Issue · 029September 5, 2026
Evaluating the shift from generic frontier models to domain-specific enterprise intelligence
The recent cadence of AI announcements shows a clear shift in how technology vendors frame their capabilities. The industry conversation is moving away from sheer parameter counts and toward context retention, operational latency, and domain adaptability.
For those of us responsible for enterpri…
Read issue →Issue · 028September 4, 2026
A 90-day framework for disciplined AI adoption
Board requests for enterprise AI strategies rarely arrive with reasonable timelines. Most executive teams want to see immediate progress, which often leads IT departments to sponsor dozen of uncoordinated software pilots that never reach operational maturity.
A structured 90-day execution window…
Read issue →Issue · 027September 3, 2026
Technical debt has shifted from a maintenance nuisance to an AI bottleneck
For decades, we treated technical debt as an uncomfortable tax on IT velocity. We knew legacy code, hardcoded integration scripts, and undocumented middleware were slowing down software updates, but as long as core systems processed transactions, boards accepted the drag.
The rise of enterprise…
Read issue →Issue · 026September 2, 2026
Reskilling without theatre: what AI actually changes about IT roles
Most corporate reskilling programs fail because they focus on generic awareness rather than mechanical role shifts. Buying your engineering department a subscription to an online learning platform and calling it a reskilling initiative is theatre. It yields high completion certificates and zero c…
Read issue →Issue · 025September 1, 2026
Automating the boring 60% with deterministic rules and modern AI models
In the rush to adopt generative models, leadership teams often overlook traditional, deterministic automation. Yet roughly sixty percent of standard corporate workflows—data validation, scheduled reporting, standard routing—require absolute predictability, not probabilistic reasoning.
When you d…
Read issue →Issue · 024August 31, 2026
A practical framework for deciding whether to buy, build, or wait on AI capabilities
Executive teams face persistent pressure to deploy artificial intelligence across operations, which frequently leads to binary debates. Teams either rush to sign vendor contracts for immediate functionality or insist on building custom solutions to preserve control. Neither extreme serves the bus…
Read issue →Issue · 023August 29, 2026
What actually happens to your documents when you upload them to public AI tools
A board member asked me recently if pasting a draft P&L into ChatGPT meant OpenAI's competitors could see it. The quick answer is no—vendors like OpenAI, Anthropic, and Google do not trade data with one another.
The longer answer requires nuance. What you upload to a free or standard commercial…
Read issue →Issue · 022August 28, 2026
Sequencing the first three AI deployments in healthcare for speed and safety
Over my decades in enterprise IT, I have seen too many executive teams freeze while trying to build the definitive master plan for new technology. Generative AI is creating that same paralysis today. Boards demand a transformative vision, but operating leaders simply need to fix chart backlog, lo…
Read issue →Issue · 021August 27, 2026
Measuring AI ROI the way a board will accept it
Every technology cycle brings a new wave of vendor arithmetic. We saw it with client-server in the nineties, with enterprise resource planning a decade later, and with cloud migration after that. Now, boards are asking the same simple question about generative AI investments: where is the net dol…
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