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Writer's pictureSkyler Talley

From Asking for Payment to Negotiating a Raise: How to Handle Awkward Money Matters


your client has time to post on social media but cant find your reminder emails

Discussing finances can be uncomfortable, but these conversations are essential for personal and professional growth. Whether you’re asking for a payment, discussing a loan, or negotiating a raise, the key is preparation, empathy, and clear communication. Let’s explore some common awkward financial conversations, how to prepare for them, and strategies to navigate them successfully.


1. Asking for Payment

If you’re a freelancer, small business owner, or contractor, chances are you’ve encountered clients who haven’t paid on time. This can be stressful, especially when it comes to asking for the payment you’ve earned.

How to Prepare:

  • Review your contract: Make sure your agreement includes clear payment terms and deadlines.

  • Give the benefit of the doubt: Before reaching out, assume the delay may be due to an oversight or misunderstanding.

How to Approach It:

  • Start with a polite reminder: Send an email or message with a friendly tone, reminding them of the due date and asking if everything is on track.

    • Example: “Hi [Client], I wanted to follow up on invoice #123, which was due last week. If you need any help processing the payment, please let me know. Thank you!”

  • Be direct if needed: If the polite approach doesn’t work, you may need to be more assertive.

    • Example: “I’d appreciate your prompt attention to this matter. Could you let me know when I can expect payment?”

Tip: Offer flexible payment options (e.g., installments) if appropriate, but make it clear that the balance must be settled.


talking to a brick wall employer for a raise

2. Asking for a Raise or Promotion

Asking for a raise or promotion is one of the most nerve-wracking financial conversations, but it’s a necessary step toward career advancement.

How to Prepare:

  • Gather evidence: Document your achievements, contributions, and the value you’ve added to the company.

  • Research market rates: Know what others in your position are earning to justify your request.

How to Approach It:

  • Choose the right moment: Time your conversation after a significant accomplishment or during your performance review.

  • Start with gratitude: Acknowledge your appreciation for your role and the opportunities you’ve had.

    • Example: “I’ve really enjoyed working on [project] and appreciate the trust you’ve placed in me.”

  • Present your case: Highlight specific achievements and explain why a raise or promotion is justified.

    • Example: “Over the past year, I’ve successfully led [project] and exceeded targets by X%. I believe this contribution warrants a discussion about a salary adjustment.”

Tip: Be open to negotiation, but be clear about your worth and the value you bring to the company.


looks like a fake to me loan denied

3. Denying a Loan Request

Whether it’s a friend, family member, or colleague asking for a loan, denying the request can feel incredibly awkward. However, lending money can strain relationships, especially if the loan isn’t repaid on time.

How to Prepare:

  • Set personal boundaries: Be clear about how much you are willing to lend (if any), and under what circumstances.

  • Consider alternatives: Think of ways to offer help without lending money. For example, you could help them budget or find other financial resources.

How to Approach It:

  • Be empathetic but firm: Acknowledge their situation, but explain your own boundaries.

    • Example: “I understand that things are tough right now, but I’m not in a position to lend money. I hope you can understand.”

  • Offer alternatives: Suggest ways to help without offering financial assistance.

    • Example: “I’m happy to help you explore some budgeting apps or resources that might ease the pressure.”

Tip: Stick to your decision. Lending money you’re not comfortable parting with can harm relationships in the long run.


4. Negotiating Fees or Rates

Whether you’re a service provider or a client, discussing rates can feel uncomfortable, especially when the other party has different expectations.

How to Prepare:

  • Know your value: If you’re the service provider, have a clear idea of what your time and expertise are worth.

  • Research industry standards: If you’re a client, ensure that your rate expectations align with market standards.

How to Approach It:

  • Be transparent: Clearly explain why your rates are what they are. If you’re a client, communicate your budget constraints early.

    • Example (Service provider): “My rate is $X because it reflects the level of expertise and effort required for this project.”

    • Example (Client): “Our budget for this project is $Y. Is there any room for negotiation, or should we adjust the scope?”

Tip: Aim for a win-win situation. Both parties should walk away feeling satisfied with the agreement.


5. Asking for Financial Help

Sometimes, you might be on the other side, needing to ask for financial help from a friend, family member, or even a bank.

How to Prepare:

  • Be realistic: Ask only for what you need and have a clear plan for repayment.

  • Explain your situation: Be transparent about why you need the money and how you plan to repay it.

How to Approach It:

  • Be respectful: Acknowledge that this is a difficult conversation and that you appreciate any consideration.

    • Example: “I wouldn’t ask if it wasn’t necessary, but I’m in a tight spot. I’d like to borrow $X, and I’m confident I can repay it by [date].”

Tip: Make a formal agreement for repayment to avoid misunderstandings later.


6. Splitting Bills in a Group

Group dinners or vacations can lead to awkward moments when splitting the bill, especially if someone’s share seems unfair.

How to Prepare:

  • Set expectations early: Before the event, agree on how the bill will be split—whether evenly or based on individual orders.

  • Use technology: Tools like Venmo or Splitwise make splitting bills easier and more transparent.

How to Approach It:

  • Be upfront: If the split seems unfair, speak up politely and suggest an alternative.

    • Example: “It looks like I ordered less, so I’d prefer to cover just my portion if that’s okay.”

Tip: Avoid making the conversation feel personal. Keep it focused on the numbers.


after you send them the invoice its been 84 years

How to Make Financial Conversations Less Awkward

  • Practice empathy: Understand the other person’s perspective and approach the conversation with care.

  • Be direct but kind: Clear communication is key, but there’s no need to be harsh.

  • Prepare for objections: Anticipate pushback and plan how to respond calmly.

  • Stay professional: Keep the conversation focused on the issue at hand, avoiding emotional or personal tangents.

  • Use tools: Technology like invoicing apps, payment platforms, or budgeting tools can make these conversations more straightforward.


Awkward financial conversations don’t have to be stressful. By preparing ahead, being empathetic, and maintaining clear communication, you can handle these situations confidently and come out with positive results. Whether you’re asking for payment, negotiating a raise, or denying a loan request, these strategies will help you navigate these conversations successfully.

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