How to have impossible conversations

In these febrile times, a new book on arguing with empathy is essential reading.

Andrew Doyle

Andrew Doyle


Many of us have seen relationships with friends, family members and work colleagues jeopardised or even destroyed by political differences. In the divisions that have arisen in the wake of the EU referendum vote, or the election of Donald Trump, such concerns are more pressing than ever. Our political climate has reached a point where to disagree politely is seemingly a lost art.

Authors Peter Boghossian and James Lindsay have tackled this problem in their latest book, How to Have Impossible Conversations: A Very Practical Guide. Their concern, quite simply, is ‘how to communicate effectively with people who hold radically different beliefs’. In an era of increasing polarisation, this book could hardly be timelier. Even prominent political commentators now routinely resort to ad hominem attacks and the kind of mischaracterisations of their opponents’ views that would see them fail the most basic course in critical thinking. Rather than just lament the woeful state of discourse, political or otherwise, Boghossian and Lindsay seek to do something about it.

Civil discussion is a skill like any other; it requires a grounding in the basics. Each chapter of How to Have Impossible Conversations moves us forward to potentially thornier encounters – from straightforward disagreements with friends all the way through to rows with closed-minded ideologues. I have long been of the view that trying to reason with racists is futile, because theirs is a fundamentally irrational position. Boghossian and Lindsay have given me cause to reconsider through their meticulous analysis of how such conversations might go in practice. They offer the example of the musician Daryl Davis, who has successfully talked Ku Klux Klan members out of their delusions; they point out that ‘he has a closet full of their relinquished hoods to prove it’. And although I lack the ability or patience to achieve such feats, they have persuaded me that there are those for whom the effort is worthwhile.

For the majority of readers, the most valuable aspect of this book will be how to resolve conflicts of a more quotidian kind. How do we retain friendships in the face of seemingly irreconcilable differences? How do we begin to reinstate the value of discourse when so many prominent figures in the media and the political commentariat are so adamant that their opponents’ views are outside the Overton Window? Having read Boghossian and Lindsay’s cogent guide, I am now more convinced than ever that many of society’s problems could be resolved if we simply learnt how to talk to one another.

First and foremost, we need to consider what we are arguing for. Do we really expect our intervention to prompt some kind of Damascene conversion? Is our intention to persuade or to demean? Boghossian and Lindsay are keenly aware that the purpose of argumentation isn’t always to prove that we are right. There is considerable value in sowing the seeds of doubt in the minds of others. And even the most necessarily robust conversations can be stymied by a lack of empathy or compassion.

The capacity to guide others to the point of introspection is one well worth honing, but we are unlikely to achieve this if our approach is adversarial. This is why the authors offer numerous examples of how conversations with ‘partners’ (rather than ‘opponents’) might be derailed, and how we can best avoid falling into traps. They draw on their own experiences – Boghossian, for instance, has worked with prison inmates to help improve their critical-thinking skills – and are not afraid to cite their own mistakes as examples of what not to do. As they point out, ‘virtually everyone formulates most of their beliefs first and then subsequently looks for supporting evidence and convincing arguments that back them up’. Having the self-awareness to recognise our own flaws is the first step to improving our ability to participate in civil discussion.

The authors advocate a return to the Socratic Method, a drawing out of ideas through the dialectical process. Too often we are guilty of treating an argument as an opportunity to enhance our status, to humiliate our rival, to convey a message, when we should be listening. The sociologist and philosopher Herbert Spencer begins his First Principles (1860) with a reminder that ‘when passing judgment on the opinions of others’, we should be on the lookout for the ‘nucleus of reality’ that lies within even the most flawed proposition. In other words, we have something to gain from listening. This is what Boghossian and Lindsay mean when they suggest that there are times when it is best to ‘switch the conversation to learning mode and ask questions’.

One of the most important lessons of How to Have Impossible Conversations relates to our natural inclination to assume the worst motives in those who do not share our views. Boghossian and Lindsay draw on Plato’s Meno to reaffirm Socrates’ observation that ‘people do not knowingly desire bad things’. We all appreciate how frustrating it can be to have opinions and ideas we do not hold attributed to us by our detractors, so we would do well not to make the same error. ‘If you must make an assumption about your partner’s intentions’, Boghossian and Lindsay write, ‘make only one: their intentions are better than you think’.

This tendency to intuit motive is most commonly showcased on social media, which is as good a reason as any to avoid such platforms when it comes to contentious topics. On a public forum such as Twitter we are essentially performing to an unknown audience, and so disagreements can often escalate into a clash of egos. In such circumstances, emerging as victorious becomes more important than refining our ideas. Boghossian and Lindsay remind us that interactions on Twitter with those who have thrown insults, or who have refused to take one’s arguments in good faith, are rarely productive. ‘The amount of attention you owe anyone who insulted you on social media is zero’, Boghossian and Lindsay tell us. ‘Let them waste their time. Stop playing their game. Block or mute their accounts.’ That is to say, knowing when to walk away is just as important as knowing when to engage.

In lesser hands, this kind of self-help guide could so easily have become an instruction manual for the disingenuous and the manipulative. The authors acknowledge as much in chapter six when they offer advice to the reader whose conversational partner might also have read this book. How to Have Impossible Conversations avoids this pitfall through a continual emphasis on the importance of empathy. By reframing disagreements as collaborative, and urging us to reflect on our mistakes, Boghossian and Lindsay show us the benefits of mutual understanding and sober persuasion. There are few of us who would not profit from reading this superb book. In a febrile political climate, it’s always worth reconsidering our tactics.

Andrew Doyle is a stand-up comedian and spiked columnist. His book Woke: A Guide to Social Justice (written by his alter-ego Titania McGrath) is available on Amazon.

How to Have Impossible Conversations: A Very Practical Guide, by Peter Boghossian and James Lindsay, is published by Lifelong Books. Buy it from Amazon (UK).

Picture by: Getty.

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Tim Wheeler

4th November 2019 at 7:13 pm

This is perhaps not completely in sync with the ethos of the book under discussion but ….. I do like the excellent photo accompanying this piece. The chap with the blue top hat features in the hilarious Alistair Williams YouTube video ‘Everthing That’s Wrong With Remoaners’. Worth checking out for a smile.

Jason Daves

3rd November 2019 at 11:26 pm

“I have long been of the view that trying to reason with racists is futile”

American here: What’s a Racist? I’ve never met one. I’ve only met people with opinions, and all those people are people you can talk and reason with, despite differing views.

nick hunt

3rd November 2019 at 5:19 pm

Both book and review appear to miss a fundamental point: its not everyone who is making rational thought and dialogue impossible: it is the leftist elite. Those commanded by leftist values control the corporate media, government organs, education, and a host of other once apolitical institutions. Leftists today have suffered huge defeats and have subsequently become precisely what they hate: intolerant bigots and elitists. The new master race must nonetheless continue to preach equality to those who think unlike themselves, to free them from supposed inferiority. But real thought and debate are impossible and redundant when dogma and bigotry rule; leftists already know the dumb gammons are wrong.

A Game

3rd November 2019 at 4:23 pm

I suppose the book goes to the place of liberalism: that people have the freedom to think whatever they like about anything and no one else has the right to take that from them. Everyone has the right to disagree and everyone has the right to attempt to convert. But that that attempt shouldn’t be held against them, nor the failure to be converted.
That is the heart of the democratic experiment. Consensus eventually is found in a majority because people want to believe what they want to believe and so its about numbers.
That is what has been lost. The personalising of someone disagreeing with one, that its an insult to them, as a person, if another individual thinks they are wrong, and that because they feel their position is wholesome (and most people, no matter the topic, tend to think that), then its a poor reflection on the character of the person who disagrees with them.
Obviously when they talk about empathy, this is what they are trying to undo. If one person can hold dear an opinion/belief, why can’t someone else hold dear a different opinion/belief.

I read ages ago how sneering at smokers and fat people are now the new vents for people who historically could sneer at the poor or undeducated. You can see Brexit and Trump recreated the ability to sneer at the poor, uneducated all over again. It would seem society always needs someone to sneer at. That this is a middle class hobby… says a lot about them. Twitter is the favourite medium of who…?

That hilarious/pathetic anecdote from the guy who had a relative come and visit who said she voted for Trump… and he freaked out, I can’t remember if he stopped the car and made her get out (a relative visiting from the US in Australia – chivalry is alive and well, right?) or just wanted to. And then he got all big hearted and broad minded and got to know her better and decided to not make her wear a scarlet letter of “S” for scum and find his humanity and forgive her as a person, a relative… grudgingly giving her the time of day as a person, despite voting for Trump. I think she took up the olive branch… I would have shoved where the sun don’t shine, myself.
I can’t remember who it was… but everyone was amazed at the level of arrogant, self importance… the idea that it was okay to indulge hysterical bias towards someone as a fellow human being because they saw something in Trump that this non American voter didn’t.
The writer of the anecdote then expected praise for getting back in touch with his humanity. Bugger that. He deserved exile based on having lost his humanity to such an extent, whilst wrapping himself up in righteousness.

antoni orgill

3rd November 2019 at 3:48 pm

Sounds OK. There seems to be a trend toward elevating talk over action, words over deeds, feeling over fact. Let’s go with the flow and see where it takes us …

Jim Lawrie

2nd November 2019 at 7:53 pm

One acute problem with remainers who refuse to accept the result, and that is who we are talking about, is that they reserve their worst for any remainer who does.

A person who supports revoking article 50 and will attempt no justification is a danger to our society, an enemy of democracy and cannot be reasoned with.

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Ven Oods

2nd November 2019 at 3:19 pm

Having accepted uncomplainingly the result of every referendum and GE for the last umpteen decades, I feel like I should be in line for an award. Then I remember that’s what the majority of people did until 2016, which was probably the high-watermark for general civility in the UK (as it still is for now).

James Knight

1st November 2019 at 4:01 pm

Just another careerist turncoat typical of modern politicians.

George Orwell

1st November 2019 at 1:39 pm

‘Racism’ should be reserved for a belief in inherent genetic differences between races such that on that ground alone a member of a specific race suffers economic loss or physical or mental harm.

It should never be used for scenarios where there are cultural, social and religious differences which lead to different behaviours by individuals within specific racial or ethnic groups in specific situations.

Unfortunately, the latter definition now prevails but it is an abuse of language and logic applied for political purposes.

We should all be entitled to assess our individual compatibility with other individuals on the basis of any cultural, social and religious differences that may exist.

Preventing us from doing so simply drives more people towards genuine racism.

Jim Lawrie

2nd November 2019 at 6:34 pm

That must apply in very sphere of life.

Jerry Owen

1st November 2019 at 8:53 am

A book for many ‘never Trumpers’, feminists remainers SJW’s wokes, and XR fanatics.
Youtube is full of videos showing that these people refuse to engage in any kind of meaningful conversation and indeed get violent when they know they’ve been out debated.


1st November 2019 at 8:32 am

A badly needed commentary.

I have had few conversations about Brexit with determined Remainers and try to avoid them, as I find the total lack of mutual sympathy and understanding upsetting. For the same reason very nearly all online threads are best avoided, as there is rarely anything that can be described as debate on them, only exchanges that are nothing more than typed shouting.

For my part I was keen on the EU until the mid 1990s, when I cautiously looked into how its laws were made. As poorly as I could understand it, there appeared to be nothing that could be reasonably described as democratic accountability about the system, and in any case the democratic element (the European Parliament) was dysfunctional: Europeans do not vote as Europeans, they vote as nationals of their respective countries. When I offer this observation to Remainers their almost invariable retort is: ‘I haven’t got any problem with the EU’s laws’, something that could have (and doubtless was) sincerely expressed by many in Nazi Germany and the Soviet Union. One man only – to his credit – answered ‘I didn’t think of that’, but I doubt that his position has changed.

I think that the great problem with the ‘national debate’ in Parliament and the media is that it is conducted on exactly the same principle as the private and online ones; 99.9% of politicians and commentators take it that the aim is only to ‘win’, not to learn. Furthermore much of the MPs’ nonsense is clearly expressed for party advantage, rather than constructive resolution. It would help if the media, starting with the BBC, would use neutral terminology.I fume when I hear newsreaders saying that the country might ‘crash out of the EU without a deal’ rather than ‘leave the EU without a deal’.

Ultimately, what little consolation there is surely lies in Jonathan Swift’s observation: ‘Reasoning will never make a man correct an ill opinion, which by reasoning he never acquired.’

Incidentally, I believe that the popular definition of ‘racism’ has changed in my lifetime. It now seems to be ‘racial prejudice’, or even any action or opinion that can be thought by anybody else to demonstrate racial prejudice. I try to stick to what I believe is the original meaning, which is that the ‘races’ (themselves a construct as there is only one human race) are so fundamentally different that they should be restricted to different functions in society. That was the way in which Hitler was a racist, but thankfully that opinion is surely as rare as hen’s teeth in Britain today.

John Millson

1st November 2019 at 11:31 am

Neil Datson,
Your observation that so many current politicians are not out to ‘constructively resolve’ is spot on. This means so many of them are directly to blame for our crisis. It surely must be unprecendented. It displays a deep stupidity – political and actual – which we never had before.
Re racism and functions of different sections. Today in the British Isles we have our forbears to blame. Exploitation through Empire/Slavery has poisoned so much of humanity, the immediate victims and those charged to corall and oversee slaves. The legacy remains, arguably. A huge unexhaustive subject obviously…

John Millson

1st November 2019 at 8:13 am

Smart, useful piece.
Hands up: I plead guilty of throwing out unpleasantries on digital forums, which I would never do face to face. Thankfully I am not glued to social media so the showy, gratuitous, ‘Mr Nasty’ falls away pretty quickly when I am back in reality. Have enough basic social skills to have a civil argument, which always ends in peace.
Even though I can’t agree with 75% of the content of sp!ked as I’m unreconstructed,
*non*-Corbynite liberal-left, 2016 Remain voter, I still find it useful and stimulating to read it, even though I know Mr O’Neill online, will always make my blood boil!

Jerry Owen

1st November 2019 at 8:56 am

I agree with some of your self assessment .. you seem happy to call Brexiteers idiots and cockroaches, not a thing most people would say to someone elses face!
There we agree on something at last !!

John Millson

1st November 2019 at 10:06 am

Re Brexiteer ‘cockroaches’ I had in mind well-known leading Brexiteer politicians and agitators. (Borrowed, unwisely, from the book ‘The Cockroach’ by Ian McEwan.) I apologise for any unintended offense given.
The ‘idiot’ put-down was not helpful, no, but then I’m not a ‘little-remainer’! Just another member of the electorate, who does, believe me, accept the result, if not the way some others want it carried out. Just because I ‘lost’ that doesn’t mean I just have to ‘shut up and put up’ with anything. That’s madness and certainly not democratic, in the full accepted sense.
If Cameron, had got off his arse and presented ‘Leave’, with a credible agreement which he had negotiated (aware that the UK could have voted to Leave and so protecting us) or Remain as the options – or, more likely stated at the begining there would be a second, confirmatory referendum on the negotiations outcome – there would not be so much anxiety and fury.
In my opinion a ‘clean’ Brexit is a contradiction in terms. It was always going to be lengthy and untidy. To say that it wouldn’t be was/is the Big Lie or better, the major Cock-up.

Jerry Owen

1st November 2019 at 5:08 pm

John Millson
‘little remainer’ I’m not sure if that’s a general term used by leavers , I think you made it up, anyway hardly cockroach or idiot is it ? Our name for people like you is either remoaners of which you are a perfect example or remainiacs such as Soubry Miller Blair etc. Your side use slurs such as racist, fascist ( Soubry ) zenophobe under educated etc etc.
A clean Brexit isn’t a contradiction, it is what 17.4 million people voted for .
Clean Brexit = leave the EU.
Your problem like so many remainers is you can’t see the big wide world of trade that is to be had, you are inward looking content to stay in a small expensive inefficient struggling club, that clings onto protectionism and tarifs to survive.
Leavers like me see the opportunities waiting to be had outside of the protectionist Empire. You should study the history of this country and you will realize it is a great trading nation.
Of course maybe you are a supporter of Empires in which case i can understand your support for the EU.

Jim Lawrie

2nd November 2019 at 7:04 pm

John Millson you do not accept the result because you think the EU should still hold sway over us.

John Millson

5th November 2019 at 7:59 am

Jerry Owen,

Many no doubt voted for a ‘clean Break’ – obsessive anti-EU moaners – and many voted ‘to take back control’ – habitual non-voters – just wanting to ‘stick it to the Establishment’, duped by Cummings and co.
Hardly a mandate to screw up the economy, security and this country’s international reputation.
It’s a shame committed brexiters cannot reflect. There must be a modicum of common sense somewhere in the collective brexiter brain power.

Stephen J

1st November 2019 at 7:54 am

Surely you mean it is time for a particular section of the community to re-examine their attitude?

I toddled along for over forty years as one who had been divided from the majority because I had voted to leave the EEC in the 1975 referendum. I absolutely didn’t hold it against the winners, they were the winners after all. I did read everything that supported my view and joined my first political party because I held that alternative view.

And then there was another referendum, and this time my side won…

… even though it doesn’t feel like it.

I have little to learn about winning and losing arguments, unfortunately there is a contingent that not only do not accept that they lost, they also all think that they were robbed, that it wasn’t real, and best of all that because we are dumb bovines on the leave side, our votes should not (and do not in their eyes) count.

The reality of course, is that apparently my arguments are spurious, democracy is an unimportant side note of history, and we should all have politics done to us on our behalf by those that are much more intelligent and better educated.

Geoff Cox

1st November 2019 at 7:11 am

By the way, Andrew – you had better define “racists” because under current definitions I am one many times over yet I’d like to think we can have a reasonable conversation.

Lord Anubis

1st November 2019 at 7:54 am

Racist/ism is an “Alice in Wonderland” word. It means whatever the person using it wants it to mean…

John Millson

1st November 2019 at 8:54 am

Best definition: ‘Prejudice plus Power’ even if the ‘powerful’ person has no actual social/economic power.
In so many examples it has to be delusional and pathetic.

Geoff Cox

1st November 2019 at 7:10 am

A couple of comments – firstly I have tried everything with hard core remainers and they will not give an inch. Most rcently, I’ve been defending Jo Swinson over her wildly misquoted comments /meaning about continuing to campaign to remain even if a second vote went against her. But when I ask remainers about the legality of the referendum and say: “I accept the referendum was not legally binding (as none of the other 12 referendums were since 1975), but morally and politically it was binding (like all the other 12 since 1975)”, they won’t give an inch. This is so infuriating – I have no broken off diplomatic relations with my final remainer friend.

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