jasonclewis Operator's Log

Insights / AI Strategy

AI Strategy

10 articles in this topic.

Stylized man in apron carefully tastes steaming contents from a large pot on a minimalist stove.
Jun 17, 2026 9 min read

How Experienced Leaders Decide Where to Bet on AI — and Where to Wait

A three-axis framework — reversibility, time-to-signal, and strategic fit — for making disciplined AI investment calls at any level of an organization.
Miniature person with hammer walks on a green circuit board surrounded by microchips and copper traces.
Jun 29, 2026 10 min read

Build or Rent Your AI Infrastructure? Run the Reversibility Test First

Feature comparisons won't settle build-vs-rent. Estimate the 12-month switching cost for each stack layer — that number makes the call.
A leader filtering a flood of AI news headlines down to a few signal items through a three-question lens
Jun 27, 2026 9 min read

Signal, Noise, and the Things Being Mistaken for Both in AI Right Now

Most leaders are losing the AI cycle by treating every release as signal. A three-question filter — cost curve, work structure, compounding — fixes that.
A stylized man adjusts a large clock, on a minimalist platform with another clock, conveying time management.
Jun 17, 2026 14 min read

Where AI Strategy Goes to Die: The Execution Gap and How Leaders Read It

AI initiatives don't fail in the boardroom — they die in translation. Learn the five structural failure points and how to read the execution gap from your current seat.
A miniature man is overwhelmed, trying to climb a mountain of gray trays cascading down a ramp.
Jun 17, 2026 9 min read

The Second-Order Effects Senior Leaders Watch For Before They Greenlight AI

Most people evaluate AI on first-order wins. Senior leaders are two moves ahead—asking what that win does to the team, incentives, and workflow.
A founder reviewing a blast-radius scoring worksheet that maps a startup's dependence on third-party frontier AI models across continuity tiers.
Jun 16, 2026 10 min read

Frontier Model Risk: How AI-Native Companies Plan for Continuity

Five failure modes, a blast-radius scoring worksheet, and stage-matched continuity tiers for AI companies that depend on models they don't control.
A mid-career professional confidently leading an AI strategy discussion with executives around a conference table.
Jun 10, 2026 10 min read

Becoming the Person Your Organization Turns to on AI — Without 20 Years of Experience

You don't need two decades to become your org's go-to AI voice. You need demonstrated judgment — here's how to show it from your current seat.
A polished slide deck on a boardroom screen contrasted with a handwritten decision list, illustrating the gap between strategy theater and a resourced plan.
Jun 7, 2026 9 min read

Why Most AI Strategies Are Decks, Not Strategies

Most AI strategies get approved as communication artifacts but are expected to deliver as real ones. Here's how to tell the difference in five questions.
Executive reviewing an AI build proposal against a commoditization timeline chart showing shrinking differentiation windows.
Jun 7, 2026 14 min read

How to Tell Which AI Capabilities Will Be Commodities in 18 Months

Four observable signals tell you if an AI capability will commoditize before it ships — and which 30% of the proposal is actually worth building.
A technical contributor presenting at a boardroom table while senior leaders lean in and listen attentively.
Jun 7, 2026 8 min read

Speaking the Language of AI Strategy: What to Say So Leaders Hear You

Your AI input keeps landing as a technical note, not a strategic contribution. One three-move translation framework changes how the room hears you.