Sports Killed the Player-Coach for a Reason

The Player-Coach Label Is Hiding Three Different Organization Decisions

Sep 21 • Leif Linden

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Who calibrates the person writing your performance review?

The tech industry calibrated its AI judges in eighteen months. The person writing your performance review has never been held to the same standard.

Sep 8 • Leif Linden

A message to modern AI: Welcome to the 1950s

Why the smartest companies won't automate first

Sep 1 • Leif Linden

August 2026

Why role mergers work (and when they don't)

What the DevOps merger got right that AI-driven role mergers are getting wrong.

Aug 14 • Leif Linden

Your AI is overwhelmed, and confused

Pile on context and it forgets; pile on rules and it freezes. The most expensive mistake is reaching for a bigger model when you have an architecture…

Aug 3 • Leif Linden

July 2026

You Can Debug an Agent. You Can’t Debug a Person.

Good leaders read people. Bad managers confuse the person for the tool they already know how to use.

Jul 23 • Leif Linden

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AI Agents Require Operators, Not Just Builders. Get Ready.

Shipping products used to be the finish line. It's now the start.

Jul 16 • Leif Linden

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Testing AI Is Harder Than Ever. Because It's Not a Test.

Most of software never had to grade work with no single right answer. The fields that always did have run this playbook for fifty years.

Jul 9 • Leif Linden

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June 2026

The Dictionary Senior Employees Carry

Corporate language isn't a character defect. It's a sorting mechanism.

Jun 18 • Leif Linden

The specialist PM is having a bad year

AI is multiplying decisions and shrinking the pieces they come in. The single-domain career was built for neither.

Jun 9 • Leif Linden

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Carrying the Bag

The 2026 layoffs assumed AI would replace the work. The survivors are finding out which work it actually can.

Jun 4 • Leif Linden

May 2026

Productivity Is No Longer Free

Per-token prices are falling, yet enterprise AI bills are exploding. Both are true, and the reason rewrites who controls productivity.

May 28 • Leif Linden

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