When I was in high school, I had very long hair. I am extremely tall, so when I say that my hair was running all the way through my back, that’s a lot of a way to go through. Unfortunately, when I was in high school, my sisters who are much younger than me were still at the age that they had lice at school. And so, since I wanted to keep my long hair lice-free I used to comb it using lice comb every single day, 7 days a week. 

It wasn’t a pleasure, but it was necessary. I can say that it also worked most of the time, and I kept my very long hair until I was 25. It also means that I have a lot of experience combing long hair. We’ll get back to that in a minute.

When I talk to the startups I consult to, or with the CPO Bootcamp participants, I always say that building a solid product strategy isn’t like solving a math equation. It’s not a fill-the-blanks exercise that you simply complete and that’s it. In the process of building your product strategy, you would need to face many non-trivial questions as well as hard decisions you would need to make. It needs to make sense to you (since if it doesn’t work at least on paper it will never work in reality), and connecting all the dots in a complex world with infinite options and many unknowns is challenging.

Therefore, the process that I recommend for creating a solid product strategy is an iterative one. You need to work through your strategy multiple times until it makes sense. These iterations are not like scrum sprints, instead, they resemble the process that I go through when combing long hair. And please, if your method for combing long hair is different, I ask that you still stick to mine – that’s why I shared with you the 10 years of experience I had with lice combs on a daily basis 😉 It works for lice and it would work for your product strategy, trust me.

By the way, it also works for other strategic decisions like a roadmap, OKRs, or deciding on a new org structure.

The combing method is simple: When you comb a long hair you start at the top and continue until the comb can no longer pass through and you are stuck. The hair is too tangled. At this point, you must untangle the problematic hair before you continue, or else you wouldn’t be able to get any further. When the specific point is untangled, you start again from the top and the comb gets further out, but probably not yet all the way through. You need to repeat it – untangle the problematic hair and start again from the top. Eventually, there will be no additional tangles and the comb will pass smoothly from top to bottom. That’s when you know you are done.

Now let’s see how each phase applies to your strategic thinking process.

Start at the Top

You always need to start at the beginning. With anything related to strategy, you want to give as broad a context as possible. On top of that, people always understand better top-down than bottom-up. Think about it: if you want someone to draw based on instructions from you, it is much easier to tell them that you are going to draw a cat and then explain to them how to draw it, rather than asking them to draw a circle, add two triangles at the top, a dot in the middle and add straight lines from that dot sideways. 

Since strategic discussions usually happen in a group form, it is even more important here. The people in the room don’t only need to hear you out and understand what you are talking about, but also make sense of their own thoughts throughout the discussion. They usually don’t have it all figured out, even if some of it was their idea to begin with, and by taking them step by step from the top you are also helping them think.

If you prepare for the discussion, or when you start thinking about product strategy all by yourself, choose the right starting point. Look for an anchor that has a general agreement (although sometimes by calling it out loud you’ll be surprised to see that there isn’t really). It could be the goal you have in front of you, the mission statement or anything else that people would relate to. Then take it from there with logical steps that lead you toward where you want to be.

Continue Until You Are Stuck

There are two forms of being stuck in such a process: either people disagree with you (which as I said can happen in the very first sentence of your product strategy pitch), or you lost your way and it doesn’t make sense to you anymore.

In both cases, you need to understand where the problem is exactly. What do people disagree with you about? Don’t let them just say “I disagree”, dive into the problem, ask them to describe how they see it, and pinpoint the disagreement. If you are doing it by yourself for now, take a step back and clarify for yourself what exactly doesn’t make sense to you. Which dots don’t connect, or even contradict each other.

It is important to understand the problem in depth because otherwise it will be very difficult to solve it, which is our next step. Sometimes, by the way, just by understanding where exactly you disagree with other people, the problem solves itself – you might be able to find research that supports one side of the argument, or understand that the next step is to conduct such research by yourself.

Figure It Out

In most cases though, just stating the problem isn’t enough. You need to dig through it and truly figure it out. It might take some back and forth to get there. You might need to try out a few options until you feel that what you now have makes sense. It might take a few back-and-forths just to be able to understand what bothers you, even before you find the answer.

It also might be that the change is bigger than the specific point you are stuck at. For example, you might realize that you need to tell the whole story from a different perspective. Remember that you are trying to describe a complex world in a way that makes sense, and it’s not always easy. There are multiple ways to tell the story, and many different outcomes that you can lead to. Don’t let this discourage you from moving forward.

Creating a product strategy is one of the hardest things you need to do as a product leader (that’s why many companies simply skip it altogether), but also one of the most important. The impact of being able to sort it through is immense, so make it your real commitment to succeed despite the challenges.

Start Again at the Top

When you write an email, do you read it again before you send to see if it makes sense and conveys the right message? I do most of the time, and often it causes me to revise them. That’s how it works with strategic iterations as well.

Once you have a new version of the product strategy (or roadmap, or OKRs) it is important to start telling it from the top again. You need to do that even if the top didn’t change since strategic materials are gentle creatures, and changing one part there could impact other parts or even the entire strategy.

When I work with startups on creating their product strategy, I usually leave them with homework to revise the strategy based on today’s discussion before our next meeting. At the next meeting, we start from the top. At some point, they always ask that we start from the middle already, since we all agree on the top. I always refuse. The reason is simple: If we truly agree on everything, it will be very quick and easy to run through it from the top, and we would have it as fresh context when we get to the part where we disagree or that doesn’t make sense anymore. But in most cases, even when people think they agree, they actually don’t, and we end up talking about important things that would have blocked us later if we hadn’t discussed them thoroughly. 

In one such startup, that asked to start in the middle, we ended up spending a full hour discussing the first sentence. It read “we focus on the SaaS market”. I immediately felt it was too broad, and started asking hard questions: is any SaaS company relevant to what we do? And what if a non-SaaS company asked to work with us (they had a technology that could support that) – would we tell them to go away? It was these discussions that helped the founders create alignment on their goals as well as the compromises they are willing to make. It was an extremely important discussion, and the next time no one wanted to start from the middle. 

If you want your product strategy and other strategic outcomes to make sense, you must take the time to iterate them again and again. Whenever you have a feeling that something isn’t 100% right, or that the following sentence isn’t derived directly from what we said up until now, stop and figure it out. Don’t be afraid to comb your strategy as many times as needed. Eventually, the comb will pass easily all the way through, and your strategy will be more solid than it had ever been.