If you are the CTO of Cisco you don't risk your job, because you put in 20 years kissing ass and climbing the corporate ladder, and at the end of the day you don't give a shit about e-mail servers running legacy code, you're here for the executive perks.
Exactly. And if you're Elon Musk, you run amok like a bull in a china shop, breaking everything while chasing after whatever shiny object caught your eye recently.