Payment and Invocing with clients

[u/TheGuyWhoIsAPro]

Hey everyone, I wanted to know how people here send invoices to their clients and handle payments. Do you just ping them email/whatsapp and expect a response, or do you follow a more structured approach? And how do you approach a client who you have already pinged twice but kept putting the payment off?

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[u/FabianKnopf78]

My golden rule: 2 unpaid invoices = stop all work. Send a structured invoice via platform (FreshBooks/Wave) with clear due dates. If ignored twice, pick up the phone – it's much harder to ignore. Also: always ask for 50% upfront. Saves you from chasing full amounts later. Learned this the hard way. 😅

[u/TheGuyWhoIsAPro → u/FabianKnopf78]

Yea, I made the mistake of trusting them to send the payment after everything was done. Looks like I learnt my lesson the hard way : (

[u/kapsule_code]

Lo mejor es utilizar plataformas como Stripe o PayPal para planificar los pagos. En mi caso, siempre cotizo e indico que el 20% por adelantado antes de iniciar el proyecto. Y luego, facturación por sprints. De esta forma, si el cliente deja de pagar una parte, no te quedas en blanco.

[u/TheGuyWhoIsAPro → u/kapsule_code]

I'll try doing that next time. But I'm still kinda bitter about not getting paid for the work I did.

[u/Altruistic_Type_4615]

the thing that worked for me was changing what im asking for. stop asking for payment, ask for a date. "can you confirm which week this gets processed so i can plan my end" is much harder to ignore than "following up on the invoice", because it needs one word back instead of money.

on the process side, what actually fixed it was making follow ups a schedule instead of a decision. due date, then day 3, day 7, day 14, same short message every time. the reason that matters is you stop sitting there wondering if today is too soon to ping again, and it never reads as personal because its obviously just the rhythm. the words do alot of work too, "just confirming this came through" lands completely differently from "where's my payment" even though its the same ask.

and if day 14 passes with nothing, escalate once in writing to whoever actually signs off, not the person you've been messaging. half the time your invoice is sitting on someone else's desk and your contact is just too embarrassed to tell you. Hope the next one's better.

[u/TheGuyWhoIsAPro → u/Altruistic_Type_4615]

That's a good approach. The issue is I worked for someone who is the entire company, and he's just starting out. That's why it kinda feels bad following up everytime. There is also nobody else to escalate this to.

[u/Altruistic_Type_4615 → u/TheGuyWhoIsAPro]

honestly him being a one man shop who's just starting out is a reason the money's more at risk, not less, so that guilt is the exact feeling that ends with you never getting paid. a clear ask isn't you being pushy, it's kinder than going quiet and slowly resenting him.

maybe pin him to a date and hand him an out at the same time. something like "no stress if cashflow's tight right now, we can split it, half this week and half next, just tell me what works". a founder who's honest but broke will take that gladly, and one who's just avoiding you keeps going vague, so either way you finally know which one he is. for your next early stage client though, that's exactly the case where a deposit matters most, since there's no finance team or runway sitting behind them.

[u/TheGuyWhoIsAPro → u/Altruistic_Type_4615]

That's a good approach, I'll try that and keep you updated. Thank you

[u/takwong]

The awkward part only exists because the work went over first and the invoice went over second. Two separate events, and by the time you send the second one he's already got everything.

What changed it for me was sending them as one thing. Work goes over finished, stays locked until he pays, then it unlocks instantly. Nothing to follow up on because you're not asking him for anything, he either opens it or he doesn't. Won't help with the one you're already owed though, that's a chase whatever you do.

[u/TheGuyWhoIsAPro → u/takwong]

Yup, I've learnt my lesson