Money conversations are the conversations almost no one is good at, almost no one practises, and almost everyone wings. Asking for a raise. Pushing back on a customer who wants a discount you cannot give. Raising prices on a client you have served at the lower number for three years. Asking the board for the budget that lets your team actually ship. Closing the offer letter without leaving twenty percent on the table because you were too uncomfortable to counter. Pricing your own services for the first time and naming a number that is half what the market would pay.
Every one of these moments compounds. Underprice yourself in year one and the next decade of comp is anchored to a number that was wrong from the start. Accept the first offer the customer puts on the table and the relationship's entire commercial logic is locked in at their first move. Concede a percentage point in vendor negotiation and the compounding cost is real. The math is brutal and the social pressure to avoid the math is worse.
This is where structured AI rehearsal earns its keep more clearly than almost anywhere else. Not as a calculator (you can do the math). Not as a script generator (the words are easy once the thinking is right). The real leverage is in the thinking that has to happen before you walk in: what is actually defensible, what is the other side's real ceiling, what is your honest walk away, what is the move that flips the asymmetry. Those are the moments where AI is the cheapest second opinion you will ever access, and the only one available at 11pm before a 9am conversation that will affect your earnings for the next five years.
The MONEY Framework is fifty prompts for those moments. Five pillars across the full arc of any money conversation: mapping what is defensible, opening the conversation, navigating the back and forth, escalating when stuck, and yielding well (accept, walk, or hold). Use them for salary, pricing, raises, budget asks, fundraising, and any other context where the dollar number is on the table.
This guide is LLM agnostic. The prompts work in ChatGPT, Claude, Gemini, and any approved enterprise model. Anonymise sensitive financial information where required. Specificity in your inputs is the difference between generic negotiation advice and a real plan for your specific situation.
What is the MONEY Framework
A method for using AI as a structured thinking partner across the five categories of work that determine whether a money conversation lands in your favour. Each pillar maps to one phase of the negotiation arc.
- M: Map. Establish the financial landscape. Triangulate comparables, decompose the package, calculate your honest walk away, model the time value and the hidden costs.
- O: Open. Broach the conversation. Set the frame. Time it right. Draft openers that anchor without anchoring against yourself.
- N: Navigate. Run the back and forth. Counter, concede strategically, decode silences, reframe when stuck, use lateral moves when the cash number is fixed.
- E: Escalate. Recognise when the current channel is exhausted. Bring in the alternative offer, the third party reference, the strategic frame, the coalition. Know when to push and when to pause.
- Y: Yield. Close the conversation well. Accept, walk, or hold. Each requires a different mechanic and a different message. Sign without regret or decline without burning the bridge.
Five pillars. The MONEY Framework runs in rough sequence but loops in practice. Many real money conversations spend most of their time in Navigate. The harder ones land in Escalate. The good ones end in a Yield that everyone can live with for years.
How to use this guide
Three principles before you run any of the prompts below.
First, the money conversation is information asymmetric and the other side has done more of these than you have. They have a comp band they cannot exceed, a discount floor they cannot go below, a valuation range their LPs will tolerate. Your job is to figure out where their real numbers sit before you commit to your move. AI is the cheapest research partner available. Use it deliberately, not just for drafting words.
Second, the model can only help with what you give it. Paste the actual offer terms, the actual customer's purchase history, the actual cap table assumptions, the actual board's recent stated priorities. Generic input produces generic preparation. The specificity is the value.
Third, the writing the model produces is a draft, not a deliverable. Anything that goes to the counterparty in your name (counter offer email, raise request, pricing notice) must be rewritten by you in your own voice. Money conversations are partly tests of confidence and pure AI prose reads as weak confidence. Where the prompt says [paste context], be specific.
M: Map
M1: The Comparable Triangulator
The role / service / product is [paste]. Triangulate the realistic
market range using public salary data, levels comparable sites,
recent reporting on the company, and any industry benchmark I should
know about. Give me three numbers: opening ask, target, walk away.
End with the factor in my profile that pushes me to the top of the
band or the bottom.
M2: The Anchor Reality Check
I am about to anchor at [paste number]. Pressure test the anchor.
Is it defensible given comparable data, my track record, and the
counterparty's stated constraints? Tell me whether it lands as
serious, ambitious, or unserious, and the specific evidence I should
have ready when they push back. Context: [paste]
M3: The Ceiling Probe
The counterparty is [paste]. Based on what I know about their
constraints (their comp band, their pricing floor, their fund size,
their budget), estimate the realistic ceiling for this negotiation.
Tell me what evidence supports the ceiling estimate and what would
move it higher. End with the move that would test the ceiling
without breaking the conversation.
M4: The Multi Component Decomposition
The offer / package / proposal is [paste base, variable, equity,
signing, benefits, other]. Decompose into realistic total value over
four years. Account for vesting, dilution risk, exercise costs,
probability of each component paying out, and time value. Compare to
my alternative. End with the gap that is real versus the gap that
is illusory.
M5: The Walk Away Math
My alternative if this conversation fails is [paste]. Dollarise it
honestly. Include the cost of search, the time to a comparable
opportunity, and the emotional cost. Tell me my real walk away
number, not the aspirational one. End with the specific terms below
which I should genuinely walk and not bluff. Context: [paste]
M6: The Hidden Cost Surfacer
The proposal is [paste]. Identify the costs that are not mentioned
in the headline number but will materially affect what I actually
take home or what I actually deliver. Equity exercise costs,
non compete time, ramp, hidden churn risk, customer concentration
implied by the deal. Rank by magnitude. End with the one cost I
should explicitly raise before signing.
M7: The Compounding Calculator
The current number on the table is [paste]. The likely next
negotiation in this relationship is in [paste timeframe]. Model the
compounding effect: every dollar I accept below market today
anchors the next conversation. Estimate the 10 year cost of
accepting the current number versus a number that is 10 percent
higher. End with the verdict.
M8: The Time Decay Audit
The deal closes in [paste timeframe]. Between now and then, what
external factors are likely to shift the realistic numbers (market
data refresh, company funding round, customer renewal cycle,
quarter end). Tell me whether I should accelerate the conversation,
delay it, or hold steady. Context: [paste]
M9: The Risk Adjusted Math
The offer includes [paste equity or variable comp]. Run the risk
adjusted math. Probability of the equity vesting at the stated
value, probability of the variable comp paying out, what the math
looks like at p25, p50, and p75 outcomes. Tell me the honest
expected value and whether the headline number is misleading me.
M10: The Reverse Cost Frame
The counterparty wants me at [paste their proposed number]. Reframe
to their cost of not closing this deal. What is the cost of a
prolonged search, a missed quarter, a partner walking, a price war
they triggered? Estimate. End with the specific dollar figure their
side loses by not meeting my number. That figure sets my real
leverage. Context: [paste]
O: Open
O1: The Timing Decoder
The window to bring up [paste topic: raise / price increase / budget
ask / counter offer] is [paste current situation]. Tell me whether
to open the conversation now, after the next milestone, or at the
formal cycle. For each option, predict the counterparty's
receptiveness and the cost of the delay. End with the recommended
timing and the trigger that moves it forward.
O2: The Three Openers
I need to broach [paste topic] with [paste counterparty]. Draft
three openers. First is warm and relationship anchored. Second is
direct and value anchored. Third is hardball and market anchored.
For each, predict the counterparty's first response and what it
signals about how the rest will go. End with the recommended
opener for this specific person.
O3: The Frame Setter
Before any number is on the table, the frame of the conversation
matters more than the math. The frame I want is [paste: business
performance, market correction, strategic priority, relationship
value]. Draft the opening 60 seconds that locks in that frame
without sounding scripted. End with the sentence that signals I am
not bluffing.
O4: The Compensation Question Deflection
The recruiter or counterparty asked "what are you looking for in
terms of compensation / pricing / budget." It is too early to
anchor. Draft three responses that buy me time without sounding
evasive. For each, tell me what signal it sends about my level and
how it shapes the eventual negotiation. End with which fits this
specific stage. Context: [paste]
O5: The Raise Request Drafter
I am asking my manager for a raise to [paste target]. My case is
[paste: scope expansion, market data, team retention]. Draft the
request as both a written note and a 90 second verbal pitch. Predict
my manager's most likely first response. End with the sentence I
should rehearse so the response does not throw me.
O6: The Price Increase Notice
I am raising prices on [paste customer] by [paste percentage]
effective [paste date]. They have been at the lower number for
[paste duration]. Draft the notice email. Two versions: one that
leads with the business reason, one that leads with the value
delivered. End with the version that fits this customer's
psychology based on context: [paste]
O7: The Budget Ask Drafter
I need [paste amount] for [paste purpose]. The approver is [paste
who and their priorities]. Draft the ask: the opening hook, the
business case in three lines, the ask itself, and the contingency
if denied. End with the specific sentence that pre empts the most
likely objection.
O8: The Fundraising Cold Outreach
I am raising [paste round size] for [paste company stage and stage].
The target investor is [paste]. Draft three cold outreach openers.
First leads with the market thesis. Second leads with the founder
story. Third leads with the specific reason this investor matters
for this round. For each, predict the response rate and what it
signals about my positioning.
O9: The Counter Offer Disclosure Timing
I have an alternative offer of [paste]. The current counterparty is
[paste status]. Tell me whether to disclose the alternative now, at
the next meeting, or only if directly asked. For each option,
predict how the counterparty plays the next move and what it costs
me to disclose at the wrong time. End with the recommended timing.
O10: The Backchannel Opener
The formal conversation is stuck or unavailable. The backchannel
person who can move this is [paste]. Draft the message that opens
the side conversation without going around my counterpart in a way
they would resent if they found out. End with the framing that
preserves both relationships if the move backfires. Context: [paste]
N: Navigate
N1: The Counter Offer Drafter
They opened at [paste]. My target is [paste]. Draft my counter.
Include the explicit ask, the rationale in two sentences, and the
question that keeps them in the negotiation. Predict their three
most likely responses and the right next move for each. End with
the version of the counter I should send today, not tomorrow.
N2: The Silence Decoder
I sent [paste message] [paste days ago]. They have not responded.
Tell me what the silence most likely means based on the
counterparty's pattern, the stage of the negotiation, and any other
context I have provided. Recommend the follow up move and the
specific timing. End with the version of follow up that does not
weaken my position.
N3: The Yes But Trap Audit
They said yes to [paste], but conditional on [paste conditions].
Audit the yes. Which of the conditions materially change what I
actually receive, which are negotiable, and which are non
negotiable? Tell me where they are using the yes to extract
something they did not have before, and the move that closes
without accepting the trap.
N4: The Concession Sequencing
I have room to concede on [paste list of items]. Sequence them.
Which to offer first to signal good faith, which to hold for the
end, which to refuse entirely. For each, tell me what the
counterparty will infer about my flexibility and what it costs me
in the final deal. Context: [paste]
N5: The Stall Reframe
The conversation has stalled at [paste sticking point]. The
counterparty keeps returning to [paste their position]. Generate
three reframes that change the question without conceding the
substance. For each, predict whether it unsticks the conversation
or escalates it. End with the recommended reframe and the sentence
that delivers it.
N6: The Power Move Read
Based on the context below, tell me what power moves the
counterparty is making (deadlines, walk away threats, third party
references, silence) and what each one actually signals about their
position. Tell me which moves to take seriously and which to ignore.
End with the counter move that holds my position without
escalating. Context: [paste]
N7: The Emotion Decode
The conversation is getting tense. The counterparty said [paste
specific moment]. Decode what they are actually communicating
underneath the words: pressure from above, fear of losing the deal,
genuine constraint, performance. Tell me which it is, and the
specific response that addresses the underlying signal rather than
the surface words.
N8: The Lateral Move
The cash number is fixed and below my target. Generate the lateral
moves I can negotiate that are worth real dollars: signing, equity
acceleration, additional vacation, title, scope, remote
flexibility, professional development budget, severance terms. For
each, dollarise the value and rank by likelihood the counterparty
will grant. Context: [paste]
N9: The Hold Strategist
They want my answer today. I want more time. Draft the response
that requests time without losing the deal. Three versions:
strategic (need to consult), tactical (need to verify a detail),
relational (need to discuss with a partner / family). For each,
predict how the counterparty reads it. End with the recommended
version for this specific counterparty.
N10: The Third Party Lever
I want to introduce external pressure: market data, the alternative
offer, a mentor's read, the board's stated position. Tell me which
lever fits this conversation, how to introduce it without sounding
manipulative, and the specific sentence that delivers the lever
while keeping the relationship intact. Context: [paste]
E: Escalate
E1: The Escalation Path Map
The negotiation is stuck at [paste]. Map the escalation paths
available: going higher in their org, bringing in a sponsor on my
side, formalising the conversation, walking away publicly,
introducing a competing offer. For each, score on probability of
moving the deal, cost to the relationship, and reversibility. End
with the recommended path and the trigger that activates it.
E2: The "Above My Head" Move
My counterparty has said the deal is at the limit of their
authority. Tell me whether this is a real constraint or a
negotiation tactic. If real, draft the message that asks for the
escalation without making my counterpart look weak. If tactic,
draft the response that calls it without burning the relationship.
Context: [paste]
E3: The Alternative Offer Play
I have an alternative offer at [paste]. I prefer the current
counterparty. Tell me how to introduce the alternative as leverage
without making them feel pressured into a yes they will resent.
Draft the message. Predict the three most likely responses and the
best next move for each.
E4: The Strategic Pause
The negotiation has lost momentum. Both sides are dug in. Tell me
whether the right move is to keep pushing, pause for [paste
timeframe], or signal I am ready to walk. For each option, predict
the counterparty's reading and the downstream effect. End with the
recommended move and the message that delivers it without losing
face.
E5: The Value Reframe to Strategic
The conversation has become transactional and price focused. The
counterparty is grinding on the dollar number. Reframe to strategic
value. Tell me the specific business outcomes that change for them
if they meet my number versus do not. Draft the reframing
statement that elevates the conversation without sounding rehearsed.
Context: [paste]
E6: The Coalition Builder
I cannot move this deal alone. I need internal support from [paste
likely allies]. For each, tell me what is in it for them to back my
position, the specific framing that makes it easy for them to
support, and the cost to me of asking. End with the order in which
to approach them and the message for the first.
E7: The Public Versus Private Position Audit
The counterparty has a public position of [paste] and what I
suspect is a private position of [paste]. Audit the gap. What
evidence supports my read of their private position? What move
would let them shift from public to private without losing face?
End with the specific opening for that move.
E8: The Information Asymmetry Closer
The counterparty knows things I do not know that affect the deal
math: their internal constraints, their alternative options, their
strategic priorities. List the three highest leverage pieces of
information I would need, the most credible source for each, and
the cheapest move to acquire each before my next meeting. Context:
[paste]
E9: The Final Push
We are at impasse. One more move from me ends the negotiation
either as a deal or as a no. Tell me whether the final push should
be a deadline, an ultimatum, a creative concession, or a walk away
threat. Draft the message for the recommended approach. Predict the
counterparty's response and the meaning of each possible answer.
E10: The Wrong Negotiator Audit
I have been negotiating with [paste counterparty role]. The
conversation has stalled. Audit whether I am negotiating with the
person who can actually decide. If not, tell me who can and the
specific way to surface the right person without making my current
counterpart feel circumvented. Context: [paste]
Y: Yield
Y1: The Accept Audit
The current offer is [paste]. Before I accept, run the audit. Is
this the best version of this deal I can realistically get? Have I
left obvious dollars on the table? Is there one more move I would
regret not making? Be specific. End with the verdict: accept now,
make one more move, or walk.
Y2: The Walk Away Decision
The terms are [paste]. The terms below which I should walk are
[paste my walk away]. The conversation has landed at [paste
current state]. Tell me whether to walk now, hold one more round, or
accept. Be ruthless. What am I rationalising versus reasoning?
Context: [paste]
Y3: The Strategic Hold
I want to delay closing without losing the deal. The reason is
[paste]. Draft the message that holds the deal in place for [paste
timeframe]. Predict the counterparty's read. Tell me what to do at
the end of the hold if their position has not changed.
Y4: The Counter Offer Trap Audit
My current employer / vendor / customer is countering with [paste].
Audit it. What is the realistic 12 month outcome of accepting based
on counter offer retention data, how this counterpart specifically
handles relationships that almost ended, and what the counter
actually fixes versus papers over. End with the verdict and the
sentence I use if the verdict is decline.
Y5: The "Good Enough" Test
The deal is at [paste]. My target was [paste]. I have been
optimising for [paste days / weeks]. Tell me whether the marginal
improvement available from continuing to negotiate exceeds the
marginal cost (time, relationship, signal of overreach). End with
the verdict on whether to close, push once more, or push twice
more. Context: [paste]
Y6: The Acceptance Drafter
I am accepting the offer / proposal at [paste terms]. Draft the
acceptance message. Three versions: warm and grateful, professional
and brief, strategic and forward looking. For each, predict how the
counterparty will read it and how it shapes the working
relationship from day one. End with the recommended version.
Y7: The Polite Decline Drafter
I am declining at [paste current terms]. I want to preserve the
relationship for the future. Draft the decline. Two versions: one
that leaves the door explicitly open, one that closes cleanly. For
each, predict the counterparty's response and the realistic
probability we reopen the conversation in 6 to 12 months.
Y8: The Renegotiation Audit
I want to come back to this deal in [paste timeframe] and ask for
more. Audit whether the asks are real and the timing is right. Tell
me what changes in my situation or theirs would actually unlock the
renegotiation, and what would make the second ask look like
overreach. End with the trigger that should restart the conversation.
Y9: The Regret Audit
Looking back from 12 months from now, where am I most likely to
regret the current decision? List the three most plausible regret
scenarios. For each, tell me the specific evidence today that would
predict it. End with the one move this week that would most reduce
regret probability. Context: [paste]
Y10: The Final Sign Off
I am about to sign. Run a last sanity check. What has changed since
I started negotiating that I have not re evaluated? What did I
agree to under pressure that I would not agree to in calm? What
specific clause am I assuming means something it might not mean?
End with the one thing to verify in writing before I commit.
Context: [paste]
The MONEY Framework in one image
M O N E Y
Map Open Navigate Escalate Yield
Five pillars. Sequential in rough terms but the loop is real. By Navigate you may be back in Map mode for a number you had not modelled. By Escalate you may be back in Open mode with a different counterparty. The point is not strict order. The point is that when you sit down at 11pm before a 9am money conversation, you can find the pillar that fits and run the right prompt rather than spiralling.
How to combine MONEY with your model of choice
ChatGPT: o series reasoning models are the right call for the Map and Y1 / Y2 audit prompts where the work is quantitative and requires multi step modelling. 4 series models work for the Open and Navigate pillars where the bottleneck is drafting messages in voice.
Claude: works well across all five pillars, especially when you load offer terms, prior emails, and the counterparty's public statements into a Project. Claude tends to be honest about whether you are reasoning or rationalising in the Yield pillar, which is where the most expensive mistakes happen.
Gemini: deep research mode is useful in the Map pillar when you are triangulating comparables, recent funding events, or industry benchmarks. Watch for context drift on the longest counter offer chains and switch to fresh chats if responses start to soften.
The cross model habit that pays compounding dividends is to run the comparable triangulator (M1) and the walk away math (M5) in two models. Where they agree, your numbers are robust. Where they diverge, the divergence reveals where your inputs were ambiguous and where you should dig before naming a number.
Frequently Asked Questions
Will the counterparty know I used AI to prepare for the negotiation?
Not if you use AI for the thinking and your own voice for the words. The signal of AI generated negotiation prose is the same as everywhere else: rule of three constructions, generic high impact verbs, balanced phrasing that hedges in characteristic ways. The Refine prompts in the HIRED Framework apply here too. Use AI for the analysis upstream. Rewrite the actual messages in your own voice before they go out.
How is the MONEY Framework different from generic negotiation books?
Negotiation books teach the concepts. The MONEY Framework gives you the specific prompts to apply those concepts to your specific situation at the moment you need them. The frameworks pair well. Read Voss or Fisher and Ury for the theory. Use the MONEY prompts for the Sunday night before the Monday meeting where the theory has to translate into a real number and a real sentence.
Do these prompts work for fundraising as well as salary negotiation?
Yes. The pillars are the same. The Map pillar covers comparable round sizes the way it covers comparable comp. The Open pillar covers cold investor outreach the way it covers raise requests. The Navigate pillar covers term sheet back and forth. The differences are in the inputs you paste, not in the framework. Founders running rounds use a different subset of the prompts than employees negotiating offers, but the structure holds.
Can I use these prompts with confidential financial data?
Check your model tier's data retention policy first. Enterprise tiers of ChatGPT, Claude, and Gemini typically offer the data retention controls that make this acceptable. Consumer tiers usually do not. For board level financials, cap tables, or sensitive customer pricing data, anonymise before pasting. The prompts work without the real names and the real absolute numbers.
What if I am bad at negotiating and these prompts feel above my level?
The prompts assume nothing about your negotiation skill. They assume only that you can paste accurate context. The Map pillar does the analytical heavy lifting that experienced negotiators do in their head. The Open and Navigate pillars do the drafting that experienced negotiators do from muscle memory. The Yield pillar audits the decisions experienced negotiators have internalised. Using AI as the level above your current skill is exactly the point.
Is there a paid version of these prompts?
Yes. The fifty prompts above are the free version, in compact form. The MONEY Pro Pack includes 150 expanded prompts with example outputs, ready to load Claude Projects and custom GPT configurations for each pillar, and role specific negotiation sets for software engineers, sales leaders, founders raising rounds, consultants pricing engagements, and executives negotiating exit packages. The Pro Pack is on the PromptLeadz Pro Collection at $29.
Where to go next
MONEY sits across the career and business arc. For the job search version of money conversations, pair MONEY with HIRED (which has its own Decide pillar covering offer negotiation). For the first 90 days where money may come up early, pair with LAUNCH. For the relationship side of money conversations (raising prices on a long term customer, asking a cofounder for a bigger share), pair with HARDER. For the moments when AI is agreeing with your aggressive number too easily and you need it to push back, pair with CRITIC.
The thing to internalise is that money conversations reward the side with better preparation more than they reward the side with more charisma. The person who walked in with a triangulated comp band, a dollarised walk away, a sequenced concession list, and three drafted reframes, beats the person who walked in with conviction and a vibe every time.
PromptLeadz publishes battle tested AI prompt packs for founders, product, sales, marketing, operations, HR, finance, customer success, adversarial thinking, hard conversations, new role launches, job searches, and money conversations. All prompts are LLM agnostic. Pricing is in USD.
Deixe um comentário: