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 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 with the salary negotiation prep prompts once you’ve decided which to negotiate hardest.
Best for
- Picking between 2+ competing job offers
- Negotiation prep before the deadline
- Counter-offer evaluation from current employer
- Stay-vs-leave decisions with a single external offer
- Joint decisions with a partner / family
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 clear assumptions about equity value and refresh.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}. Use my risk tolerance: {low/med/high}. Apply a realistic equity-value haircut to B. Show me the risk-adjusted cash-equivalent.3. Growth-trajectory comparison
For each offer, evaluate the 3-year growth trajectory in: scope of ownership, technical ladder progress, network/mentorship, 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, 5 years? 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. Help me draft a 120-word email to the recruiter. Include: gratitude, the competing offer (no exact numbers if better), a specific ask, willingness to commit on acceptance.8. Stay-or-leave (current job vs new offer)
I have a new offer from {B}. Should I stay at current job or leave? Help me list: what current job offers that new one does not, what new offer gives that current does not, and which gaps are addressable by a counter at current.9. Spouse / family input structure
Help me 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, my gut read. Honest and brief.10. Final tiebreaker prompt
I have already done the spreadsheet work and both offers are close. Give me 5 tiebreaker questions to answer honestly: e.g., 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, vesting cliff, refresh policy, 409a, last preferred round, dilution history}. Help me sanity-check the value at low/median/high outcomes. Flag what I should ask before signing.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
- Forgetting reversibility and optionality (which option keeps doors open?)
- Letting an offer deadline force a rushed decision without doing the comparison work
- Using marketing speak from the interview as evidence of the actual day-to-day
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