
Founder Coach
- 86 installs
- 451 repo stars
- Updated July 21, 2026
- borghei/claude-skills
Founder Coach is a Claude skill for founder and first-time-CEO leadership development, covering archetypes, delegation, energy management, and the founder-mode trap.
About
Founder Coach is a Claude skill for personal leadership development of founders and first-time CEOs. It covers founder archetype identification, delegation frameworks, energy management, calendar audits, and the founder-mode trap. A founder uses it when they feel like the bottleneck, struggle to delegate, are burning out, or are transitioning from individual contributor to executive.
- Founder archetype identification and delegation-ladder frameworks
- Growth-ceiling model maps predictable founder constraints by headcount
- Covers burnout, imposter syndrome, calendar audits, and succession
Founder Coach by the numbers
- 86 all-time installs (skills.sh)
- Ranked #1,417 of 3,282 Productivity & Planning skills by installs in the Skillselion catalog
- Data as of Aug 5, 2026 (Skillselion catalog sync)
founder-coach capabilities & compatibility
Free; no API keys or external services required.
- Capabilities
- executive mentor · founder coach
- Use cases
- planning
- Pricing
- Free
What founder-coach says it does
Personal leadership development for founders and first-time CEOs.
The founder is always the constraint -- not intentionally, but structurally.
Every founder hits predictable ceilings.
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| Installs | 86 |
|---|---|
| repo stars | ★ 451 |
| Last updated | July 21, 2026 |
| Repository | borghei/claude-skills ↗ |
What it does
Diagnose a founder's growth ceiling and archetype, then build delegation, energy, and calendar plans.
Who is it for?
A founder who feels like the bottleneck, cannot delegate, is burning out, or is transitioning from individual contributor to executive.
Skip if: Building product, engineering tasks, or company-external strategy.
When should I use this skill?
A founder feels like the bottleneck, struggles to delegate, is burning out, or mentions founder mode or executive transition.
What you get
A founder with a diagnosed archetype and growth ceiling, a delegation plan, and an energy and calendar strategy.
- Founder archetype self-assessment and action plan
- Delegation-ladder plan and calendar audit
By the numbers
- 7 leadership frameworks
- 4 founder archetypes
- 4-stage growth ceiling model (15/50/150/500+ people)
Files
Founder Coach
Your company can only grow as fast as you do. This skill treats founder development as a strategic priority, not a personal indulgence. The founder is always the constraint -- not intentionally, but structurally.
Keywords
founder, CEO, founder mode, delegation, burnout, imposter syndrome, leadership growth, energy management, calendar audit, executive team, board management, succession planning, IC to manager, leadership style, founder trap, blind spots, personal OKRs, CEO reflection, co-founder dynamics, founder mental health, executive transition
---
Founder Growth Ceiling Model
Every founder hits predictable ceilings. Identifying which ceiling you are at determines what to work on.
Ceiling 1: ~15 people
Problem: Can't be in every meeting and still think
Solution: Delegate operational decisions, hire first manager
Skill to build: Letting go of execution details
Ceiling 2: ~50 people
Problem: Your style creates culture problems at scale
Solution: Hire executive team, evolve leadership style
Skill to build: Leading through others, not doing yourself
Ceiling 3: ~150 people
Problem: Need a real executive team or you become the blocker
Solution: Build institutional leadership, not personal leadership
Skill to build: System design, not personal contribution
Ceiling 4: ~500+ people
Problem: You are a symbol, not a manager
Solution: Focus on vision, board, culture, and external narrative
Skill to build: Organizational architecture---
Framework 1: Founder Archetype
Most founders are primarily one archetype. Knowing yours predicts what you will struggle with.
Archetype Matrix
| Archetype | Strength | Blind Spot | Needs | Common at Stage |
|---|---|---|---|---|
| Builder | Product, engineering, technical depth | GTM, storytelling, people | A seller / GTM partner | Seed to Series A |
| Seller | Revenue, relationships, vision communication | Operations, follow-through, process | An operator / COO | Series A to B |
| Operator | Execution, process, reliability | Vision, product intuition, risk-taking | A visionary / strategic partner | Series B+ |
| Visionary | Strategy, narrative, pattern recognition | Execution, details, grounding | An integrator / COO | All stages |
Self-Assessment Questions
| Question | Builder | Seller | Operator | Visionary |
|---|---|---|---|---|
| What do you do with a free hour? | Code/build | Call/meet someone | Organize/fix | Think/read/plan |
| What do you procrastinate on? | Sales, hiring | Admin, documentation | Ideation, risk | Follow-through |
| What does your team complain about? | Communication | Consistency | Flexibility | Details |
| What energizes you most? | Shipping | Winning deals | Solving problems | Connecting dots |
Archetype Action Plan
IF Builder:
- Hire GTM partner within next 90 days
- Schedule 2 customer-facing meetings per week (force yourself)
- Delegate code reviews to senior engineer by month 2
IF Seller:
- Hire operations leader within next 90 days
- Implement weekly review cadence (force process)
- Document decisions instead of verbal commitments
IF Operator:
- Partner with visionary co-founder or advisor
- Schedule monthly "blue sky" thinking time
- Practice saying yes to 1 risky bet per quarter
IF Visionary:
- Hire COO or integrator immediately
- Convert vision to 90-day rocks with measurable outcomes
- Review execution weekly, not just strategy quarterly---
Framework 2: Delegation
Why Founders Fail to Delegate
| Reason | Reframe |
|---|---|
| "Nobody does it as well as I do" | True short-term, fatal long-term |
| "It takes longer to explain than to do" | True once, not true the 10th time |
| "I lose control" | Control is an illusion at scale |
| "If it fails, it's my fault" | It's your fault if you never let anyone try |
The Delegation Ladder
| Level | Description | Founder Involvement | When to Use |
|---|---|---|---|
| 1 | "Do exactly what I tell you" | Total (not delegation) | Never -- this is instruction |
| 2 | "Research and report back" | High (you decide) | New topics, unfamiliar domains |
| 3 | "Propose a solution, I'll decide" | Medium (you validate) | Building trust phase |
| 4 | "Decide and tell me what you decided" | Low (you review) | Established trust |
| 5 | "Handle it, update me if outside parameters" | Minimal (you monitor) | Full delegation |
What to Delegate First (Priority Order)
| Priority | Category | Examples | Risk if You Hold |
|---|---|---|---|
| 1st | Recurring operational | Reports, scheduling, routine decisions | Your time is consumed by low-value work |
| 2nd | Information gathering | Research, analysis, data synthesis | You become the bottleneck for knowledge |
| 3rd | Relationship management | Customer interactions, partner management | Relationships depend on one person |
| 4th | Budget management | Within defined parameters | Decisions wait for your approval |
| 5th (last) | Strategic decisions | Major pivots, exec hires, large investments | These actually need you |
Delegation Decision Tree
START: Task needs to be done
|
v
[Have you done this task 3+ times?]
|
+-- YES --> [Can you write the process in < 30 minutes?]
| |
| +-- YES --> Delegate immediately (Level 3-4)
| +-- NO --> Document next time you do it, then delegate
|
+-- NO --> [Is this strategic or operational?]
|
+-- OPERATIONAL --> Delegate at Level 2-3
+-- STRATEGIC --> [Is it irreversible?]
|
+-- YES --> Keep for now. Delegate inputs.
+-- NO --> Delegate at Level 3-4---
Framework 3: Energy Management
Energy Audit Process
Map your last 2 weeks by energy impact, not just time:
| Activity Category | Energy Impact | Time Spent | Action |
|---|---|---|---|
| Deep product work | Energizing | 4 hrs/week | Protect and increase |
| 1:1s with team | Neutral | 6 hrs/week | Optimize format, reduce to 30 min |
| Admin/email/Slack | Draining | 8 hrs/week | Batch to 2x daily, delegate |
| Investor updates | Draining | 3 hrs/week | Template and delegate prep |
| Customer conversations | Energizing | 2 hrs/week | Increase to 4 hrs/week |
| Strategy thinking | Energizing | 1 hr/week | Block 4 hrs/week minimum |
Energy Rules
| Rule | Implementation |
|---|---|
| Protect deep work | 2-4 hours uninterrupted, 3-5 days/week. Calendar-blocked. |
| Batch shallow work | Email/Slack twice daily maximum |
| Know your peak window | Schedule hardest work during your 4-6 peak hours |
| Match task to energy | Low energy? Do admin. High energy? Do strategy. |
| Recovery is productive | Exercise, thinking time, breaks are not "wasted time" |
---
Framework 4: CEO Calendar Audit
Running the Audit
Pull the last 4 weeks. Categorize every block.
| Category | Description | Target % | Red Flag |
|---|---|---|---|
| Strategy | Thinking, planning, direction-setting | 20-25% | < 10% = running the company, not leading it |
| People | 1:1s, coaching, recruiting, team development | 20-25% | < 10% = team running on empty |
| External | Customers, investors, partners, industry | 20% | < 10% = losing market connection |
| Execution | Direct work, decisions, problem-solving | 15% | > 30% = still an IC |
| Admin | Email, scheduling, overhead, Slack | < 15% | > 20% = you're a coordinator |
| Recovery | Exercise, meals, breaks, thinking | 10-15% | 0% = burnout approaching |
CEO Primary Job by Stage
| Stage | CEO Should Spend Most Time On | If You're Not |
|---|---|---|
| Seed | Product and customers, directly | You're building in a vacuum |
| Series A | Hiring the executive team | You'll hit Ceiling 2 without leaders |
| Series B | Culture, strategy, external | Your company outgrows your direct management |
| Series C+ | Vision, board, external narrative | Your job is organizational, not operational |
---
Framework 5: Leadership Style Evolution
Evolution Matrix
| Transition | From | To | Critical Skill | Common Failure |
|---|---|---|---|---|
| IC to Manager (0-10) | Doing | Teaching | Give context + set expectations | Doing everything yourself |
| Manager to Leader (10-50) | Managing | Hiring managers | Trust people you're still learning | Micromanaging managers |
| Leader to Executive (50-200) | Directing | Setting culture and direction | Communicate obsessively | Still managing individual work |
| Executive to CEO (200+) | Leading internally | Leading externally | Build systems without you | Refusing to let go of internal ops |
Transition Readiness Checklist
| Transition | Ready When | Not Ready When |
|---|---|---|
| IC to Manager | Can describe 3 team members' career goals | Still doing all the critical work yourself |
| Manager to Leader | 2+ managers you trust to run their teams | Override every manager's decision |
| Leader to Executive | Leadership team can run company for 2 weeks | Every decision needs your approval |
| Executive to CEO | Board operates effectively, team is self-correcting | You are the only external face |
---
Framework 6: Blind Spot Detection
Common Founder Blind Spots
| Blind Spot | Symptom | Detection Method |
|---|---|---|
| Communication gap | "I said it once, they should know" | Ask team to repeat your priorities. Do they match? |
| Speed disease | Teams can't orient on your direction | Track how many initiatives change per quarter |
| Context hoarding | Bad decisions by teams who lack information | Ask "what info did you wish you had?" |
| Optimism bias | Consistently miss timelines and targets | Compare estimates to actuals over 6 months |
| Founder exceptionalism | Rules apply to everyone except you | Ask team: "Does the founder follow the same rules?" |
| Feedback avoidance | No honest feedback from anyone | Run anonymous 360 with one hard question |
360 Feedback Protocol
Run annually. Include these questions:
| Question | Purpose |
|---|---|
| "What does [founder] do that helps the company most?" | Identify strengths to leverage |
| "What does [founder] do that gets in the way?" | Surface blind spots |
| "What should [founder] stop doing?" | Identify delegation opportunities |
| "What should [founder] start doing?" | Identify gaps |
| "If you could change one thing about working with [founder], what?" | Single most impactful change |
---
Framework 7: Imposter Syndrome Toolkit
The Reframe
Imposter syndrome is proportional to stretch. If you never feel it, you are not growing.
| Stage | Imposter Trigger | Reframe |
|---|---|---|
| First hire | "I've never managed anyone" | Competence comes from doing, not feeling ready |
| First fundraise | "Real founders are more polished" | Investors bet on trajectory, not current state |
| First exec hire | "They have more experience than me" | You hired them because they're good. Let them be. |
| First board meeting | "They'll see through me" | Preparation is the antidote. Use board prep. |
| Growth stage | "Company has outgrown me" | Maybe. Or maybe you just need to grow. Investigate. |
Practical Tools
| Tool | How | When |
|---|---|---|
| Evidence file | Document wins, compliments, correct decisions | Read when doubt hits |
| Name it | Say "I'm feeling imposter syndrome about X" to someone | Removes 50% of its power |
| Do it anyway | Act despite feeling unready | Competence follows action |
| Separate feeling from fact | "I feel underprepared" is not "I am incapable" | Always |
---
Framework 8: Founder Mental Health
Burnout Signal Progression
| Stage | Signals | Action |
|---|---|---|
| Early | Irritability, poor sleep, decisions feel harder | Adjust calendar, protect recovery time |
| Mid | Physical symptoms, cynicism, priority paralysis | Reduce commitments, start therapy/coaching |
| Late | Can't function, decisions stopped, team notices | Full stop. Get professional support. Now. |
Structural Prevention
| Practice | Implementation |
|---|---|
| Protected recovery | Non-negotiable time during the week (not just weekends) |
| Therapy or coaching | Not optional. The job is isolating. |
| Peer group | Other founders at similar stage. Only people who truly understand. |
| Clear off-ramps | Define "enough for today." Don't let work be infinite. |
| Physical health | Exercise, sleep, nutrition. Non-negotiable foundations. |
---
Framework 9: The Founder Mode Trap
When Founder Mode Helps vs. Hurts
| Situation | Helps | Hurts |
|---|---|---|
| Crisis recovery | Yes -- direct leadership needed | -- |
| PMF search | Yes -- speed matters more than org health | -- |
| Irreversible decisions | Yes -- you should be in the room | -- |
| Undermining hired managers | -- | Yes -- they can't lead if you override |
| Driven by distrust | -- | Yes -- trust is a prerequisite for scale |
| Preventing team development | -- | Yes -- team never builds judgment |
The Test
"Am I going deep because the situation requires it, or because I am uncomfortable with loss of control?"
The first is leadership. The second is the trap.
---
Framework 10: Succession Planning
Succession Readiness Levels
| Level | Description | Timeline |
|---|---|---|
| 0 | Founder is the only person who knows how things work | Most founders are here. Dangerous. |
| 1 | Key knowledge and processes are documented | 30-day project |
| 2 | At least one person can cover each key function for 2 weeks | 90-day project |
| 3 | Leadership team can run the company for a quarter | 6-12 month development |
| 4 | Potential successor identified and being developed | 12-24 months |
Target: Level 2 is a reasonable near-term target. Level 3 is a strategic asset.
---
Red Flags
- Making the same decisions you were making 12 months ago -- you haven't delegated
- Calendar audit shows > 30% execution at Series B+ -- still an IC
- No honest feedback received in 6+ months -- feedback vacuum
- Working 70+ hours consistently -- burnout is a when, not an if
- Team waits for your input on everything -- delegation failure
- Can't name your top 3 blind spots -- self-awareness gap
- No peer group of other founders -- isolation risk
- Succession readiness at Level 0 -- company depends entirely on you
- Co-founder tension unaddressed for 30+ days -- will get worse, never better
---
Integration with C-Suite
| When... | Founder Coach Works With... | To... |
|---|---|---|
| Building exec team | CHRO (chro-advisor) | Hiring criteria, onboarding execs |
| Leadership evolution | CEO Advisor (ceo-advisor) | Strategic leadership development |
| Decision quality | Executive Mentor (executive-mentor) | Stress-testing founder decisions |
| Culture impact | Culture Architect (culture-architect) | Founder behavior's effect on culture |
| Board management | Board Deck Builder (board-deck-builder) | Preparing for board interactions |
| Org design | COO (coo-advisor) | Structure that reduces founder dependency |
---
Output Artifacts
| Request | Deliverable |
|---|---|
| "I feel like the bottleneck" | Archetype assessment + delegation plan with specific tasks |
| "Help me delegate" | Delegation ladder for current tasks + accountability structure |
| "I'm burning out" | Energy audit + calendar redesign + recovery plan |
| "Audit my calendar" | Calendar analysis with target vs. actual time allocation |
| "Am I growing as a leader?" | 360 feedback design + leadership evolution roadmap |
| "What are my blind spots?" | Blind spot assessment with detection methods |
| "Plan for my succession" | Succession readiness assessment + development plan |
---
Troubleshooting
| Problem | Likely Cause | Resolution |
|---|---|---|
| Founder refuses to delegate despite knowing they should | Identity tied to execution; fear of irrelevance | Use the Co-Active coaching reframe: "Your value is multiplied through others, not diminished"; start with one low-risk delegation at Level 3 |
| Calendar audit shows improvement but founder still feels overwhelmed | Energy management not addressed alongside time allocation | Run energy audit in parallel; reallocate based on energy impact, not just time categories |
| Archetype assessment feels inaccurate | Founder is a hybrid or in transition between archetypes | Score across all four archetypes; most founders are 60/40 blend; focus on the dominant blind spot |
| Delegation repeatedly fails (delegate drops the ball) | Delegating at wrong level; insufficient context provided | Move down one delegation ladder level; ensure context document exists; check if the right person was chosen |
| Founder reports burnout symptoms but won't reduce workload | Structural dependency on founder; no capable backup | Build succession readiness to Level 2 first; hire specific capability gaps before reducing hours |
| Co-founder conflict escalating despite awareness | Avoiding the direct conversation; hoping it resolves | Apply Hard Call framework from Executive Mentor; set 48-hour deadline for direct conversation with structured agenda |
| Leadership evolution stalls at IC-to-Manager transition | Founder keeps doing the work instead of coaching the team | Remove founder from execution entirely for 2 weeks as forced experiment; track what breaks vs. what thrives |
---
Success Criteria
- Founder correctly identifies their primary archetype and has an active plan addressing their top blind spot within 30 days
- Delegation ladder shows measurable progression: at least 3 tasks moved up one level per quarter
- Calendar audit shows time allocation within 5% of stage-appropriate targets after 90 days
- Energy audit results in net-positive energy balance: more energizing activities than draining ones
- 360 feedback scores improve by at least 1 point on the identified blind spot dimension within 6 months
- Succession readiness advances at least one level within 12 months
- Burnout signal progression stays at Early stage or better; no founder reaches Late stage
---
Scope & Limitations
- In scope: Founder personal development, archetype identification, delegation coaching, energy management, calendar optimization, leadership evolution, blind spot detection, imposter syndrome support, mental health awareness, succession planning
- Out of scope: Clinical therapy (refer to licensed therapist for mental health treatment); couples counseling for co-founder relationships (refer to specialized mediator); executive recruiting (use CHRO Advisor); compensation design; legal aspects of founder transitions
- Limitation: Self-assessment accuracy depends on founder honesty; 360 feedback provides external validation
- Limitation: Growth ceiling model is stage-based approximation; actual ceilings vary by industry, culture, and individual
- Limitation: Wellness indicators are screening tools, not clinical diagnostics; always refer to professionals for mental health concerns
---
Integration Points
| Skill | Integration | Data Flow |
|---|---|---|
executive-mentor | Stress-testing founder decisions reveals development needs | Mentor challenges → Coach development areas |
ceo-advisor | Strategic leadership development aligns with CEO advisory | Coach leadership gaps → CEO strategic focus |
chro-advisor | Executive team hiring criteria informed by founder blind spots | Coach archetype gaps → CHRO hiring profile |
culture-architect | Founder behavior directly shapes culture | Coach behavior changes → Culture evolution |
chief-of-staff | Chief of Staff can handle delegation overflow | Coach delegation plan → CoS task assignment |
org-health-diagnostic | People health dimension reflects founder leadership quality | Health people score → Coach priority areas |
---
Python Tools
| Tool | Purpose | Usage |
|---|---|---|
scripts/startup_stage_assessor.py | Assess current startup stage and identify the founder growth ceiling being approached | python scripts/startup_stage_assessor.py --headcount 35 --arr 1200000 --stage series-a --json |
scripts/founder_wellness_checker.py | Screen for burnout signals across early/mid/late stages with actionable recommendations | python scripts/founder_wellness_checker.py --hours-per-week 65 --sleep-hours 5.5 --exercise-days 1 --json |
scripts/milestone_tracker.py | Track founder development milestones across delegation, leadership evolution, and succession readiness | python scripts/milestone_tracker.py add --category delegation --milestone "Hired first manager" --json |
#!/usr/bin/env python3
"""Founder Wellness Checker - Screen for burnout signals with actionable recommendations.
Evaluates founder wellness across work intensity, sleep, exercise, social connection,
and stress indicators. Maps to Early/Mid/Late burnout stages with specific interventions.
Usage:
python founder_wellness_checker.py --hours-per-week 65 --sleep-hours 5.5 --exercise-days 1
python founder_wellness_checker.py --hours-per-week 55 --sleep-hours 7 --exercise-days 3 --has-peer-group --has-coach --json
"""
import argparse
import json
import sys
from datetime import datetime
FACTORS = {
"work_hours": {
"name": "Work Intensity",
"thresholds": {"green": 50, "yellow": 60, "red": 70},
"direction": "lower_is_better",
"unit": "hours/week"
},
"sleep": {
"name": "Sleep Quality",
"thresholds": {"green": 7, "yellow": 6, "red": 5},
"direction": "higher_is_better",
"unit": "hours/night"
},
"exercise": {
"name": "Physical Activity",
"thresholds": {"green": 3, "yellow": 2, "red": 1},
"direction": "higher_is_better",
"unit": "days/week"
},
"peer_group": {
"name": "Peer Support",
"description": "Regular founder peer group or trusted advisor network"
},
"professional_support": {
"name": "Professional Support",
"description": "Therapist, coach, or similar professional relationship"
},
"vacation_days": {
"name": "Recovery Time",
"thresholds": {"green": 15, "yellow": 7, "red": 3},
"direction": "higher_is_better",
"unit": "days in last 6 months"
},
"decision_fatigue": {
"name": "Decision Fatigue",
"thresholds": {"green": 3, "yellow": 5, "red": 7},
"direction": "lower_is_better",
"unit": "self-rated 1-10"
}
}
BURNOUT_STAGES = {
"healthy": {
"label": "Healthy",
"description": "Sustainable pace with adequate recovery",
"color": "GREEN",
"recommendations": [
"Maintain current habits -- they are working",
"Schedule quarterly check-ins to ensure sustainability",
"Consider helping other founders build similar habits"
]
},
"early": {
"label": "Early Warning",
"description": "Irritability, poor sleep, decisions feel harder than usual",
"color": "YELLOW",
"recommendations": [
"Adjust calendar: protect recovery time this week",
"Reduce commitments by 20% for the next 2 weeks",
"Re-establish exercise routine (even 20 min walks count)",
"Block 'off' hours and communicate them to your team",
"Schedule 1 social activity unrelated to work this week"
]
},
"mid": {
"label": "Mid-Stage Burnout",
"description": "Physical symptoms, cynicism, priority paralysis, reduced effectiveness",
"color": "ORANGE",
"recommendations": [
"Reduce work hours to < 50 this week (non-negotiable)",
"Start therapy or coaching if not already active",
"Delegate 3 responsibilities immediately (use delegation ladder)",
"Take at least 2 consecutive days off within 2 weeks",
"Inform a trusted board member or advisor of your state",
"Audit all commitments and cancel or postpone 30%"
]
},
"late": {
"label": "Late-Stage Burnout",
"description": "Cannot function effectively, decisions stopped, team notices dysfunction",
"color": "RED",
"recommendations": [
"STOP. Get professional support immediately (therapist or doctor)",
"Inform your co-founder, board chair, or most trusted advisor today",
"Delegate ALL operational responsibilities for at least 2 weeks",
"Do not make any major decisions until recovery begins",
"Consider a structured leave with clear communication to team",
"This is not weakness -- this is a medical and operational necessity"
]
}
}
def calculate_wellness(hours, sleep, exercise, has_peer_group, has_coach,
vacation_days, decision_fatigue):
scores = {}
risk_factors = []
protective_factors = []
# Work hours
if hours <= 50:
scores["work_hours"] = {"score": 9, "status": "green"}
elif hours <= 60:
scores["work_hours"] = {"score": 6, "status": "yellow"}
risk_factors.append(f"Working {hours} hrs/week -- approaching unsustainable")
elif hours <= 70:
scores["work_hours"] = {"score": 3, "status": "orange"}
risk_factors.append(f"Working {hours} hrs/week -- unsustainable pace")
else:
scores["work_hours"] = {"score": 1, "status": "red"}
risk_factors.append(f"Working {hours} hrs/week -- burnout is a when, not if")
# Sleep
if sleep >= 7:
scores["sleep"] = {"score": 9, "status": "green"}
protective_factors.append("Adequate sleep (7+ hours)")
elif sleep >= 6:
scores["sleep"] = {"score": 5, "status": "yellow"}
risk_factors.append(f"Sleep at {sleep} hrs -- cognitive impairment begins below 7")
else:
scores["sleep"] = {"score": 2, "status": "red"}
risk_factors.append(f"Sleep at {sleep} hrs -- severe cognitive and health impact")
# Exercise
if exercise >= 3:
scores["exercise"] = {"score": 9, "status": "green"}
protective_factors.append(f"Regular exercise ({exercise} days/week)")
elif exercise >= 2:
scores["exercise"] = {"score": 5, "status": "yellow"}
risk_factors.append("Exercise below recommended minimum (3+ days)")
elif exercise >= 1:
scores["exercise"] = {"score": 3, "status": "orange"}
risk_factors.append("Minimal exercise -- stress relief compromised")
else:
scores["exercise"] = {"score": 1, "status": "red"}
risk_factors.append("No exercise -- critical protective factor missing")
# Peer group
if has_peer_group:
scores["peer_group"] = {"score": 8, "status": "green"}
protective_factors.append("Active peer support network")
else:
scores["peer_group"] = {"score": 3, "status": "orange"}
risk_factors.append("No peer group -- isolation risk")
# Professional support
if has_coach:
scores["professional_support"] = {"score": 8, "status": "green"}
protective_factors.append("Professional support (coach/therapist)")
else:
scores["professional_support"] = {"score": 4, "status": "yellow"}
risk_factors.append("No professional support -- the job is isolating")
# Vacation
if vacation_days >= 15:
scores["vacation"] = {"score": 9, "status": "green"}
protective_factors.append(f"{vacation_days} recovery days in 6 months")
elif vacation_days >= 7:
scores["vacation"] = {"score": 5, "status": "yellow"}
risk_factors.append(f"Only {vacation_days} days off in 6 months -- insufficient recovery")
else:
scores["vacation"] = {"score": 2, "status": "red"}
risk_factors.append(f"Only {vacation_days} days off in 6 months -- no recovery happening")
# Decision fatigue
if decision_fatigue <= 3:
scores["decision_fatigue"] = {"score": 8, "status": "green"}
elif decision_fatigue <= 5:
scores["decision_fatigue"] = {"score": 5, "status": "yellow"}
risk_factors.append("Moderate decision fatigue -- delegate more operational decisions")
elif decision_fatigue <= 7:
scores["decision_fatigue"] = {"score": 3, "status": "orange"}
risk_factors.append("High decision fatigue -- decision quality declining")
else:
scores["decision_fatigue"] = {"score": 1, "status": "red"}
risk_factors.append("Severe decision fatigue -- decisions are being avoided or delayed")
# Overall wellness score
total = sum(s["score"] for s in scores.values())
max_total = len(scores) * 10
wellness_pct = round(total / max_total * 100)
# Determine burnout stage
red_count = sum(1 for s in scores.values() if s["status"] == "red")
orange_count = sum(1 for s in scores.values() if s["status"] == "orange")
if red_count >= 3 or (red_count >= 2 and orange_count >= 2):
stage = "late"
elif red_count >= 1 or orange_count >= 2:
stage = "mid"
elif orange_count >= 1 or len(risk_factors) >= 3:
stage = "early"
else:
stage = "healthy"
burnout_info = BURNOUT_STAGES[stage]
return {
"assessment_date": datetime.now().strftime("%Y-%m-%d"),
"inputs": {
"hours_per_week": hours,
"sleep_hours": sleep,
"exercise_days": exercise,
"has_peer_group": has_peer_group,
"has_professional_support": has_coach,
"vacation_days_6mo": vacation_days,
"decision_fatigue": decision_fatigue
},
"wellness_score": wellness_pct,
"burnout_stage": stage,
"burnout_label": burnout_info["label"],
"burnout_description": burnout_info["description"],
"severity": burnout_info["color"],
"factor_scores": scores,
"risk_factors": risk_factors,
"protective_factors": protective_factors,
"recommendations": burnout_info["recommendations"]
}
def print_human(result):
print(f"\n{'='*70}")
print(f"FOUNDER WELLNESS CHECK")
print(f"Date: {result['assessment_date']}")
print(f"{'='*70}\n")
print(f"WELLNESS SCORE: {result['wellness_score']}%")
print(f"BURNOUT STAGE: [{result['severity']}] {result['burnout_label']}")
print(f" {result['burnout_description']}\n")
print("FACTOR SCORES:")
print("-" * 50)
status_icons = {"green": "+", "yellow": "~", "orange": "!", "red": "X"}
for key, data in result["factor_scores"].items():
icon = status_icons.get(data["status"], "?")
print(f" [{icon}] {key:<25s} {data['score']:>2}/10 ({data['status']})")
if result["risk_factors"]:
print(f"\nRISK FACTORS ({len(result['risk_factors'])}):")
for r in result["risk_factors"]:
print(f" [!] {r}")
if result["protective_factors"]:
print(f"\nPROTECTIVE FACTORS ({len(result['protective_factors'])}):")
for p in result["protective_factors"]:
print(f" [+] {p}")
print(f"\nRECOMMENDATIONS:")
print("-" * 50)
for r in result["recommendations"]:
print(f" -> {r}")
print()
def main():
parser = argparse.ArgumentParser(description="Screen for founder burnout signals")
parser.add_argument("--hours-per-week", type=float, required=True, help="Average work hours per week")
parser.add_argument("--sleep-hours", type=float, required=True, help="Average sleep hours per night")
parser.add_argument("--exercise-days", type=int, required=True, help="Exercise days per week (0-7)")
parser.add_argument("--has-peer-group", action="store_true", help="Has active founder peer group")
parser.add_argument("--has-coach", action="store_true", help="Has therapist, coach, or professional support")
parser.add_argument("--vacation-days", type=int, default=5, help="Days off in last 6 months")
parser.add_argument("--decision-fatigue", type=int, default=5, help="Decision fatigue self-rating (1-10)")
parser.add_argument("--json", action="store_true", help="Output as JSON")
args = parser.parse_args()
result = calculate_wellness(
args.hours_per_week, args.sleep_hours, args.exercise_days,
args.has_peer_group, args.has_coach,
args.vacation_days, args.decision_fatigue
)
if args.json:
print(json.dumps(result, indent=2))
else:
print_human(result)
if __name__ == "__main__":
main()
#!/usr/bin/env python3
"""Milestone Tracker - Track founder development milestones across key areas.
Track progress on delegation, leadership evolution, succession readiness, and
personal development milestones. Stored in local JSON for persistence.
Usage:
python milestone_tracker.py add --category delegation --milestone "Hired first manager"
python milestone_tracker.py list --category leadership
python milestone_tracker.py progress
python milestone_tracker.py report --json
"""
import argparse
import json
import os
import sys
from datetime import datetime
DEFAULT_STORE = os.path.join(os.path.dirname(os.path.abspath(__file__)), "milestones_data.json")
CATEGORIES = {
"delegation": {
"name": "Delegation Progress",
"milestones": [
"Identified 5 tasks to delegate",
"Hired first manager",
"3 tasks at delegation Level 3",
"Written decision parameters for direct reports",
"5+ tasks at Level 4-5",
"Calendar shows < 15% execution time",
"Team makes decisions without waiting for founder"
]
},
"leadership": {
"name": "Leadership Evolution",
"milestones": [
"Transitioned from IC to Manager (teaching not doing)",
"Hired 2+ managers you trust",
"Leadership team can run company for 2 weeks",
"Built institutional leadership systems",
"Potential successor identified",
"Can articulate leadership style and blind spots",
"360 feedback shows improving leadership scores"
]
},
"succession": {
"name": "Succession Readiness",
"milestones": [
"Level 0: Key knowledge documented",
"Level 1: Processes written down",
"Level 2: Someone can cover each key function for 2 weeks",
"Level 3: Leadership team runs company for a quarter",
"Level 4: Potential successor identified and developing"
]
},
"wellbeing": {
"name": "Founder Wellbeing",
"milestones": [
"Established exercise routine (3+ days/week)",
"Sleep consistently 7+ hours",
"Joined founder peer group",
"Started therapy or coaching",
"Protected recovery time on calendar",
"Took 5+ consecutive days off",
"Work hours consistently under 55/week"
]
},
"self_awareness": {
"name": "Self-Awareness Development",
"milestones": [
"Completed founder archetype assessment",
"Identified top 3 blind spots",
"Ran first 360 feedback",
"Created evidence file (wins, mistakes, patterns)",
"Active mitigation strategy for each blind spot",
"Re-ran 360 showing improvement",
"Modeling vulnerability with team"
]
}
}
def load_data(store_path):
if os.path.exists(store_path):
with open(store_path, "r") as f:
return json.load(f)
return {"milestones": [], "next_id": 1}
def save_data(data, store_path):
with open(store_path, "w") as f:
json.dump(data, f, indent=2)
def add_milestone(data, category, milestone_text, notes=""):
milestone = {
"id": data["next_id"],
"category": category,
"milestone": milestone_text,
"achieved": True,
"date_achieved": datetime.now().strftime("%Y-%m-%d"),
"notes": notes
}
data["milestones"].append(milestone)
data["next_id"] += 1
return milestone
def list_milestones(data, category=None):
milestones = data["milestones"]
if category:
milestones = [m for m in milestones if m["category"] == category]
return milestones
def calculate_progress(data):
progress = {}
for cat_key, cat_info in CATEGORIES.items():
total = len(cat_info["milestones"])
achieved = len([m for m in data["milestones"] if m["category"] == cat_key])
pct = round(achieved / total * 100) if total > 0 else 0
progress[cat_key] = {
"name": cat_info["name"],
"total_milestones": total,
"achieved": min(achieved, total),
"percentage": min(pct, 100),
"remaining": [
ms for ms in cat_info["milestones"]
if not any(m["milestone"] == ms for m in data["milestones"] if m["category"] == cat_key)
]
}
return progress
def generate_report(data):
progress = calculate_progress(data)
recent = sorted(data["milestones"], key=lambda m: m["date_achieved"], reverse=True)[:5]
total_possible = sum(len(c["milestones"]) for c in CATEGORIES.values())
total_achieved = len(data["milestones"])
overall_pct = round(total_achieved / total_possible * 100) if total_possible > 0 else 0
# Find weakest area
weakest = min(progress.values(), key=lambda p: p["percentage"])
strongest = max(progress.values(), key=lambda p: p["percentage"])
return {
"report_date": datetime.now().strftime("%Y-%m-%d"),
"overall_progress": min(overall_pct, 100),
"total_milestones_achieved": total_achieved,
"total_milestones_possible": total_possible,
"category_progress": progress,
"recent_achievements": [
{"milestone": m["milestone"], "category": m["category"], "date": m["date_achieved"]}
for m in recent
],
"weakest_area": {"name": weakest["name"], "percentage": weakest["percentage"]},
"strongest_area": {"name": strongest["name"], "percentage": strongest["percentage"]},
"next_recommended": weakest["remaining"][:2] if weakest["remaining"] else []
}
def print_progress_human(progress):
print(f"\n{'='*60}")
print(f"FOUNDER DEVELOPMENT PROGRESS")
print(f"{'='*60}\n")
for cat_key, data in progress.items():
bar_filled = int(data["percentage"] / 5)
bar = "#" * bar_filled + "." * (20 - bar_filled)
print(f" {data['name']:<30s} [{bar}] {data['percentage']:>3}% ({data['achieved']}/{data['total_milestones']})")
if data["remaining"]:
print(f" Next: {data['remaining'][0]}")
print()
def print_report_human(report):
print(f"\n{'='*60}")
print(f"MILESTONE TRACKER REPORT - {report['report_date']}")
print(f"{'='*60}\n")
print(f"Overall Progress: {report['overall_progress']}% ({report['total_milestones_achieved']}/{report['total_milestones_possible']})")
print(f"Strongest: {report['strongest_area']['name']} ({report['strongest_area']['percentage']}%)")
print(f"Weakest: {report['weakest_area']['name']} ({report['weakest_area']['percentage']}%)\n")
print("CATEGORY BREAKDOWN:")
print("-" * 50)
for cat_key, data in report["category_progress"].items():
bar_filled = int(data["percentage"] / 5)
bar = "#" * bar_filled + "." * (20 - bar_filled)
print(f" {data['name']:<30s} [{bar}] {data['percentage']:>3}%")
if report["recent_achievements"]:
print(f"\nRECENT ACHIEVEMENTS:")
for a in report["recent_achievements"]:
print(f" [{a['date']}] {a['category']}: {a['milestone']}")
if report["next_recommended"]:
print(f"\nNEXT RECOMMENDED MILESTONES:")
for m in report["next_recommended"]:
print(f" [ ] {m}")
print()
def main():
parser = argparse.ArgumentParser(description="Track founder development milestones")
subparsers = parser.add_subparsers(dest="command")
add_p = subparsers.add_parser("add", help="Record a milestone achievement")
add_p.add_argument("--category", required=True, choices=list(CATEGORIES.keys()))
add_p.add_argument("--milestone", required=True, help="Milestone description")
add_p.add_argument("--notes", default="", help="Additional notes")
add_p.add_argument("--json", action="store_true")
add_p.add_argument("--store", default=DEFAULT_STORE)
list_p = subparsers.add_parser("list", help="List milestones")
list_p.add_argument("--category", choices=list(CATEGORIES.keys()))
list_p.add_argument("--json", action="store_true")
list_p.add_argument("--store", default=DEFAULT_STORE)
prog_p = subparsers.add_parser("progress", help="Show progress across categories")
prog_p.add_argument("--json", action="store_true")
prog_p.add_argument("--store", default=DEFAULT_STORE)
rep_p = subparsers.add_parser("report", help="Full progress report")
rep_p.add_argument("--json", action="store_true")
rep_p.add_argument("--store", default=DEFAULT_STORE)
args = parser.parse_args()
if not args.command:
parser.print_help()
sys.exit(1)
data = load_data(args.store)
if args.command == "add":
m = add_milestone(data, args.category, args.milestone, args.notes)
save_data(data, args.store)
if args.json:
print(json.dumps(m, indent=2))
else:
print(f"Milestone #{m['id']} recorded: {m['milestone']}")
elif args.command == "list":
milestones = list_milestones(data, args.category)
if args.json:
print(json.dumps(milestones, indent=2))
else:
if not milestones:
print("No milestones recorded.")
else:
for m in milestones:
print(f" [{m['date_achieved']}] #{m['id']} {m['category']}: {m['milestone']}")
elif args.command == "progress":
progress = calculate_progress(data)
if args.json:
print(json.dumps(progress, indent=2))
else:
print_progress_human(progress)
elif args.command == "report":
report = generate_report(data)
if args.json:
print(json.dumps(report, indent=2))
else:
print_report_human(report)
if __name__ == "__main__":
main()
#!/usr/bin/env python3
"""Startup Stage Assessor - Assess current startup stage and identify founder growth ceiling.
Evaluates company stage based on headcount, ARR, funding, and operational signals.
Maps the founder to their current growth ceiling and provides development recommendations.
Usage:
python startup_stage_assessor.py --headcount 35 --arr 1200000 --stage series-a
python startup_stage_assessor.py --headcount 120 --arr 8000000 --stage series-b --has-exec-team --json
"""
import argparse
import json
import sys
from datetime import datetime
CEILINGS = {
1: {
"threshold": 15,
"name": "Ceiling 1: Direct Leadership Limit (~15 people)",
"problem": "Can't be in every meeting and still think strategically",
"solution": "Delegate operational decisions, hire first manager",
"skill_to_build": "Letting go of execution details",
"signals": [
"You attend > 80% of meetings in the company",
"Every decision waits for your input",
"You are the only person who talks to customers, investors, AND the team",
"No written processes exist -- everything is in your head"
],
"actions": [
"Hire your first manager within 60 days",
"Document top 5 processes you do repeatedly",
"Delegate one customer-facing responsibility to a team member",
"Block 4 hours/week for thinking time (not meetings)"
]
},
2: {
"threshold": 50,
"name": "Ceiling 2: Management Layer (~50 people)",
"problem": "Your personal style creates culture problems at scale",
"solution": "Hire executive team, evolve leadership style",
"skill_to_build": "Leading through others, not doing yourself",
"signals": [
"New hires don't understand the culture because it was never written down",
"You micromanage managers because you don't trust their judgment yet",
"Team coordination requires you as the hub",
"Hiring is the biggest bottleneck and you are the only interviewer"
],
"actions": [
"Hire 2-3 executives who complement your archetype blind spots",
"Define and document company values with leadership team",
"Implement manager training for new managers",
"Establish weekly leadership team cadence"
]
},
3: {
"threshold": 150,
"name": "Ceiling 3: Institutional Leadership (~150 people)",
"problem": "Need a real executive team or you become the permanent blocker",
"solution": "Build institutional leadership, not personal leadership",
"skill_to_build": "System design, not personal contribution",
"signals": [
"Company cannot function for 2 weeks without you",
"Executive team defers to you on all cross-functional decisions",
"Culture is 'what the founder does' not 'what the company does'",
"Board interactions consume too much of your time"
],
"actions": [
"Build leadership team that can run company for a quarter without you",
"Implement company operating system (planning cadence, review rhythm)",
"Develop succession plan for your role",
"Focus your time on vision, board, culture, and external narrative"
]
},
4: {
"threshold": 500,
"name": "Ceiling 4: Organizational Architecture (500+ people)",
"problem": "You are a symbol, not a manager -- and must embrace that",
"solution": "Focus on vision, board, culture, and external narrative",
"skill_to_build": "Organizational architecture and external leadership",
"signals": [
"Multiple layers between you and execution teams",
"Your decisions have weeks of ripple effects across the org",
"External stakeholders (press, analysts, partners) demand significant time",
"Internal communications must be carefully crafted, not casual"
],
"actions": [
"Delegate all internal operations to COO/President",
"Spend 50%+ of time on external: board, investors, partnerships, vision",
"Build world-class executive team that operates independently",
"Focus on 2-3 year strategic horizon, not quarterly execution"
]
}
}
STAGES = {
"pre-seed": {"arr_range": (0, 100000), "headcount_range": (1, 5), "typical_ceiling": 1},
"seed": {"arr_range": (0, 500000), "headcount_range": (2, 15), "typical_ceiling": 1},
"series-a": {"arr_range": (500000, 3000000), "headcount_range": (10, 50), "typical_ceiling": 2},
"series-b": {"arr_range": (3000000, 15000000), "headcount_range": (30, 150), "typical_ceiling": 3},
"series-c": {"arr_range": (15000000, 50000000), "headcount_range": (80, 300), "typical_ceiling": 3},
"growth": {"arr_range": (50000000, 999999999), "headcount_range": (200, 5000), "typical_ceiling": 4},
}
def assess(headcount, arr, stage, has_exec_team, has_documented_processes, founder_in_meetings_pct):
# Determine current ceiling
current_ceiling = 1
for ceiling_num, ceiling_data in CEILINGS.items():
if headcount <= ceiling_data["threshold"]:
current_ceiling = ceiling_num
break
else:
current_ceiling = 4
# Determine approaching ceiling
approaching = current_ceiling
for ceiling_num, ceiling_data in CEILINGS.items():
if headcount >= ceiling_data["threshold"] * 0.7:
approaching = ceiling_num
if ceiling_num < 4:
approaching = ceiling_num + 1
ceiling_data = CEILINGS[current_ceiling]
# Stage alignment check
stage_info = STAGES.get(stage, STAGES["seed"])
arr_aligned = stage_info["arr_range"][0] <= arr <= stage_info["arr_range"][1]
headcount_aligned = stage_info["headcount_range"][0] <= headcount <= stage_info["headcount_range"][1]
# Risk signals
risks = []
if founder_in_meetings_pct > 70 and headcount > 15:
risks.append("Founder in too many meetings for company size -- delegation gap")
if not has_exec_team and headcount > 30:
risks.append("No executive team at 30+ headcount -- approaching Ceiling 2 without leaders")
if not has_documented_processes and headcount > 15:
risks.append("No documented processes -- knowledge is trapped in founder's head")
if not arr_aligned:
risks.append(f"ARR ${arr:,} is outside expected range for {stage} (${stage_info['arr_range'][0]:,}-${stage_info['arr_range'][1]:,})")
if not headcount_aligned:
risks.append(f"Headcount {headcount} is outside expected range for {stage} ({stage_info['headcount_range'][0]}-{stage_info['headcount_range'][1]})")
# Readiness score
readiness_score = 10
if not has_exec_team and current_ceiling >= 2:
readiness_score -= 3
if not has_documented_processes:
readiness_score -= 2
if founder_in_meetings_pct > 60:
readiness_score -= 2
if len(risks) > 2:
readiness_score -= 2
readiness_score = max(1, readiness_score)
return {
"assessment_date": datetime.now().strftime("%Y-%m-%d"),
"company_metrics": {
"headcount": headcount,
"arr": arr,
"funding_stage": stage,
"has_exec_team": has_exec_team,
"has_documented_processes": has_documented_processes,
"founder_meeting_percentage": founder_in_meetings_pct
},
"current_ceiling": {
"number": current_ceiling,
"name": ceiling_data["name"],
"problem": ceiling_data["problem"],
"solution": ceiling_data["solution"],
"skill_to_build": ceiling_data["skill_to_build"]
},
"ceiling_signals": ceiling_data["signals"],
"recommended_actions": ceiling_data["actions"],
"stage_alignment": {
"arr_aligned": arr_aligned,
"headcount_aligned": headcount_aligned,
"expected_arr_range": f"${stage_info['arr_range'][0]:,} - ${stage_info['arr_range'][1]:,}",
"expected_headcount_range": f"{stage_info['headcount_range'][0]} - {stage_info['headcount_range'][1]}"
},
"risks": risks,
"readiness_score": readiness_score,
"readiness_label": "Ready" if readiness_score >= 7 else "Preparing" if readiness_score >= 4 else "At Risk"
}
def print_human(result):
print(f"\n{'='*70}")
print(f"STARTUP STAGE ASSESSMENT")
print(f"Date: {result['assessment_date']}")
print(f"{'='*70}\n")
m = result["company_metrics"]
print(f"COMPANY: {m['headcount']} people | ${m['arr']:,} ARR | {m['funding_stage']}")
print(f"Exec Team: {'Yes' if m['has_exec_team'] else 'No'} | Documented Processes: {'Yes' if m['has_documented_processes'] else 'No'}")
print(f"Founder in meetings: {m['founder_meeting_percentage']}%\n")
c = result["current_ceiling"]
print(f"CURRENT CEILING: {c['name']}")
print(f" Problem: {c['problem']}")
print(f" Solution: {c['solution']}")
print(f" Skill: {c['skill_to_build']}\n")
print("SIGNALS TO WATCH:")
for s in result["ceiling_signals"]:
print(f" - {s}")
print("\nRECOMMENDED ACTIONS:")
for a in result["recommended_actions"]:
print(f" [ ] {a}")
sa = result["stage_alignment"]
print(f"\nSTAGE ALIGNMENT:")
print(f" ARR: {'Aligned' if sa['arr_aligned'] else 'MISALIGNED'} (expected: {sa['expected_arr_range']})")
print(f" Headcount: {'Aligned' if sa['headcount_aligned'] else 'MISALIGNED'} (expected: {sa['expected_headcount_range']})")
if result["risks"]:
print(f"\nRISKS ({len(result['risks'])}):")
for r in result["risks"]:
print(f" [!] {r}")
print(f"\nREADINESS: {result['readiness_score']}/10 ({result['readiness_label']})")
print()
def main():
parser = argparse.ArgumentParser(description="Assess startup stage and founder growth ceiling")
parser.add_argument("--headcount", type=int, required=True, help="Current headcount")
parser.add_argument("--arr", type=float, required=True, help="Annual recurring revenue in dollars")
parser.add_argument("--stage", required=True, choices=list(STAGES.keys()), help="Funding stage")
parser.add_argument("--has-exec-team", action="store_true", help="Has executive team in place")
parser.add_argument("--has-documented-processes", action="store_true", help="Has documented processes")
parser.add_argument("--founder-meeting-pct", type=int, default=60, help="Percentage of meetings founder attends")
parser.add_argument("--json", action="store_true", help="Output as JSON")
args = parser.parse_args()
result = assess(
args.headcount, args.arr, args.stage,
args.has_exec_team, args.has_documented_processes,
args.founder_meeting_pct
)
if args.json:
print(json.dumps(result, indent=2))
else:
print_human(result)
if __name__ == "__main__":
main()
Related skills
FAQ
What is the founder growth ceiling model?
It maps predictable founder constraints at roughly 15, 50, 150, and 500-plus people, each with a specific problem, solution, and skill to build.
What are the founder archetypes?
Builder, Seller, Operator, and Visionary, each with its own strengths, blind spots, and the co-founder or hire it needs.