I spent a few minutes on this and I can't figure it out.
I ran make debug, and then tried opening a Watch simulator via the "Hardware" menu of the simulator, but it wasn't paired.
I then tried running xcrun simctl list to see if I could specify a paired iPhone + Watch simulator, but I wasn't sure how to specify one on the command line.
Ideally there would be a command to do this in the Makefile if that's possible.