My mother is the best trip planner I know. When she goes abroad on vacation, she plans it in advance in such detail that even the local residents don’t know about all the places she is going to go to. Her research and planning are so thorough, that she knows exactly which roads have sunsets you don’t want to miss and which activities happen only on the second Sunday of each third month, which happens to be precisely when she is there.

My parents love traveling and we traveled a lot as a family over the years. For all I knew, that’s how you plan a trip abroad. Imagine my surprise when Arik and I approached our first trip together, to lovely California, and he wasn’t planning at all. He wasn’t even planning on planning, but rather just getting there, reading the recommendations on the plane, and deciding each day where to go. I freaked out. I couldn’t imagine traveling this way, and potentially missing on things that we could have done had we just planned ahead of time. 

When we started talking about it, I realized that not only do Arik and I have very different methods for trip planning, but we rather see the whole purpose of the trip differently. It was then that we needed to discuss our real priorities. Is our primary goal sightseeing or simply rest? Do we prefer nature or urban experiences? What is the role of food in the trip – is it part of the fun or just something you need to do and keep going? Do we prefer driving longer distances in order to stick to fewer hotels or are we good with changing our hotel every night?

Note that each of these decisions leads to a ton of details in the plan itself, but if we don’t discuss our real priorities the details are almost random. 

The same happens with your roadmap. When you start discussing the details (features or epics and where and when they can fit in) there are bigger priorities that should guide you. In fact, even if you discuss strategic themes, think higher up. Your roadmap must serve the company’s (business) goals, and therefore that’s where you need to start. Here are a few reasons to discuss these priorities that really matter, even if it’s not easy.

It’s All About Impact

Roadmaps are here for a number of reasons. One reason is that everyone needs to know what to do. Another reason is for others to know when they can expect things to happen so that they can plan their own work. But all of it doesn’t matter if you don’t work on the right things, the ones that make a difference in the product’s success. Note that I didn’t say the right features. These right things have a much broader context than the features, epics, or even themes. Here are a few ways to uncover the real reason for doing things.

Roadmap planning is a balance between top-down thinking and bottom-up thinking. Start by listing the top priorities for the company, as you understand them. Do you understand why they each matter? What is the company trying to achieve by making it a priority? Ask yourself if it’s the right goal, and why. Think about all other potential goals that you could have set (put yourself in the CEO’s shoes) – would you still choose this one? Why?

That’s the top-down part. By the end of this part, you should have a list of well-defined priorities and objectives that you fully understand why they matter. Note that the qualitative here is much more important than the quantitative definition. It’s much more important to say that we are trying to establish initial signals of product-market fit than to say that we need a certain ARR value. If your goals are in revenue, make sure you understand why these are the numbers. What happens if we make 50% of it? Why is it important to achieve the full amount, even in order of magnitude? This would usually uncover the qualitative objective behind it, which in turn might change the goal to something like “having 5 big logos and showing that we can convert freemium customers into 6-digit deals”.

Now it’s time to bring in the bottom-up part. I know you have a long list of features and capabilities that you want to work on. I believe you that they are important. But lacking context, they wouldn’t take you to where you want to go. For each of the important building blocks of your roadmap, ask yourself why they are important. Keep asking why until you reach one of the following: (1) you tie it to one of the company priorities and understand exactly how it contributes to achieving it (2) you uncover another business top priority that wasn’t listed there before but it is really important, or (3) you realize that it’s actually not that important for now, looking at the real priorities as you now understand them.

It’s All About Decision Making

Goals are great, but unfortunately, too many companies list far too many goals simultaneously, which kind of defeats the purpose. The whole point of setting goals is to help people focus and understand what they need to achieve, but if everything is equally important (and we know that in most cases not everything is achievable), you haven’t really helped anyone.

Roadmap planning is a great opportunity to help the company make the tough decisions that they need to make. Once you clarified the goals, I highly recommend prioritizing them before you get into the details of what you can fit into the plan. I encourage you to do that since it will help you to remain as objective as possible. If you start your prioritization only later it will be biased based on the features you are trying to squeeze in.

To help with this objective prioritization, simply ask which goal out of those listed is most important. It will be hard for you to answer it, and in most cases, it will be much harder for the CEO to do so. That’s why it’s a tough decision to make. Note that stating that something is your first priority doesn’t mean that you will focus only on it and abandon other goals. It also doesn’t mean that you only start working on the other goals when this one is fully achieved. You can still work on multiple goals simultaneously (I recommend no more than 3 because it’s hard to focus otherwise), but prioritizing them means that you thought in advance about the trade-offs that you would be willing to make. 

These trade-offs will surely be needed. Product development is such an uncertain world, both from the outside and from within. You keep learning new things about the market, and delivery always takes longer than planned. You run into obstacles that you didn’t expect and need to re-calculate your route. 

Prioritizing at the right level – the highest one – helps you make these decisions more smoothly along the way. Moreover, when there is a logical path that explains exactly what made you prioritize this way, you can always go and ask yourself if anything in your core assumptions has changed. If not, then it’s a lower-level decision. We still focus on X, but we realized that the path we took isn’t going to take us there, so we need another path. It’s a much easier decision to make than if you did it without prioritizing at the highest level because the decision is no longer contained, and would look something like “I worked on something and it failed. Now what?” It’s a completely different scope of the decision.

It’s All About Leadership

Last but not least, prioritizing at the right level not only helps you think, but also helps you explain how you think to others – your colleagues in the company management, all the relevant employees, and higher up in the organization, all the way to the CEO and the board of directors.

Being able to communicate and articulate priorities clearly is part of what makes you a good leader.

With your colleagues in the company management, discussing the real goals and the priorities between them helps you align and make the right decisions, which leads to better focus as well as execution. The CEO can then use the outcome of the discussion to communicate to investors and other stakeholders.

With everyone else in the company, clear communication helps them understand you much better. It’s important because it increases the chances that what they build actually meets the goal because it will guide them through the many decisions they would be needing to make every day. But at the deeper level, it also instills trust in leadership. Hearing that you think about these things and are able to make tough decisions is exactly what helps them feel your leadership. They might not agree with the priorities you set – but if explained clearly there is a good basis for that discussion to happen effectively.

Moreover, when things will change – and they will, we all know it – if you have done a good job explaining how you think in the first place, it will be easier for you to understand why you changed your mind. You probably have learned something new or realized that something is more complicated than you thought. This, too, helps build your leadership and the team’s confidence, in the times they need it most. 

Prioritization at the right level not only makes your roadmap better, but it also helps you become a better leader. It’s not easy – prepare for long and sometimes uncomfortable discussions – but definitely worth it, for more than one reason.