I've been known to stand on top of my 4 foot Louisville (rated at 300 pounds). But that's pretty scary now so I don't do it often any more. She's a rock tho. Doesn't move period. Back to your problem.
So I'm on a job. There is a fourteen foot new/old wooden ladder on site. Now days I'll go ten steps up unless I've had a rye then 11 steps up. Can't reach.
I work by myself. Look into renting a 16 foot, - I'll put my feet on rung #12 for that guy. I decide it's too heavy/awkward for me to handle by myself.
So i tell the property management guy to phone whosit, - they have more guys and don't even have to rent a ladder. Or... he's a management company. He can call me when he has found some tough guys and has them set up a 3 section scaffold. I'll do that.
So what you have to do is look after yourself. The boss might like a hero but if you fall, your done. You owe that dork nothing and why he would expect that from you just shows his intelligence.
Oh. The property management guy did call me back. I climbed the scaffold, fixed the lights, sent an invoice got paid. I was able to walk somewhere and spend that money (I like to do that). For whatever reason he decided not to call the other company.