The Art of Getting Paid Without Asking!
Wait what! I’ve been spending some time listening and engaging in social media groups to keep my pulse on what new entrepreneurs desperately need help resolving. As it turns out there is a running theme - customers aren’t paying, entrepreneurs are afraid to talk money, and there’s a high refund request among new businesses.
Alright, listen up, entrepreneurs…
If you’re jumping through hoops to get orders but not getting paid, you’re not running a business—you’re running a charity. Business is about transactions: goods and services in exchange for payment. I know you know this. That’s why I also know that you didn’t sign up to be an entrepreneur to give away your time, energy, and expertise for free.
But that’s exactly what’s happening you're giving away your worth, and it's crushing your cash flow. And no cash flow means no business.
I get it - it’s new, uncomfortable, and feels awkward. But the bottom line is, you’ve got to embrace the fact that money is the fuel that keeps your business going. Shake off the idea that you’re "asking" for money. You’re not asking - you’re selling. Besides, when was the last time you ordered something online or walked into a local business, and didn’t pay upfront? Exactly, you paid first, and then you waited for the product to be delivered. Well, your business is no different.
Show Me the Money
While I may not be able to make you feel less awkward about ‘talking money’, I can show you how to strategically implement a few things in your process to bypass the awkward moments. Here are some options to choose from:
1. Set Up Clear Payment Systems
Professionalize your business with automated systems that handle payments. Make payment a non-negotiable part of the transaction, which means your customer’s journey includes payment as an automatic step. And guess what? Once that’s done, you’ll never have to "ask" for money again. It’ll just be part of the flow.
Use Invoicing Software: Tools like QuickBooks, Wave, or HoneyBook can create and send invoices with payment links. Need help deciding the best accounting software for your business?
Integrated Payment Platforms: Services like PayPal, Stripe, and Square allow you to request payments via email or SMS with pre-built templates.
Recurring Payments: If you provide subscription or retainer-based services, use platforms like Chargebee or GoCardless to automate monthly charges.
2. Online Booking
Use Online Booking Platforms with Payment Features. For service-based businesses, online booking systems streamline the payment process and remove the fear that upfront payments will scare clients away. Pair booking with clear cancellation policies to establish expectations. Learn how to establish policies for your business.:
Use platforms like Calendly, Acuity Scheduling, or Book Like a Boss to let clients schedule appointments and pay upfront.
3. Deposits or Prepayments
For ongoing work, create milestones and request partial payments before beginning each phase. Require Deposits or Prepayments. Consider developing non-refundable deposit policies or partial payment terms to ensure commitment from the client before any significant work begins. Structure your payment process so that customers pay at least part of the fee upfront.
For high-ticket services, require a non-refundable deposit to confirm bookings. Learn how to establish policies for your business.:
4. Update Welcome Materials
Add Pricing and Payment Info to Your Welcome Materials. Offer tiered packages with different pricing levels to make the decision easy for your customers. Provide pricing details and payment options upfront in a way that aligns with your brand:
Include clear payment policies on your website, emails, or brochures.
5. Update Proposals
Update and use Proposals with Integrated Payment Links. Highlight your terms clearly, such as "A 50% deposit is required to begin." For service-based businesses, proposals are a great opportunity to include payment terms.
Use tools like PandaDoc, Proposify, or Dubsado to send proposals with embedded payment links.
6. Membership or Subscription
Create Membership or Subscription Models. Monthly subscription services add predictability to your cash flow. Encourage ongoing relationships by offering memberships or retainer packages.
7. Offer Options
Update Digital Contracts with Built-In Payment. This is ideal for consulting services, freelance projects, or custom work. Combine legal agreements with payment steps for a seamless experience:
8. Incentivize
Provide Discounts for Early or Full Payments. Avoid phrasing it as a “late fee”—highlight the positive aspect instead. Encourage prompt payment by offering financial incentives:
Example: “Pay in full today and get 5% off.”
9. Educating Customers
If you feel awkward discussing payment, let your materials do the talking. Educate Customers Through Your Content. Create videos or posts explaining your payment process (e.g., "Why I Require Upfront Deposits"):
Include pricing FAQs on your website or social media.
10. Create Policies
Create Easy-To-Understand Payment Policies. Ensure policies are visible at all points of the customer journey—on your site, in emails, and during consultations. Use clear and professional language to eliminate confusion:
Example: “All payments are due at the time of booking. Your spot is not secured until payment is received.” Learn how to establish policies for your business.
11. Create Passive Income
Use Digital Product Sales for Passive Income. This diversifies your income stream and reduces direct "asking for payment" scenarios. If possible, package part of your expertise into digital products:
E-books, online courses, templates, or toolkits can be sold automatically via platforms like Gumroad, Teachable, or Squarespace.
12. Delegate
Hire a Virtual Assistant or Use Payment Automation. If direct interactions still feel uncomfortable, delegate! Automated email reminders can nudge clients without needing your involvement.
A virtual assistant can follow up on unpaid invoices. Learn more about Building a Team.
OnDemand Workshop: CASH FLOW ISSUES
We’ll break down how to overcome cash flow issues and put systems in place that make payment part of the process, which is not something you have to chase.
CONCLUSION
Stop treating your business like a side hustle where you "hope" to get paid. Step into your role as an entrepreneur. Demand what you’re worth. At the end of the day, this is business—and in business, you either get paid, or you’re out.
