Assess Estimation Readiness
EST-1 Order: #1 Elaboration
Updated 5 months ago
Guidance
Purpose
Determine what inputs are available, choose the appropriate estimation level (Level 1 SWAG vs. Level 2 Detailed), and produce an Estimation Strategy document that governs the rest of the workflow.
Prerequisites
- Project idea, vision document, or feature files exist
- Stakeholder available to answer risk-profile questions
Steps
Step 1: Inventory Available Inputs
Check which artifacts exist and record their status:
| Artifact | Location | Status |
|---|---|---|
| BDD Feature Files | docs/features/ |
exists / partial / missing |
| Software Architecture Overview | docs/architecture/SAO.md |
exists / missing |
| User Journey | docs/features/user_journey.md |
exists / missing |
| Previous Sprint Actuals | Reference Table | exists / missing |
| Reference Story Calibration | Reference Table | calibrated / uncalibrated |
Step 1.5: Check Project Bootstrap and Process Setup Status
Verify whether the project has been bootstrapped (BSP workflow) and whether the AI IDE has been configured (DSP workflow):
BSP check — is the project runnable?
| Check | What to Look For | Status |
|---|---|---|
| Git repository | .git/ directory exists |
exists / missing |
| Project entry point | manage.py, package.json, Cargo.toml, etc. |
exists / missing |
| Dependency file | requirements.txt, package.json, Cargo.toml |
exists / missing |
| Makefile | Makefile with provision, run, test targets |
exists / missing |
| Source directories | Application code directories per SAO.md structure | exists / missing |
If 3+ BSP checks are missing → project is not bootstrapped.
Action for non-bootstrapped projects:
Ask user: "Project is not bootstrapped. Include BSP + DSP setup in the estimate as Sprint 0 overhead?"
- Yes → Add Sprint 0 overhead to estimation:
- Create a "Sprint 0: Project Setup" line item in the WBS and Client Quote
- BSP overhead: 10 FP (8 activities — see REFERENCE_TABLE §7)
- DSP overhead: 5 FP (6 activities — see REFERENCE_TABLE §7)
- Total Sprint 0: ~15 FP (before Stack × Org adjustment)
-
Record in ESTIMATION_STRATEGY.md: "Sprint 0 bootstrap overhead included: 15 FP"
-
No → Redirect to BSP workflow:
- Stop EST workflow
- Direct user: "Please run BSP (Bootstrap Project) workflow first, then return to EST"
- Record in ESTIMATION_STRATEGY.md: "Bootstrap deferred — not included in estimates"
DSP check — is the AI IDE configured?
| Check | What to Look For | Status |
|---|---|---|
| CLAUDE.md | CLAUDE.md exists in project root |
exists / missing |
| Copilot instructions | .github/copilot-instructions.md exists |
exists / missing |
| Windsurf/Cursor rules | .windsurf/rules/ or .cursor/rules/ exists |
exists / missing |
If DSP artifacts are missing and BSP is being quoted: include DSP FP in the Sprint 0 overhead (already in the 15 FP above).
If BSP is done but DSP is missing: add DSP as a 5 FP line item in Sprint 1.
If project is fully bootstrapped and DSP is done → proceed to Step 2 (no action needed).
Step 2: Run Boehm & Turner 5-Factor Risk Assessment
Rate each factor on the appropriate scale. Circle the home ground that applies.
| Factor | Agile Home Ground | Plan-Driven Home Ground | This Project |
|---|---|---|---|
| Team Size | ≤10 | ≥20 | ___ |
| Criticality | Low (comfort) | High (money/life) | ___ |
| Requirements Dynamism | High change rate | Stable | ___ |
| Culture | Chaos-tolerant | Order-preferring | ___ |
| Personnel | All senior/CRACK | Mixed skill levels | ___ |
Identify dominant risk type:
- A-risks dominate (too agile) → lean toward more process/Level 2
- P-risks dominate (too plan-driven) → stay Level 1, iterate fast
- Mixed → Level 1 now, schedule Level 2 after Sprint 1
Step 3: Select Estimation Level
Level 1 SWAG — use when:
- Feature files exist but SAO.MD is absent
- Project is in early discovery
- Team size ≤ 5, low criticality
- First sprint (always start here)
Level 1 + Level 2 Detailed — use when:
- docs/architecture/SAO.md exists and is current
- Requirements stability ≥ 80% (McConnell prerequisite)
- Team size > 10 or criticality is high
- Stakeholder requires commitment-quality estimates
Both levels produce the same Excel output; Level 2 simply populates additional tabs (WBS Features + Detailed Estimates) and enables the Client Quote tab (AFP pricing).
Step 4: Document Estimation Strategy
Create or update docs/plans/ESTIMATION_STRATEGY.md with:
- Estimation level chosen and rationale
- Risk profile summary (5-factor ratings)
- Sprint 0 overhead included? (BSP/DSP FP count)
- Gate condition for upgrading to Level 2 (e.g., "after SAO.MD is complete")
- Sprint refinement cadence (default: every sprint close)
- Reference Table location
Step 5: Open Excel Estimation Template
Open docs/plans/ESTIMATION_TEMPLATE.xlsx. Verify all tabs are present:
0. Client Quote
1. Setup
2. Scenario List
3. ECF
4. TCF
5. Rough Estimates
6. Monte Carlo
7. WBS Features
8. Detailed Estimates
If file does not exist, copy from forge/templates/ESTIMATION_TEMPLATE.xlsx.
Rules to Follow
I. Prerequisites Before Estimating
Never produce token or duration estimates without first completing Steps 1–3. An estimate produced without a risk assessment is a guess, not engineering.
II. Level Decision is Reversible
Choosing Level 1 does not prevent upgrading to Level 2 later. Record the upgrade gate condition explicitly so it is not forgotten.
III. McConnell Prerequisite Checklist
Before Level 2: confirm problem definition is documented, requirements are ≥ 80% complete, and architecture is sketched. Without these, Level 2 adds false precision, not real accuracy.
IV. Sprint 0 Is Always Quoted Separately
BSP and DSP overhead FP must appear as a separate line item on the Client Quote — never blended into feature delivery FPs. The client must see the setup cost explicitly.
Success Criteria
- Input inventory complete
- Bootstrap and DSP status checked; Sprint 0 overhead FP recorded if applicable
- 5-factor risk assessment documented
- Estimation level selected with rationale
- ESTIMATION_STRATEGY.md created/updated
- Excel template open and verified
Details
- Order:
- #1
- Phase:
- Created:
- Apr 12, 2026
- Last Updated:
- Apr 14, 2026
Workflow
Estimate the Project
Two-level estimation workflow for AI-assisted software development. Level 1 produces T-shirt-sized SWAG from BDD scenarios. Level 2 (Function Point decomposition) …
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