How to Handle Difficult Attorneys as a Legal Assistant

Working as a legal assistant is a demanding yet rewarding career. However, one of the biggest challenges you may face is dealing with difficult attorneys. Whether it’s a high-strung litigator, a micromanaging partner, or an attorney who constantly changes deadlines, navigating these professional relationships requires patience, strategy, and emotional intelligence.

In today’s fast-paced legal environment—where remote work, AI-driven research, and globalized cases add layers of complexity—handling difficult attorneys has become even more nuanced. Below are actionable strategies to help you manage these interactions effectively while maintaining your professionalism and sanity.

Understanding Why Attorneys Can Be Difficult

Before diving into solutions, it’s important to recognize why some attorneys exhibit challenging behavior.

High-Stress Environments

Attorneys often operate under immense pressure—tight deadlines, high-stakes cases, and demanding clients can make even the most composed professionals irritable. A 2023 American Bar Association report found that 68% of attorneys experience chronic stress, which frequently trickles down to their support staff.

Personality Types

The legal profession attracts strong personalities. Some attorneys are perfectionists, while others thrive on confrontation. Understanding their behavioral tendencies can help you tailor your approach.

Generational and Cultural Differences

With Baby Boomers, Gen X, Millennials, and Gen Z all working side by side, communication styles vary widely. Younger attorneys might prefer Slack or Teams, while older partners may still rely on emails—or even handwritten notes.

Strategies for Managing Difficult Attorneys

1. Set Clear Boundaries Early

One of the best ways to prevent friction is to establish professional boundaries from the outset.

• Define Availability: If an attorney expects responses at midnight, clarify your working hours unless it’s an emergency.
• Push Back Politely: If given an unrealistic deadline, say, “I can prioritize this, but to do it well, I’ll need until [reasonable time].”

2. Adapt to Their Communication Style

Some attorneys want bullet-point summaries; others prefer detailed memos. Pay attention to their preferences and mirror them.

• For the “No-Nonsense” Attorney: Keep emails concise.
• For the Micromanager: Provide frequent, brief updates before they ask.

3. Document Everything

CYA (Cover Your Ass) is a golden rule in legal support.

• Confirm Instructions in Writing: After a verbal request, send a follow-up email: “Per our discussion, I’ll [action] by [deadline]. Let me know if anything changes.”
• Track Changes: Use version control in documents to avoid “I didn’t ask for this edit” conflicts.

4. Stay Calm Under Fire

When an attorney snaps or criticizes harshly, avoid reacting emotionally.

• Pause Before Responding: Take a deep breath.
• Use Neutral Language: Instead of “You’re wrong,” try “Let me double-check that for you.”

5. Leverage Technology to Reduce Friction

AI-powered tools like Clio, Relativity, or EvenUp can streamline workflows, minimizing room for disputes over missed deadlines or errors.

• Automate Routine Tasks: Use templates for frequently drafted documents.
• Shared Calendars: Sync deadlines to avoid scheduling conflicts.

6. Know When to Escalate

If an attorney’s behavior crosses into harassment or abuse, report it to HR or a supervising partner. No job is worth enduring toxicity.

Real-World Scenarios and Solutions

Scenario 1: The Last-Minute Demander

Problem: An attorney drops a 50-page brief on your desk at 5 PM, due by 9 AM.
Solution:
- Politely explain the time required: “I can draft an outline tonight, but a full edit will need until noon.”
- Suggest delegating parts to another team member if possible.

Scenario 2: The Never-Satisfied Perfectionist

Problem: No matter how much you refine a document, they keep requesting changes.
Solution:
- Ask for a style guide or checklist upfront.
- Schedule a mid-process review to confirm you’re on track.

Scenario 3: The Yeller

Problem: An attorney raises their voice when stressed.
Solution:
- Stay composed and let them vent.
- Later, privately say, “I want to support you best—how can we handle urgent requests more smoothly?”

The Bigger Picture: Legal Industry Trends Affecting Attorney-Assistant Dynamics

Remote Work Challenges

Hybrid work has blurred work-life boundaries. Some attorneys now expect 24/7 responsiveness. Firm-wide policies should clarify after-hours expectations.

AI and Job Security Concerns

Some attorneys fear AI will replace support staff, leading to defensive behavior. Proactively showcase your irreplaceable skills—critical thinking, client rapport, and adaptability.

Globalization and Time Zones

With international clients, late-night calls are more common. Negotiate fair compensation for overtime or alternate schedules.

Self-Care for Legal Assistants

Dealing with difficult attorneys can be draining. Prioritize:
- Mental Health Breaks: Step away from the desk.
- Networking: Vent to peers (confidentially) for support.
- Skill Building: The more competent you are, the less they can nitpick.

Handling difficult attorneys isn’t about “winning” conflicts—it’s about fostering productive working relationships. By staying proactive, communicative, and unflappable, you’ll not only survive but thrive in your role.