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Contract Negotiation Confidential: 7 Things You Didn’t Learn in Law School

A contract negotiation requires careful crafting and specialized skills. Law school may have taught you most of what you need to know, but nothing beats real-world experience. That’s why we’ve collected negotiation tips and best practices from seasoned in-house legal pros.

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7 Things You Didn’t Learn in Law School
Contract negotiations require more than facts, data, and textbook techniques. And whether you’re a new attorney or have a few years under your belt, there’s room to improve. We all know the basics – build rapport, act ethically, and communicate clearly. But as newly minted lawyers learn quickly: in-the-seat performance demands more. Sharpening your negotiation skills takes reps; there’s simply no substitute for experience. Top performers have this, but they also rely on self-taught tips and tricks they weren’t taught in law school. In this guide, seasoned lawyers reveal contract negotiation tips that won’t show up in a Contracts 101 textbook. From these conversations, we’ve highlighted seven tips to boost value, efficiency, and outcomes.
RIGHT IS RELATIVE. WHAT MATTERS IS YOUR WHY. Early in their career, lawyers often consider negotiation outcomes as true or false: Did the deal get done? But success is only as ‘real’ as your understanding of what actually matters. Business-minded negotiators understand success as what is best for a particular situation, with a particular risk level, at a particular time. They start every negotiation armed with knowledge – understanding leadership’s risk appetite, stakeholders’ desired outcomes, and a view on what matters to the counterparty. The goal isn’t to get your contract to look, feel, or sound like it ‘should’ compared to some industry standard. The goal is to deliver the value your business needed at the time. Tim Parilla Chief Legal Officer at LinkSquares.
FOLLOW THE RULE OF “3” (OR COUNT YOUR CURRENCY). Simpler, speedier negotiation (and win-win outcomes) uses simple arithmetic. Here’s how it works: assign a valuation ranging from one to three for each contract issue. For example: Three for deal-breaker issues Two for nice-to-haves One for relatively inconsequential points. Your goal is to execute the agreement quickly without sacrificing your client’s best interests. You can do this by balancing the negotiation equation. If a counterparty pushes back on three issues, assign a value to the issue based on importance and deploy your give-and-get. You may trade your 1 and 2 in order to get the 3. The practice creates a repeatable, rational routine. Of course, vets know that parties rarely negotiate on equal footing. Both parties likely want opposite outcomes. You need to know your negotiation currency (e.g., the leverage you come to the table with) and figure out if certain things are uniquely important to your client. Every party has some, but not in equal measure. Once you know what you want–and the negotiating chips you’ve got–figure out where you’ll spend it.
KEEP YOUR FRIENDS CLOSE – AND YOUR COUNTERPARTIES CLOSER. While contracts often get more attention than the people who create them, the latter brings those agreements to life. Let us not forget the vital role they play in the success of any contract. Kathy Lee, attorney and Solutions Architect at LexCheck, emphasizes pre-game planning: Have I negotiated with this counterparty before? How long did it take? What mattered to them, and why? Do your due diligence: check out their LinkedIn or ask around – any clues into the type of lawyer and negotiator they are? Once you have intel, craft your speech, language, tone, style, and documents accordingly. If you’ve worked with them before, don’t reinvent tactics. Review a previously executed agreement and ask yourself: would I accept the same terms? If so, compare the documents and send a marked-up version that looks exactly like the previous one. New things can scare people, but familiarity breeds comfort and confidence (Read: speed and efficiency).
DESIGN CONTRACTS TO DECREASE RISK, NOT DECORATE WALLS. Look up the saying, ‘You can’t see the forest for the trees,’ and you might find a picture of a new lawyer lost in contract polish mode. While crafting contracts is an art–it isn’t the type to adorn your walls. In a recent Cockpit Counsel interview, Laura Frederick, Founder of How to Contract, reminds us that the point of contract negotiation isn’t to see who has the prettiest prose, most exhaustive clauses, or fanciest language. Top negotiators told us they are maniacal in their pursuit of clarity and coherence. This means resisting the temptation to build the ‘model clause’ or impress with big words and complexity. Laura Frederick suggests seeing yourself as an emergency room doctor, not a surgeon. “The goal is triage. Figure out where risks, inconsistencies, and redundancies are and address those.” Not sure if your contracts are tight? Hunt for passive language, a telltale sign. Weak writers default to this construction because it’s easier to emphasize an action than sharpen language to define who or what is acting in the first place. Your goal is risk management, not creating beautiful documents. Laura Fredrick Founder, How to Contract.
TAKE IT EASY, SOMETIMES. Top negotiators have a dirty little secret: they know that perfect is the enemy of good enough. Frederick says there is a time to save your A-level effort for A-level risk. After years of experience and expertise, trust your gut – you’ll know when risk levels are low, and a compromise will suffice. Don’t mistake this for sloppiness. But there are times when the potential to blow up a deal is low, so it makes sense to prioritize speed. Tim Parilla also notes a caveat – “It is important to know the rules before you break them.” If you’re new to contract negotiation, build some experience before you loosen things up too much.
TRAIN TO YOUR TONE (AND OUTMANEUVER YOUR OUTBURSTS!) Stress, trauma, and fear deplete emotional resources and increase the likelihood of angry outbursts. So keep an eye out for terse, condescending, passive-aggressive, patronizing, or snappy language – particularly in impersonal mediums like email, messaging, and redlines. The best negotiators don’t fall into “us vs. them” battles. When tough pushback is required, they show self-control to write–then wait. According to Above The Law: “Once you’re in a relatively calm space, ask yourself, ‘What is the desired outcome?’ Look at the situation from a long view. We can often get completely lost in details that ultimately don’t make much of a difference.” “Come back to your comments and conveyances,” urges Frederick. “Make sure your posture and tone add momentum, not friction. Assess whether you’re embarrassing or undermining someone.” When negotiations get prickly, “Pick up the phone and call your legal counterpart without business stakeholders or anyone else on the line. Find out exactly what they want and why,” shares Tim Parilla. “Sometimes, you’re making a big deal about nothing.”
USE SMART TECH, SMARTLY. Most in-house lawyers get saddled with hundreds of contracts to review. The experts just handle them differently. Once they understand deal must-haves, they immediately (and ruthlessly) eliminate duplicative work. For better contracting, LinkSquares and LexCheck trust in the power of technology like automation and AI for drafting, reviewing, negotiating, executing, and managing success. One example: LexCheck’s contract acceleration and intelligence platform takes less than five minutes to deliver first-pass redlines on incoming contracts, including contextual comments, insertions, and deletions. The AI-powered contract review software tirelessly evaluates every agreement and catches deviations from the user’s preferred position in minutes.
LinkSquares’ Contract Lifecycle Management (CLM) platform also incorporates AI models to support smarter contracting. One AI-powered capability, Smart Values, surfaces hard-tofind terms, dates, and information so teams understand their legal commitments without manual research and reporting. AI also supports capabilities around document organization and updates given rapidly-evolving legislation, compliance, and regulatory requirements. To learn more about LinkSquares, check out our website. To learn more about LexCheck, you can find information here. Every attorney has 24 hours in a day. But the smartest, seasoned ones seem like they get a few more.
ABOUT LINKSQUARES LinkSquares helps legal department leaders drive innovation, reduce backlog, lower costs, increase revenue, and minimize loss. If you’re ready to adopt the most effective solutions for the legal function—and harness cutting-edge artificial intelligence to improve every aspect of your department–then contact LinkSquares today. ABOUT LEXCHECK LexCheck believes growth accelerates when companies agree faster. Our contract acceleration and intelligence platform streamlines negotiations by delivering redlines and issues lists in minutes while ensuring consistency across each contract reviewed—saving time and reducing risk. Businesses with LexCheck flow faster.
Contract Negotiation Confidential: 7 Things You Didn’t Learn in Law School