Big-Picture Scenarios Guide Law Associates’ Critical Thinking

This article was originally published by Bloomberg Law. 

A deficit of critical thinking among law firm associates is now a recurrent theme in legal practice. This deficiency impairs an attorney’s individual effectiveness—and it also impacts law firms’ overall efficiency. As firms more frequently integrate sophisticated tools such as generative AI, they must take extra care to ensure associates using these programs assess their output critically.

How should law firms tackle a critical thinking crisis? It may be a challenge, but using strategies such as comprehensive guidance, experiential training, and data-driven feedback can go a long way.

Big Picture

A key step in fostering critical thinking is to give associates a comprehensive lay of the land in a given case. This requires helping them first understand the basic structure of a deal or litigation matter before immersing them in the business realities and context that shape legal outcomes.

Associates can get lost in the weeds of their day-to-day work assignments. Set them up for success by giving them a strong foundational understanding of the practice.

So much of what associates miss is due to a failure to ask “why?” Ensuring associates understand where their assignments fit in the overall deal or lawsuit will sharpen their ability to know when to pursue lines of inquiry.

Experiential Learning

The traditional “lunch and learn” training format, while convenient and well-intended, often fails to engage associates in meaningful learning. Training should be interactive and demanding, requiring active participation rather than passive absorption.

The best way to achieve this is to have associates complete mock assignments and receive feedback.

For transactional associates, this could mean reviewing and marking up agreements in anticipation of negotiation, or orchestrating a closing with timelines and deal documents. For litigators, it could involve writing sections of a motion to dismiss or drafting a meet-and-confer email to opposing counsel about a discovery dispute.

Firms should create a dynamic learning environment where associates can learn by doing—and make mistakes in a safe environment where they may question, discuss, and interact with both the material and their peers.

This method reinforces legal concepts, improves retention, and encourages critical thinking by immersing associates in real-world scenarios that require problem-solving and decision-making skills. Active participation can also build confidence in newer attorneys, which empowers them to handle their everyday tasks more effectively.

Real Deal

As much as possible, training should use actual deal documents, complex procedural histories, and messy fact patterns that typify actual client work.

Rather than rely on simplified or simulated scenarios, training should require new associates to grapple with the square peg, round hole problems that lawyers face every day. Mock assignments should require associates to synthesize different, imperfect, and often conflicting pieces of information—and then actually complete the assignment.

While reviewing mock deal documents and issue-spotting is better than having associates listen to a lecture, it’s still too passive and doesn’t allow associates the practice needed to develop their critical thinking muscles. Having associates work with these real deal documents to complete mock assignments is crucial.

Data-Driven Feedback

In addition to having associates go through mock assignments, firms should review those assignments and provide meaningful feedback. They should base their assessment structure on a consistent rubric and watch out for any gaps in crucial critical thinking skills.

While the rubric isn’t for the purpose of giving grades, it will help firms gather key data on associate performance and fairly inform evaluator feedback. Firms can use this rubric both to give individual associate feedback and to inform observations on trends across associate classes.

A sample rubric for these assessments could determine whether the associate:

• Followed specific instructions
• Applied the correct concept and adapted it for the given situation
• Identified all legal and practical issues
• Devised a unique business solution
• Used best practices (such as best drafting techniques and approach)

Feedback from partners and other supervisors should be constructive, focusing on encouraging questions, deeper analysis, and reflection.

Firms can also have associates self-assess their performance on the assignments. Comparing the associate self-assessments with instructors’ feedback will help create awareness for associates on how others are viewing their work.

Interactive group review sessions can be especially effective for fostering critical thinking. Partners or reviewers can discuss the assignment in small groups, weave in tailored feedback, war stories, and best practices, while encouraging associates to ask “why” and discuss gray areas.

These review sessions should nurture inquiry and critical thinking by encouraging associates to question assumptions, explore alternative solutions, and discuss business context.

Developing critical thinking skills in law firm associates isn’t just about enhancing individual capabilities—it’s also about keeping up with the demands of modern legal practice. By adopting these strategies, firms can position themselves as leaders and mentors to a new generation of lawyers.