Beware Inherited Constraints

A database cost project that started as ‘move data to cheaper storage’ ended by eliminating the biggest dependency entirely, once the team stopped treating an existing implementation’s requirements as fixed and started asking what outcome each one actually served.

August 23, 2026 · 6 min · Dan Kleiman

Make Room for Ongoing Design

A whiteboard design and the system that ships from it are never the same thing. Revisiting a project well after handoff means reconstructing what actually shipped together, not grading it against the original diagram.

July 27, 2026 · 5 min · Dan Kleiman

Start with Pieces on the Board

LLMs make it possible for one person to prototype several plausible end-to-end designs before a cross-team feasibility conversation starts, turning a blank whiteboard into a concrete comparison of trade-offs.

July 26, 2026 · 7 min · Dan Kleiman

Feasibility Is Not Estimation

Rolling up team estimates for an ambitious cross-team project hides the architectural choices behind them. Real feasibility work means simulating how the pieces fit together before anyone estimates.

July 24, 2026 · 8 min · Dan Kleiman

Inline Comments Suck for Doc Review, Part II

Leaving a comment every time something catches your eye feels like a thorough review, but it just hands the author a pile of reactions to organize. Here’s how to review like you’re helping drive a decision, not narrating your read.

July 22, 2026 · 6 min · Dan Kleiman

Inline Comments Suck for Doc Review, Part I

Comment threads on a design doc create a false sense of progress. Real design review means treating comments as signals to synthesize into decisions, not a checklist to clear one thread at a time.

July 21, 2026 · 7 min · Dan Kleiman

When the Typewriter Was New: Lessons for the AI Wave

Software engineers are told to automate or be automated. But 150 years ago, the typewriter promised the same thing — and real adoption was gradual.

April 11, 2026 · 6 min · Dan Kleiman