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Dr Robert N. Winter For Critical Thinkers
This week’s conversation Wednesday 7 October 2026

Doing Less with More

My guest this week is Tim Newbold, founder of OKR Quickstart, who has spent a decade watching goal-setting frameworks meet real organisations, and who argues that when they fail, the fault is almost never in the framework.

On the Subject of Leadership
This week’s essay Monday 12 October 2026

Rebuilding the Room

The remedy for a shortage of judgement is not a course in judgement. It is to rebuild the conditions in which judgement is exercised—and to pay the political price of doing so.

The podcast reflection Thursday 8 October 2026
Strategy

The Instrument Is Rarely Blamed

Across seventy-five minutes on OKRs, my guest never once blamed the instrument. On Drucker's forgotten half-phrase, the decisions nobody takes, the arithmetic of slack, and why a target for missing targets is still a target.

The index

Filed by argument, not only by topic

Organisations substitute legible proxies for the unglamorous work of judgement. That single swap produces both the “saviour” they should not have hired and the wasted talent they did. Topics tell you what a piece is about; arguments take you on the journey.

Read by argument
On the Subject of Leadership

Conversations with people who carry responsibility

The conversations that shape organisations usually happen behind closed doors. These are held out loud—on leadership, management, and governance, as they are actually discussed.

All episodes

Doing Less with More

My guest this week is Tim Newbold, founder of OKR Quickstart, who has spent a decade watching goal-setting frameworks meet real organisations, and who argues that when they fail, the fault is almost never in the framework.

Wednesday 7 October 2026
The archive

Recent essays

A new essay every Monday, and the podcast’s written companion every Thursday.

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Governance

Selected for Silence

Some organisations do not merely fail to develop judgement in the people they appoint. They select against it—and in a culture where everyone first-names the chief executive, the selection is almost invisible.

The Commons Monday 5 October 2026 · 13 min read
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