Need tax filing help and guidance? We’ve got you covered. Click here to learn more.

You know that invoicing is more than just a simple financial transaction. It’s an integral part of your business that drives your cash flow, and ultimately, your success. But too many small business owners get hung upon the question of: ‘exactly when should I send my invoices?’ And frankly, there is no right answer to this question. So today, we’re going to run through some of your options when it comes to sending invoices. Our hope is that when we are done, you’ll be able to implement some rules and systems to help you streamline your invoicing process. 

When should I send my invoices?

When should I send my invoices?

Let’s start with the lowest-hanging fruit. For most small businesses, the most obvious time to send an invoice is immediately upon service completion or product delivery. 

The benefit of invoicing quickly is that your business, service, or product, will still be fresh in the mind of your client! It will also be easier for them to reconcile the bill they’ve just received since they’re likely still thinking about the work that was just completed! Of course, we’d be remiss to not mention that you should always follow up with your customer to make sure they are satisfied with the work they’ve received! But once that’s all clear, feel free to send that invoice! 

For more complex, expensive, or time-intensive projects, consider requesting payment, or partial payment, up front. This one’s straightforward: if you’re billing for a very expensive project, you’ll want to be sure that the client is just as serious about the work as you are. So before you get going on plans, supplies, and budgets, give yourself some peace of mind and make sure your client is on the same page with advance payments!

For more complex projects that you are hesitant about requesting up-front payment for, consider billing your clients at agreed-upon milestones. For projects that are expected to span 6 months, for example, you’ll want to find billing intervals that make sense for both you and your clients. And we bet you’d be surprised at how much goodwill you can build with clients by determining payment terms ahead of time! So give it a shot – improve your cash flow, your client relationships, and your suite of offerings at the same time!

Lastly, for projects that will be carried out over a recurring and/or extended time-frame, consider repeat invoices at set intervals. Sending your invoices out to longstanding customers, at very specific intervals, will not only limit complexity when it comes to month-end, but it will also guarantee that your customers are never blindsided by a bill they weren’t expecting to receive. Another win-win in the ‘build customer goodwill’ department, if you ask us!

There is truly no one-size-fits-all approach to invoicing. For repeat work, you might consider recurring invoices at a specific, constant interval. For more complex or expensive projects, you might ask for partial payment in advance, or simply bill your client at intervals that work for them. For more straightforward work, or service-oriented work, feel free to issue your invoices immediately after the customer has been served. And never forget to follow-up! Following-up on unpaid invoices is the #1 way to get a payment, so don’t be shy and feel free to send out polite reminders when necessary!

No matter what approach you take, be sure to always keep your eyes on your invoices – both when they were issued, as well as when they were paid. Trust us: your cash flow statement will thank you later! 

download free invoices

Start Your Business

Needing a little guidance when starting a new business?
TrulySmall has you covered.

Did you know that using invoicing software not only helps you to get paid faster but also reduces your invoicing costs by 29%? Start sending invoices free today with TrulySmall Invoices!