What the Work Has Been Arguing
A reader's guide to the ideas and arguments I keep returning to.
Dispatches from an Internet Pioneer is on summer hiatus. A new series begins this fall. The pause is a useful occasion to look back, and this piece gathers what the writing has been arguing across its first year, organized by argument rather than by topic.
The big picture
This Substack began with a commitment. When John O’Brien asked whether I would take on stewardship of the EDUCAUSE CIO Constituent Group, I told him I would, but that I intended to use the platform to advocate for the ideas that more than twenty years as a CIO had brought into focus. Dispatches from an Internet Pioneer is the record of that advocacy. A weekly Substack accumulates arguments whether its author intends it or not, and after roughly a year, the underlying architecture of the writing becomes visible in a way it was not when the project began.
This piece is an attempt to name that architecture, and to organize the existing body of work around the convictions that produced it. Readers who have followed the writing from the beginning will recognize the through-lines. Readers who arrived more recently may find it useful to see them gathered in one place, with specific pieces grouped by the argument they serve rather than by the subject they address.
Nine categories do most of the work. Each is supported by a cluster of articles that develop it from a different angle.
Technology and Society: The Long View
The most durable arguments in this newsletter are not about technology at all. They are about institutions, and about what happens when successive waves of disruption arrive faster than the social structures built to absorb disruption can adapt. These pieces are less about what to do and more about how to see. They situate technology shifts in their full civic context, and they are most useful to readers who sense that something structural has changed but have not yet found a frame for what it is.
Certain About Everything, Agreed on Nothing (May 5, 2026) examines how cable news and the Internet inherited and scaled an outrage model already proven out by talk radio, eroding the relational capital that productive disagreement requires.
Remote Work Will Fast Become Dead-End Work (Feb 3, 2026) argues that as generative AI handles more execution work, physical presence in the institution becomes a structural asset that remote arrangements cannot replicate.
The Weathering Effect (Oct 28, 2025) examines how four successive disruptions have narrowed the imaginative range of leaders who lived through them, and what sustained strategic vision requires in spite of accumulated battle fatigue.
Jobs at Risk, Jobs That Rise (Jun 17, 2025) frames the labor impact of AI as a reclassification of certain types of work rather than a wipeout of knowledge work, with significant implications for how institutions train, hire, and retain staff.
Innovation, China, and the Fair Use Dilemma (May 6, 2025) examines how weakening copyright protections to accelerate AI training risks the intellectual property framework that made the US the home of technology innovation.
From Institutions to Algorithms (Apr 22, 2025) traces how the Internet did not invent the erosion of institutional trust but scaled it, and how generative AI accelerates a shift towards forms of digital certainty already underway.
1993, 2007, and 2022 (Mar 2, 2025) introduces the Substack’s basic frame: three technology shifts follow a recognizable pattern, and the third wave reaches into the production of knowledge itself, each shift accelerating the previous trends.
Technology Strategy and Governance in Higher Education
Technology strategy in higher education fails more often at the governance layer than at the technical one. These pieces are written for leaders who have to make actual commitments about technology investment, tool selection, and institutional governance posture across a range of platforms and decisions, not AI alone. The animating conviction is that the discipline required to govern technology well, resisting hype, maintaining decision rights, sequencing investment against readiness, and holding vendors accountable, is the same discipline regardless of which technology is currently commanding the most attention. AI happens to be the most pressing current example of a set of problems that recur across every technology cycle.
Recap: The Canvas Breach Is Not a Tools Problem (May 9, 2026) argues that SaaS resilience is built through leadership practice and contractual rigor, not through procuring additional monitoring platforms.
When the Code Works But the Decision Doesn’t (Apr 21, 2026) extends the structural diagnosis to generative AI development, arguing that vibe-coding produces individual decisions that work technically but fail institutionally.
Two Kinds of AI Investment and Why the Difference Matters (Apr 7, 2026) revisits the Everyday AI versus Game-changing AI framework in the current spending environment and makes the case for financial restraint at the hype cycle peak.
The Mistake of the Chief AI Officer (Feb 10, 2026) uses Robert Gates’s refusal of the Director of National Intelligence role to argue that creating a Chief AI Officer without budget authority or operational control severs responsibility from power.
Star Quarterbacks and Shadow IT (Dec 2, 2025) names the structural pattern that produces shadow IT units, the technical debt they impose, and why a CIO candidate should treat the pattern as a disqualifying condition.
Everyone’s Using GenAI, Few Admit It (Oct 14, 2025) examines the gap between widespread adoption and public reluctance to acknowledge use as a cultural problem rather than a tool problem.
Building the AI-Infused University Starts with Smarter Compute Investments (Sep 2, 2025) argues that effective AI infrastructure requires orchestrating people, process, and compute together rather than committing to one without the others.
Dopamine-Fueled IT and the Gordian Knot (Jul 22, 2025) identifies the structural conditions that produce fast-build technology strategies and the technical debt they leave behind.
Copilot vs. ChatGPT vs. Gemini (Jun 3, 2025) compares the three dominant everyday AI platforms against learning outcomes, data privacy obligations, and the practical requirements of campus-wide deployment.
Becoming an AI-Infused University (May 27, 2025) offers a practical guide built around the lesson that multi-year technology commitments typically outpace both the maturity of the technology and the institutional readiness to absorb it.
Forget AGI: Worry About What GenAI Knows About You Now (Apr 8, 2025) focuses on the immediate privacy risk of persistent memory in generative AI tools rather than speculative future scenarios.
The Case for Low-Code Everyday AI (Mar 25, 2025) argues that low-code platforms embedded in existing enterprise tools offer a more prudent and scalable path than custom development.
AI in Higher Ed: What Matters and What’s Just Hype (Mar 12, 2025) establishes the foundational distinction between everyday AI and game-changing AI that the Substack returns to throughout.
The AI Economy: The Long View
These pieces step back from the institutional decision and ask the structural economic question: which companies, platforms, and investment theses will survive the current technology hype cycle, and why. The answer turns on vertical integration, marginal cost economics, and the historical pattern of what happens when a technology matures from novelty into infrastructure. These pieces are less about higher education specifically and more about the economic conditions institutions are operating inside, whether they fully understand those conditions or not.
The Long Game: How Google and Apple Are Fast Catching Up in the AI Wars (Mar 17, 2026) argues that vertical integration, device ownership, and marginal cost distribution give the platform companies structural advantages over model labs.
Epilogue 2035: After the AI Bubble (Feb 24, 2026) projects forward from the dot-com bust to ask what will remain of the AI boom once the hype cycle breaks.
Recap: Corning Is the Canary in the AI Coal Mine (Jan 30, 2026) returns to the Corning proxy with fourth-quarter results showing the AI buildout has shifted from GPU procurement to network-layer constraints, a signal that separates real enterprise commitment from speculative capital.
The Real Internet Emerged After the Fall (Jan 20, 2026) makes the central case that the durable innovations of the Internet era were built after the bust, not during the boom, and applies that pattern to current AI commitments.
Recap: AI Bubble? Watch This Innovator for Clues (Nov 14, 2025) establishes Corning's optical fiber demand as a physical proxy for real enterprise AI investment, and introduces Wendell Weeks as the executive whose dot-com era lessons make his current optimism worth taking seriously.
Institutional Failure: A Structural Diagnosis
When something fails inside an institution, my first diagnostic move is structural. These pieces share that analytical method and apply it across a range of settings: service delivery, hiring, governance, and vendor management. The common thread is that behavior which looks like individual failure almost always reflects a system that was designed, intentionally or not, to produce exactly that behavior. Leaders who skip the structural diagnosis tend to intervene in ways that produce no lasting change.
In Defense of Overwhelmed Bureaucrats (Apr 28, 2026) makes the foundational case that when behavior improves with changed incentives, the diagnosis is the system, not the person, and identifies the consequences of skipping that diagnostic step.
Slow Service Isn’t a Capacity Problem (Jan 13, 2026) uses a 32-swimlane faculty hiring process to show that most service failures in higher education are process failures, and that adding headcount to a fragmented workflow produces faster-moving dysfunction.
The Innovation vs. Resilience Dilemma (Jun 25, 2025) offers a framework for the trade-off between chasing early-mover advantage and protecting operational resilience, illustrated through a blockchain moment that tested institutional judgment under hype cycle pressure.
Breaking Scale (Apr 29, 2025) argues that vendor consolidation has crossed into vendor lock-in, that the cloud subscription model has changed leverage dynamics, and that diversification by design is the emerging strategy for sustainable IT operations.
Work Simplification and Operational Discipline
Complexity is the enemy of institutional performance, and simplification is harder than it sounds because it requires decisions about what to stop doing. These pieces share the conviction that no technology investment, however well chosen, delivers its promise inside a fragmented and over-complicated operating environment. Sequencing matters: simplification before automation, diagnosis before investment.
Isaacman’s Inheritance (Apr 14, 2026) uses Jared Isaacman’s confirmation hearing to frame the enduring tension between the discipline of simplification developed in fast-moving private organizations and the constraint structures of legacy institutions.
Understanding the Case for VMware (Sep 30, 2025) analyzes Broadcom’s post-acquisition pricing strategy as a recurrence of the pattern Oracle used after acquiring PeopleSoft, and what intelligent negotiation looks like in response.
A Short Brit, a Big Knife, and a Bold Solution for Technical Debt (Jun 10, 2025) introduces Andy Kyte’s Gordian Knot metaphor to explain why no new system delivers on its promise unless the institution first addresses the complexity it carries into implementation.
The Missing Piece in GenAI’s Economic Impact (Mar 18, 2025) makes the foundational argument that generative AI will not deliver projected productivity gains unless institutions pair it with genuine work simplification.
The CIO Role: Authority, Governance, and Institutional Fit
What the CIO job is, how the authority relationships embedded in the role shape the work, and what distinguishes tenures that strengthen institutions from those that leave them weaker. These pieces are most useful to those early in their CIO tenure, considering one, or trying to understand why a previous one ended the way it did. The reporting line is not a bureaucratic detail. It is a load-bearing element of the role.
Who the CIO Works For Matters in More Ways Than One Would Think (Dec 9, 2025) examines how reporting lines shape the nature of the work in ways that go beyond organizational charts.
A Field Guide to Hiring the Ideal CIO, Being the Right CIO (Oct 7, 2025) offers an honest account of what the position requires and how the fit between leader and institution determines whether the role becomes a tenure or a brief stop.
From the Pentagon to the Provost’s Office (Jul 8, 2025) introduces the Edge-Leverage-Trust model as a principled alternative to both full centralization and fractured autonomy in federated research environments.
Resilience in the Age of Institutional Uncertainty (May 13, 2025) draws on four disruptions across a career to offer a leadership playbook for navigating disruptive change while leading an organization.
ERP and Enterprise Systems as Leadership Development
Large ERP implementations are not IT projects. They are institutional reconstructions, and they expose every weakness in governance, decision-making discipline, and stakeholder alignment that are carried into them. They also compress years of leadership development into a single project, which is why the people who survive one tend to emerge as the most prepared leaders of their generation.
The ERP Contract Doesn’t Run the Project (Mar 24, 2026) argues that consulting agreements define scope and cost but do not substitute for the institutional leadership, decision-making discipline, and vendor accountability that determine outcomes.
Silence Is the Killer (Jan 6, 2026) uses a hospital EHR collapse to identify silence during the design phase as the proximate cause of most catastrophic ERP outcomes, and names the warning signs that a team has stopped surfacing difficult truths before go-live.
The First Six Months Decide Everything (Nov 11, 2025) argues that ERP implementations fail early, quietly, and for the same reason every time: institutions rush past process design to get to configuration.
Why ERP Projects Make Better Leaders (Sep 16, 2025) makes the foundational case that ERP implementations are the most accelerated leadership development environment available to ambitious professionals.
Why ERP Success Starts Outside of IT (Aug 19, 2025) identifies executive ownership outside IT as the single most reliable predictor of ERP success.
Leading People and Building Teams
Leadership is less about vision than about the habits, rhythms, and daily disciplines that develop the people already in the room. These pieces are the most personal in the Substack and share a common conviction: that the capacity to see what a person can become, before they can see it themselves, is the rarest and most consequential thing that any leader can offer. Silicon Valley management playbooks assume conditions that most institutions cannot replicate. Durable leadership starts with an honest assessment of what is actually available and the patient work of building from there.
Leading the Team You Actually Have (Mar 3, 2026) argues that durable leadership starts with an honest assessment of the team in place and the patient work of building capability within real constraints.
Why Your IT Hiring Stalls and How to Fix It (Sep 23, 2025) argues that IT hiring underperforms because organizations screen for credentials rather than competencies, and that building the pipeline internally produces more durable results than the credential-matching approach.
Why We Remember Our Great Professors (Aug 26, 2025) draws the parallel between teaching as sustained investment and leadership as sustained investment in the development of others.
The Unflashy Art of Leading Real Teams (Aug 12, 2025) argues that consistent meetings, regular feedback, and structured communication predict team performance more reliably than visionary leadership.
Seven Lessons from a Cell Door Left Closed (Aug 5, 2025) distills what effective crisis leadership looks like in practice, with attention to what leaders leave behind rather than what they claim in the moment.
Mentorship Is Overrated, Unless You Redefine It (Apr 15, 2025) makes the case that the everyday influence of a great boss matters more than formal mentorship programs.
Negotiation, Trust, and the Currency of Leadership
Negotiation is not a specialized skill. It is the primary medium through which leaders build credibility, resolve conflict, manage vendors, and move institutions. These pieces draw on Chester Karrass, Chris Voss, and more than two decades of practice across every variety of negotiations. The underlying argument is consistent: the leaders who matter most are not the ones who assert most forcefully but the ones who listen most carefully and spend their relational capital with discipline.
What Service Disruptions Reveal (Mar 31, 2026) applies the negotiation styles framework to crisis response, showing how teams that understand their own tendencies respond more coherently under pressure.
Negotiation Styles and the Escalation Ladder (Feb 17, 2026) applies the Assertive, Accommodator, and Analyst framework to team dynamics, showing how the same escalating message lands differently on different stylistic profiles.
The Rhythm of Leading Without Surprise (Jan 27, 2026) makes the case that effective leadership communication is about building information-sharing rhythms that prevent surprise, not about crisis messaging.
Private Truths, Public Leadership (Nov 18, 2025) identifies strategic restraint as a more powerful influence mechanism than assertion.
Know Your Negotiation Style (Nov 4, 2025) introduces the Assertive, Accommodator, and Analyst framework drawn from Chris Voss, and explains how self-awareness about one’s own style converts into durable influence.
Negotiation Is the Leadership Skill (Oct 21, 2025) establishes the central claim that CIO credibility is built less through what gets delivered than through how leaders negotiate to get it delivered.
The Hidden Ladder in Every Negotiation (Sep 9, 2025) names the predictable pattern of negotiation escalation and the responses that de-escalate rather than harden the dynamic.
If You’re Doing Most of the Talking, You’re Losing (Jul 29, 2025) develops listening as the primary tool for uncovering interests behind stated positions.
The Legal Pad That Preserved My Sanity (Jul 15, 2025) argues that note-taking is about retention, not building a reference library, and that handwriting produces a quality of attention and recall that typing cannot replicate.
Extreme Anchors, Empathy, and the Art of Staying in the Room (May 20, 2025) makes the strategic case for empathy-based approaches over short-term extreme tactics.
Extreme Anchors and the Overton Window (Apr 1, 2025) opens the negotiation series by examining how anchoring tactics shift the perceived range of reasonable outcomes before bargaining begins.
Many recap articles and personal reflections are not listed here individually. They do what shorter weekly writing does: situate current events in the broader analytical context, mark passages in the year, and offer the occasional pause between cycles.
The final word
These nine categories do not exhaust what the Substack has been working on, but they account for most of it. They are also more durable than any single technology cycle, vendor transition, or policy environment. The specifics will keep changing. The underlying structure of institutional decision-making, the conditions that produce trust, and the disciplines that make technology investments actually deliver will not.
The original commitment was advocacy for ideas that more than two decades of CIO work had brought into focus. That is still what the writing is for. This work is harder now than it has been at any point in the last twenty years. Changing regulatory incentives, hype cycle pressure, vendor consolidation, and the declining public trust in institutions have combined to produce conditions that reward exactly the kind of restraint, structural diagnosis, and patient credibility-building that the Substack has been arguing for from the beginning. The leaders who will matter most over the next decade are not the ones with the boldest pronouncements. They are the ones who keep doing the work when the excitement fades, and who leave their institutions in better condition than they found them. Everything else is simply commentary.