If you work for me you find out pretty quickly that I am passionate about the correct use of apostrophes. It’s not that hard. But people seem to struggle.
Successful businesses often question the status quo and challenge commonly held beliefs; this is part of progress. But you mustn’t let this become an excuse for challenging all culturally held norms, like grammar.
If a manager presents a status quo questioning proposal to me but it’s full of grammatical mistakes, then the mistakes distract me from the main idea and I’m less likely to think it’s a good one.
If you want to challenge cultural norms and you want people to take notice, then get very clear about what you’re challenging, and what doesn’t need to be challenged and should be conformed with.
If someone’s stepped in dog shit and they are oblivious to it then it’s hard to hear what they’re saying.
(I should know, I lost my sense of smell in a head injury so am at high risk of being oblivious to poo on my shoe.)