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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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