How Do You Have A Difficult Conversation?

Put It The In The Clouds: Depersonalising Arguments To Make Difficult Conversations Easier

You know the situation: You and your friend are tiptoeing around, or most likely, avoiding any conversation about a sensitive subject—perhaps it’s about a girl/boy you both like, conflicting ideas about what to do next weekend, or which political party should be in power; or something more personal, like why they always get grumpy in the afternoon, why they’re blanking your calls/texts, why they…—because you know that every time you try to talk about it, the result is almost always a fallout. What starts off as a simple conversation quickly turns into a heated, often nasty debate; a personal shot gets thrown in by one party, then the other party cannot help but throw in one of their own; emotions become the dictator of words, not calm, rational, proactive thought. The result: a temporarily-broken relationship; sometimes a permanent one; and sometimes, chairs are thrown.

The main reason this happens is because we become too attached to our opinions, perspectives, ideas, beliefs, hypotheses, and sentiments. That is, because they are products of our own mind, because they are coming from us, we think they are literally us. Therefore when somebody attacks or simply just threatens them, we feel personally offended; and we close up; and we offend back. The Science behind this phenomena is fascinating, and many books have been—and no doubt as the Science improves, will continue to be—written on it1.

The shamefully unscientific upshot, however, is this: It is not our fault, for our brains, by nature, are permeated with cognitive biases and irrational heuristics. One of these is something called the “self-regard,” or sometimes, “overconfidence” bias. In simpler terms: the ego. The ego doesn’t like to be wrong, offended, attacked, or upset; so it is easy to see how most difficult conversations are fruitless, and many turn into arguments.

This problem—an inability to have difficult conversations—is one of the biggest problems we face as a human race. Not only does it get in the way of progress, but the basic maintenance of civilisation. How? Because there are fundamentally only two ways to get things done in the world: with conversation, or with violence. It goes without saying that we want to avoid the latter as much as we can. Sometimes we have no choice, of course; in some instances, violence (e.g. war) is the only option. We are moving further and further away from our beastial roots, but if we are to continue, we must, we absolutely must improve our discourse. And no, it doesn’t start at the state or governmental or public intellectual level (although this is just as important); it starts with everyday conversation; it starts with the people who make the country; it starts with you and I.

This means having those difficult conversations with friends, family, bosses, opponents; and doing so in a manner that is productive. A productive conversation does not have to result in one party changing their mind; it simply has to be rational, logical, well-reason, dispassionate, and unbiased. The best case scenario is, of course, when one party does change their mind — a mark not only of a very fruitful conversation, but of intelligence in the one who ate the slice of humble pie2. For contrary to popular belief, intelligence isn’t about being right, exact, error-free; it is about being rational, open-minded, well-reasoned, informed, logical, practical, and coherent.

Now you may be tempted to say something like “every time I raise the point with her, she just erupts,” or “Johnny is just so sensitive and emotional, and he gets offended at the mention of…” Unfortunately, some people just cannot reason; some people are so irrational, emotional and baseless that the best thing is to avoid conversation with them altogether—that, and give them time to come to their senses. Most people are not this bad, but many do still get offended; and difficult conversation, as a result, can be as painless as pulling your own arms and legs off. Fortunately, there are a few things you can do.

Trying to reason with anyone is a challenge, but it can be almost impossible if the person is not familiar with changing their mind, having difficult conversations, is a child, or is an emotional person. What you can do in situations like this is something I call “putting the argument in the clouds.” It’s pretty self-explanatory, but the basis is this: vividly imagine taking whatever the difficult talking point is, and put it in a cloud above yourselves—and now talk about it. The idea here, is to detach the individual from the talking point, so that nothing said in the conversation about it—the differences in opinion and perspective, the contradicting beliefs, etc—is felt as a personal attack. This is not only a tool for your conversation partner; it is also incredibly helpful for you—no matter how rational you are. Depersonalising the conversation is the goal with this mental exercise; putting the talking point in the clouds is simply a way to facilitate it—it helps you remember, and it makes depersonalisation less, well, personal!

If you think suggesting imaginary clouds to someone would be silly or inappropriate, consider that at the very least it could get a laugh or two. A laugh is always welcome, of course, and could be all you need to make an inescapably difficult conversation that much easier. Further, if you are a parent or teacher, you’ll be surprised at how well kids respond to this technique, too. You do not, however, have to suggest it to anyone at all; you can simply use it yourself.

Not having difficult conversations because they are difficult is not the answer. We must not only continue in our efforts but also increase our skill at having them. The more we shy away from them the more power we give to violence. The more we shy away from getting better at them, the more we stand in the way of progress.


  1. Fantastic books on the influence of biases, subconscious priming, and so on, include: Thinking Fast and Slow, by Dan Kahneman; Influence, by Rob Cialdini; and How to Win Friends and Influence People, by Dale Carnegie.
  2. Remember what F. Scott Fitzgerald said: “The test of a first-rate intelligence is the ability to hold two opposed ideas in mind at the same time and still retain the ability to function.” And he knew a thing or two.

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