Invoice Chasing

Chasing Overdue Invoices Without Damaging Client Relationships

Jan 5, 2026

10 mins read

Let's talk about the thing nobody wants to do.

Chasing money you've already earned.

You completed the work. Delivered the value. Sent the invoice. And now... nothing.

The invoice is sitting there. 14 days overdue. Then 21 days. Then 30.

And you're sitting there thinking:

"Do I follow up again? Will I seem pushy? What if they get annoyed and never work with me again?"

I've watched this play out hundreds of times over the past 15 years.

Business owners who would rather lose money than risk seeming "difficult" about payment.

They'll chase a client once, maybe twice, and then just... stop.

Because it feels uncomfortable and they don't want to damage the relationship.

Here's what I need you to understand:

A client who gets angry at you for asking to be paid for work you completed isn't a client worth keeping.

And a good client? They won't get angry. They'll apologise for forgetting and pay you.

This guide is about how to chase overdue invoices professionally, persistently, and without burning bridges with the clients who actually matter.

Why Chasing Invoices Feels So Uncomfortable

Before we get into the how, let's talk about the why.

Why does chasing invoices feel so awkward?

I've asked dozens of business owners this question, and here's what they tell me:

"I don't want to seem desperate."

You're not desperate. You're a professional asking to be paid for work you completed. There's a difference.

"What if they think I don't trust them?"

You're not saying you don't trust them. You're following up on an overdue payment. That's normal business behaviour.

"I'm worried they'll get annoyed and not hire me again."

If a client gets genuinely angry at you for professionally following up on payment, they were going to be a payment problem anyway. You've just found out sooner.

"It feels like I'm begging for money I already earned."

This one hits hard because it's exactly how it feels sometimes.

But here's the reframe:

You're not begging. You're collecting. There's a massive difference.

Begging is asking for something you're not entitled to. Collecting is asking for something you've already earned.

The discomfort you feel? That's just social conditioning telling you that talking about money is impolite.

But this isn't a dinner party. This is business.

And in business, asking to be paid is not just acceptable - it's expected.

The Psychology of Why Clients Pay Late (And Why It Matters)

Here's something that changed how I think about chasing invoices:

Most clients who pay late aren't trying to screw you over.

I know that's hard to believe when you're staring at a 60-day overdue invoice wondering how you'll make payroll.

But I've talked to enough business owners on both sides of this to know the truth.

In most cases, late payment falls into one of these categories:

They genuinely forgot (30-40% of cases)

Your client is busy. They've got their own fires to put out. Your invoice arrived, they meant to pay it, and then... life happened. It got buried under 147 other emails. They forgot.

This is why a simple, friendly reminder often works immediately. They're not avoiding payment - they just forgot.

The invoice got lost (20% of cases)

It went to spam. It went to the wrong person. It got filed in the wrong folder. They never actually saw it.

This is why including the invoice link in every follow-up matters. You're making it easy for them to find it and pay.

Cash flow issues on their end (20-30% of cases)

They want to pay you. They're planning to pay you. They're just waiting to get paid themselves.

This is why offering payment plans can work. They're not trying to avoid payment - they're just stuck in their own cash flow cycle.

There's an issue with the invoice or the work (10% of cases)

Something doesn't add up. The amount seems wrong. There's a dispute about the scope. But they haven't told you yet because confrontation is uncomfortable.

This is why asking "Is there an issue with the invoice?" in your follow-ups matters. You're giving them permission to raise concerns.

They're deliberately stalling (less than 10% of cases)

The actual bad actors who are trying to avoid payment or see how long they can stretch it.

These are the ones you need to escalate quickly. But they're the minority.

Why does this matter when you're chasing invoices?

Because your approach should match the situation.

If someone genuinely forgot, a friendly reminder works perfectly.

If someone's deliberately stalling, you need to be much firmer much faster.

The problem is, you don't always know which situation you're in until you start the chase.

That's why the progressive approach works so well.

The Progressive Chase System (Days 1-35)

The best way to chase overdue invoices without damaging relationships is to escalate gradually.

Start friendly. Get progressively firmer. Know when to stop.

Here's the timeline that actually works:

Days 1-7: The Friendly Reminder

At this stage, assume they forgot. Keep it casual and helpful.

"Hi [Name], hope you're well! Looks like this invoice is now overdue. Would you mind giving it a quick look and letting me know? Here's the link for your convenience."

You're not accusing them of anything. You're just... checking in.

Most clients will respond immediately with:

"Oh my god, sorry, paying now."

If they don't respond within 2-3 days, move to the next stage.

Days 8-14: The Professional Check-In

Still polite, but you're acknowledging that time has passed.

"Hi [Name], just following up on this invoice. Am here to help if anything is unclear."

Notice what you're doing here: you're offering support. Maybe there's an issue with the invoice. Maybe they have questions. You're making it easy for them to engage.

If you get a response like:

"Sorry, dealing with cash flow issues, can we set up a payment plan?"

Great job, you've opened dialogue.

If you get nothing, wait another week and move to the next stage.

Days 15-21: The Direct Request

Time to drop the excessive politeness.

"Hey [Name], still waiting on this one. Can you give me an update either way?"

See the shift? You're not asking if there's an issue. You're asking for an update.

You need communication, even if it's bad news.

The phrase "either way" is important. You're making it clear that you need a response regardless of whether they can pay immediately or not.

Days 22-28: The Firm Professional Push

This is your last email before you pick up the phone.

"Hi [Name], unfortunately, this one has been outstanding for a while now. Are you able to sort this out today? I've got the link for you here. Let me know if there's anything I can do to help."

Even at this stage, you're still professional. You're still offering to help. But you're also making it very clear that this needs to be resolved.

Days 29-35: Time for the Phone Call

If someone hasn't responded to four progressively firmer emails over four weeks, another email isn't going to change anything.

Pick up the phone.

Not an angry call. Not a collections call. A professional, "what's going on?" call.

The Art of the Follow-Up Phone Call

Here's the uncomfortable truth: sometimes you need to actually call them.

But most business owners avoid phone calls because they don't know what to say.

Here's exactly what to say:

Opening:

"Hi [Name], it's [Your Name] from [Your Company]. I'm calling about invoice #12345 that's been outstanding for about a month now. I've sent a few emails but haven't heard back. Is everything okay?"

Notice what you're doing:

You're stating the facts (invoice outstanding, sent emails)
You're not being aggressive
You're asking if everything's okay (showing concern, not anger)

If they apologise and say they forgot: "No worries at all, these things happen. Are you able to process payment today? I can resend the invoice if that helps."

Make it easy. Don't make them feel bad. Just get paid.

If they mention cash flow issues:

"I understand. Would a payment plan help? We could break this into three payments over the next 60 days?"

Offer solutions. Don't just demand payment.

If they mention an issue with the invoice or work:

"Okay, let's sort that out. What specifically is the issue? I want to make sure we resolve this properly."

This is why the phone call matters.

You can actually have a conversation and resolve disputes that would take 10 emails back and forth.

If they're evasive or hostile:

"I understand you're busy, but I need to know when this will be paid. Can you commit to a date?"

If they still won't commit or they're deliberately avoiding the conversation, you've learned something important: this is a problem client, and you need to escalate.

The phone call usually results in one of three outcomes:

They forgot, they apologise, they pay immediately (most common)
They explain the issue, you work out a solution (second most common)
They're evasive, hostile, or non-committal (red flag - escalate)

When to Escalate (And When to Walk Away)

Not every invoice is worth chasing forever.

At some point, you need to make a decision: escalate to collections/legal action, or write it off and move on.

Here's how to decide:

Escalate to Debt Collection If:

The amount is over $1,000
You've tried everything else (emails, calls, payment plans)
The client is deliberately avoiding payment
You have clear documentation (invoice, terms, proof of delivery)

Debt collectors work on commission (typically 25-40% of what they collect), so it costs you nothing upfront. If they collect, you get 60-75% of what you're owed. If they don't, you're no worse off.

Consider Legal Action If:

The amount is significant (over $5,000)
You have rock-solid documentation
The client is clearly in breach of contract
You're willing to potentially burn the relationship completely

Small claims court is relatively inexpensive ($100-$300 filing fee in most cases) and straightforward for amounts under $10,000. You don't need a solicitor.

But be realistic: legal action is slow, stressful, and there's no guarantee you'll collect even if you win.

Write It Off If:

The amount is small (under $500)
You've spent more time chasing it than the invoice is worth
The client has gone out of business
The chase is damaging your mental health

Sometimes the healthiest thing you can do is write it off, learn from it, tighten your payment terms, and move on.

I watched someone spend six months chasing an $800 invoice. The mental energy it consumed - the anger, the frustration, the sense of injustice - was eating them alive.

I asked them:

"If I offered you $100 right now to forget about this and move on, would you take it?"

They said yes immediately.

That's when they realised the invoice had become about principle, not money.

And principle is expensive.

How to Chase Without Damaging Good Relationships

Here's the thing that matters most:

Good clients don't get angry when you chase payment professionally.

They apologise for forgetting and they pay.

The clients who get angry, defensive, or hostile when you follow up on payment?

They were going to be problems anyway. You've just found out sooner.

So how do you chase invoices without damaging relationships with the clients who actually matter?

In short:

Be professional, not personal.
Just state the facts
Escalate gradually, not immediately.
Make it easy for them to pay.
Offer solutions, not ultimatums.
Know the difference between forgetfulness and avoidance.
Keep detailed records.
Set boundaries and stick to them.
Don't work for free while chasing payment.

The Automation Solution (Because Manual Chasing Is Exhausting)

Here's the reality of chasing invoices manually:

You won't do it consistently.
You'll remember some invoices. You'll forget others.
You'll feel awkward about following up with certain clients, so you'll let it slide.
You'll get busy with actual work and think "I'll chase them next week."
Next week becomes next month.

This is exactly why systematic follow-up matters so much.

And why I built Invoice Nudge.

It automatically:

Monitors your Xero or QuickBooks for overdue invoices
Creates follow-up drafts that appear in your Gmail or Outlook
Checks your email history to make sure you haven't already discussed the invoice
Escalates appropriately based on how many days overdue

You just review the drafts (takes 10 seconds), adjust if needed, and send from your own email address.

Not from "noreply@xero.com" that clients ignore. From you.

One of our users (a marketing agency) recovered 3 out of 5 overdue invoices last week. $7,950 collected.

Another user (a legal firm) recovered 5 out of 9 overdue invoices. $13,217.

The follow-ups came from their actual email addresses.

The clients responded because they looked like real follow-ups from real people.

Because they were.

But whether you use Invoice Nudge or do it manually, the key is this:

Consistent follow-up is the difference between collecting 5% of overdue invoices (via generic reminders) and collecting up to 64%.

Common Mistakes When Chasing Invoices

Let me show you what NOT to do, because I've seen these mistakes destroy relationships and still not recover the money.

Mistake 1: Being too apologetic

"I'm so sorry to bother you about this, I know you're busy, but if you possibly have a moment..."

Stop apologising for asking to be paid. You're not bothering them. They owe you money.

Mistake 2: Waiting too long to follow up

"Well, it's only 30 days overdue, I'll give them another couple of weeks..."

The longer you wait, the less likely you are to get paid. Follow up at Day 7. Not Day 30.

Mistake 3: Getting emotional

"I'm a small business owner and unpaid invoices really hurt my cash flow..."

Your client doesn't owe you their sympathy. They owe you money. Keep it professional, not personal.

Mistake 4: Threatening too early

"If I don't receive payment by Friday, I'll be taking legal action."

Don't threaten legal action on the first follow-up. Escalate gradually.

Mistake 5: Not following through

"I need payment by Friday or I'll pause ongoing work."

If Friday comes and goes with no payment, and you continue working anyway, you've taught them your boundaries don't matter.

Mistake 6: Sending the same generic follow-up over and over

"Just following up on the invoice I sent. Let me know when you can pay."

This is what automated Xero/QuickBooks reminders do. It doesn't work. You need progressive escalation.

Mistake 7: Giving up too soon

"I've sent two emails and they haven't responded, so I guess they're not going to pay."

Two emails is not enough. Pick up the phone. Be persistent.

Your Action Plan: Start Chasing Properly Today

If you've got overdue invoices sitting in your accounting software right now, here's what to do:

Today:

Pull a report of all overdue invoices
Sort them by days overdue (1-7, 8-14, 15-21, 22-28, 29+)
Send appropriate follow-ups to each (use the templates here)
For anything over 28 days, call them today

This Week:

Set up a recurring Tuesday reminder to check for overdue invoices
Make invoice follow-up part of your weekly routine
Document your follow-up process so it's consistent

This Month:

Review which clients consistently pay late
Tighten payment terms for new clients (shorter payment windows, deposits upfront)
Consider automation so you don't have to manually remember

Long Term:

Stop treating invoice chasing as an emergency that you deal with when cash flow gets tight.

Make it a system that runs every week, automatically, consistently.

The businesses that consistently get paid aren't the ones with the best work or the best clients.

They're the ones with the best systems.

The Bottom Line on Chasing Invoices

Chasing overdue invoices doesn't damage client relationships.

Not chasing them damages your business.

Good clients respond to professional follow-ups with an apology and payment.

Bad clients get defensive, evasive, or hostile.

The follow-up process simply reveals which type of client you're dealing with.

Stop worrying about seeming pushy. Start worrying about not getting paid.

You completed the work and delivered the value.

Go chase it.

Related Resources

Want to dive deeper into invoice collection? Check out these guides:

Tired of chasing invoices manually? Invoice Nudge automates the entire follow-up process. It creates intelligent follow-up drafts that appear directly in your Gmail or Outlook, checks your email history to avoid redundant follow-ups, and escalates appropriately based on days overdue. You review in 10 seconds and send from your own email address. Start your 14-day free trial - setup takes 3 minutes.