Get New Ideas by Email. Join 3k+ Readers.

How to Pass the Ideological Turing Test

If we believe computer scientist and Turing Award winner Alan Kay, then “a change of perspective is worth 80 IQ points”. To the very least, the ability to see issues from multiple angles is a hallmark of critical thinking. I’ve written about hundreds of concepts on the subject. It’s safe to say perspective change is not only a recurring theme. It’s one of the most valuable skills to develop. We can see the Ideological Turing Test as a measure of said development. Here’s what the test is about, alongside a collection of ideas on how to pass it.

What’s the Ideological Turing Test?

The Ideological Turing Test is a challenge to formulate your opponents’ arguments so convincingly that they think you’re one of their own. It’s modelled on the original Turing Test famously developed by mathematician Alan Turing in 1950. Also known as the imitation game, the test is used to evaluate a computer’s ability to think and mimic humans. A human interrogator would question a computer and another human. But without knowing which is which. Both answer. If the interrogator is unable to tell the difference, the computer wins.

In the age of AI-generated ideas, computers have finally passed the test. AI responses and human ones are virtually indistinguishable. And if we believe OpenAI CEO Sam Altman, AI’s “superhuman persuasion” skills are next on the card, even before it reaches general intelligence. This brings us back to the imitation game of the ideological kind, which pits humans against other humans.

In their paper about the test as a behavioural measure of open-mindedness and perspective-taking, psychologists Charlotte Brand et al. framed the Ideological Turing Test “as a requirement for would-be human debaters”. They asked if participants could “successfully mimic their ideological opponent’s arguments to the extent that their opponent endorses the argument as strongly as their own”.

In general, the researchers found that people were not very good at mimicking the other side’s points of view. But those who did pass were found to be less judgmental and more open-minded. That begs the question of what we can do to master the game and convince our counterparts that we’re one of them.

How to Pass the Ideological Turing Test?

Here’s a collection of ideas and concepts I’ve come across so far that should help prepare us for the Ideological Turing Test.


He who knows only his own side of the case knows little of that.

John Stuart Mill, On Liberty

The first step to passing the ideological imitation game is to understand the concept of steelmanning. Steelmanning is the art of crafting the best possible version of your counterpart’s argument. It doesn’t matter if the other side presented that argument themselves. Assuming you know your own position well, the goal is to fully grasp the entirety of an issue by formulating the best argument your opponents could come up with. If we’re then able to disprove that argument, so the rationale, there’s a good chance we’re close to the truth.

From the Ideological Turing Test-taker perspective, this is a fundamental concept. There’s no point in strawmanning the position so it can be easily refuted. We need to know the actual and strongest position to fool the other side. My steelmanning challenge is one way to apply this principle in practice as a preparation. It’s a three-step method to improve your opponent’s argument, help them to succeed in a debate and even argue on their behalf. To the very least, it should give you a solid primer on what the views of the people you’re aiming to imitate actually are.

Rapoport’s Rules

You can make more friends in two months by becoming interested in other people than you can in two years by trying to get other people interested in you.

Dale Carnegie, How to Win Friends and Influence People

Rapoport’s Rules is a closely related concept that builds on the idea of steelmanning. It was developed by philosopher Daniel C. Dennett as a code of conduct for critical commentary. Dennett himself borrowed from game theorist Anatol Rapoport. The rules set a high bar for rebuttals. Before being allowed to criticise an opponent’s view a commenter must fulfil a few requirements. I paraphrase:

  1. Attempt to re-formulate your counterpart’s position so well and accurately that they thank you because they couldn’t have said it better themselves.
  2. List any points on which you both agree. However, these should not be commonplace claims. They should be propositions of importance and widespread controversy.
  3. Note anything you have learned from your counterpart.
  4. Only if you’ve successfully done the above should you be allowed to voice your criticism.

Rapoport’s Rules asks us to show a genuine interest in our ideological opponent. This gives us a much deeper understanding of them. Of course, for our imitation game, we’d skip part four. But by rephrasing their perspective, exploring our common ground and the lessons we learned from them we can better see the world through our counterparts’ eyes. We’ve gone beyond the mere arguments they bring forward. And we can even go one step further.

Street Epistemology

We take something that you think is true and explore it by asking questions.

Anthony Magnabosco

Street Epistemology is a conversational technique developed by philosopher Peter Boghossian. The goal of the method is to explore people’s most deeply held beliefs. It borrows from our previous methods, such as the emphasis on listening over argumentation and the attempt to look behind the people’s public persona. But it does so in an outspokenly non-judgemental way. By applying Socratic questioning to everyday conversations with everyday people on the street.

The underlying assumption of Street Epistemology is that we’re often unaware of what we believe and why. If we’re being challenged in a non-confrontational manner, we’re able to dig deeper and improve the quality of our reasoning. The same applies to Spectrum Street Epistemology, a debate game that can be played with several people at once. In this variation, players position themselves according to their level of agreement on an issue before being invited to explain their reasoning to each other.

How can Street Epistemology help us pass the Ideological Turing Test? The same way the previous methods can. If our goal is to mimic our opponent’s viewpoints, it’s advantageous to know what they are. The method is an ideal research tool for exploring said worldview. Done right, it peels away another layer as it prompts the players to openly verbalise and question their convictions.

Tactical Empathy

Wittgenstein had an extraordinary gift for divining the thoughts of the person with whom he was engaged in discussion. While the other struggled to put his thought into words, Wittgenstein would perceive what it was and state it for him. This power of his, which sometimes seemed uncanny, was made possible, I am sure, by his own prolonged and continuous researches.

Norman Malcom, Ludwig Wittgenstein: A Memoir

Tactical Empathy is a principle of negotiation developed by former FBI hostage negotiator Chris Voss. In his book Never Split the Difference, he describes it as “understanding the feelings and mindsets” of a counterpart “and also hearing what is behind those feelings so you increase your influence”. As such, Tactical Empathy is yet another sophisticated way to help you understand the other side beyond their arguments. The information you collect can be used to fool them into believing you’re one of them.

Negotiation is very much about gaining an information advantage over others. What do they really want? How do they feel about the other side? What’s keeping them from agreeing to my demands? In his MasterClass course, Voss lays out how mirroring prompts your counterpart to reveal more information. How summarising their position and labelling their emotions gets them to reveal their motivations and potential Black Swans.

Tactical Empathy is ideal for building the rapport needed to win the ideological imitation game. The method also highlights the thin line between putting yourself in the shoes of your opponent and deceit. Between a deep commitment to understanding someone’s potentially twisted worldview and agreement with their values. The good news is that showing empathy does not equal agreement. The even better news is that you can take this approach one step further.

Red Team Analysis

You never really understand a person until you consider things from his point of view, until you climb inside of his skin and walk around in it.

Harper Lee, To Kill a Mockingbird

Red Teaming is perhaps the most comprehensive approach to winning the ideological imitation game. It pretty much unites all of the above approaches into one method. Traditionally, it puts intelligence analysts of one side (the blue team) in the shoes of the red team (their adversary). The goal is to prepare a product indistinguishable from that of the opposition. How would drug traffickers smuggle their contraband? What actions would a foreign power take to undermine a government?

A guiding principle behind red teaming is not only to pretend to be the other side. It is to climb inside the skin of your enemy, decide and act accordingly and then use the findings to outsmart your opponent. To do that, a red team has many techniques at their disposal. Some of these, such as Four-Ways-of-Seeing, you’ll find in my article on Red Team Analysis. Similar to a good undercover agent, red team analysts don’t do acting. They search for the enemy’s character traits, beliefs and attributes in themselves and amplify them.

So if we really wanted to nerd out on the Ideological Turing Test, putting together a red team sounds like the best way forward. Find someone who used to share the values of the other side. Research the other team by employing the tools of Street Epistemology, Rapoport’s Rules and Tactical Empathy. In the end, take what you found and steelman the best possible argument to fool your opponents into believing you’re on the same team after all.

Closing Thoughts

No doubt, Kay’s claim about 80 IQ points is an exaggeration. Changing perspectives won’t boost your innate cognitive abilities. But it certainly makes for better decisions no matter how gifted you are. All you need is a commitment to start observing the world from outside yourself. If you put in the time and effort, you’re not only ready to pass the Ideological Turing Test. It may even change your most deeply held beliefs.