That awkward follow-up email you dread?

It usually starts with a "missing invoice".

I've been there—delivered a great lesson, the student’s making real progress, and then… radio silence.

No payment.

A week goes by, then two. Suddenly I’m that tutor sending nudgy emails and feeling weird about it.

It took me a while (and a few missteps) to realise that invoicing isn’t just admin—it’s part of my professional rhythm. Once I sorted my system, everything got easier.

Here’s how I now invoice parents without stress or awkwardness.

1. Set expectations from day one

When a new parent or pupil signs up, I make sure they know exactly how invoicing works.

1. I send a welcome email that includes my rate, how often I invoice (monthly), and when payment is due.

Here's an example:

Hi [Parent's Name],

Thanks for signing up for tutoring with me! Here’s a quick overview of how payments work:

• My rate is £40/hour

• I invoice monthly, on the last day of each month

• Invoices are due within 7 days (e.g. by the 7th of the next month)

• Payment can be made by bank transfer (details will be on the invoice)

Let me know if you have any questions. Looking forward to working with [Student's Name]!

Best, [Your Name]

2. I also talk through this in our first chat. I usually say something like:

"Just to keep everything simple, I invoice at the end of each month for all sessions we’ve done. It’ll come by email and includes everything you need. You’ll have a week to pay—easy as that."

It takes two minutes, and saves hours of confusion later.

Of course, you still need to create the invoices in Word or similar, which is a drag.

And you need to email them.

And you still may need to chase but I'll cover that in a second. (I don't chase any more because I automated it, which I'll get to in a sec…)

2. Stick to a regular schedule

I’ve found monthly invoicing works best—for me and for parents. It’s predictable and easy to manage.

• I send invoices on the last day of each month (which was a very admin heavy day - a whole day lost really)

• And my invoices are due within 7 days. That gives families time, but keeps things moving.

• I know when I need to start chasing again as part of my routine. (Or I did…)

No surprises, no delays.

3. Make your invoices simple and clear

Over time, I’ve refined my invoice layout to be crystal clear:

• My name and contact details are right at the top

• Each session is listed with the date, time, and quick summary

• There’s a clear total, and how to pay

I used to do this manually with a template, but honestly...

4. Automation saved me

Manually creating invoices worked fine—until I got busier. I’d forget, or copy-paste the wrong thing. That’s when I started using Tutonomy.

Now, my schedule turns into invoices automatically. Parents get them like clockwork. I can see who’s paid, and I don’t have to chase.

It feels like I hired an assistant—but without the payroll.

5. Following up (without the cringe)

Even with a good system, the odd late payment happens. When it does, I send a polite reminder:

• “Just a quick nudge about last month’s invoice—let me know if you need me to resend it.”

Short, friendly, and assumes the best. That tone has worked every time.

Admin used to feel like a slog—but it doesn’t have to.

Once I got my invoicing sorted, everything felt smoother. Parents appreciated the clarity. I appreciated not dreading the first of the month.

If you want invoicing that just runs itself, give Tutonomy a try. It’s made a huge difference to how I run my tutoring business.

— James