This website uses cookies

Read our Privacy policy and Terms of use for more information.

Most lawyers who do commercial contracts spend their careers on the deal and hand the relationship to someone else the moment it goes wrong. That handoff hides a problem. The documents the business creates while performing the contract often matter more than the contract itself, and most teams build that record badly without knowing it.

This How to Contract webinar took on that gap. Host Laura Frederick was joined by Joanna Valencia, a multiple-time General Counsel in the cybersecurity and AI space who now serves as a fractional General Counsel through Outside, and Maria Amelia Calaf, a business litigator in Austin who handles breach of contract and intellectual property disputes. Joanna brought the in-house operator's view of building records before anyone needs them, and Maria brought the litigator's view of what those records look like once they become evidence.

The conversation covered why performance documents carry as much weight as the contract itself, how to keep ordinary-course records factual and contemporaneous, how to communicate as tension builds without framing a legal dispute too early, the anatomy of a notice of default, why privilege does not attach just because counsel is copied, and why note-taker apps tend to backfire.

Here are our top ten takeaways from the speakers' comments during the webinar:

  1. The performance record can outweigh the contract. When a dispute reaches arbitration or court, the documents created during performance carry as much weight as the signed agreement, and they are often what amended the material terms in the first place. That means the emails, Slack messages, and meeting notes your team generates every day are evidence, whether or not anyone treats them that way. We should be building that record deliberately, not discovering later what it says. The contract is the easy part because it was negotiated. The performance record is harder because it accumulates without anyone deciding it should.

  2. Memorialize decisions, not discussions. A summary that says the parties discussed a timeline does nothing for us in a dispute. A summary that states what was decided, who decided it, and what the next steps are can be close to dispositive. The fix is to write performance confirmation emails as a matter of routine, because they are contemporaneous and they give the other side a chance to correct the record in real time. If they stay silent, that silence works in our favor. Five minutes of writing now replaces a credibility fight later.

  3. Keep two tracks of documentation. The internal track is where we are honest about concerns and opinions, and it should be protected as carefully as possible. The external track stays purely factual, with no legal conclusions, assertions, or admissions. Mixing them is how an honest internal note becomes a damaging exhibit. Joanna drew this line hard, and it is one of the most practical habits a team can build. The discipline is knowing which document you are writing before you start typing.

  4. Strip the emotion before you send. Write the message you want to write, walk away, and come back later to take the emotion out, whether the impulse was anger or warmth. Both put something in the record that is not a fact, and the friendly filler is just as risky as the angry line. Maria's standard for a good record is three words, contemporaneous, factual, accurate. A litigator reading the file later does not need our gratitude or our outrage. They need the facts to stand on their own.

  5. Watch your word choice, because some words are conclusions. "Vendor failed to deliver" is a legal conclusion. "I am confirming we have not yet received these deliverables" is a fact. The same goes for words like defect, breach, default, and material failure, which carry specific legal meaning and consequences. Once we use one, we have framed the situation as a legal dispute whether we meant to or not, and we cannot put it back in the box. Save those words for the moment we are ready to live with what they trigger.

  6. When tension starts, slow down and go back to the contract. The window between a minor problem and a formal default is where teams move too fast and send the first inaccurate message. The better sequence is pause, coordinate, investigate. Go back to the actual contract terms, find any informal amendments, and verify the business team's account with documentation before taking anything to the other side. The first missive needs to be accurate, because an inaccurate one hands the counterparty an easy response.

  7. Decide who sends the communication, because that itself is strategy. A message from the project manager, from in-house counsel, and from the CEO each send a different signal beyond the words. The usual default is the business team speaking in its own voice, with legal coaching behind the scenes on what to say and what to avoid. A counterparty can feel a lawyer's hand in a business person's email immediately. Choosing the sender is choosing the message.

  8. Treat the notice of default as a legal instrument with required elements. A notice of default is not a letter expressing dissatisfaction. It needs the specific provision breached, a factual description specific enough to enable a cure, the cure period stated with real dates, the remedies we intend to pursue, and reservation of rights language. Skip an element and we undermine our own remedies. It is exhibit number one in any lawsuit that follows, so it should read like one.

  9. Termination has to be explicit, never implicit. A termination cannot be implied from context or tone. It has to be stated clearly and precisely, in plain factual language, or it will not hold up. Laura's example was a team that cited the default and asked to meet but never wrote that they were terminating, and it failed as a termination right before a no-fee cancellation window closed. People can negotiate for months believing they started a clock they never actually triggered. Precision here is not pedantry, it is the difference between having a right and losing it.

  10. Stop assuming privilege, and be careful what you record. Copying in-house counsel on a business email does not make it privileged, and that is universal across all fifty states. The safer operating rule is to assume no privilege ever and train the team to write accordingly. The same caution applies to note-taker apps, because capturing informal communication verbatim creates a harder evidentiary record, not a safer one. As one litigator told Laura, whoever has the most records often loses. The smoking gun cannot live in documentation that was never created.

Subscribe to Stay in the Loop

Contract trouble is easier to handle when you have seen how other lawyers think about it. Our weekly newsletter brings you recaps like this one, plus a look at the How to Contract webinars coming up next. Subscribe now and keep the practical insights coming, whether or not you can join us live.