The Secret to Building Fast Roadmaps

The Secret to Building Fast Roadmaps

In digital project management, it can be easy to overcomplicate the entire process of creating a roadmap. I’ve spent hours connecting dots, structuring dependencies, balancing team members' workloads, and creating milestones. It seemed like a monumental task that took away time from everything else I needed to do.

Sound Familiar?

The worst part about this lengthy process was that I found myself in a position where my entire roadmap needed to be reworked a few days before the first milestone was completed.


Before we begin, let's define a few terms.

  • Milestone: A turning point or progression marker in a project's development.

  • Dependency: Something that must be present for another element to be fulfilled. These can involve task relationships, unresolved decisions, or missing information.

  • Roadmap: A series of tasks over a timeline that are needed to reach the end goal of a project.


Recently, a friend asked for my assistance in tackling a roadmap that had been giving them difficulty for the past week. It's a familiar situation – tasks keep piling on, and suddenly allocating time for planning becomes almost impossible. As a result, you find yourself behind schedule before the project even starts – frustrating!

After a few hours, we had the project back on track. It's incredible how much precision and attention to detail go into the planning processes – we need effective plans, but it's important to remember that roadmaps should be fast. If you find yourself spending more than one day crafting your roadmap, you may be overcomplicating it.

After managing numerous projects, I have learned a few tricks that can come in handy. Even if the techniques differ from the classical approaches, rest assured that these tips should benefit those who try them – so give them a chance and let me know if you find them helpful!


Roadmaps should be living documents.

The reality of projects is that timelines and roadmaps inevitably shift and evolve, so it's essential to make room for change. To keep up with such changes, treat roadmap restructuring as a regular feature of your task lists – something to be done before each milestone is started. This way, the periodic reworks become part of the expected process, and you remain better prepared for whatever comes next.


What needs to be done is very different from who needs to do what.

A roadmap is a systematic approach to distributing deliverables over time. Assignment delegation is balancing the allocation of deliverables across your team. Planning and delegation can be challenging on their own, but the task becomes even more daunting when you amalgamate them. Focus on the task at hand, and never assume you have (or don’t have) the resources to do what is required.


Don’t stress dependencies.

Dependencies can be overwhelming, and letting them take over the entire project is easy. However, I've found that more often than not, those unexpected issues are a sign that it's time to re-evaluate the roadmap – whether you're finishing a milestone or starting a new one. Use dependency escalations as an opportunity to restructure your roadmap and adjust future milestones so that they are achievable.


Prioritization is always about visible traction.

Prioritizing tasks for maximum efficiency is an area of debate, as there's no one-size-fits-all answer. However, if your goal is to make tangible progress as quickly as possible, then the "right" approach is one where you can identify visible traction and let your team respond. Start with what is easiest and get the wheels moving – that way, you'll be able to move forward together and take on more difficult tasks in a timely fashion.


If you don’t know, you know.

When you don't know what the answer is, trust in the collective wisdom of your team. Don't hesitate to voice an "I don't know" – it's an incredibly valuable asset when seeking solutions. Put any unknowns at the end of your roadmap and keep revisiting them with each revision – eventually, you should find that even these seemingly difficult problems can be solved without relying on conscious effort alone. 

Extra Credit

Guy Claxton's acclaimed book "Hare Brain, Tortoise Mind: Why Intelligence Increases When You Think Less" offers insightful perspectives on the phenomenon of unconscious problem-solving. The book delves into how intuitive thinking and taking a step back from conscious effort can lead to extraordinary breakthroughs.

Crafting an effective roadmap doesn't have to be a superpower. With the right approach, it can become a powerful tool for navigating the unpredictability of any project, welcoming surprising turns and unforeseen surprises with open arms. It all begins with streamlining the process and having the courage to start over if needed.

Your input is always appreciated. If this article resonates with you or sparks a disagreement, feel free to leave your thoughts in the comments below. Thank you for reading.

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