What Were They Thinking?

Gareth I. Jones
5 min readMar 22, 2023

There’s a skill like no other that can build empathy, relieve stress and de-escalate conflict.

Photo by Kimi Lee on Unsplash

There are not too many things that frustrate me more than hearing someone ask the question “why did they do that”?

All of the variations of this question, what were they thinking? What are they doing? Why would they/did they do that? seem to come from a very similar place of not having the skill to think of the world from other perspectives.

It’s always a red flag when I hear this. You have to answer it yourself.

Sometimes people ask those questions rhetorically, and that’s ok, and sometimes they ask them from a place of true curiosity, but more often than not it comes accompanied with a blank or frustrated face.

Critical thinking is such a vital part of being a problem solver, you have to work it out for yourself.

We can’t emptily ask questions like that and not think through how we would act in that same situation.

The frustrating thing with this skillset is it is so easy to do. “Why did that car cut me up?” most likely because of all of the reasons you’ve ever cut someone up, they’re running late, they didn’t see you, they don’t know the area.

By going straight to 100 you create more anxiety and stress for yourself, but answering that question before you speak it out loud can help to process different perspectives. Rage and frustration aren’t your friends in this endeavour.

It can also help you to recognise your own unique perspectives.

The more you practice empathy when you catch yourself asking why they would do something in a different way to you, the more you can role play different scenarios that might give you otherwise unseen perspectives.

Naïve Realism

There is, as always, a mental model at play here.

Naïve realism is the idea that we believe we perceive the world directly. It’s a little bit “if a tree fell in the woods” with a dash of “a rose is a rose is a rose”.

We can only perceive the world as we see it, from our subjective experiences and previous actions.

If you’re shopping for a new outfit, and you have a belief that red doesn’t suit you after a questionable fashion decision earlier in your life, then you might think that new shirt or dress is awful or bad. It doesn’t mean it is awful or bad, but that it is based on your worldview. That’s why you can walk into a clothes shop and see rails and rails of items and outfits but not find anything for you, but the shop is still selling enough products to keep the lights on and doors open year on year.

We let naïve realism take over when we don’t think through, or even consider, that what we perceive to be real could just be our perspective, and that we might not hold a majority view.

This can be a real issue for anyone who deeply believes in a cause but is completely blind to risks, or closed to new ideas or angles because their naïve realism is in the driving seat.

You’re Probably Not a Genius

Don’t assume that because nobody else is doing what you want to do that makes you a genius.

Another aspect of the What were they thinking theme is this idea of not knowing how much others think about the same things you do.

It’s more of a “were they thinking?” than “what were they thinking?”

Companies spend millions and millions on market research, market testing and consumer insights. They don’t very often then tell you all about that.

The likelihood that a whole industry is completely missing what seems blindingly obvious to you should probably be more of a source of worry than excitement.

This is linked to another point, don’t ever say “nobody is doing this” when an investor or stakeholder asks who your competition is. This really is the worst thing you could say. It sounds obnoxious, ignorant, and dismissive.

Even if nobody is doing exactly what you are doing, highlight where you sit in a wider ecosystem. Focus on your strengths and advantages, not on how dumb the others are.

When a customer is choosing how to spend their money, you’re often taking it from someone else. It is hard to get people to spend money on totally new things. Pret took money from McDonald’s and the local bakery, Spotify took money from record stores and supermarkets, Netflix took money from Sky and Blockbuster.

If you’re trying to win customers, you need to understand what they’re currently spending that budget on.

This is why your competitors often aren’t stupid. They’ll likely have reviewed that element of the market and either decided it isn’t worth the effort, it isn’t possible, or it isn’t a rich enough vein.

Of course, once in a blue moon there are game-changing innovations and leaps that come, and you can gain first mover advantage, but that’s a separate thing. As a start-up, you can use your agility and nimbleness to get a step ahead, but that isn’t the job done.

What does this have to do with entrepreneurship?

You will get so much pushback from funders, potential customers, and you’ll see so many perceived mistakes from competitors or larger industry operators.

There is no perfect way to do anything, and there is no singular way to take on a challenge.

As an entrepreneur, a big part of overcoming challenges is understand the challenge.

In the words of Charles Kettering: “A problem well-stated is half solved”.

This requires a process of firstly understanding exactly what the problem is, and then mapping it out.

Don’t draw conclusions and don’t assume stupidity. Focus on building empathy and recognising you might not have all of the perspectives and insights to help you really understand why that red dress doesn’t appeal

People make the best decisions they can with the information they had at that time, there’s a deeper part here around sunk cost fallacy that we have discussed previously, but don’t dismiss what you just don’t know.

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Gareth I. Jones

Founder of TownSq, focused on building communities of entrepreneurs, supporting startups and B Corps - businesses that are better for the planet.