📈 Do schedule estimates get more or less confident over time?

There are two trajectories for schedule confidence.

A schedule feels safest when it is nailed down up front, often built around what management wants to hear. Detailed Gantt charts add to that feeling. The modeling has value, but it rarely reflects reality in a complex system. Developers shape their status reports to match the expected story, and problems stay buried to fit the narrative handed down. Near the end of the project, the unknowns finally reveal themselves and the delays arrive. The schedule ends up less certain at the "end" of the project than at the beginning.

Another approach ships the first release as soon as possible, then the next. Each release updates the end date based on what the last one taught. Confidence grows over time because the unknowns and the problems surface early.