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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 has made an old enterprise technology problem more visible: we continue to measure long-term transformation with tools optimized for shorter-t...
Esteban Kolsky
Analyst Blog
August 30, 2026

A New Way to Look at Enterprise Technology in 2027+

Board Strategy
It may seem early to revisit the enterprise technology framework for 2026 in August, but considering the dramatic compression of cycles, and the fact that the first eight months pr...
Esteban Kolsky
Analyst Blog
August 22, 2026

The Unsung Heroes of the AI Paradigm Shift: CISOs

Board Strategy
I have been arguing for some time that cybersecurity would become one of the largest areas of enterprise technology investment. AI temporarily absorbed much of that budget and atte...
Esteban Kolsky
Analyst Blog
August 12, 2026

Beyond Public Models: The Return of Enterprise Control

The discussion about open-source AI has inherited too much baggage from the software industry. Most executives, technologists, and advisers understand open source through Linux, da...
Esteban Kolsky
Analyst Blog
August 9, 2026

Beyond RAG: Where Enterprise AI Value Will Come From

Data to Decisions
Retrieval-augmented generation (RAG) solved an important early problem for enterprise AI. Large language models could produce useful responses, but they lacked access to current, p...
Michael Ni
Esteban Kolsky
Analyst Blog
August 9, 2026

The Charlatans at the Inflection Point

Board Strategy
Artificial intelligence has crossed enough adoption, investment, and executive attention thresholds to become mainstream, but it has not yet crossed the threshold into predictable ...
Esteban Kolsky