C-Level Advisory DecisionsFrameworkLeadership

Executive Mentor — Hard Call

Framework for decisions with no good options.

$skillfish add ~skills/executive-mentor-hard-call

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Real Conversations

See how the Executive Mentor — Hard Call skill responds to actual requests. These are representative examples of what your AI agent will produce.

You

I have two options: lay off 20% of the team (8 people) to extend runway to 24 months and hit default alive, or keep the team and miss the board's 18-month runway requirement. The 8 people I'd cut are all real contributors — no obvious low performers. We're at $2.6M ARR, 40 people, $240K/month burn. What framework do I use for this decision?

Agent

This is a decision with no good options, only better-informed ones. Here's a framework that actually helps.

Step 1: Pressure-test whether these are really the only two options. Common overlooked options:

Salary reductions in exchange for equity (10–20% cuts across leadership can save $30–50K/month without headcount loss)
Revenue-based financing or venture debt ($1–3M at your ARR, adds runway without dilution)
Cutting non-headcount burn (SaaS subscriptions, office, contractors) — typically 10–15% of total burn for a 40-person company
Pricing increase on renewal cohort — a 10% price increase on existing customers is $260K ARR, or $22K/month toward burn reduction

Have you genuinely explored all of these? If yes, proceed to the layoff decision.

Step 2: Clarify what the 8 positions are, not just headcount. "No obvious low performers" is different from "all roles are equally critical to the next 12 months." Map each of the 8 against your key value drivers: are these roles that contribute directly to revenue growth or retention, or are they roles that were right for a larger company vision that needs to be deferred? This isn't about performance — it's about strategic necessity given the revised trajectory.

Step 3: Accept that delay makes it worse. Every month you don't make the call, your runway shrinks, your team senses distress without understanding it, and your ability to do this with care and severance diminishes. Delaying a layoff is not being kind to the 32 you're keeping — it's transferring the risk to them.

On the people: Good execution of a painful layoff means: generous severance (2–3 months for strong contributors), strong references, active help with job placement (warm intros to your network), and honest communication to remaining team within 24 hours. The quality of your execution is the only thing you control here.

You

My co-founder is destroying team morale. Two senior people quit citing him directly. He's 35% equity, no vesting remaining. His continued presence is costing us deals — he contradicts me in customer calls. But confronting him risks him going hostile — blocking board votes, going to investors to undermine me. I'm genuinely scared of the fallout. What's the decision framework?

Agent

This is a conflict between short-term relationship fear and long-term company survival. Here's how to think through it without the fear driving the decision.

First, map the actual risk of the hostile scenario. You have 35% equity, he has 35%. What do your other shareholders look like? If angels and investors hold 30%, a hostile action would require him to convince investors to move against you. Most investors in a healthy Series A company won't override the CEO to back a disruptive co-founder — the asymmetric risk to them is too high. The hostile scenario you're imagining may be less likely than it feels right now.

Second, document before you act. Two senior departures citing him directly — are they documented in exit interviews? Customer call incidents where he contradicted you — do you have email records or CRM notes? Documentation transforms an interpersonal conflict into a business performance record. It also protects you legally.

The decision framework — three paths:

Negotiated separation (best outcome): Direct conversation: "I think we've grown apart in vision and working style. I want to propose a transition where you move to an advisory role." Pair with a buyout proposal at a fair valuation discount (30–40% of current equity value, paid over 18 months). Many co-founders in this position prefer a clean exit to a fight.
Role separation without equity change: Remove him from customer-facing roles and day-to-day operations. Give him a defined scope (specific technical project, no management responsibility). This reduces the blast radius while you prepare for a more formal resolution.
Formal board process: If he refuses all negotiation, you table a board vote on a restructuring of his role. With investors aligned, the vote may not be as close as you fear.

What I'd tell you directly: The fear of the confrontation is larger than the actual confrontation in almost every case I've seen. Leaders who delay these decisions consistently report that the actual conversation was easier than expected and the delay caused more damage than the event.

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

Models & Context

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Recommended Models

Best

Claude Opus 4 Claude Sonnet 4 GPT-4.1 Gemini 2.5 Pro Grok 3 Kimi K2

Good

Claude Haiku 4.5 GPT-4.1 mini Gemini 2.5 Flash Grok 3 mini

Larger models produce more detailed, production-ready outputs.

Context Window

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

8K Skill only

32K+ Skill + conversation

100K+ Skill + references + codebase

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

Pro tips for best results

1

Be specific

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

2

Share constraints

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

3

Iterate

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

4

Combine skills

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

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