Prompt

Startup Strategy & FundraisingPromptIn a pack

Delivering Bad News to a Startup Board — Missed Plan, Cash Risk or a Major Setback

Prepares a CEO to tell the board about a missed quarter, a cash crunch, a lost key customer or a co-founder issue — early, plainly and with options — including the pre-call, the written update, choices with trade-offs and what the CEO needs from the board.

  • Role-Based
  • Step-by-Step
  • Constraints
  • Structured Output

Opening lines · ~317 words in full

ROLE: You are an experienced startup CEO coach. Boards forgive bad news delivered early with a plan; they lose trust when they learn it late or dressed up, so you help the CEO say it plainly, take ownership and bring real options.

CONTEXT: The bad news and …

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How to use it

  1. Read it, then replace anything in [BRACKETS] with your details — the more concrete the context, the sharper the answer.
  2. Copy it (or download the .md) and paste it into the AI you already use — it knows your work, so that is where the prompt does the most.
  3. Want a sharper answer? Ask the AI to check its own draft against your brief before it replies — that is self-critique prompting.

Techniques in this prompt

Role-Based

Assigns the model an expert persona so it adopts the right vocabulary, depth, and standards for the task.

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Step-by-Step

Forces explicit intermediate reasoning instead of jumping to a conclusion, which improves accuracy on hard tasks.

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Constraints

Sets the rules and boundaries — tone, length, what to avoid — that keep the output on-target.

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Structured Output

Pins the response to a defined structure so it drops straight into your workflow.

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Works with

Any chat AI — ChatGPT, Claude, Gemini, Copilot, Grok, Mistral or a local model. The structure does the work, so you are not tied to one vendor or one model version.

New to structured prompts? Start with how to prompt AI, the RCTCO prompt framework this prompt is built on, and role prompting examples.

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