Maintainable

Sep 01, 2026 — Customers don’t ask you to pay down technical debt. They notice when the product is slow, unreliable, or keeps breaking in the same damn way. Kristin Isaac joins Robby to explore how engineers can translate invisible maintenance work into customer and...

Aug 18, 2026 — David Hayes believes maintainable software starts with a simple idea: fitness for purpose.

Aug 04, 2026 — Software powered by AI can change its behavior without a deployment, leaving teams to maintain code, data, prompts, models, and the uncertainty between them. Diana Pfeil joins Robby to explain how evals, production monitoring, and a preference for...

Jun 16, 2026 — Chris Coyier, co-founder of CodePen, joins Robby to reflect on what it takes to maintain software over the long haul. Drawing from CodePen’s 15-plus-year journey, Chris shares lessons about balancing stability with innovation, navigating technical...

May 05, 2026 — Sally Lait joins Robby to explore why confidence might be the most important signal of software maintainability. They dig into the cultural dynamics behind legacy systems, why technical debt becomes a people problem, and how teams can move forward...