For many lawyers, billing is the most uncomfortable part of the job.
You do great work, solve complex problems, and deliver real value, yet when it comes time to follow up on an unpaid invoice, things suddenly feel awkward.
In my conversation with legal business strategist Matt Darner on the “Be That Lawyer” podcast, we unpacked why that discomfort exists, how it’s costing firms more than they realize, and what lawyers can do to change it.
Get Out of Your Own Head: Reframing Client Communication
Matt discusses the mindset lawyers often have when following up with clients about invoices.
Instead of feeling like you’re harassing or bothering clients, the approach is reframed: sending an invoice is an opportunity to showcase the value and work you’ve delivered.
The follow-up isn’t about pestering for payment, but about reinforcing the relationship and reminding clients of the progress made on their behalf.
Matt explains how training your team to approach these calls with confidence and helpfulness can turn a potentially awkward moment into a positive touchpoint.
The Confidence Erosion: Why Systems Matter in Law Firms
Matt explores how initial client confidence can erode over time due to system failures and lack of communication.
Even when attorneys start a case with high energy and optimism, things can go wrong, cases stall, communication lapses, and clients are left in the dark. This leads to clients building negative narratives and justifying delayed payments.
The takeaway: Consistent communication and robust systems are essential to maintaining client trust and ensuring timely payments.
Stop Having Lawyers Chase Invoices
Why are top-performing lawyers — people billing at the highest levels — spending hours chasing down unpaid invoices? It’s a misallocation of talent and time.
Drawing from his background in sales, Matt emphasized that the most successful client relationships, including some of his largest deals, all began the same way: with clear expectations.
When you start off by setting and then meeting those expectations, everything from communication to collections becomes smoother.
Firms need to rethink their structure and support systems so that lawyers focus on high-value legal work, not collections.
“If you’re not invoicing regularly, it is communicating something is wrong with your business, whether you know that or not,” Matt says.
Connect with Matt Darner:
Website: https://collbox.co/
LinkedIn: https://www.linkedin.com/in/matthewdarner/
Listen to the latest episode of “Be That Lawyer” here, and if you’re serious about leveling up your business development, grab a copy of my new book, now available on Amazon.
Steve Fretzin is a bestselling author, host of the “Be That Lawyer” podcast, and business development coach exclusively for attorneys. Steve has committed his career to helping lawyers learn key growth skills not currently taught in law school. His clients soon become top rainmakers and credit Steve’s program and coaching for their success. He can be reached directly by email at steve@fretzin.com. Or you can easily find him on his website at www.fretzin.com or LinkedIn at https://www.linkedin.com/in/stevefretzin.
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