I've only saw it, over 20 years ago, so memory is fuzzy because I was a deck up. But timing was important and you have to get the plunger up in the first try. The engineer had been on the ship for years and was immensely strong. (So much so, that when I did my first set of rounds after relieving his watch, I would carry a valve wrench to loosen the commonly used valves, so I could open them without rupturing myself.). I can't comment on how experienced you would need to be as it is something I never considered trying as I am rather attached to my various body parts and function.
It seems to me, one of the other engineers tried it and never got the plunger up and he ended up with the tool madly jumping up and down with the plunger motion.
I chose the safe route and shut the engine down which caused much angst as they lost 30 minutes out of the schedule
I should add, this was a MAN 52\55A medium speed 4 stroke, running 400 RPM, if I remember correctly