Key Takeaways:
- As AI takes over the mechanical side of redlining, your ability to negotiate live is the skill that will set you apart.
- Walking into a negotiation call prepared means knowing your issues, your counterarguments, and your walk-aways before the meeting starts.
- Live co-drafting is the single most powerful skill you can develop as a contract negotiator.
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There is a quiet irony happening in contracts right now. The more AI takes over the mechanical work of reviewing drafts, issue-spotting, and proposing markups, the more important your human negotiation skills become. AI can mark up a contract in minutes. But it can’t pick up the phone and close a deal. Only you can do that.
For years, lawyers and contract professionals have leaned on email as the default channel for negotiation. Send the redlines > wait for a response > reply to the response > repeat. This back-and-forth can drag on for weeks, and at some point, it stops being negotiation and starts being correspondence.
If you want to move deals forward faster (and in a world where AI is handling more of the routine work, speed and relationships are your competitive edge) you need to get comfortable with live negotiation calls.
I discuss this skill and related best practices in my book Contract Redlining Etiquette. Rule #4 is to run your contract negotiation call like it’s an important business meeting. This article builds on that principle with updated guidance for the way we negotiate today. Where AI tools, virtual-first environments, and faster deal cycles have raised the bar for what a great negotiation call actually looks like. And mastering this skill is what will set you apart from the rest.
When to Move from Email to a Call
Email works well for straightforward exchanges where the issues are isolated, the positions are clear, and the path to resolution is obvious. But there comes a point in most negotiations where the email thread becomes more of a distraction than an asset. When you notice that comments are getting longer, positions are becoming entrenched, or the same issues keep cycling back without resolution, that is your signal to get on a call.
To understand when to move from email exchanges to a live call, let’s start with Rule #3 of Contract Redlining Etiquette. The guidance here is that you should have one email exchange and then switch to a live negotiation call.
The goal is to use email exchanges strategically, not exclusively. Limit the number of back and forth emails as much as possible between contract initiation and execution. If you find yourself caught in an email exchange trap, that is usually a sign of a deeper issue, such as poorly drafted redlines, misalignment between business and legal, or an uncooperative counterparty.
A live call is often the fastest way to get to the bottom of it.
Here’s why. Email creates distance. A call creates dialogue. Some issues simply cannot be resolved by trading written positions. They need a real conversation where tone, context, and give-and-take can actually happen.
One of the most common reasons negotiation calls stall is that the person on the call does not have the authority or knowledge to say yes. Fix that before the calendar invite goes out. When you schedule the call, be intentional about who is in the room. Never include more people than necessary. At a minimum, you want legal and business counterparts from both sides, and any subject matter experts, such as someone from security or privacy if those terms are on the table. A good benchmark is no more than six people on a standard commercial contract call. More than that, and the call becomes a committee, not a negotiation.
Preparing for the Call
Preparation is where negotiation calls are won or lost. This is not unique to contract redlining calls. In fact, this is backed by negotiation science. As negotiation expert William Ury, co-author of Getting to Yes, put it: “Preparation is the single most important thing you can do to achieve a satisfying agreement.” Contract negotiations are no different.
How can you get ready? Here are a few tips that have worked well for me.
- Block time immediately before the call to review the open issues. Not the night before. Not an hour before while you are doing something else. Sit down right before the call and go through the redlines with fresh eyes. Know which issues are the sticking points, which are routine, and which ones you can concede quickly to build goodwill for the harder conversations.
- Know your counterarguments before you need them. For every position you are holding, have a reason. For every position you are willing to move on, know what you want in return. If you have access to AI tools, use them here. Run through the open issues, ask for counterarguments to your positions, and stress-test your logic. Some negotiators also use AI to simulate the other side’s likely responses so they can prepare rebuttals in advance. Think of it as a negotiation table you build before you sit down at the real one.
- Most importantly, plan to own the call. Even if you are the party receiving the redlines. Even if the other side is more senior. You’re prepared. You know the issues. And that sets you up to get more yes’s than the other side. Of course, owning the call does not mean being aggressive. It means being organized, keeping things moving, and making sure the call ends with clarity on every open issue.
Running the Call
You’ve done the prep. Now it’s time to show up and run the call with the confidence and structure that moves things forward.
Set Up Your Workspace for Success
Before anyone joins, make sure your setup is working in your favor. Two screens are ideal, one for screen-sharing the redlined document and one for your notes or internal chatbot. You should have the latest redline document and any related agreements already open and ready to pull up at any moment. Nothing kills momentum on a call like saying “hold on, let me find that.”
When you share your screen, share only the application, e.g., Word, not your entire screen. This keeps the call focused and professional, and it prevents the other side from seeing anything you did not intend to show. For the lawyers who are reading, this is how you preserve attorney-client privileged conversations like an internal business client messaging you on Teams saying, “we can’t agree to that assignment restriction because of our pending acquisition.” For the negotiators in the room (aka all of you reading this), this ensures you are not leaking valuable leverage, such as when procurement messages you saying, “we’re ok with their SLA even though it’s lower than our standard.” No, no you’re not. We can do better!
Structuring the Discussion
The most important decision before kicking off the call is to decide who will run or own the call. Ideally, this is the legal person who drafted the most recent redline version. The reason is that that person knows the redlines and understands the open issues best. On the other hand, I always like to run the call regardless of whether I prepared the latest redlines or am responding to them. That’s because I know how powerful it is to be a negotiation leader. When you own the call, you control the pace, the framing, and the order in which issues get addressed. You decide where to spend time and where to move on. That kind of structural control is a form of leverage that most people underestimate. The person running the call is not just a facilitator, they are shaping the outcome.
I’ll usually open the call by building rapport, including introductions, a brief conversation about where we live and the weather, and pulling from other things I might observe, like books in the background that I’ve recently read, etc. This really helps set a collaborative tone before the hard conversation begins. People negotiate differently with someone they feel a genuine connection with, even a brief one. A minute of warmth at the top of a call can save you thirty minutes of friction later.
Then, I will transition over to the purpose of the call – the redlines. “Thank you all so much for your time. We’ve had a chance to review your latest redlines. I can share my screen and walk us through the open issues from top to bottom. Our goal for this call is to resolve all of the open items so we can sign by the end of this week. How does that sound?”
Live Screen Sharing
The person leading the call should share the latest version of the redlined document. If that is you, have it open and ready to go before you start the meeting.
There are two approaches to structuring a negotiation call, and the right one depends on your situation.
The first approach is to go through the document top to bottom, covering every open issue in order. This is especially useful when the counterparty has not been responsive over email, or when they have been providing redlines without any explanatory comments. A top-to-bottom walkthrough gives you a chance to get context on each issue directly from the source, which you simply cannot get from a markup alone. When you kick off the call, try something like: “I was thinking we can go from top to bottom and cover all of the open issues. I’ll screen share, take notes throughout our call, and then send over an updated draft afterwards.” That one sentence sets expectations, establishes you as the driver, and signals that something concrete will come out of the conversation.
The second approach is to focus only on the major issues. This is better when time is limited, when the call includes senior stakeholders who do not need to weigh in on every clause, or when you need to close out a deal urgently and the smaller items can be handled by email afterward.
Know which mode you are in before the call starts, and communicate it clearly at the top. “Today I want to focus on the three issues we have not been able to resolve via email that I’m confident we’ll be able to resolve on today’s call: limitation of liability, the indemnification carve-outs, and the audit rights clause. Does this approach work for you?” That framing saves time and signals that you are there to solve problems, not just talk about them.
Taking Notes That Actually Matter
Notes on a negotiation call serve one purpose: making sure nothing gets lost between the call and the next draft. The format matters less than the discipline. Good notes also protect you. When someone comes back after the call claiming they never agreed to something, your documented record of decisions made in real time is your best defense.
If you are comfortable multitasking, take your own notes. If the call requires your full attention, which it often does on high-stakes issues, bring someone from your team whose sole job is to capture decisions, follow-ups, and action items. You can also use AI note-taking tools like Otter.ai or Fireflies, but if you do, keep a few things in mind: confirm the other party is comfortable being recorded, review the transcript before acting on it since AI transcription is good but not perfect, and always annotate key decisions yourself rather than relying entirely on auto-generated summaries.
One of the most effective places to capture decisions is directly in the margin comments of the redlined document. As you resolve issues on the call, drop a comment into the relevant clause: “May 1st – Agreed to remove this provision on call” or “Counterparty to provide revised language by EOD Friday.” This creates a living record inside the document itself, which makes turning the call into a clean draft much faster.
Live Co-Drafting: The Skill That Changes Everything
If there is one skill that separates good negotiators from great ones, it is live co-drafting. This is the practice of editing the contract language in real time, on the call, while both sides are watching.
It sounds simple. In practice, it is one of the most underused skills in contract negotiation and one of the most powerful.
Here is why it works: instead of one party going offline to revise language and sending it back days later, you resolve the issue right there. You type, they react, you adjust. In five minutes you can close out an issue that might have taken two more rounds of email. It is the fastest way to collapse a negotiation cycle.
The hesitation most people have is performance anxiety. People are watching you type. You might make a typo. You might draft something imperfect on the first try. Let that go. A small typo is not a sign of weakness. It is a sign that you are working in real time and moving things forward. The other side is not judging your typing speed. They are watching you get the deal done.
Start small if you need to. On your next negotiation call, try live co-drafting just one clause. Get comfortable with it. Then do two. Over time, it will become your default mode, and you will wonder how you ever closed deals any other way.
After the Call
The call is not over when you hang up. What you do in the next hour determines whether the momentum you built carries over into a closed deal or dissipates into another round of email limbo.
Finish the redlines immediately after the call while everything is fresh. Do not wait until tomorrow. Incorporate all the decisions that were made, flag anything that still needs resolution, and send the draft back with a clear summary of what was agreed and what remains open. Rule 4 puts it simply: before you hang up, confirm who is turning around the next draft and by when. Make sure you leave every call with that answer locked in.
Your follow-up email should do three things: confirm what was decided, list any outstanding action items with owners and deadlines, and state the next step clearly. Here is an example of what that looks like in practice:
Hi [Name],
Thank you for a productive call today. Per our discussion, here is a summary of where we landed:
Agreed: [List of resolved issues] Open: [List of items still outstanding, with owner and deadline]
I have updated the agreement to reflect our agreed positions and have flagged the open items for your review. Please send me your revised language on [open issue] by [date] so we can turn around the final version.
Our goal is to have this signed by [date]. Please let me know if anything is blocking that timeline.
[Your name]
Short. Specific. Clear on next steps. That is all it needs to be.
If there is a hard deadline you are working toward, name it. If you are hoping to wrap things up by end of quarter, say so. Giving the other side a timeline creates accountability and signals that you are managing this deal, not just responding to it.
Using AI to Support the Negotiation Call
AI is not just changing how contracts get drafted. It is changing how you can prepare for, run, and follow up on a negotiation call.
To get started, first check out my Guide to AI Prompts for Contracts. Plus, here are some more practical ways to put AI to work during a contract negotiation.
- Create a business summary of the open issues. Before the call, ask AI to generate a plain-language summary of the open issues, written for a business audience rather than a legal one. Share it with your internal business clients ahead of time so they arrive informed and aligned. This reduces the chance of your team contradicting itself on the call and ensures everyone understands what is actually at stake in each open item.
- Simulate the other side’s arguments. Give AI your position on a contested clause and ask it to argue the counterparty’s side. This kind of pre-call simulation helps you anticipate pushback and sharpen your counterarguments before you need them.
- Build a negotiation prep table. Use AI to help you map out each open issue alongside your current position, ideal outcome, fallback, and walk-away. Going into a call with that level of clarity is a meaningful advantage.
- Use AI note-taking tools during the call. Tools like Otter.ai, Fireflies, or Microsoft Copilot can capture the conversation in real time so you can stay focused on negotiating rather than split your attention between listening and writing. If you use one, be upfront about it at the start of the call. Most people are comfortable with it, and the disclosure keeps things professional. Pro tip: AI transcription is accurate but not perfect, and a misheard word in a legal context can matter. Always treat the transcript as a starting point, not a final record.
- Draft your follow-up email faster. After the call, use AI to turn your notes and transcript into a clean summary email, complete with agreed positions, open items, and next steps. What used to take 30 minutes can take 5.
- Convert margin comments into a structured summary. If you took notes directly in the document during the call, AI can help you pull those into an organized action item list quickly and accurately.
One thing AI cannot do is read the room. It cannot tell you when someone’s tone shifted, when a concession landed well, or when the other side is more flexible than their words suggest. Those signals are yours to catch. The goal is to use AI to handle the administrative weight of the call so your full attention stays on the negotiation itself, where it belongs.
AI is not going to replace the skill of negotiating live. If anything, it is going to raise the stakes for those who have it. As the mechanical work becomes automated, the differentiator will be the professionals who can step out from behind their inboxes and close deals in real time. That is what mastering the negotiation call is really about, and the good news is that every call is a chance to get better at it.
Learn More: Grab a copy of Contract Redlining Etiquette to learn how to leverage the power of redlines for faster and smarter contract negotiations.
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