Key Quotes:
- “The incentives aren’t aligned, in my opinion, with liability caps. It just begs the other side… to maybe engage in some shenanigans with the data because the penalty is capped” ~ Sterling Miller, COO & General Counsel, Hilgers PLLC
- “One of the most traumatic things you can impose on your business is litigation related to trade secrets. … The best way to keep something secret is to actually not share it.” ~ Olga Mack, CEO, TermSout
- “The non-standard NDAs are not quite ready for the AI world yet. But… an AI can still be your friend when it comes to brainstorming what are the issues… flagged for you what are the risks, how to produce suggested edits, what will the counterparty respond, and how you should respond to the counterparty.” ~ Jessica Nguyen, Head of Contract Nerds & Deputy General Counsel, Docusign

The modern legal landscape is witnessing a shift where routine non-disclosure agreements (NDAs) are increasingly automated, leaving practitioners to focus on high-stakes, non-standard provisions that require sound judgment and strategic redlining and negotiation tactics.
A party’s NDA terms and how they handle its negotiation are strong signals of how the relationship will be managed post-signature.
In a recent Contract Nerds webinar on “How to Draft, Review, and Negotiate Non-Standard NDA Terms,” I sat down with a panel of experts to dissect the “landmines” of NDA negotiation. The session featured Nada Alnajafi (Founder of Contract Nerds, Sr. Corporate Counsel & Lead Legal Ops at Franklin Templeton), Olga Mack (CEO of TermScout), and Sterling Miller (COO and Senior Counsel at Hilgers PLLC). We discussed the specific NDA landmine terms that often reduce deal speed and efficiency, and how to address them from an expert legal lens.
First, understanding where deals get stuck is critical for any legal team aiming for efficiency. When we polled our audience on which clauses most often slow an NDA from sign to signature, the results were telling. Nearly 44% (282 out of 642) of respondents said that indemnity clauses in NDAs are a common cause of slow review cycles, and 29% (195 out of 642) said privacy and security terms were the culprit.
Poll Question: Which clause most often slows your NDAs from getting signed?

This data highlights a significant tension: while we strive for velocity and operational efficiency, nearly half of us are bogged down by indemnity debates and another third are bogged down by privacy and security discussions for a contract that represents a potential business relationship that should be a straightforward confidentiality exchange.
This makes Clausey, the Contract Nerds logo, very sad.
Below are three key takeaways from this educational and engaging webinar. I recommend watching the full webinar recording to dive deeper into this topic.
Takeaway #1: Skip Non-Standard NDA Clauses to Preserve Deal Velocity
In the context of routine deals, non-standard NDA clauses like residuals, non-solicitation, or indemnity and limitation of liability language creates unnecessary friction and business risks (of slowing down or losing a deal) rather than offering necessary legal protection. Emphasis on necessary.
Ask yourself: What are the odds your organization would bring litigation over the information shared in these discussions? For the routine deal where the same presentation is shared with thousands of prospects, my guess is the odds are low.
I noted during our discussion, “standard NDAs can be handled by the business, oftentimes, because they require very little edits or negotiation.” Olga Mack, CEO of TermScout, emphasized that mutuality is the ultimate tool for velocity, stating that “enabling your sales team to sign NDAs as they are in conversation is the most powerful way to support business and become friends with everyone there.” Sterling Miller, COO and General Counsel at Hilgers PLLC, often the skeptic of these complex terms, warns that “it’s hard to justify giving someone an audit right at the NDA stage,” suggesting that practitioners should focus on the context of the transaction. Nada Alnajafi, Founder of Contract Nerds and Sr. Corporate Counsel & Lead Legal Ops at Franklin Templeton, reminds professionals that “a lot of these triggers are in NDAs because someone on the other side doesn’t understand that it’s too premature to have them at this stage,” advocating for more appropriate templates like POC (proof of concept) agreements when necessary.
According to 42.79% of legal and contracts professionals polled during the webinar, when an NDA is shared at this early stage of the relationship, they are optimizing for getting it signed without legal review or negotiation and including non-standard terms run contrary to this goal. Shout out to the 34.75% of folks who quietly worry while still appearing easy to work with – we see you.
Poll Question: When you send an NDA, what are you optimizing for?

Takeaway #2: Don’t Overlook Term, Termination, and Trade Secret Language
Precise language is required to distinguish between the duration the NDA is in effect, the survival of general confidentiality obligations after the NDA expires or terminates, and the indefinite protection of trade secrets (if any are shared). Many standard templates mistakenly terminate all obligations after a set period with vaguely written terms and termination language, potentially leaving sensitive information unprotected.
Miller pointed out that “there’s nothing that says, after 3 years or 5 years, confidential information loses its confidentiality,” which is why he favors long survival periods for a receiving party’s confidentiality obligations after an NDA terminates or expires. To avoid long-term liability, Mack suggested that practitioners “balance velocity with protection” by considering whether certain survival terms belong in the NDA or the main services contract.
I wondered: Does AI understand this distinction in NDA term and termination language? We put AI to the test and I performed a live demo of Docusign’s AI Assisted Review on a sample NDA to test whether AI is capable of understanding and catching whether the NDA has sufficient survival of confidentiality obligations post-termination per my contract playbook – spoiler: it does! AI was able to catch non-conforming language and it even suggested redlines to the language to make the NDA conforming. I encourage you to use AI as your first pass NDA review buddy, but, of course, ensure you check its output.
Takeaway #3: Define “Reasonable Standard of Care” in the Age of AI
As AI tools become ubiquitous for recording, summarizing, and analyzing meetings, emails, documents, and other content, we discussed what the “reasonable standard of care” meant for the receiving party’s obligation to protect confidential information. This language is commonly found in all NDAs, and it’s also commonly undefined.
If appropriate given the nature of the information shared and associated risks, disclosing parties should now consider and potentially define the standard of care and also verify with the receiving party whether: (1) their data will be used to train AI models (either the receiving party’s models or a third-party’s model); (2) the AI tools used by the receiving party meet the disclosing party’s policies and requirements; and (3) the disclosing party’s information will reside within secure enterprise environments.
I suggested that the most effective mitigation is ensuring that receiving parties use enterprise versions of AI tools that do not train on inputted data. Miller noted the educational role of the lawyer in this new era, stating that “pointing that out specifically in these early days of AI, maybe, is smart” to ensure the other side realizes that running data through a public LLM could constitute a breach of the NDA. Alnajafi viewed these clauses as conversation starters, noting that “it’s a way to catch it, to force a discussion that maybe hasn’t happened yet… because all the processes of incorporating AI… is so brand new”.
The future of NDA reviews lies in shifting from routine “paper-pushing” to mastering the complex, non-standard NDA clauses that demand sophisticated legal and business judgment. As automation handles the mundane, the human lawyer’s value is found in navigating landmines—like AI-driven data leakage, ambiguous termination language, and the “philosophical” debates over residuals. By leveraging AI as a brainstorming buddy while maintaining essential human oversight, we can protect our organizations without sacrificing deal velocity. Ultimately, balancing the art of strategic protection with the science of efficiency ensures the NDA remains a high-speed engine for business growth rather than a bottleneck to innovation.
Audience Q&A Session and Beyond
These questions and more are answered by Mack, Sterling, Alnajafi, and myself in the free webinar recording.
What do you think about liquidated damages clauses in NDAs?
- Sterling Miller: On a scale of 1-10 with 10 rated as things to avoid, Sterling rates liquidated damages a “7” on his scale of things to avoid, noting that “no one will find that” acceptable in a standard negotiation.
- Jessica Nguyen: I agreed with Sterling, stating, “It’s a no for me… you’re basically putting a dollar value in the information that you will be disclosing, and then you’re also telling the receiving party how much you value that information.”
Why are AI provisions necessary if we already have standard confidentiality terms?
- Sterling Miller: Specific markers are needed because “they don’t realize that if they run it through an AI tool… they’ve just breached the NDA”.
- Nada Alnajafi: Use AI provisions in NDAs strategically “to force a discussion that maybe hasn’t happened yet, that nobody’s asked about.”
How do you handle European prospects who insist on GDPR language in a simple NDA?
- Jessica Nguyen: Suggest a simple compromise: “a very simple sentence or two, where each party acknowledges that limited personal data will be exchanged… but, each party acknowledges that the information shared is for a legitimate business interest under GDPR.”
Continued Learning Opportunities
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This webinar was made possible due to the generous sponsorship of Docusign, Intelligent Agreement Management.


















