I won’t pretend to know your situation, but this feels wrong.
Unless your management team is full of nepotism hires or bad fits that haven’t sorted themselves out yet, it’s full of people that were in your shoes.
Re: The Bottom - YOU may be an exception, but most people on the bottom lack the confidence or sometimes critical thinking skills to deal with unexpected issues tactfully. That’s important if you want to make payroll.
If you are the exception, I preemptively congratulate you on your forthcoming promotion. :)
Signed, Fellow Bottom-Dweller
Wanting your best friend to experience something like you did for the very first time is the sole reason he’s doing this. Sure, it can be annoying, but at least it’s coming from a place of love and a hope for a common connection. He’s not trying to inconvenience you, though he may be.