The Billing Blues: A Special “Time-keeping” Edition of Lawyer Stories

Time is quite literally money in the legal profession. For lawyers who bill by the hour, accurate timekeeping can be the difference between a profitable practice and financial chaos. Yet for many attorneys, tracking billable hours remains one of the most dreaded aspects of their professional lives.
In this special “Billing Edition” of Lawyer Stories, we dive into the sometimes humorous, often painful, world of billable hours and the battles between lawyers and firm leaders:.
Timekeeping Tales
It should surprise no one that lawyers (aka human beings) aren’t naturally conditioned to keep time (aka act as a stopwatch). It’s no wonder there are so many stories of bad timekeeping habits and frustrating end-of-month billing disasters. Take it from these real Reddit stories:
“I’ve known several partners who would consistently be 4-6 months behind on billing. The guy who owned the firm was the worst offender.”
“Billing is easy when I can just sit down and crank out motions in blocks of hours but that’s usually not the case. I often bounce between different tasks and having to capture every small thing disrupts my flow.”
“Every month I begin the month with the full intention of contemporaneously billing. That has never happened and I do not believe that will ever happen. In the end, I spend at least 10 hours or more just putting in billing entries at the end of the month.”
The Punishment Arsenal
To try to shift the tide on billing, law firms have developed increasingly creative enforcement methods:
The Axing of Access: Some firms configure their networks to automatically disable internet or computer access for employees who haven’t submitted time entries by the weekly deadline.
The Direct Deposit Denial: Delinquent timekeepers lose the privilege of direct deposit. “You’d have to make the long trek down to the managing partner’s office to get your paper check and carry it back in shame.”
The Dunce Cap of Delinquency: One unnamed litigation firm requires delinquent timekeepers to wear a brightly colored dunce cap in the office. If we hadn’t seen the photographic evidence, we would think this was urban legend.
The Bonus Blockade: One common approach among BigLaw is withholding bonuses from attorneys who fail to meet timekeeping requirements or reducing bonuses via late time submission ‘fines’. In some cases, bonuses could be docked up to 50%!
The Nuisance of Notifications: Firms have taken timesheet reminders to a new level, from gentle reminders to 3-5 emails daily, followed by stern calls from CFOs. Some firms issue pop-up notifications every 10 minutes until delinquent time is submitted (that’s up to 140 notifications a day!).
A Better Way Forward
Progressive firms are adopting new approaches to timekeeping. AI-powered solutions like Billables AI are transforming how attorneys track their time by automatically capturing work activities and generating accurate time entries. These platforms eliminate the mental burden of manual tracking while improving billing accuracy.
Whatever the solution, it’s clear that the traditional approach creates significant stress in an already demanding profession. Moving toward automated solutions offers a pathway to more sustainable legal careers by reducing administrative friction and allowing attorneys to focus on what they do best – practicing law.