Estimation and Timeline Management Questions

Skills and practices for producing realistic estimates and managing timelines on technical projects. This includes collaborating with engineering teams to decompose work into phases and tasks, selecting and applying estimation techniques such as bottom up and top down estimation, and using spikes or proof of concept work to reduce uncertainty. Candidates should show how they identify critical path and dependencies, account for vendor and cross team work, quantify and communicate assumptions and risks, and build appropriate buffers or contingency plans for technical unknowns, data migrations, testing cycles, and deployment activities. Also covered are approaches for communicating estimates and confidence levels to stakeholders, negotiating scope or schedule trade offs, tracking progress, reforecasting when new information emerges, and choosing mitigation strategies such as parallelization, timeboxing, or scope sequencing to protect delivery dates.