AI Secret Sauce Night Four: Finish the Autopilot

Cowork Chilliwack, Monday, October 19, 7:00 to 9:00 PM

About AI Secret Sauce: five real-world, in-person classes at Cowork Chilliwack for local, tech-savvy entrepreneurs. Over the series I teach the secret unlocks that help you automate your business with AI, and I show every step live, at normal speed, with nothing hidden. See the series and RSVP for the last night, or start with the Night One recap for the five unlocks.

Night Three was the first time Claude drove the apps for us. We left that night with phase one of a real automation built on Tim McAlpine’s real business: a member books a room through the website, a Zap checks the calendar, and a clash gets flagged instead of booked over. Night Four picked up exactly there. Before we built anything new, we asked whether phase one had survived a week on its own. Then we made one decision, built the next phase, and kept going after the room emptied until Tim’s Claude session hit its limit for the night.

Here are the slides from Night Four. Every phase in the printed case file has a brown box of text, and that text is the whole method: it is the prompt you paste into Claude. You can contact me for the handout.

First, is it still on?

Slide six is a read-only prompt. It asks Claude to look at Zapier, Google Calendar, Gmail and Sheets, name the Zap, say whether it is on, count its runs since October 13, and change nothing. Tim read it off the screen into his voice typer and Claude reported back: the Zap called “Member booking, with calendar check” was switched on, had run 18 times on real member bookings in six days, had failed zero times, and had written one row per booking to the Hours log tab. It had only read data and changed nothing.

That is the quiet part of this course that I care about most. A week of real bookings went through something built in a single evening by a business owner who does not write code, and it held.

Tim then showed the room what Claude had built underneath it. A Member lookup tab that pulls each company’s included hours and renewal day from the columns he already fills in by hand, without ever touching them. A daily check that logs into the form software, notices a new member or a fixed typo, and emails a short report every morning. And one cell that made everyone laugh: a custom spreadsheet function so long it filled the screen, written by Claude so the hours could be totalled against each member’s own renewal date. Tim does not have to understand that formula. He has to understand that it works beside his data, not on top of it.

One wrinkle came up. Tim had run a test booking on top of the AI Secret Sauce class itself, and the conflict flag had not appeared right away. It showed up after a refresh about an hour later. Rather than guess, Tim held the voice key, described exactly what he had seen, and gave Claude the job of finding out why. That is the habit I want everyone to leave with. When something looks wrong, you do not open the Zap editor. You describe what happened and let the tool investigate.

One decision before we build: when does the hold go on?

Outside rentals come through a different door than members. Today a request arrives from the website form, the community manager checks the calendar, replies from a Gmail template with the booking link, and types two asterisks on the calendar to hold those hours until the renter pays. Everyone at Cowork knows two asterisks means a hold. Phase two replaces all of that, but there was a choice to make first, and I put it to Tim out loud.

Option A: hold at submission. The moment the form is submitted, a hold goes on the calendar, before anyone has said yes. If nobody pays, it drops off by itself after 48 hours. A request you turn down blocks the slot until you delete the hold or it expires. One Zap.

Option B: hold when you approve. The reply is drafted right away, but the hold only goes on when a person presses Send on that draft. Nothing blocks the calendar until someone has said yes, which also means a member could still book the slot in the gap. Two Zaps.

Tim picked Option A. An unapproved hold is safer than an unguarded slot, and a hold that expires on its own costs nothing. Slides eight and nine hold the prompt for each option, and the case file says to use one or the other, never both.

Phase two, built live

Before pasting the prompt, Tim cleared his context. A question came from the room: if you clear, how does Claude still know what it is working on? Because the project files, the connectors and the instructions file are all still there. The chat history goes, the work does not. More on that below, because it was the best question of the night.

The Option A prompt asks for a Zap called “Rental request: hold and draft”. When the rental form is submitted, check the Cowork Chilliwack Bookings calendar for that room and time. If it is free, add a hold with the requester’s name and the room in the Location field, set to expire if unpaid after 48 hours. If it is busy, add nothing. Either way, create a Gmail draft from the info address using the usual reply: available with the link to book, or not available with the next free times. Tag the subject so the front desk can sort at a glance. Never send. Show the plan first, ask about anything unclear, and leave it switched off.

Claude came back with its plan and its questions, the same way it did on Night Three. It noticed that phase one already treats any calendar event with a room in the Location field as busy, so the new holds would automatically block member bookings too. Then it asked for the reply text for each case, the booking links, the hours that count as after hours, and what to do with a hold once it expires. Tim answered by voice. Rentals run eight to five. The rooms are the small meeting room, the large meeting room and the studio. Unpaid holds can be deleted after 48 hours. When a slot is busy, look for free times in the two days either side of the request.

The reply templates were the interesting problem. Tim had three Gmail templates, one per room, and he pasted them in. Then he asked the question that turns a one-off into a system: his team tweaks those templates now and then, so could the Zap read them from somewhere instead of having the wording baked in? Claude suggested a Google Doc. Tim added the Google Docs connector in Claude’s settings while we watched, and we hit the limit of that connector straight away: it can read and edit a document that already exists, but it cannot create one, and Zapier had no Google Docs connection of its own. Tim connected Google Docs to Zapier, Claude wrote the five replies (available, unavailable and after hours, with the room variants), and they now live in a document that the Zap reads on every request. Tim’s community manager already works from a standard operating procedures document that she calls invaluable, so the new one is linked from there rather than buried inside it.

Then the test. The first test request produced a draft but no hold. Claude had quietly built the Option B behaviour, hold on Send. Tim told it so, in plain words: the hold is supposed to go on the calendar immediately, without a person, and we are not seeing one. Claude fixed it. A second test put a hold on the 27th, though it took a few minutes to appear, so Tim asked what the actual delay was and whether it could be faster. By the final test the hold was on the calendar about 20 seconds after the form was submitted, and a member booking on top of it came back as a clash. The outside door is guarded.

A few small things we fixed along the way, all of them worth knowing before you build your own:

• Subject lines. The draft said “free” when a slot was open and “busy” when it was not. Tim changed those to “available” and “unavailable”, so a reply on a phone reads “Unavailable, small meeting room” at a glance. He also wants a red cross or a check mark at the front of the status the member form shows, for the same reason: less thinking at the counter.
• The Gmail signature. Drafts made by a Zap do not carry your signature unless you switch it on for them. Claude flagged it, Tim said yes.
• Where did my Zaps go? Zaps that Claude builds through the Zapier connector show up under their own “NextGen” heading, and only for the account that built them. Tim’s new Zaps looked missing until he found that bucket. Nothing was lost, and the separation turns out to be handy.
• After hours still gets a hold. The first version only held office-hours requests. Both should hold. Said once, fixed once.
• Read it as a page, not a wall of text. When Claude lists a long set of remaining steps, ask it to make a beautiful HTML artifact and open it in Chrome. It takes under a minute, it has checkboxes, and you can share the link with whoever is helping you.

Member bookings, finished

While we were testing, a second member booking on a held slot showed up as a normal booking for a minute before turning into a clash, which is the same delay Tim had noticed earlier in the day. Claude found the cause: the original member Zap from before the course was still running alongside the new one, so every booking was going through twice. Claude offered two ways to finish it. Tim chose the clean one: member bookings go straight onto the calendar in their final state, checked first, never placed and then corrected. Claude warned that if that Zap ever failed, no event would be booked at all, so Tim’s instruction was to make sure it cannot fail quietly and to get the timing as low as possible. The old Zap was switched off by name.

The result, in Claude’s words: member bookings now land on the calendar in their final state about five seconds after submit, with an alert email if a run ever fails. We tested a clash and the form came back red on the spot. Tim’s community manager used to prevent double bookings by hand. Both doors now do it themselves.

What we did not get to

The scoreboard on slide four said all four remaining phases tonight. We finished phase two and the member side, and the session limit called time. Phase three, where a Stripe payment link turns a hold into a paid rental, needs a rethink before it is built: Tim’s rentals are paid through Squarespace, which sits in front of Stripe, so the prompt on slide 13 has to go through that door. Phase four, the overage invoice in Zoho Billing on slide 15, is the same shape. Phase five, the Monday morning digest of after-hours bookings, is homework.

Usage limits are a real thing you plan around. Long project chats fill up. When you finish a subject, run the compact command or ask for a handoff file, and start the next subject clean.

Questions from the room

The best parts of these nights are never on the slides. We had two guests join Tim this time, and one Cowork member who had been at Nights One and Two.

Does clearing the chat stop hallucinations? Partly, and for a reason you can picture. The model we were using can hold about a million tokens, roughly a thick book. Every message you send, it rereads all of it. A long session accumulates stale facts, reversed decisions and files that have changed since it read them. Acting on that old picture looks like a hallucination but is really drift. Ask about two similar client proposals in one thread and it starts blending them. Clearing before a new topic removes all of that. The model keeps nothing except the instructions you load for the project.

Can I ask a side question without polluting the context? Yes. There is a slash command called “by the way” for exactly that. I used it live to ask Claude whether clearing helps with hallucinations, and the answer above is partly its own.

Should I give Claude my QuickBooks? This one deserved a careful answer, and two people in the room gave it. The risk is what security people call the lethal trifecta. Picture a bank: one person is good at talking to people, one owns a fast car, one has keys to the vault. Each is harmless alone. Together you have a robbery. An AI that can read your private data, read the open web, and take actions is the same three people in one. A web page can carry instructions aimed at the AI, and if the AI also holds your books and can act, you have a problem. Connectors show you a list of permissions when you connect them for a reason, and so do API keys when you create them. Tim keeps a hard line around his password manager and his financial data, and his business keys live in his own safe, Infisical, instead. One guest added the other half of the answer: accounting data is confidential, and what you feed a hosted model may teach it. Use AI for the structure of your work, the forms, the calendar, the templates, and keep the confidential records out of the chat. I wrote more about this in the lethal trifecta for small business.

What is a power user? Someone who lives in keyboard shortcuts and never reaches for the mouse. The terminal version of Claude Code is for those people. The desktop app is for everyone else, and it does the same work.

What goes in a CLAUDE.md file? The project instruction file that Claude reads at the start of every session, kept to about 80 lines: what the project is, which rules apply, what never to touch. There is a global one and a per-project one, and the project file wins. Tim asked for best practices and I owe him a write-up.

One guest’s verdict at the end of the two hours: “This was outstanding. We just hit the tip of the iceberg.” That is about right. Tim’s problem is a mundane one, a room calendar, and that is exactly why it teaches so well. Everyone in the room has one like it.

Why this matters, in one story

Tim told a story that has nothing to do with Zapier and everything to do with why you automate. Cowork’s community manager had been on the job two weeks when she asked if she could try something funny on Instagram. Her first post was about an Indigenous fashion designer from Chilliwack whose cardigan had been worn by an actor on Truth and Reconciliation Day. She researched the story, told it properly, and the post did many times the account’s usual engagement. The designer’s collection had already sold out on the strength of that sweater, with a pre-sale behind it. The point of the autopilot was never the calendar. It is the hours it hands back to the person who used to prevent double bookings by hand, so she can do the work only a person can do.

Before Night Five

The case file ends with homework, and it is the same for Tim and for everyone building their own:

1. Let the Zaps run on real bookings for a week. Press Send on every draft yourself. Tim wants a person reviewing each reply for now, because requests come with notes like “can I bring a caterer?” that a template cannot answer.
2. Note any draft you had to change and any booking it got wrong. Bring the list.
3. Run the adversarial review on slide 17. It is the reviewer from the BMAD method you met on Night Two, the one that is not allowed to say “looks good”. Decide which findings are real, then say which to fix.
4. Pick one repetitive job in your own business and write down, in plain words, what “done” looks like.

Journal prompt

The last slide every night is the same, and it is the one people skip. Before you close the laptop:

Write a plain-English journal entry of what we did tonight, including anything still not finished.

Claude writes it from the session it just lived through. A week later, when you open the project again, that entry is the fastest way back in.

Want me to set this up for you?

Everything we built on Tim’s accounts is what I set up for local businesses one on one. See the Small Business AI Setup, or get in touch and tell me what you would like to stop doing by hand. After the series ends, the same material moves online: Monday nights, from wherever I am.

Thank you

Thank you to Tim for the room, the screen and, once again, his real business as the guinea pig, and to everyone who came out on a Monday night and asked the hard questions.

---

Keep reading

• AI Secret Sauce Night Two: Build Your AI Team: the safe, the voices and the team that first mapped the booking problem
• AI Secret Sauce: Foundations Class: Night One, the secrets, bots and API keys underneath all of this
• Night Three slides: Talk to Claude, Let It Drive: where phase one was built
• The Lethal Trifecta for Small Business: the security question from the room, written down
• Why I Love the BMad Method: the adversarial reviewer in the homework
• An Easier Way to Manage an Agentic Team: where Rakazo comes in on Night Five

Journalists and event organisers: photos, a print-ready poster and a short bio are all on the media page.