A Lightweight Product Roadmapping Process
Works with your team’s natural rhythm, and give the organization what it needs to succeed
Building roadmaps is hard. Keeping them up to date is even harder.
Any business with multiple cross-functional teams and growing discipline functions understand this.
As organizational units expand, cultures and processes morph to the needs of the smaller units. This works until the complexity of dependencies creeps in.
Dependencies sneak up on you like a crouching tiger. Just when you think you have things figured out and running smoothly, the dependency tiger pounces and your release gets delayed or worse your features don’t function in front of the customer.
Keeping up with all product work across teams and avoiding the jaws of the tiger takes artful navigation. Teams communicate and work at different cadences. You can try to execute standardize frameworks like SAFe or DAD, but the reality is that synchronizing value delivery alignment perfectly causes undue stress on your product teams.
In general, the larger the organization, the more structure required, but it is possible to implement a lightweight structure, even in large organizations.
Keeping things simple eases stress, works with the team’s natural rhythm, and gives the broader organization what it needs to succeed.
What doesn’t work
I’ll share more about how to do this, but before we jump into that, let me first suggest three things I’ve observed that don’t work and are wasteful.
It’s easy to see why people love this. It fits in a nice box. One a quarter we plan, easy. Done, everyone plans at the same time. No distractions. Just think of all the things that you need to get done to meet the business goals in the next quarter, write them down, share those plans with other teams, and you are off to the races.
Here is the challenge. The business doesn’t stop. Support tickets still come in. The sales team needs questions answered and demos shared. Meanwhile, leadership is still refining what goals make sense right now for some part of the business. The market is dynamic and strategy evolves. It’s hard to stop and plan with a high level of confidence.
As You Like It Planning
Again, sounds wonderful. Give teams the autonomy, authority, accountability, and authority to plan and execute as they see fit. Team’s love this. Until the leaders in the organization have no clue what everyone is working on. Crouching tiger, welcome the hidden dragon.
The fully autonomous teams now find themselves constantly being called into executive reviews to “share” their roadmap. Makes sense, but the burden for these autonomous teams is that they now have to spend time catering their plans for the most demanding executive. Teams waste time and energy re-producing information. A lot.
Meanwhile, the executives are frustrated too. After all, they are constantly in these meetings trying to piece together what’s happening. They can’t see what’s going on across teams in a consistent way.
The Tool Solves it Planning
What happens when teams get frustrated from the above two situations. You guessed it. We need a tool! Perfect.
Now teams and leaders in their frustration rush off to find the perfect solution to their planning woes. They do a little research. Put RFP’s for a variety of vendors. Kick the tires on a few solutions. Pick a tool.
People get excited. Everyone loads up their data in the tool. They step back to look at their masterpiece. They run a report and pat themselves on the back. Problem solved. Then, slowly but surely the data atrophies and teams go back to “as you like it” or “quarterly” planning again. And you are right back where you started.
What to do Instead
Now that we’ve seen some wasteful ways to plan, how should you think about planning? The answer is to start with first principles.
A roadmap is an intention. It is a living document that is used to communicate intent to teams and leadership. It is not a prescription. Roadmaps evolve. They are about confidence and not commitment. They are not static and must be amenable to change.
Starting from first principles helps you establish a foundation for shared understanding. They are starting a point to build on and from.
Your Roadmap and Roadmapping Process is a Product
Think of your roadmap as a product. The customers of the roadmap are your teams, leaders, and other stakeholders.
After considering first principles, you can benefit by doing some discovery with your customers.
Spend time interviewing them to better understand their needs. Ask questions like:
- Tell me about the last time you referenced a roadmap.
- What were you looking for?
- How did it help you?
- What did you not find that you were expecting?
- How often do you reference a roadmap?
This will help you get a pulse of the requisite needs across the organization.
You will likely find 4 major stakeholder groups: executive leadership, marketing, support, and product teams. Each has a different lens and time horizon that they need from a roadmap. Listen intently to what they say and incorporate those ideas into any roadmap solution and process you create.
Once you understand the principles and the needs of your team, you are ready to think about tooling and processes. I have found that starting without a tool to begin with, will help you iterate into the best fit solution for your teams. Choose a medium for roadmapping that can be revised quickly without much ado. Google sheets is great as a starting point.
However, one point of warning when using sheets. You will run into the problem of not being able to roll up your roadmap data once you’ve found the sweet spot of product-solution fit for your roadmap, so be prepared to cycle through the lightweight solution relatively fast.
Finally, that was a ton of preamble to get to what you came here to read, but I wanted you to see that there’s more to roadmapping than just when you do it.
The cadence will help you establish a natural working rhythm for your business that the entire organization can align around, but your cadence will be highly dependent on what your teams need from it.
That being said, it’s my observation that most organizations don’t veer too far from the natural “circadian rhythm” of the Gregorian Calendar. It’s just natural to talk in weeks, months, and quarters. Most people understand that. It’s when you talk in things like sprints and trains that people start getting confused. Just use everyday language when it comes to time. It’s easier for everybody.
These are the three main cadences:
The Quarterly Cadence
- Who: CPO, VP engineering, VP product, VP marketing, and VP design
- What: Review key investment themes and experience drivers
- Outlook: 3–12 months ahead
- Output: One page strategy update summary, next quarterly goal
The Monthly Cadence
- Who: Product leads, customer-facing leads
- What: Gather key customer-facing inputs for planning
- Outlook: 3–6 months ahead
- Output: Roadmap updates
The Bi-Monthly Cadence
- Who: CPO, Product Leads, Team Leads
- What: Drive progress toward monthly and quarterly goals
- Outlook: 3 months ahead
- Output: Roadmap, project plan updates
These cadences are not special, but what is important is that there is an established rhythm, where leaders at varying levels of your organization can get visibility into your roadmap. It should also be noted that teams should plan and operate as their unique culture evolves, with the expectation that the organization has needs.
Take time every month to critically assess what the company has stated as its goals, its objectives, and its plans are for the future. These sessions need to be interactive, and they need to be data- and customer-oriented.
This should be not an activity of making things perfect. This is an activity in making things better through feedback and visibility over time.
Communicate your roadmaps in terms of confidence and not commitment. Use data-driven projections to provide a high level of certainty on delivery times or set thematic goals that are likely to be important in delivering on the company strategy when you are less certain.
If you have done your due diligence on a roadmap format and you have clear expectations with a consistent cadence, you will find success and less stress.
- Follow first principles
- Treat your roadmap and process as product
- Establish a normal calendar rhythm