Dan Henn CPA
Dan Henn CPA

Still Manually Sending Invoices? Here’s How to Save Hours Every Week

If you’re still manually creating invoices, chasing payments, or reminding clients to pay by email, it’s time to rethink your billing process. These small tasks may not seem like a big deal—but over time, they drain hours of your week, fragment your focus, and create unnecessary stress.

I used the same thing. Fortunately, I had my wife involved in the practice and she does the billing. I have also had my admin employees do this as well. It really should be anyone but you. This would also include collections.

Billing doesn’t have to be this way. With the right tools and automation systems in place, you can eliminate most of the manual work, reduce overdue payments, and maintain a more professional image—all while protecting your cash flow.

Here are 8 strategies to automate and streamline your billing process as a tax resolution pro:

  1. Use Practice Management Tools with Built-In Billing

    Tools like TaxDome, Practice Ignition and Karbon integrate client communication, task tracking, document management, and billing—all in one system. These platforms allow you to:

  • Generate invoices automatically from engagement templates
  • Collect payments securely via ACH or credit card
  • Send recurring bills or one-time charges
  • Monitor payment statuses from a centralized dashboard

If you’re using multiple tools or spreadsheets for billing, switching to a platform with built-in billing features can eliminate redundancy and improve turnaround time.

  1. Set Up Recurring Invoices for Ongoing Clients

    Have clients on monthly retainers or long-term resolution plans? Don’t manually create an invoice every month. Set it once, and let your system send recurring invoices automatically.

Most platforms let you choose the frequency (monthly, quarterly, annually), apply sales tax if needed, and even auto-charge saved payment methods—so you don’t have to follow up repeatedly.

  1. Automate Payment Reminders (and Stop Chasing Clients)

    Even good clients forget to pay. Rather than sending awkward “just checking in” emails, let your invoicing system handle this for you.

Set up automated reminders to go out:

  • 3 days before the invoice due date
  • On the due date itself
  • At regular intervals after a missed payment (e.g., every 5–7 days)

This alone can drastically reduce the number of overdue invoices.

  1. Combine E-Signature with Upfront Payment Collection

    Want to improve cash flow and reduce non-payment? Require payment at the same time clients sign your engagement letter. Best way to deal with Accounts Receivable is to never have Accounts Receivable. Get paid in advance before work is to be completed.
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How to Attract Higher-Paying Tax Resolution Clients (Without Chasing Leads All Day)

If you’re tired of dealing with price-shoppers and last-minute filers who ghost you when you quote your fee, you’re not alone. The truth is: premium clients do exist—but they’re not looking in the same places, and they’re not motivated by discounts.

High-value clients expect professionalism, authority, and trust. They don’t respond to vague “I can help” offers or bargain-bin pricing. Instead, they want to feel confident they’re hiring someone who can solve a serious problem—like dealing with a $50,000 (or more) tax debt or avoiding IRS collections.

Here are 8 strategies to attract better clients who will value your expertise and happily pay what you’re worth:

  1. Lead With Value (Benefits of Your Services), Not Services (Features)
    Don’t just list what you do (tax resolution, liens, levies, etc.) — communicate why it matters. Talk about outcomes (peace of mind, saved money, removed liens, sleep better at night) instead of deliverables (forms filed, documents prepared). Premium clients care less about your process and more about the result. Position your services as the solution to their stress, not just a transaction.
  2. Showcase Your Expertise
    Post consistently on your website, email list, and social media. Share insights, anonymized client stories, and tips that show you’re the go-to authority on IRS issues—not just another tax preparer. Blog posts, short videos, or carousel posts on platforms like LinkedIn and Instagram go a long way toward establishing your credibility.
  3. Tighten Your Messaging
    Speak directly to the problems premium clients want solved: IRS stress, growing penalties, frozen bank accounts, wage garnishments. Use their language, not technical tax jargon. Instead of saying, “I help with Offers in Compromise,” say, “I help business owners cut their IRS debt by up to 90%.” That kind of message lands.
  4. Use Premium Positioning
    Everything from your website design to your email signature should reflect professionalism and clarity. Avoid cluttered sites, outdated graphics, or cheap-looking branding. Your digital presence is your storefront—make sure it tells the right story. Oh, and make sure that your images match the message you are trying to convey (e.g. don’t talk about pain and put a picture of a smiling person)
  5. Build Strategic Referral Relationships
    CPAs, EAs, attorneys, and financial advisors are trusted advisors to the clients you want. Many don’t want to deal with IRS tax resolution themselves, but still want to offer a solution to their clients. Position yourself as THAT solution by offering co-branded webinars, providing referral kits, or hosting lunch-and-learns.
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How to Strengthen Client Relationships and Set Better Boundaries

Client relations can make or break your tax practice. You could be a technical expert, a pricing pro, and an IRS collections specialist—but if your communication and client boundaries are shaky, you’ll always feel overwhelmed, undervalued, and on the back foot.

Building strong client relationships isn’t about always being available or saying yes to everything. It’s about creating trust, managing expectations, and knowing when to lead with empathy—and when to enforce boundaries.

Here are 8 strategies to build better relationships and protect your time:

  1. Set Expectations Upfront

    From your very first interaction, explain your process, timelines, communication preferences, and availability. Clear expectations reduce misunderstandings and help clients feel more secure.

  2. Communicate Proactively

    Don’t wait until a client is frustrated or confused. Schedule regular check-ins, even if it’s just a quick update email. Clients who feel informed are less likely to micromanage or panic.

  3. Define (and Defend) Your Boundaries

    Let clients know when and how they can reach you—and stick to it. Include office hours in your email signature and use autoresponders if needed. Boundaries help clients respect your time and build a healthier working relationship.

  4. Avoid Jargon—Explain Things Simply

    Clients aren’t tax pros. The more clearly you explain complex matters, the more confident and loyal your clients will be. Use metaphors, visuals, or stories to help make abstract tax issues more relatable.

  5. Know When to Push Back

    If a client is asking for something unrealistic, unethical, or outside the scope of your services, don’t be afraid to say no. How you say it matters—do it with professionalism and kindness, but do it clearly.

  6. Get Feedback Regularly

    Use short surveys or one-on-one conversations to understand how your clients feel about your service. You’ll build rapport and uncover areas to improve before issues arise.

  7. Use Agreements and Documentation

    Never rely on verbal understandings. Use written engagement letters, scope agreements, and signed authorizations for everything. This protects you legally and creates clarity with the client.

  8. Fire the Wrong Clients When Necessary (and FAST)

    Sometimes, a bad client isn’t just a drain—they’re a liability. Don’t be afraid to part ways professionally when someone consistently disrespects your boundaries, misses deadlines, or refuses to follow your advice.

Final Thoughts

Strong client relationships are built on trust, clarity, and mutual respect. The best tax pros are not just technically competent—they’re confident communicators and excellent boundary-setters. When you take the lead in the relationship, you’ll attract better clients, experience less stress, and build … Continue reading