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Example

Example: Pre-Mortem for Joining a Startup

How running a pre-mortem before joining a startup revealed critical risks and led to better negotiations.

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The situation

Alex received an offer to be the first marketing hire at a pre-seed startup. The offer was exciting: equity, autonomy, and a chance to build something from scratch.

But Alex was nervous about leaving a stable job. They decided to run a pre-mortem to identify what could go wrong.

Pre-mortem scenario

"It's 6 months from now, and I deeply regret joining this startup. What happened?"

Possible failure modes

  • Company runs out of money: Founders miscalculated runway, and the startup shuts down after 4 months.

  • Role isn't what was promised: Founders said "marketing lead" but really wanted someone to do admin and operations.

  • Founder conflict: Co-founders have unresolved tension, leading to toxic culture and poor decision-making.

  • Market timing is off: Product is ahead of its time; customers aren't ready to buy.

  • Equity is worthless: Cap table is messy with bad terms; even if company succeeds, early employees get diluted to nothing.

  • I miss stability: The chaos and uncertainty of a pre-seed startup are more stressful than I expected.

Mitigation actions

Based on the pre-mortem, Alex took these steps before accepting:

  1. Due diligence on runway: Asked founders directly about burn rate, current ARR, and fundraising plans. Learned they had 10 months of runway and a strong investor pipeline.

  1. Clarified role expectations: Requested a written 90-day plan with specific deliverables to ensure alignment.

  1. Checked founder dynamics: Did reference calls with early employees and advisors. Everyone spoke highly of the founders' collaboration.

  1. Reviewed equity terms: Hired a startup attorney ($500) to review the offer letter and option grant. Negotiated for early exercise rights.

  1. Negotiated severance: Asked for 2 months severance if let go in first year—founders agreed.

The outcome

Alex accepted the offer with much more confidence after mitigating the major risks.

Six months in, the company was thriving. The due diligence and negotiations made Alex feel secure even in the startup's ups and downs.

The pre-mortem process transformed anxiety into actionable risk management.