You're right that it's wild out here. I think Mrcoffee is right that you do need to think about your use case, even if you're not in a regulated industry. There are way too many examples of AI going rogue right now, and AI misuse can still get your team in trouble even if it's not necessarily with some type of federal or governmental agency.
Our team started rolling out AI across the org slowly around 2 years ago. Mostly first with enterprise and team-level ChatGPT, though now we're moving more toward Claude.
I think the primary thing you want to ensure is that you have organizational-level oversight on how the system is being used while still respecting some level of privacy for each user.
From an admin standpoint: If people are going to use Claude or what have you, have them use it under the Team account so you can have administrative access to logs. Yes, you can see everything.
How much you want to tell your team on that end is a different matter, though. What's likely to happen is this:
1. Your team will definitely take advantage of the Team-based Claude account, but they'll be highly skeptical of what you can see (since you can see everything) so they'll only use it sparingly.
2. Many will still want to use their personal Claude accounts to do work, and there isn't much you can do about that.
So, you're going to need to incentivize people to use the Team account. As you mentioned, the option for working together is a plus. Generous token availability is a huge plus versus people's private AI accounts.
Here's one thing I should note: Assume people are already using their own AI accounts to do work. You need to convince them why switching most of that to a company-owned Team account where their activity is actively available to be viewed is a better option. That's going to be the bigger challenge, but if you lean into what they can get out of it, while being transparent about what you can see, you'll get better adoption.