The official start of spring is March 20, but there is something about April that really represents the season’s changeover. In most locales, the temperatures are up and plants are starting to spring back to life. In my area, the weekend air is beginning to carry the sweet and smoky smell of barbecue. There is no meal quite like that from a home pitmaster, who wakes up before the sun to carefully tend to the firebox temperature and smoke quality. This backyard hero has their plan for the cook, but they know that their expertise comes from their ability to audible throughout the day based on fluctuations in the outside air temperature, the humidity, the cut of meat, and so much more.
April kicks off much more than the spring season. It is also the start of Q2. With the new quarter, most teams will take the time to refresh their roadmap. Whether for product, testing, or general priorities, a roadmap is a valuable tool for planning and communicating work over a longer time window. Still, a lot of people have a love/hate relationship with roadmaps. While it is a useful tool, teams regularly find themselves frustrated with and stressed by their roadmaps. The most common problems come from:
- Lack of Flexibility - Resources are almost always booked to capacity. How should new mid-quarter requests impact what has already been planned? Should new projects wait until the new quarter to be prioritized or be squeezed to fit on the docket?
- Unrealistic Expectations - Timelines are almost always optimistic. When a part of a project is running over its forecasted time window, how should subsequent dependencies be impacted? Should projects be rushed or should work be delivered late?
- Misalignment with Business Objectives - Business context almost always shifts. Should projects be discontinued if the value drops? Does a project need to be scoped again from the beginning when its context changes?
- Poor Communication - Stakeholders rarely have our team’s work as their only focus and often forget what is planned. How can multiple disparate stakeholders be kept continuously aware of relevant information? Should time be spent on continuous status updates?
When the benefits and problems of a roadmap are so closely intertwined, it is not surprising that they often create angst. But, as such a core aspect of organizational planning and delivery, it is unlikely that we will see these go away any time soon. So, what can we do?
Inspiration often comes from unexpected sources. We can find a lot of parallels for the flexible planning strategies and communication expectations needed for effective roadmapping in barbecue. Like our roadmaps, an effective cook starts with a good plan. Yet, an experienced pitmaster knows that they will need to adjust on the fly. In truth, this adaptability to deliver a great product regardless of the situation is what separates the great from the good.
Lack of Flexibility
Roadmaps act as a multi-purpose tool for most teams. Their core function is to describe a team’s planned priorities. With this, comes an implicit secondary purpose - to justify resource allocation. As a result, team leads are tempted to fill every week of the quarter with activity and cover a wide variety of projects to show that they are fully leveraging their team. This can obviously create problems when new opportunities arise. When all time and resources are already accounted for, there will not be extra bandwidth to cover these new projects. Similarly, unplanned work to fix problems with existing product functionality or campaign performance is usually not included in planning. This work is important for maintaining effective operations, but would require unseating a different roadmap project.
This temptation to maximize what is available is a fairly universal one. For our pitmasters, the capacity constraint is space in the cooking chamber. Particularly for newer hobbyists, the temptation is often to fill the entire cooker and try to make a little bit of everything. This can cause problems as the cooking process for a chicken is different than that of a brisket. Pros will also regularly move cuts to different areas of the cooker that are hotter or cooler based on how things are progressing. They also generally focus a cook on one primary cut of meat and find complimentary options that will work in those cooking specifications.
As we think about roadmaps, our work quality can benefit from a similar discipline and moderation. First, recognize that work will likely need to be moved around in the quarter, so it is good to plan for about 80% of full capacity. As critical fixes for bugs show up, your team will be able to jump on them immediately without disruption to large priorities. This also allows space to introduce valuable new projects part-way through the quarter that were not initially planned for. Second, try to be thoughtful about what type of work is prioritized in a quarter. Projects focused on fine-tuning operations require a different mindset than new-market exploration. Each type of project benefits from different work styles. If you start trying to deliver too many disparate projects all at once, you can create sub-optimal environments for all projects. Third, set the expectation with your team that things will change. I have written before about building team resilience and an important feature of those teams is that they acknowledge and expect instability. Promoting flexibility with your teams at the start will help boost creative problem solving as new work comes into play.
Unrealistic Expectations
We all fall victim to the planning fallacy at some point. When we do, we put ourselves in a difficult spot on our roadmaps. The planning fallacy is the bias that leads us to be optimistic about the time it takes to complete work. As a result, we often leave ourselves and our teams with unrealistic expectations for how quickly a project is going to be delivered. Maybe that timeline will be true in the best case scenario. But, the reality is that our work is generally complex and unpredictable with many factors that can impact the timeline and outcome of a project. When we do not expect variability, it can lead to frustration and disappointment among team members and project stakeholders.
In barbecue, the name of the game is patience. The “Low and slow” mantra stresses the need to allow for a cook to take its time. “If you’re looking, you ain’t cooking” tells pitmasters to keep the chamber closed to retain heat and that attempts to micro-manage the cook will ultimately just slow it down. “Nobody has friends over to ‘microwave’” reminds us that good, quality outcomes take time. In fact, while most pitmasters start with a plan for when they hope a cut will come off the cooker, the reality is that it's done whenever it's done. Variables like air temperature, humidity, the weight and fattiness of a cut of meat, firebox temperature consistency, and more can all play a factor in how long a cook will take. It is best to approach each cook with a sense of realism and understand that not everything will go exactly according to plan.
Thinking again about our roadmap, there are a few ways to carry over these lessons. First, be transparent and clear about risks and challenges in the roadmap at the outset. Clarify difficult tasks, aspects that require cross-functional collaboration, and places where there are likely to be “known unknowns”. If you can build extra time into the roadmap for these instances, even better. Second, focus on the delivery process rather than just the timeline for the project. It usually matters less about whether a project is completed at a specific time and more about the value created by its delivery and the capabilities built in that process. Third, as you move through the quarter, realize that trying to add more people to “speed things up” or implementing more status update meetings to “drive urgency” often do more harm than good. Let the team focus on creating value versus stressing about an artificial timeline.
Misalignment with Business Objectives
Roadmaps play an important role in planning a single team’s work, but their full value is realized when used to ladder up the team’s priorities to broader business strategy and goals. Often, this tie-in gets lost as the roadmap gets built. The disconnect may happen because the most cutting-edge opportunities for the team do not match the operational requirements of the business. Similarly projects that support the development of individuals on a team may not line up with the work requirements for the business at that time. In the worst case, the roadmap may just be designed in isolation without any consideration into cross-functional collaboration. The net effect is that teams pursue projects that are not aligned with the direction of the company or prioritize projects incorrectly, leading to work that does not get broader buy-in and gets thrown away.
Again, we can find some parallels in barbecue, albeit more in the restaurant industry. Menus need to be planned to meet the tastes and interests of consumers! For a pitmaster looking to master their craft, a brisket may offer a greater challenge than pulled pork. However, a pulled pork sandwich is a staple in almost any barbecue setting and cannot be excluded. The regional styles matter too - you would have a hard time getting a vinegar-based sauce to be widely used in Texas, for example.
For roadmaps, this means we need to design with our stakeholders in mind. The best thing to do here is involve them in the planning process. Give them a chance to contribute thoughts during initial brainstorming and to review expected timelines before anything gets set in stone. Ask questions to clarify what is important and how different timelines would influence the broader team. It is generally best practice to follow a framework like OKRs to flow your big rock activities down from higher level company objectives. Maintaining priority alignment throughout the quarter also means revisiting and adjusting the roadmap on a recurring basis. I generally recommend sitting down with stakeholders monthly to learn about how context around the business has changed. Seeking this information proactively can also help work from being added at the last minute as a surprise.
Poor communication
The final challenge with roadmaps is improper communication. Without clear and consistent communication, teams may not have the information they need to make informed decisions about priorities. This can lead to confusion on cross-team collaboration as work gets out of sync. Stakeholders can also become frustrated by what appears to be a lack of progress while the only real issue is lack of communication.
We will go back to our barbecue metaphor one last time. Knowing how much variability exists in how long a cook takes, good communication is a key to getting everything to come together exactly right. For example, if someone is making a side of mac-and-cheese that needs an hour to cook, it is most important that this side dish starts to cook roughly an hour before the barbecue is ready to serve. While the initial estimated mealtime is a good anchor point, it would be better for the pitmaster to share timing updates as they go. Similarly, if the cook went quickly, you do not want guests showing up at 6:00pm if everything was ready to eat at 4:00pm.
To pull that lesson across, teams should make effective and low-lift communication a priority. First, establish a regular check-in process with stakeholders. I recommend a monthly sit-down to review the objectives and their status as well as any changing context. A thorough discussion is one of the most effective ways to maintain alignment. Second, use the roadmap as an easy communication tool. The document should already be largely structured to illustrate the top initiatives and their sub-projects. Take that format and add columns for ‘Last Week’s Progress’ and ‘This Week’s Priorities’ to build a low-effort weekly progress document. This lower context, lighter lift document can be shared with more people asynchronously and help to maintain general project awareness at any point in time.
Quarterly roadmaps can offer good value to any team. But, in the hands of a pro, they become an invaluable tool for working cross-functionally to tackle the complex and variable business world. While documenting a schedule may seem like a tactic to force rigidity, teams can think like pitmasters to address the challenges of inflexibility, unrealistic expectations, priority misalignment, and poor communication. Like any cook, an effective roadmap starts with a good plan. The craft comes in everything that happens once the fire starts burning.
Share your work-related questions and dilemmas with us for upcoming blog post consideration.