This is important to always consider, as a reason that having someone with a legal background can sometimes contradict entrepreneurship:
"Note that such lies are not always illegal. Rather, the law is content to leave the ultimate question of liability to a jury, with all the expense and risk of a full trial. Of course, victims of such conduct may decide that litigation is not worth the trouble."
The reason is is that this is not strictly a legal question but also a strategy questions as well as probabilities. Also the dollar amount comes into play. A large negotiation by Boeing is the not same as a small startup or even 500 person business with a $100,000 transaction.
Another pattern I found is that CEOs with legal background tend to see contact negociations as an exercise in writing legally correct text (down to writing it themselves, even if they are not expert in that part of the law), which ends up taking far more time than negociating on the important facts and then having external lawyers formulate that out.
"even if they are not expert in that part of the law"
Agree. And what's even more dangerous is someone with legal background but not years of experience that is able to weigh, on gut, the pros and the cons of adding that legally correct text. [1] It's like the paradox of system security. A trade off between being, say 100% secure but then either opening up other potential security issues or having usability problems caused by something with a extremely small chance of happening.
[1] Here's an example. You have a tenant. You want to be able to charge them for a certain thing upon move out. You can add the exact item or you can be vague. Both come with risks. The risk of adding the text is that you bring it to their attention and they nix it. The risk of not adding it is that you may not be able to charge for it upon move out. What do you do? It's not a legal question (legal wise you would add it) it's a strategy question.
That's an interesting one. I have a another example: trying to put codify in a contract. For example, I recently had a client asking me for on-call duty on a weekend. So I quoted that and put it in the offer. (fixed fee for being on call, + a bonus for every hour worked)
Now, they were asking me whether it shouldn't be included that if I build the stuff, I would feel obliged to make sure it runs well. Sure, I do, and if the team I am working with is firefighting, I will be a good colleague. But if someone wants the right to call me at any time, they shouldn't be surprised that this has a price.
What you're selling by codifying it is the choice. You can choose, at the cost of alienating the team, to take off of any weekend firefighting. This is a valuable choice if you do something like make plans that are expensive to cancel.
If you don't have the choice, you can't make plans that are expensive to cancel, which is a real economic loss.
"Note that such lies are not always illegal. Rather, the law is content to leave the ultimate question of liability to a jury, with all the expense and risk of a full trial. Of course, victims of such conduct may decide that litigation is not worth the trouble."
The reason is is that this is not strictly a legal question but also a strategy questions as well as probabilities. Also the dollar amount comes into play. A large negotiation by Boeing is the not same as a small startup or even 500 person business with a $100,000 transaction.