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Take such a term in a work contract:

During and after the term of this agreement, you will not make any defamatory or disparaging statements, whether written or oral, regarding the Company, or any of its current or former officers, directors, stockholders, partners or employees.

Is there some kind of implied limitation, such as it has to relate to the work? For example if an employee who signed this comments on a picture on social media that someone is wearing an ugly shirt and that person happens to be a stockholder, would this term be breached? How would the person signing it even know if a person they are making a disparaging comment about fits in one of the above categories?

What if it's a matter of fact, like the company was late paying it's employees (assuming this was true). What if it's a matter of opinion like "I wish I didn't have to wear a tie to work". I guess if a company wishes to enforce this term they would have to prove damages to be given compensation?

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What exactly do Non-Disparagement agreements cover? Is there some kind of implied limitation, such as it has to relate to the work?

Black's Law Dictionary defines disparagement [of Goods] as "A statement about a competitor's goods which is untrue or misleading and is made to influence or tends to influence the public not to buy". This gives a basis for inferring the scope of disparagement of a company itself (rather than just of the goods and services it provides), and how it applies to the scenarios you outline. Not every negative statement about a company or its agents meets the definition elements of (1) competition, (2) falsehood, and (3) deterrence of [potential or actual] counterparties.

an employee who signed this comments on a picture on social media that someone is wearing an ugly shirt and that person happens to be a stockholder

An opinion on social media regarding someone's ugly shirt clearly fails these three elements unless the company is in the business of producing/marketing that type of shirts. Even if that is the company's business, an actual opinion is not a fact, and therefore it is not susceptible to a test of veracity.

How would the person signing it even know if a person they are making a disparaging comment about fits in one of the above categories

Unreasonable clauses are stricken as null and void, and in many contexts it is unreasonable to expect an employee to guess or know all of the "current or former officers, directors, stockholders, partners or employees" at the time of making his statement.

What if it's a matter of fact, like the company was late paying it's employees (assuming this was true)

A truthful, non-exaggerated statement about the company's belatedness is not actionable because it is not false or misleading.

What if it's a matter of opinion like "I wish I didn't have to wear a tie to work"

It is extremely unlikely that such statement of opinion harms or tends to harm the company at all. For instance, no employee would leave the company only because you don't like wearing a tie at work. Nor would your preference discourage candidates from joining the company. What could discourage them is the underlying obligation to wear a tie, not a person's opinion about that obligation.

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    What is your basis for saying that something has to be false to be disparagement? Here’s an example of many quotes about it that indicates otherwise - “Disparagement includes truthful statements about the company, while defamation only covers false statements” zippia.com/advice/non-disparagement-clause
    – SegNerd
    Mar 6, 2022 at 21:19
  • @SegNerd "What is your basis for saying that something has to be false to be disparagement?" What I quoted from the Black's Law Dictionary is clear in that the statement has to be "untrue or misleading". Likewise, Hurlbut v. Gulf Atlantic Life Ins. Co., 749 S.W.2d 762, 766 (1987) states that the plaintiff "must plead and prove the falsity of the statement as part of his cause of action" as opposed to a claim of defamation, where falsity is presumed. By contrast, the article you quote provides no sources for its proposition. Mar 6, 2022 at 21:54
  • @SegNerd Apropos of the article's mention that non-disparagement clauses are enforceable in California, also Goldic Technology, Inc. v. Maxmile Corporation, CA Court of App., Dec. 2008 cites authorities in the sense that "'disparagement' requires a falsehood to be actionable". Mar 7, 2022 at 11:56
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Ultimately, the extent to which it applies to individuals affiliated with the company, rather than the company itself, is a matter of contract interpretation to be determined in light of the intent of the parties.

Reading in a requirement that there be some nexus to the company, or to something learned from interactions with the company is plausible, but not certain.

For example, if, three years after termination of employment you note that someone hired by the company after you left it at a private birthday party looks ugly, I doubt that a court would be willing to find you in breach of the contract.

It would be resolved on a case by case basis in light of all of the facts and circumstances.

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