Leverage in a contract negotiation is rarely about who shouts loudest. It comes from preparation, from understanding what the other side actually needs, and from knowing what your own client can live with. Most lawyers were never taught any of that in law school, and the gap shows up the moment a redline comes back looking unreasonable.
How to Contract host Laura Frederick led the conversation with Tiffany Bui LeTourneau, Partner at Apogee Law, and Aaron Baer, who runs a boutique commercial law firm in Canada. Tiffany brought the in-house counsel's playbook for diagnosing constraints and packaging escalations. Aaron brought the outside counsel's view on psychology, drafting habits, and how to manage clients who can only operate at 30,000 feet. Together they framed leverage as the product of curiosity and preparation rather than aggression.
The conversation covered diagnosing the counterparty's constraints, mapping their fallback options, stress testing your asks against what the other side can actually deliver, deciding non-negotiables in advance, and packaging escalations so the decision-maker can actually decide.
Here are our top ten takeaways from the speakers' comments during the webinar:
Leverage starts with people skills, not legal skills. Negotiation is a people skill that runs on top of legal knowledge, not the other way around. Going in adversarial and trying to win clause by clause does not close deals. Understanding what the other side actually needs and where their interests meet your client's is what creates room to move. The goal is the deal, not the points scored on the call.
Get curious instead of getting defensive. When the counterparty takes a position that looks unreasonable, the right move is not to push back harder. It is to figure out why. The phrase "help me understand" is one of the most effective negotiation tools we have because it surfaces whether the position is regulatory, operational, preference-based, or a scar from a past deal. Each of those calls for a different response.
Diagnose the counterparty's constraints before you draft the response. Regulated industries, public companies, and counterparties with their own internal stakeholders often have hard constraints that look like positions. Ask the client, ask the counterparty, check their public statements, and tap your network. There is nothing more persuasive than the counterparty's own published words showing they have flexibility their lawyer is denying.
Lead with the blemishes. When something is genuinely non-negotiable, name it at the start and explain why. Saving it for round four wastes everyone's time and damages credibility. Tiffany said this earns credibility and keeps both sides from chasing solutions to problems that cannot be solved. It works best when it is one or two items, not ten.
Map the counterparty's plan B and test it. Aaron said he is less interested in the academic exercise of BATNA than in pressure-testing whether the counterparty really means their position. If they do, what is your client willing to do about it? Are they willing to walk? Knowing your own answer to that question is leverage. Negotiating without knowing it is lawyering in a vacuum.
Negotiation is psychology, so read the psychology books. Laura and Aaron both pointed to Robert Cialdini's Influence and How to Win Friends and Influence People as more useful than the standard negotiation playbooks. Anxiety drives a lot of behavior on the other side. If you can identify the underlying fear, you can usually find a way to manage it that does not require giving in on the substance.
Stress test your asks against the other side's operational reality. An ask that looks clean on paper can be impossible to operationalize. Flow-down obligations to subcontractors, custom security terms, audit rights against hyperscalers. These can all create permanent gaps between contract and reality for the vendor. Knowing what the other side can actually deliver, and proposing the next-best alternative, moves deals faster than insisting on the ideal.
Explain your changes when you send them. Aaron said sending redlines without explanation is one of the most frustrating habits in contract negotiation. When you send a draft, walk the other side through your reasoning in comments or in a short video. People agree to more when they understand the why, and even when they disagree they can tell you what specifically does not work, which moves the conversation forward. A clause changed back twice is the signal for a business conversation, not another redline.
Use a stoplight framework to track each client's sensitivities. Tiffany said she kept a red, yellow, green map for each client showing where they were flexible and where they were not. That prep work compounds over time. The first deal with a new client takes the most effort. Every subsequent deal benefits from the framework already in place.
Assume good faith when the redline does not match what was agreed. When a counterparty agrees to something verbally and sends back a redline that says something different, the reflex is to assume bad faith. Almost always it is something else. A business-to-lawyer communication gap, a change of mind nobody articulated, or unclear notes on your own side. Aaron said he screws this up himself when his notes from the call were unclear. The right response is to flag the mismatch, ask for a conversation, and skip the moralizing.
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