Get paid without the awkward chase

By Jason Sibley

The problem

You did the work. You sent the invoice. And now, three weeks later, you're drafting a chasing email for the second time, wondering how firm to be without sounding difficult to work with. This isn't a personal failing — it's one of the most consistently documented problems facing UK small businesses.

Simply Business's SME Insights research found that late payment affects 64% of small business owners, and that UK SMEs were collectively owed an estimated £32.1 billion at one point in 2023, with 30% of businesses owed as much as £45,000 at a time. The government's own consultation on tackling poor payment practices confirms this isn't old news either — it acknowledges late payment as a live policy problem serious enough to warrant new legislation. Simply Business's 2025 report found 29% of small businesses were owed up to £10,000, and tellingly only 3% had actually seen late payments improve since the government's Fair Payment Code launched in December 2024.

What people get wrong

They wait too long before the first follow-up, then over-apologise when they finally send it. The instinct to give clients "a bit more time" before chasing is understandable, but it often means the first reminder arrives well past the point where a polite nudge would have worked, and the tone ends up either resentful or apologetic — neither of which reads as simply professional.

They treat every client the same way. A first-time small client who's three days late needs a different message from a repeat client who's routinely thirty days late. Generic reminder templates, sent identically to everyone, either feel too soft for chronic late payers or too harsh for someone who just missed an email.

They chase manually, which means they chase inconsistently. If following up depends on you remembering to check who owes what, it happens in bursts — usually when cash flow is visibly tight, which is exactly the wrong time to be having your first conversation about an overdue invoice.

They don't distinguish "hasn't seen the invoice" from "is deliberately not paying." These need entirely different approaches, and treating them the same either irritates a client who genuinely missed it, or lets a slow payer coast on your politeness.

They let the discomfort of chasing become a reason to under-invoice or discount upfront. Some small business owners quietly build "probably won't get paid on time anyway" into their pricing, effectively subsidising slow payers rather than fixing the chase itself. This masks the problem instead of solving it, and it's a quiet tax on the business that nobody ever sees written down anywhere.

Why this keeps happening at a structural level

It's worth being clear that this isn't simply about individual businesses being bad at admin. The government's own late payment consultation and the Small Business Commissioner's data point to a structural imbalance: smaller suppliers are frequently paid on the terms set by larger customers, and changing that balance of power is precisely why legislation like the Commercial Payments (Late Payments) Bill exists — to shift incentives at a policy level, not just to remind small businesses to send reminder emails. Knowing this doesn't get your invoice paid faster today, but it's a useful reframe: a slow-paying client isn't necessarily reflecting badly on your business or your invoicing process. Sometimes it's simply reflecting the wider payment culture the government itself is trying to legislate against.

That said, the businesses that get paid fastest, even within this imbalance, tend to be the ones with the most consistent, least emotionally loaded chase process — which is exactly what the three lanes below are designed to build.

A practical frame: three lanes, not one script

Rather than one escalating chase sequence for everyone, sort outstanding invoices into three lanes:

Lane one — just overdue, good history. A short, friendly, automated reminder is enough. This is where AI-assisted tools genuinely shine: most invoicing platforms (see our guide on AI for bookkeeping and invoices) can track payment status and fire off a polite automatic reminder without you lifting a finger, timed to when it's actually gone overdue rather than a fixed weekly schedule.

Lane two — overdue, first time, or a client you value. This is where a short, personal message beats a template, even one drafted with AI help as a starting point. Acknowledge the relationship, ask if there's an issue on their end, and give a clear next step. The tone should assume good faith.

Lane three — chronic late payer, no explanation offered. This is where firmness matters more than politeness, and where knowing your rights matters. The government's late payment reforms exist precisely because chronic late payment by larger customers against smaller suppliers is a recognised structural problem, not just a case of individual bad manners — the Small Business Commissioner's Fair Payment Code exists to name and encourage better-paying businesses, and it's worth knowing it exists as a reference point in a difficult conversation, even though signing up to it is voluntary.

It's worth deciding, in advance and while you're calm, what your actual escalation path looks like for lane three: a firm final email with a specific date, then a phone call, then — depending on the amount and the relationship — a decision about whether to pause further work for that client until the account is settled. Deciding this in the abstract, before you're in the middle of an actual overdue invoice and feeling awkward about it, makes it far easier to follow through consistently rather than freezing up in the moment.

Where AI genuinely helps, and where it doesn't

The mechanical parts of this (tracking which invoices are overdue, by how long, and firing off the lane-one reminder automatically) are exactly what the AI features already built into most invoicing and accounting software (see our guide on AI for bookkeeping and invoices) are designed to do well. This is the least emotionally loaded, highest-value use of AI in the whole chase process, because it removes the need to remember anything at all for the easy cases.

What AI can't do is have the actual difficult phone call, judge whether a client relationship is worth preserving despite a payment problem, or decide when politeness has genuinely run its course. Those are exactly the judgement calls that stay with you in lane two and lane three — AI's role is freeing up the attention you'd otherwise spend on lane one, so you have more of it left for the conversations that actually need a person.

The one decision to make this week

Don't decide "how do I get better at chasing invoices." Decide: which lane does my current list of overdue invoices actually fall into, and am I treating lane one and lane three the same way right now?

For most small businesses, the honest answer is yes — everything gets the same slightly awkward, slightly delayed email regardless of the client or the history. Splitting your outstanding invoices into these three lanes this week, and setting automated reminders for lane one specifically, buys back the emotional energy that's currently going into invoices that never needed a difficult conversation in the first place — leaving your actual attention for the clients who do.

A soft word before you go

If getting paid on time is tangled up with a bigger cash flow or admin problem, My AI Apprentice's SMB AI sessions can help set up the reminder side of this properly, and our AI sales & marketing desk is there if slow payment is really a client-relationship issue in disguise. Entirely optional — the three-lane approach works fine without us.