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Deal OS v1.2 is out, and it's free. Last Tuesday I put it on sale. Since Friday it costs an email address, and if you're reading this, you already paid that. I'd rather more sellers run it than make a few bucks off it.
This Week in AI Sales
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ChatGPT builds slide decks now. OpenAI's release notes date ChatGPT Slides October 16th: a deck from a chat, your files or an outline, styled after an example deck you share, exported to PowerPoint or Google Slides. It's rolling out to eligible Pro, Business and Enterprise users. Give it your last winning proposal as the example and your call notes as the content.
Google Meet now translates live calls in 63 languages, guests included. Google's Workspace update from October 22nd says it works for guests from other companies when the organizer's plan covers it. Selling to buyers who'd rather talk in their own language? Send the invite from your own Workspace account, and test it on an internal call first.
Let's begin
I have a quick exercise for you. Pull up every deal you have committed for December. For each one, answer three questions without opening your notes:
Who runs their security review, and how long does it take?
Who on their side reads the contract?
Is this money in this year's budget, or next year's?
If you cant answer all three, the December date in your CRM is the date you'd like the deal to sign. Nobody on the buyer's side has agreed to it yet... and that's right where late deals slip, in the weeks between "yes" and a signature, on a step nobody owned.
And before you're all like "Jay, my champion said they'd handle procurement"... sure. Ask them who runs it and how long it takes. If they cant tell you, they're going to find out the same week day you do.
Last week I asked which level you're at. The answers were split, so this week's motion works at every level.
So this week, a paper map built from your call transcripts in three steps, the date each step has to start for your deal to sign in December, and the email that gets them moving. Then Deal OS, free.
Why the December Close Date Fails
Think about how that December date got there. Your manager asked what's landing this quarter, and you dragged the deal to December 18th because December 18th is in the quarter.
None of what happens after "yes" runs on that date. A security questionnaire takes weeks to come back. Legal works a queue (and you are not at the top of it). Procurement wants your tax form and insurance certificate in a portal you've never heard of. And in December, the people who approve things go on vacation.
So most reps find out what the paper looks like the week they planned to sign, when the champion says "great, I'll send it over to procurement"... and the deal moves to January. Sometimes the money moves with it.
(Paper Process is the P in MEDDPICC: every step between the buyer's yes and a signed agreement. Budget approval, legal review, security review, procurement and vendor setup, and the signature.)
Ask About the Paper on Call One, Then Count Backward
Write down what the buyer tells you about each step, in their words. Then count backward from the signature date to find the step that has to start first. Three steps per deal.
Step 1: The Paper Tracker, From the Buyer's Own Words
Attach every call transcript from the deal and run this.
Build a paper tracker for this deal. Every call transcript from the deal is attached. Use only those. Today's date is: [DATE]
"Paper" means every step between the buyer saying yes and a signed agreement: budget approval, legal review, security review, procurement or vendor setup, and signature.
Make a table with one row per step. The columns are Step, Buyer owner, How long, Date, State and Evidence.
- Buyer owner: the person or team the buyer named to run it. A team is fine if no person was named. Nobody named: UNKNOWN.
- How long and Date: only what the buyer said. Nothing said: UNKNOWN.
- State: CONFIRMED when the buyer said it in their own words. MENTIONED when only I said it, or the buyer guessed or hedged. UNKNOWN when nobody covered it.
- Evidence: the speaker and timestamp, like Dana [19:16], or NONE.
Always include these five rows, even if nobody mentioned them: Budget, Legal, Security, Procurement, Signature. Add a row for any other step the buyer named.
Quote marks hold only the buyer's exact words, copied exactly as the transcript spells them.
Then list every UNKNOWN as a question I can ask on the next call. One question per UNKNOWN, most important first.Every step the buyer never covered comes back UNKNOWN, with the question that fills it. That list is the agenda for your next call.
Here's the run on the made-up deal that ships with Deal OS, after one discovery call with Dana, the Controller at Calder Logistics:
Security came back CONFIRMED from Dana's own line at [19:16]: "IT does a security review. They send a questionnaire, and that usually takes them about three weeks." Procurement came back UNKNOWN in every column, because nobody asked. Budget came back MENTIONED, because her answer ended in "or find it somewhere."
Your number: steps with a named buyer owner, out of five. Calder scored four.
Step 2: The Back-Schedule
Paste the tracker, your target signature date and today's date. Where the buyer gave no length, put in your own. The prompt labels it MINE, so your guess never passes for their answer.
Here is my paper tracker:
[PASTE THE TABLE FROM STEP 1]
My target signature date: [Month Day, Year]
Today: [Month Day, Year]
For any step with no length from the buyer, use mine: [For example: "Legal: 10 business days. Procurement: 5 business days." Or NONE]
Using code, never mental math, work backward from the signature date. Count business days, Monday to Friday, and skip these holidays: [LIST, or NONE]. Steps run in parallel unless the tracker says one waits on another. Signature waits on every other step.
Give me a table with the columns Step, Length, Source, Latest start, Business days left and Status.
- Source is BUYER if the buyer gave the length, MINE if I did.
- Business days left: business days from today until the latest start.
- Status is LATE if the latest start is before today, TIGHT if it is 5 business days away or fewer, OK otherwise.
- A step with no length from the buyer or me gets ASK in every column after Step.
Then one line: the step most likely to move the signature date, and why, in plain words.On Calder, with December 18, 2026 as the target, security had to start by November 25th, legal by December 4th on my 10-day guess, and procurement by December 11th. Nothing was late yet. Budget came back ASK, and the last line named it anyway:
Most likely to move the signature date: Budget. Nothing is set aside today, nobody has given it a length, and Dana said she would have to get it into the budget for the fiscal year that starts January 1, 2027 "or find it somewhere"...
Hold onto that one. It comes back in Why This Works.
Your number: steps marked LATE, TIGHT or ASK.
Step 3: The Paper Email
One email to your champion that turns the map into dates.
Write an email to [CHAMPION'S NAME] about the paper on this deal. Use only the transcripts, my tracker and my back-schedule above.
The email:
- Opens with what they already told me about the paper, in their words. No praise, no thanks for the call.
- Names the step most likely to move the signature date, and why, in plain words.
- Names each step that is LATE or TIGHT and the date it has to start for us to sign by [DATE].
- Asks for one thing: 20 minutes next week with them and whoever runs each step that has no named owner, to put a date on every step. Offer two times: [TIME 1] and [TIME 2].
- Says I will send our security documents today, before the questionnaire arrives.
- Under 150 words. Plain words. No em dashes, and never "just", "touch base" or "circle back".
- Every date written out with its year.
Do not add anything they did not say. If a fact is missing, leave a [BRACKET] for me to fill in.Here's what it wrote for Dana, unedited:
Subject: Paper for December 18, 2026
Dana,
You told me: "Priya signs anything over fifty thousand." "IT does a security review." "They send a questionnaire, and that usually takes them about three weeks." "Legal looks at the contract." On budget: "I'd have to get it into that budget or find it somewhere."
Budget is the step most likely to move our date. Nothing is set aside for this yet, and the new budget starts January 1, 2027, two weeks after our December 18, 2026 target.
No step is late yet. The first to start is IT's security review, by November 25, 2026.
Could you and whoever runs procurement or vendor setup, if Calder has that step, give me 20 minutes next week to put a date on every step? I can do [TIME 1] or [TIME 2].
I will send our security documents today, before the questionnaire arrives.
SamIt quoted Dana instead of thanking her, and it asked about procurement because procurement was the only step with no owner. Both came straight off the tracker.
Send your security documents the same day. Security is usually the longest step, and the questionnaire is the one part you can answer before they ask. Then run the email through the Send Check (prompt 14 in Deal OS) before it goes.
Why This Works
Every length says whose it is. BUYER or MINE, on every row. When a date slips, you can see whether the buyer's number was wrong or your guess was.
Counting backward finds the step while there's still time to start it. On call one, the back-schedule said budget was the step most likely to move Calder's date. Two calls later, the CFO said it herself: "I can fund it from this year's budget if we sign by December 18. After that it goes into next year's budget, and that means April." That's one untimed step between a December signature and an April one. Security held too: on the same call she said IT sent the questionnaire November 20th, five days before the latest start the schedule gave it.
(And no, I didnt write the example to fit. Calder's three calls were written for Deal OS before these prompts existed.)
What's still unsettled. The tracker marked security CONFIRMED on "usually takes them about three weeks." Dana did say it, so the fact is right, but "usually" is her average and not a promise for this deal, and the tracker doesnt show the difference yet. And Step 2 runs legal and security side by side unless you tell it otherwise. At plenty of companies legal wont open the contract until security passes. If that's your buyer, write it into the tracker before you run Step 2.
Deal OS Is Free
Last Tuesday Deal OS went on sale. Today the paywall has been removed.
(If you bought Deal OS last week - THANK YOU! I appreciate your support. If you haven’t noticed yet, I’ve already refunded your purchase - check your email for a refund from our payment processor, Stripe)
The paper tracker is one piece of one play. Deal OS is the whole method:
A 49-page guide, with a quickstart for your role.
17 prompts and 14 Claude skills, from first outreach to close-out.
11 plays, including the full paper process: the approval matrix, getting security moving first, one shared copy of the contract, the weekly paper check-in, and the order to escalate a step that stalls.
A Company File and a Voice File, filled in once, so every draft knows what you sell and sounds like you.
The Calder deal from this issue, all three of its made-up calls.
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Know a seller with a December number? Forward them this.
Rep Action this week
Run Steps 1 and 2 on every deal you have committed for December, before your next forecast call. Count the steps that come back LATE, TIGHT or ASK. Every deal with one gets a paper call on the calendar this week.
And one question, because the answer decides a future issue... which step cost you your last late deal: budget, legal, security or procurement? Reply with one word.
~ Jay
The free section maps the paper and finds the step that has to start first. The Vault keeps every step moving until the signature.
This week in the Vault:
The Approval Matrix. Every approval on both sides, who gives it and above what amount, and the ones nobody has put in writing.
The Security Head Start. Draft answers to the questions every security questionnaire asks, from your own documents, before theirs arrives.
The Weekly Paper Recap. The recap to the buyer's owners, the update for your team, and who to go to when a step runs past its date.
Members get every Vault drop plus the full back library. $20/mo, or $140/yr and save $100.
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Click here for the stack I’d build today: https://www.sellingwithai.vip/stack
You just read the motion. Now run it.
The prompts, checklists, and templates that turn this into a 10-minute execution are in the Vault.
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