Technology

Maybe, but that serves as a very valuable teaching opportunity about the concept of "empty" is in Python. It's pretty intuitive IMO, and it can make a lot of things more clear once you understand that.

That said, larger projects should be using type hints everywhere, and that should make the intention here painfully obvious:

def do_work(foo: list | None):
    if not foo:
        ... handle empty list ...
    ...

That's obviously not a boolean, but it's being treated as one. If the meaning there isn't obvious, then look it up/ask someone about Python semantics.

I'm generally not a fan of learning a ton of jargon/big frameworks to get the benefits of more productivity (e.g. many design patterns are a bit obtuse IMO), but learning language semantics that are used pretty much everywhere seems pretty reasonable to me. And it's a lot nicer than doing something like this everywhere:

if foo is None or len(foo) == 0: