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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 provide enough evidence to test the assumptions we carried into this year, its time to update the framework used to discuss and plan....
Esteban Kolsky
Analyst Blog
August 26, 2026

Meta Settles Lawsuit to the Tune of $17 Billion: What it Could Mean for Advertisers

Marketing Transformation
Now that Meta has settled what many are calling a quot;landmark lawsuitquot; brought by multiple US states attorneys general, what happens next and how could it impact marketer's plans to engage with younger audiences? From how this could hit the Meta bottom line to how Meta actually maneuvered to protects its revenue ...
Liz Miller
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 18, 2026

Monday's Musings: Future of ERP In An AI Age

Board Strategy
Modernization of ERP Moves Beyond Just Agents While all the buzz in AI is focused on agentic ERP, one can’t just slap on an agent to the core system and expect it to smoothly de...
R "Ray" Wang
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