How Cooper & Scully Makes Timekeeping a Teaching Tool

Investing in the Next Generation of Lawyers

For new associates, timekeeping is one of the first professional skills they must develop alongside learning how to practice law. While navigating research, drafting, client communications, court procedures, and the many demands of a legal career, they are also expected to accurately record their work in a way that is clear, detailed, and consistent with firm and client billing requirements.

Without experience, knowing what to record, how much detail to provide, and how to describe legal work effectively can be challenging. As a result, timekeeping may be delayed, important details may be omitted, or valuable work may go unrecorded altogether.

Cooper & Scully recognized that becoming an effective lawyer involves more than mastering legal skills. It also requires developing the business and professional habits that support client service and firm success. To help associates build those skills while reducing administrative burdens, the firm invested in PointOne’s AI timekeeping platform. The initiative, led by Rachelle Perry, Director of Human Resources, was designed to strengthen timekeeping practices while improving the accuracy and efficiency of the firm’s billing process.

PointOne Helps Associates Capture More Time and Build Better Billing Habits

PointOne helps Cooper & Scully’s associates capture more of their work while providing guidance on how to document it effectively. It automatically captures emails, calendar events, meetings, documents, and other activities throughout the day, then prepares suggested entries based on that work. Attorneys review the suggested matter, duration, and narrative before releasing the final entry directly into the firm’s billing system.

“For many new associates, the challenge isn’t the legal work, it’s knowing how to translate that work into a clear, compliant time entry,” says Rachelle Perry. “Timekeeping is really a form of storytelling. You’re explaining to the client what you did, why it mattered, and the value it provided. PointOne helps associates learn how to tell that story.”

Rather than beginning with a blank timesheet, associates can see how their work translates into narratives. They learn how to describe legal work more effectively, apply the correct matter assignments, and provide the level of detail clients expect. Because suggested entries are linked directly to the originating email, meeting, or document, attorneys can easily verify the context behind their work.

When an associate drafts a time entry, PointOne checks it against the firm’s billing policies and the client’s outside counsel guidelines (OCGs). Firms simply upload their guidelines, and PointOne turns them into rules that apply to each entry.

When an entry breaks a rule, PointOne walks the attorney through the correction:

1. Spot the issue. A dot appears on the entry’s (ⓘ) info button to indicate a potential billing violation.

2. See which rule was broken. Clicking the button opens a panel with a flag card for each issue. Each card quotes the relevant guideline in the client’s or firm’s own words.

3. Understand why. Clicking “Why this entry was flagged” explains the specific problem. For example, the narrative says “contract” without identifying which document was reviewed.

4. Review the suggested fix. Most flags include a compliant rewrite displayed as tracked changes. The associate can accept, edit, or dismiss the suggestion.

5. Verify the original work. The same panel shows the email, call, or meeting behind the entry, so the associate can check the narrative against what actually happened.

When PointOne recommends revisions, it preserves both the original and revised narratives, along with the rule that triggered the change. This transparency helps attorneys understand not only what changed, but why. It also demonstrates how small adjustments in wording can better communicate value to the client while meeting billing goals.

Over time, these corrections became a valuable learning tool. Rather than waiting for shareholder feedback or pre-bill edits, associates receive immediate guidance while reviewing their own work. They can identify issues, understand the reasoning behind corrections, and apply those lessons to future entries.

“Associates are learning an entirely new skill set when they begin practicing,” Perry explains. “The real-time feedback helps them learn those expectations much faster.”

As billing best practices become second nature, associates develop stronger timekeeping habits while reducing the administrative burden on shareholders and billing staff.

For Cooper & Scully, PointOne has done more than improve billing compliance and capture more billable time. It has created a practical learning environment where associates develop essential timekeeping skills in real time, supporting both professional development and a more efficient billing process.

Results: More Time Captured, Stronger Timekeeping Habits, and Fewer Write-Downs

Since implementing PointOne, Cooper & Scully has automated 71% of attorney time entries and preserved more than 3,800 billable hours that otherwise may have been written down or lost.

One of the greatest benefits for associates has been the guidance PointOne provides early in their careers. While new attorneys often understand the work they performed, they may not yet know how to present that work in a way that satisfies client guidelines and billing requirements.

“New associates often know exactly what work they’ve done, but they may not know how to describe it in a way that satisfies client guidelines and billing goals,” Perry says. “Having those guardrails in place gives them confidence and helps them learn expectations much more quickly.”

With suggested narratives and real-time feedback, associates gain a better understanding of effective timekeeping while building habits that carry forward throughout their careers.

Perry recalls speaking with a new associate who felt he was working long hours but wasn’t seeing that effort reflected in his recorded time.

“He was working hard and spending long days in the office, but he was struggling to translate that work into billable entries,” Perry says. “What he needed wasn’t to work more. He needed help identifying and describing the work he was already doing. PointOne helped bridge that gap and tell the story behind his work.”

The benefits extend beyond associate development. For shareholders and supervising attorneys, PointOne helps streamline the review process by identifying potential billing issues before entries reach pre-bill review.

“Our shareholders still mentor associates on timekeeping, but they’re spending less time correcting basic billing issues and more time coaching,” Perry explains. “PointOne helps move the conversation from ‘what’s wrong with this entry?’ to ‘how can we make it even better?’”

“We’ve captured a significant amount of work that historically may not have been recorded, particularly the frequent communications that occur throughout the life of a matter,” says Jeremy Lindsay, CFO. “Those interactions create value for clients, and PointOne helps ensure they’re reflected in our timekeeping.”

Perhaps most notably, adoption has extended well beyond the firm’s early champions. Attorneys who were initially skeptical of the technology have incorporated it into their daily workflows after seeing its value in reducing administrative burdens, improving compliance, and helping ensure their work is accurately captured.

For Cooper & Scully, PointOne has become more than a timekeeping tool. It has helped associates develop stronger billing habits, improved the quality and consistency of time entries, increased the capture of billable work, and reduced write-downs.

Most importantly, it has given attorneys an opportunity to learn timekeeping the same way they learn other professional skills: through immediate feedback, repetition, and practical experience.

“We’re not just helping associates record their time,” Perry says. “We’re helping them learn how to communicate the value of their work. Timekeeping is part compliance, part business skill, and part storytelling. When attorneys learn how to tell that story well, they become more effective lawyers, serve clients better, and contribute more to the success of the firm.”