Leadership ‘mastery’ in an AI world
23 December 2025 — In this blog, Dr Louise Drake explores how AI is reshaping leadership mastery and challenging traditional expertise. She argues that judgment and human connection are essential in an AI-driven world. CISL's postgraduate courses help develop the critical thinking, clarity of purpose, systems insight, and contextual awareness needed to navigate complexity.
Leadership ‘mastery’ in an AI world
It is no understatement to say that ‘mastery’ is being profoundly transformed through AI. What people spent decades mastering in terms of specific skillsets and expertise, can now be done in a matter of seconds. For many, AI represents not just economic upheaval but a fundamental crisis of identity. It also poses a critical question for CISL postgraduate education because the ambition of Master’s-level courses – in this case leadership and sustainability for business and the built environment – is to develop ‘mastery’: lifelong capabilities rather than a static level of expertise.
As CISL CEO Lindsay Hooper comments in a recent blog, AI is not simply another technology wave; it is reorganising the strategic conditions under which societies plan, invest, compete and govern. Individuals and organisations will need to understand and navigate the structural shifts that AI will accelerate. The ability to do so will not automatically be found in the information or analysis that AI offers in abundance. Rather, it will be found in using AI’s insights with wise judgement, and building meaningful connection with others.
Leadership judgment
Psychiatrist and philosopher Iain McGilchrist argues that modern AI development exacerbates an existing over-dependence on a narrow, mechanistic, analytical left-hemisphere mode of thinking.[i] We risk neglecting a right-hemisphere mode of thinking that is broad, contextual, holistic, and generates meaning.
Four capabilities core to our curriculum help develop wise leadership judgment:
Critical thinking. Critical thinking is especially important when it comes to AI, because what might appear to be ‘plausible content’ will in fact reflect a pastiche of assumptions and assertions, not all of which have strong foundations and some of which might have significant blind-spots and biases. Critical thinking examines the assumptions that underpin knowledge, rather than accepting it at face value, developing the capacity for contextually sensitive, evidence-based decision-making.
Clarity on aims and goals. AI offers unparalleled potential to achieve what we ask of it. But as cybernetics founder Norbert Wiener warned:
"If we use, to achieve our purposes, a mechanical agency with whose operation we cannot interfere effectively …we had better be sure that the purpose put into the machine is the purpose which we really desire."[ii]
AI is much more than a machine; it represents transformative potential at an unprecedented speed and scale. Critical reflection on the ultimate ‘good’ we are in service of (and for who) – as individuals, organisations and societies – is essential. Robust debate across diverse global cohorts is enriching and clarifying, laying a solid foundation for the inevitable future judgments required at speed in a rapidly changing context.
Choice scaffolding. For many years, our CISL educational programmes have developed ‘systems intelligence’ – understanding complex problems by focusing on the interconnections within a whole system. AI goes beyond human capacity for systems thinking with its ability to process vast amounts of data, but what matters is how this systems insight informs leadership choices. Our course directors come from vastly different disciplines, each bringing unique insights into how we understand systems, frame problems, weigh-up decision-criteria, and approach potential trade-offs within complex systems.
Contextual insight. Context is core to human judgment, which is why all our postgraduate assignments are based on students’ lived realities – identifying leadership challenges or opportunities in their situation (a number of which recently have been on the intersection between AI and leadership). AI is developing in its capacity for contextual analysis, but much available data remains decontextualised and generative AI is not yet able to infer context. Human leadership therefore remains critical for bringing context and qualitative reasoning into decision-making.
Leadership connection
A computer … has no capacity to feel love, excitement, compassion, or to dream of doing something other than what it was programmed to do. It has no imagination. It cannot motivate, inspire, or instill a desire to serve others. “It in in this uniquely human potential for growth, compassion, and love where I see hope”.
Interview with Dr Kai-Fu Lee, former president of Google China
Meaningful connection is critical for building our shared capacity to live well together in an age of AI, and there are three distinctives that underpin its development in our programmes:
- Community. Our students join us, not as individuals, but as part of a diverse leadership community. You only need to read a few of our ‘day in the life’ accounts to see an appreciation of the shared experience and wisdom in every cohort. The group research component accelerates vital skills development in team leadership. I have witnessed students’ ongoing support for each other many years beyond the formal end of a programme – connections that will be vital in navigating future waves of change with wisdom.
- Confidence. It is easy to think of examples where audacious ‘confidence’ has wreaked havoc, but a respectful, grounded confidence that is able to connect well with different people is going to be increasingly important as AI potentially exacerbates existing social divides. Over the last year we’ve focused especially on building students’ confidence to work cross-culturally, and connect with others in compelling and impactful ways.
- Commitment. ‘Accepting responsibility’ is core to our definition of leadership, and flows from being connected enough to a place, organisation, or community to take a leadership ‘stance’. Whilst the pace of AI development is outgrowing existing accountability structures, it is critical that we doesn’t resign ourselves to powerlessness. We’ve found that our learning approach has nurtured an extraordinary level of leadership commitment over the years, and we continue to experiment with innovative approaches to nurture this sense of accountability.
Earlier this week, a senior Hong Kong business leader who had just finished his Master’s gave me some impromptu feedback. During his first week in the programme, he was concerned we weren’t providing clear answers. He had expected Cambridge to offer ‘silver bullets’ to his leadership challenges.
Two years on, he reflected on how profoundly the course has influenced him, giving him confidence and a renewed mindset: