How to Remind Someone to Pay You: Professional Tips That Actually Work

Asking for money that’s owed to you can be downright uncomfortable. Whether you’re a freelancer waiting on payment from a client or you loaned money to a friend who seems to have developed sudden amnesia, knowing how to remind someone to pay you is an essential skill that most of us were never taught.

I’ve been in the trenches with thousands of freelancers for over a decade, and the one thing that consistently separates successful freelancers from struggling ones is their ability to get paid consistently and on time.

The good news? Reminding someone to pay you doesn’t have to be awkward, confrontational, or damage your relationship. With the right approach, you can maintain professionalism, preserve relationships, and most importantly, get paid what you’re owed.

In this comprehensive guide, I’ll share battle-tested strategies for reminding people to pay you that are both effective and professional. These approaches work whether you’re dealing with clients, friends, or family members who owe you money.

Why Asking for Payment Is So Uncomfortable (But Necessary)

Before diving into the tactics, let’s address the elephant in the room: why is asking for money that’s rightfully yours so darn uncomfortable?

Most of us were raised to believe that talking about money is taboo. We worry that asking for payment will make us seem needy, greedy, or untrusting. These cultural hang-ups make it difficult to have straightforward conversations about money—even when someone legitimately owes us.

But here’s the truth: there’s nothing wrong with expecting to be paid for your work or having a loan repaid. In fact, clear communication about payment is the foundation of healthy professional relationships and even personal ones.

Remember: you provided a service or loaned money in good faith. The discomfort should be on the person who hasn’t fulfilled their end of the agreement—not on you for bringing it up.

13 Professional Ways to Remind Someone to Pay You

Let’s get into the specific strategies that will help you collect what’s owed to you while maintaining your dignity and relationships.

1. Be Clear About Payment Terms From the Start

The best payment reminder is the one you never have to send. Setting crystal-clear expectations upfront is your first line of defense against payment issues.

For freelancers and business owners, this means:

• Having a written contract that specifies payment amounts and due dates
• Clearly outlining your payment terms (Net 15, Net 30, etc.)
• Defining consequences for late payments (interest, late fees, etc.)
• Specifying acceptable payment methods

For personal loans, even between friends or family:

• Agree on repayment terms before lending money
• Consider putting the agreement in writing (even a simple text)
• Be specific about when you expect to be repaid

When everyone understands the expectations from day one, you dramatically reduce the likelihood of awkward payment conversations later.

2. Send a Friendly Initial Reminder

When the payment due date approaches (or has just passed), a gentle reminder is often all that’s needed. Most people aren’t deliberately avoiding payment—they simply forgot or got busy.

Your first reminder should be light, friendly, and give the benefit of the doubt. Here’s a template you can adapt:

For clients:

“Hi [Name], I hope you’re doing well! Just a friendly reminder that invoice #12345 for [amount] is due today. I’ve attached it again for your convenience. Let me know if you have any questions!”

For friends/family:

“Hey [Name]! Hope everything’s going great. I just wanted to check in about the [amount] I loaned you last month. No rush, but I wanted to see when you might be able to pay it back. Thanks!”

Notice how both examples maintain a positive tone while clearly stating what’s owed. This approach works surprisingly well—often, you’ll get paid immediately after sending this kind of reminder.

3. Use Automation to Your Advantage

For freelancers and business owners, one of the best investments you can make is in a system that automates payment reminders. This takes the emotional element out of the equation and ensures consistent follow-up.

Tools like Moxie, Bonsai, FreshBooks, and HoneyBook can automatically send payment reminders before and after due dates without you having to think about it. If you’re thinking about using a lead generation tool for freelancers that also helps with this, SolidGigs offers not only job leads but resources to help you manage client relationships, including payment collection.

Automation is powerful because:

• It removes the personal discomfort of sending reminders
• It ensures consistent timing and messaging
• It gives clients multiple opportunities to pay
• It creates a paper trail of your payment requests

Setting up a sequence (7 days before due, on the due date, 7 days after, etc.) means you only have to personally step in for truly problematic situations.

4. Make It Ridiculously Easy to Pay You

Sometimes payment delays have nothing to do with willingness to pay—they’re about friction in the payment process. The harder it is to pay you, the longer it will take.

Offer multiple payment options like:

• Credit/debit card payments
• Bank transfers or ACH
• Payment apps (Venmo, PayPal, Cash App, etc.)
• Online payment portals

For clients, include a “Pay Now” button directly in your emails and invoices. For personal payments, send a direct payment request through your preferred app.

I’ve seen freelancers cut their average payment time in half simply by making it easier for clients to pay them. Don’t underestimate the power of convenience!

5. Reference Previous Conversations

If your initial reminder doesn’t work, your next approach should reference previous communications. This gently reminds the person that this isn’t your first attempt to collect payment.

For example:

“Hi [Name], I wanted to follow up on my email from last week about invoice #12345 for [amount], which was due on [date]. I haven’t received payment yet, so I wanted to check if you had any questions or concerns about the invoice.”

This approach accomplishes a few things:

• It shows you’re keeping track of the situation
• It reminds them this is a repeated request
• It gives them an opportunity to explain any legitimate issues
• It maintains professionalism without being aggressive

6. Ask If There’s a Problem You Can Help With

Sometimes people avoid paying because they’re experiencing legitimate financial difficulties or have concerns about the product/service. Approaching the situation with empathy can open up communication.

Try something like:

“I notice the payment is still pending, and I wanted to check if everything is okay. If you’re having any issues with the invoice or need to discuss alternative arrangements, please let me know. I’m happy to work with you to find a solution.”

This approach:

• Shows your willingness to be flexible
• Gives them an opening to express concerns
• Positions you as a problem-solver rather than a debt collector
• Can preserve the relationship even in difficult circumstances

7. Be Direct About Consequences (Respectfully)

If friendlier approaches haven’t worked, it’s appropriate to clearly communicate the consequences of continued non-payment. This isn’t about threats—it’s about transparency regarding what happens next.

For freelancers/businesses:

“I wanted to remind you that according to our agreement, invoices past 30 days are subject to a 5% late fee. Your invoice is currently 25 days past due. To avoid additional charges, please submit payment by [date].”

For personal loans:

“I’ve reached out several times about the [amount] I loaned you. I value our relationship, but I need to be clear that I’m counting on this repayment. Can we agree on a date when you’ll be able to pay this back?”

The key is stating consequences factually without emotional language. This maintains professionalism while making the situation clear.

8. Switch Communication Channels

If email reminders aren’t getting results, try a different communication method. People respond differently to various forms of outreach:

• If you’ve been emailing, try a phone call
• If you’ve been texting, try an in-person conversation
• If you’ve been calling, try a formal letter

Sometimes, a simple channel switch can yield immediate results. I’ve seen cases where a client ignored multiple emails but paid within hours after a brief phone call.

The change in medium creates a pattern interrupt that can break through avoidance behaviors and lead to action.

9. Offer a Payment Plan

If you suspect financial hardship is behind the delayed payment, proactively offering a payment plan can be a win-win solution. This shows flexibility while still ensuring you get paid.

“I understand that making the full payment of [amount] might be difficult right now. Would it help if we set up a payment plan? Perhaps we could divide it into three monthly payments of [amount].”

This approach:

• Shows empathy for their situation
• Offers a practical solution
• Makes repayment seem more manageable
• Can preserve the relationship while still ensuring you get paid

10. Use Positive Reinforcement

Highlighting the benefits of payment rather than the negatives of non-payment can be surprisingly effective. People generally respond better to positive framing.

For clients:

“Settling this invoice will allow us to move forward with the next phase of the project, which I’m really excited about. I have some great ideas for [specific benefit] that I can’t wait to implement once we’ve closed out this current phase.”

For personal loans:

“Once we get this settled, I’d love to treat you to dinner to celebrate [something positive in their life]. Let me know when works for you to take care of this so we can plan that!”

11. Be Strategic With Timing

The timing of your payment reminders can significantly impact their effectiveness. Consider factors like:

• Send business reminders early in the week (Tuesday-Thursday)
• Send during business hours (ideally mid-morning)
• For personal loans, consider when the person might have just been paid
• Avoid holidays or known stressful periods

Smart timing increases the likelihood that your reminder will be seen and acted upon rather than ignored or forgotten.

12. Use Social Pressure (Carefully)

This approach requires sensitivity but can be effective in certain situations, particularly with personal loans. The idea is to create a scenario where social expectations encourage payment.

For example, if you’re planning a group activity with the person who owes you money:

“Looking forward to seeing you at [event]! By the way, if you could repay the [amount] before then, I can use it toward my share of the [group expense].”

This creates gentle social pressure without public embarrassment. The key is subtlety—you’re simply reminding them in a context where fulfilling obligations is the social norm.

13. Consider a Final Notice Before Escalation

If all else fails, send a formal final notice before taking more serious measures like collections or small claims court. This gives the person one last opportunity to resolve the situation amicably.

“This is a final notice regarding the outstanding payment of [amount] that was due on [date]. Despite multiple reminders, payment remains overdue. To avoid further action, please submit payment by [date—typically 7-10 days from notice]. After this date, I will unfortunately need to [specific next step—collections, legal action, etc.].”

This communication should be formal and sent via a trackable method (email with read receipt, certified mail, etc.). The goal is to convey the seriousness of the situation while still providing an opportunity for resolution.

Crafting the Perfect Payment Reminder Email

Now that we’ve covered general strategies, let’s look at how to craft an effective payment reminder email. The best reminders include several key elements:

Clear Subject Line

Make it impossible to ignore what your email is about with subjects like:

• “Invoice #12345 Payment Reminder – Due April 15”
• “Friendly Reminder: Payment Due Tomorrow”
• “Outstanding Balance: Follow-up on Recent Invoice”

Polite Greeting

Always start with a friendly salutation, regardless of how frustrated you might feel.

Invoice Details

Clearly state:

• Invoice number/reference
• Amount due
• Original due date
• How many days overdue (if applicable)

Clear Request

Explicitly state what action you want them to take and by when.

Payment Methods

Remind them how they can pay you, with direct links when possible.

Next Steps

Outline what happens after they pay or if they don’t pay by your specified date.

Professional Closing

End on a positive note with your contact information.

Sample Payment Reminder Email Templates

Here are three templates you can adapt for different stages of the payment reminder process:

Template 1: First Reminder (Before Due Date)

Subject: Friendly Reminder: Invoice #12345 Due on Friday

Hi [Name],

I hope this email finds you well! This is a friendly reminder that invoice #12345 for [amount] is due this Friday, April 15th.

For your convenience, I’ve attached the invoice again. You can make payment through any of these methods:

• Credit card: Click the “Pay Now” button on the invoice
• Bank transfer: Using the account details on the invoice
• PayPal: Send to [email address]

If you have any questions or need any clarification about the invoice, please don’t hesitate to reach out.

Thank you for your business!

Best regards,

[Your Name]

Template 2: Second Reminder (Shortly After Due Date)

Subject: Invoice #12345 Payment Now Due

Hi [Name],

I hope you’re doing well. I wanted to follow up on invoice #12345 for [amount], which was due on April 15th.

My records show that this payment is still pending. If you’ve already sent the payment, please disregard this message and accept my thanks.

If not, I’d appreciate it if you could take care of this at your earliest convenience. You can pay directly through the invoice using the “Pay Now” button or via any of the payment methods listed on the invoice.

Please let me know if you have any questions or if there’s anything I can do to help facilitate the payment process.

Thank you for your attention to this matter.

Best regards,

[Your Name]

Template 3: Final Reminder (Significantly Past Due)

Subject: URGENT: Outstanding Payment for Invoice #12345

Hi [Name],

I hope this email finds you well. I’m writing regarding invoice #12345 for [amount], which was due on April 15th and is now 30 days overdue.

I’ve sent several reminders about this outstanding payment, but I haven’t received a response or payment yet. According to our agreement, invoices past 30 days are subject to a [percentage]% late fee, which has now been applied.

The current amount due, including the late fee, is [updated amount].

I value our business relationship and would like to resolve this matter amicably. Please submit payment by [date—typically 5-7 days from now] to avoid further action.

If you’re experiencing financial difficulties or have concerns about the invoice, please contact me immediately so we can discuss possible solutions.

Thank you for your prompt attention to this matter.

Best regards,

[Your Name]

Special Considerations for Different Relationships

The strategies for reminding someone to pay you may vary depending on the nature of your relationship. Let’s look at some specific considerations for different scenarios:

Clients (Professional Relationships)

With clients, maintaining professionalism is key. Your approach should be:

• Consistent with your brand and previous communications
• Referenced to contractual agreements and terms
• Focused on the business relationship rather than personal aspects
• Systematic, with escalating formality as needed

The SolidGigs community has found that using a software platform to standardize your payment process with clients can dramatically reduce payment issues. When clients see that you have professional systems in place, they tend to take payment obligations more seriously.

Friends and Family

When dealing with friends or family members, the emotional stakes are higher. Consider these approaches:

• Have the conversation in person when possible
• Focus on the impact the delayed payment has on you
• Be open to hearing their circumstances
• Consider whether the relationship is worth more than the money
• Be clear about whether this affects your willingness to lend in the future

Remember: Money issues are one of the leading causes of damaged personal relationships. Sometimes it’s better to mentally write off a loan to a friend or family member than to damage the relationship irreparably—but that’s a personal decision only you can make.

Service Providers or Contractors

If you need to remind someone who works for you about payment terms:

• Reference your agreement or contract
• Ask if they need any additional information from you
• Set clear expectations about when you’ll resolve the issue
• Follow through on your commitments

Preventative Measures to Avoid Payment Issues

As the saying goes, an ounce of prevention is worth a pound of cure. Here are some strategies to reduce the likelihood of having to chase payments in the first place:

For Freelancers and Business Owners:

• Require deposits before starting work. A 50% upfront payment is standard in many industries.
• Use milestone payments for longer projects. Break the project into phases with payment due at completion of each phase.
• Conduct client credit checks for large projects. This can flag potential problem payers before you commit.
• Use contracts with clear payment terms. Include specific due dates and consequences for late payment.
• Consider subscription billing. For ongoing services, automatic recurring payments can eliminate most payment issues.

SolidGigs has found that freelancers who implement these preventative measures report up to 75% fewer late payments than those who don’t.

For Personal Loans:

• Get it in writing. Even a text message or email confirming the loan amount and repayment terms is better than nothing.
• Set specific repayment dates. “When you can” often means “never” in practice.
• Consider using a payment app. Apps like Venmo or PayPal let you send payment requests with specific amounts and notes.
• Be selective about whom you lend to. Past behavior is often the best predictor of future behavior.

When to Stop Trying and Consider Other Options

Despite your best efforts, there may come a point when you need to consider other options for recovering your money. Here are some signs it’s time to explore alternatives:

• Multiple promises to pay have been broken
• The person has become hostile or completely unresponsive
• They’ve explicitly refused to pay
• The relationship has deteriorated to the point of no return
• The stress of pursuing payment is affecting your wellbeing

Depending on the amount owed and the circumstances, your options might include:

• For business debts: Collection agencies, small claims court, or writing off the debt as a business loss for tax purposes
• For personal loans: Small claims court (for larger amounts), or making the difficult decision to forgive the debt for your own peace of mind

Remember that your time and mental health have value too. Sometimes, the cost of continuing to pursue a payment exceeds the value of the payment itself.

Final Thoughts: The Art of Getting Paid What You’re Owed

Learning how to remind someone to pay you effectively is an essential skill in both business and personal finance. The key is finding the balance between persistence and professionalism—being firm enough to get results without damaging important relationships.

For freelancers especially, mastering this skill can be the difference between a thriving business and constant financial stress. The successful freelancers I’ve worked with through SolidGigs have all developed systematic approaches to handling payments that minimize awkwardness while maximizing results.

Remember these core principles:

• Start with clear expectations
• Use a graduated approach, beginning with friendly reminders
• Be consistent and persistent
• Stay professional, even when frustrated
• Know when to compromise and when to stand firm
• Value your own time and mental wellbeing

With these strategies in your toolkit, you’ll be well-equipped to handle even the most challenging payment situations with confidence and professionalism.

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