The owner already knows what to automate first. Nobody ever asks him

I'm sitting with a man who runs eight hotels and I'm about to ask him the boring questions. Timeline, budget, and do you want this scoped as one process, one department or the whole company. I get about half of that out and he takes the pen off me.

"I'm going to take X amount of hours and this is the number of hours and this is the price per hour is what it's going to cost to do this, this process etc. And then we'll make that commitment and then we'll see. But we won't get any commitment beyond that."

Fixed hours, fixed price, one process, nothing promised past it. That's a better scope than the one sitting in my own proposal template, and he built it out loud in one breath while I was still reading from mine. Then, unprompted, he widened the starting scope from one hotel to all eight.

He'd also had a proposal from another AI firm on his desk since June. Ten grand for the discovery and then something in low six figures for the build, and he'd never signed it. Cost was one of three reasons he gave me and it wasn't the biggest one.

It's happened three times in a month

A few weeks later I'm on a call with the only paid person at a small nonprofit in the North Bay, walking her through two options I'd put together, and halfway down the second one she stops me and invents a third.

"What if we completely change this, I was able to get you all of the information, and then you would clean it up and turn it into a finished product."

She'd pull every export herself and hand it over, I'd clean it and build from there. She wasn't haggling. She was moving each bit of the work to whoever was cheaper at doing it, which is exactly what I'd have done in her chair and did not think to offer her.

Then a property management owner running about a few hundred units around the Bay Area. I asked where the time goes and he designed the payables automation himself, out loud, in one go. Set a threshold, auto clear the low risk invoices, push anything outside the band to a person. He set his own target before I could offer one, from a hundred invoices a day down to fifty.

Three owners in three different trades, and not one of them needed me to tell them what to automate first. All three of them told me, before I'd finished pitching.

The question that gets there in under two seconds

Nobody I meet is confused about their own business. They're confused by the volume of stuff being shouted at them about AI. One owner I sat with this summer already has Claude wired into his property software and his email, instruction sets built, some of his reporting going out on its own, and he still couldn't tell me where to start. His words were that you get hit with a fire hose of information. The daily user and the fella who has never opened any of it are stuck on the exact same step.

So I stopped asking owners what they want to automate. Nobody can answer that. This is what I ask instead:

"500k to hire a team. What departments would you hire?"

Imaginary money, no constraint, and no software anywhere in the question. Every owner I've put it to so far, around Marin and the wider Bay Area, force ranks their own pain list in under two seconds, because it's the sum they've already done in their head at 5am.

A furniture maker answered it this summer and then went further than the question. He's been down an employee since the month before, ninety percent of what he sells is product he draws by hand, and he told me straight out that more business right now would break him. So we're not going near his marketing. Capacity first, then demand.

Ask what they'd do with it, not what they want

The second question is simpler. If all of this worked on Monday, what's the first thing you'd actually do?

The woman at the nonprofit didn't say save time. She described one list, in December, of every donor at five hundred dollars and up, with addresses on it, for Christmas cards. And a second list of everyone who gave a thousand or more five years ago and has given nothing since.

"These are the 30 donors who donated 500 plus. This is their address."

That's a spec. Thirty rows, two fields, one deadline, and I know exactly what it looks like when it has failed. Ask an owner what they want and you get a category back. Ask what they'd do with it and you get a list, and the list is the build.

Watch what people skip

The third one is free, because it's already sitting in the room.

A surgeon showed me his order templates. They exist and somebody built them properly. And he finds it faster to retype the level, the procedure and the codes from scratch every single time. He wasn't even complaining about them. He just doesn't use them.

That's the diagnosis, handed over for nothing. The templates nobody opens and the report that gets printed and binned will tell you more in ten minutes than an hour of asking staff what's broken. Watch what people walk around.

And a decent chunk of what turns up in that walk shouldn't be automated at all. A hotel controller put it better than I ever have:

"So not everything needs to be built and the best tool is no tool."

He's right, and agreeing with him costs me money every time.

Before anybody sells you anything

Nobody has ever asked you these questions and that isn't your fault. Every person who has walked into your office carrying technology arrived with the answer already written down before they met you. I've done it myself. My prep for one meeting bet the whole thing on workers compensation reporting being the pain, and it never came up once in two hours, not one mention.

Almost nothing about how your shop actually runs is written down anywhere, though. It's in your head and in one other person's head, and that's a fair part of why the tools you've bought went quiet once the novelty wore off.

So before you pay anyone, me included, sit down for half an hour and answer these. If you had five hundred grand to hire with tomorrow, what are the first two roles? What's the first thing you'd genuinely do on Monday if all of it worked, and can you write it out as a list? Which job in your office does everybody quietly do the long way round? Who is the one person who knows how that job is actually done? And what happens the week they're out sick?

Not one of those is a technology question and you don't need me for any of them. Do that first and the thing you end up buying is nearly always smaller and cheaper than the thing you were about to buy.

I'm in Tiburon, so I'm 20 minutes from most of Marin, and I'd rather do this standing in your office than on a call. Send me two things. First, your answer to the five hundred grand question, just the first two roles you'd hire, no explanation needed. Second, the one job in your week that somebody always does the long way round because the proper way is slower.

I'll come back and tell you which bit of that is worth building and which bit is just a step somebody should have deleted years ago. Costs you nothing. Plenty of the time the whole answer is the deleting, and I'll say so rather than sell you the build.

Book 20 minutes, or email jay@jaimate.com with the two answers.