Most candidates compare offers by lining up year-1 cash in a spreadsheet, then go with their gut — and the gut quietly weights whichever number they read most recently. These 12 prompts force the comparison the spreadsheet doesn’t show: risk-adjusted equity math, a 12-month projection of what the work will actually look like (drawn from interview signals, not marketing), a 5-year reversibility test, and the five tiebreaker questions that surface what you actually want. Pair them with the salary negotiation prep prompts once you’ve decided which offer to negotiate hardest.
TL;DR
- Replace every
[bracketed placeholder]with your real numbers and signals before sending the prompt — vague inputs give vague comparisons. - Always discount startup equity. Common-stock 409A value sits well below the preferred-round price, and most option grants end up worth little, so compare a risk-adjusted cash equivalent, never face value.
- A competing offer is real leverage: about 42% of candidates counter, and roughly 85% of those who do get at least part of what they ask for (Scale.jobs 2025 analysis).
- For the math (year-by-year vesting, expected value), use a model that can run code; for the judgment calls (long interview notes, manager fit), use one with a large context window.
Which AI to use for offer comparison
| Task | Best pick (as of June 2026) | Why |
|---|---|---|
| Year-by-year cash + equity tables | ChatGPT Plus ($20) with the data-analysis tool | Writes and runs real Python on your numbers, so the totals are reproducible, not guessed |
| Reasoning over long interview notes | Claude Pro ($20, Opus 4.7 / Sonnet 4.6, 1M-token context) | Reads all your notes in one pass and stays measured rather than overconfident |
| Quick second opinion, free | ChatGPT Free (GPT-5.5) or Claude Free (Sonnet 4.6) | Fine for the qualitative prompts; tight limits make them weaker for repeated number-crunching |
Paste your offer letters and interview notes, not a summary — the more raw input the model sees, the less it fills gaps with assumptions. For the equity prompts specifically, ask the model to show its formula, then sanity-check the arithmetic yourself. See our ChatGPT data-analysis workflow for setting that up, and ChatGPT vs Claude vs Gemini if you’re picking one tool.
1. Total-compensation breakdown
Compare these 2 offers on total compensation. Inputs: [paste offer A — base, bonus, equity terms, vesting, sign-on, refresh policy] and [paste offer B]. Output a year-1, year-2, year-4 cash-equivalent table, with the equity-value and refresh assumptions stated explicitly. Show your math.2. Risk-adjusted offer math
Adjust the offer comp for risk. Offer A: [public company, RSU]. Offer B: [Series B startup, ISO/NSO with 4-year vest]. My risk tolerance: [low/med/high]. Apply a realistic equity-value haircut to B (common-stock 409A value, not the preferred-round price, then discount for dilution and the odds the grant pays off). Show me the risk-adjusted cash-equivalent and the haircut you used.3. Growth-trajectory comparison
For each offer, evaluate the 3-year growth trajectory on: scope of ownership, technical-ladder progress, network/mentorship, and optionality after I leave. Weighted score against my priorities: [priorities].4. Lifestyle and burnout audit
Based on what I learned from each company's interviews: [paste signals]. Score lifestyle on: hours/week, on-call, predictability, commute, vacation reality, manager style. Flag the one signal I should investigate before deciding.5. “Why this job in 12 months” projection
For each offer, write a 100-word projection of what my work will look like 12 months in: what I will own, who I will work with, what skill I will gain. Use only what I learned from interviews, not marketing. Be specific.6. The 5-year reversibility test
Reversibility test: if I take offer [A], how easy is it to switch to offer [B]'s career path in 1, 3, and 5 years? Now vice versa. Highlight which choice is more reversible and why.7. Counter-offer drafting
I want to counter offer [A] using offer [B] as leverage. Draft a 120-word email to the recruiter. Include: gratitude, the competing offer (no exact numbers if mine is higher), a specific ask, and willingness to commit on acceptance. Keep the tone warm, not transactional.8. Stay-or-leave (current job vs new offer)
I have a new offer from [B]. Should I stay at my current job or leave? List: what the current job offers that the new one does not, what the new offer gives that the current does not, and which gaps a counter at my current employer could close.9. Spouse / family input structure
Write a 1-page summary I can share with my partner to make the offer decision jointly. Sections: cash impact, time impact, location impact, career impact, risk profile, and my gut read. Honest and brief.10. Final tiebreaker prompt
I've already done the spreadsheet work and both offers are close. Give me 5 tiebreaker questions to answer honestly — for example: which manager would I learn more from, which job would I be more excited about on Monday morning, which would I regret turning down.11. Equity-evaluation deep-dive
Offer [B]'s equity grant: [paste terms — strike price, vesting cliff, refresh policy, latest 409A, last preferred round, dilution history]. Sanity-check the value at low/median/high outcomes. Flag what I should ask before signing (option-exercise window after I leave, single-trigger vs double-trigger acceleration, secondary-sale rights).12. Negotiation-room finder
Given offers [A] and [B], where is the most likely negotiation room for each? Levers to consider: base, sign-on, equity, refresh policy, start date, level/title, remote flexibility. Suggest 2 asks for each that are likely to move.Common mistakes
- Comparing on year-1 cash only and discovering the cliff in month 13.
- Ignoring future dilution and refresh policy on equity grants.
- No risk-adjustment for startup equity — comparing RSU to ISO at face value instead of risk-adjusted cash.
- Forgetting reversibility and optionality (which option keeps the most doors open?).
- Letting an offer deadline force a rushed decision before you’ve done the comparison work.
- Treating interview marketing speak as evidence of the actual day-to-day.
FAQ
How big a haircut should I apply to startup equity? There’s no fixed number, but two adjustments matter most. First, value the grant on the common-stock 409A price, not the headline preferred-round valuation — the 409A is typically a fraction of it because common shares lack the preferences investors hold. Second, discount for dilution in future rounds and for the real odds the grant pays off. The honest framing is a range (low/median/high outcome), not a single confident dollar figure.
Is a competing offer actually useful leverage? Yes, when it’s genuine. Around 70% of hiring managers expect candidates to negotiate, yet a majority accept the first offer. Of the ~42% who counter, about 85% get at least some of what they ask for (Scale.jobs, 2025). The common guidance in 2026 is to counter 10–20% above the initial number with market evidence, and 15–25% for in-demand technical roles with a real competing offer in hand.
Should I paste my full offer letters into an AI tool? Treat the letters as confidential. Redact names, identifiers, and anything an NDA covers, and prefer a paid account (ChatGPT Plus $20 or Claude Pro $20 as of June 2026) where you can turn off training on your chats in settings. The math prompts work fine on anonymized numbers.
ChatGPT or Claude for this? For the number-heavy prompts (1, 2, 11), ChatGPT’s data-analysis tool runs actual Python so the totals are reproducible. For the judgment prompts that chew through long interview notes (4, 5, 10), Claude Opus 4.7 / Sonnet 4.6 with a 1M-token context handles the volume and stays measured. Many people use both and compare the two answers.
Can AI just tell me which offer to take? No — and you shouldn’t outsource the decision. These prompts surface trade-offs you’d otherwise skip: the equity haircut, the reversibility cost, the Monday-morning gut check. The choice stays yours. For deeper reading on equity terms, see Holloway’s Guide to Equity Compensation.
Related
- Salary negotiation prompts
- Mock interview prompts
- Interview debrief prompts
- Recruiter reply prompts
- JD matching prompts
- Salary negotiation prep prompts before the offer lands
Tags: #Prompt #Job search #Salary