Can you clarify if the check in questions are randomised between social/practical/life etc. over time?
You can set your own custom check-in questions depending on the team. They are not random but you need to schedule them. You can set some them to be weekly questions and some of them daily questions.
Just from looking at your own check ins above, a vast majority of them are highly technical in nature, so I am thinking that while your core development team will get a lot out of them and it will open discussion with them, how do your other staff members who are, say, in administrative or support roles feel about them?
David (the author of the article) is a developer so he is in one team with the other developers. But he is also a manager in the company who I suspect has some administrative responsibilities which he can communicate with all of the employees in the whole company. (I am not part of Basecamp team so I imagine these things.)
Basecamp is highly customizable. It allows you to group communication by teams and project so people to not be flooded with information they do not need.
So, the support team, the administrative team and the programmer’s team can have their own place for communication. If it is needed the whole company can have a global place for communication where everybody participates.
So the check-ins which the article talked about will be sent only to the employees who are part of the same team or project.
I may have tried hard to explain but the best option is you to try it yourself. Here is a link you can use to try Basecamp https://3.basecamp.com/r/19ar0. (This is affiliate link through which you’ll save $50 from your first month with the Basecamp service.)