C-Level Advisory Pre-mortemAnalysisChallenge

Executive Mentor — Challenge

Pre-mortem plan analysis to find weaknesses before they find you.

$skillfish add ~skills/executive-mentor-challenge

Real Examples Get Started Models & Context

Real Conversations

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

You

I'm about to present a plan to the board: $2.1M ARR today, target $6M ARR in 18 months — a 3x from here. The plan requires: doubling the sales team (3→6 AEs), $400K marketing investment, and launching a new enterprise tier. Find the holes in this plan before I present it.

Agent

I'll pressure-test this the way a skeptical board member will. Here are the five holes.

Hole 1 — The headcount assumption: Doubling AEs from 3→6 assumes new AEs ramp in 90 days and hit full quota in 6 months. Industry data says SaaS AE ramp is 9–12 months. If you hire in month 2, you get 6–9 months of productive quota from them. On a 3x growth plan, timing of ramp matters enormously. Have you modeled monthly ARR contribution from each AE with realistic ramp, or just used annualized quota?

Hole 2 — The marketing ROI assumption: $400K in marketing generating what MQLs? At what close rate? If your current blended CAC is $8K and you're closing 1 deal per $8K, $400K = 50 new customers. If average ACV is $14K, that's $700K ARR from the marketing investment. That gets you to $2.8M, not $6M. Where does the other $3.2M come from?

Hole 3 — The enterprise tier: New pricing tier assumes enterprise customers exist in pipeline, have been validated, and your product is ready. What's the evidence? Have you signed even 2–3 enterprise customers at the proposed price point? Enterprise launches without pipeline validation are commonly 6+ months behind schedule.

Hole 4 — The retention assumption: To go from $2.1M to $6M in 18 months, you need net new ARR AND low churn. What NRR assumption is baked in? At 85% NRR, you're fighting an erosion that requires $3.15M in gross new ARR just to net $2M. At 110% NRR, your expansion revenue is a tailwind. Your plan needs an explicit NRR assumption.

Hole 5 — Dependencies between workstreams: Enterprise tier requires product work, which requires engineering, which is competing with your current roadmap. Marketing investment requires pipeline management capacity, which requires AEs to be ramped, which takes time. Have you mapped the critical path and identified where a single delay creates a cascade?

You

I want to hire 12 people in the next 6 months to accelerate growth. We're at $3.4M ARR, burning $220K/month with 13 months runway. The 12 hires would cost $180K/month incremental, bringing burn to $400K/month. At that burn, we have 7 months of runway. My assumption: these hires will generate enough ARR growth to raise Series B before we hit 6 months runway. Find the flaw.

Agent

This plan has a structural flaw that could sink the company. I want to be direct.

The flawed assumption: hire 12 people → generate ARR growth → raise Series B at 6 months runway. Here's why this is dangerous logic.

Flaw 1 — Ramp time destroys the math. You're hiring people in month 1, but revenue impact happens in months 4–9 at best (depending on role). If 6 of these are AEs, they won't hit quota until month 9–12. If they're engineers shipping product, code shipped in month 3 generates revenue in month 6 at earliest. You spend $180K/month immediately; you earn the return 4–6 months later. This means you may be raising Series B before you can demonstrate the revenue lift the hires were supposed to create.

Flaw 2 — You're running the fundraise from a position of maximum distress. 6 months runway is the threshold where Series B investors begin discounting your leverage. At 4 months runway, you're a distressed seller. Your timeline assumes the raise closes in month 7. Series B rounds take 3–5 months end-to-end. You need to start the process in month 2–3, before the hires have shown impact. You'll be pitching growth that isn't in the numbers yet.

Flaw 3 — The scenario analysis is missing. What happens if Series B takes 6 months instead of 3? Or if 3 of the 12 hires don't work out and must be replaced (2–3 month delay per replacement)? In both cases, the plan ends in an emergency bridge or down round.

A safer structure: Hire 6 now (the highest-ROI roles), target Series B process starting in month 4, and leave the second 6 hires contingent on the raise closing. You extend runway from 7 months to 10, which dramatically improves fundraise leverage.

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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

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Pro tips for best results

1

Be specific

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

2

Share constraints

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3

Iterate

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

4

Combine skills

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