When a machine arrives, the person's job has to be rewritten from the promise made to the customer. Not from whatever the machine left behind.

Every automation I sold for two years caused friction after delivery, and it was never the machine. The machine had taken part of the work, and nobody had written down what the people were now for. This workbook is the fix, as seven decisions an executive makes in order, one page each, with a box for the answer and a prompt that fills the page in with you.

The seven pages

Two you make yourself. Five you build into the organization.

01
Start at the end: the promise
What the customer has been told to expect at this step, what keeping it costs once the machine arrives, and who owns the promise.
02
Redraw the lines: what actually moves
Where the customer's work now stops, where a person stops and the machine starts, and who maps both.
03
The job on the far side of the line
What the machine decides, who answers when it is wrong, and the person's job written so it can be hired for.
04
Build the machine to the job
The order of spending: the promise, then the job, then the machine. Who signs off at each step.
05
Inside or outside
Who loads the machine before it runs and who handles what comes back: an employee, a contractor, or a partner.
06
The first ninety days on the line
The new job, not the old one: learning, contributing, owning, with what you review at each mark.
07
Hold the line: the weekly meeting
Who is in it, how long, and the two clocks on its agenda, so you know the line is still in the right place.

The problem I had

At LendingTree the internet took the research and the mortgage application away from the sales rep. The brand promise was still on the air.

That brand promise is an important part of this narrative because it created the expectation that was never delivered once the customer met the salesperson.

The customer finished a long application and got one call with one rate. The ads had promised banks fighting for their business. So the customer went back out and shopped, and the company lost a sale it had already paid to attract. Nothing was wrong with the machine. The person's job had been left over, not rewritten.

What the pages show

Seven decisions, in the order that keeps the promise. The first two are the executive's own and cannot be handed off: what we promised, and where the customer's work now stops. The next five build the practice into the organization: the job on the far side of the machine, the order of spending, who does the two jobs a machine creates, the person's first ninety days, and the weekly meeting that keeps the line where it belongs.

Each page has the same parts. What you leave with. Three sections, three questions each, a box. My own answers as the worked example. Three steps, one action, and a prompt you paste into whatever AI you use so it interviews you and fills the page in.

What changed

At LendingTree the fix was not a new system. It was a decision about a role.

I made sure that they played the role of advisor. I would tell them to assume they are sitting on the same side of the table as the homeowner.

Write the person's job from the promise. Then build the machine to that job.

Receipts

Where this came from

Source: My own account of LendingTree, about 2004 to 2008, and of client work since, with client names withheld. The shape of the pages is Caleb Ralston's free brand workbook, which turns from the founder's own work to building the team; this one does the same for an executive putting AI into the customer's path.
Read: 2026-09-21. Seven pages compiled from the written record of the practice, then read three times by readers who had seen none of it, and rewritten until they could fill the boxes from the page alone.
Method: One decision per page. Every claim on a page traces to the record by number; every quoted line is mine, dated. Nothing on any page claims a result I did not keep.
Unfinished: This is a draft. No page has had my pass yet, the opening letter is not written, and the workbook does not have its name. The finished version replaces this file, and the address on this page does not change.

When a machine arrives, the person's job has to be rewritten from the promise made to the customer. Not from whatever the machine left behind.

The workbook, all seven pages, and the sheet that holds your seven decisions.