What do you about clients who keep paying their bills late, and only after multiple calls and emails?

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Charge them a retainer. Make them replenish before it runs out or you stop work.

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Especially for existing clients. They know your work and presumably benefit from you having positive cash flow and being able to keep the lights on.

There is also the carrot, discount for timely payments, say 3% if bill is paid within 10 business days. I don't think sticks work as well as carrots.

You can do formal retainers or just more frequent billing. You can make clear what your average days outstanding is (this is days in accounts receivable).

One thing that has worked in the past is to send letters to all past due clients saying that your average accounts receivable is X days and that they are at X + y days, which drives up the cost for everyone because you need cash flow and more admin is spent on billing. That if bills were paid within 10 days, rates could be lower etc. This is called behavior nudge and works surprisingly well.

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Sounds like most clients. At least it gets paid

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If the only issue is that they pay late, I prefer that kind of client over a client that will pay sooner but fights about the invoice.

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You need to prepare an employment agreement between you and your client at the beginning of your representation which sets forth billing expectations and your scope of representation. In the agreement include an evergreen and conditions of nonpayment, I.e work paused on case, interest, withdrawing from the case. Even if it is an existing client, you can have them sign an employment agreement which sets forth the expectations.

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An evergreen retainer is good to have, if the client will accept it.

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Do you bill your time for correspondence related to the unpaid bill, checking with accounting on payment status, etc? I’m assuming yes.

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Yes. If it were simply resending the bill. However, if I have to go into details - absolutely.

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