It's really helpful to hear how other small business people and self employed folks deal with asking for money owed!
@ShanaNiederman We use different methods depending on the customer and how long they do not pay. Some we put a hold on their account, then tell them we will not deliver until they pay us at least what is overdue. Then there are others that if we contact them and ask for payment they simply write the check that day and send out. Most commonly, I call and tell them who I am and where I am from and that I noticed that they had some overdue invoices and need to know when to expect the check for payment.
The hard part to remember, is that being paid is an agreed upon part of the transaction. So, I fake it till I make it with confidence. I pretend like it isn't a weird conversation. I ask how they would like to receive their invoice, and discuss with them what their preferred method of payment is. As long as the price was discussed ahead of time, they know this conversation is coming.
Follow up with a statement at 30 days, and beyond. If they are more than 45 days delinquent put a freeze on any services or products sold until they pay. And keep sending invoices until 90. I'd write it off at that point.
To give a little background, I'm a seamstress so I deal with brides on a regular basis, so I'll put it into words that correspond with my business. During the first fitting, I measure and figure out what needs to be done, and then I'll write up an estimate. (it doesn't have to be an "official document", just needs to be in writing.) I show them what I've written up, and ask if they have any questions. I also mention that it's an ESTIMATE, the price may change if there's something that comes up. (ie. an extra alteration needed later) I also ask if that price is reasonable to them. If not, they are welcome to find another place for alterations. If it's reasonable to them, I give them a time frame that it'll be done by and often schedule a follow-up fitting. I also let them know what forms of payment I accept, (I no longer accept checks, I'm too small of a business to go chasing after bounced checks.) and that I accept payment upon completion. I'm a bit awkward, so I usually make a joke saying, "And if you don't pay, you don't get to take your garment home."
When they come for their final fitting they are already aware of approximately how much it's going to cost. So they know that conversation is going to happen. If there's been any kind of change, I tell them what caused the change (additional alterations, or in the case of lower cost, usually less time spent on alterations), and I show them the original copy of the estimate and then the invoice to show on paper what's been changed. Wether or not it's changed, I end up saying something like, "ok, your total is $$, would you like to pay with cash or card?"
If it's a significantly large project that requires me to purchase large quantities of supplies(fabric & notions), I have an agreement written up in addition to the estimate that requires the cost of supplies and 1/2 down for labor before I purchase the supplies. I go over that with them, and have them sign it. If at any point they back out on said large project, I'm already paid up to the work I've done, and I give them whatever supplies I have as well as the product in whatever condition it was in when they backed out. (if that makes sense).
Sorry, this turned out to be kind of a long response.
@HeatherCarver Your response is exactly what I was hoping to learn from Community members. Thanks -- it's super helpful to get walked through all the steps plus the thinking behind them. If I had a wedding dress needs, I'd love to work with someone as upfront and transparent as you, Heather!