First draw two circles
July 8, 2026
What’s funny is that there was no need to be this wrong.
World's Best Newsletter Archive
The next step
June 24, 2026
Most bosses develop an intuition for when something’s brewing.
The wrong tool for the job
June 10, 2026
More difficult. Messier. Slower. These are not selling points.
The last thing you need humans for
April 15, 2026
This is a “what matters is what matters” newsletter.
500 applications, 0 callbacks
April 1, 2026
What if you just abandon the front door entirely and find another way?
Nonsense masquerading as insight
March 18, 2026
Here are three, quick ways to spot AI bullshit in the wild.
Get down off the table, my guy
February 18, 2026
Is this just another hype cycle you can ignore until it dies off? Maybe. But our sense is that this one’s gonna be different.
You are not entirely powerless
February 4, 2026
How do you check power that’s not-presently-checked?
Somebody has to do it
January 7, 2026
We hear this from individual contributors, and we hear it from team leads and line managers, and we hear it from Directors and VPs, too.
The thing that feels better than I told you so
December 10, 2025
Even as we’re setting up something ambitious, we can often spot the things lurking in the shadows that are going to get in the way.
All hat, no cattle
November 26, 2025
If your org is on your seventh layoff or Lord-have-mercy, your 82nd re-org, we suggest that it’s time to take a hard look at your underlying planning issues.
Don’t let the Doerr hit you on the way out
October 29, 2025
The real test for an org is not whether you ever bet wrong. The question is, when the results start to come in, what do you do now?
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