8 Tips for Dealing with Difficult Opposing Counsel

By Pari Karim and Jennifer Ballard

Everyone has had to deal with “that guy.” You know the one. The one who turns every litigation decision into a battle royale. The one who makes threats about lawsuits, deadlines and strategies. You name it this person will threaten you with it. The loudest, angriest attorney in the courthouse – and that’s saying something! Here are eight approaches to better handle the difficult lawyer.

1. Point out Common Ground

Nothing takes someone off guard faster than telling them you agree with them. And nothing will confound the difficult opposing counsel like telling them there is no fight when they are geared up for one. Of course, this isn’t to say you should just give in, but emphasizing points of agreement that exist is a great way to disarm an opponent. Pointing out common ground in front of a judge will make you look more reasonable than the attorney that is trying to “win” every point. By taking areas of common ground off the battlefield, you will also be able to increase efficiency in litigation, which makes clients happy.

2. Don’t be Afraid to Ask Why

Just because someone is making demands and giving ultimatums doesn’t mean you have to answer them without question. Instead try answering them WITH a question: “Why is this so important to you?” or “Why do you want ‘x’?” There is only one way to satisfy a position, but there may be many ways to satisfy the underlying interest – some of which may provide mutual gain!

3. Separate the Person from the Problem

It’s easy to get sucked into an adversarial relationship when the system is by its nature adversarial and opposing counsel is approaching you as a competitor. Remember, opposing counsel isn’t the problem; it’s the tactics they are employing that are problematic. Try to frame interactions without blame or judgment of the person, but highlight the actions instead. This will decrease the likelihood of enflaming them further, and will lead to more peaceful interactions.

4. Focus on your Interests

Another way to say this is “keep your eyes on the prize.” Focus on what you are trying to get out of each interaction and not on winning each presented battle. If counsel is trying to control the briefing schedule, let them, as long as it’s not impacting your interests (expediency, ability to respond, etc.). They expect a battle, but don’t get caught up in the small stuff.

5. Don’t Fall for your Assumptions

It’s so easy to think we know what is motivating our adversaries. Every action and statement from the other side has a purpose and because of past experiences it’s easy to jump to conclusions as to what opposing counsel and his client are up to. That motion that was filed at the last minute? He just wants you to be unprepared. That continuance they asked for? They’re just delaying matters to be a thorn in your side! Sometimes your assumptions are correct. This helps you to maximize the efficiency in which you are assimilating information. Many times they are not incorrect. Perhaps the motion was filed at the last minute because of new information. Maybe that continuance was asked for to build in some more time to explore settlement options. Believing incorrect assumptions just escalates conflict. Recognize when your reaction is to factual information and when it is based off of assumptions. This will help you act in a more calculated and reasonable manner.

6. Take a Calculated Approach

Just because we have an adversarial system does not mean that every situation requires a competitive approach. Competitive approaches are great when you don’t have to have an ongoing relationship with the person. If it is someone you will be facing in the future, because litigation will likely drag on or because your legal community is small, try to take the ongoing relationship into consideration. Know when to avoid or even accommodate (see #4) and know when compromising or collaborating might be a better approach. Compromising is a great strategy for making quick decisions and improving the ongoing relationship. Collaborating opens options for win-win resolutions by allowing both sides to be heard and engage in dialogue (sometimes with the help of a mediator or other neutral). When you respond instead of react, you have the upper hand, regardless of your approach.

7. Control the Conversation by Reframing

The difficult attorney likes to make demands and inflammatory statements. He likes to be in control of the conversation. You can flip the script by using a reframe. Change complaints to requests. Instead of focusing on what they are dissatisfied with, focus the conversation on what it is they would like to have happen. Restate positions as interests. They may be demanding one thing, but what are they really looking for? Have a conversation about how to satisfy both sides’ interests. Define individual goals as joint ones. You will automatically change a competitive situation into a collaborative one. Change the focus from the past to the future. Next time opposing counsel says, “I’ll expect an answer by the end of the day of the day.” You can say, “I am glad that we both want to have this matter settled quickly.” Then negotiate a timeline that works for both of you.

8. Pick up the Phone

It’s so easy to miscommunicate via electronic communication. Sometimes that difficult attorney is more difficult with keyboard courage and the angry voice you use when you read their e-mails. Perhaps word choice or shortness in response to you is increasing your conflict. Picking up the phone is faster because you can  engage in a dialogue, allowing you to respond and ask questions immediately. Hearing each other’s voices allows you to better determine when someone is making an offer and when someone is making an ultimatum, being difficult or simply trying to resolve an issue, and ultimately gives you more information about what tactics you should take to respond.

Jennifer Ballard

Jennifer Ballard is a director for the WBAI and is a Partner at Hinshaw & Culbertson.

Pari Karim headshot

Pari Karim is the Training Director at the Center for Conflict Resolution, where she leads a 40-hour Mediation Skills Training, as well as workshops in Conflict Management, Negotiation, Settlement Skills, and Mediation Advocacy. Find out more about CCR at

WBAI members interested in CCR’s 40-Hour Mediation Skills Training qualify for a discounted rate! Call 312-922-6464 x15 for more information.

This article originally appeared in the WBAI Winter 2016 Newsletter.