If you don't tell your lawyers what you want, they will try to remove every problem.
Tell your lawyers you want decent terms, and you don't want to spend forever working on contracts, and have them explain the risks you face from the contract the other party proposed.
Failing to engage with lawyers and then not liking their results is like managers who fail to engage with software developers and then don't like the results. You need to tell them what you want.
I take the contract to the lawyer, discuss it with them, decide what is worth negotiating on and not. I do the negotiations. The lawyer advises.
Most contracts don't require me taking them to a lawyer. I read them 4-5 times over, annotate them with questions, talk with the client, see what we need to clarify, and go for it. Those that do involve questions I want to clarify with a lawyer before clarifying with the client (where raising a question may make me sound greedy or dramatic, etc).
Most contracts are designed to cover one or both sides in the event that something goes wrong. The boilerplate can usually be quickly identified once you have some practice. The rest is going to be operational stuff and you don't want to sign the contract to find out what is in it. These sections establish expectations on what is done and how you interact.
But whatever you do, don't have your lawyer do the negotiation for you. Madness lies that way. Business negotiations are not the same.
as technical folks, i don't think we fully understand the different types of lawyers there are.
you know that eye twitch you develop, when someone asks if you can fix their computer because you "work with computers"? it's similar for lawyers.
in my first two businesses, i didn't do enough [serious] transactions to need lawyers.
in my third business, i reviewed and wrote our initial contracts, which were eventually reviewed by other lawyers, but that took a ginormous amount of my time and sanity.
(for fellow people who suffer from impostor syndrome -- can you imagine walking into every meeting with a client and thinking "is this day i'm revealed as an incompetent contract writer?")
for the next set of contracts, i decided i needed a lawyer and got a recommendation from a friend of a friend. this lawyer turned out to specialize in immigration, not business; but assured me that they could get it done.
inevitably, in my first deal involving them, i landed in the back-and-forth lawyering described in pud's article (and so many comments here). i really needed the revenue in the company bank account sooner rather than later, so after 4 weeks, i gave in, and signed the contract, but 3 months later got burned.
this cost me time, money (both from the customer, AND the law firm), and many nights of sleep.
then i had the fortune of becoming friends with a lawyer that specializes in contract litigation. i begged him to draft my contracts, and he refused. he then explained his specialization was in tearing contracts apart, finding points of leverage for his client, and to a lesser extent, being involved in settlement negotiation (but not leading it).
to you and i, this sounds like the perfect person to draft a contract. to him, it's an unneeded source of liability that can increase his malpractice insurance rates. he did however, take a look at my originally-blessed contract and tell me to make a few changes, especially rip out the arbitration clauses in my contracts, because arbitration is hella expensive (it really is).
so today, i have a business contracts lawyer, an employment lawyer, and when needed, a lawyer experienced in business contract litigation.
and for those of you wondering about the cost, it's not that expensive.
i do a quick review of contracts i receive and clearly explain any industry-specific terms and practices to my lawyers, and have them do the final signoff.
i don't do retainers, in fact, my business and employment lawyers refused a retainer agreement. due to the new custodial laws on how lawyers must account for client money (after a few high-profile cases of attorney-client theft), they don't feel it's worth it for the limited amount of business i do. pay as you go.
Tell your lawyers you want decent terms, and you don't want to spend forever working on contracts, and have them explain the risks you face from the contract the other party proposed.
Failing to engage with lawyers and then not liking their results is like managers who fail to engage with software developers and then don't like the results. You need to tell them what you want.