Key Takeaways:
- Improvisation helps contract negotiators create effective solutions when negotiations take an unexpected turn.
- Exceptional negotiators understand the principles behind contract terms instead of relying solely on playbooks.
- Improvisation improves through preparation, experience, live negotiation, and practice thinking on your feet.
When I was in undergrad, I took an improvisation class as an elective. I was a very shy woman at that point in my life. I hadn’t been to law school yet.
One day, during an improv skit, I accidentally tripped over a chair. Instead of stopping, I instinctively worked the fall into the scene. The audience laughed, and when the exercise ended, my professor smiled and said, “There! You just did improv.”
At the time, I assumed he was talking about theater.
Looking back, I realize he was teaching me one of the most valuable skills I would ever use as a contract negotiator.
Lawyers spend years, if not decades, learning how to properly prepare for contract negotiations. But contract negotiations are dynamic. Business priorities change. New information emerges in the last two minutes of the call. Stakeholders raise concerns that were never mentioned in the redlines. Counterparties can have outbursts or unreasonable asks. A routine discussion can suddenly take an unexpected turn.
The way we handle those moments separates good contract negotiators from exceptional ones.
Not because exceptional negotiators prepare less or understand the law better. Though they usually do.
But mostly because they know how to adapt to the moment at hand, not just the one they planned for.
That is improvisation.
Improvisation is often misunderstood as making things up as you go. In reality, it is the ability to think on your feet, adapt to changing circumstances, and develop effective solutions using the knowledge, experience, and information available in the moment. In contract negotiation, improvisation is built on preparation, experience, and a dose of courage.
A Redline Tells You What. A Conversation Tells You Why.
Recently, I participated in a contract negotiation where the other party deleted an entire provision.
I could have immediately defended the clause. Instead, I asked a simple question:
“Can you help me understand the concern you’re trying to solve?”
Their answer changed the conversation.
The issue wasn’t the clause.
It was one word.
One word in the provision created a business concern that made the entire clause unacceptable from their perspective.
That discovery changed the negotiation, but it did not solve it.
In fact, it created a new challenge.
Could I replace that word without undermining the purpose of the clause? Would different language still protect my client? Would it introduce new legal or business risk? Would the other party accept it?
I didn’t stop the negotiation to consult a playbook.
I didn’t pause the call to research alternatives.
I didn’t tell the other party I would think about it and get back to them. (Though that is a perfectly acceptable response in most circumstances. However, I wanted to close the deal that day, which meant I needed to close that last issue right then and there.)
Instead, I evaluated the issue in real time, proposed an alternative word that preserved the purpose of the clause while addressing their concern, and they agreed. Think about this along the lines of proposing “reasonable efforts” instead of “best efforts.” One word can change the meaning in a way that makes all the difference.
Creating a solution in real time was the improvisation. I wouldn’t have been able to do it without substantial contracting experience, or without preparing for the negotiation and knowing the contract inside out. Or without a little bit of confidence to wash away any fears or nerves or imposter syndrome that would have stalled or distracted me from proposing the new terms.
Understanding the Problem Is Only the First Step
One of the foundational principles of negotiation comes from a book that I cite more often than any case law, Getting to Yes: Negotiating Agreement Without Giving In by Roger Fisher, William Ury, et al. In fact, I even created this spin-off guide, Getting to Yes in Contract Negotiations, that’s specific to negotiating contracts.
Step One: Understand the Why
These negotiation legends talk about the importance of focusing on interests rather than positions. Contract negotiators see this every day.
A counterparty may reject a limitation of liability clause because they’re concerned about assuming unlimited financial exposure. They may push back on an indemnity because they are uncomfortable accepting responsibility for events outside of their control. But we may not know that from the face of the markup. We may need to read between the redlines to uncover the true meaning behind the change.
Understanding that interest is essential. And I have written and talked at length about using explanatory comments and mastering live negotiations to understand the why of every ask. But it is only the first step.
Once you understand the concern, someone still has to determine how to solve it and convince the other party to agree to the solution.
Step Two: Invent Options
Another principle in Getting to Yes is to invent options for mutual gain. And that is where I see an important connection to improvisation. Once you understand why the other party objects, you still have to figure out how to solve for it. You have to take what you just learned, combine it with what you know about the contract, the law, the business objectives, and your client’s risk tolerance, and generate an alternative that might work for both sides.
Sometimes you can prepare those options in advance. Sometimes you can’t.
In a live negotiation, the information that unlocks the solution may not surface until you’re already in the conversation. That’s when the ability to generate an option in real time becomes incredibly valuable.
There is no playbook that can tell you exactly how to solve every redlining issue. Playbooks are great and extremely useful. They are a great starting point, but they are not the closer. You are.
Why Exceptional Negotiators Make It Look Easy
One of the biggest misconceptions about experienced negotiators is that they have memorized every possible answer.
Let me be real with you. They have not.
What they have developed is the ability to recognize patterns and apply underlying principles to new situations.
There is actually a name for this: adaptive expertise.
Cognitive researchers Giyoo Hatano and Kayoko Inagaki introduced the distinction between “routine expertise” and “adaptive expertise” in their 1986 work, Two Courses of Expertise. Routine experts can become extraordinarily efficient and accurate at solving familiar problems. Adaptive experts can do that too, but they can also use their underlying knowledge to develop new approaches when confronted with unfamiliar problems.
One example associated with this research is particularly interesting: abacus grand masters. Through extensive practice, they could perform remarkable calculations by mentally manipulating an abacus. Their expertise was real and impressive, but highly optimized for a particular type of task. The example illustrates an important distinction: being exceptionally proficient at executing a known process is not necessarily the same as being able to transfer that expertise to a novel problem.
Later researchers described adaptive expertise as a balance between efficiency and innovation. Experts need efficiency when familiar solutions work, but they also need the ability to innovate when those solutions no longer fit the problem in front of them.
I can’t think of a better description of master-level contract negotiation.
Routine expertise allows you to negotiate from a playbook.
Adaptive expertise allows you to negotiate beyond the playbook and in real-time.
You understand the purpose behind the provision well enough to modify the approach, generate new language, or create an entirely different solution without losing sight of the legal and business objective you’re trying to protect.
That’s exactly what happened when I proposed a different word during my negotiation. I wasn’t recalling a memorized response. I was drawing from years of contracting experience and my understanding of the provision to create a new solution for the particular problem in front of me.
In other words, I improvised.
How to Develop Improvisation
Improvisation is not an innate talent. It is a professional skill that you can develop through intentional practice. Like every other aspect of contract negotiation, it improves through repetition, reflection, and experience.
Here are five ways to strengthen your ability to improvise during negotiations:
- Learn principles, not just positions. Playbooks and fallback language are valuable, but they should never replace understanding why a clause exists. When you understand the legal and commercial purpose behind a provision, you gain the flexibility to propose alternative solutions without sacrificing the objective.
- Build your negotiation repertoire. Every negotiation exposes you to new objections, creative compromises, and different business perspectives. Those experiences become part of your professional toolkit, making it easier to recognize patterns and respond effectively in future negotiations.
- Practice explaining the “why” behind your clauses. If you can explain a provision in plain language without looking it up online, you understand it well enough to adapt it when circumstances change.
- Negotiate live whenever practical. Improvisation is difficult to develop if every negotiation takes place via email. Live negotiations require you to listen carefully, process new information, evaluate legal and business risks, and develop solutions in real time.
If the thought of negotiating live makes you uncomfortable, you’re not alone. In one of my webinars, I asked 460 legal and contracts professionals why they were hesitant to participate in live negotiations. Nearly half (45%) said they were afraid they wouldn’t know how to respond in the moment. Another 32% worried about forgetting something, while 12% feared saying something foolish.
Those concerns are understandable. But they are also exactly why live negotiations are so valuable.
You don’t develop the ability to think on your feet by avoiding situations that require it. Like every other professional skill, confidence comes from experience. The more live negotiations you participate in, the more comfortable you become responding to unexpected questions, evaluating alternatives in real time, and developing practical solutions without relying on a script.
If you’ve been relying exclusively on redlines and email, challenge yourself to step outside your comfort zone. Suggest a live negotiation call earlier in the process when it makes sense. You may discover that not only do your negotiations move more efficiently, but your confidence and improvisation skills improve with every conversation.
I’ve written more extensively about conducting effective live negotiations in my article, How to Master Contract Redlining Calls for Faster Closings and Better Terms. - Study experienced negotiators. Pay attention not only to the language they propose, but also to the questions they ask, the issues they prioritize, and how they develop solutions when negotiations take an unexpected turn. The language they use is important, but understanding how they think is even more valuable.
Don’t Be Afraid of Falling Off the Chair
Looking back, that vivid memory of tripping over a chair stayed with me long after the improv class ended. It gave me a little more confidence as I graduated from college, went to law school, and eventually found myself sitting in what felt like the scariest chair of all: the front row of a law school classroom with a Socratic method professor.
I couldn’t predict what he was going to ask me. I couldn’t script every answer in advance. I had to prepare (or be shamed if I didn’t), trust what I knew (or didn’t know), listen carefully, and respond to what was actually happening in the moment.
Sound familiar?
Contract negotiations require the same kind of courage.
You can prepare extensively, and you should. You can build playbooks, study fallback positions, anticipate objections, and understand your client’s objectives. But eventually, you have to get on the call. Eventually, someone will say something you didn’t anticipate. Eventually, the playbook will run out.
Don’t be afraid of that moment.
That’s where you grow!
The more you put yourself in situations that require you to think on your feet, the more experiences you have to draw from the next time. What once felt uncomfortable becomes familiar. What once required enormous effort becomes instinctive. And over time, you stop needing a script for every possible scenario because you’ve developed something much more valuable.
Preparation gives you the knowledge to negotiate. Curiosity helps you uncover the real problem. Experience gives you a repertoire of possible solutions.
Improvisation is what allows you to put all three together in the moment that makes or breaks the deal.
That’s not winging it.
That’s expertise.
