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Anthea Roberts is busy reinventing the world of public governance and decision-making for the complex, volatile and uncertain times through which we are lucky enough, in the Chinese proverb sense, to be living. Australian grown, globally nurtured and profound and compelling in every way. Lucky us…
I’ll talk about that work in more detail another time. You can find out more here, here and here. I
Anthea has re-started an earlier series of small essays or longer blog posts exploring different dimensions of her work. This most recent piece poses a question, and offers an answer, to a dilemma that defines much of the contemporary debate about the nature and quality of leadership, especially public leadership and the role and function of institutions.
I’ll give a quick flavour of the argument and some of the insights. The full piece will be published shortly as part of Anthea’s work with Harvard.
Reflecting on her early training in Harvard’s Socratic method as a form of teaching in the Law School – the art of asking questions to discover insight and knowledge – she asks what happens to that approach in the age of AI when answers, give or take the occasional hallucination, are everywhere.
“I’ve been struck by what seems to me like an important realization: we may need to invert the Socratic method again. In the age of AI, where answers are abundant and instantaneous, perhaps the most valuable skill we need to teach isn’t about how to answer questions, but instead how to ask them.”
Remember what the Harvard Socratic dialogue approach was invented to achieve (by Harvard Lw Schol Dean Christopher Columbus Langdell (seriously, what is it with American parents?) in the 1870s.
“It was about cultivating a particular cognitive skill: the ability to probe beneath surface-level answers to reveal deeper questions and tensions. Good law professors don’t just ask questions; they ask the right questions—the ones that expose assumptions, illuminate contradictions, and push thinking forward.”
“Fast forward to 2025” Anthea argues and “we’re witnessing the early stages of an intriguing reversal.” This is the pivot point:
“With generative AI systems that can produce sophisticated answers to nearly any question, the role of question-asker has become increasingly valuable. In a world where answers are readily available, good questions—and the ability to engage in sustained, iterative questioning—have become precious.”
But Anthea’s essay is based not just on the realisation – not brand new of course – that the getting of wisdom is a function of the art of the great question. It’s about recognising that the Socratic method is not just about asking a question, it’s about asking lots of questions to probe, challenge, test and reveal. Like the clever law professor:
“The skilful AI user poses an initial question, evaluates the response, identifies gaps or weaknesses, asks follow-up questions, challenges assumptions, requests elaboration, and gradually refines both the questions and the resulting answers.”
Implications for leadership
There’s a lot of detail packed into the essay. But it lands on three important implications for the way leaders are trained and developed. That process needs to build capability in the art of “iterative questioning”, developing “prompt literacy” and building new “Socratic AI interfaces “
Instead of simply answering queries, these AI systems are starting to ask clarifying questions of their own: “It sounds like you’re asking about X—can you tell me more about your specific interest in this area?” This would model the kind of iterative exchange that characterizes productive human-human dialogue or, as a recent US Air Force Doctrine Note on AI puts it (Doctrine Note 25-1 to be exact), HMT or “human-machine teaming”.
The essay concludes with a timely provocation.
The common thread through these eras – Socrates, Harvard’s law school teaching dialogues and now AI – is “the enduring power of the question mark, the tiny hook that opens minds”:
“As we integrate AI into learning and work, we are all becoming participants in a grand Socratic dialogue with our machines and with each other. This dialogue, when done well, elevates both human and machine thinking beyond what either could achieve alone.”
And then this:
“In an era when advanced AI can answer almost anything, the true art is knowing what to ask. It is not the time to abandon the Socratic method, but rather the moment to invert it—transforming ourselves from answer-seekers into question-crafters, from information consumers into inquiry designers”.
“Inquiry designers”.
Doesn’t that sound like a powerful description of a leadership ethic for these uncertain and complex times? Doesn’t that sound like a basic function of institutions – public, private and civic – that want to claim and sustain their relevance and value? And doesn’t that sound like exactly the right pitch and tone for a leadership model whose defining characteristics are a mix of humble, human and hopeful?
In a world of instant answers, Anthea suggests, “the power of good questions becomes everything.”
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