At Practice 360º, Lawyers Gain Insight Into Smart Billing and AI Practices
October 15, 2025
Gathered on October 8 for the D.C. Bar’s annual Practice 360º event, attorneys learned strategies to boost their services, stay abreast of the latest technological advancements in the legal space, and navigate business and ethics concerns.
Savvy Billing Practices
During “Bill It, Track It, Trust It: The Ultimate Guide to Capturing Time, Getting Paid, and Staying Compliant,” Jordan Turk of Smokeball reiterated that while good lawyering is a large part of a successful practice, another piece is managing one’s finances, especially if an attorney is in a small or medium firm. Turk offered insight into mastering a firm’s money systems and staying on top of billable hours at all stages of a case.
Turk talked about best practices for fee agreements, such as listing every person who can bill on a case, along with their respective hourly rate. Turk also highlighted the importance of including a mechanism in the agreement that lets attorneys increase their rate yearly. Attorneys should also ensure at the initial client meeting that the scope of fee agreements is properly limited and explain the billing structure as well as when to expect invoices.
Turk also dove into nonrefundable retainers and earned-upon-receipt arrangements, pointing out tips for handling prepaid fees. She stipulated that they should be in a trust account and that they cannot be earned on receipt, despite what an engagement agreement between the attorney and a client says.
For improving the billing process, Turk had several tips for attorneys. Be organized and prompt in delivering an invoice to a client. Also, bill clients regularly, predictably, and as close to payday as possible. Discuss billing and invoicing at the initial client consultation, which will avoid headaches. In addition, use credit cards and other online payments to one’s advantage, such as adding a link to a signature block. Finally, be consistent with billing procedures. “The longer you wait to bill a client, the less likely they are to pay it,” Turk said.
Turk added that attorneys should follow up with clients a week after the invoice is sent — it helps to put the task on a calendar — and be prepared to defend any bill.
Pros and Cons of AI
Artificial intelligence is shaking up the workplace, promising several benefits. However, the evolving technology also presents possible pitfalls for attorneys and their clients. In the session “AI in Your Practice: A Guide to Practical, Performant, and Private Use,” Erich Dylus of Varia Law discussed what AI can do for lawyers and how best to utilize it without running afoul of ethical and privacy concerns.
Dylus, an attorney and programmer who utilizes AI and blockchain technology, likened AI to a “genius intern” that can help the profession be more lawyerly and less administrative. Dylus said that AI services, such as Microsoft’s Copilot or OpenAI’s ChatGPT, can handle tasks like providing a second opinion, being a strategic consultant, spotting issues, offering deep research, and more. But he clarified that while AI can be a great assistant, it is not going to replace lawyers.
“If you use [AI tools] properly, they have low downsides and super high upsides,” said Dylus.
Dylus provided a crash course on how AI works, mentioning that it requires a strong prompt, which allows it to generate a natural response via its large language model — a system trained by data that can process and respond to queries. Specify a “role” for the AI and the “task” it should do, outline further “instructions,” and provide context, including clarifying rules. Then ask it to analyze your first submission to gather a stronger idea.
Dylus added that AI is probabilistic — the responses it generates will vary — so he advises users to repeat their questions multiple times when needed. Ask the tool to provide citations and engage multiple AI platforms to get answers.
With practice and strong prompts, AI can be a phenomenal tool to help you do your job better, said Dylus, but attorneys should be careful of what they put into the system.
When it comes to using AI and maintaining privacy, “assume the worst,” he added.
Lawyers using AI should assume responsibility for what they enter into the system and what results they get from it, said Dylus. He noted that information entered into the system is often retained by the service and can be viewed by third parties.
AI can also hallucinate answers, too, Dylus said, providing users with incorrect or misleading answers, so attorneys must ask the tool to cite its sources and ask questions again if needed. He also cautioned lawyers against using AI as their single resource.
When using AI, Dylus said, “I copy the content, redact and privatize it, put it in the prompt and get my output, then I review the results, and I manually change the authoritative version.”
Approaching AI as a smart assistant that can assist with certain time-consuming tasks will augment your practice and put you at an advantage, said Dylus, and attorneys should take time to get familiar with the tech.
