Field notes on moving from AI promise to AI practice. One signal worth following, one subtraction worth making, one (human) prompt worth sharing. Every Monday.
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Newsletter Archive
#051: Permanent = Expired
All information is perishable. AI info ages like milk.
May 18, 2026
#050: 50 Arrows
Nearly one year in, I still don't know what I have.
May 11, 2026
#049: Turnstile or "On The List"?
Stripe shipped agent payments. The language for what agents may do was already open and free.
May 4, 2026
#048: Dashboards Are Last to Know
The question 'what are you doing?' assumes singular attention. Look for what's running, not what fits the dashboard.
Apr 27, 2026
#047: Behind the Wall
David Soria Parra, MCP co-creator, at AI Engineer Europe this week: "2026 is the year agents go to production." Not a prediction.
Apr 21, 2026
#046: Too potent to ship
This isn't a hedge against bad press. This is the team that built the capability looking at the test results and concluding: "uh-oh, this is way too potent for broad deployment right now."
Apr 14, 2026
#045: The Gap Nobody Owns
Right now, somewhere in your organization, four different teams are managing four different slices of AI risk.
Apr 6, 2026
#044: Shared Operational Language
Something quietly shifted in the last year. The format used to describe what a person can do and the format used to describe what an AI agent can do are converging. Same structure. Same questions:
Mar 30, 2026
#043: Skills: Have < Use
Two weeks ago we flagged the vocabulary fork. Last week we showed that skills were never guarantees to begin with.
Mar 23, 2026
#042: Skills Are Bets, Not Gates
Last week we flagged the vocabulary fork: "skills" now means two different things depending on which room you're in.
Mar 16, 2026
#041: Skills Ain't What They Used to Be
For as long as most of us have been working, "skills" meant one thing: what people can do.
Mar 9, 2026
#040: The Verb is the Tell
Listen closely to how people at your org talk about AI. The verb they reach for tells you everything.
Mar 2, 2026
#039: The Rulebook Doesn't Exist Yet
People are asking for AI rules before the rulebook can exist. Rules follow practice. Practice is still forming.
Feb 23, 2026
#038: The Understanding Trap
Last week I wrote about the dangers of saying "not my job" about AI. This week, I promised we'd talk about what to build.
Feb 16, 2026
#037: "Not My Job" is Predictive
When AI adoption hits 'That's not my job,' you're looking at an org design problem, not a skills gap.
Feb 9, 2026
#036: The Weight of Avoidance
You know that feeling when you've been avoiding the bathroom scale?
Feb 2, 2026
#035: The Handoff Gap
AI generates fast. Ownership doesn't scale.
Jan 26, 2026
#034: Rightness at Resolution
AI is right at the wrong resolution -- and your validation infrastructure was built for a different kind of system.
Jan 19, 2026
#033: The Copilot Problem
An ancient failure mode AI is exposing everywhere.
Jan 12, 2026
#032: The One-Hour Year
When individuals outrun institutions, the ground shifts for everyone.
Jan 5, 2026
#031: The Only Skill That Matters
The only skill that matters is not prompting.
Dec 29, 2025
#030: What Survived 2025
Tools changed weekly.
Dec 22, 2025
#029: AI Lives In The Default Path
Most orgs are trying to drive AI adoption with tools, training, and enthusiasm.
Dec 15, 2025
#028: Typecasting L&D as The AI Hype Department
Organizations are asking L&D to lead AI readiness, but what it usually becomes is tool tours, prompting tips, and satisfaction scores instead of real capability.
Dec 8, 2025
#027: Managers over Models
Why your AI strategy lives (or dies) in 1:1s.
Dec 1, 2025
#026: Friction Creates Shape
Here in the US, it’s Thanksgiving week. That means an overload of gratitude posts for all the usual accelerators: breakthroughs, mentors, tools, breakthroughs pretending to be tools. There’s no wrong way to be thankful, but let’s take a different angle.
Nov 24, 2025
#025: Synthetic Trust
We’re moving into a strange era of AI adoption:
Nov 17, 2025
#024: Human Interface Fatigue
_The more “human-friendly” our tools become, the more mental overhead they create._
Nov 10, 2025
#023: Confidence & Calibration
Unpacking confidence saturation in AI, separating smarts from sound, and rewiring rewards.
Nov 3, 2025
#022: Scoring Without Understanding
AI capability numbers are spreading faster than comprehension.
Oct 27, 2025
#021: The PAICE Research Preview Is Live
Yeah, lots happened in the last week (again): specifically over in Anthropic-land where they announced Skills, Web, MS365 integration, and Haiku 4.
Oct 20, 2025
#020: Turbulent Measures
Everyone’s building an AI score right now.
Oct 13, 2025
#019: — Special Edition
Personalization at Scale
Oct 6, 2025
#018: Planning for AI Adoption in 2026
Updating the Diffusion of Innovation model for AI, strategizing for trust-building, and navigating AI adoption hurdles.
Sep 29, 2025
#017: Tools Takeover Talent
Being replaced by AI is optional.
Sep 22, 2025
#016: Talking to AI Like It’s a Computer
Wishing ≠ Collaborating
Sep 15, 2025
#015: AI Breaks the Training Workflow
Parallel or Perish: Rethinking Training for AI
Sep 8, 2025
#014: 5% Success
AI transformation is like baking bread.
Aug 26, 2025
#012: GPT-5 Changes the Game (Mostly Doesn't)
The long-awaited iteration of the model that started the public love/hate affair with AI landed last week. And (predictably) the reaction is still love/hate.
Aug 18, 2025
#013: Security Isn't About Adding More
AI is the world’s fastest amplifier.
Aug 16, 2025
#011: That Funnel of Yours? It's Straining
Your sales funnel is losing leads before any salesperson speaks to anyone.
Aug 7, 2025
#010: Governance is Now a UX Problem
AI is outrunning internal governance frameworks, and the fix starts at the UX layer.
Jul 31, 2025
#008: Align to the Spec, Not to the Prompt
The shift from prompt engineering to spec alignment -- why crafting the spec with care is what actually matters.
Jul 17, 2025
#009: Open, auditable AI stacks just shipped!
Open, auditable AI stacks just shipped. The implications are bigger than the headlines suggest.
Jul 17, 2025
#007: Culture Is a Technical Dependency
Tech teams ship AI features in weeks. The human systems around them still run on quarterly cadences.
Jul 14, 2025
#006: **Signal: Machines With Alien Contexts**
What happens to a custom creative moat when AI can replicate the style in minutes.
Jul 7, 2025
#005: Declare Independence from Vanity Metrics
Dashboards full of vanity metrics create the illusion of alignment -- and AI is making the problem shinier, not better.
Jun 30, 2025
#004: The Org Chart Is Still Fighting the Last War
Org charts were designed for accountability, not adaptability. Agentic AI is exposing that limit fast.
Jun 24, 2025
#003: Tool Choice Is Becoming Strategy
Tool choice is no longer just procurement -- it encodes organizational values, posture, and readiness for change.
Jun 18, 2025
#002: AI Initiatives Are Moving Faster Than Their Organizations Can
AI tools are multiplying fast, but decision rights, governance, and coordination mechanisms are lagging behind.
Jun 12, 2025
#001: The Automation Arms Race Has No Finish Line
Nearly every team is layering 3 or 4 AI tools deep -- but the coordination infrastructure hasn't caught up.
Jun 6, 2025Essays & Notes
Strategic Subtraction: Doing Less to Do What Matters
In a world of complexity, doing less isn't laziness—it's leadership. Here's how subtraction drives clarity and effectiveness.
The Difference Between Strategic Alignment and Decisioning Intelligence
Alignment is table stakes. Intelligence in decision-making is what separates the competent from the catalytic.
Why Governance Breaks Under Pressure
Governance models often fail at the exact moment we need them most. Here's why—and what to do about it.