Triangulating for Truthiness

Effective Engagement with LLMs for Software Development and Operations

Working effectively with large language models requires something that the speed and fluency of those models can easily obscure: rigorous human judgment. In this paper, Jonathan Snyder argues that LLMs are not deterministic systems—they operate on statistical probability, not hard logic—and that this makes them, without proper guardrails, a source of systemic risk in software development and operations. The antidote is not to use them less, but to govern them more deliberately, treating the human operator as the accountable epistemic anchor and the LLM as a well-informed contributor whose outputs are always hypotheses until proven otherwise.

Drawing on his own experiments refactoring a React application with LLM assistance, Snyder offers a set of concrete principles for effective AI collaboration: codifying architectural specifications as the source of truth, applying the five whys in a data-driven, staged approach, using automation as an Andon cord that halts work when AI-generated changes exceed what testing can safely evaluate, and resisting the "vending machine" prompt in favor of a Socratic dialogue that stress-tests assumptions and triangulates toward truth.

This paper is part of the Spring 2026 Enterprise Technology Leadership Journal, a collection of guidance papers from IT Revolution authors and past presenters at the Enterprise Technology Leadership Summit.

Pages
23
Publication Date
May 18, 2026
Topics
AI · Software Delivery & Architecture
Formats
epub · pdf
License
Creative Commons BY-NC-SA

About the author

Jonathan Snyder

For over twenty years, Jonathan Snyder has developed and promoted a humanist approach to working with creative and business technologies. As a Senior Manager at Adobe for nearly fifteen years (2005–2019), he was responsible for globally distributed teams working across a wide range of technology services including: Release Management, Problem Management, Service Quality Improvement, as well as Lean/Agile/ DevOps training and transformation. Snyder began his technology career at the Media Center for Art History, Columbia University, developing academic technology in collaboration with the art history faculty. He is currently conducting research on large language models, working to identify the architectural constraints, epistemological frameworks, and empirical telemetry required to safely and efficiently govern autonomous AI execution in real-world environments. Snyder is a graduate of Reed College, where he obtained an interdisciplinary degree in history and philosophy.

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