enables dependencies to be identified and key milestones to be established that will need to occur to reach the end goal.
Code Named
The effort that is represented by the roadmap often has a code name associated with it. This naming allows a context for discussions to be established among those involved with the effort. A code name also minimizes information to those who are not familiar with the effort if confidentiality is a concern.
Context Dependent (Personalized)
There is no right way, process, or format for developing a roadmap. The roadmap itself needs to be highly relevant to the organization that is developing it. It needs to use domain-specific names, categories, symbology, colors, goals, and strategies that are common and familiar to your business and industry. You need the roadmap to be easily consumable by a broad audience. The more foreign language and unfamiliar concepts that are introduced into the process, the more challenging it will be for people to understand what is to be accomplished.
Multidisciplinary and Specialized
Most roadmaps go beyond the knowledge and expertise of a single person and often of an organization. Gathering the right set of people who can speak to the nuances of the plan to be pursued is critical to developing a roadmap. If you don’t have all of the expertise that is required within your organization, you may have to bring in external experts or consultants to help speak to the areas that are new or unknown to the organization.
Prioritized
Roadmaps are as much about what you want to exclude as what you want to accomplish. They are about making tough decisions and prioritizing what to include and when it needs to be accomplished. A roadmap is not just a wish list.
Iterative in Nature
Roadmaps are inherently iterative in nature. As the roadmap is socialized to a broader audience, new details, new dependencies, and new risks emerge and some fade away. This updated information needs to be fed back into the roadmap, which leads to its evolutionary and organic nature.
Updated
Roadmaps need to be living documents. The group that owns and develops the roadmap needs to keep it relevant by updating it on a monthly, quarterly, or yearly basis to reflect progress, changes, new dependencies, or changes in sequence. Over time, it can be interesting to see the progression of a roadmap as it evolves. When new versions of the roadmap are created, a date or version identifier should be placed on the roadmap to let those who are consuming the information understand whether it is current or historical in nature.
Published
Roadmaps should be published to a location that allows for them to be consumed and commented on by a sufficiently broad set of people. Access to the roadmap may be limited to those who are directly involved with the effort or those who are relatively close to it due to confidentiality or strategic concerns. The goal is to engage the broadest possible set of individuals who can provide appropriate feedback. Because of their strategic nature, most roadmaps are not publicly available.
Measurable
Progress on execution of the roadmap should be clearly measurable. The steps that are identified in the progression toward the end state need to be small enough that a regular heartbeat of progress is visible to all who are involved with the effort.
The elements of a strategic roadmap can be used to give you a sense of how to approach roadmapping.
Roadmapping Strategies
Whiteboarding the Roadmap Using Sticky Notes
When you start to develop a roadmap, keeping it simple and minimizing the ceremony around its creation can help get things jump-started and moving quickly. One of the best ways to approach this is to simply use a large whiteboard and place sticky notes on it where you’ve written things that need to happen to achieve the goal. Sticky notes can easily be moved and sequenced relative to one another.
As this roadmap develops, natural sequences and groupings will begin to form. This helps inform what the swim lanes for the effort should be. As dependencies are discovered, note them on sticky notes or use tape and string to connect them. As you make progress, take pictures of the roadmap. Later, this can help trigger ideas from others as they see the roadmap developing.
Starting with the End (aka Work Backward)
Sometimes just getting started with a roadmap can be a bit daunting. One way to alleviate this is to start at the end. Ask what is needed to accomplish the end state. Once those items have been identified, repeat the process with these new items as goals and determine what needs to be in place to be able to accomplish them. Keep repeating this process until you are back to your current state. This process will help identify key dependencies and potential gaps that need to be considered.
Holding Workshops
Given the collaborative nature of roadmapping, holding workshops where all the relevant participants can meet in person is a great way to get a strategic roadmap kicked off and align participants. It allows for the participants who may not have worked together in the past to get to know one another. In the future, this will help reduce the barriers for people to share ideas if they have a sense of trust and an established relationship with the other participants.
Before the workshop, give the participants information about what the agenda will be and access to any preparatory materials so that the time together can be less about discovery and more about the actual roadmap development and conflict resolution.
As the workshop progresses, capture any actions that evolve out of the discussions. When the workshop is nearing the end, review the action items that are outstanding and relevant, and capture information about what went well and what could be improved about the workshop.
Thinking of Roadmapping as a Project
One way to help with the sustainability of the roadmap is to consider the roadmapping exercise as a project itself. The roadmap is the product and the work that happens surrounding the roadmap can be thought of in terms of stories, iterations, release planning, and other development steps.
Capturing Underlying Guiding Principles
As the development of the roadmap progresses, often guiding principles are established to help the participants make decisions. Capturing these guiding principles can help others later on to understand why one decision or path was chosen over another. They help describe the overall rationale behind the roadmap.
The strategies for strategic roadmapping are only suggestions. As stated previously, there is no right or wrong way to develop a roadmap. The key is to discover the information that is needed to pursue the goals that the organization finds most desirable and to do it in a manner that fits with the organization’s culture.
Roadmapping Principles
The goal of roadmapping is to establish a path to reach a specific set of goals. The following principles can be used to help guide the creation and maintenance of the roadmap.
Keep It Simple
Roadmapping should be done with as little ceremony as possible. Find quick and relevant ways to express your ideas to those who will consume the roadmap, use low-tech mechanisms to gather the roadmap information, and minimize any title or role recognition within the roadmap-building workshops. The goal is to get to the task at hand and keep those participating in the roadmapping effort as engaged as possible so they can make significant contributions.
Partner with the Business
Partnering with the business is essential for any roadmapping exercise. You may be able to lay out architecturally what needs to happen, but without input from the business, you will likely not be aligned with its direction and vision. In practice, this is the only way you will achieve the funding levels that are needed to deliver the vision. (For more information, refer to Chapter 1, “Partnership.”)
Get Moving
Sometimes looking at a roadmap can seem a bit overwhelming because of everything that needs to be accomplished. One of the best ways to alleviate this is to just get started.
Usually, once you start moving, your anxiety tends to go away and the job at hand keeps you focused. Once you start making progress, there is a tremendous amount of satisfaction that you are moving toward a better state, and it will add energy to what you are doing.
Have Fun
Have some fun along the way. Life is short. If you don’t enjoy what you are doing, look for ways to make it more interesting. Maybe look for ways to partner with others. Usually, traveling along with others tends to make the work seem less like work, and the fun can begin.
If you can’t find any ways to make it interesting, look for something else to do and come back to it later. Sometimes the work can’t be made interesting, and you just need to put your nose to the grindstone and get it done.
Strategies without Goals Are Pointless
Sometimes roadmapping exercises start with strategies in mind, but without a clear goal of what the destination is. Be cautious when this occurs. You need to have a vision and a clear set of goals in place to begin mapping out how to get there. If these are not well understood, take time to back up and get this information clarified or raise your concerns about the endeavor. There needs to be a “why” and a “where” before there can be a “what” and a “how.”
Identify Areas That Require Research and Innovation
If you encounter a great chasm during roadmapping development and there is no logical path to the next step, the goal being pursued may be more research or innovation oriented. If this is the case, a focused research or innovation effort may be needed. (For more information, refer to Chapter 10, “Technology Innovation.”)
Identify Skill and Knowledge Gaps
During the course of roadmapping, as dependencies are identified, it usually becomes clear what skills and knowledge the organization lacks. This information can be used to help determine training needs, hiring needs, or consultant opportunities. The key is to identify these areas early enough that you can remedy them before they block the progress of the roadmap.
Be Flexible on the Timing of Getting to the Destination
Sometimes the deadlines that we drive toward are simply self-imposed.
If you and the business can be flexible about when something must be done, you have the opportunity to do things at the right time versus forcing something that is really not ready to be addressed. Sometimes if you wait, other solutions will appear or new approaches may come to light that make achieving what you want much simpler.
Be Willing to Take a New Route
A roadmap is an approximate plan for how to accomplish a particular goal or set of goals. The challenge is that with most roadmaps a significant number of unknowns and challenges lie between where you are and where you want to go.
Occasionally, when you are traveling down the road toward your goal, roadblocks appear. There are several choices at this point:
• Do you barge forward in the direction you are traveling? You may already have a significant amount invested, and you feel you are close to a solution.
• Are you willing to time-box how much time you are willing to invest in continuing on the current path? This will allow you to limit the collateral damage and get moving toward a different solution.
• What other choices are “in the vicinity”? There are often adjacent solutions that may not be exactly what you had originally planned but are close enough that you can move forward without significant cost or delay.
• Do you need to back up and take a fresh look at what you are attempting to do? Do you really need to do it? Are there other avenues that still get you to your end goal but allow you to go around versus through the current roadblock? Stepping back and taking a broader view of a roadblock can often give you ideas about how to approach the goal.
Taking the time to step back and clearly consider what your best alternatives to moving forward are can help keep you moving toward your ultimate goals in an effective manner.
It’s Not about the Details; Focus on the Destination and Key Milestones
For nearly any end-state vision, there are many, many different paths to achieving the goal. The details involved in getting there are often not as important as simply getting there. There may be major milestones that are essential to hitting the end-state target.
The key is to focus on the destination and be willing to vary how you are going to achieve the goal. Sometimes simply changing the approach can have a dramatic impact on the overall cost and effort required to achieve what you want.
Some of the best ways to do this are to
• Talk to other architects. They may be able to tell you how they have approached similar problems.
• Talk to other areas of the business. This will help you get a sense of the different perspectives on the problem you are attempting to address.
• Talk to some of the executives. They usually have a remarkably good sense of what is essential and what is nonessential.
• Talk to some customers. Customers who work in the area you are focusing on can normally tell you if what you are concerned about has any relevance to what they do.
In nearly all situations, talking to others (collaborating) can help
• Clarify what you are concerned about
• Provide alternative approaches or solutions
• Simplify or eliminate problems altogether
• Confirm that you do indeed have a tough issue
Regardless of the feedback, you will have confirmation that you are on the right path or need to make some adjustments.
Follow What Energizes You
If the roadmap that you have developed doesn’t energize you, you are likely on the wrong path or have a vision that doesn’t fit the current business (or strategic) environment. Even if you are on the right path, if you don’t have passion about the goals and vision you are attempting to move toward, you are unlikely to inspire anyone else to want to take the trip.
The key to finding what energizes you is to follow what you are passionate about. Look at what you are trying to accomplish and try to determine the answers to these questions:
• What is of interest to you? These areas of interest will be easy to go after even when you are tired and have been on the journey for a while.
• What is not of interest to you? These are the energy drains. If you do not have interest in doing these things, consider alternatives.
• Are there ways to repackage the item to make it interesting?
• Can you change the approach?
• Can you delegate this area?
• Are there ways to simply eliminate the item altogether?
At the end of the day, you need to believe in what you are doing. If you don’t, you are not likely to succeed, which is bad for you and for the delivery of the roadmap goals.
What Is an Architect’s Role in Roadmapping?
Given the collaborative and multidisciplinary nature of roadmaps, architects are rarely the only ones at the table. Architects normally excel at roadmapping due to their detailed product, technology, and infrastructure knowledge. This detailed knowledge lends itself to knowing and understanding key dependencies that exist, which in turn leads to helping sequence the major milestones. It is common for architects to help draft the first copies of the roadmap.
Where Can You Use Roadmaps?
Roadmaps can be used to describe many different things. It really depends on what you want to communicate about future plans.
Roadmaps can be used for
• Capital planning
• Product or platform capabilities
• Project or product integrations
• Compliance milestones
• Major release milestones
Use roadmaps as a communication vehicle to help others understand the direction where things are going and the general timing of when the goal will be delivered. This will help others plan when they can leverage the solutions identified in the roadmap.
Roadmap Considerations
“You’ll learn more about a road by traveling it than by consulting all the maps in the world.”
Anonymous
“Experience, travel—these are as education in themselves.”
Euripides
As you go through the process of developing a roadmap, there are a large number of considerations that should be taken into account, such as the following:
• Does the roadmap show a replatformization? Key migrations? Major technology changes? These are all large cost drivers that you will need to have accounted for.
• Does the roadmap align with your technology innovation efforts? If it does, it may allow for some natural synergies.
• Does the roadmap drive you toward the revenue model you want to achieve? Does it give you the premium or value brand you are shooting for? Understanding the revenue and value impacts is critical when seeking approval and funding for implementing the roadmap.
• What are your competitors doing? Can you create a likely roadmap for them? Trying to get a sense of what your competitors are doing and are likely to do will give you a sense of how you will need to compete and what issues you may need to address in your roadmap.
• Have others published their roadmaps at conferences? Any external information that you can gather will help you understand how others are approaching similar problems or give you insights into your competition.
• Have others in your company released a roadmap? If they are integrating with you or you with them, do you show up on their roadmap? If not, why not? Creating synergies and following successful patterns can help simplify your justification for implementing the items on your roadmap.
• Does your roadmap vary per platform (mobile versus desktop versus cloud based)? Understanding how platforms impact the work you do can help you structure the architecture in a manner that is platform friendly or agnostic depending on the nature of what you are doing.
• Are there regulatory concerns that need to be addressed? Regulatory needs and requirements can add significant cost to the work of implementing a roadmap. You need to understand these early on and clearly articulate how you are addressing them.
• Are there certifications that are being pursued? Are there dependencies between the certifications? Are there pre-evaluations that need to be performed? Certification dependencies for a roadmap are very important to know up front so that you can include the requirements and costs of pursuing certifications clearly in your roadmap.
Roadmaps are rarely derailed by the known items. It is the unknowns that creep up and derail the effort. Keep a vigilant eye on the roadmap and its adjacencies. This knowledge may give you insights into risks of which you were previously unaware, and it can help give you the maximum amount of time possible to mitigate these risks.
Roadmap Socialization
Roadmapping is an essential communication tool for an architect. It allows for a malleable future, one that is not set in stone but instead gives a sense of priorities and a sense of key dependencies to help inform current decisions.
It can also be used as a tool for others to understand when to engage with a new platform or to understand when their dependencies may need to change.
Once the roadmap has been established, it needs to be socialized within the organization (see Figure 11.2); this will help establish buy-in for the chosen direction.
Figure 11.2. Socializing your roadmap can help align the expectations of all the groups with which you interact, allow for clarifications, and allow for adjustments to be made.
The roadmap can act as a form of sales tool to show that you are aware of certain deficiencies today, to show alternative ways to address them in the future, and to show approximately the time frame in which they may be addressed.
The key is that a roadmap invites conversation and a way to gather other people’s insights (positive or negative).
It is likely that some of the roadmap may not be definitive. Socializing it invites the kind of feedback you are looking for:
• Are we directionally correct? There is a natural tension between directionally correct and the need for course correction based on different perspectives.
• Does it invite excitement and passion? If it does, you are probably on the right track.
• Does it invite skepticism? This may be okay, although you may have a challenge on your hands to work through it.
Managing group dynamics during roadmap development is critical to keeping the flow of information and critical thinking open and respectful. When a respectful environment exists, people are more naturally willing to express their true thoughts.
A roadmap really is a communication tool. It’s a plan. It’s okay for it to change as new things are learned. It also gives you a sense of history when you look back and see what you were thinking and where you actually ended up.
Celebrating Milestones Achieved
Once the roadmap has been established and the project or projects that support it are well under way, take the time to celebrate the milestones as they are achieved.
Recognizing that you are making progress on the road to success can keep the teams engaged and provide valuable feedback about where you have been, what lessons you have learned, and what you need to continue doing to ensure that you will complete the journey.
Summary
The path to roadmapping begins with
• Understanding the elements of roadmapping
• Leveraging the roadmapping strategies
• Understanding the roadmapping principles
• Knowing where roadmaps are best used
• Being observant of new risks
• Socializing the roadmap
• Knowing your role in roadmap development
• Celebrating milestone successes
For architects, roadmaps are an essential communication tool for helping to establish a vision of what needs to be accomplished and its approximate sequencing. When the business and architecture are on the same page regarding where a product or platform is going, this partnership can help propel the success of the business.
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