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Task Estimation Techniques

AreteDriver By AreteDriver schedule Updated 5/29/2026

name: estimate description: Task Estimation Techniques lifecycle: experimental

/estimate - Task Estimation Techniques

Structured approach to estimating development tasks.

Usage

/estimate "add user authentication"    # Estimate a task
/estimate --breakdown                  # Detailed breakdown
/estimate --range                      # Provide ranges
/estimate --compare                    # Compare techniques

What This Skill Does

  1. Analyze Task - Understand scope, complexity
  2. Break Down - Decompose into subtasks
  3. Identify Risks - Unknowns, dependencies
  4. Apply Techniques - T-shirt, story points, hours
  5. Provide Ranges - Optimistic/realistic/pessimistic

Estimation Report Format

# Estimate: [Task Description]

## Task Analysis

### Scope
What's included in this task.

### Not Included
What's explicitly out of scope.

### Assumptions
- Assumption 1
- Assumption 2

### Dependencies
- Dependency 1
- Dependency 2

---

## Breakdown

| Subtask | Complexity | Estimate |
|---------|------------|----------|
| Design/planning | Low | S |
| Core implementation | Medium | M |
| Tests | Low | S |
| Documentation | Low | XS |
| Code review | Low | XS |
| **Total** | | **M-L** |

---

## Estimate

### T-Shirt Size
**M** (Medium)

| Size | Typical Range |
|------|---------------|
| XS | < 2 hours |
| S | 2-4 hours |
| M | 4-8 hours (1 day) |
| L | 1-3 days |
| XL | 3-5 days |
| XXL | 1-2 weeks |

### Three-Point Estimate
| Scenario | Estimate | Notes |
|----------|----------|-------|
| Optimistic | 4 hours | Everything goes smoothly |
| Realistic | 8 hours | Some minor issues |
| Pessimistic | 16 hours | Unexpected complications |

**Expected**: 8-10 hours (weighted average)

### Story Points
**5 points** (Fibonacci: 1, 2, 3, 5, 8, 13, 21)

Reference:
- 1 point = trivial change, < 1 hour
- 3 points = straightforward, half day
- 5 points = moderate complexity, 1 day
- 8 points = significant work, 2-3 days
- 13+ points = should be broken down

---

## Risk Factors

| Risk | Likelihood | Impact | Mitigation |
|------|------------|--------|------------|
| Unclear requirements | Medium | High | Clarify before starting |
| Integration issues | Low | Medium | Spike first |
| Learning curve | Low | Low | Time-box research |

### Confidence Level
**Medium** (70%)

Factors affecting confidence:
- [+] Well-understood domain
- [+] Similar work done before
- [-] External API integration
- [-] Some unknowns in requirements

---

## Recommendations

1. **Clarify before starting**: [specific questions]
2. **Spike if needed**: [area of uncertainty]
3. **Break down further**: [if XXL]
4. **Add buffer**: Include 20% for unknowns

Estimation Techniques

T-Shirt Sizing

Best for: Rough estimates, backlog grooming

Size Effort Complexity Risk
XS Trivial None None
S Small Low Low
M Medium Medium Low-Med
L Large High Medium
XL Very Large High High
XXL Epic Very High High

Story Points (Fibonacci)

Best for: Sprint planning, relative sizing

1  - Trivial (< 1 hour)
2  - Simple (1-2 hours)
3  - Straightforward (half day)
5  - Moderate (1 day)
8  - Complex (2-3 days)
13 - Very complex (1 week)
21 - Epic (break it down!)

Three-Point Estimation

Best for: Schedule planning, risk assessment

Expected = (Optimistic + 4×Realistic + Pessimistic) / 6

Example:
- Optimistic: 2 days
- Realistic: 4 days
- Pessimistic: 10 days
- Expected: (2 + 16 + 10) / 6 = 4.7 days

PERT (with standard deviation)

Expected = (O + 4M + P) / 6
Std Dev = (P - O) / 6

95% confidence = Expected ± 2×StdDev

Common Estimation Mistakes

Underestimation

  • Forgetting tests
  • Forgetting code review time
  • Forgetting documentation
  • Ignoring integration time
  • Optimism bias

Overestimation

  • Adding too much buffer
  • Accounting for same risk multiple times
  • Not recognizing reusable components

General Mistakes

  • Estimating without understanding scope
  • Not breaking down large tasks
  • Ignoring dependencies
  • Treating estimates as commitments
  • Not tracking actuals vs estimates

Estimation Checklist

Before estimating:
- [ ] Requirements are clear
- [ ] Scope is defined
- [ ] Dependencies identified
- [ ] Similar past work referenced

Include in estimate:
- [ ] Design/planning time
- [ ] Implementation
- [ ] Unit tests
- [ ] Integration tests
- [ ] Code review
- [ ] Documentation
- [ ] Bug fixes (buffer)
- [ ] Meetings/communication

After estimating:
- [ ] Confidence level stated
- [ ] Risks identified
- [ ] Assumptions documented
- [ ] Range provided (not single number)

Instructions for Claude

When /estimate is invoked:

  1. Understand the task - What's being estimated
  2. Clarify scope - What's in, what's out
  3. Break down - Decompose into subtasks
  4. Identify unknowns - Risks, dependencies
  5. Apply techniques - T-shirt, points, hours
  6. Provide range - Not a single number
  7. State confidence - How sure are we
  8. Document assumptions - What we're assuming
  9. Recommend actions - Clarify, spike, break down
Install via CLI
npx skills add https://github.com/AreteDriver/ai-skills --skill estimate
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