Mastodon
· A new essay every Monday Sign in Join the Commons
Dr Robert N. Winter For Critical Thinkers
Topic

Leadership

On judgement, authority, and the exercise of leadership—as distinct from management, and rarely as tidy as the literature pretends.

68 essays · 16 conversations
EssayMonday 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.

Inner Circle 8 min read
ConversationWednesday 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.

EssayMonday 5 October 2026

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 13 min read
EssayMonday 28 September 2026

The Agent That Cannot Answer

An agent, in law and in the older political vocabulary, is someone who exercises judgement on another's behalf and answers for having exercised it. The systems we have agreed to call agents can do the first and not the second, and the evidence on what that costs has started to arrive.

The Commons 11 min read
EssayMonday 21 September 2026

The Appointment and the Fortnight

Someone is promoted, moved sideways in a restructure, or hired in on the strength of a document. Within a quarter the gap is obvious and a fortnight's certification is bought to close it. The evidence says the first move was made on the wrong signal and the second is the weakest remedy available.

The Commons 11 min read
EssayMonday 14 September 2026

What a Certificate Actually Certifies

A certificate records that a person completed a defined process on a defined day. It does not record whether judgement was formed — and in most organisations, nobody is asking the second question, because the first one has tidied the file.

Free to read 9 min read
EssayThursday 10 September 2026

The Chair Against the Wall

Pamela Wyatt says the outsider's job is to adapt, not impose. Then she describes overruling a seating convention, redesigning a room over its users' objections, and building a board pipeline where none existed. The exception is the argument.

The Commons 8 min read
EssayMonday 31 August 2026

Raising the Sea Level

The remedy has no dashboard, vests over years, and mostly benefits your successor—which is precisely why it is avoided. The final essay in the Prior Obligations series sets out what raising the general level of competence actually requires, and why no tool can be bought in its place.

Inner Circle 5 min read
EssayThursday 20 August 2026

Judgement, Not Discipline

Asked to choose between discipline and judgement, David Harvie had just spent an hour describing his disciplines. He chose judgement anyway. On a system that worked exactly as designed, what it cost the people it promoted, and why he has rebuilt a gentler version of it.

The Commons 10 min read
ConversationWednesday 19 August 2026

The Falcon's Club

My guest this week is David Harvie, Director of Wholesale Distribution at AUSIEX, a wholesale broker serving financial advisers and institutions, and the founder of DADBODZ, a health venture for time-poor fathers.

ConversationWednesday 12 August 2026

You Cannot Skip the Stages

My guest this week is Jay Fontanini, founder of the AI Executive Accelerator, who spent three decades in property and casualty insurance before turning to building software and teaching executives to think with it rather than perform having thought.

Now playing
—
0:00