How to use Apple Watch to approve administrator actions?

I use a separate user and administrator account as per best security practices. My user account is linked to my Apple ID. My administrator account is not. I have an Apple Watch.

When I perform some action that requires administrative rights, I get a dialog like this:

However, if I approve the action on the watch, it fails, and I have to enter the password anyway.

How can I get this to work? Or, if not, how can I get it to stop offering this dialog? Is anyone else seeing this?

It seems like a bad idea to me to link two different accounts to the same Apple ID, which is why I haven't done that.

This problem is not new with Catalina.