W. is the CPO of a startup in transition. They have a solid business but realized that the growth potential there is limited so they pulled me in to help them redefine their vision and strategy. Strategic discussions at that level take time to materialize. It is very rare to simply sit in the room until everything is sorted out and have a clear vision and strategy as an immediate outcome. Ideas need to sink in, some research is due, and there is a natural evolution process until everything falls into place. And evolution, as you know, can’t be rushed. It takes the time it takes.

W. is struggling with this approach. Being very pragmatic, he hates stale discussions and so in almost every meeting we have, he keeps questioning the process that will lead us to the right product strategy. The last time it happened, I suddenly realized something. The primary reason W. is struggling was that he is looking for something that doesn’t exist. You see, when it comes to product strategy, there isn’t a right answer – the perfect product strategy that is objectively right for the company. There is only the best strategy you can get to, and there are ways to validate that it is indeed a good one. It is never perfect, and will always include trade-offs. And you will never know for sure that there isn’t a better one waiting for you around the corner. In fact, the lean startup approach says that there will always be a better one around the corner, but you must take the turn first to see it.

Embrace the Fact That You Wouldn’t Know for Sure

When W. keeps looking for a deterministic process that will result in the objectively correct strategy, he is bound to fail (since there is no such thing) and his frustration level will keep rising. The first step in moving forward in such cases is embracing the fact that there isn’t a right answer, and that the process isn’t linear and deterministic. These are two different challenges but they both go back to how comfortable you feel with uncertainty. 

To be able to do strategic work you must make yourself comfortable with uncertainty. The more strategic you get (and in W.’s case here it is about as strategic as can possibly be), the higher the uncertainty is because you look further into the future and there are so many things you simply don’t know and can’t predict. To be able to beat uncertainty, you have to accept both the fact that it is here to stay and the fact that your default methods of thinking or resolution are irrelevant here. 

Strategy is not like solving a mathematical equation. There isn’t a clear set of instructions that will lead you to the solution if you simply follow them step by step. Instead, you must shift your mindset to a risk management one: you need to think and analyze and be willing to dwell in the complexity for as long as needed, but at the same time understand when you were able to cap the risk and moving forward with action becomes more important.

Once you have established this mindset for you and the team, here are three methods that will help you make the process more deterministic still.

Understand the Decision at Hand

To be able to take a calculated risk, you must first understand what is the actual decision you need to make, and what are the implications of taking it. A decision on the next big bet isn’t as hard to change as the decision on whether you are a B2B or a B2C company. A decision on the company strategy for a seed-stage startup is much shorter-lived and has fewer implications than the equivalent decision for a publicly traded company.

In many cases, when you try to assess the risk, you will see that it is actually smaller than you thought at first. This makes many decisions less significant to analyze forever and can allow you to move forward when you feel you know enough and you can contain it if you are wrong.

Even in bigger decisions, as is the example with W.’s company strategy above, we realized that it is important to have a solid one primarily for their upcoming fundraising. Their R&D is anyway busy with their current business which is still viable. So even if we choose the wrong strategy, the implications of changing it further down the road are not as severe as they would have been if they had already wasted many months of R&D on building the wrong product.

Define What Makes a Good Answer

Since there isn’t an objectively right answer to your product strategy, you need to spend the time to define what would be the characteristics of a good one. There could be many different strategies that would qualify for all the characteristics (or none whatsoever), but this will still help you rule out those that don’t and make the process much more contained. 

For example, such characteristics can be that your strategy needs to be able to make you a unicorn within 5 years, be related to your current domain, address your current target market, or maybe the opposite – expand to a new market, rely on your existing assets without the need to develop a completely new product or technology, stay within a regulation-free domain, be feasible to implement and bring revenue within a few months, and so on and so forth.

Debate these characteristics within management. Some of these can’t live together. For example, can you make a huge leap without developing completely new technology? Does your current domain allow you to sell quickly enough to bring revenue within a few months? It is these conflicts that make the discussion interesting and important. Don’t avoid them – look them in the eye instead and debate them fearlessly. 

What you are doing here is actually defining the boundaries of your strategic playground. Once these boundaries are well defined, it is much easier to come up with creative suggestions that will meet all of these and will make great candidates for the product strategy you eventually bet on.

Make Theses up and Challenge Them

This is a more bottom-up approach than the previous one. You probably have a hunch as to what your product strategy needs to be. Since we have already established that there isn’t a right one you are looking for, and only a good enough one (according to well-defined criteria per the above or not), maybe what you have in mind is already good enough?

Realistically it wouldn’t be at first, but by raising it and trying to challenge it you might be able to tweak it to become a solid one. The challenging process can help you understand exactly where it falls short so that you can improve it.

It is also a great way to debate a number of possible directions different members of the management team are leaning towards. Instead of debating the theory, let each member make the case for their own thesis, and have other members helping them crisp it up. For each idea, try to genuinely make it last, even if it contradicts your own idea. The goal of the challenging process shouldn’t be to kill the other person’s idea, but rather to find the gaps in it so that they can be filled. Doing so ensures two things: first, you will really listen to each other and understand what the other person thinks. In many cases, you will find that it makes much more sense than they were able to explain to you before you started. And second, you will have a good product strategy on the table. Often more than one, since as I said there isn’t a right answer. It will be much easier for you to debate between a few good options, perhaps even combine a few to a new one that wins over any individual one, than to look for the perfect one in the void.