Outlining Proposals

Outlining Proposals

Turn the compliance matrix into a proposal structure: a Section L-compliant annotated outline and a storyboard for each section. This is the planning step that proposal teams most often skip and most often regret. Drafting straight from a requirements list produces a compliant document with no strategy. Outlining and storyboarding first means every section has a defined job — its requirements, its evaluation factors, its theme, its proof — before anyone writes a paragraph.

When to use this skill

Use this skill after shredding-solicitations has produced the compliance matrix and before drafting-proposal-sections. The outline is what the Pink Team reviews, so it must exist before any serious drafting.

It does not write narrative — that is drafting-proposal-sections. It produces the plan that drafting executes.

Inputs

Required: 10-compliance-matrix.md — the outline is built from it.

Preferred upstream artifacts:

• 05-win-strategy.md: the win themes and proof points to assign to sections.
• The solicitation Section L — the authoritative structure and page limits.

Without the win strategy, the outline is structurally complete but cannot assign themes; flag every section's theme slot as "to be assigned" and recommend running developing-win-strategy.

Read ../../shared/glossary.md and ../../shared/pursuit-workspace.md if not already read this session.

Intake

Ask these as a numbered list. Skip what the matrix and solicitation answer.

1. Volumes and structure. What volumes does Section L require, and does it

prescribe the section order and headings within each? (The outline must match Section L exactly; Section L wins over any default structure.)

1. Page limits. What is the page limit per volume, and what counts against

it? This drives the page budget.

1. Win themes. Is 05-win-strategy.md available with themes and proof

points to assign?

1. Authors. Are section authors known, so the outline can assign ownership?
2. Graphics intent. Does the team have an action-caption and graphics

convention, or should the outline simply propose graphic concepts per section?

Workflow

Proposal Outline and Storyboards:
- [ ] Step 1: Read the matrix and win strategy; complete intake
- [ ] Step 2: Build the section structure from Section L
- [ ] Step 3: Map every compliance-matrix requirement to a section
- [ ] Step 4: Annotate each section (factors, themes, proof, graphics)
- [ ] Step 5: Build the page budget
- [ ] Step 6: Write a storyboard for each section
- [ ] Step 7: Write the outline (11-proposal-outline.md) and validate

Step 1: Read and intake. Read the compliance matrix and win strategy.

Step 2: Section structure. Build the outline's heading structure directly from Section L, using references/annotated-outline-method.md. The structure mirrors Section L's prescribed volumes, order, and headings. Where Section L is silent on sub-structure, structure to Section M so the evaluator finds each factor where they expect it.

Step 3: Map requirements to sections. Assign every requirement in the compliance matrix to exactly one home section. Update the matrix's "Volume & section" column as you go. Two checks: every requirement has a home (no orphans), and no section is missing requirements it logically owns. An unassigned mandatory requirement is a planned deficiency.

Step 4: Annotate. For each section, record: the requirement IDs it covers, the Section M factor(s) it is scored under, the win theme it threads, the proof points it must land, the graphic concept(s), the page allocation, and the author. This annotation is what makes the outline a plan rather than a table of contents.

Step 5: Page budget. Allocate the volume's page limit across sections. Weight pages toward the highest-value Section M factors, not evenly. A section worth little in Section M does not earn many pages. The budget must sum to at or under the limit.

Step 6: Storyboards. Write a storyboard for each substantive section using references/storyboarding.md: the section's theme statement, the customer issue it answers, the proof points, the graphic concept, the requirements covered, and the intended evaluator takeaway. The storyboard is the writer's instruction sheet and the Pink Team's review object.

Step 7: Write and validate. Write 11-proposal-outline.md using templates/proposal-outline.md. Run its validation checklist: the structure matches Section L, every matrix requirement is mapped to exactly one section, every section is annotated, the page budget sums within the limit, and every substantive section has a storyboard.

Output

One artifact: 11-proposal-outline.md — the annotated outline plus the storyboards. Also updates the "Volume & section" column of 10-compliance-matrix.md.

Present the user with: the volume/section structure, the page budget, any requirements that were hard to place, and any sections with weak theme or proof coverage.

References

• references/annotated-outline-method.md: building the structure from Section L, mapping requirements, annotating sections, and page budgeting.
• references/storyboarding.md: the storyboard sheet, writing a theme statement, graphic concepts, and the storyboard review.
• templates/proposal-outline.md: the annotated outline and storyboard templates and the validation checklist.

Guardrails

• Section L is the structure. The outline mirrors Section L's prescribed

organization exactly. An evaluator following Section L must find every section where they expect it. Do not impose a "better" structure.

• No orphan requirements. Every compliance-matrix requirement maps to exactly

one section. Zero is a planned miss; two is duplicated effort and risk.

• Pages follow value. Budget pages by Section M importance, not evenly.
• Plan before prose. This skill produces a plan. If asked to "just write the

proposal," produce the outline and storyboards first and say why.

Source & license

This open-source skill is cataloged on AgentStack and links to its original source — we do not rehost the code.

• Author: danielkinneyspears
• Source: danielkinneyspears/federal-proposal-skills
• License: Apache-2.0

Install and usage instructions live in the source repository linked above.