Understand contracts before you sign them

It's a habit I picked up from being in the music business for years, specifically being a concert promoter in my early 20's, where it's absolutely standard and normal practice to get a contract, red-line or change the stuff that doesn't apply or doesn't work for you, and return it. A good example would be striking language like "or for any other reason" at the end of a cancellation clause, or changing terms from perpetuity to 12 months, stuff like that.

I've since done it at doctor's offices, when renting or buying things, when signing a simple freelancing contract, and many other contexts. It's much less confrontational, after all you do sign it and hand it back to them, putting the onus on them to deal with it if it's a problem. I recommend this approach highly if you're the type to care.

1) The language itself.

Contracts are written in English (at least in the U.S.), so anyone with a strong understanding of English can read one top to bottom and comprehend what it is saying.

Experience in analyzing writing (like from a few college English courses) can help a lot, both in learning to quickly parse sentences, and in learning to infer motivations from the language on the page. You always want to be able to answer "why did they write it this way? What are they trying to get?"

2) What is typical and standard in contracts.

You can only get this from experience--from reading a lot of contracts--because it's often industry-specific.

For example, many software contracts, even 6 figure enterprise deals, include an ALL CAPS DISCLAIMER OF LIABILITY. THIS SOFTWARE IS OFFERED AS-IS AND WITHOUT WARRANTY. WE DON'T GUARANTEE THIS WILL WORK FOR YOUR PURPOSES, OR INDEED, WORK AT ALL.

I'm exaggerating, but not by much. This is a totally standard clause in the software industry, so whether or not you like it, you generally just have to swallow it if you want to do the deal

Likewise, most EULAs are very similar to one another. Once you've carefully read a few of them, you can quickly skim for the important bits (copyright, liability, data sharing) on new ones.

3) What the law says.

Contracts can't break the law. For example a contract that contains lies would be fraudulent. A contract that says you need to speed or drive drunk is not enforceable. A contract that says you can commit murder would not protect you from prosecution.

This is probably the hardest area to build knowledge, without going to law school. For me, it has helped to read news stories and good forums like HN. For example, I know that non-compete clauses in employment contracts are unenforceable in California, because so many people have said so.

There are some lawyers who post here--grellas for example--and AMAs from lawyers on Reddit are helpful too.

I have to disagree with you re: viability. Not only does most of our work lend itself well to automation (discovery, researching precedent, and predicting case outcomes), but this particular startup is aimed squarely at the most obvious domain where humans mostly aren't needed anymore: formulating contracts. Translating boilerplate legalese into natural language and running both parties through checklists of essential elements seems like an obvious solution to an expensive problem. I really don't see why 99% of contracts can't be automated outside of high-level practice.

Nor do I really understand your examples. I can't recall the last time anyone I know hired a lawyer to sign a rental agreement, nor do I see any reason why contract software wouldn't first check that both parties are legally competent.

Finally, I'm pretty uncomfortable with the idea that "if you automate our profession, our protectionist guild will go after you." You're not wrong, and it would be wise for LawGeex to stay wary -- of all trades, the lawyers are going to fight tooth and nail to stay relevant -- but startups like LawGeex or RocketLawyer are clearly far more in the public interest than our ludicrously expensive middleman services. We may as well ban self-driving cars because the Teamsters want to keep dangerous, error-prone human truckers.

Why couldn't that have been sent with the others? To pressure people into signing.

Heck, I've even had medical doctors insist that I don't need to read something before signing it, just "get the gist" so they can go ahead with the appointment.

Edit2: I almost think the world is designed around prodding you not to read the contract, by any means necessary, and then holding you personally responsible for it. Like, imagine parking garages. Try asking for a contract there and see what happens. Let's say you don't like the terms. Then what? They make everyone back out of the single lane entry while glaring at you? What about negotiating the terms? And good luck expecting them not to assert rights they can't legally get via contract.