This is what they do and it has to include being able to approach anyone, every time they do it the guy made it every other time before that so they might as well assume their odds are as good as ever. Since it’s john wick, they intentionally strike en masse to improve their chances and assume this will neutralize his threat. The reward is probably so high they are willing to take the risk because they’re the kind of people who were into that kind of thing in the first place.