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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 appropriate until something triggers a review. Authentication has improved, and permissions have become more granular, but the underlying model st...
Esteban Kolsky
Analyst Blog
October 6, 2026

Strategic Optionality for Resilient and Innovative Architectures

Board Strategy
Enterprise architecture has usually moved from one dominant destination to another. Client-server displaced centralized computing, hosted solutions extended that model, and cloud became the target for the last major modernization cycle. Cloud-native emerged afterward to distinguish applications designed specifically fo...
Esteban Kolsky
Analyst Blog
July 17, 2026

The CEO’s AI Dashboard, Part 6: Economics of AI

Board Strategy
I want to focus on the part of the AI discussion that is quickly becoming the least useful and the most necessary at the same time: economics. Most organizations now know they need...
Esteban Kolsky
Analyst Blog
July 17, 2026

The CEO’s AI Dashboard, Part 5: Governance

Board Strategy
I want to focus on the area that will determine how much autonomy the enterprise is actually willing to grant AI: governance. Governance for AI is not an extension of traditional e...
Esteban Kolsky
Analyst Blog
June 15, 2026

The CEO’s AI Dashboard, Part 3: Data Readiness

Board Strategy
I want to move from business value to the condition that usually determines whether that value appears at all: data readiness. Enterprises still talk about data readiness as though...
Esteban Kolsky
Analyst Blog
June 7, 2026

CEO's AI Dashboard Series: Business Value (#2)

I want to start the series with the most abused term in the AI discussion: value. Many enterprises still talk about AI value as though it comes from replacing people or automating ...
Esteban Kolsky
Analyst Blog
June 3, 2026

The CEO’s AI Dashboard (a series begins)

Board Strategy
In this issue, I want to introduce the framework I will use over the next two months to discuss how CEOs can plan, manage, and adjust AI strategy. AI strategy is now sitting at the...
Esteban Kolsky
Analyst Blog
May 10, 2026

Distinguishing AI from Magic

I want to address what we know today about AI (GenAI, more specifically) since the launch of the first commercial GPT nearly 40 months ago. How can we leverage the full strategic ...
Esteban Kolsky
Analyst Blog
April 27, 2026

AI Skills, Part 1: Experience over Expertise

Board Strategy
The market still talks about AI talent as if it were a shopping list of talent that we are seeking. Alas, enterprises should not be looking for a clean inventory of discrete AI ski...
Esteban Kolsky
Analyst Blog
April 10, 2026

Defining What It Means to Have AI Skills (Part 1)

Today, we are going to begin to cover the issue of talent acquisition for AI needs. There is no checklist of skills or talents to use when hiring, nor are there effective tests to ...
Esteban Kolsky
Analyst Blog
April 10, 2026

Revaluing the Human Linchpin in Enterprise Operations

Board Strategy
In this issue, we examine a structural shift in enterprise software emerging across pricing, process design, and workforce assumptions. The focus is not on AI as a generic disrupti...
Esteban Kolsky
Analyst Blog
April 3, 2026

Extracting value from AI? Surely you are joking

In this issue, we explore why AI delivers value unevenly across the enterprise, what is actually working today, and how organizations should approach extracting value over the long...
Esteban Kolsky