As we assess how AI works, we get a better sense of how our own brains work. To be clear, even the people who create AI don’t quite know how it works, and nobody knows how our brains work.* Today, I want to look into what we mean by exercising “judgement”, whether and how AI can do it, why we’re able to do it, and how we can educate for judgement. I sometimes teach a course on presentations at the University of St. Thomas School of Law. It grew out of a class we ran at CEB, the research firm where I grew up professionally. It was live-fire training intended to help young professionals get better at delivering presentations. The speaker was carrying a message developed and refined by an experienced research team, so they knew what to say – they just needed to get good at saying it. That’s what the training was for. When I first taught the class in a law school, the students were similar – people in their 20s and 30s, college-educated of course, varied backgrounds. As with the corporate course, the core activity was speaking: from Day 1, every student gets up and presents material. And on Day 1, I discovered that this course was going to be about judgement, because the students got up and said things that would get them kicked out of the room – or worse – by a real audience. Real audiences have their own problems and their own perspectives, and the first thing to figure out is not what you’re going to say — it’s what their situation is. It’s the management team of a failing tech company, or the assembled partners of a booming law firm, or a disappointed student activist group, or a church governing board (no adjective necessary: there is always strife). So occupied by the task of presenting material, students hadn’t thought this aspect through. In practice, judgment is asking, and envisioning, how will these people interpret and understand me in light of their situation? What is their situation? Do they agree among themselves on the nature of that situation? (Always: no.) Who do they think I am? Do they have an incentive to agree with my framing of their problem – or to disagree? What does the audience want to hear, and what don’t they want to hear? And finally, the job: in light of all that, what do they need to hear? It is empathy fueled by imagination. If this seems sophisticated, it is. But we start doing it before we can talk, and we keep doing it throughout our lives. Children learn to imagine what Mom wants, and what Dad wants, and what their insufferable older brother and insufferable younger sister want. These imaginings are imperfect but serviceable, and we get a lot better at them over time. They help us navigate. They help us get another Christmas cookie or another story before bed. It’s how we get a date to the prom or a first job or a recommendation from a professor. At CEB, everyone had lived a few years in the corporate world before getting up in front of an audience. We had some experience imagining, based on our experience, what supply chain executives cared about, how that varied by industry and capital structure, how it differed from what their colleagues in Legal or Finance or HR or Strategy wanted. We imagined what they thought of consultants, and young consultants, and young consultants in suits or not in suits, depending on the location. This let us anticipate and manage what this Finance or Legal or Supply Chain executive wanted to hear, and needed to hear. This is judgement. It’s imperfect but serviceable. I did around 800 live presentations, and only faced full audience uprisings in three or four (one of which involved a threat to have me removed by corporate security … we got through it). Sometimes you really don’t get to have the extra Christmas cookie. Back to class - law students don’t necessarily have experience with this stuff, and their first presentations reflected that. Figuring out what to say and how to say it doesn’t leave much brain energy for seeing the six different ways their words could be received by different audience members. Can you teach judgement? Absolutely. As anyone can attest who knew young Danny Currell, I (ahem) didn’t always have it. We get it by putting ourselves in others’ shoes, envisioning diverse “what if?” scenarios, considering alternate outcomes, and doing all of that repeatedly. We build judgement by feeling the effect of mistakes, but more than that — and this is perhaps a hallmark of natural intelligence — we build judgement by correctly inferring effects that we never experience. (I call it natural intelligence, by the way, because animals are quite good at this, too. We’ve had self-driving vehicles since horses were tamed.) In class, developing judgement was mainly about the audience: Who are they? What do they care about? Who’s the decider? Who knows the most? Who’s the most powerful? Who’s the influencer? Who can call corporate security on you? In the event of defenestration, what floor are you on? Yesterday, I wrote about the idea that AI doesn’t have a world-model – only a very sophisticated text string. After that post, an old friend and I emailed about whether it matters that machines currently lack the ability to envision things and to rapidly manipulate those resulting images or mental models like we do. His point is that if AI can use text to describe our mental models accurately and instantly, does it matter if they are one step away from having those models themselves? Let me say why I think it might matter. * Confidence and trust. Part of good judgement is imagining when we are likely to be lied to and why. AI struggles to separate truth from lies, lies from inaccuracies, and lies from fiction. (We know there’s a difference between lies, inaccuracies and fiction. It’s a matter of intention, which that requires empathy to imagine.) If we’re working with AI, at least now we try to mitigate the problem with better prompts. In other words, we supply our judgement. * Empathy and anticipation. Judgement also involves empathy and anticipation. Empathy is “what if I were her?” Anticipation is envisioning what I might do next if I were her. It is alleged that, when asked how to carry out a school shooting, ChatGPT provided a helpful (to the shooter) response. Humans would normally recoil at the question, so it’s worth thinking about why. I think it’s because we instantly imagine why someone would ask such a thing, then – involuntarily, instantly – envision what that person may want to do next. Those thoughts, those world models and their alternatives, form in the blink of an eye. By contrast, at least for now, AI has to run complex calculations to identify a risk, or - as here, allegedly - it just answers the question. How do we teach people to be better at using their natural judgement? It’s a question for the ages, but I think a short piece of the answer is a series of simple questions that are hard to answer: * How do I know? * Who am I dealing with? Are we sure? Are they real? * Who else could I be dealing with? * What might they want? Why? * What’s the best outcome from my perspective? From theirs? * What facts do we probably agree on? * What do they want to hear? What do they need to hear? Am I sure? * Will others accept what I know? Why not? * Who’s getting paid? In the short run – and in the long run? How – and why? * How well does the audience, the author, or my opponent understand their own situation? * How well do we understand our own situation? Do we disagree internally? Why? Tomorrow (post #3) I’ll turn to a related question: what AI, critical thinking, and the liberal arts have to do with each other – and why the answer matters more than most people think. * *On the matter of how our brains work, at least in the terrain we’re talking about here, I think some of the most helpful stuff comes from Iain McGilchrist. Here’s a fun and easy starter video on his ideas. After that, Ways of Attending is terrific. After that, the reading gets a lot longer — The Master and His Emissary at least fits into one volume; his most recent two-volume work, The Matter With Things, I will freely concede I haven’t read yet. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit thecollegequestion.substack.com/subscribe