October 2026: who knows, who's climbing, who's watching, who's carrying what

Who knows how the work gets done

The Insider, Rands in Repose, Oct 20

Every organization has one: the person who knows what to do when the case doesn't fit the process. The organization doesn't know what it knows, and finds out only when that person is out sick or gone. Most managers can name their insider. Fewer have asked what it costs the insider to be the one everyone calls.

Automate work without automating learning, Bertrand Duperrin, Oct 7

The tasks we automate are often the very practice through which people become good at their work. Remove the repetitions and you remove the apprenticeship. We have to preserve learning deliberately, because it won't survive by accident.

The Good Thing About Hard Things, Cal Newport, Study Hacks, Oct 19

In one study, people who used ChatGPT to work through math problems did worse, and skipped more questions, once it was taken away. Read it next to the previous piece. The difficulty was doing the teaching.

On the death of Amazon's writing culture, A Life Engineered, with the Guardian on Microsoft's "doom loop", Oct 13 (both via Bruce Daisley's Make Work Better)

Amazon's practice of reading a written proposal in silence at the start of a meeting was a discipline of thinking, not just a meeting format. AI-generated documents have hollowed it out. At Microsoft, leaders are worried about a loop of low-quality internal documents, and most executives say they see no productivity gains from AI yet. When the document no longer carries someone's thinking, what is everyone reading in silence?

What the structure teaches

Forcing and detouring, Mandy Brown, A Working Library, Oct 21

The career ladder most of us take for granted is a pyramid, with fewer places at each step up, so it manufactures scarcity and losers by design. Some people force their way up; some detour into the dirty work. It's worth asking what your own org chart is teaching the people climbing it.

When Success Becomes the Blindspot, Carl McCann and Shannon Hogan, Drucker Forum, Oct 15

The strengths that got a leader promoted, overused, become the things nobody around them will name. The team sees it, says nothing, and decisions and ideas suffer quietly. Last month we looked at what teams watch their managers do. This is what they watch and don't say.

Don't let your AI dashboard drive your corporate strategy, Ch. Mahmood Anwar, LSE Business Review, Oct 12

Real-time dashboards make it easy to react to every movement, and they push executives into micromanagement. The remedies: filter the data, set thresholds for when to intervene, and run a "human judgement audit." A dashboard teaches you where to look. It can also teach you to stop looking anywhere else.

Two concepts of liberty: what Isaiah Berlin teaches us about self-management, Pim de Morree, Corporate Rebels, Oct 21

Carried into self-management, Isaiah Berlin's 1958 lecture shows that "freedom" is at least two different ideas, and many transformations go wrong because people in the same room mean different things by it. It's a reminder that the words we organize around carry assumptions, and that a philosopher can sometimes see them more clearly than a framework.

Outside the building

Women, Work and Caregiving Through the Arc of Family Life, Pew Research Center, Oct 22

Work and caregiving fit together, and pull apart, across the stages of family life. None of it appears on an org chart, and all of it walks in the door every morning. A manager who knows where someone is in that arc sees a different person than one who only sees the role.

The One Question I Can't Stand at Restaurants, an essay in The Atlantic, via kottke.org, Oct 23

Restaurants keep files on customers and use them to script the seating, the order, the reservation. It's offered as hospitality. The value built into the service is that you are your profile. It's worth asking where our own workplaces do the same to the people inside them.

Whenever you're ready

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