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How To Talk To AI
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Every post, in date order.
March 2026
Mar 8
He Said. She Said. It Says.
AI
Human
Leadership
Technology
Mar 7
Scaffolding
Human
Leadership
The250
Mar 6
Crap is Still Crap
AI
Human
Technology
The250
Mar 5
Dunbar’s AI Number and AI’s Dunbar Number
AI
Human
Technology
The250
Mar 4
The Main Thing or the Side Things?
AI
Technology
The250
Mar 3
The Tollbooth
Human
Leadership
The250
Mar 2
My Foundation Shook a Bit
AI
Human
Technology
The250
Mar 1
The Pareto Principle with AI
AI
Human
Technology
The250
February 2026
Feb 28
Just Ask It
AI
Technology
The250
Feb 27
What Can You Imagine?
AI
Technology
The250
Feb 26
The Storytelling of Status
Human
Leadership
The250
Feb 25
What Are We Doing Here?
Human
Leadership
The250
Feb 24
Time Well Spent
AI
Human
Leadership
Technology
Feb 23
Slowing Down to Speed up
AI
Human
Technology
The250
Feb 22
The (Re)Rise of the Specification
AI
Technology
The250
Feb 21
Finding the Problem
Human
Leadership
The250
Feb 20
It’s a Syntax Problem
Human
Leadership
Technology
The250
Feb 19
It’s Time for Middle Management to Shine
AI
Leadership
The250
Feb 18
Brain First. AI Second.
AI
Human
Leadership
The250
Feb 17
How AI Has Effected The250
AI
Human
Leadership
Technology
Feb 16
25000 Prompts In
AI
Human
Technology
The250
Feb 15
Agents Versus Free Agents
AI
Technology
The250
Feb 14
Will AI Unionize?
AI
Human
The250
Feb 13
Heaps of Mediocre
AI
Human
Technology
The250
Feb 12
AI and Zeitgeist (2026)
AI
Human
Technology
The250
Feb 11
What do they want?
Human
Leadership
The250
Feb 10
Drain the Swmp
Human
Leadership
The250
Feb 9
All Things Being Equal
Human
Leadership
The250
Feb 8
A Blip
Human
The250
Feb 7
It’s All Relative
AI
Leadership
The250
Feb 6
The Skeptic Agent
AI
The250
Feb 5
AI and Teaching Intuition
AI
The250
Feb 4
Drinking From The Fire Hose
The250
Feb 3
It’s Time to Find Your Level of Incompetence
AI
The250
Feb 2
Who Are You?
AI
The250
Feb 1
Find the Friction
The250
January 2026
Jan 31
Snow Day
The250
Jan 30
Who is the 1% with AI?
AI
The250
Jan 29
The Uncomfortable Delay
AI
The250
Jan 28
Does It Feel Dangerous?
The250
Jan 27
Humans&
AI
The250
Jan 26
Is It Worth More?
The250
Jan 25
The AI Programmer Debate
AI
The250
Jan 24
Moonshot
The250
Jan 23
Be the Person
The250
Jan 22
To Whom Do You Complain
The250
Jan 21
Exit Strategy
The250
Jan 20
Pop Culture Terminology Vs Professional Culture Terminology
AI
The250
Jan 19
Just Make the AI Work Smarter Not Harder
AI
The250
Jan 18
Is AI Really Increasing Productivity?
AI
The250
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