Five Things

Five ideas or pieces of news that I found around the internet. With a bit of commentary, a link, or a file. A lot of this stuff is from my old blog(s), so some of it is old! But I checked recently, and it's all still pretty up-to-date.

21 posts

Five OD Things N° 13

Company as code; a city is not a computer; AI as cybernetic teammate; a field experiment rewires the org chart; when it starts feeling like a video game

Feb 18, 2026 7 min read

Five OD Things N° 12

Selling personal super-intelligence; trust & safety heading for the exits; raw compute vs. the junk drawer; Wall Street loves shrinking payrolls; the first targets are email jobs

Aug 7, 2025 6 min read

Five OD Things Nº 11

Krugman on enshittification; a mission-driven reset at Microsoft; how Y2K wasn't a thing because of massive multiplayer cooperation; Medium's reboot story; Figma's S-1

Jul 25, 2025 6 min read

Five Org Design Things N° 10

Pattern languages and org analysis; RTO is bad, even if offices are good; old maps made 3D; diverging values worldwide; exit interviews

May 19, 2024 5 min read

Five Creativity Things

Challenges facing creativity; owning ideas from beginning to end; opinionated palettes; are we doing zines again?; randomness that didn’t fit in the first four categories

May 13, 2024 4 min read

Five Org Design Things N° 9

Organizational health essential for firm performance; Avinsa; the heat death of Google; team performance research; platform teams @ PepsiCo

May 5, 2024 5 min read

Five Org Design Things N° 8

Turns out it's about learning, all the way down: How basic technologies shift strategy; Microsoft's org structure research; X-Teams; building Service Design capability; democracy at work

Sep 27, 2023 5 min read

Five Org Design Things N° 7

Collaboration edition! Yumemi’s org design; Collaboration is dead; Elbows of data; How to make good documents; How to run good workshops

Jan 22, 2023 5 min read

Five Org Design Things N° 6

The 95th percentile isn’t that impressive; how DRIs worked at Apple; Effective leaders decide about deciding; Rooting out bias in decisions; AI and interest rates

Jan 15, 2023 5 min read

Five Org Design Things N° 5

Excess management, Big-biz hiring stall, AI for organizing, Issues at Salesforce, and my thoughts on carve-outs 'n' central services.

Jan 8, 2023 5 min read

Five Org Design Things N° 4

Tesla and vertical integration; hotels and the theory of the firm; Shipt dystopia; Range's newest raise; digital service.

Feb 17, 2020 3 min read

Five Strategy Things N° 5

Chick-Fil-A; The Agency Problem; NFL broadcasters; The Unsexy Side of Responsiveness; Amazon Fulfillment Centers

Nov 3, 2014 4 min read

Five Org Design Things N° 3

Conditions for a team; Measuring team effectiveness; Chautauqua; New customer relationships mean new responsibilities; Why do companies exist; The Shift Index.

Oct 28, 2014 5 min read

Five Finance Things N° 1

Handelsbanken; Cross-subsidy; Regulatory capture; The origins of Venmo; Goldman Sachs.

Aug 28, 2014 5 min read

Five Org Design Things N° 2

Expensive communications loops; Edgerati; Leaders are awesome; The purpose of Gawker; Apple's operational effectiveness.

Jun 20, 2014 5 min read

Five Technology Things N° 1

Laws for spacecraft design; Competing with Excel; The original iPhone prototype; Build boring features; Your app is making me fat; Rants on the future of interaction design; Why publishers hate iOS7; Big things start as toys

Mar 26, 2014 6 min read

Five Org Design Things N° 1

Nine barriers to change; Nudges; Scalable learning; Learning at scale; McDonald's & Walmart are software.

Feb 15, 2014 5 min read

Five Strategy Things N° 4

Super Bowl spending; Robots; Defining Strategy; Loyalty Cards r Bad; Disruption & Airbnb; How to win championships.

Jan 2, 2014 5 min read

Five Strategy Things N° 3

Guess the source of this slide; Empathy; Seinfeld on Jokecraft; Flight Manual for the U2; Interestingness defined.

Feb 17, 2013 2 min read

Five Strategy Things N° 2

Why prizes work; Why games are good for the world; Smaller is better; Millennial alter egos; Post-digital briefs.

Aug 12, 2010 7 min read

Five Strategy Things N° 1

Publicness is now free; Influencers are fickle; Moscow traffic; Game designs; Playing time is oxygen.

Aug 7, 2010 7 min read