Files
claude-skills-reference/c-level-advisor/chro-advisor/references/org_design.md
Alireza Rezvani 466aa13a7b feat: C-Suite expansion — 8 new executive advisory roles (2→10) (#264)
* feat: C-Suite expansion — 8 new executive advisory roles

Add COO, CPO, CMO, CFO, CRO, CISO, CHRO advisors and Executive Mentor.
Expands C-level advisory from 2 to 10 roles with 74 total files.

Each role includes:
- SKILL.md (lean, <5KB, ~1200 tokens for context efficiency)
- Reference docs (loaded on demand, not at startup)
- Python analysis scripts (stdlib only, runnable CLI)

Executive Mentor features /em: slash commands (challenge, board-prep,
hard-call, stress-test, postmortem) with devil's advocate agent.

21 Python tools, 24 reference frameworks, 28,379 total lines.
All SKILL.md files combined: ~17K tokens (8.5% of 200K context window).

Badge: 88 → 116 skills

* feat: C-Suite orchestration layer + 18 complementary skills

ORCHESTRATION (new):
- cs-onboard: Founder interview → company-context.md
- chief-of-staff: Routing, synthesis, inter-agent orchestration
- board-meeting: 6-phase multi-agent deliberation protocol
- decision-logger: Two-layer memory (raw transcripts + approved decisions)
- agent-protocol: Inter-agent invocation with loop prevention
- context-engine: Company context loading + anonymization

CROSS-CUTTING CAPABILITIES (new):
- board-deck-builder: Board/investor update assembly
- scenario-war-room: Cascading multi-variable what-if modeling
- competitive-intel: Systematic competitor tracking + battlecards
- org-health-diagnostic: Cross-functional health scoring (8 dimensions)
- ma-playbook: M&A strategy (acquiring + being acquired)
- intl-expansion: International market entry frameworks

CULTURE & COLLABORATION (new):
- culture-architect: Values → behaviors, culture code, health assessment
- company-os: EOS/Scaling Up operating system selection + implementation
- founder-coach: Founder development, delegation, blind spots
- strategic-alignment: Strategy cascade, silo detection, alignment scoring
- change-management: ADKAR-based change rollout framework
- internal-narrative: One story across employees/investors/customers

UPGRADES TO EXISTING ROLES:
- All 10 roles get reasoning technique directives
- All 10 roles get company-context.md integration
- All 10 roles get board meeting isolation rules
- CEO gets stage-adaptive temporal horizons (seed→C)

Key design decisions:
- Two-layer memory prevents hallucinated consensus from rejected ideas
- Phase 2 isolation: agents think independently before cross-examination
- Executive Mentor (The Critic) sees all perspectives, others don't
- 25 Python tools total (stdlib only, no dependencies)

52 new files, 10 modified, 10,862 new lines.
Total C-suite ecosystem: 134 files, 39,131 lines.

* fix: connect all dots — Chief of Staff routes to all 28 skills

- Added complementary skills registry to routing-matrix.md
- Chief of Staff SKILL.md now lists all 28 skills in ecosystem
- Added integration tables to scenario-war-room and competitive-intel
- Badge: 116 → 134 skills
- README: C-Level Advisory count 10 → 28

Quality audit passed:
 All 10 roles: company-context, reasoning, isolation, invocation
 All 6 phases in board meeting
 Two-layer memory with DO_NOT_RESURFACE
 Loop prevention (no self-invoke, max depth 2, no circular)
 All /em: commands present
 All complementary skills cross-reference roles
 Chief of Staff routes to every skill in ecosystem

* refactor: CEO + CTO advisors upgraded to C-suite parity

Both roles now match the structural standard of all new roles:
- CEO: 11.7KB → 6.8KB SKILL.md (heavy content stays in references)
- CTO: 10KB → 7.2KB SKILL.md (heavy content stays in references)

Added to both:
- Integration table (who they work with and when)
- Key diagnostic questions
- Structured metrics dashboard table
- Consistent section ordering (Keywords → Quick Start → Responsibilities → Questions → Metrics → Red Flags → Integration → Reasoning → Context)

CEO additions:
- Stage-adaptive temporal horizons (seed=3m/6m/12m → B+=1y/3y/5y)
- Cross-references to culture-architect and board-deck-builder

CTO additions:
- Key Questions section (7 diagnostic questions)
- Structured metrics table (DORA + debt + team + architecture + cost)
- Cross-references to all peer roles

All 10 roles now pass structural parity:  Keywords  QuickStart  Questions  Metrics  RedFlags  Integration

* feat: add proactive triggers + output artifacts to all 10 roles

Every C-suite role now specifies:
- Proactive Triggers: 'surface these without being asked' — context-driven
  early warnings that make advisors proactive, not reactive
- Output Artifacts: concrete deliverables per request type (what you ask →
  what you get)

CEO: runway alerts, board prep triggers, strategy review nudges
CTO: deploy frequency monitoring, tech debt thresholds, bus factor flags
COO: blocker detection, scaling threshold warnings, cadence gaps
CPO: retention curve monitoring, portfolio dog detection, research gaps
CMO: CAC trend monitoring, positioning gaps, budget staleness
CFO: runway forecasting, burn multiple alerts, scenario planning gaps
CRO: NRR monitoring, pipeline coverage, pricing review triggers
CISO: audit overdue alerts, compliance gaps, vendor risk
CHRO: retention risk, comp band gaps, org scaling thresholds
Executive Mentor: board prep triggers, groupthink detection, hard call surfacing

This transforms the C-suite from reactive advisors into proactive partners.

* feat: User Communication Standard — structured output for all roles

Defines 3 output formats in agent-protocol/SKILL.md:

1. Standard Output: Bottom Line → What → Why → How to Act → Risks → Your Decision
2. Proactive Alert: What I Noticed → Why It Matters → Action → Urgency (🔴🟡)
3. Board Meeting: Decision Required → Perspectives → Agree/Disagree → Critic → Action Items

10 non-negotiable rules:
- Bottom line first, always
- Results and decisions only (no process narration)
- What + Why + How for every finding
- Actions have owners and deadlines ('we should consider' is banned)
- Decisions framed as options with trade-offs
- Founder is the highest authority — roles recommend, founder decides
- Risks are concrete (if X → Y, costs $Z)
- Max 5 bullets per section
- No jargon without explanation
- Silence over fabricated updates

All 10 roles reference this standard.
Chief of Staff enforces it as a quality gate.
Board meeting Phase 4 uses the Board Meeting Output format.

* feat: Internal Quality Loop — verification before delivery

No role presents to the founder without passing verification:

Step 1: Self-Verification (every role, every time)
  - Source attribution: where did each data point come from?
  - Assumption audit: [VERIFIED] vs [ASSUMED] tags on every finding
  - Confidence scoring: 🟢 high / 🟡 medium / 🔴 low per finding
  - Contradiction check against company-context + decision log
  - 'So what?' test: every finding needs a business consequence

Step 2: Peer Verification (cross-functional)
  - Financial claims → CFO validates math
  - Revenue projections → CRO validates pipeline backing
  - Technical feasibility → CTO validates
  - People/hiring impact → CHRO validates
  - Skip for single-domain, low-stakes questions

Step 3: Critic Pre-Screen (high-stakes only)
  - Irreversible decisions, >20% runway impact, strategy changes
  - Executive Mentor finds weakest point before founder sees it
  - Suspicious consensus triggers mandatory pre-screen

Step 4: Course Correction (after founder feedback)
  - Approve → log + assign actions
  - Modify → re-verify changed parts
  - Reject → DO_NOT_RESURFACE + learn why
  - 30/60/90 day post-decision review

Board meeting contributions now require self-verified format with
confidence tags and source attribution on every finding.

* fix: resolve PR review issues 1, 4, and minor observation

Issue 1: c-level-advisor/CLAUDE.md — completely rewritten
  - Was: 2 skills (CEO, CTO only), dated Nov 2025
  - Now: full 28-skill ecosystem map with architecture diagram,
    all roles/orchestration/cross-cutting/culture skills listed,
    design decisions, integration with other domains

Issue 4: Root CLAUDE.md — updated all stale counts
  - 87 → 134 skills across all 3 references
  - C-Level: 2 → 33 (10 roles + 5 mentor commands + 18 complementary)
  - Tool count: 160+ → 185+
  - Reference count: 200+ → 250+

Minor observation: Documented plugin.json convention
  - Explained in c-level-advisor/CLAUDE.md that only executive-mentor
    has plugin.json because only it has slash commands (/em: namespace)
  - Other skills are invoked by name through Chief of Staff or directly

Also fixed: README.md 88+ → 134 in two places (first line + skills section)

* fix: update all plugin/index registrations for 28-skill C-suite

1. c-level-advisor/.claude-plugin/plugin.json — v2.0.0
   - Was: 2 skills, generic description
   - Now: all 28 skills listed with descriptions, all 25 scripts,
     namespace 'cs', full ecosystem description

2. .codex/skills-index.json — added 18 complementary skills
   - Was: 10 roles only
   - Now: 28 total c-level entries (10 roles + 6 orchestration +
     6 cross-cutting + 6 culture)
   - Each with full description for skill discovery

3. .claude-plugin/marketplace.json — updated c-level-skills entry
   - Was: generic 2-skill description
   - Now: v2.0.0, full 28-skill ecosystem description,
     skills_count: 28, scripts_count: 25

* feat: add root SKILL.md for c-level-advisor ClawHub package

---------

Co-authored-by: Leo <leo@openclaw.ai>
2026-03-06 01:35:08 +01:00

13 KiB
Raw Blame History

Org Design Reference

Spans of control, layering decisions, reorgs, title frameworks, career ladders, and the founder→professional management transition.


Core Org Design Principles

  1. Structure follows strategy. Reorg after strategy shifts, not before.
  2. Optimize for the bottleneck. Where does work get slow? Design around that.
  3. Minimize coordination cost. Conway's Law: your org structure becomes your product architecture. Design intentionally.
  4. Bias toward flatness until it breaks. Adding layers adds cost and slows decisions.
  5. Reorgs have transition costs. Relationships reset. Count the cost before you restructure.

Spans of Control

Span of control = number of direct reports a manager has.

Benchmarks

Role Type Optimal Span Min Max
IC manager (predictable work) 710 5 12
IC manager (complex/creative work) 57 4 8
Manager of managers 46 3 7
VP / Director 47 3 8
C-Suite 59 4 10

Too narrow (< 4 ICs): Over-management, high cost per output, manager becomes a bottleneck Too wide (> 12 ICs): Under-management, degraded 1:1 quality, feedback loops collapse

Factors that allow wider spans

  • Highly autonomous, senior team (L3+ ICs)
  • Predictable, well-defined work (support, ops)
  • Strong tooling and process (reduces manager overhead)
  • Experienced manager

Factors that require narrower spans

  • High-complexity, undefined problems (research, early product)
  • Junior or newly promoted team members
  • High interdependence between reports (coordination overhead)
  • Manager is also an IC contributor (player-coach)

When to Add Management Layers

The wrong reason to add layers: "We need to give good people somewhere to grow." The right reason: "This manager has too many direct reports to do the job well."

Layer triggers by growth stage

0 → 15 people: No layers. Everyone reports to founders.

15 → 30 people: First managers emerge. Usually technical leads or function leads. Should still be player-coaches.

30 → 60 people: Second layer forms. Engineering splits into squads. Sales gets a frontline manager. Each function has a head.

60 → 150 people: Director layer becomes necessary in large functions. Engineering VP + Engineering Directors + Team Managers.

150+ people: VP layer fully staffed. Senior Director / Director split. Clear IC → M → Senior M → Director → VP paths.

The Rule of 7

When any manager has 7 or more direct reports and:

  • 1:1s are skipped regularly
  • Feedback quality drops
  • Manager can't answer "how is each person doing?" without checking notes

→ Time to split or hire a manager.

Management overhead cost

Every manager layer costs 1015% in decision speed (communication hops). Every management role without a team = pure overhead.

Litmus test for each management role:

  • Does this person have at least 4 ICs under them?
  • Would removing this role improve decision speed?
  • Is this a management job or a "we ran out of IC levels" job?

Functional vs. Product Org Structures

Functional Structure (by discipline)

CEO
├── VP Engineering
│   ├── Backend Team
│   ├── Frontend Team
│   └── DevOps
├── VP Product
│   ├── PM (Feature A)
│   └── PM (Feature B)
└── VP Design
    └── UX Designers

Best for: Early stage, < 100 people, single product Advantage: Deep expertise development, clear career paths per discipline Disadvantage: Cross-functional coordination is heavy; features require synchronization across silos

Product/Pod Structure (by product area)

CEO
├── Product Area A (autonomous team)
│   ├── EM
│   ├── PM
│   └── Designer
├── Product Area B (autonomous team)
│   ├── EM
│   ├── PM
│   └── Designer
└── Platform (shared services)
    └── Platform EM + team

Best for: Multiple products or large user segments, 50+ in product/eng Advantage: Speed and autonomy; less cross-team coordination for most features Disadvantage: Duplication risk; harder to maintain technical coherence; harder career paths

When to shift from Functional → Product org

  • You have 2+ distinct product lines that rarely share features
  • Cross-functional feature delivery takes > 3 sprints of coordination overhead
  • Teams are > 8 engineers and still waiting on shared resources

Hybrid / Matrix (avoid unless necessary)

Matrix reporting (e.g., engineer reports to EM + PM) creates accountability confusion. Avoid at < 500 people.


Title Frameworks

The Problem with Title Inflation

Early startups over-title to compete with cash. "VP of Engineering" with 2 reports. "Head of Marketing" with no team.

Consequences:

  • Can't add leadership above inflated titles without awkward conversations
  • Candidates from mature companies expect scope commensurate with titles
  • Internal equity breaks when the same title means different things

Preventing Title Inflation

Rule 1: VP titles require managing managers (not just ICs). Rule 2: Director titles require managing multiple ICs or a large function. Rule 3: No more than one "Head of X" per function. Rule 4: Document scope expectations per title before making offers.

Engineering Title Ladder (example)

Title Level Scope Reports
Software Engineer I L1 Executes defined tasks
Software Engineer II L2 Independent delivery
Senior Software Engineer L3 Leads features, mentors
Staff Software Engineer L4 Cross-team technical leadership
Principal Software Engineer L5 Company-wide technical direction
Distinguished Engineer L6 External recognition, defining practice
Engineering Manager M1 Team of 48 engineers 48 ICs
Senior Engineering Manager M2 Larger team or manager of managers 24 managers
Director of Engineering M3 Functional area Multiple managers
VP of Engineering M4 Engineering org Directors
CTO M5 Technical organization + strategy VPs

IC vs. Management track: Explicitly separate. Senior ICs should not need to move to management for career advancement. Staff/Principal/Distinguished track provides this.

Go-to-Market Title Ladder (example)

Title Level Focus
SDR / BDR S1 Outbound prospecting
Account Executive I S2 SMB closing
Account Executive II S3 Mid-market closing
Senior Account Executive S4 Enterprise closing
Principal / Strategic AE S5 Named accounts, complex deals
Sales Manager M1 68 reps
Director of Sales M2 Multiple teams or segments
VP of Sales M3 Full sales org
CRO M4 Revenue org (sales + CS + marketing)

Career Ladders

A career ladder is a documented set of expectations per level. Not aspirational — behavioral. "What does a P3 engineer do that a P2 doesn't?"

Why career ladders matter for HR

  1. Retention: Employees can see where they're going
  2. Consistency: Managers use the same criteria for promotions
  3. Compensation: Bands anchor to levels; levels require definitions
  4. Equity: Removes "who's the manager's favorite" from promotion decisions

Career Ladder Structure

For each level, define 4 dimensions:

1. Scope — How big is the problem space? Team / cross-team / org-wide / company-wide? 2. Impact — How does work connect to outcomes? (Task → Feature → Product → Business) 3. Craft — Technical/functional skill expectations 4. Influence — How does this person improve others? (Self → peers → team → org)

Example: Senior Software Engineer (L3) vs. Staff Software Engineer (L4)

Dimension L3 (Senior SWE) L4 (Staff SWE)
Scope Owns features or services Owns technical domains across teams
Impact Ships features that improve user outcomes Shapes technical direction for a product area
Craft Writes high-quality code, good design skills Sets coding standards, contributes to architecture
Influence Mentors L1L2, code reviews Mentors L3+, identifies org-wide technical gaps

How to build a career ladder from scratch

  1. Interview your best performers — "What do you do that your junior peers don't?" Collect behaviors, not aspirations.
  2. Draft 3 levels — Don't start with 6. Start with junior, mid, senior. Add staff/principal only when you have enough people to warrant it.
  3. Manager calibration — Every manager rates 5 current employees against the draft. Gaps surface immediately.
  4. Publish and iterate — Don't wait for perfection. A 70% ladder shipped is better than a 100% ladder in a drawer.

Reorg Playbook

When reorgs are necessary

  • Strategy pivot requires different team structure (e.g., single product → multi-product)
  • Acquisition or team merger
  • Function is genuinely too slow due to coordination overhead
  • Leadership departure creates structural opportunity

When reorgs are a mistake

  • "We need to shake things up" (disruption for its own sake)
  • Avoiding a specific personnel decision (use the right tool)
  • Solving a cultural problem with a structural change
  • Reacting to one team's complaint without systemic evidence

Reorg Process (48 weeks)

Week 12: Diagnose

  • Map current org: every role, reporting line, team output
  • Identify where work is slow, duplicated, or falling through cracks
  • Interview 510 people across teams: "What takes longer than it should? What decisions are hard to make?"

Week 34: Design options

  • Draft 23 structural alternatives
  • For each: estimated coordination costs, manager span impact, open roles created
  • Validate with CEO + 12 trusted operators. Don't crowdsource the design.

Week 56: Decide and prepare

  • Select option; finalize all reporting changes
  • Prepare communications for every affected person (individual conversations before all-hands)
  • Write the "why" — employees need to understand the business reason, not just the result

Week 78: Communicate and implement

  • Individual conversations with all manager+ changes (first)
  • Team-level conversations with managers (second)
  • All-hands with full context (third)
  • Updated org chart published within 24 hours of announcement

Communication sequence (non-negotiable)

  1. Affected individuals first (private, before anything else)
  2. Affected managers second (to prepare for team conversations)
  3. Full team/company third (all-hands or company note)
  4. External (clients, board) only if materially impacted

Never: Email blast first. No individual conversations. Discovered on the org chart.


Founder → Professional Management Transition

The most common scaling failure point in startups.

Stage 1: Founder-Led (030 people)

Founders make all decisions, know everyone personally, set culture through behavior. Works because trust and context are built directly.

What breaks:

  • Decisions bottleneck at founders
  • New hires don't get enough context (founders can't be everywhere)
  • Culture transmitted through osmosis, not documentation

Stage 2: First Managers (3080 people)

Founders can no longer manage all ICs. First manager layer typically = promoted high performers.

The "brilliant IC → struggling manager" trap:

  • Individual contributor skills ≠ management skills
  • Promoted ICs often continue doing IC work while ignoring management work
  • No one holds them accountable to management output (1:1 quality, team health, performance feedback)

What to do:

  • Explicit manager training before promotion (not after)
  • Management KPIs separate from IC KPIs
  • Peer community for new managers (monthly cohort session)
  • HR check-ins on manager health at 30/60/90 days

Stage 3: Professional Management (80200 people)

External hires at Director/VP level bring professional management skills but lack company context.

Common failure modes:

  • Hired "too senior" — VP who's used to 200-person teams in a 50-person function
  • Culture clash — Big-company manager who adds process that kills startup speed
  • Authority vacuum — External VP doesn't earn trust; team ignores them; founder continues to bypass hierarchy

Mitigation:

  • Hiring bar: Has this person scaled from this stage to 2x this stage before? Not managed a team at 2x — built a team to 2x.
  • Explicit onboarding on "how we make decisions here"
  • 90-day milestones focused on relationship-building before any structural changes
  • Founders explicitly hand off ownership and reinforce new manager's authority publicly

Stage 4: Founder Transition from Operator to Executive

The hardest personal transition. Founder moves from doing to enabling.

Signs you haven't made the transition:

  • You're still in every technical decision
  • Teams come to you instead of their manager for approvals
  • You know more about the team's work than the manager does
  • Managers feel they need to check in before acting

What the transition requires:

  • Explicit authority delegation in writing (not just verbal)
  • Willingness to let managers make decisions you'd make differently
  • Redirecting team members to their manager consistently
  • Measuring managers on outcomes, not just process adherence
  • Letting managers hire and fire without founder override (except final call on VPs)