Dispatches from an Internet Pioneer

Lee Silver and the Mystery of the Dead Cat

How reporting lines create a CIO’s context and eventually test their discernment.

Oct 6 • Timothy Chester

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September 2026

What’s the IT Organization for?

How CIOs create value, sustain credibility, and know when friction has a reason.

Sep 29 • Timothy Chester

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The AI Phantom Menace

The frontier laboratories are entering university research fields. Faculty and staff need guidance about what knowledge they place in those systems.

Sep 22 • Timothy Chester

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More Than the Loudest Story

Why CIOs need a shared account of how the institution experiences technology.

Sep 15 • Timothy Chester

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Separated Siblings, Reunited

An open letter to the boards of EDUCAUSE and Internet2 from a member of the generation that helped higher education put the Internet to work.

Sep 8 • Timothy Chester

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Does Your ERP Project Need a Star Quarterback?

Why universities should purchase implementation expertise while keeping leadership with those who hold the institution’s trust.

Sep 1 • Timothy Chester

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August 2026

Lou Mannheim on AI Credit Risk

What hidden debt, private doubt, and disciplined suppliers can teach higher education.

Aug 25 • Timothy Chester

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AI Governance Is a Human Judgment Problem

A practical framework for personal AI, institutional protection, and taking Microsoft Copilot seriously again.

Aug 18 • Timothy Chester

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The Director of Central Computing

Managing the central IT organization is a real job. Governing technology across a research university is a different one.

Aug 11 • Timothy Chester

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Requestor Name Goes Here (Requestor Department Goes Here)

Why a requirement attached to a department instead of a person becomes an ERP risk no one can negotiate.

Aug 4 • Timothy Chester

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June 2026

Apple Just Settled One Question. Microsoft Opened the Other.

A week of announcements has clarified where everyday AI best lives. The institutional contest is just beginning.

Jun 15 • Timothy Chester

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May 2026

What the Work Has Been Arguing

A guide to the ideas and arguments I keep returning to.

May 25 • Timothy Chester