I think a lot of this is simply asymmetric incentives for the lawyers. If they give legal advice that is overly conservative, it's some other portion of the business that suffers - we hire the wrong people, or we provide a worse product, or we lose out on revenue, or deals don't get made, or the code is overly convoluted, or employees get muzzled. If they give legal advice that is overly aggressive, they have to deal with the consequences when we get sued (at best) or they get fired (at worst). So they will always err on the side of caution.
I've also noticed a dramatic difference in how willing legal, HR, PR, REWS, etc. is to take risks now vs. back in the heyday of the 00s when the company was smaller and everybody felt like they were in it together. Some of that is probably simply because the company was a lot smaller and hence less likely to get sued, but a lot of it is because back then people tended to act in Google's interests a lot more while now they act in their own interests.
I've also noticed a dramatic difference in how willing legal, HR, PR, REWS, etc. is to take risks now vs. back in the heyday of the 00s when the company was smaller and everybody felt like they were in it together. Some of that is probably simply because the company was a lot smaller and hence less likely to get sued, but a lot of it is because back then people tended to act in Google's interests a lot more while now they act in their own interests.