Every Leader Needs a Strategic Roadmap: Insights From Scott Klososky; Future Point of View by@andreafrancesb

Every Leader Needs a Strategic Roadmap: Insights From Scott Klososky; Future Point of View

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Annie Brown

Annie Brown is the founder of Lips, a creative sharing platform for women and the LGBTQ community.

When navigators first traversed the globe, charting new territories, and exploring new conquests, what was the most fundamental tool required? A map. Maps guide us through new endeavors, they help direct us as we explore new situations. Maps help successfully lead us to a destination. Similarly, as organizations and leaders navigate new territories and opportunities, a roadmap is an essential tool. 

Today, leaders are navigating their organizations through the rocky landscapes and unfamiliar oceans of digital transformation. The winds of transformation have only escalated with new realities such as remote work. Therefore, this journey is an essential one, because survival now necessitates the quest for the treasures transformation can provide. However, peril awaits leaders and organizations on this journey. A strategic roadmap helps leaders prepare for these perils and adequately avoid them. Those leaders who draw a strategic roadmap fair far better than those who do not.   

“It’s never too late to implement effective strategies,” says Scott Klososky, a Founding Partner at Future Point of View, a boutique business and technology consulting firm who has worked with organizations such as Great Clips and General Motors. “If your team has never done this exercise: do it now. This is one of the most basic ways to protect your profitability, your people, and your future.”

Strategic Roadmaps

A strategic roadmap is a guide from your current state to your desired future state. It helps you define a clear path from the former to the latter and guides you so that you might avoid the pitfalls that await you on this journey. 

Building a strategic roadmap can be distilled down into four components: Identify your dimensions, establish your destinations, create a timeline, and analyze your environment. 

First, prioritizing the dimensions that are important to the business can help leaders chart the necessary destination, as an explorer must identify the commodities critical to her patrons so that she can establish the areas she must encounter to gather the commodities. 

“Every strategy will have unique dimensions and depend on the kind of business you run,” says Klososky.

A business functions on different metrics that are unique to the business. For instance, value drivers prioritize tasks while KPIs measure whether those tasks are working. Dimensions such as data, governance, automation, customers, products, markets, and capital are all components of an integrated strategy. 

Once dimensions have been prioritized, a strategy must be built around them. A destination must be defined for each of these dimensions, as an explorer might have once sought spices in the Orient or new land in the Americas.   


An example of a dimension might be automation. The destination could be to increase revenue per employee to $200k/person. Then you can define the gap between where you are currently and your destination. You can now understand that your processes must improve by 20%. This is a clear metric for which you can now strive. The dimension and destination are now both clearly delineated. The end state has been defined. Success is clearly visible. 

“Without the end in mind, the so-called strategy is really just a series of upgrades that lead nowhere, especially not to fulfilling achievement,” says Klososky. 

Once the dimensions and destinations are clear, it’s vital to create a timeline for sequencing your journey toward success. Gantt charts can be a great tool to build this timeline. Gantt is a common method for managing sprints of activity and organizing tasks. Utilizing a calendared method forces a team to whittle down established steps toward the destination into a series of action items. 

These milestones keep everyone on track and rowing the boat in the same direction. This is essential because navigating to a set destination will be a shared endeavor across the organization.

The final step is analyzing your environment. This step is critical because it impacts everything.

Understanding the market

Businesses with very different operations and goals may articulate similar dimensions and destinations. They might even opt for a similar timeline to achieve what they’re after. Yet their environments might be vastly different.  

The difference between a worldwide fleet management company and a Silicon Valley SaaS start-up is vast. They may both be managing data, people, and resources. However, each has an environment with unique elements that will impact progress in different ways. For example, the luxury brand Godson has done this expertly. Godson found that by carefully examing the luxury environment in which it thrives, it was able to better plan for the future.

This can also be done on the individual brand management level as well. Similarly, business influencers JeffSoFresh and Diego Andres Lozano applied this method to differentiate themselves from competitors. Although JeffSoFresh and Lozano exist in similar markets, they were able to create unique offerings, and therefore unique roadmaps by simply having a deep understanding of their brand's business environment.

In short, the road to transformation will look dramatically different for a social media startup than a global shipping company, although the destination might be similar.  

Beyond the macro-dynamics of the external environment is the internal environment, including culture. 

“This changes the game for the workers behind the scenes who the strategy will impact the most.” Klososky explains, “All strategies exist inside both environments. Minding the environment is akin to creating fertile ground for a strategy to thrive in. This requires leaders to analyze their environment and score the receptivity of the environment to the destination.” 

You must identify the fertility of the ground for transformation to thrive. You could say on a scale of 0-100 the fertility of the ground that your efforts will land in is a 41. The calculations used in this exercise will be industry and company-specific. The best-developed strategy that attempts to thrive in a bad environment will almost always fail. Identifying the fertility of the environment and its receptivity to transformation is a crucial and mostly ignored step.

This identification can help leaders quantify the chances for a successful journey to a destination. Is your ship seaworthy enough? Do you have the right supplies to survive the expedition? Are your sea hands capable enough to navigate the voyage?

No company has been completely immune to the uncertainty caused by the COVID-19 pandemic. Hundreds of thousands of businesses, from small to large, have failed during this challenging period.     

“It’s true what they say, a crisis shows your true colors,” says Klososky. “No one feels like pulling out the map when you’re trying to plug holes in the lifeboat. And yet, abandoning your roadmap in a season of chaos only escalates problems. 

“Do you have to be more dynamic? Absolutely. When I hear leaders say they laid out a strategy in 2020 and then saw it blow up in their faces, I am understanding. However, I do believe that many leaders are out of alignment with their company’s vision, and this exacerbated the challenges caused by the pandemic.”

A roadmap can be a wonderful way to inspire confidence within the organization. It shows that you have a clear destination that everyone can work toward. 

There are some ways you can ensure your roadmap remains steady in shifting seas. 

First, don’t alter the dimensions. Once they have been established, they should remain firm despite changing dynamics.

That doesn’t mean your speed cannot be adjusted with changing conditions. Pace can be altered to recognize current realities. You may speed up or slow down the journey to your destination based on current organizational, economic, and market conditions. 

Regularly reviewing the roadmap is important. Consider a review every 30 days, so that you can adapt your pace based on the current environment. 

Vision casting can help jump-start your roadmap creation. What is your organizational vision for the future?  Do you want to be bigger? More profitable? Have an increased focus on culture?

Vision casting helps you understand in what continent your destination lies. Then you get more granular by choosing a destination. If you want to be bigger, how much bigger? If you want to be better, in what way?

Even as you do this visioning, remember that the entire roadmap—not just the destinations—must be completed and intact for the forward motion to occur.

One of the advantages of roadmaps is that they are versatile in their potential use. Strategy roadmaps can apply both to digital strategies and to overall strategies in general. 

“It’s the right action plan for whatever you’re trying to achieve,” concludes Klososky. 


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