Project Estimator
FlaggedBreaks down projects into tasks, estimates effort with confidence intervals, identifies dependencies and risks, and produces planning spreadsheets.
$ Copy the SKILL.md file to your project's .claude/skills/ directory About This Skill
Project Estimator applies structured estimation techniques to combat the planning fallacy — the universal human tendency to underestimate how long things take. It produces estimates with honest uncertainty ranges, not false precision.
Estimation Methodology
Three-Point Estimation (PERT) For each task, generates three scenarios: - **Optimistic (O)** — everything goes right, no blockers - **Most Likely (M)** — realistic with typical interruptions - **Pessimistic (P)** — significant unknowns or complications
Weighted average: `(O + 4M + P) / 6` with standard deviation `(P - O) / 6`.
Work Breakdown Structure Decomposes the project top-down: - Epic → Feature → Story → Task - Each leaf-level task estimated independently - No single task estimated over 3 days (decompose further if needed)
Confidence Bands Aggregates task estimates into project-level confidence bands: - P50 (50% confidence deadline) - P80 (80% confidence deadline) - P95 (95% confidence deadline)
Delivered with the message: "We're 80% confident this will be done by [date]."
Risk Register
- Identifies risks alongside estimates:
- Technical risks (unfamiliar technology, external API dependencies)
- Resource risks (key person dependency, part-time availability)
- Scope risks (ambiguous requirements, stakeholder alignment gaps)
Each risk scored by probability × impact with mitigation suggestions.
Output Formats
- CSV for import into Jira, Linear, or Notion
- Markdown task list with time estimates
- Gantt chart description for visualization tools
Use Cases
- Estimating development sprints and releases for engineering teams
- Creating project proposals with realistic timelines for clients
- Breaking down product features into sized user stories
- Building resource allocation plans for multi-team projects
Pros & Cons
Pros
- +Three-point PERT estimation provides honest uncertainty ranges
- +P50/P80/P95 confidence bands for stakeholder communication
- +Risk register generated alongside estimates
- +CSV output importable to Jira, Linear, and Notion
Cons
- -Estimate quality depends on the detail of the project description provided
- -Does not integrate with actual velocity data from your team's sprint history
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