Purpose
Diagnose whether a nonprofit's current executive team can actually deliver its strategic priorities — identifying capability gaps, overlapping mandates, decision-rights confusion, and single points of failure — and deliver a gap map with a ranked set of structural, hiring, and development actions. Replaces gut-feel "we need another senior person" reasoning with a defensible workforce plan a board can approve.
When to Use
Invoke this skill when the user asks to:
- Assess whether the current leadership team can execute the strategic plan
- Decide whether to hire, restructure, or develop before adding a new executive role
- Prepare for a CEO or senior leader departure and surface succession risk
- Diagnose why senior decisions stall, get re-litigated, or fall between roles
- Review executive team structure ahead of a strategic plan refresh or merger
- Build the leadership-capacity case for a board or funder
Inputs Required
Before starting, collect:
- Current executive roster: Each member's title, function, tenure, and 2–4 sentence skill/strength profile
- Strategic priorities: The 3–6 priorities or goals from the current strategic plan
- Organization profile: Mission, budget size, staff headcount, lifecycle stage (startup / growth / mature / turnaround)
- Known pain points: Where decisions stall, conflict, or things fall through the cracks
- Succession concerns: Any roles known to be flight risks, retirements, or hard-to-fill
- Constraints: Budget ceiling for new roles, hiring freeze, board appetite for restructuring
- Decision-making norms: How major decisions currently get made (CEO-driven, consensus, committee)
If strategic priorities are vague, ask the user to state them as outcomes ("grow earned revenue to 30% of budget") rather than activities before proceeding.
Instructions
Step 1: Translate Strategic Priorities Into Required Capabilities
For each strategic priority, name the 2–4 leadership capabilities required to deliver it (e.g., "scale earned revenue" → enterprise/business model design, sales leadership, financial modeling). Produce a Capability Requirements list — the full set of capabilities the team must collectively hold to execute the plan. This is the demand side of the analysis.
Step 2: Map Current Coverage (Supply Side)
For each member, map their actual demonstrated strengths to the Capability Requirements list. Mark each required capability as:
- Covered (strong): A leader clearly owns and excels at it
- Covered (thin): Someone holds it but is stretched, junior in it, or part-time on it
- Gap: No one credibly holds it
- Redundant: Two or more leaders hold the same capability with no clear division
Be honest about thin coverage — "the CEO does it on the side" is thin coverage, not strong coverage.
Step 3: Apply Decision-Rights Clarity (RACI / DACI)
For the 5–8 most consequential recurring decisions tied to strategic priorities (e.g., major hires, budget reallocation, program sunset, partnership approval), assess role clarity:
- RACI: Who is Responsible, Accountable, Consulted, Informed
- DACI (where useful): Driver, Approver, Contributors, Informed — better for fast-moving decisions Flag any decision with two Accountable parties (the most common cause of stalled decisions), no clear Accountable party, or where the CEO is Accountable for everything (a scaling bottleneck). Tie each flag back to a pain point if one was reported.
Step 4: Assess Succession & Concentration Risk
For each executive, rate:
- Succession risk: Low / Medium / High — based on flight risk, retirement horizon, and how hard the role is to backfill
- Knowledge concentration: Is critical institutional knowledge or relationships (major donors, key funders, board) held by one person with no backup? Apply the single-point-of-failure test: if this person left in 30 days, what breaks and how fast? Identify the top 1–3 concentration risks.
Step 5: Build the Gap Map
Synthesize Steps 1–4 into a single Gap Map table: rows = required capabilities and critical decisions; columns = current owner, coverage status, decision-rights issue, succession/concentration risk. This is the centerpiece deliverable — it must let a board chair see the whole leadership picture on one page.
Step 6: Rank Recommended Actions
Produce 6–10 actions, each tagged by lever type and ranked by strategic impact:
- Develop: Grow an existing leader into a thin-coverage capability (fastest, cheapest)
- Restructure: Reassign mandates or clarify decision rights (no new headcount)
- Hire: Add a role — only where develop/restructure can't close the gap, with a one-line role rationale and seniority level
- De-risk: Succession plan, cross-train, or document for a concentration risk For each action: the gap it closes, the lever, expected impact, and rough sequence (now / next 6 months / next 12 months). Default to develop and restructure before recommending new hires unless budget input indicates otherwise.
Step 7: Name the Single Most Important Move
State the one action the user should take first and why. Be opinionated.
Output Format
- Structure: Capability requirements list → coverage analysis → decision-rights findings → succession risk findings → Gap Map table → ranked action plan → top recommended move
- Length: 1,000–1,400 words
- Format: Prose analysis with one central Gap Map table and a numbered ranked action list
- Sections: Capability Requirements → Current Coverage → Decision-Rights (RACI/DACI) Findings → Succession & Concentration Risk → Gap Map (table) → Recommended Actions (ranked) → Top Priority Move
- Tone: Trusted strategy advisor to a board — candid, structural, evidence-based; names hard truths without alarmism
Quality Checklist
Before delivering output, verify:
- [ ] Every strategic priority maps to named required capabilities (none left unaddressed)
- [ ] Each required capability is marked with one of the four coverage statuses
- [ ] At least 5 consequential decisions are assessed with explicit RACI/DACI ownership
- [ ] Every decision flagged for "two Accountable parties" or "no Accountable party" is called out
- [ ] The Gap Map appears as a single table covering capabilities, decisions, coverage, and risk
- [ ] Action plan favors develop/restructure over hiring unless budget input justifies new roles, and each action is sequenced
- [ ] A single top-priority move is named without hedging
Notes
- The most common finding in nonprofits is not a capability gap but a decision-rights gap — two strong leaders with overlapping mandates and no clear Accountable party. Look there before recommending a new hire.
- Thin coverage on a fundraising or revenue capability is usually the highest-risk gap for a nonprofit, because it threatens the funding of everything else.
- Resist the board's instinct to solve every gap with a new senior hire; restructuring and development close most gaps faster and within budget.
- If the org is in a turnaround or merger, weight succession and concentration risk more heavily — instability multiplies single-point-of-failure exposure.
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)
Restart Claude Code or open a new session to register.
Using in Claude.ai, ChatGPT, Gemini, or other AI tools:
- Drag this file into a new chat, or copy and paste its contents
- 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