Persuasiveness and Truth

When we imagine a skilled leader, we generally expect them to be persuasive. After all, they’ve convinced people to follow them – which itself is an act of persuasion! I think this is true, and not necessarily bad, except for what happens when we start measuring leadership by persuasiveness.

Measuring leadership as a skill is quite difficult – it’s a very fuzzy concept, and all the answers are not necessarily on the surface. The same is true for measuring the value of a company. In the latter case, we often bypass the question by relying on something much easier to measure – the company’s most recent valuation. (This is bad, by the way, but that doesn’t mean it’s not done!) Similarly, team size and morale – a rough proxy for persuasiveness, often more so than genuine leadership skill – is often used to take the measure of a leader.

The problem with this is that, when we talk about skilled leaders, we’re generally after something more than just “someone who right now has many people answering to them.” We’re looking for “someone who can effectively utilize the team they have to achieve broad and complex goals.” And, unfortunately, being too persuasive can actually hurt one’s “true leadership”, despite making them look like an apparently better leader to our broken way of measuring that skill.

How can being more persuasive be a bad thing? Well, it’s a bad thing when your increased persuasiveness leads to you and your team adopting bad strategies more often than not – in other words, when your persuasiveness exceeds your ability to track the truth.

Let’s break this down by looking at the different varieties of persuasiveness.


Storytelling is perhaps the most “leader-y” version of persuasiveness – this is one’s ability to compellingly motivate others. It has no direct relationship to facts, instead focusing on values and vision – what we should strive for, what morals and concepts are important to uphold, etc. It’s a skillset closely tied to political rhetoric – which should probably throw up some minor flags for most of us.

Of course, storytelling isn’t inherently bad at all – in fact, many academics believe this to be the fundamental skill that allowed humanity to form greater-than-150-people-or-so group sizes: the ability to unify around concepts, rather than concrete things. (If you’d like to learn more, I recommend you read Sapiens, which discusses this theory and several other fascinating aspects of humanity in detail.) The challenge of storytelling is simply to make sure that you stand behind it. You’re not making a factual claim, but you are making a promise – you’re promising that you and your team will behave a certain way, will strive for a certain type of thing, etc. As a leader, the more powerful story you’re able to tell, the better – so long as you accept your limits and avoid promising anything you won’t be able to live up to. The moment you begin to overpromise, though, you’re persuading people through deceit, and simply setting yourself up for divisions to form within your team down the line.


Backstopping is the only kind of persuasion which I would argue is “pure good.” This is your ability to summon and convey truths about facts you already understand. In other words, this is your ability to convince others, conditional on your point being objectively true (and on you knowing that’s the case.) This relies on various skills – your memory in recalling salient details, the artfulness of your explanations, and your ability to bridge the inferential gap between your vocabulary and priors, and that of the individual(s) you are speaking to.

I suppose one could argue that one’s ability to transmit true facts could have downsides – for instance, by sharing some true facts but failing to put them into context, one might induce a panic where it’s unwarranted – but I’d consider this an incomplete fact in the first place. In other words, backstopping is not merely about getting the other to agree to repeat your words, it’s about actually getting them to agree with the fundamental idea, seen with all context you see it with. (If you’ve read my recent posts on communication style, this will hopefully be a familiar clarification.)


The last, and most dangerous aspect of persuasion, is conjuring. This is your ability to persuade yourself or others of ideas which you do not yet know the objective truth of. In other words, it’s your ability to argue for a conclusion you are handed, rather than one you have first convinced yourself of. While this may sound like a useful skill, I’d argue it’s really only useful as a proxy for the previous two – yes, this is how “debate” courses work, but they are really trying to test one’s ability to argue for truth, and striving for questions of equal uncertainty to give fair competitive footing.

But in the real world, true wisdom is one’s ability to be more confident about reality than fiction. What this means is that, if you are equally capable of arguing for whatever claim you’re given, you have no wisdom, only clever words. So while the above two types of persuasiveness are generally good and important to foster in a leader, it’s vitally important that they are differentiated from conjuring, and that a good leader recognize the risk of themselves conjuring convincing-sounding “answers” that lead themselves and their teams down a bad path.

Of course, it’s not as easy as simply never conjuring – for an individual, it’s impossible to know the objective truth of a claim with certainty. So one can never truly know if they are backstopping a true claim, or conjuring a nonsense defense. What’s worse, most questions worth debating are hard, in which case the gap in skill levels of two debaters at conjuring may be greater than the gap in the existing evidence – meaning a skilled conjurer can expect to “win” debates with high frequency even if they are right no more often than anyone else. While this is a very tricky problem, if a good leader recognizes that their general “persuasiveness” level is high – and therefore recognizes the risk that they are more likely to “win” through conjuring than most, there are a few techniques they can employ to reduce the risk of “winning” arguments falsely this way.

The problem, of course, is that “truth” is a weak signal. Especially for messy problems, extracting the truth is hard, while constructing plausible-sounding lies is easy. Thus, we expect that most arguments are won more through conjuring than through truth-telling skill, and that deciphering where the truth lies might require some kind of statistical analysis in order to identify the signal from all the noise. But we do make hundreds of decisions daily, so perhaps this means we don’t have to worry? After all, if you have an edge in truth-seeking over others, then even if you’re still conjuring heavily, over a long period of time you’ll be more right than others and so gain an edge. Problem solved, right?

Not really – reality doesn’t grade on a curve. Being more right than the next guy or gal might be useful in a few circumstances, but generally speaking, what matters is simply whether or not you made it across the threshold to “actually correct”, and there’s no law saying that anyone need be able to cross that line. We need techniques to increase our probability of being actually correct – meaning our goal post is set by nature, not our debate opponents.

In this case, you have a few options.

1. Swap sides. If you’re playing both sides of the debate, your “conjuring skill” should cancel out, and all that should be left is the truth on one side or another. Of course, “conjuring skill” is actually dependent on your desires and prior beliefs, so you aren’t actually guaranteed to use as much skill on both sides. This is why I typically prefer…

2. Adversarial collaborations. This is where you partner with someone who starts out on the opposite side of you, and the two of you together work to present both sides of the debate as well as possible. In this case, both sides have someone strongly fighting to defend it and someone weakly fighting to defend it, helping to balance out the arguments. That said, it’s crucial to make sure the two participants are roughly equally persuasive to the population they’re arguing for. So, if you’re a CEO, depending on how your org is run, you might choose another CXO to be your adversarial collaborator; or designate two other execs to work together, if you’re worried your opinion will still be taken with more force than the others’.

3. Bow out entirely. We can expect that people with more organizational power are, in general, more persuasive – not merely due to innate skill (which can be found in anyone), but due to the presence held by someone in a position of power. Thus, it may benefit you to leave the debate up to those who you have less weight as conjurers, and therefore must rely more on fact. Of course, this can backfire if these individuals also lack the full context for the decision, so it must be used carefully. But even then, it can be handy to help you separate your priors from your facts. (Consider a software architect claiming “this is the right way to write code.” Designating two fresh-out-of-school engineers to debate whether you’re right probably won’t convince you of anything – they are both lacking the real-world experience of how different approaches do. But if you let them debate first, you’re more likely to be forced to engage with all the facts on both sides – meaning you’ll layer your experience on top of these points, in contrast to the typical human behaviour of simply trusting your experience without realizing you’re not considering the more salient aspects of the situation.)

4. Keep quotas. This is a finnicky technique, but one that I’ve used to reasonably strong effect. The idea is that you keep a rough count in your head of how many times you “win” versus “lose” arguments around certain types of debates. For instance, let’s say I track discussions with Carter about various aspects of team organization, and find that I “win” 12 and “lose” 4 over the course of half a year. (These numbers are totally made up, by the way.) From the “outside view”, I might have expected ahead of time that I’d maybe win between 40% and 60% of any such arguments – I have no real reason to believe that I’m better at team organization than Carter, say. In this case, as I engage on these conversations, I might realize that I’ve been winning 75% of the time – far more than I would have expected, which means something is likely wrong! In this case, I give myself a slight mental push – telling myself that I must concede a greater percentage of the next few debates we have. I don’t recommend using precise numbers for this so much as feel, but I’ve noticed something interesting when I act this way. Firstly, I’m more willing to concede minor points – which is not only a boost to morale in some cases, but also gives us a chance to actually test both my and Carter’s beliefs on small issues, and so learn if one of us does have more wisdom in a non-destructive way. But secondly, I begin looking for excuses to be wrong – I know I’ll need to lose some arguments soon, so if I’m “using up” one of my wins on this argument, I sure as heck want to make sure I’m right first! This sort of thinking should be done really carefully – remember that this isn’t charity, this is you defending yourself from a known weakness. So don’t be condescending about it, and be wary of overcompensating and becoming underconfident as well – but hopefully thinking about these ideas will at least help you engage more honestly!

5. Constrain the debate. The final tactic is to limit what can be discussed. The ultimate version of this is science’s pre-registered studies, where an experimenter details their plan in such detail that all that’s left is to fill in a few specific numbers from your research – reducing the risk of a biased presentation of the facts. You can replicate this to some degree in business by limiting what you can bring up in a debate – whether by restricting the time you’ll take debating a subject, or, sometimes more fruitfully, limiting word count (if done by email, say) to force each participant to distill the most compelling arguments for their position. Since rhetoric and conjuring typically rely on a lot of talking, this kind of reduction often hurts conjuring-based-claims more than it hurts factual ones, increasing the odds that you consider the right details when making your decision.

On the whole, persuasiveness is definitely a crucial skill for a leader, and one it’s valuable to cultivate. But we must always remember that the goal is not to win an argument – it’s to arrive at the truth. So persuasiveness, like so many things, is only valuable up to the point that it helps us find the truth – and any skill beyond that quickly becomes a double-edged sword.

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