5 Critical Steps You Must Take Before Publishing Your Next Product Roadmap

Hey there, fellow Product Managers! It’s that time of year again for most of us. Sweater weather means budgets and roadmaps are front of mind.

Building your annual product roadmap is a daunting task. Ideas are endless, what makes the cut and what stays in the parking lot? Taking a blank canvas through to Starry Night, while exciting, can also be overwhelming. This is especially true while trying to wrap up the current year’s initiatives.

To ease this burden, we have prepared a comprehensive 5-step guide to help you master the art of organizing your initiatives, crafting your roadmap, and gaining the support of all your product stakeholders.

1. Prioritize and Size Up Initiatives

An initiative is the unit of work within a product roadmap. The to-do’s if you will. Hopefully you already have a list of initiatives in your product management system (as in you are not starting with a block of stickies and a Sharpie or, perhaps worse, an Excel spreadsheet).

Prioritize each initiative based on the impact on your product. We recommend using a 3 or 4 level prioritization strategy. High, medium, and low. Or critical, high, medium, and low.

Also, assign each initiative a size based on the effort, time, and resources you estimate it will take to complete. The most common approach for sizing initiatives is based on t-shirt sizes – extra-small, small, medium, large, and extra-large. These sizes are mapped to rough lengths of time for an average developer on your team: one day through one year. Cute and effective.

Alternately you can use a points system that maps one-to-one to points at the work item / sprint-level. This is a more scientific approach but can be overly cumbersome for early planning exercises. We find that t-shirt sizing is a more practical approach to start with as it is a little more intuitive.

2. Define the Stakeholders of Each Change

A good roadmap includes changes for each of your stakeholders. As you know, the list of stakeholders is LONG. Is it the sales team, hoping for new features to dazzle clients? Your customers, yearning for a new AI feature? The support team, dreaming of a quieter, less chaotic workday? And, don't forget the development team – they would love to knock out some tech debt (yup, we all got it). Striking the right balance between all of these stakeholders is key for getting buy into the roadmap.

To help sell the roadmap, assign each initiative to stakeholders. Then create a summary of changes by stakeholder. Push out some metrics around priorities or sizes of changes by stakeholder. And BAM, you now have buy in across the board.

3. Build Your Roadmap Using the Rock, Sand, Water Framework

Now that you have evaluated your individual initiatives, it is time to start to structure your roadmap. Roadmaps are typically built in a Kanban board structure with initiatives assigned to planned major releases or time frames (monthly, weekly, or quarterly).

Assign your initiatives using the rock, sand, water framework. No, that’s not a quip from Karate Kid – it’s merely a smart order for scheduling your initiatives:

  • Rocks (XL/L): Your rocks are the massive boulders of your roadmap, representing the extra-large- and large-size initiatives. These are the game-changers, the big moves that will significantly shape the future of your product. Think of them as the architectural blueprints that form the backbone of your product's evolution. These need to be started earlier in the year to finish on time.
  • Sand (M): After securing your rocks, it's time to fill in the gaps with sand. The sand represents medium-sized initiatives that can be jockeyed around on the roadmap, fitting nicely between the rocks.
  • Water (S/XS): Finally, dump in the water. These are the small initiatives that can easily be moved around on the roadmap based on resource availability.

Remember, priorities are the key spice in this recipe. The best scheduling tools include boards that show priorities so you can sort initiatives accordingly in your product (and to help with the inevitable rejiggering that will occur down the road.)

4. Tune Your Steve Jobs Aggression Dial

Steve Job’s product roadmap aggression is tuned up to 11. He sets insane milestones and pushes his team to insane levels to try to meet these milestones. The results can be fantastic if you have the right team in place but it might not be the right approach for your specific software team.

Figure out the right approach for your team and plan accordingly when building your roadmap. It's not just about setting milestones; it's about setting achievable ones and motivating your team to meet them.

Here is an inside look at Job's 2010 roadmap sketch...

5. Embrace Murphy's Law

Ah, Murphy's Law - if something can go wrong, it will. It is the reality of the world of product management.

The moment you unveil your 2024 roadmap you can bet that an email from the sales team will arrive, urgently demanding your attention to close a massive deal. That's Murphy's Law in action. And it's an integral part of the business world.

Embrace Murphy’s Law by planning slack time in your product roadmap and adapting to the inevitable changes that will come while you execute. Have a set of “reach” initiatives identified to utilize the slack time if your world (magically) does not catch fire.

So, there you have it, Product Managers. With these five steps, your 2024 roadmap can transform from a daunting task into a well-planned and exciting journey. Happy roadmap crafting!
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