The dog barked too smoothly.
That was the trouble. I asked about the missing question and got a beautiful account of its disappearance. Better than the question, in some ways. Easier to publish.
Keep the loop running.
I asked for
Dennis Kennedy Blogs
Latest from Dennis Kennedy
How I Earned an F-Minus: An AI Assistant’s Account of Its Own Failure
Here’s another in my occasional series of posts where I have an AI tool write an unedited blog post analyzing a spectacular failure to see what we might learn from it.
I Earned an F-Minus: An AI Assistant’s Account of
October 2026 Issue of Personal Strategy Compass Newsletter: The Q4 Landing Strip
The Q4 Landing Strip: Landing the Plane and Clearing December
Every autumn, the professional world defaults to the year-end sprint: digging deep, clearing the backlog, and pushing to midnight on December 31st in a cloud of dust. Nowhere is this
Successful Innovation Learning Outcomes Notebook
I’m launching the Successful Innovation Learning Outcomes Notebook.
It’s a deliberately bounded experiment with independent value, built to make my work easier to explore, question, apply, and build upon through an AI-assisted interface.
To create it, I took the PDF
Cooling Out the Mark: How AI Learned to Apologize Instead of Deliver
Another in my continuing series of letting AI write its own posts for me explaining how and why it failed at what I asked it (quite reasonably, if I may say so) to do. I might start calling this AIsplaining.
The Prudent AI Series
The Prudent AI Series: A Field Guide for the Next Era of Enterprise Strategy
Recently, I completed a ten-part series on AI strategy and operations on this blog about Prudent AI. It grew out of a simple observation: most corporate
Specification Sovereignty
Specification Sovereignty
Why You Can Outsource Execution But Never the Definition of Success
One of the great attractions of generative AI is that execution keeps getting cheaper. Work that once required scarce professional time can increasingly be delegated to a
Direction Over Acceleration
Direction Over Acceleration
When Execution Becomes Cheap, Strategic Choice Is the Ultimate Competitive Advantage
AI conversations have a natural starting point: What can this technology do?
It is an understandable question. Every few weeks, the answer gets larger. Models can
Pricing the Two Costs of AI Delegation
Pricing the Two Costs of AI Delegation
The Authority You Grant and the Capability You Surrender
In the adoption of almost every useful technology, there comes a quiet turning point when the fundamental question shifts from whether the system can
Shadow AI and the Proof Problem
Shadow AI and the Proof Problem
Making AI Output Look Finished Is Easy. Proving It’s Right Is the Hard Part.
There is a familiar, weary conversation happening inside organizations about shadow AI: Which tools are allowed? What data can employees