Org Planning
Model headcount, reporting structure, and hire sequencing when a solo builder is scaling into a small team or planning a reorg.
Overview
Org Planning is an agent skill most often used in Build (also Grow, Operate) that helps solo builders plan headcount, reporting structure, and sequenced hiring with benchmark-backed org-health checks.
Install
npx skills add https://github.com/anthropics/knowledge-work-plugins --skill org-planningWhat is this skill?
- Dimensions: headcount by role/date, structure, hire sequencing, and budget trade-offs
- Healthy-org benchmark table (span 5–8, layers, IC:manager 6:1–10:1, team size 5–9)
- Outputs text org charts, cost-modeled headcount plans, and sequenced hiring roadmaps
- Flags single points of failure and excessive management overhead
- 4 planning dimensions
- 4-row healthy org benchmark table
Adoption & trust: 1.6k installs on skills.sh; 19.6k GitHub stars; 3/3 security scanners passed (skills.sh audits).
What problem does it solve?
You know you need to hire or reorganize but lack a structured headcount plan, sane spans of control, and a sequenced roadmap tied to budget.
Who is it for?
Founders scaling past solo delivery who need lightweight org design, hire ordering, and benchmark sanity checks without an HR platform.
Skip if: Teams that only need sprint backlog sizing, legal employment compliance, or automated headcount sync from an HRIS—use sprint-planning or your HR tools instead.
When should I use this skill?
User says org planning, headcount plan, team structure, reorg, who should we hire next, or is thinking about team size, reporting structure, or organizational design.
What do I get? / Deliverables
You get text org charts, a cost-aware headcount plan, a sequenced hiring roadmap, and flagged structural risks before you commit to offers or reporting changes.
- Text-based org chart
- Headcount plan with cost modeling
- Sequenced hiring roadmap
Recommended Skills
Journey fit
Spans multiple journey phases - primary shelf plus alternate fits below.
Canonical shelf is Build → PM because org design sits next to roadmap and capacity planning before you commit to hires and sprint load. Team structure and headcount plans are product-organization decisions, not infra or frontend implementation work.
Where it fits
Map first three engineering hires and reporting lines before committing to a fundraise or launch deadline.
Sanity-check whether the MVP can stay founder-only or needs a contractor role in the plan.
Sequence customer-success and ops hires as ticket volume grows without duplicating management layers.
Flatten excessive management layers after benchmarks show IC-to-manager ratio is top-heavy.
How it compares
Planning artifact for team design and headcount—not a sprint capacity planner or a people-analytics dashboard.
Common Questions / FAQ
Who is org-planning for?
Solo and indie builders (and very small teams) who are deciding how big the team should be, how it should be structured, and which hires come first as the product scales.
When should I use org-planning?
During Build when staffing the roadmap; in Grow when adding roles for distribution or support; in Operate when fixing top-heavy layers or single points of failure—trigger phrases include org planning, headcount plan, team structure, reorg, and who should we hire next.
Is org-planning safe to install?
It is procedural planning guidance in SKILL.md with no built-in shell or network requirements; review the Security Audits panel on this Prism page before installing any skill from the repo.
SKILL.md
READMESKILL.md - Org Planning
# Org Planning Help plan organizational structure, headcount, and team design. ## Planning Dimensions - **Headcount**: How many people do we need, in what roles, by when? - **Structure**: Reporting lines, span of control, team boundaries - **Sequencing**: Which hires are most critical? What's the right order? - **Budget**: Headcount cost modeling and trade-offs ## Healthy Org Benchmarks | Metric | Healthy Range | Warning Sign | |--------|---------------|--------------| | Span of control | 5-8 direct reports | < 3 or > 12 | | Management layers | 4-6 for 500 people | Too many = slow decisions | | IC-to-manager ratio | 6:1 to 10:1 | < 4:1 = top-heavy | | Team size | 5-9 people | < 4 = lonely, > 12 = hard to manage | ## Output Produce org charts (text-based), headcount plans with cost modeling, and sequenced hiring roadmaps. Flag structural issues like single points of failure or excessive management overhead.