Outreach and the email strategy

This is the chapter with the one rule that isn't up for debate: Claude drafts, and you send. Every email to a vendor goes from your own inbox, read and approved by you. Claude never sends anything, and never writes to anyone as if it were you.

Why the rule

It isn't because Claude writes bad emails. It writes good ones. It's because of what an email to a vendor is.

• Vendors think they're talking to you. A photographer replying to "Riley" is building a relationship with Riley. If the email came from software, that's a small deception, and you'll be the one meeting them on the day.
• Emails make commitments. "Yes, please hold the 4th" can cost a deposit. "That sounds fine" can be read as agreeing to terms. Only you should be able to say those things.
• Mistakes go out in your name. A wrong date, the wrong vendor's name, a guest count from last month. You catch those by reading before you send.
• Your inbox is a place other people can write to. Anthropic's own safety guidance for Cowork warns that if Claude reads malicious content mid-task, it could act on instructions hidden in it before you notice. A rule that Claude never sends is the simplest guard there is.

Gmail's connector can send, reply and forward, and by default Claude asks you before each one. Keep that default on. Better still, never ask it to send. The project instructions in chapter 2 tell Claude to draft only, and it's worth saying again in any chat that touches email.

I built the other version once: an agent that fills venue inquiry forms and reads the replies. It works on mock venues, and the demo shows every step. It never ran for real, for the reasons above.

Two ways to draft

• In the chat. Claude writes the email in a code block. You copy it into your own email, edit it, send it. Works on any plan, no connector needed.
• As a Gmail draft. With Gmail connected, ask Claude to save the email as a draft. It appears in your Drafts folder. You open it, read it, change what needs changing and press send yourself.

Either way, the email goes from your account, under your name, because you sent it.

A shared address, if you want one

Some couples set up one email address just for the wedding and both read it. It keeps vendor threads in one place and out of your work inbox. If you do, log every email in the Outreach tab anyway, because each of you connects Gmail in your own Claude, and the other one's Claude can't see that inbox.

The templates

Write each template once, with Claude, then reuse it. These are starting points. Make them sound like you.

First inquiry

Write a first inquiry email to [vendor] from [Sam]. Use our brief. Say who we are in one line, our date range, rough guest count and location, and why we're writing to them specifically (from the "Why it fits" column). Ask these questions as a short numbered list: [paste the question list for this category]. Ask for a quote or price list and their availability. Under 150 words. Don't mention our budget.

Follow-up

Draft a short, friendly follow-up to [vendor]. We wrote on [date] asking about availability and pricing for [date range] and haven't heard back. Two or three sentences. Restate the one thing we most need to know.

Clarifying a quote

Here's [vendor]'s quote (attached). Compare it with our question list for this category. Draft a reply asking about anything they didn't answer or that's unclear, as a numbered list. Thank them in one line, no more.

Saying no

Draft a short, warm note to [vendor] saying we've gone another way. Thank them for their time and the quote. Don't give a reason. Two sentences.

Should you mention your budget in a first email? There's no single answer. Some couples find it saves time; others get quotes that land exactly on the number. Decide together, and tell Claude in the template.

Logging replies

When replies come in, get them into the sheet the same day. With Gmail connected:

Search my email for replies from the vendors in our Vendors tab since [date]. For each reply, give me the Outreach rows (date, vendor ID, vendor, "Received", "Email", summary, what they asked us for, reply needed yes or no) and any changes to the Vendors tab (stage, last contact, next action, next action due). List the edits; don't make them yet.

One gap to know about: through Gmail, Claude sees that an email has attachments, but it can't open them. Quotes and contracts usually arrive as PDFs. Download them, save them to the shared contracts folder, and add them to a chat.

A follow-up rhythm

Pick one number of working days you'll wait before following up, and write it in the Details tab. The workbook starts at five; that's a default, not a rule. The Outreach tab works out each follow-up date from it, and the Overview counts the ones that are due.

A rhythm that works for a lot of people:

• Follow up once after your waiting period.
• If there's still nothing after a second period, mark the vendor "Passed" unless they're your first choice. A slow reply now is often a slow reply later.
• For a first choice, try a phone call instead of a third email.

Comparing quotes

Quotes never arrive in the same shape. One is per head, one is a package, one has a service charge and one says gratuity is "at your discretion". Comparing the headline numbers is how couples end up over budget.

The Quotes tab forces like for like: base price, fees and service charge, tax, any tips not already included, and a total that adds them up. Also deposit, whether it's refundable, the payment schedule, what's included, what isn't, and the cancellation and date-change terms. Zola notes that vendors usually ask for a non-refundable retainer or deposit to hold your date, so the refundable column matters.

Here are three catering quotes (attached). Put each into our Quotes tab columns. Use only numbers that appear in the quote. Where a cost isn't stated (tax, service charge, staffing, cake cutting, corkage), write "not stated" rather than guessing. Then list what's included in one quote but not the others, and draft the questions we'd need answered to compare them fairly.

Two things to remember:

• The cheapest total isn't the cheapest choice if it leaves out staff, or rentals you'll then pay for elsewhere. Ask Claude what each quote leaves for you to buy separately.
• Pay deposits by credit card where you can. The BBB, Ohio's attorney general and Consumer Reports all say so, and chapter 8 explains why. Don't pay the whole fee up front.