There's a conversation most business owners have been putting off for somewhere between eight months and four years, and it's the same conversation every time.
What you charge is wrong. You know it's wrong. You've known for a while. And every time you sit down to fix it, you get about ten minutes in, realize you don't have the numbers to defend a new number, feel a small wave of dread about the clients who'll push back, and find something more urgent to do.
I've done this. Twice, for embarrassingly long stretches. The second time I was underpricing a service by about forty percent and I knew it, and I kept not fixing it because fixing it required a conversation and the conversation required certainty and I didn't have certainty.
What finally broke it wasn't courage. It was doing the arithmetic in a way that made the answer obvious enough that the conversation stopped being scary.
So today's vault is seven prompts about price. Not seven prompts to generate a pricing page. Seven prompts that walk you through the thinking, in order, and end with you having an actual number you can say out loud without your voice doing that thing.
A note before we start. These work best if you run them in one sitting, in sequence, in the same conversation, because each one uses what came before. Block ninety minutes. And a warning that some of you will find the second one genuinely uncomfortable. That's the point of it.
One. The cost floor
You cannot price anything until you know what it costs you to deliver it, and most owners are working off a guess that's roughly half the real figure.
I run a business that delivers [describe your service or product]. I want to calculate my true delivery cost per unit, and I want you to interrogate me rather than accept my first answers.
Ask me, one question at a time, about every input that goes into delivering one of these: my own hours and what they're worth, team hours, contractor costs, software allocated per unit, materials, the revision and rework I actually do versus what I quote, the sales time it took to win it, and the admin and invoicing tail afterward.
When I give you an hours estimate, push back once and ask whether that's the number for a smooth one or the number for an average one. Include the average.
At the end, give me a delivery cost per unit, a breakdown, and the three inputs I'm most likely underestimating.
The interrogation instruction is doing the heavy lifting. Left alone, you'll answer these questions optimistically, because you're remembering the projects that went well. The pushback catches that.
If you actually track your time, feed it real data instead of estimates. I use Rize for this and the gap between what I thought a certain kind of project took and what it actually took was about sixty percent. Sixty. That's not a rounding error, that's a business model.
If you don't track time, run this prompt anyway with estimates, and then go track for three weeks and run it again. The second answer is the real one.
Two. The silent discount
This is the uncomfortable one.
Here's my current pricing and what's included: [paste it].
Here's what actually happens on a typical engagement, including things I do that aren't in the scope: [describe honestly, including the small favors].
Identify every place I'm delivering value I'm not charging for. For each one, estimate what it costs me and categorize it as: worth keeping as a relationship investment, should be priced, or should stop.
Then tell me the total annual value of everything in the "should be priced" category. Give me the number even if it's ugly.
Everybody has these. The quick call that turns into forty minutes of consulting. The "one small change" that's the fourth one. The report you started sending as a courtesy that's now expected. The Sunday text you answer.
None of these felt like anything when they started. Added up across a year and a client roster, they're frequently the difference between a business that's tight and a business that's comfortable.
The categorization matters, though. Some of this stuff should absolutely stay free. Generosity is real and it compounds and I'm not telling you to bill in six minute increments like a divorce lawyer. I'm telling you to know which generosity you chose and which just happened to you.
Three. The comparison you're losing
You are being compared to something. You almost certainly don't know what.
I sell [service] to [customer type] at [price]. When a prospect is deciding whether to buy from me, list every alternative they're realistically weighing, including the ones that aren't competitors: doing nothing, doing it in house, hiring a junior person, using software, hiring a cheaper provider, hiring a much more expensive provider.
For each alternative, tell me its real cost to them including hidden costs, what it gives them that I don't, and what I give them that it doesn't.
Then tell me which alternative I'm most likely losing to without knowing it, and what I'd have to prove to win those.
The answer that surprises people most often is "doing nothing." A huge share of lost deals aren't lost to a competitor. They're lost to inertia, and you'll never see them in a win loss report because they never became a deal.
If that comes back as your main competitor, your pricing isn't the problem. Your urgency is.
Four. The walk away number
Before you set a price, you need a floor, and the floor should be decided in a calm room rather than in the middle of a negotiation.
Based on my delivery cost of [number from prompt one] and the uncaptured value from [prompt two], help me establish three numbers.
My walk away price: below this, I'm actively losing money or capacity I could deploy better, and I decline.
My standard price: what I quote by default with no justification offered.
My stretch price: what I charge when the work is urgent, complex, or high stakes for the client.
For each, tell me what has to be true about the engagement for that number to be right, and give me one sentence I can say out loud to justify it without apologizing.
The last instruction is the one that matters. "Without apologizing" is a real constraint and models will hedge if you don't specify it. You want a sentence, not a paragraph, and it should be a statement rather than a question. There's a difference between "it's twelve thousand" and "it would be around twelve thousand, does that work?" and the difference costs you money on every single call.
Five. The objection rehearsal
Now you practice, before it's live.
You're playing my client. Here's who you are: [describe them, their business, their budget pressure, how long we've worked together, how they've behaved in past negotiations].
I'm about to tell you my price is going from [old] to [new]. Push back the way this specific person would. Be realistic, not a cartoon. If they'd go quiet and think, go quiet. If they'd mention a competitor, mention one. If they'd get warm and personal about it, do that.
Stay in character for the whole exchange. After five rounds, break character and tell me which of my responses was weakest and why.
This is the prompt in this list that I use most, and not just for pricing. Rehearsing a hard conversation against something that pushes back is enormously more useful than rehearsing it in your head, where you always win.
The "be realistic, not a cartoon" line matters. Without it you get a caricature who either folds instantly or turns into a villain, and neither prepares you for a real person who's mostly reasonable and a little annoyed.
THE FULL VAULT
Every prompt from this issue plus forty more, organized by situation, with the variations that work when the first version doesn't. Inside the AI Workflow Blueprint.
Six. The letter
Draft the message telling an existing client their price is going from [old] to [new], effective [date].
Constraints: no apology, no lengthy justification, no framing that invites negotiation. Lead with the change, not the buildup. Acknowledge the relationship in one sentence without being sentimental about it. Give them a clear effective date and one specific thing that gets better for them.
Keep it under two hundred words. Write it the way a confident person writes a routine business message, because that's what this is.
The three constraints in the second paragraph exist because the default output on this prompt is a groveling nightmare. Models are trained to be agreeable and a price increase letter written agreeably reads like you're hoping to be talked out of it.
The "lead with the change, not the buildup" instruction is worth stealing for other things too. Burying the news under three paragraphs of appreciation makes the reader anxious and then annoyed. Say it, then contextualize.
Do write the actual final version yourself. Use this to get past the blank page and to see the shape, then put it in your own words. A price letter is exactly the kind of message where sounding like a person matters, and if you're publishing under your own name in a world where machine text is increasingly detectable, this is not the document to hand over wholesale.
Seven. The ladder instead of the discount
Last one, and it's the one that saves relationships.
A client says my new price doesn't work for their budget. Instead of discounting, design me a ladder of alternatives that reduce what they get rather than what they pay per unit of value.
Give me five options ranging from small reductions to significant ones. For each: what they give up, what it saves them, what it saves me in delivery cost, and whether it's a good deal for me at that price.
Flag any option where I'd be doing meaningfully more work per dollar than at full price, because those are traps.
The instinct when someone balks is to knock ten percent off and keep the scope identical. That's the worst available move. It teaches the client that your price is soft, it doesn't reduce your cost, and it makes the next negotiation harder.
Reducing scope keeps the price honest. Fewer deliverables, longer timeline, less access, self serve instead of done for you, quarterly instead of monthly. The client gets to choose what matters to them, which usually reveals that the thing they were about to pay less for wasn't the thing they actually valued.
The trap flag at the end is important. Some scope reductions cut your revenue faster than your cost, and those look like compromises and function like losses.
Running the sequence
One sitting, in order, same conversation so the context carries. Ninety minutes.
What you'll have at the end is a delivery cost you believe, a number for what you've been giving away, three price points with justification sentences, a rehearsed objection, a draft letter, and five alternatives to discounting.
What you'll also have, and this is the part I didn't expect the first time I ran it, is a strange calm about the whole thing. The dread around pricing conversations is almost entirely a dread of being asked a question you can't answer. Once you can answer every question, the conversation is just a conversation.
One practical note. Do not send the letter the same day you write it. Sit on it overnight, read it out loud in the morning, and cut whatever you added to soften it. There's always something.
WORK THROUGH IT WITH SUPPORT
The AI Business Accelerator runs this sequence with you on your real numbers, plus the rest of the operating system. Six weeks, live teardowns, no theory.
If you only run one of these, run the second one. The silent discount. It's the least fun and it will tell you more about your business in twenty minutes than the other six combined.
Then go say the number.
See you tomorrow.
Jordan
The AI Newsroom is written by Jordan Hale. This issue contains affiliate links to tools I actually use. If you sign up through them I may earn a commission at no extra cost to you.