How to understand problems better

This week we dive into key analytical problem solving skills, systems thinking, how you can ask better questions, and communicating your decision frameworks

đź‘‹ Hi, I'm Jaryd. Welcome to this weeks Slice— the free weekly newsletter about product, startups, growth and working with people.

If you’re not as subscriber already, join below. It’s free. đź‘‡

If you enjoy this newsletter, and know someone else who also might, you can share it below👇

Share The Product Slice

What are analytical skills?

The foundation of analytical problem solving is the pursuit of understanding. It’s about being curious, avoiding intellectual laziness, and socratically questioning problems, data, and ideas until you understand — an understanding of why something is the way it is and how it works, so you can decide what needs to be done about it. 

It’s the ability to examine information or a situation at the right level of detail in order to see what’s most important, see the strengths and weaknesses of different elements, and use these in a systematic way to come up with a persuasive argument, drive a decision, make recommendations or solve a problem.

It’s not about having the answer. It’s about a structured approach to solving problems. People who have good analytical problem solving skills are not expected to have answers and insights readily available, and they often are very candid and humble about saying they don’t know right now. The key skill is knowing what you don’t know, knowing what sort of decision needs to be made, and having a framework for getting you there. 

Create structure where there isn’t

As a PM, you’re going to face a lot of ambiguity across many aspects, and the more senior you become, the more things you deal with will be undefined. This can appear overwhelming, and it will be if you don’t have awareness and a plan in place, however it’s also one of the most exciting and rewarding parts of the job.

Having the skill of identifying when you have an ambiguous problem and knowing how to apply structure to it is essential, because without it you can end up wasting a lot of your own time, feeling anxious and stuck, and deferring responsibility to other people.

Autonomy is one of the three core pillars of climbing the PM career ladder (Autonomy, Scope, Impact), and creating structure where there is none is a big part of that. 

Think about the system 

Think about the following scenarios:

  • You are proposing a product with the goal to bring in new revenue

  • You want to remove friction at the top of the funnel with the goal to get more signups

  • You want to make changes to user profiles based on feedback with the goal of better meeting customer expectations

  • You want to switch to a new payment provider to manage subscriptions with the goal of saving on fees and making future dev work easier.

  • You want to redesign a heavily-used feature with the goal of making it more user friendly

These seem like obvious wins at first glance. We’ll return to these in a second. 

Systems thinking is when you consider things holistically -- or the whole rather than the part. Most of the decisions that you make and the things that you work are not siloed, and have an influence and impact on other things too. 

Shifting your thinking from linear  to circular is a valuable problem skill because it nudges you to ask better questions, think of the edge-cases and risks, and ultimately better understand the context and trade-offs. This all puts you in a much better position to make informed choices.

Returning back to those scenarios above and applying a systems mindset, we might ask.

  • If that new product is successful, could it cannibalize our main product? (i.e decreased usage, people willing to pay for it)

  • If we make it easier for more people to join, could we be getting lower quality users?

  • If we make changes here, what functional impact does it have on other components like search?

  • How are existing subscribers and renewals going to be affected?

  • If we make this change, how might users who are very familiar respond, and could this increase the load on customer support?

The key skill of systems thinking is knowing there is interconnectedness, and seeing the implications and repercussions of a decision. 

Here is a visualization that shows what happens when you apply a systems mindset to problems. As you can see, the right hand side looks a lot more useful.


Be curious and and ask questions

The answer is what might seem most valuable, but the question is really what uncovers the most insight. It’s more than ok to not know or understand something, as long as you’re willing to be curious and ask. Especially in group settings, people are less likely to ask something out of fear of appearing stupid, thinking it’s obvious and everyone else gets it (often not the case).

Asking a question usually always gives the entire room more insight that can lead to much more productive conversations. 

  • Questions help you uncover what is true. Don’t always take things at face value, dig deeper. At the least, you learn a bit more and understand. At most, you can totally save the direction of something. 

  • Questions give insight into the way people think and what drove a decision. Especially as you become more senior and work with more people, it’s important to understand the people that you work with and how they approached something. This puts you in a much better position to share your ideas and feedback.

  • Questions are one of the most powerful tools at your disposal. In your career, PM or not, and in your personal life. Your role as a PM is to be able to answer the Why, What, How, When types of questions, which means you have to be asking them and figuring them out before anyone else.

Questions are clearly very important, and there are two frameworks for becoming better at asking good ones.

1. Socratic questioning

Socratic questioning is a way for you to gain a deeper understanding of a thought, idea, system, problem, situation and logical implication or something by following a disciplined and intentional line of questioning.

It’s really just asking and answering questions to stimulate critical thinking and to draw out ideas and underlying presuppositions, where at the end of it everyone involved has more insight and lands at a more logical conclusion. 

Socratic questioning is also a highly-effective leadership and management tool. This is because it helps you understand and assess the thinking of other people. 

Say for instance someone from another team brings you an idea for a new feature that you believe is based on a problem that isn’t true, and think would be a waste of resources. Remember, you’re the gateway other teams usually have to get through to get their ideas worked on, so this is very common. You’d have two philosophical approaches to dealing with this scenario. 

  1. You could just shut it down. This is fast and easy, but the downside is you’re bashing the morale of your team member who trusted bringing you something. This risks hurting your relationship with them and not getting other feedback brought to you in the future.

  2. You invest some time in socratic questioning with them. By asking them questions and pursuing a better understanding of their assumptions, steps and viewpoints towards them seeing their own thoughts differently, you’re not forcing a decision upon them, rather they can come to the more accurate conclusion themselves through your guided questions.
    Or, together, you both end up at a different conclusion than you expected through the conversation that’s more meaningful than the first. 

At a high-level, this type of questioning can help you:

  • Raise basic issues

  • Dig beneath the surface of things

  • Pursue problematic areas of thought

  • Help other people uncover the structure of their own thought 

  • Analyze thinking - its purpose, assumptions, questions, points of view, information, inferences, concepts and implications. 

There are 6 types of socratic questions, below is a summary table of each and examples of questions to ask. 

2. The Five Whys 

The Five Whys is a method of analyzing the root cause of an issue. Essentially, you ask a question around a problem that’s already occurred, get an answer, ask Why, and keep asking Why to the subsequent answers until you’ve found what the real cause of the issue is.

You can use 5 Whys for troubleshooting, quality improvement, and problem solving, but it is most effective when used to resolve simple or moderately difficult problems, and in retrospect (i.e it’s already happened). 

Communicating your framework

A framework is just the logic you use to work through a problem and make a decision. Most of the time, you do this subconsciously. You have frameworks for deciding which parent or friend to call first, where to go for dinner, or what book you want to read next. 

You use frameworks all the time, and it’s just a matter of communicating your thought process to other people. Articulating your framework demonstrates your understanding of the issue to other people, your logic and consistency, and gives people a lot more confidence in your decision making abilities. It also enables your team to make aligned decisions in the future, as your framework for how you got there in the first place is clear.

So when making a decision and communicating that to either your teammates or your manager, you want to share either verbally or in writing, how you went about getting there and the factors you considered. 

It’s important for you to communicate your own frameworks, however, you should also try to get other people you work with to share theirs. Socratic questioning is a great way to do this. This gives you more insight into how others approach decisions, which is valuable for you as you iterate and improve on your own frameworks. 

Have any thoughts, questions or feedback? 👇

Leave a comment

Every week, I write about product, startups, growth, working with people, and anything else that I’ve found helps me have a happier and more meaningful career in product management

If you’re not as subscriber already, join below. It’s free. đź‘‡

If you enjoy this newsletter, and know someone else who also might, you can share it below👇