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.
Articles
Read the work behind the consulting.
Sideways Thought articles turn AI, learning technology, accessibility, and institutional change into models people can use, challenge, and revisit.
AI agents need onboarding
A practical argument for treating agents like new collaborators with context, expectations, and operating boundaries.
Facts need a language
Speaking Machine explores a more structured way to communicate facts and context to large language models.
Truth is not balance
AI systems that flatten truth into both-sides framing create institutional risk, especially in learning environments.
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.
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.