Military pay is published in a table, applied consistently to everyone at your rank and time in
service, and there is a real fairness in that. It also means that most people leaving the service
have never once had to negotiate a salary.
So this is genuinely new ground, and it is worth learning properly, because the starting number
matters more than it first appears. Every raise, every bonus and every future offer is calculated
off it, so a few thousand dollars at the start compounds into a great deal over a career.
The whole skill comes down to three things: knowing what the market pays, asking once and
specifically, and being gracious either way. All three are learnable in an afternoon, and the
prompts below will walk you through them.
Help me determine what I should be paid for [ROLE] at [COMPANY] in [LOCATION].
My situation:
- Years of relevant experience: [NUMBER — count military experience that genuinely applies]
- Clearance: [LEVEL AND STATUS, OR NONE]
- Certifications: [LIST]
- Education: [DEGREE OR NONE]
- Current or most recent total compensation: [AMOUNT — use the civilian-equivalent figure if
you are coming from military pay]
Give me:
1. The market range for this role and location — 25th, 50th, 75th percentile
2. Where I should realistically position myself in that range, with reasoning
3. The dollar premium for my clearance and certifications specifically
4. How this company is likely to compare to market (above, at, or below) and why
5. Three numbers I should have in my head before any conversation:
- My TARGET (ambitious but defensible)
- My REALISTIC ask (what I will actually say)
- My WALK-AWAY floor (below which I decline)
6. The non-salary levers I could negotiate instead if base is capped: signing bonus, equity, start
date, PTO, remote flexibility, title, education budget, an early review
Cite sources and tell me what to verify on BLS, Levels.fyi, Glassdoor, and state pay transparency
postings.
Do this well before an offer arrives. Knowing your number in advance means that when the call comes you are confirming a decision you already made calmly, rather than making one under time pressure with a figure in front of you.
I received an offer. Help me evaluate the whole package, not just the salary.
THE OFFER:
- Base salary: [AMOUNT]
- Bonus: [TARGET %, GUARANTEED OR DISCRETIONARY]
- Equity: [TYPE, AMOUNT, VESTING SCHEDULE — OR NONE]
- Signing bonus: [AMOUNT OR NONE]
- PTO: [DAYS, AND WHETHER SEPARATE SICK LEAVE]
- Health insurance: [PLAN TYPE, PREMIUM, DEDUCTIBLE, OUT-OF-POCKET MAX]
- Retirement: [401K MATCH TERMS, VESTING]
- Other: [REMOTE POLICY, RELOCATION, EDUCATION BUDGET, ANYTHING ELSE]
- Title and level: [TITLE]
- Start date: [DATE]
MY CONTEXT:
- Current/military total compensation: [AMOUNT]
- VA disability compensation, if any: [AMOUNT AND WHETHER IT CONTINUES]
- Whether I have TRICARE or VA healthcare available: [YES/NO/DETAILS]
- Location and cost of living: [CITY]
Give me:
1. Total first-year compensation, and steady-state annual compensation
2. How it compares to market for this role and location
3. The dollar value of the benefits, especially healthcare given my military options
4. What is strong and what is weak in this package
5. The 3 specific items most likely to be negotiable here, ranked by likelihood of success
6. Any terms I should be concerned about: clawbacks, non-competes, at-will language, a bonus that
is discretionary in practice, an equity grant that is worth less than it appears
7. Questions I should ask before responding
Show your math.
Write my counter-offer message.
The offer: [BASE, BONUS, OTHER TERMS]
What I want: [YOUR ASK — BE SPECIFIC ABOUT THE NUMBER AND ANY OTHER TERMS]
My justification: [MARKET DATA, COMPETING OFFER, CLEARANCE, SPECIFIC SKILLS — WHATEVER IS TRUE]
How I will send it: [EMAIL / PHONE CALL]
How much I want this job: [VERY MUCH / IT IS ONE OF SEVERAL OPTIONS]
The message should:
- Open by clearly accepting the role in principle and expressing genuine enthusiasm
- Make ONE specific ask with a specific number, not a vague "is there flexibility?"
- Justify it with market data and my specific value, not my personal financial needs
- Name a secondary item I would value if the base is truly fixed
- Close warmly and make it easy to say yes
- Be under 200 words
Give me:
1. The email version
2. A phone script version with the key phrases
3. What to say if they come back with a small increase
4. What to say if they say no
5. The one sentence I should NOT say (the common mistake here)
The pattern that works: ask once, ask specifically, and be gracious with the answer. One clear, well-justified request lands well and is often met. Keep the goodwill you have built — it is the thing you will be relying on in your first month.
I want to negotiate but I have no competing offer and no leverage beyond wanting more
money. Help me do this credibly.
The offer: [DETAILS]
Market data I have: [WHAT YOUR RESEARCH SHOWS]
Why I believe I am worth more: [YOUR REASONING]
Give me:
1. The sources of leverage I actually have that I may not be counting — clearance, a scarce skill,
the cost and time of restarting their search, how long the role has been open, my start
availability
2. How to anchor on market data and my value rather than on need
3. Exact language for making an ask when I cannot say "I have another offer"
4. Whether to be honest that this is my only offer if asked directly — and what to say
5. What a realistic outcome looks like here, so I calibrate expectations
6. The point at which continuing to push becomes counterproductive
Do not tell me to bluff about a competing offer. I will not do it and it backfires.
I have [NUMBER] offers and need to decide, and possibly use one to improve another.
OFFER A: [ROLE, COMPANY, FULL PACKAGE, DEADLINE]
OFFER B: [ROLE, COMPANY, FULL PACKAGE, DEADLINE]
[ADDITIONAL OFFERS]
My priorities: [WHAT MATTERS MOST TO YOU — FROM YOUR NON-NEGOTIABLES LIST]
Give me:
1. A side-by-side comparison on total compensation, growth, stability, work itself, and fit
2. A five-year view: which one likely leaves me better positioned, and why
3. How to ethically tell Company A that I have another offer, with exact language — without
naming numbers I should not name or creating an ultimatum
4. How to ask a company for more time when a deadline is pressuring me
5. Which offer has the most negotiating room, and why
6. A decision framework for when the numbers are close and I am stuck
Then ask me the three questions that would most sharpen the decision.
Write me three short messages for this offer from [COMPANY] for [ROLE]:
1. ACCEPTANCE — warm, professional, confirming the agreed terms in writing (base, bonus, start date,
title, and anything negotiated), and asking what happens next. This creates the paper trail.
2. DECLINE — gracious, brief, no burned bridges. [REASON, IF YOU WANT TO GIVE ONE]. I may want to
work with these people later, and the industry is small.
3. REQUEST FOR TIME — asking for [NUMBER] more days without signalling that I am shopping the
offer. Give me a reason that is true and reasonable.
All three under 150 words. Professional but human.
Also tell me: what should I get in writing before I resign or take any irreversible step, and what
is the standard sequence between verbal offer, written offer, background check, and start date?
Wait for a signed written offer, with every contingency cleared — background check, clearance transfer, drug screen — before you resign anything or decline another offer. Verbal offers are given in good faith and things occasionally change; the paperwork is what makes it real.
Explain the terms in this offer letter or employment agreement in plain English. For each
one, tell me what it means in practice, whether it is standard, and whether I should push back.
Pay particular attention to:
- At-will employment language
- Non-compete and non-solicitation clauses, and whether they are enforceable in [STATE]
- Intellectual property assignment, including anything covering work done on my own time
- Arbitration clauses and class action waivers
- Clawback provisions on signing bonuses or relocation
- Equity terms: vesting, cliff, exercise window after leaving, what happens on acquisition
- Bonus language: "target", "discretionary", and what has to be true to actually receive it
- Confidentiality terms
- Anything unusual or aggressive
For each concern, give me the exact language I could propose instead.
IMPORTANT: tell me clearly which items are significant enough that I should have an employment
attorney review them before signing. You are not a lawyer and neither am I.
AGREEMENT:
[PASTE THE TEXT — REMOVE YOUR NAME AND ANY PERSONAL DETAILS FIRST]
For a standard offer letter this level of review is usually enough. For equity-heavy offers, executive roles or anything with a broad non-compete, an hour with an employment attorney is money well spent — a few hundred dollars against a decision worth hundreds of thousands.
