Mastodon
· A new essay every Monday Sign in Join the Commons
Dr Robert N. Winter For Critical Thinkers
Dr Robert N. Winter Doing Less with More On the Subject of Leadership ·All episodes
Doing Less with More
On the Subject of Leadership · 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.

Member discussion

The Commons

One essay a week, and the argument it belongs to

Free, by email, references included. Sent when it is finished, and not before.

Unsubscribe whenever you like. Nothing is passed to anyone else.

The Inner Circle

Patronage, not subscription

It funds the research and writing directly. What you receive is the work itself: the essays written for it alone, the Canon, and every essay in audio.

Read why it exists

More on Strategy

All in 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 Commons 11 min read

The Price of Everything

The demand to measure the return on our ethics is not a problem to be solved but a symptom to be read. On why pricing virtue corrupts it—and why a firm that can measure the return on its integrity has already begun to spend it.

The Commons 6 min read

The Trouble Was Never the Idea

Generative AI has made plausible ideas nearly free, and a fashionable argument says this changes everything. It doesn't. Ideas were never scarce—judgement was, and remains so. On Grub Street at industrial scale, AI slop, and the only mile that was ever hard.

Free to read Opinion 5 min read

The Books That Don't Balance

Part IV of a IV part series. The organisations capturing real value from AI are not better at AI; they are better at running organisations. The specific moves boards and executives can make to join them—and why nine years of evidence says most will not.

Inner Circle 13 min read

The Permanent Pilot

Part II of a IV part series: twenty-five per cent of organisations have moved AI experiments into production after nine years of trying. Fifty-four per cent expect to within three to six months—a prediction that has appeared in every major survey for nearly a decade.

The Commons 7 min read

Nine Years, One Number

Part I of a IV part series: for nine years surveys have produced a remarkably similar finding: a small minority of organisations capture real financial value from AI; the great majority spend, signal, and pilot.

Free to read 7 min read
Now playing
—
0:00