The first bill you send to a client is an important milestone, as well as an opportunity to set the tone for your relationship and establish how professional, organized, and reliable your business is.

That first bill communicates a lot about your brand and getting it right can help you avoid misunderstandings and payment delays. A well-crafted bill shows you’re serious about your work and value your client’s time. This helps you build trust, which can lead to more reliable payments. Below, we’ll discuss the key elements you should include in your first bill, common mistakes to avoid, and how Stripe can help simplify the process.

What’s in this article?

• Why is the first bill important?
  
• What information should the first bill include?
  
• How do you set the right tone with the first bill?
  
• How can Stripe help you create your first bill?
  
• What are common mistakes to avoid when billing a client for the first time?
  
• How do you follow up on your first bill?
  
• What should you do if the client disputes the first bill?
  

Why is the first bill important?

The first bill you send to a client sets the tone for your business relationship. It’s your chance to immediately establish that you value professionalism, transparency, and clear communication.

It’s also an opportunity to confirm the details—such as payment terms, due dates, and any agreed rates—so there’s no room for confusion. If your first bill is messy or unclear, it can create unnecessary friction and might affect the client’s perception of your business. This is a widespread problem: a report found that 68% of businesses experience errors on more than 1% of their total invoices. These errors can lead to payment delays and strain client relationships.

What information should the first bill include?

Your first bill is a key touchpoint with your client, so it needs to include the correct details. Your first bill should include the following:

• Your business details: Include your company name, address, and contact information so your client knows exactly where the bill is coming from. Using a logo or branded header is a good way to reinforce your professional image.

• Client’s information: Include the client’s name or company name, address, and contact details.

• Date issued and due date: Clearly state when the bill was issued and when payment is due. Reinforcing payment terms on the bill itself sets expectations for your clients and helps them stay on track.

• Description of services or products: Specify what you’re charging for, whether that’s a product, service, or project. Break it down by the scope of work or hours worked and include the price for each item or service. Provide as much context as possible about the work or products delivered.

How do you set the right tone with the first bill?

Your first bill needs to strike a balance between professionalism and approachability. You want to come across as organized, trustworthy, friendly, and easy to work with. Start by ensuring the bill is clear and well structured.

The language you use on your invoice also helps set the tone. Phrases such as, “Please let us know if you have any questions about this bill,” and, “Payment is due within 30 days. We appreciate your prompt attention,” are polite, firm, and friendly. They set the right expectations without sounding too pushy or too casual.

Consider including a personal touch, such as a brief thank-you message, to show you care about building a good relationship. A well-written, friendly first bill sets the tone for a long-term, positive working partnership.

How can Stripe help you create your first bill?

Once you’ve created your Stripe Invoicing account, you can quickly generate bills and customize them with your logo, company details, and the client’s information.

Stripe also helps automate the process so you can set recurring bills for clients on a regular schedule (e.g., monthly, annually). That means no more manual bill creation for clients with recurring bills.

Your client can pay your bill immediately via credit card, bank transfer, or multiple other methods. Payment options are integrated into the bill itself. After payment is complete, Stripe notifies you that payment was made. It provides a simple way to handle invoicing without getting stuck in paperwork.

What are common mistakes to avoid when billing a client for the first time?

When you bill a client for the first time, there are a few common mistakes to avoid. Here’s what you should remember before you send that first bill:

• Don’t skip the details: It can be tempting to send a bill quickly, but leaving out important info—such as a clear description of services rendered, the agreed payment terms, or your contact details—can cause confusion or delay the payment. Be as specific as possible to avoid misunderstandings.

• Don’t be vague about payment terms: Ensure your client knows exactly when the payment is due and any late fees that might apply after the due date. Clarifying the payment terms helps keep you and your client on the same page.

• Don’t send generic bills: A little warmth can go a long way. Simply saying, “Thank you,” or, “We’re excited to work with you,” adds a personal touch and helps set the right tone for your working relationship.

By avoiding these mistakes, you can set the stage for smooth, timely payments and build a strong, professional relationship with your clients from the start.

How do you follow up on your first bill?

Following up on your first bill might feel awkward, but it’s an important step in ensuring you get paid on time. Start by setting clear expectations about payment terms—when it’s due, how to pay, and what happens if it’s late.

If the due date passes and you haven’t received payment yet, don’t panic. A friendly, polite reminder is usually all it takes. Send a short email or message that thanks your client for their business and gently reminds them that the payment is due. You can say something like, “Just a friendly reminder that payment for bill no. 12,345 is due in the next few days. If you’ve already sent it, please disregard this message. If not, we’d appreciate your prompt attention.”

If it’s been a week or more and you still haven’t received payment, you can follow up again. But this time, you might want to mention your payment terms more explicitly or inquire if there were any issues with the bill. Be firm but polite with a message like, “I noticed we haven’t received payment yet, and I wanted to check in to see if there were any questions or issues with the bill.” Sometimes a bill just gets lost in the shuffle.

What should you do if the client disputes the first bill?

If a client disputes your first bill, stay calm, professional, and communicative. First, listen carefully to their concerns. Whether it’s a misunderstanding about the scope of work, pricing, or payment terms, understanding exactly what they’re disputing is necessary. Ask for specifics to clarify where things went wrong.

Once you know the issue, review the details of the contract or agreement you have with the client. Ensure the bill reflects what was agreed. If it’s a simple mistake, like a wrong price or an overlooked service, admit to it and correct it immediately. If the bill is accurate and the client misunderstands something, take the time to explain it clearly. A polite email or a quick call can clear things up.

If the issue is more complex or involves a misunderstanding that requires negotiation (e.g., billing for additional work not previously agreed to), try to approach it collaboratively. Suggest a solution that works for both parties, whether by adjusting the bill, offering a discount, or implementing a payment plan. The goal is to resolve the dispute while maintaining a positive relationship.

Lastly, document everything—especially any changes or agreements you make during the dispute resolution process. This will help protect you if the issue arises again or in the event of legal action.

Send your first client bill with confidence

Billing your client for the first time is a pivotal moment for your business. A clear, professional bill sets the stage for a smooth working relationship, establishes trust, and helps you get paid on time. By including all the right details, setting the proper tone, and avoiding common mistakes, you make the billing process easier and demonstrate your commitment to professionalism and transparency.

Tools like Stripe can help simplify and automate invoicing, making it easier to stay organized and making the payment process more efficient. If issues arise, handle them with tact and open communication to keep client relations strong.