Deciding when more analysis does not remove uncertainty
More analysis does not always create more certainty.
Trustees increasingly have access to more information, more sophisticated models and AI systems capable of producing detailed recommendations.
But many fiduciary decisions concern a future that cannot be reduced to reliable probabilities: changing family circumstances, competing interests, long-term investments and events that cannot be fully anticipated.
Analysis remains essential.
The harder question is knowing where analysis ends and judgement must begin.
When more analysis cannot remove the uncertainty, what must still come from human judgement?
Some uncertainty can be reduced with better information. Other uncertainty cannot.
John Kay and Mervyn King distinguish situations that can meaningfully be described using probabilities from those in which the possible outcomes, relationships and future conditions cannot be specified with confidence.
In those circumstances, an important question becomes:
What is going on here?
Their work argues that models can illuminate scenarios and assumptions without necessarily predicting what will happen.
Important objectives are not always best achieved by pursuing the measurable target directly.
Obliquity explores how complex goals can sometimes be achieved more effectively through indirect adaptation, discovery and attention to the underlying purpose.
An updated edition, described by its publisher as revised for an AI-driven world, will be published by Profile Books on 19 November 2026.
For trustees, this raises a practical question:
What happens when a measure intended to support good judgement becomes the objective itself?
Other People’s Money asks what financial activity is ultimately for.
Kay argues that capital markets should support capital allocation and stewardship, and criticises a system overly focused on trading, quarterly performance and relative market outperformance rather than long-term relationships with the assets being managed.
For a trustee responsible for wealth across generations, that leads to a different investment question:
How should market performance be used without allowing it to define the purpose of the investment strategy?
How do you distinguish between a decision that genuinely needs more information and one in which further information will not remove the underlying uncertainty?
Radical Uncertainty asks, “What is going on here?” What does constructing a credible account of a family’s situation require, and how should that account be challenged?
From the perspective of Obliquity, what can happen when procedures, indicators or compliance measures become ends in themselves rather than means to a wider purpose?
For a trustee responsible for family wealth across generations, how should market benchmarks and short-term performance measures be used without allowing them to define the purpose of the investment strategy?
A trust holds a significant stake in a family business.
A sale is being considered. Financial analysis produces detailed scenarios and apparently precise probabilities. The next generation is divided. Family circumstances may change, and the consequences of the decision could extend for decades.
What can the analysis tell the trustee?
What assumptions remain uncertain?
And what must the trustee still decide?
Sir John Kay
Sir John Kay is an economist whose career has spanned academia, business, finance and public affairs. He has held chairs at London Business School, the University of Oxford and the London School of Economics, and is a Fellow of the British Academy and the Royal Society of Edinburgh.
His books include Other People’s Money, Obliquity and, with Mervyn King, Radical Uncertainty.
This conversation brings those three perspectives to one practical fiduciary problem:
How should someone entrusted with other people’s assets make responsible long-term decisions when neither markets, models nor more information can remove all uncertainty?
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