Sideways Thought, LLC
Practical technology strategy for complicated human systems.
I help people make better decisions about learning technology, AI, accessibility, web systems, and institutional change. The work is technical, but the goal is practical: decisions people can understand, trust, and use.
Looking sideways, across silos and disciplines.
Sideways Thought is the professional home of Catarino David Delgado: learning technologist, service manager, strategist, web developer, accessibility advocate, and AI educator based in Milwaukee, Wisconsin.
I work where teaching, technology, policy, service operations, and organizational reality overlap. Often, the problem starts messy. Requirements are unclear. Stakeholders disagree. Legacy systems get in the way. New tools create pressure. As a result, the real work is turning complexity into structure people can act on.
Centers of experience
The range is broad, but my work keeps returning to three areas.
Learning Technology and Higher Education
Canvas, D2L Brightspace, Kaltura, Zoom, instructional support, courseware, faculty consultation, digital learning environments, and the institutional structures that make these services work.
AI, Strategy, and Governance
Generative AI literacy, tool evaluation, policy development, classroom guidance, operational adoption, ethical risk, and the workplace effects of emerging technology.
Web, Accessibility, and Systems Work
WordPress, web architecture, accessibility remediation, documentation, service operations, media production, process design, and practical technical implementation.
Credibility
I have spent three decades building, supporting, explaining, governing, and improving technology in education and public institutions. That experience gives me a practical view of what works, what fails, and what people need before they can change.
- Led migrations between Learning Management Systems at-scale for enterprises, not just instruction.
- Administers and coordinates education technology services used at large and medium-sized universities.
- Designed and launched one of the early general education-focused generative AI literacy course efforts in the United States.
- Built and supported WordPress, LMS, media, accessibility, and learning technology systems across the Universities of Wisconsin.
- Works across teaching and learning, information technology, policy, accessibility, service management, vendor review, and institutional strategy.
Good technology work is about judgment, governance, trust, accessibility, documentation, timing, and the people asked to change.
Latest Posts
Essays, models, and working notes on AI, education, learning technology, accessibility, institutional systems, web work, service design, and whatever else needs a sideways look.
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Agents Have Needs Too! How to Successfully Onboard Agents in Your Workplace
Introduction AI agents are becoming more capable, more persistent, and more useful in day-to-day work. Afterall, OpenClaw is to-date one of the most popular agent framework, and open source projects in the world. But OpenClaw, Claude Code, CODEX and other services are not plug-and-play. If an organization wants agents to produce reliable work and reliably…
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Speaking Machine: A Language to Communicate Facts to Large Language Models
The way we talk to large language models needs to change. Fact-RAR is an attempt at describing information to Large Language Models that takes advantage of their knowledge of our languages.
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What If Language Models Could Feel Time? Introducing the Time Token Hypothesis
Technology has long struggled to capture the nuance of how people actually move through the world. Our systems exist outside the flow of time. Sure we have calendars, scheduling tools, timers. But all of those features are designed for us, and are calculated with raw math and complex libraries. But our systems can’t “feel” time.…
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AI’s False Balance: The Truth Problem
Big tech says balance. But when AI treats lies and facts as equal, who loses? The Key Question When Meta announced that its LLaMA 4 model would strive for “balance”—presenting “both sides” of controversial issues—I felt the familiar churn of frustration. The word sounds noble, even responsible. But in practice, this kind of framing often…
Need help with a hard-to-explain technology problem?
I can help organizations, educators, small businesses, and teams make better decisions about learning technology, AI adoption, accessibility, web presence, service operations, and digital strategy. Usually, the hardest problems are not only technical. They are also organizational and human. That is where I am most useful.