Strategy-to-execution gap identifier

Purpose

Diagnose exactly where a nonprofit's stated strategy is disconnected from how the organization is actually structured, staffed, funded, and run — producing a ranked list of execution gaps with specific closure moves. Solves the common problem of a strategic plan that reads well on paper but never moves the operating reality behind it.

When to Use

Invoke this skill when the user asks to:

• Understand why a strategic plan isn't producing results despite board approval
• Diagnose the disconnect between organizational priorities and daily operations
• Prepare for a board or leadership retreat on execution and accountability
• Assess whether current staffing and budget actually support the stated strategy
• Identify what's blocking a specific strategic goal from advancing
• Build the case for reallocating people, money, or process ownership

Inputs Required

Before starting, collect:

• Stated strategic priorities: The 3–6 priorities from the current strategic plan, ideally with any stated goals or targets
• Organizational structure: How teams/departments are organized and who reports to whom
• Staffing snapshot: Roles, headcount, and rough allocation of who works on what
• Budget allocation: How the operating budget is split across programs, functions, or priorities (percentages or dollar ranges are fine)
• Key processes: How major decisions get made, work gets approved, and priorities get resourced
• Known friction points: Where leadership already senses things stall (optional but valuable)
• Time horizon: The plan period (e.g., 3-year plan, year 2)

If budget percentages or process detail are missing, work from the structure and staffing provided and flag each assumption explicitly rather than inventing figures.

Instructions

Step 1: Restate the Strategic Priorities as Execution Demands

For each stated priority, translate it into what the organization would actually need to be doing operationally to deliver it. A priority like "deepen community partnerships" becomes concrete demands: dedicated relationship-owner capacity, a partnership pipeline process, and budget for convening. This creates the yardstick every operating-model element is measured against.

Step 2: Map the Operating Model Against Each Priority

Build a priority-by-element assessment across four operating dimensions. For each priority, evaluate:

• Structure: Does an owner/team clearly hold this priority? Is accountability fragmented or orphaned?
• Staffing: Is there real capacity (FTE) assigned, or is it "everyone's job" (which means no one's)?
• Budget: Does the dollar allocation match the priority's stated importance, or is spending concentrated elsewhere?
• Process: Do decision rights, approval flows, and cadence support the work — or throttle it?

Flag each cell as Aligned, Partial, or Gap.

Step 3: Diagnose Each Gap by Type

For every Gap or Partial identified, classify the failure mode:

• Ownership gap: No single accountable owner; the priority has no home
• Capacity gap: Named owner exists but has no protected time or is over-allocated
• Resource gap: Budget doesn't follow the stated priority — money is going to legacy activities
• Process gap: Work gets stuck in approval bottlenecks, unclear decision rights, or missing cadence
• Alignment gap: Structure, staff, and budget contradict the stated priority (the org is optimized for a different strategy than the one it wrote down)

Name the specific evidence from the inputs that supports each classification.

Step 4: Score and Rank Gaps by Strategic Impact

Rank every identified gap using two axes:

• Strategic weight: How central this priority is to the mission and plan (High / Medium / Low)
• Blockage severity: How completely the gap stops execution (Fully blocked / Constrained / Slowed)

Prioritize gaps that combine High strategic weight with Fully blocked / Constrained severity. Produce a ranked list — most strategically damaging gap first.

Step 5: Prescribe a Closure Move for Each Top Gap

For the top 5–7 ranked gaps, specify:

1. The gap in one sentence
2. Closure move: The specific structural, staffing, budget, or process change required
3. Owner: Who should hold this fix (role, not a placeholder name)
4. Effort/disruption level: Low / Medium / High — with a one-line reason
5. Leading indicator: The earliest observable sign the gap is closing

Step 6: Surface the Root Pattern

Identify whether the gaps share a common cause — most stalled strategies fail from one or two systemic patterns (e.g., budget frozen in legacy programs, or a flat structure with no priority owners) rather than many independent problems. State the single highest-leverage move that addresses the most gaps at once.

Output Format

• Structure: Priority-by-element alignment table, followed by ranked gap analysis and closure recommendations
• Length: 900–1,300 words
• Format: Structured document with one table (priorities × 4 operating dimensions) plus numbered ranked gaps and closure specs
• Sections: Priorities as execution demands → Operating model alignment table → Ranked gap analysis → Closure moves for top gaps → Root pattern and highest-leverage move
• Tone: Executive strategy advisor — direct, evidence-anchored, unsentimental about where the organization is misaligned; respectful of mission but honest about resource reality

Quality Checklist

Before delivering output, verify:

• [ ] Every stated priority is assessed against all four operating dimensions (structure, staffing, budget, process)
• [ ] Each gap is classified by a specific failure type — not just labeled "misaligned"
• [ ] Gaps are ranked by strategic impact, with High-weight/Fully-blocked gaps surfaced first — not listed in input order
• [ ] Each top gap has a closure move naming a specific change, a role-based owner, and a leading indicator
• [ ] Every gap cites concrete evidence drawn from the inputs, and all assumptions are flagged where data was missing
• [ ] A single highest-leverage root move is named, not just a list of independent fixes

Notes

• The most common finding is a budget frozen in legacy programs while the plan names new priorities — money reveals the real strategy more honestly than the plan document does.
• "It's everyone's job" is almost always an ownership gap in disguise; treat shared accountability with no protected capacity as a Gap, not Partial.
• When structure, staffing, and budget all point one direction but the written strategy points another, the organization is executing an unstated strategy — name that directly, as it's usually the retreat conversation leadership most needs to have.

How to use this skill

This file is a Claude Code skill in Anthropic's standard format — markdown with YAML frontmatter at the top.

Installing in Claude Code:

• ~/.claude/skills/<folder-name>/SKILL.md — auto-loads in every session anywhere on your machine (recommended for skills you'll use across multiple projects)
• <your-project>/.claude/skills/<folder-name>/SKILL.md — auto-loads only when working in that project (recommended for project-specific skills)

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Using in Claude.ai, ChatGPT, Gemini, or other AI tools:

1. Drag this file into a new chat, or copy and paste its contents
2. Send your task or request as your next message — the AI will apply the skill where it fits

For Claude Code skill details: https://docs.anthropic.com/en/docs/claude-code/skills