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Getting paid over text

Text Customers When It's Their Turn, Not Yours

Learn the only message that never feels pushy: the one that reminds them it's their turn, not the one that suits you.

Yodai · · 4 min read

Text Customers When It's Their Turn, Not Yours

You have their number because they already bought from you. The question isn't whether to text them again, it's what you're going to say that isn't "hey, how's it going?" or a discount dressed up as a greeting. Anyone can spot that in two seconds, and the cost of getting it wrong isn't that they ignore you, it's that they block your number. A customer who bought from you once and blocks you over a useless text is further away than one you never texted at all.

Some businesses never text again, afraid of seeming pushy, and lose half the bookings they could have had without spending a dollar on ads. Other businesses text every week with a deal, and within two months that number stops opening their texts. Both make the same mistake: they decide when to reach out by looking at their own calendar, not the customer's.

The question that filters the message

Before you send anything, ask yourself one question: would this matter to them even if they weren't about to buy anything from me? A message that reminds them of something that's genuinely due passes the filter. A message that only benefits you doesn't.

At a barbershop, "time for a trim" passes the filter: in a month their hair will be long, and they'd be thinking about it anyway. "20% off everything this week" doesn't pass: that only matters to you because Tuesday's slow. The difference isn't in the tone or how friendly the message sounds. It's in whether the reason for reaching out exists outside your cash register.

A calendar reminder or a sales pitch
Calendar reminder
  • Comes from when they'll need it again, not from when it's convenient for you
  • Works just as well the first time as the twentieth
  • Doesn't wear thin: each message arrives when it's due, not when you decide
Sales pitch
  • Comes from your register, not their need
  • The more you repeat it, the less trust it builds, it looks like you can't sell without a discount
  • Works once, not as a habit

Which one to pick: Make the calendar reminder your default message for every repeat customer. Save the sales pitch for someone who's already drifted away completely: there's no cycle left to remind them of, just a one-time, time-limited reason to come back before they forget you.

This isn't just for appointment-based businesses. If you sell something that runs out, a cream that lasts two months, dog food, coffee pods, the product itself sets the cycle: the time to reach out is right before they're about to run out, not before, and not a month after they've already bought it somewhere else because they couldn't find you.

How to stop relying on your memory

Setting up the reminder so you don't have to remember
  1. 1Log the date of every sale
    In a notebook, a spreadsheet, or your order history. Without a date there's no cycle to calculate, and without a cycle all you can do is guess when to reach out.
  2. 2Ask your customers how often they come back
    Don't make it up from behind the counter on a random Monday: if you do haircuts, most people come back every four to six weeks; if it's maintenance physical therapy, every two to three. The trade sets the cycle, not your gut feeling.
  3. 3Reach out when the cycle is up, not before
    If you text someone fifteen days after a haircut that lasts six weeks, you're being annoying. The message only makes sense once they're starting to need what you sold them again.
  4. 4Offer a time slot, not an open question
    "Does Thursday or Friday work for you?" gets answered in a second. "When do you want to come in?" forces them to think, and anything that forces thinking gets put off until it's forgotten.
The message, word for word
Hi Maria, you came in last on July 12 and you usually come back every six weeks, so you're about due. I've got an opening Thursday at 5:00 PM or Friday at 11:00 AM. Let me know which works better and I'll pencil you in.
The costly mistake: texting on your calendar, not theirs
The message that backfires almost always starts on a slow day on your schedule, or at the end of the month when you need cash. It shows: it arrives with no real reason behind it, a deal attached, sent to a customer who still has weeks left of what you sold them. The rule is simple: if the reason to reach out is yours, wait. If it's theirs, send it today.
What you walk away with
  • A test for deciding whether to reach out: would this matter to them even if they weren't about to buy anything?
  • The calendar reminder, not the sales pitch, is your default message for anyone who's already bought from you
  • Two data points per customer are enough: the date of their last purchase and the typical cycle for your trade
  • The message offers a specific time slot instead of asking when works for them

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