
Thinking beyond AI
As AI begins to offer the promise of answers at scale, the real challenge for leaders is not efficiency but judgment. The ability to critically interpret outputs while navigating ambiguity remains a distinctly creative, human skill.
Leaders are paid to think. Many struggle to find or protect the time it requires. Yet although thinking, the preamble to decision-making, has always been the single most important activity expected from executives, the emergence of AI prompts an array of fundamental, if not existential, questions. When machines can crunch so much data, absorb so much information, work so fast and never get tired, what are the unique qualities that human beings can bring to their work? Does the fundamental task of leadership change and, if so, how? Surrounded by aggressive hype claiming that human capabilities will soon be made redundant by machines, it’s important to keep querying what, in fact, current AI models can and can’t do. How should we think about thinking now?
AI tools have no direct contact with the real world. We do. We don’t consciously notice every detail around us, but we absorb a lot osmotically – just not from behind a desk. This is why the former Bank of England chief economist, Andy Haldane, made a point of escaping his office to walk the streets of London observing, engaging an eclectic range of groups and individuals in conversation. Knowing that, however sophisticated, statistics and economic models couldn’t capture the true complexity of human life, he saw sense-making as fundamental to leadership.
AI tools have no direct contact with the real world. We do. We don’t consciously notice every detail around us, but we absorb a lot osmotically – just not from behind a desk. This is why the former Bank of England chief economist, Andy Haldane, made a point of escaping his office to walk the streets of London observing, engaging an eclectic range of groups and individuals in conversation. Knowing that, however sophisticated, statistics and economic models couldn’t capture the true complexity of human life, he saw sense-making as fundamental to leadership.
AI models rely on static, statistically compressed patterns of data; in a world characterized by uncertainty and ambiguity, this is useful but inadequate. Models deal with the measurable, and much in life can’t be translated into numbers. On a scale of one to 10, how much do you love your child? Your partner? The numbers tell you nothing; self-reporting can vary minute by minute. At work, engagement surveys indicate trends, but in private, seasoned HR professionals acknowledge that they are virtually meaningless. Is engagement up because the sun shone or data was collected on a Friday, or down because it was a Monday? How do you know?
Complex systems may repeat themselves, but not predictably, so patterns can prove to be dodgy guides. Technology easily makes us forget what we know about life – but it is in the life of an organization that leaders must lead. Social context, embodied experience, wisdom over time: None of these are encoded in Large Language Models (LLMs). Uncertainty is one defining quality of human life, poorly represented in AI. All models make assumptions about what good looks like; in technology, this is usually assumed to be efficiency or utility maximization. But these qualities carry risks when too tight margins leave companies without capacity to respond to shocks and surprises. In addition, endemic uncertainty requires that not all choices be defined by the same values, but in LLMs what those values are is frequently opaque.
AI also has an inadequate sense of context, which keeps shifting. There is no data from the future, so AI must work with data from the past. That doesn’t mean it’s useless, but it does mean that it cannot reflect unpredictable shifts in attitudes, possibilities and values. It’s better seen as a provider of options than answers. So it is incumbent upon leaders to understand how, when and where AI is useful and how to interpret and question its outputs. As tempting as it might be to grasp at the machine-generated “answer,” to do so isn’t just an abnegation of responsibility, but a failure to understand leadership itself.
The gold standard of decision-making is the capacity to make choices that even those who don’t agree with them can understand. But how do you explain decisions you haven’t made – and don’t understand yourself? Active thinking, connecting knowledge to the world, is fundamental to trust, timeliness and legitimacy. Being able to think without banisters, to have a conversation with oneself, free of rigid ideologies, assumptions, habits and dogma, is critical for the life of any organization. It is what stakeholders look to leaders for. This may be one reason why, for the last two years, the World Economic Forum’s Future of Jobs Report insisted on the importance of both critical and creative thinking. More than answers, the art of asking great questions becomes paramount to analyze the meaning and consequences of AI “answers.”
“As tempting as it might be to grasp at the machine-generated ‘answer,’ to do so isn’t just an abnegation of responsibility, but a failure to understand leadership itself.”

What might a human ask, but AI might not?
Great questions are critical. They look for what you – or any AI tools involved – may have missed.
What’s wrong with the answer?
What is it missing?
How can we explain it?
Are we taking enough risk?
How much of the decision do we need to make today?
What information or data might change the way we think about this?
If we had more time or money, would this be an adequate solution?
What if we had less time and money?
Who else needs to be in this discussion?
If this went wrong, how would it go wrong?
What else would we need for this to succeed?
Effective questions don’t presuppose binary answers; like a great surgeon, a great question will open up a body of contingencies and possibilities, probing for options and risk. Critical thinkers work from the assumption that there is always more to find, always something missing. This can’t be done alone; leadership thinking still requires the skill to think together, assembling the appropriate array of knowledge, experience, expertise and perspectives around questions that matter. That also requires the capacity to listen and to interrogate. AI, which is morally opaque, demands ethical examination: Without excavation, decisions can be made but their legitimacy will be fragile.
But why the emphasis on creative thinking? Technology frequently renders thinking, products and services generic, undistinctive and uncompetitive, making innovation vital. With AI, strategy becomes, more than ever, an act of imagination. Creative people are often ahead of their times; hence avant-garde. They start from curiosity, noticing anomalies and quirks, with no agenda, cultivating a well-stocked mind. Over time, random data points coalesce around something – an idea, image or sound – and creatives often start work with no plan.
The self-efficacy to find sense and meaning along the way, to invent through experimentation and through discovery, is a rich, adaptive form of sense-making that develops initiative, originality and resilience. Such aptitude, together with a marked reluctance to repeat themselves, enables creative people to respond productively to the unexpected and to drive innovation. Applied to problem-solving, such capabilities may be idiosyncratic, but are the best (and perhaps the only) antidote to the generic nature of technology-driven output. It’s worth remembering that AI was once touted as a quick and easy answer to drug discovery. But the sheer complexity of human biology has disappointed investors.
Leadership once was increasingly technocratic. Now AI challenges us to contain paradoxes: to match urgency with patient questioning, focus with mind-wandering and skepticism with faith, the optimism all leaders must have that they, and those they lead, bring unique human skills to urgent problems and inventions. This shift won’t happen by magic. It will take some thinking …

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