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  • Writer's picturebethany waldman

Why are Technology Road Mapping Exercises So Hard?

I find that when I ask clients if they have a good roadmap they often have one of two answers.

1. They have a great roadmap for the next 3 months and then some big ideas in the backlog.

2. They have a general idea of what they are working towards but nothing really set in stone.

This is somewhat surprising to me for a couple of reasons. The first and foremost being that I truly believe in building a roadmap helps with success planning and what success looks like. But also The nature of plans is that they will change as other factors, internal and external, come into play. Your roadmap may change, but it’s still guiding the organization forward and keeping everyone united in common goals.

So what are some of the biggest issues I’ve seen with creating and utilizing a roadmap?


I hear often that a company is too busy putting out fires to be able to deal with roadmapping. Or that an organization is agile, so they don't need a larger roadmap. It usually doesn’t work out for organizations with this kind of thinking.

Roadmapping can be scary because it involves predicting the future, an inherently uncertain endeavor. With the rate of technological change and the potential impact of new technologies, accurate predictions can be challenging. All the more reason to be willing to adapt, change, and reroute when new information comes up.

Proper roadmapping requires the adaptability for change. For example, an organization may choose to schedule all its people at 80% capacity instead of 100%. This allows for occasions where people get sick, delays happen, or external factors may derail work. Making sure your business has identified where uncertainties or risks lie will allow for more flexibility and better planning.

When a customer tells me they don’t have a roadmap because they are constantly putting out “fires,” it means their leadership is not prioritizing goals. Indecisiveness and a lack of unity within the company leads to small problems taking priority over big goals.

Organizational Alignment

A well-executed technology roadmap will require input from a variety of stakeholders, including technical experts, business leaders, and customers. Ensuring that all stakeholders are aligned and working towards the same goals can be a significant challenge. Be willing to compromise, and have patience. You’ll a

ll get through this together!


Technologies are often complex and interconnected, making it challenging to understand the implications of changes in one area on other teams and systems. Taking the time to understand your current technology and anticipating potential side effects of big change will save you some headaches down the road.

Resource Constraints

Roadmapping requires significant resources, including time, expertise, and data. Organizations may lack the resources to conduct a thorough analysis, or the necessary data may not be available. Allocating enough resources will be critical prior to roadmapping to avoid serious delays and derailments.

Changing Market Conditions

The market conditions and competitive landscape can shift quickly, making it difficult to predict the impact of technological changes accurately. Regroup with key stakeholders and assess how best to move forward in a shifting arena. Big changes may be required, or only a slight adjustment to allocated resources. You’ll only know after you and your teams assess and align together.


So you’ve completed your technology roadmap! What now? Communicating the findings of a technology roadmap can be tricky, as the information may be complex and technical in nature. Share the information in a way that is accessible and understandable to all stakeholders. Be patient with team members, and be open to finding different ways to communicate information.

Technology roadmaps can be daunting, but with flexibility, understanding, patience, and grit, your company will be on its way to a brighter—and more technologically sound—future!

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