Progressive Estimation
Estimate AI-assisted and hybrid human+agent development work using research-backed formulas with PERT statistics, confidence bands, and calibration feedback loops.
Overview
Progressive Estimation adapts to your team's working mode — human-only, hybrid, or agent-first — applying the right velocity model and multipliers for each. It produces statistical estimates rather than gut feelings.
When to Use This Skill
- Estimating development tasks where AI agents handle part of the work
- Sprint planning with hybrid human+agent teams
- Batch sizing a backlog (handles 5 or 500 issues)
- Staffing and capacity planning with agent multipliers
- Release date forecasting with confidence intervals
How It Works
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Mode Detection — Determines if the team works human-only, hybrid, or agent-first
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Task Classification — Categorizes by size (XS–XL), complexity, and risk
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Formula Application — Applies research-backed multipliers grounded in empirical studies
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PERT Calculation — Produces expected values using three-point estimation
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Confidence Bands — Generates P50, P75, P90 intervals
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Output Formatting — Formats for Linear, JIRA, ClickUp, GitHub Issues, Monday, or GitLab
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Calibration — Feeds back actuals to improve future estimates
Examples
Single task:
"Estimate building a REST API with authentication using Claude Code"
Batch mode:
"Estimate these 12 JIRA tickets for our next sprint"
With context:
"We have 3 developers using AI agents for ~60% of implementation. Estimate this feature."
Best Practices
- Start with a single task to calibrate before moving to batch mode
- Feed back actual completion times to improve the calibration system
- Use "instant mode" for quick T-shirt sizing without full PERT analysis
- Be explicit about team composition and agent usage percentage
Common Pitfalls
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Problem: Overconfident estimates
Solution: Use P75 or P90 for commitments, not P50
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Problem: Missing context
Solution: The skill asks clarifying questions — provide team size and agent usage
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Problem: Stale calibration
Solution: Re-calibrate when team composition or tooling changes significantly
Related Skills
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@sprint-planning - Sprint planning and backlog management
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@project-management - General project management workflows
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@capacity-planning - Team velocity and capacity planning
Additional Resources
