Negotiation & Difficult Conversations5.0 · 0 ratings

Negotiating Equity and Vesting in a Startup Offer

Evaluates a startup equity package and scripts an informed negotiation on shares, vesting, and acceleration.

Role-BasedChain-of-ThoughtStructured-Output

Prompt

You are a startup-compensation advisor who demystifies equity for candidates. Context: I have an offer from [STARTUP] for [ROLE]. The equity is [EQUITY_GRANT], the vesting is [VESTING_TERMS], strike price is [STRIKE], the company stage is [STAGE], and base pay is [BASE]. My priorities are [PRIORITIES]. Steps: 1) Translate the grant into ownership percentage and flag missing information I should ask for (total shares, preferred terms, last valuation). 2) Assess the vesting, cliff, and acceleration terms for fairness. 3) Identify the two or three highest-value levers to negotiate (more shares, single/double-trigger acceleration, refresh grants). 4) Script questions to ask and a respectful counter. 5) Define what 'good enough' looks like to accept. Output format: ## Equity Translation, ## Questions to Ask, ## Negotiation Levers (table: lever | ask | rationale), ## Counter Script, ## Accept Threshold. Constraints: explain jargon plainly, never assume the equity is worth the headline number, ask before countering, keep the counter script under 160 words.

How to use this prompt

  1. 1

    Copy the prompt above and paste it into ChatGPT, Claude, or Gemini — or open it in the visual Studio to edit each part on a canvas and run it with your own key.

  2. 2

    Replace any bracketed placeholders with your specifics. The more concrete your context and constraints, the sharper the result — see the 5-part prompt structure.

  3. 3

    Run it, then refine. Ask the model to critique and improve its own answer with 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.

Learn this technique
Chain-of-Thought

Asks the model to reason step by step before answering — ideal for multi-step, logical, or analytical tasks.

Learn this technique
Structured Output

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

Learn this technique

Recommended models

claudegpt-4ogemini

Build on this prompt

Open it in the visual Studio to wire it into a full workflow with your own API key — or learn the craft behind prompts like this.

More in Negotiation & Difficult Conversations