Why Smart Investors Invest in Reflection

“It matters less that a portfolio manager is right or wrong, rather that they know when they are right and wrong – and in both cases act with conviction by running winners and cutting losers.”

MAN Group, Investing in Skill, 2022

This idea—strong opinions, weakly held—is not just a philosophical quip. It’s the statistical embodiment of an edge.
In investing, what separates good from great isn’t frequency of correctness.
It’s how quickly conviction is updated when the world moves.

But here’s the real kicker: that edge can be cultivated.
Investment skill is not a fixed trait. It’s a function of awareness, behavioural clarity, and reflective processing.
And these can be trained—if you build the right feedback loops.

Skill, Misunderstood

The MAN article challenges a common assumption: that good investors must have high hit rates.
But their data shows something else. The real driver of long-term return isn’t the number of wins—it’s how you behave when you win or lose. Do you cut losers fast? Do you run winners hard? Do you act decisively, not defensively?

That requires clarity in the moment. And clarity under pressure is not something that comes naturally.
It’s learned. Slowly. With structure.

Where Coaching Comes In

This is why coaching—at its best—isn’t about motivation or accountability.
It’s a private lab for building decision-making awareness.

The best investors don’t just want data.
They want to understand what shaped the decision before the data arrived.
They want to spot their blind spots, the emotional charge behind a trade, the unspoken assumptions baked into their frameworks.

Coaching becomes a space where they can:

  • Reconstruct decision chains removing hindsight bias
  • Surface internal rules (“I always cut here”, “I never revisit that”) and test them
  • Notice the emotional triggers that override process

It’s not therapy. It’s cognitive hygiene.

Reflection as Performance Infrastructure

The MAN framework encourages managers to look beyond outcomes, focusing instead on processes and behavioural patterns.
Their use of counterfactuals, trading episodes, and motivation-based analysis is sophisticated. But without regular reflective practice, even this high-quality feedback can land flat. Behaviour doesn’t change just because a spreadsheet says so.

For professionals playing at the elite level, the smallest margins matter.
Coaching introduces a feedback rhythm that keeps attention not just on what happened—but on how it happened, and why.

And when that reflection is structured, it gets internalised.
That’s the path from skill as a metric… to skill as a habit.

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I work with founders, investors, and high-performers who want clarity, momentum, and psychological depth.

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