How to improve the quality of your thinking and decision making with a few small steps

I’ve had some time off this last week and discovered some awesome podcasts from the Farnam Street podacst (check it out and subscribe!). Shane at FS distils wisdom from smart people into 60–90 minute conversations. The two episodes that got me thinking about thinking (meta -I know) were an episode with Chamath Palihapitiya, and a second with Roger Martin.

[A brief aside on their bios:

• Chamath: early facebook employee, billionaire by age 32, one of the major movers-and-shakers in finance where he is pioneering SPACs, one of which I have invested in.
• Roger: former Dean at the Rotman School at UoT, previously co-head at Monitor Group. Academic expertise includes integrative thinking - rather than choosing between ideas, bring the best of competing ideas together to form better hybrid ideas]

Whilst listening, I was reflecting on my work experience... I’ve been lucky to work with a bunch of people who are really great thinkers. I’ll summarise a few of those traits:

They explore a variety of views: they can almost toss around and manipulate ideas like playthings. Examples include mediating between people that hold strong and opposing views. They just seem able to step out of their own world view to see things from the perspective of someone else.

They make the complex seem simple - ‘nuff said. (I saw a lot of this in some of my most experienced colleagues at McKinsey)

They don’t mind being wrong and they happily change their views: they’re more focussed on getting to the right answer than on what views they held previously or where right answers come from. (I think changing your mind is weirdly looked down on in some environments. If you’re constantly learning, you’re going to change your views about the world on a regular basis. I’d love to see more acceptance of this rather than shaming 🤔)

I wanted to write this piece to organise some of my thoughts following the podcasts, and to create an opportunity for you to tap into some of these ideas without having to listen to the content in full.

Why thinking matters:

Improving your thinking helps you make better decisions. Making better decisions increases the likelihood that 1) you’ll figure out what actually matters to you, and 2) you’ll accomplish more of those things that matter in your life (whether these be career, family, relationships, investments etc).

Where to start: notice your “mental prison”

Everyone has a “mental prison”.

A simple model for a mental prison is to think of it as the constraints in your ability to think. We can break these down into two categories that cover most of these off:

• Biases that skew your perception of the world, by preventing you from seeing a situation for what it is.
• Cognitive tools that enable you to interpret what you see in order to make better decisions

[I’m keeping intelligence out of the conversation here as it’s hard to define, measure and improve]

A quick deep dive on these two categories…

Biases prevent you from seeing things for what they are…

Biases systematically skew how you experience the world.

Understanding your biases helps you remove that skew and see things for what they are. Here are some personal examples:

• Problem orientation: my mind is drawn to problems. I really enjoy finding and solving problems. Sometimes those that work with me find this strange - they may think I’m not enjoying my work because I’m finding problems, or that I think things are more broken than they are (in startups, things are often a bit broken. Prioritising what to work on is the art 🖌). Sometimes those around me would prefer to spend more time reflecting on what’s going well - and I enjoy that too (with a nudge)! 🤣
• Weighting external (expert) voices: I tend to ascribe more weight to a point of view if it comes from an “external” source, and I’ll even weight it even more if the external voice is “an expert”

[Aside: I’ve wondered where these biases come from.. most likely it’s from my background as a physician/surgeon where a big focus of my cognitive training was on diagnosing problems and fixing them. The medical world is also very hierarchical and risk averse, and typically values expertise over creativity]

Being aware of my biases enables me to make better decisions with my team.

… whilst cognitive tools help you develop perspective

Cognitive tools are ways of thinking about a problem. A good “toolkit” will help you resolve complex and messy “real world problems”. Here are some example real world problems to illustrate the point:

• What problems will the biggest companies of the future be solving?
• What biotech platforms will dominate the drug development landscape of the future?
• What will be the role of the middle east in foreign policy when the West no longer relies on fossil fuels?

These are tough questions.

If you can develop an insightful perspective on these questions before others do, and you develop a means to benefit from being right earlier than others, the rewards can be huge. This is because the benefits of being right tend to compound over time. Consequently as time goes on, your gains get larger and larger. These gains might be expertise, impact in your field, the quality of a relationship or financial returns.

For example:

• Spotting how big Amazon was going to be early — not obvious given the eCommerce !@$%show that was the dot-com bubble
• Going long on Tesla when everyone else is shorting the stock
• Sticking with RNA vaccine technology for 15 years, then finding yourself perfectly positioned to run the fastest vaccine development program in human history

(Think about this. You could literally have screwed up your entire lifetime investments with bet after bet in duds like Pets.com or crypto (joke — I’m trolling). But if you put $1,000 into Amazon in 1997 (or $5,000 into Tesla in 2010), they would each be worth $1–2m today. You can be wrong as many times as you like. You only have to be right once about something big.)

The catch here is that it’s generally pretty hard to come up with novel, correct ideas for two obvious reasons. Firstly, if they’re novel, chances are that most people aren’t thinking like you at that moment and you’ll “suffer” in some way before you see any gains (e.g.; being ostracised, ridiculed, ignored etc). Secondly, if they’re correct, chances are that someone, somewhere has had those thoughts before you and you’re not onto something as novel as you might think.

Now that we’ve looked at the benefits of better thinking and discussed two approaches to improving your thinking and decision making, we’ll look at some of the specific tools.

Tools to improve your thinking

There’s a bunch to say here and I’m just going to scratch the surface. Again the Farnam Street blog has a treasure trove of material on this.

The first thing I would suggest to do is develop self awareness about your biases (see above). Ask your colleagues, friends and family for their candid thoughts. (If they don’t give you useful answers, dig deeper)

The benefit here is in knowing where your blind spots are so you can actively work them out of your thought process.

E.g.; If you know that you tend to focus on finding problems, consider carving out time to deliberately reflect on recent wins and their impact when problem solving with colleagues

Beyond this, anyone can start by learning a few simple tools that can be applied pretty much in any situation:

• Take the idea for a walk — put yourself in the shoes of someone with the counter perspective. Listen to their views in order to understand rather than respond. As you develop empathy for their perspective, you’ll build a “3D” understanding of the problem (an analogy here is seeing things from their point of view gives perspective - or depth - to an issue, much like binocular vision generates stereopsis. Sorry, ophthalmology pun 👀). Their point of view might also cover your blind spots (there’s another one 👁️).
• Think through the second order effects — go beyond the immediate consequences to actively consider the consequences of the consequences — i.e.; the second order effects. Consultants often miss this and I think it might be in part because they do so much of their analytical work with MS Excel which is just not useful for modelling second order effects. This essay contains outstanding examples of 2nd (and 3rd) order thinking.
• Invert the problem — ask “How do I achieve the opposite of what I am actually trying to achieve?”. This approach helps you identify how you might fail in pursuit of your goal. It won’t feel natural, but will help you understand the problem better. Plus, it’s easier to avoid failure than to guarantee success. Example here. This is also a fun exercise to do with a product team.

How do you know when you’ve done enough thinking?

I don’t have a good general answer to this (shout if you do!). But one way to think about it is when you are confident that you have a good understanding of what is (and is not) an important factor in the decision. Knowing what is important (and being able substantiate that) is a sign that you are beginning to understand the problem.

What next?

1. Figure out what your biggest biases are and write them down including some suggestions on how to mitigate them. Next time you’re working on a decision, refer to them
2. Check out some of the awesome blogs and podcasts on Farnam Street
3. Try some of the tools suggested above

If this resonated with you, shoot me a DM on Twitter or anywhere else you can find me. I’d love to hear 👂🏼