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Analyst Blog
October 25, 2026

Keeping Strategy Aligned as Execution Accelerates

Board Strategy
I have been thinking about a growing mismatch in enterprise technology. Organizations are becoming much faster at making and executing decisions than at recognizing when those decisions start changing something larger. AI makes the mismatch easier to see, but it did not create it. Cloud, SaaS, APIs, modular infrastruct...
Esteban Kolsky
Analyst Blog
October 12, 2026

Trust, Identity & Control: Every Action Earns Authority

Board Strategy
Enterprise access was designed around a relatively static bargain. Establish an identity, decide what that identity may access, grant the permissions, and assume they remain approp...
Esteban Kolsky
Analyst Blog
September 17, 2026

Business Value and the Limits of ROI

Board Strategy
This is the first in a series looking at a new structure for planning and investing in enterprise technology over the next few years. The introduction can be found here. AI ha...
Esteban Kolsky