Breaking News & Updates
Let’s be honest about something almost nobody in small business admits out loud: chasing up money is terrifying. Not “public speaking” terrifying, but that low, nagging dread that makes you find literally anything else to do rather than pick up the phone and ask a customer where your payment is.
If that’s you, you’re in very good company — and there’s a much better way than white-knuckling it.
The Fear Is Real — Especially for Tradies
Picture the classic scenario. A tradie — brilliant at the actual work, flat out all week — finishes a big job, sends the invoice, and then… waits.
Thirty days pass.
Then forty-five..
The money hasn’t come in, but the fuel, materials and wages certainly have gone out. And every day the invoice sits unpaid, the thought of ringing the customer gets a little more uncomfortable.
Why is it so hard? Because chasing money tangles up a bunch of very human fears all at once:
The fear of confrontation — nobody wants an awkward, tense conversation.
The fear of seeming desperate — “will they think my business is in trouble?”
The fear of damaging the relationship — especially with a good customer you want more work from. And the fear of just not knowing what to say — so you say nothing, and the invoice ages another week.
It’s not laziness and it’s not bad business sense. It’s completely normal. But left unchecked, it’s also genuinely dangerous — because cash flow, not profit on paper, is what keeps a business alive.
More small businesses are sunk by money they’re owed than by a lack of sales.
The Problem Isn’t You — It’s the Lack of a System
Here’s the reframe that changes everything. The reason chasing money feels so awful is that most people treat every single overdue invoice as a fresh, personal, emotional decision.
- Should I call today?
- What do I say?
- Is it too soon?
- Too pushy?
That mental wrestling match, repeated for every debtor, is exhausting — so it doesn’t happen.
The fix is to stop making it personal and start making it a process. When you have a system — a clear, repeatable set of steps that happen automatically regardless of how you feel that day — the emotion drains out of it. You’re not “confronting a customer.” You’re following a standard procedure that every professional business runs.
The invoice reminder that goes out on day 7 isn’t a personal attack; it’s just what happens on day 7.
A proper credit management system answers all the questions in advance, so you never have to agonise again:
- When does the first friendly reminder go out, and what does it say?
- When does the tone shift from gentle nudge to firm follow-up?
- What are your payment terms, and how do you make them clear before the work even starts?
- How do you record every contact so nothing slips through the cracks? And when do you escalate — and how?
Once those are decided once, chasing money stops being a dreaded decision and becomes a calm routine.
That’s What We Teach
Our Credit Management Course is built around giving you precisely this system. It’s not just which buttons to press in Xero — it’s the whole credit management discipline: sending quotes and invoices, tracking who owes you what, issuing statements to overdue accounts, handling credit notes, and following up in a structured, professional, unemotional way.
You’ll practise it on realistic business scenarios, so by the time you’re doing it for real — in your own business or a client’s — it feels like a routine you’ve run a hundred times, not a terrifying first. That confidence is the whole point:
Because here’s the truth — the business owner who has a system gets paid faster than the one who relies on willpower. Every time.
Or… You Could Just Use a Robot
Now, if even a great system still leaves you wishing you never had to make the call yourself — there’s the other option we wrote about recently. As we covered in our post asking “how would your customers deal with a robot chasing them for money?“, there are now AI services that plug into Xero and literally make the overdue-invoice calls for you: on your script, on your schedule, in a polite voice that never once feels awkward about asking.
It’s a genuinely clever solution to the dread problem, because a robot doesn’t procrastinate and doesn’t lose its nerve. But — as we argued in that post — the smart move isn’t to unleash it on everyone. Money is emotional, and some long-standing customers would be quietly offended to be chased by a machine. The winning approach is judgement: let a tool handle the routine, low-relationship reminders, and keep the delicate ones human.
And notice the catch: to use a robot well, you still need to understand credit management. You have to write the script, set the cadence, decide who’s suitable for automated chasing and who needs a personal touch. In other words, whether you chase the money yourself or hand it to a robot, the underlying skill is the same — you need to understand the system.
The Bottom Line
Chasing money will always feel uncomfortable if you’re making it up as you go. Give yourself a system and the fear largely disappears, because you’re no longer deciding — you’re just following the steps. Learn that system properly and you’ll protect the cash flow that keeps every business alive, whether you’re running your own or doing the books for someone else.
Master the skill first. Then decide whether you make the calls, or your robot does.
Ready to stop dreading the follow-up? Explore Course 512 and our full range at https://bookkeepercourse.com.au
-- Did you like what you read? Want to receive these posts via email when they are published? Subscribe below.