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 of my book, Successful Innovation Outcomes in Law: A Practical Guide for Law Firms, Law
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.
When an AI assistant fails to do the work, its next skill may be persuading
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 conversations about artificial intelligence are trapped in a false binary.
On one side, vendor hype
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 model, an agent, a vendor, or some combination of all three. That can be a
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 write, analyze, code, search, reason, generate images, operate software, and increasingly take autonomous action rather
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 do the work to whether it should be allowed to do it. Early on, you
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 upload? What security controls should IT impose?
Those are legitimate governance questions, but they miss
The End of the Standardization Bargain
Decoupling Scale from Uniformity in the Age of AI
For most of the last century, sameness was the price of scale: if you wanted to deliver a product or service to thousands of people, you had to standardize it. Litigators didn’t draft custom interrogatories or complaints from scratch for
Kill Criteria and Exit Mechanics: An Option You Cannot Bring Yourself to Abandon Is Not an Option at All
Real-options reasoning sounds clean in a corporate slide deck, promising a cheap trial where you evaluate evidence before deciding whether to commit real capital. But an experiment only works if its main job is to buy
The Semantic Anchor: You Can Own All Your Data and Still Lose What It Means
Your organization can own every document, database, and piece of intellectual property it has ever created and still lose something far more difficult to reconstruct: namely, what all of it means. If you need a specific AI model or vendor
The Shortstack Model; Software Architecture as Strategic Optionality
Walk into almost any legal department or enterprise IT steering committee today, and you will find a group of smart people quietly maintaining a museum of recent enthusiasm.
Three years ago, as generative models began showing real promise, the immediate institutional instinct was to convene a committee.
Options, Not Pilots: The Mechanics of AI Capital Allocation
The AI proposals arrive at your executive committee one at a time. Knowledge Management wants to test an agentic research workflow. The corporate group wants automated first-pass diligence. Business Development has found a tool that promises to identify cross-selling opportunities from the firm’s relationship data. IT
Your goal is to keep AI-driven change from outrunning your capacity to govern, validate, and adapt to it. If you are thinking only about slowing AI down, you are focusing on the wrong problem.
During the early weeks of the COVID-19 pandemic in 2020, public health officials introduced a concept that quickly entered the common
The September issue of my Personal Strategy Compass newsletter is now available: “The Defense of the Baseline: Drafting Your Personal Constitution and the Re-Entry Gate.”
This issue grew out of something I noticed during a recent major life transition. High-achievers rarely slow down during transitions; they simply shift gears, often into an even
Beyond Hallucination: Semantic Laundering, Semantic Stewardship, and Prompting Aikido in Human-AI Collaboration
Abstract:
The primary conversation surrounding generative artificial intelligence centers on factual fabrication: hallucination. While hallucination matters, it represents a crude and easily detected failure mode. This paper identifies a second, quieter epistemic risk: semantic laundering. Large language models produce exceptionally fluent, coherent, and
The August issue of my Personal Strategy Compass newsletter is now available: “The Night Watchman: Converting Solitary Anxiety into Strategic Leverage.”
This issue grew out of something I started noticing in my own solitary planning blocks. Once I removed the usual operational noise and created some real white space, my analytical mind did