C-Level Advisory OrganizationHealthDiagnostics

Org Health Diagnostic

Cross-functional organizational health check scoring 8 dimensions.

$skillfish add ~skills/org-health-diagnostic

Real Conversations

See how the Org Health Diagnostic skill responds to actual requests. These are representative examples of what your AI agent will produce.

You

We're about to go from 28 to 50 people in the next 9 months. Series A just closed. Before we hire aggressively, I want to know if we have underlying org health issues that will just get amplified at scale. How do I diagnose this?

Agent

Smart move — org health problems at 28 people become org disasters at 50. Here's a diagnostic across 8 dimensions.

8-Dimension Org Health Scorecard:

Dimension Diagnostic Question Red Flag Signal
Psychological Safety Do people raise problems in meetings or after? Problems surface in Slack DMs, not meetings
Decision Velocity How long does it take to decide and act on a proposal? Reversible decisions take >1 week
Information Flow Do ICs know why priorities changed? "No one tells us anything" is common
Manager Quality Are team leads coaches or traffic directors? High attrition on specific teams
Cross-functional Trust Do teams help each other or protect turf? Finger-pointing in postmortems
Clarity of Direction Can every IC name the top 3 company priorities? Random sample test: ask 5 ICs right now
Recognition/Fairness Are promotions perceived as merit-based? High performers leave after being passed over
Execution Rhythm Do quarters end with delivered commitments? >40% of OKRs consistently miss

Diagnostic Method (2 weeks):

  1. Anonymous pulse survey (10 questions, one per dimension + open text)
  2. 1:1 interviews with 8 people: 2 high performers, 2 mid-level, 2 new hires, 2 people you're uncertain about
  3. Attrition analysis: who left in the last 12 months and why?

Amplification risk at 50 people: Whatever score is lowest in your diagnostic today will be 2x more painful at 50. A team with weak manager quality at 28 will have a manager quality crisis at 50 — you won't have bandwidth to compensate.

Do you have any existing survey data or are you starting from scratch?

Get Started

How to install and use this skill in your preferred environment.

Skills are designed for AI coding agents (Claude Code, Cursor, Windsurf) and IDE-based workflows where the agent can read files, run scripts, and act on your codebase. Web-based AI can use the knowledge and frameworks, but won't have tool access.

Models & Context

Which AI models and context windows work best with this skill.

Recommended Models

Best
Claude Opus 4 Claude Sonnet 4 GPT-4.1 Gemini 2.5 Pro Grok 3 Kimi K2
Good
Claude Haiku 4.5 GPT-4.1 mini Gemini 2.5 Flash Grok 3 mini

Larger models produce more detailed, production-ready outputs.

Context Window

This skill's SKILL.md is typically 3–10 KB — fits in any modern context window.

8K Skill only
32K+ Skill + conversation
100K+ Skill + references + codebase

All current frontier models (Claude, GPT, Gemini) support 100K+ context. Use the full window for complex multi-service work.

Pro tips for best results

1

Be specific

Include numbers — users, budget, RPS — so the skill can size the architecture.

2

Share constraints

Compliance needs, team size, and existing stack all improve the output.

3

Iterate

Start with a high-level design, then ask follow-ups for IaC, cost analysis, or security review.

4

Combine skills

Pair with companion skills below for end-to-end coverage.

Ready to try Org Health Diagnostic?

Install the skill and start getting expert-level guidance in your workflow — any agent, any IDE.

$skillfish add ~skills/org-health-diagnostic
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