At the beginning of the 2011 movie “I don’t know how she does it” Kate Reddy (Sarah Jessica Parker) needs to bake a pie for the school bake sale. Unfortunately, she only remembers it on her return from a business trip the night before. Committed to her family duties, she buys a pie at an open store but wants it to look homemade, so she deliberately ruins it a little (because who can bake a perfect pie?) and moves it to a different dish. 

This scene says a lot about trying to live up to what other people think, but I want to look at it from a different perspective for a moment. It’s about the compromises that we all make. 

In an ideal world, I believe Kate would have wanted to bake a pie. But since she (and none of us honestly) can’t do it all, she compromises for a bought one.

I know I make many compromises when balancing work and personal life. My kids could definitely eat healthier and have their screen time managed better (or at all), and I don’t always happily accept these compromises. On the other hand, they all know that family is their safe space and that we would accept and support them no matter what. These are compromises that I am not willing to make.

Moving to the professional world, we all make compromises there, too. The product leader’s role is so busy that we simply can’t do it all, and often, other constraints force us to do things differently than we ideally prefer.

One such area is roadmap planning. My recommendation for roadmap planning is to start top-down, from the company’s strategy itself, understand it in depth, and only then start planning how you are going to make it a reality. Bottom-up planning (coming from what you already know that you want or need to do) complements this process and keeps us rooted in reality.

I highly recommend following this process at least once a year since it often unveils important strategic insights, aligns all departments to work together, and increases the chances of meeting your goals rather than simply adding more product capabilities.

But it’s not always possible. In startups, for example, things are so dynamic that it sometimes feels irrelevant to plan too far ahead. I would still recommend applying the process there, too, but if management isn’t with you, you might struggle to do so.

Even in more mature companies, if the company doesn’t have a solid strategy and doesn’t see the importance of discussing it before planning, you won’t instantly change that DNA. 

And sometimes, if you don’t have a strategic roadmap, the CEO might want one ASAP, for example, before a presentation to the board or an important customer. Even if everyone understands that planning takes time and that ideally we should start at the top, sometimes you simply don’t have the time to do so. 

So, on the one hand, you have to compromise on something. If the CEO needs a presentation for Tuesday you need to have it ready for Tuesday. But as you make those, there are some things you don’t want to compromise on.

Like many other things in life, if you have to, you can get most of the value with a smaller effort.

It starts by not forgetting the ‘up’ part, since otherwise you are just stacking features on a timeline, which is almost meaningless.

Here is a 3-step process for bottom-up planning that you can use if you have to. Keep it for a rainy day.

Five Whys, but Different

You are probably familiar with the concept of “five whys”: asking ‘why’ five times until you get to the root cause of something. It’s a common practice in problem-solving meant to ensure you solve the right problem and not just the symptom.

In the product world, we often use it with requests we get from customers or stakeholders to ensure we understand what they really want and not just do what they ask (since they are not product managers and they speak in features instead of problems).

For planning purposes, I advise you to use this method to question yourself. You already have many things you know you want or need to do next year. For each one, ask yourself why you want to do it. And then ask it again, and again, five times or until you get to something that feels undebatable or core to your strategy.

It could look something like this:

We want to add another security layer to our product.

Why? Because we are a security company and it’s important that our products are as secure as possible.

But why now? Because our customers started asking about it.

Why? Because they seem to be more security-aware.

Why? What has changed? Because we started selling to healthcare companies. 

Why did you start selling to healthcare companies? Because it’s a strategic opportunity that the company has decided to pursue. 

Do that for every feature on the plan to have a better context for each.

Paint the Bigger Picture

The five whys process forces you to raise your head from the features to the reasons you are planning to build them. It’s not as strategic as starting with the goals and planning for them, but it’s good enough if you have to work bottom-up.

Now that we are at the reasons level, we can start making sense of it.

In this step, you want to group your features into larger initiatives that are rooted in reasons and not in outputs. Look at all the reasons that you have discovered. Most likely, many of them will collide. 

In the example above, you will probably find additional features that map nicely into ‘the healthcare opportunity’. Note that you might need to be pragmatic and not purist when you think about these. It could be that there are features that have other reasons, like ‘the company’s grand vision’ or other customers want them too, but the reason for picking them now and adding them to the plan was really the healthcare opportunity. In such a case, it would serve you better to group them under the healthcare opportunity rather than add another separate reason.

Ideally, everything you do should be mapped into 3-5 major initiatives or reasons. This is important for the next step.

If you end up having more, see if some of them can be further grouped together. Ask ‘why’ a few more times – this time on the reasons themselves – to see if you can find a common denominator. For example, if you have ‘remove sales barriers’ and ‘shorter onboarding time’ as primary reasons, they might fit nicely into a more core reason of ‘scaling our sales process.’

Tell the Story Top-Down

Now that you have 3-5 starting points, and everything you want to do maps nicely into them, it’s time to tell the story top-down so everyone can understand, remember, and follow it.

Note that while we haven’t started the process top-down, and the ‘top’ in this case might be lower than where we want it to be had you started with a proper top-down process, it’s still important to tell the story top-down as it is. 

That’s how people think, and by telling it that way, you will create clarity that couldn’t exist otherwise. 

Metaphorically speaking, if features are the pixels of an image of a cat, the reasons are its body parts. Instead of describing the color of each pixel and asking people to deduce that you are actually talking about a cat, say that you are describing an image of a cat and talk about the head, the body, and the background as the proper context.

Had we started with a real top-down approach, we would have asked whether or not it’s a cat that we should be working on. 

If I have to, this is a compromise I am willing to make, at least temporarily.

When you present your bottom-up built plan, see if it’s appropriate to add a disclaimer that you are still working on a proper top-down process, and let everyone know that you will update later as you were able to do so. Setting expectations about how the plans might change is always a good idea, especially when planning bottom-up, since there would be more things that you might miss this way.But even if the plan is bound to change, forcing yourself to move up and not remain at the bottom results in a much better plan and much clearer communication of it.