Most contracts get won or lost before the first redline gets exchanged. The work that happens during preparation, including understanding the business deal, mapping failure modes, pressure testing the remedies, and lining up fallback language, sets the ceiling for what the negotiation can deliver. The lawyers who skip that work spend the negotiation reacting to the document. The ones who do it walk in already knowing where the leverage lives.
This How to Contract webinar was hosted by Laura Frederick and featured Hebe Doneski, General Counsel at Symmetry, and Adrienne Valencia Garcia, Deputy General Counsel at Somos. Between them they brought decades of in-house negotiation experience from SaaS, payroll tax, telecommunications, and earlier stops in tech and litigation, which made the conversation usefully concrete about what changes a deal and what just takes up time.
The conversation covered five preparation strategies that change outcomes before drafting starts. The speakers walked through separating legal risk from enforcement risk, planning around failure modes with the business team, pressure testing the remedies that get drafted by reflex, modeling a deal across its full lifecycle, and building fallback playbooks that actually help in the room.
Here are our top ten takeaways from the speakers' comments during the webinar:
Win the deal, not the negotiation. Commercial contracts are not the same as litigation or mediation, where the goal is to beat the other side. We are looking for the best deal for both parties. That means checking the ego, as Hebe put it, and spending real time understanding the business deal rather than scoring points clause by clause. If we are winning the negotiation but losing the relationship, we are doing it wrong.
Spend prep time on the business deal, not just the contract. Hebe paid close attention to financial mechanics, including how royalties were calculated and how measurable obligations were defined. She used AI to fact-check her understanding, and she recommended a thought partner outside the deal like an accountant. We have all seen what happens when the lawyer does not understand the deal. The clauses might be technically clean and still miss the point entirely.
Separate legal risk from enforcement risk. Legal risk is about how a court would interpret a provision. Enforcement risk is about what either party can actually do under the contract to affect the relationship. Most of the leverage in a commercial contract lives in enforcement risk, but most of the drafting energy goes into legal risk. Laura's "so what" test is the fastest way to find this gap. They do not deliver. So what. What are you actually going to do about it.
Plan for failure modes before drafting. Think about the end before the beginning arrives. Hebe always negotiated tail periods in reseller agreements so she could support downstream customers if the upstream relationship ended. The reframe to use with the business team is also worth borrowing. Instead of asking what could go wrong, ask what they want to happen if a scenario occurs. That produces practical answers and gets the business doing its own failure planning rather than rolling its eyes at the lawyer.
Read the commercial documents, not just the master agreement. Order forms, schedules, and statements of work told you how the relationship would actually play out. Hebe walked through implementation, steady state, and renewal as separate phases, each with different provisions to think through. Lawyers who skipped these documents missed where most of the operational risk lived. Most of the problems we get pulled into after signing trace back to something somebody did not read.
Pressure test every remedy with the "so what" question. Hebe's non-assignment story is the canonical example. A clause she had been taught her entire career was toxic turned out to be toothless because the counterparties could not exercise the remedy. The same logic works in the other direction. Give away a remedy the other side wants but cannot use, and you can buy real concessions on the provisions that matter.
Suspension and set-off were underused remedies. Laura described suspension as way more powerful than termination because it was scary for the customer. Set-off let the customer deduct from invoices. Adrienne warned that set-off triggered vendor pushback because of revenue recognition. She called revenue recognition "the holy grail" for getting vendor attention. If you cannot get traction on a position, find a way to tie it to revenue recognition and watch the conversation change.
Build a fallback playbook with good-better-best annotations. Hebe maintained a playbook even as a team of one and used AI to mine her last 18 months of contracts for variations. For larger teams, she recommended getting everyone in a room once a year to review fallback language. Laura's warning is worth taking seriously. A bare list of past concessions handed to junior lawyers without context is a disaster. The playbook needs annotations, approval requirements for envelope-pushing language, and some explicit "never agains."
Handle AI counterparty arguments with curiosity, not pushback. Hebe said dealing with AI-generated arguments was not all that different from dealing with a person who did not fully understand their own argument. She asked for clarification or requested a redline. Adrienne agreed and stressed being genuinely curious, "not with that tone that some of us can use." Laura framed the deeper point. The people sending AI drafts usually either did not have time or did not understand the issue. Giving them a face-saving way out got better results than calling out the AI slop.
Operational risk drives more daily problems than legal risk. Hebe said she overweighted operational risk compared to most lawyers. Operational provisions were harder to draft but easier to negotiate, because you were just seeking clarity. She shared a story about a vendor audit where the metric "deployments" was never defined in the contract, leading to weeks of non-lawyers arguing about what the word meant. Laura agreed that operational issues were the bigger source of problems throughout her career. The legal risk is what gets attention. The operational risk is what eats your time.
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