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