My sister and her family are about to move to their new apartment soon. How soon? They actually were supposed to be there already, but you know how these things happen. The deadline is long overdue and the apartment is not yet ready. Join me in wishing them good luck with moving soon!

I’m really happy for them, especially remembering the journey they went through on their way to finding the perfect home for them. It started a few years ago when my sister and her husband needed to decide whether or not they were going to buy a certain apartment that was on the market. There were so many pros and cons that she didn’t know what to do, and asked for my advice. Instead of giving her answers, I asked her lots of questions that helped her figure it out for herself.

These questions were part of specific techniques that I also use with my consulting customers and in the CPO Bootcamp when people need to make complex decisions (and you know you do, right?). So here they are – my top three techniques to eliminate the complexity and create clarity that would allow you to move forward in almost any situation. You can use these to organize your own thoughts, but even more importantly, use them any time you feel an important discussion is going in circles. You’ll help everyone get out of the deadlock and bring the discussion back into the productivity zone. 

I’ll use my sister’s decision example throughout this article to demonstrate how it goes. Here we go.

Split Complex Questions

When I first heard my sister describing her situation, I identified an underlying subtext of “we must get a new apartment soon”. Since the availability of apartments for sale in the relevant neighborhood was limited, this added a lot of complexity to the discussion. It felt like making a decision with a gun pressed to your head, which is never a good idea. 

To simplify it, I split the discussion into two separate questions: first, do you need a new apartment now, and second – are you going for this specific one. Once you phrase it that way, it’s easy to see that you can’t discuss the latter without addressing the former first. So that’s where we started.

The (now more focused) discussion revealed that while they would be happy to move out of their existing apartment into a bigger one now, they can actually hang on in there for additional 4 years or so. They had some more time to find the right apartment, which means that they can wait for additional apartments to be offered for sale. Even though we didn’t discuss the specific apartment that they were considering, one of the items in its pros list became irrelevant as a result of our discussion: the fact that out of the apartments available now, this was the best fit. If they still have time, the current supply doesn’t matter as much.

On the more professional side, I find myself using this technique often in roadmap discussions when I’m suggesting separating the discussion on what you want to do and in which order from the discussion on exact timelines. Another common example is when people ask me to review their strategic plans (for a new round of funding, for entering a new market, etc.) and before we get to talk about whether or not their plan is good, I want to make it super clear why do they want to go down that path at all. Splitting these large discussions into (1) do we want to enter a new market (2) which market and (3) how, helps focus the discussion, see things clearly, and make decisions simpler. Moreover, the answers to the first questions would have a significant impact on the last one, so it’s better to tackle them first anyway.

Debate the Ideal Solution Even if You Can’t Have It

One of the things that made my sister’s decision complex, was that the apartment at hand wasn’t a perfect fit for their needs. But in order to understand whether or not these are compromises that they are willing to make, she needed to first clearly understand what these compromises were at all. When considering the specific characteristics of the specific apartment, it’s not always clear which compromises are significant and which are relatively minor.

To overcome that, I asked her to describe her ideal home. She immediately responded that it depends on what budget. While it’s a real consideration when you want to make the actual decision, when we are looking for our ideal solution it is important to ignore it for a minute. Some of the characteristics of an ideal apartment would turn out to be over budget in real life, but some might surprise you with how easy they are to get. Moreover, if you want to truly understand the compromises that you are making, you want to understand where you would have loved to be if there were no constraints. Allow yourself to dream without any constraints before you bring your dreams back to reality.

In the professional world, this is even more important, since we are creating our dreams all the time. Some of these have to do with creating a vision – allowing yourself to ask big questions like “what does it take to do 10X on our revenue next year?” But here are two more specific examples where it is very important to live in the theoretical world before you bring it to reality with its specific constraints.

The first one is with metrics. Often when I start talking to product leaders about how they would like to measure certain aspects of their product, they immediately think from within the data they have, or the data that they can have. However, understanding the right, ideal metrics is important in your ability to think strategically. Even if you can’t measure them exactly and would end up with some other form of measurement that is a proxy, you would still know what you really wanted to measure and make smarter decisions accordingly.

Another example is ideal customer profiles. As the name suggests, these profiles need to be the ideal customers for you and your product, but many product leaders and founders immediately translate them to characteristics that you can easily filter on LinkedIn so that they can find the actual customers easily. For example, it might be that your ideal customer profile is a CISO who likes to innovate, who feels that they need to take the organization forward using advanced technology. This is something that would be very hard to recognize from a LinkedIn profile, but it is still important that you know that this is what you are really looking for. You can build your marketing materials to speak this advanced technology jargon, or even ask specific questions in a sales call. If you only limited yourself to what you can easily understand about someone without talking to them, you wouldn’t have realized that this is even important, but this can make the difference between a product that sells and one that doesn’t.

Divide and Conquer

Once we understood the timeframe for a new apartment and understood what an ideal one would look like, it was time to look at the specific apartment at hand. Some of the complexity of the decision was already removed by earlier phases of the discussion, but there was still a lot to consider. There were things like light and noise which weren’t great (but not unresolvable either). There was the price, that while was within my sister’s budget, felt too high given the previous concerns, and there was the fact that my mother (whose opinion we highly value) didn’t like the apartment. But my sister’s gut feeling was that she needed to take it given the relatively tight budget and a very specific street that she wanted to live in. Not an easy decision.

From my experience, even though there seem to be about a dozen different things to consider here, there are typically one or two that matter most and these are the real hard questions that we need to answer. Once these are answered, the rest is easy to figure out, or even unnecessary to discuss at all. To find these one or two that truly matter, we need to test the parameters one by one. I use a simple and quick method to do so.

Step 1: list the parameters. Light, noise, price, budget, location, my mother’s opinion. List them all in broad daylight. It’s much easier to work with them when they are all explicitly part of the discussion rather than ignoring some of them (like your gut feeling or your mother’s opinion) because you would like to think they are irrelevant. If you care about them they are relevant. 

Step 2: work with one parameter at a time. We are going to ask a series of questions, and each time everything is going to remain unchanged except a single parameter.

Step 3: take each parameter to both extremes. Here is how it goes: say you want to work with location as the current parameter that we are exploring. Ask yourself: if everything remains the same, but the location is exactly where you want it to be, would you take the apartment despite its deficiencies? If the answer is yes, you can now focus on how far is it from the location you really want. If the answer is no, you know that location is not the anchor you are looking for and has a smaller weight in this specific decision.

You can also do it the other way around. For example with my mother’s opinion, I remember asking my sister the following question: if the apartment was exactly what you wanted in all other dimensions, but our mother still thought it wasn’t worth it and you shouldn’t take it, would you take it? Her answer was ‘yes’. This led us to see that our mother’s opinion wasn’t a key factor here, but rather the actual problems with the apartment my sister and her husband were considering.

In the professional world, I most commonly use this technique in hiring. Candidates are rarely perfect, and we frequently need to make informed compromises. But how do you know which compromises you are willing to make? If the candidate’s salary expectations are too high, ask yourself if they were perfect in every other parameter would you take them (there is no right answer, sometimes it is worth it and sometimes it isn’t, or you simply can’t afford it even if you want to). If they have no technical background, ask yourself if everything else was the same but they did have the technical background would you take them? And so on. It helped me understand what’s important for me numerous times, and in some cases helped me realize that while I already want to close this position, there are too many compromises I’m about to make with a specific candidate and made it easier for me to pass.

As for my sister and her husband, they ended up not taking the specific apartment we discussed. They took a little longer to search but found a great place that they are about to move into very soon. She thanked me for my help in organizing her thoughts, and I’m glad I could have contributed to her – and hopefully yours as well – complex decision-making process. It’s not always easy, but unfortunately, we need to do it anyway. 

Which complex decision are you currently facing? Try these techniques and let me know how they worked.