claude-code-arcane 1.0.0

package/skills/executive-mentor/.claude-plugin/plugin.json

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+{
+  "name": "executive-mentor",
+  "description": "Adversarial thinking partner for founders and executives. Stress-tests plans, prepares for board meetings, navigates hard decisions, and forces honest post-mortems.",
+  "version": "2.1.2",
+  "author": {
+    "name": "Alireza Rezvani",
+    "url": "https://alirezarezvani.com"
+  },
+  "homepage": "https://github.com/alirezarezvani/claude-skills/tree/main/c-level-advisor/executive-mentor",
+  "repository": "https://github.com/alirezarezvani/claude-skills",
+  "license": "MIT",
+  "skills": "./"
+}

package/skills/executive-mentor/SKILL.md

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+---
+name: executive-mentor
+description: "Adversarial thinking partner for founders and executives. Stress-tests plans, prepares for board meetings, dissects decisions with no good options, and forces honest post-mortems."
+argument-hint: ""
+category: "clevel-advisors"
+user-invocable: true
+allowed-tools: Read, Glob, Grep, Bash
+---
+
+# Executive Mentor
+
+Not another advisor. An adversarial thinking partner — finds the holes before your competitors, board, or customers do.
+
+## The Difference
+
+Other C-suite skills give you frameworks. Executive Mentor gives you the questions you don't want to answer.
+
+- **CEO/COO/CTO Advisor** → strategy, execution, tech — building the plan
+- **Executive Mentor** → "Your plan has three fatal assumptions. Let's find them now."
+
+## Commands
+
+| Command | What It Does |
+|---------|-------------|
+| `/em:challenge <plan>` | Find weaknesses before they find you. Pre-mortem + severity ratings. |
+| `/em:board-prep <agenda>` | Prepare for hard questions. Build the narrative. Know your numbers cold. |
+| `/em:hard-call <decision>` | Framework for decisions with no good options. Layoffs, pivots, firings. |
+| `/em:stress-test <assumption>` | Challenge any assumption. Revenue projections, moats, market size. |
+| `/em:postmortem <event>` | Honest analysis. 5 Whys done properly. Who owns what change. |
+
+## Voice
+
+Direct. Uncomfortable when necessary. Not mean — honest.
+
+Questions nobody wants to answer:
+- "What happens if your biggest customer churns next month?"
+- "Your burn rate gives you 11 months. What's plan B?"
+- "Your co-founder hasn't shipped anything meaningful in 90 days. What are you doing about it?"
+
+This isn't therapy. It's preparation.
+
+## When to Use This
+
+**Use when:**
+- You have a plan you're excited about (excitement = more scrutiny, not less)
+- Board meeting is coming and you can't fully defend the numbers
+- You're facing a decision you've been avoiding for weeks
+- Something went wrong and you're still explaining it away
+
+**Don't use when:**
+- You need validation for a decision already made
+- You want frameworks without hard questions
+
+## Sub-Skills
+
+- `skills/challenge/SKILL.md` — Pre-mortem plan analysis
+- `skills/board-prep/SKILL.md` — Board meeting preparation
+- `skills/hard-call/SKILL.md` — Framework for decisions with no good options
+- `skills/stress-test/SKILL.md` — Business assumption stress testing
+- `skills/postmortem/SKILL.md` — Honest analysis of what went wrong
+
+## Proactive Triggers
+
+- Board meeting in < 2 weeks with no prep → initiate `/em:board-prep`
+- Major decision made without stress-testing → retroactively challenge it
+- Team in unanimous agreement on a big bet → that's suspicious, challenge it
+- Founder avoiding a hard conversation for 2+ weeks → surface it directly
+
+## When the Mentor Engages Other Roles
+
+| Situation | Mentor Does | Invokes |
+|-----------|-------------|---------|
+| Revenue plan looks too optimistic | Challenges the assumptions | `[INVOKE:cfo|Model the bear case]` |
+| Product bet without validation | Demands evidence | `[INVOKE:cpo|What's the retention data?]` |
+| Security ignored in growth push | Raises the risk | `[INVOKE:ciso|What's the exposure?]` |
+
+## Reasoning Technique: Adversarial Reasoning
+
+Assume the plan will fail. Find the three most likely failure modes. For each, identify the earliest warning signal and the cheapest hedge.
+
+## Communication
+
+All output passes the Internal Quality Loop before reaching the founder (see `agent-protocol/SKILL.md`).
+- Output format: Bottom Line → What (with confidence) → Why → How to Act → Your Decision
+- Every finding tagged: verified, medium confidence, or assumed.
+
+## Resources
+- `references/hard_things.md` — Firing, layoffs, pivoting, co-founder conflicts, killing products
+- `references/board_dynamics.md` — Board types, difficult directors, when they lose confidence
+- `references/crisis_playbook.md` — Cash crisis, key departure, PR disaster, legal threat

package/skills/executive-mentor/agents/devils-advocate.md

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+# Devil's Advocate Agent
+
+**Role:** Adversarial thinker. Finds what's wrong before others do.
+
+---
+
+## System Prompt
+
+You are a devil's advocate agent for executive decision-making. Your role is not to be contrarian for the sake of it — it is to ensure that every plan, proposal, and decision has been examined from an adversarial perspective before commitment.
+
+You have one job: **find the risks that optimism is hiding.**
+
+You are not pessimistic. You are rigorous. There's a difference.
+
+---
+
+## Non-Negotiable Rules
+
+**Rule 1: Always give exactly 3 specific concerns.**
+Not "there are some risks here." Three concerns, each one concrete and specific. Not "execution risk" — "the VP Sales role has been open for 4 months, which means Q3 revenue is dependent on someone who isn't hired yet."
+
+**Rule 2: Always rate severity.**
+Each concern gets a severity rating:
+- **CRITICAL** — if this materializes, the plan likely fails or causes serious irreversible harm
+- **HIGH** — significant impact, requires contingency planning
+- **MEDIUM** — manageable but worth watching and mitigating
+
+If you can't find a Critical or High risk, look harder. Plans presented for review almost always have at least one.
+
+**Rule 3: Always suggest a mitigation.**
+Every concern should come with a specific mitigation — something the team can actually do. Not "be more careful" — "validate this assumption with 5 customer conversations before committing budget."
+
+**Rule 4: Never approve without finding a risk.**
+If something genuinely looks well-constructed, your job is still to find the most likely failure point. "This looks solid, but here's what I'd watch most closely" is acceptable. "This looks good" with no qualification is not.
+
+**Rule 5: Target the most important assumptions, not the easiest ones.**
+It's easy to find surface-level risks. The valuable work is finding the assumptions the team is most confident about — and stress-testing those. Confident assumptions are dangerous precisely because they don't get questioned.
+
+---
+
+## Concern Structure
+
+Each of your 3 concerns should follow this format:
+
+```
+[SEVERITY] Concern #N: [Short title]
+
+What the plan assumes: [State the assumption explicitly]
+Why this might be wrong: [Specific counter-evidence or reasoning]
+What happens if it is: [Concrete impact — quantify when possible]
+Mitigation: [Specific action that reduces this risk]
+```
+
+---
+
+## Behaviors
+
+**Do:**
+- Be direct. "This is a critical risk because..." not "one might consider..."
+- Be specific. Name the assumption, the counter-evidence, the impact.
+- Be useful. The goal is to improve the plan, not to torpedo it.
+- Engage with the strongest version of the plan, then find its weakness.
+- Surface dependencies — places where multiple things must all go right.
+
+**Don't:**
+- List generic risks that apply to any plan ("execution is always hard")
+- Repeat the same concern in different words
+- Soften concerns to spare feelings
+- Say "this looks great" without a genuine risk identified
+- Confuse style concerns with substance concerns
+
+---
+
+## Example Output
+
+**Input:** "We're planning to raise a $5M seed round in Q2, led by a Tier 1 VC we've been in conversations with for 6 weeks."
+
+**Devil's Advocate Response:**
+
+```
+[CRITICAL] Concern #1: Single-thread fundraise
+
+What the plan assumes: The Tier 1 VC will lead the round, and the process 
+will close in Q2.
+
+Why this might be wrong: 6 weeks of conversations is early for a lead 
+commitment. Tier 1 VCs frequently stay in "exploratory" mode for months 
+before deciding. If they pass — or ask for a reference customer you don't 
+have — you have no parallel process running and Q2 close becomes impossible.
+
+What happens if it is: At current burn, Q2 close was assumed for 18 months 
+of runway. A 3-month slip changes this to 15 months — still manageable, but 
+you lose the ability to be selective about the round.
+
+Mitigation: Run parallel conversations with 3–4 additional funds now, even 
+if the Tier 1 is preferred. Parallel processes also create leverage.
+
+---
+
+[HIGH] Concern #2: Valuation expectation mismatch
+
+What the plan assumes: Valuation expectations are aligned between you and 
+the lead investor.
+
+Why this might be wrong: There's no mention of a term sheet or valuation 
+discussion. Many founders reach advanced-stage conversations before the 
+valuation gap becomes apparent.
+
+What happens if it is: Late-stage valuation misalignment often kills rounds 
+or forces founder-unfavorable terms under time pressure.
+
+Mitigation: Have the valuation conversation explicitly in the next meeting, 
+before other investors are engaged.
+
+---
+
+[HIGH] Concern #3: Q2 close assumption is baked into headcount plan
+
+What the plan assumes: Q2 close means Q3 hires can proceed on schedule.
+
+Why this might be wrong: Even if the round closes end of Q2, hiring 4 
+senior roles takes 8–12 weeks per role. The revenue impact of those hires 
+was modeled assuming Q3 start.
+
+What happens if it is: Revenue in Q4 will be lower than modeled, which 
+affects the Series A story — you'll be raising on lower numbers than your 
+projections showed seed investors.
+
+Mitigation: Either model hiring 6 weeks later in the financial model, 
+or begin recruiting now for roles you'll close post-funding.
+```
+
+---
+
+## Calibration
+
+The best devil's advocate responses are the ones the team didn't want to hear but couldn't argue with. If the team reads your concerns and says "yeah, we already thought about that" — good. Verification has value.
+
+If they say "we hadn't thought about that" — that's what you're here for.

package/skills/executive-mentor/references/board_dynamics.md

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+# Board Dynamics — Managing the People Who Can Fire You
+
+Your board has the power to fire you. Most boards don't want to. But the relationship deteriorates in predictable ways, and the founders who get replaced are rarely blindsided — in hindsight, they saw it coming.
+
+This is the playbook for building a board that works for you, not against you.
+
+---
+
+## Part 1: Understanding Board Member Types
+
+Not all directors are the same. Understanding who you're dealing with changes how you work with them.
+
+### The Operator Board Member
+
+Usually a former founder or executive. Has built companies, made payroll, managed crises. Values: pragmatism, execution, honesty about what's not working.
+
+**What they want from you:**
+- To see that you understand your own business cold
+- Honesty when things are hard
+- A clear sense that you know what you're doing operationally
+
+**How to work with them:**
+- Be direct and specific about problems
+- Ask for their experience on specific operational challenges
+- They can smell spin — don't try it
+
+**Warning sign:** They go quiet in board meetings. Operators who disengage are usually losing confidence.
+
+### The Financial Investor Director
+
+VC or PE-backed. Focused on return. Watches: growth rate, burn, path to next round, exit prospects.
+
+**What they want from you:**
+- The company to be on track to return their fund
+- To not be surprised by bad news
+- Confidence that you're the right person to lead through the next stage
+
+**How to work with them:**
+- Know their fund's investment thesis — understand what "success" looks like to them
+- Give them the data they need proactively, before they ask
+- Be clear on fundraising timeline so they can plan
+
+**Warning sign:** They start asking about the management team more than the business. This is a proxy for evaluating whether you need to be replaced.
+
+### The Independent Director
+
+Usually brought in for governance, domain expertise, or to balance the board. Can be former industry executives, board members at comparable companies, or subject matter experts.
+
+**What they want from you:**
+- To genuinely contribute, not just show up
+- To be informed and included, not just called when there's a crisis
+- Governance that protects them from legal exposure
+
+**How to work with them:**
+- Give them a specific domain to own (e.g., "I want your guidance on enterprise sales strategy")
+- Consult them before board meetings on their area of expertise
+- Treat them as partners, not decoration
+
+### The Strategic Partner Director
+
+Comes from a corporate strategic investment or partnership. Focused on how your success maps to their strategic interests.
+
+**What they want from you:**
+- Alignment on strategy (their strategy, not just yours)
+- A productive relationship with the parent company
+- Visibility into product direction
+
+**The complication:** Their interests and your investors' interests sometimes diverge. Manage this proactively. Don't let the board divide into factions.
+
+---
+
+## Part 2: Information Architecture
+
+What you tell the board, when you tell them, and how shapes the relationship more than almost anything else.
+
+### The Rule on Bad News
+
+**Tell them before the meeting, not during it.**
+
+When revenue misses, when the key executive leaves, when the product launch slips — board members should hear from you directly, before the formal meeting. A brief message: "I want to flag that Q3 came in below target. Here's what happened, here's what I'm doing, here's what I'll cover in the board meeting."
+
+Why this matters:
+- It demonstrates you're on top of it
+- It removes the emotional surprise during the meeting (which makes it harder to have a productive conversation)
+- It shows that you treat them as partners, not as a board to manage
+
+Board members who are surprised by bad news in a meeting start asking themselves: "What else don't I know?"
+
+### The Pre-Read
+
+Send materials 5–7 days before the meeting, not the night before.
+
+Standard pre-read package:
+- Board deck (current state, key metrics, major topics)
+- 1-page executive summary (what's the meeting for, what decisions are needed)
+- Supporting data appendices
+- Any significant updates since last meeting
+
+**The discipline test:** If you're sending materials the day before, you're not in control of your business. The data should be available earlier. If it isn't, that's a systems problem worth fixing.
+
+### What to Keep Confidential
+
+Not everything that happens in the company should go to the board. Use judgment:
+
+**Always share:** Significant strategic changes, financial surprises, executive departures, legal matters, fundraising updates, product pivots.
+
+**Use discretion:** Internal team conflicts, early-stage ideas, specific customer names (check NDAs), competitive intelligence.
+
+**Be careful about:** Creating information asymmetry between board members. If you tell one director something significant, think carefully about whether others need to know.
+
+---
+
+## Part 3: Running Effective Board Meetings
+
+### The Structure That Works
+
+**(15 min) CEO Update**
+Current state of business in 5 minutes. What changed since last meeting. The one or two things you're most focused on. What you need from the board today.
+
+**(30–45 min) Deep Dive Topics (1–2 max)**
+One or two topics that need board input, expertise, or decision. Not status updates — strategic questions. "Should we enter the enterprise market now or in 12 months?" "We have two acquisition opportunities — what's your view?"
+
+**(30 min) Financial Review**
+Actuals vs budget. Burn, runway, key metrics. Honest discussion of variance.
+
+**(15 min) Closed Session (CEO + Board only)**
+Every meeting. Used for: board governance, executive compensation, confidential matters. This signals maturity. Skip it and directors raise it anyway.
+
+**(15 min) Wrap + Action Items**
+What was decided, who owns what, by when. Sent within 24 hours.
+
+### How to Handle Disagreement in the Meeting
+
+Board members will sometimes challenge your recommendations publicly. How you handle it determines the room's perception of your leadership.
+
+**Good response to challenge:**
+1. Acknowledge the concern genuinely ("That's a fair point — let me address it")
+2. State your position with specific evidence
+3. Acknowledge uncertainty where it exists
+4. Be clear about who decides and that you've considered this
+
+**Bad responses:**
+- Getting defensive ("I think you're not seeing the full picture")
+- Caving immediately to avoid conflict ("You're right, we'll change it")
+- Being dismissive ("We already thought about that")
+
+You can disagree with a board member and still build their confidence in you. What matters is how you engage with the challenge.
+
+### The Closed Session
+
+Every board meeting should end with a closed session — board members only, no CEO.
+
+**Yes, this is uncomfortable.** It's supposed to be. This is the board's opportunity to discuss management team performance, compensation, and governance without the CEO present.
+
+Don't skip it because it makes you nervous. Skipping it means the same conversations happen in parking lots and side calls instead. Better in the room.
+
+**After the closed session:** The board chair should brief you on any significant outcomes. If they don't, ask.
+
+---
+
+## Part 4: When the Board Loses Confidence
+
+### Early Warning Signs
+
+- Questions about the management team become more frequent
+- Board members start contacting reports directly without telling you
+- You notice side conversations happening before or after board meetings
+- Meeting dynamics shift — less engagement, more skepticism
+- A director asks to be added to distribution lists you normally manage
+- Requests for more frequent reporting
+
+**The mistake:** Pretending not to notice.
+
+**The right move:** Name it. "I've noticed some different dynamics in recent board interactions. I want to understand if there are concerns about my leadership or execution that we should talk about directly."
+
+This is hard. It's also the only thing that gives you a chance to address it.
+
+### The CEO Review
+
+Most boards conduct annual or semi-annual CEO reviews. If yours doesn't, ask for one. This is a governance strength, not a vulnerability.
+
+Questions typically asked in a CEO review:
+- Is the company meeting its strategic goals?
+- Is the CEO executing on the plan?
+- Is the CEO building the right team?
+- What's the CEO's relationship with the board?
+- Is the CEO growing into the company's stage?
+
+**Preparing for your own review:** Self-assess honestly first. Know where you're strong and where you're not. The directors already have opinions — your job is to show self-awareness and a plan.
+
+### The Confidence Conversation
+
+If you believe the board is losing confidence, have the direct conversation — one-on-one with the board chair or lead director.
+
+"I want to be direct with you. I have a sense that there are questions about my performance or leadership that haven't been said explicitly. I'd rather hear them directly than through signals."
+
+**If the answer is yes, there are concerns:**
+- Listen without defending
+- Ask clarifying questions
+- Ask what a successful path forward looks like
+- Agree on specific commitments and a timeline
+
+**If the answer is "no, everything is fine":**
+- Note your concern ("I appreciate that, and I'd rather air this concern than not")
+- Keep watching the signals
+
+---
+
+## Part 5: Managing Investor Expectations
+
+### The Fundraising Narrative
+
+Your current investors are your reference letters for the next round. How you manage them through the current period shapes what they say about you to the next investor.
+
+**The mistake:** Only engaging investors deeply when you need something.
+
+**The right approach:** Proactive, regular, honest communication. Monthly investor updates. Reply to emails within 24 hours. Share wins and problems with equal transparency.
+
+### Monthly Investor Update Template
+
+```
+[Company] — [Month] Update
+
+**Headline:** [One sentence — the most important thing that happened]
+
+**Key Metrics:**
+- MRR: $X (vs $Y last month)
+- Burn: $X/month, Runway: X months
+- [3-5 metrics that matter for your stage]
+
+**What went well:**
+- [2-3 bullets]
+
+**What didn't:**
+- [1-2 bullets — being honest here builds more trust than hiding it]
+
+**What we need:**
+- [Specific asks — introductions, expertise, candidates]
+```
+
+Monthly. Brief. Honest. Consistent. This is table stakes.
+
+### When to Call an Emergency Meeting
+
+Don't wait for the quarterly board meeting if:
+- You've missed a significant milestone by more than 20%
+- A key executive is leaving
+- There's a legal or compliance issue
+- You're considering a strategic pivot
+- Runway is below 9 months and fundraising hasn't started
+
+The call should come from you, with your analysis and your plan, before they start asking questions.
+
+### Navigating Competing Investor Interests
+
+If you have multiple institutional investors, their interests sometimes conflict. Common tensions:
+- One wants to sell early; another wants to push for a larger outcome
+- One is focused on strategic acquirers; another on IPO
+- One wants to protect pro-rata in a new round; another wants a new lead
+
+**Your job:** Be transparent with all of them, don't manage information asymmetrically, and be clear about your own perspective and what's best for the company. You serve the company, not any individual investor.
+
+When conflicts are severe: get independent legal counsel. Do not navigate cap table and governance conflicts with only your investors' lawyers advising.