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Analyst Blog
June 19, 2026

The CEO’s AI Dashboard, Part 4: Infrastructure Readiness

I want to move from data readiness to the infrastructure that will determine whether AI can operate at enterprise scale with enough speed, control, and resilience to matter. Infrastructure readiness is often treated as a technology upgrade. It is closer to a long-term operating choice. The enterprise has to leverage wh...
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 it were a cleanup project. It is closer to an operating discipline. Good data helps. Clean data helps. The right data, in the right place, ...
Esteban Kolsky
Analyst Blog
June 07, 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 03, 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 03, 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
Analyst Blog
March 09, 2026

To Succeed in AI, Let The CEO Take Over

Board Strategy
In this issue, we are going to address a slew of articles and research released in the last few weeks that examine who is making decisions about AI adoption in the enterprise....
Esteban Kolsky
Analyst Blog
February 15, 2026

How "Context Graphs" are Redefining the AI Landscape

In this issue, we are going to start – so much to cover – addressing context as the next AI evolutionary hurdle. And no better way to do that than by sharing a few links and ideas ...
Esteban Kolsky
Analyst Blog
February 01, 2026

Is there value for AI after GenAI?

Board Strategy
What happens after GenAI. LLM and GenAI took over in 2025, even “evolving” into Agentic AI. The problem? LLM has limited abilities, like any other single-solution model, and quickl...
Esteban Kolsky