Strategic Roadmap Planning

By Kevin Lyons
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About the Author

Kevin Lyons

Kevin Lyons

Kevin Lyons serves as BlueSky's Chief Strategy Officer. Kevin is a growth-minded executive who overcomes complex business challenges by matching customer unmet needs and team member strengths. Kevin uses innovative solutions, based on solid judgement, strong work ethic, and integrity to provide strategic consulting to our clients.
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Strategic Roadmap Planning

A Drop Of Water Can Move An Ocean

Many business leaders I interact with, especially in small or medium organizations, realize more than ever that change is necessary. They know taking the time to plan to meet that change is important. So, why don’t they? Usually, it is due to a lack of time and resources mixed with an abundance of fear. Making changes to their business or technical environment can create a ripple effect across the organization. If they implement a change without thinking through the implications, it could create problems for their business’s operations. It could also introduce security and regulatory weaknesses. And even if the team addresses these risks, the change itself could be disruptive. It is for these very reasons that creating and implementing a strategic business and technical roadmap is critical.

Strategic roadmap planning

Roadmap Creation: A Three-Pronged Attack

The key to successful strategic planning and building your roadmap comes from a strong customer journey map, as we should always start with the customer in everything we undertake in the organization.  The results of this lead to a three-pronged approach that includes:

  1. Innovation – this comes from several sources including customers, employees, process work, industry, market, or competition.
  2. Infrastructure – these usually include company-mandated capital projects that feed all customer-facing or user-facing technologies and processes.  These may be things like ERP, New Physical Building projects, telephony, or communications.
  3. Performance – what falls into this category typically includes those things that are not usually the “sexy or cool” projects to work on, but are incremental changes that can mean a lot to your business.

It is the combination of these that fill out the majority, if not the entire, roadmap planning to support your strategy.

Strategic roadmap planning

A 360 Path to Successful Strategy

At BlueSky, we feel we differentiate with our 360 Approach because we look at your entire business when it comes to building your strategy and supporting roadmap.  We think of execution the entire time we are creating that plan with you to maximize success.  Using the Malcolm Baldrige Criteria to Performance Excellence, we cover all aspects of your company.  We start at the very beginning with your Organization’s profile centered around your Mission, Vision, and Values (and Purpose for those that subscribe to this).  We take a hard look at how Leadership drives the organization, develops and implements strategy centered around your Customers, Workforce, and Operations driven by Measurement that leads to Results.  When it comes to strategic planning we look at how your team is involved today, whether it is tops down or bottoms up, to establish a baseline and drive toward a blended way of planning.  We feel this takes your current culture into account and works toward building from there.

The Two Phases of Strategic Planning

Leveraging our 360 approach, we break up Strategic Planning into two major phases with components that guide your organization through each.  The ROADMAP PHASE and the EXECUTION phase are equally important and one cannot exist without the other.

Roadmap Phase

Burning Platform – Why are we even coming up with a strategy (or new one) to begin with?  This can be driven by intrinsic or extrinsic factors.

Diverging – Breaking your organization into smaller parts (operating units, departments, etc.) to go off and do their own planning or wish list of initiatives to support the plan is critical to ensure all voices are considered.

Prioritizing (Part One) – That smaller group must force rank their initiatives by using a simple method of Value Targeting based on level of value to the organization and level of difficulty to implement.

Converging – Here you get all the smaller groups back together to provide a read out of their prioritized lists and then plot them all on a master planner.    

Prioritizing (Part Two) – Once all projects are listed out in order of priority by each group, the hard work begins to balance all priorities against resources and return.  This time to return (or estimated time to payback) can be based on both your annual and long term strategy.

Platform Building – After all of these steps are completed, you can begin to put hard ink on these plans to get to more detailed level estimates for resources, return.  Doing so means considering your current development operations model to appropriately place them on the strategic plan.

Strategic roadmap planning
Strategic roadmap planning

Execution Phase

Feedback – The final draft of the strategic plan and roadmap requires a litmus test to those closer to getting the work behind the strategy done.

Consensus – After all inputs are considered on the plan, communication is critical to ensure everyone is moving toward the overall objective.

Goal Development – Transitioning from an event planning part of the strategy to living it every day is building real SMART (Specific, Measurable, Actionable, Realistic, and Timebound) goals that should be reviewed in your performance management rhythm.

Resourcing – It takes people, time, and money to get the plan done.  This is the time to coordinate your operating plan, finances, and organizational structure in place.

CAPs – Company Action Plans follow to keep track of open items needed to achieve the steps in the strategy.

DAPs – From the Company Action Plans, you must develop Department Action Plans that specify the who, what, when, where and how you will get the work done.

Strategic roadmap planning

BlueSky uses other factors when mapping out your business strategy. These considerations include Seasonality in your business, your organizational structure, and current mandates or extrinsic demands on time to return for any project or initiative.


When it comes down to why all this really matters, we can summarize it into three things:

  1. Setting The Stage – There must be a reason for creating change
  2. Aligning The Team – There must be buy-in to achieve your goals
  3. Painting The Vision – There must an aspiration to rally the team around future success

This all plays into a true Digital Transformation Strategy that not only can you share internally within the organization, but externally as well.  If this sounds like just the kind of future you need for your organization, reach out to BlueSky and let’s start a conversation using our 360 Approach today. 

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BlueSky’s unmatched commerce expertise allows us to help our clients understand how to utilize omnichannel and business solutions to reach, attract, engage, and grow customers.

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