org-planning

Org Planning helps plan organizational structure, headcount, and team design. It is triggered by phrases such as "org planning," "headcount plan," "team structure," "reorg," or "who should we hire next," and more generally when someone is thinking about team size, reporting structure, or organizational design. The skill frames the problem across four planning dimensions: headcount (how many people are needed, in what roles, and by when), structure (reporting lines, span of control, and team boundaries), sequencing (which hires are most critical and in what order), and budget (headcount cost modeling and trade-offs).

To ground recommendations, the skill provides a set of healthy org benchmarks with explicit ranges and warning signs. A span of control of five to eight direct reports is considered healthy, while fewer than three or more than twelve is a warning sign. It suggests four to six management layers for an organization of 500 people, cautioning that too many layers slow decisions. An IC-to-manager ratio between 6:1 and 10:1 is healthy, with below 4:1 indicating a top-heavy structure. Team size of five to nine people is the target, noting that fewer than four can feel lonely and more than twelve is hard to manage.

As output, the skill produces text-based org charts, headcount plans with cost modeling, and sequenced hiring roadmaps. It also flags structural issues, such as single points of failure or excessive management overhead, so leaders can address risks in the proposed structure. The documentation is concise and high level, positioning the skill as a planning aid for decisions about how large a team should be, how it should report, and which roles to prioritize next.