Building a roadmap to communicate the safe landing of your departmental objectives

Does your team have a strategy? Are they able to understand the team vision? Can they articulate how your strategy enables that vision? Probably not.

Hi, I’m Peter Nichol, Data Science CIO.

Today we’re going to talk about roadmaps. Three main components make up a solid roadmap: All roadmaps begin with clear objectives. First, we have objectives to answer the question about what we’re trying to accomplish. Second, are measures. The measures evaluate how effective we were in achieving those objectives. Lastly, there is the timing. Timing addresses when all these objectives and measures will be completed or at a point where we can take a snapshot for evaluation and reflection. These are the building blocks of a roadmap. We’ll go into more detail shortly.

Do you have a strategic departmental roadmap?

You might be thinking, well, of course, we have a roadmap. This could be a formalized document, an idea map, or a task you had wanted to achieve but never got around to completing. This is where our challenges as leaders start. Today, if you approached a person on your team and asked if they could explain your three strategic goals for the year, what would happen? In most cases, you’ll hear elements of where you wanted to go, but it won’t be formulated with the same depth and detail that you had envisioned.

Many strategies are defined, but few are communicated effectively.

This challenge grows as our team sizes and departmental size expands. If your team is not 5 or 10 people and closer to 500 or 1000s, it’s pretty evident that those individuals don’t understand your strategy.

Why is this relevant to us as leaders and executives? Team members that don’t understand the strategy can’t support or encourage others to align to it. There is no shared mission. There is no shared purpose. Establishing a shared mission and shared purpose is key to ensuring leaders can efficiently deliver their objectives.

How do you start building a roadmap?

Start with the mission. What are we trying to accomplish? On the left-hand side of the below illustrations, we define the three biggest priorities. You can think of these as themes or our burning imperatives. Essentially, these are the top three ideas that we as a team will target to accomplish more broadly. Next are the capabilities which we’re going to enable. You can think of these as categories. And essentially, we’re trying to identify the key categories where we’ll place the more energy. Typically, I have twelve major categories that I hyper-focus on over a three-year vision. Next are the objectives. The objective more would consider general goals.

Then we add in our timeline. Typically, I use a three-year horizon and quarterly intervals and only focus on two goals per quarter. I have found that teams are unable to keep the goals quarter-over-quarter straight if more than two goals a quarter are introduced. The result is that using more goals increases confusion.

Building your roadmap

To recap, Q1/Q2 has a single goal, and Q3/Q4 has a single goal. That’s it. It’s that simple. We keep this model simply because it maintains a singular on specific objectives, which we can measure and achieve.

The first page of our roadmap is our “strategy on a page” or our “one-pager” strategy. This is where we define the mission, themes, and capabilities. We also elaborate on the objectives, measures, and timing. This roadmap serves as a guide for resources inside and outside the department. A documented roadmap offers a clear vision of where we’re heading, what we’re trying to accomplish, and how we’re going to measure our success.

Do I only use a one-pager strategy? Not all the time. Often you need to elaborate and explain those themes and how key results will be measured. If you need vital results or the OKRs to be measured, you will need additional supporting detail. You’ll need to use your judgment if your organization requires this greater level of detail. Assuming further detail is needed, you’ll probably a second page to elaborate and expand on your one-pager strategy. But, again, this extra step isn’t always necessary.

Here is an example of a one-pager roadmap and the supplemental detailed strategy. The second page only elaborates on the first theme, but is representative of what the other themes elaborated would look like.

Illustration 1.0 – Roadmap Page 1

Illustration 2.0 – Roadmap Page 2

As you begin your roadmap journey, focus on the top three most important things, mission, themes, and capabilities. If you can make the team internalize the simple concepts of the mission and roadmap, you’re doing great. You’ve already gotten a win, and you’ve established a shared priority and a shared mission. Roadmaps often are used as a replacement for discussions, conversations, or even meetings. Use your roadmap to facilitate and centralize these conversations, not avoid them. A well-thought-out roadmap will establish a shared vision for your team. It’s amazing what happens when an entire team is pulling in the same direction!

Do you have more questions on building your roadmap? No problem. Please send me an email, and I’m happy to share more roadmap concepts with you.

If you found this video helpful, that’s great! Check out my books, Think Lead Disrupt and Leading with Value. They just came out early in 2021 and are available on Amazon and at for author signed copies!

Hi, I’m Peter Nichol, Data Science CIO. Have a great day!

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Peter is a technology executive with 19 years of experience, dedicated to driving innovation, digital transformation, leadership, and data in business. He helps organizations connect strategy to execution to maximize company performance. He has been recognized for Digital Innovation by CIO 100, MIT Sloan, Computerworld, and the Project Management Institute. As Managing Director at OROCA Innovations, Peter leads the CXO advisory services practice, driving digital strategies. Peter was honored as an MIT Sloan CIO Leadership Award Finalist in 2015 and is a regular contributor to on innovation. Peter has led businesses through complex changes, including the adoption of data-first approaches for portfolio management, lean six sigma for operational excellence, departmental transformations, process improvements, maximizing team performance, designing new IT operating models, digitizing platforms, leading large-scale mission-critical technology deployments, product management, agile methodologies, and building high-performance teams. As Chief Information Officer, Peter was responsible for Connecticut’s Health Insurance Exchange’s (HIX) industry-leading digital platform transforming consumerism and retail oriented services for the health insurance industry. Peter championed the Connecticut marketplace digital implementation with a transformational cloud-based SaaS platform and mobile application recognized as a 2014 PMI Project of the Year Award finalist, CIO 100, and awards for best digital services, API, and platform. He also received a lifetime achievement award for leadership and digital transformation, honored as a 2016 Computerworld Premier 100 IT Leader. Peter is the author of Learning Intelligence: Expand Thinking. Absorb Alternative. Unlock Possibilities (2017), which Marshall Goldsmith, author of the New York Times No. 1 bestseller Triggers, calls "a must-read for any leader wanting to compete in the innovation-powered landscape of today." Peter also authored The Power of Blockchain for Healthcare: How Blockchain Will Ignite The Future of Healthcare (2017), the first book to explore the vast opportunities for blockchain to transform the patient experience. Peter has a B.S. in C.I.S from Bentley University and an MBA from Quinnipiac University, where he graduated Summa Cum Laude. He earned his PMP® in 2001 and is a certified Six Sigma Master Black Belt, Masters in Business Relationship Management (MBRM) and Certified Scrum Master. As a Commercial Rated Aviation Pilot and Master Scuba Diver, Peter understands first hand, how to anticipate change and lead boldly.