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The Copy Chick
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Seems very strange. Perhaps the next step is to write a letter (rather than an email.. for some reason it seems more formal) and acknowledge that they have been a really good client for such a long time, which is why you’re a little concerned with recent events.

Perhaps let them know you are willing to discuss payment options if they are having any kind of problems, but if they don’t make arrangement and FOLLOW THROUGH by [X] date, then you will have no other option than to take it to the small claims tribunal.

My past experience in accounts has shown that most of the time people will respond once they get a firm “threat” and more often than not will make payment.

You don’t need to be nasty, but you do need to be specific with dates and firm in your resolution. If they default, you MUST act if that’s what you’ve decided to do.

It’s never pleasant, but sadly it’s sometimes a part of business that must be done.

All the best, however you decide to handle the situation.

Anna