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Hello Reader,

A few days ago, I drove past a young girl standing by the side of the road waving a sign that said, "Cookies and pay ID."

Since I like to support kids who are being entrepreneurial, I pulled over, walked back and found out a little bit more about these cookies.

Turns out that the girl and her brother make them with the help of her mom, and they sell them from home every Wednesday, as well as at markets around the territory.

And since this week's batch of cookies were my favourite (chocolate chip), I said,

"That sounds really lovely. I'll have six cookies, thanks."

And the girl looked a bit embarrassed and said,

"Um, well, actually, we only have five."

"That's okay."

"Well, um, one of those five is broken."

"That's okay."

And she brightened slightly and said, "Oh, we'll give you a discount for it."

And then she and her brother promptly got into an argument about how much of a discount I should get, which made me smile.

Anyway, long story short, after settling the amount of the discount, I waited and waited, but nothing was happening.

Confused, I finally asked, "Is somebody getting the cookies?" And she said, "Well, actually, you have to pay first, and then I'll go get them."

"Well, I don't have any cash," I said, somewhat sheepishly.

"That's okay," she smiled. "You can use PayID."

That was a problem. To that point, I had never used PayID. Didn't even really know what it was. I had to get her to explain it to me. And then we tried to get it set up on my phone.

We must have tried 5 or 6 times, but nothing worked. And the one person who could have helped (her mother) was apparently in the shower and currently unavailable to ask.

Just as we were ready to give up, I suddenly realized what the problem was.

After that it was simple. They got their money. I got my cookies and everyone was happy.

And I had a little nibble on the way home. Delicious.

The ending to that little story would have been completely different if we'd given up.

It's true that my waist probably would be a little thinner, but my mouth (and taste buds) would have been much, much sadder.

And a young girl and her brother would have missed out on a sale. I guess it would have been a valuable lesson in some ways, but not anywhere as much fun for any of us.

That little dance with PayID is basically what happens with half the systems in your business too. Something that's meant to be simple hits one weird snag, and it would be so, so easy to just give up on the sale.

So it's worth taking the time to run through your own payment and booking systems the way that girl and I worked through PayID. Not because they'll definitely break. But because knowing where the sticking points are for your customers means you (or whoever's minding the shop) can fix them in two minutes instead of walking away from the sale altogether.

Back to Basics Reminder

Test your payment and checkout systems end to end, the same way you'd want that PayID hiccup caught before a customer hits it. Click through your own invoicing, checkout or booking process as if you were a new customer with no idea how it works. If you get stuck anywhere, that's exactly where a real customer will get stuck too.

A Quick Time-Saving Tip

Use a tool like Zapier (or your AI tool of choice) to connect two systems that currently need you to manually shuffle information between them. If you're not sure where to start, ask ChatGPT or Claude:

That last part matters. Let it ask the questions instead of guessing.

Highlight of the Week

This week's podcast episode is a good one if pricing has ever felt like guesswork. I talked to Per Sjofors (aka The Price Whisperer) about the two questions you can ask 50 potential customers to find your actual pricing range, and why copying a competitor's prices just means following someone else's guess.

He also explained why your cheapest customers might actually be your most expensive ones. Ep. 251: The Two Questions That Take the Guesswork Out of Pricing​

And that's it for this week. Hope you have a lovely weekend.

Trudy

P.S. If you want to stop guessing on pricing, The Price Whisperer: A Holistic Approach to Pricing Power(affiliate link) by Per Sjofors is worth a read. It's the two questions from this week's episode, plus a lot more on why your price tag is doing more work than you think.