Writing a "when to send" line
The one sentence that decides whether your assistant ever offers a file — how to write one it can act on, with worked examples for three kinds of business.
Every file in your library carries one line called When to send this. It is a small field and it does more work than anything else on that screen: it is the only thing your assistant reads when deciding whether a file answers what a customer just said.
Not the filename. Not the title. Not the notes. That one line.
⚠️ On WhatsApp and website chat only. Your assistant sends files on those two channels. On Instagram and Messenger it will not offer a file at all — those channels cannot carry one, and your assistant stays quiet about it rather than promising something it cannot deliver.
A file with this line empty is never offered. It is not ranked lower — it is left out of the choice entirely. The library flags every file missing one.
Why the filename is not enough
The obvious design would let the assistant read filenames and pick. It does not work, and the reason is what your own downloads folder looks like:
brochure_v3_FINAL.pdf
WhatsApp Image 2026-08-14 at 4.12.09 PM.jpeg
ceramic.pdf
Scan_20260612_0001.pdfEvery one of those is a real file a real business would want to send. None of them says when. Even a tidy filename only names the contents — and knowing a file is the brochure does not tell anyone the moment to hand it over.
So Kooday asks you for the moment instead, in your own words, once per file.
What a good line looks like
Three rules, in order of how often they matter.
1. Describe the customer’s moment, not the file
The line is matched against what the customer said. Write the thing they say.
| Instead of | Write |
|---|---|
| our brochure | when someone asks what we do, before they book anything |
| price list | when someone asks what it costs, or asks for a written quote |
| T&C document | when a customer asks for the full terms before paying |
| gallery | when someone is unsure the result is worth the money |
2. One moment per file
A line that covers everything matches everything, and an assistant that attaches the price list to a question about parking is worse than one that attaches nothing.
- ✅ when someone asks how ceramic compares to graphene
- ❌ for pricing, terms, comparisons and general questions
If a file genuinely serves two unrelated moments, that is usually two files.
3. Plain language, one sentence
No keywords, no lists of synonyms, no ALL CAPS. It is read as a sentence, so write it as one. Somewhere between five and twenty words is the useful range; anything past a line is being read as a rule and stored as an essay.
Three worked libraries
A car detailing studio
| File | When to send this |
|---|---|
| Ceramic vs graphene | when someone asks which coating to choose, or how ceramic compares to graphene |
| Aftercare instructions | after a booking, when someone asks how to look after the coating |
| Price list | when someone asks what a full detail costs |
| Before and after gallery | when someone is unsure whether it is worth the money |
A tuition centre
| File | When to send this |
|---|---|
| Class timetable | when a parent asks what days and times the classes run |
| Fee structure | when a parent asks about fees or instalments |
| Syllabus overview | when someone asks what is actually covered in the course |
| Admission form | when a parent has decided and asks how to enrol |
A clinic
| File | When to send this |
|---|---|
| Pre-procedure instructions | after an appointment is booked, when someone asks how to prepare |
| Insurance and payment options | when a patient asks whether we accept their insurance |
| Doctor profiles | when someone asks who they will be seeing |
Notice what none of these say: “send this to everyone”, “important”, “always”. A line like that describes your feelings about the file rather than the customer’s moment, and it matches nothing in particular.
Editing one later
Open the file in Files you send and change the line. It takes effect immediately — there is nothing to republish and no cache to wait for.
Changing this line is also the right fix when a file is being offered at the wrong times. Narrow the moment rather than deleting the file.
Troubleshooting
The wrong file gets offered
Two lines are describing overlapping moments. Read them side by side and make the narrower one narrower still — usually one of them has quietly become a catch-all because it lists more than one situation.
Nothing is ever offered in a chat
Check for empty lines first; the library flags them. Then check the channel — on Instagram and Messenger a file is never offered. Then check that the files are In use rather than archived: an archived file is offered on no channel, whatever its line says.
It matches things I did not intend
Long lines are the usual cause. A twelve-word sentence about a single moment behaves better than a forty-word one covering three.
A sensible first pass
Take the last ten conversations where you personally sent a customer a file, and write down the sentence they used just before you sent it. Those sentences are your “when to send” lines, already in the customer’s words — which is the whole thing this field is asking for.
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