The Art of Negotiation: Get Inside Your Opponent’s Head

The life of a new attorney can be a rough ride. Dealing with potential clients can be tricky, you work all hours of the day, and sometimes wake up in the middle of the night to answer email.

Learning to negotiate is another tall task. Before you do anything else, make sure you understand your client’s goals and your settlement authority. Then, proceed to step two: getting inside your opponent’s head.

Negotiation is Like Poker

The best poker players will tell you that you’re not playing your hand—you’re playing your opponent’s hand. It’s not exactly the same in negotiation, but it’s similar.

If you can learn how opposing counsel likes to negotiate—their tells, their strengths, and their weaknesses—you can adapt your strategy to match and counter their strategy. It isn’t based on their legal position. Instead, it’s based on their negotiation style.

For example, say opposing counsel presents an offer and then says something like “please let me know your client’s response so that I can pass it along to my client for review.” Opposing counsel just told you two things: (1) they don’t expect your client to accept their offer; (2) their client is willing to change their position. They may not have said that exactly … but they said it just the same. When I get an email like that, I immediately tell my client to reject the offer and go back with a counteroffer.

Here’s another poker trick. It’s called putting your hands on all of your chips, bluffing to go all in, and then pulling your hand back. This is when opposing counsel calls you up for ten minutes of verbal scathing on why your case is terrible, and then in the last thirty seconds makes a settlement offer and then asks for a response.

Focus on what actually happened, not what almost happened. Real poker players go all in when they want to go all in. Attorneys bring a motion, take a deposition, or litigate if they think they have the upper hand. They don’t threaten fire and brimstone but then just make a settlement offer. In other words, your opponent is bluffing.

It always matters what you have in your hand, but knowing how they approach negotiation is just as important.

Get the 411 on Opposing Counsel

I work in a niche practice area, which means the local players are usually the same. Sure, there are big fish, small fish, and weird fish I’ve never seen before. Before I even file a case, I do thorough background research on the other side and who represents them.

This information is beyond helpful. Because I encounter the same attorneys over and over, I have (generally) learned how they defend cases and how they like to negotiate. Do I have the entire playbook? Of course not. But I know enough to understand their general style. When I encounter someone I don’t know, I ask around. Someone always knows something about opposing counsel, and they are usually willing to share that information.

As a starting point, check out their firm bio. Find out how long they have been practicing, where they went to school, and what types of cases they typically handle. If they have been practicing for thirty years, they will negotiate much differently than a young attorney. If they are general counsel or in-house counsel, they may lack a certain level of objectivity because they are more connected to their client.

If they usually handle cases in a different practice area, then get ready to teach them your practice area. More importantly, prepare for some weird negotiations, as they likely don’t understand the typical value of the cases you handle. Sometimes this can be good, but sometimes it can be very frustrating. Either way, this is a great piece of information to know before engaging in any negotiations.

Ask Them How They like to Negotiate

In any practice area, there are the superstar attorneys on both sides. If you’re a young attorney, finding yourself engaged in negotiations with the Michael Jordan of the other side is terrifying.

I had a case early in my career case that was handled by the local superstar defense counsel. This attorney’s reputation is not just local, it’s national. So when I was told to “call ’em up and get the case settled” my blood pressure went through the roof.

In case you didn’t know, I used to work for Sam. Early on, Sam’s advice was “ask how they like to negotiate.” At face value, that sounds ridiculous. Who in their right mind is going to give away their strategy?

It seemed so insane that I went for it. The response? “Wow, that’s the best question I’ve ever been asked.” To top it off, opposing counsel then proceeded to explain how their client liked to negotiate and what I needed to do to get the case settled. And they weren’t bluffing because this attorney told my colleagues how impressed they were that I had the guts to ask.

Admittedly, this question does not always work. But sometimes it does. Even if they won’t tell you everything, they will probably tell you something. And in negotiation, knowledge is power.

Find Their Comfort Zone and Use Every Piece of Information

Every attorney, every case, and every client are different. However, attorneys generally handle cases in a select area(s) of practice and tend to follow a script with minor deviations each time. If they negotiated a particular way before, they will likely do it again.

Some attorneys bluster on the front end and then quickly move into settlement talks. Other attorneys offer to settle up front, then dig in and won’t radically alter a position for months. Sometimes clients/attorneys like to resolve cases at the end of fiscal quarter/fiscal year.

If you know how a lawyer prefers to negotiate, taking them out of their comfort zone can be a very good thing. Some attorneys will start to show their cards when you call their bluffs. Of course, other attorneys will just go over the top and push back even harder. However, knowing how the other side will play the game is a very nice advantage.

Also, external factors like vacations and other pressing cases can have a dramatic impact on settlement talks. Of course, you won’t learn that information if you never engage in a little small talk or banter. Attorneys like things nice and tidy before they check out for a week. If they share that piece of information, use it to your advantage.

Once you have a handle on client goals and settlement authority and your opponent, you’re ready to start talking deals. Make sure you know where you are going to make sure you end up in the right place.

Originally published 2012-04-10. Last updated 2016-10-20.


  1. With respect, I would suggest that your thoughtful piece is missing a crucial, often the crucial point in negotiations: understanding the other side’s needs, desires and abilities. Negotiation, especially for contracts, can (and in my view should) be a win/win, not win/lose, situation. Knowing what the opposing side can and cannot (or may/may not) provide, and only asking for those things that are possible and reasonable, makes a successful outcome much more likely for both parties. That doesn’t mean giving up on leverage, or not pushing hard for your client’s position, but rather doing so without being so demanding, so unreasonable that either the agreement doesn’t happen or it does but with acrimony and distrust.

    Certainly, litigation negotiation (especially with “abusive debt collectors”) is a very different context than business contracts, but I still argue that the principles remain the same. Even an abusive debt collector can be disarmed and brought to agreement if the other party puts the collector in the position of either defending an unreasonable position or accepting a reasonable, and workable, alternative. Opposing parties don’t have to be opponents. {Jonathan}

  2. Sam Glover Sam G. says:

    Asking opposing counsel how to settle the case is one of my favorite strategies. I never know whether the other party needs to be led to a number through a bunch of back-and-forth movement, or whether they are more comfortable with a straightforward “here’s our number; take it or leave it” approach. When in doubt, ask.

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