My sense is that, unless the barista is an idealistic leftist college student out to settle some horrible injustice in the world, very few baristas will participate in this "conversation." Especially at rush hour, they are trying to get customers through the line as quickly as possible, which won't happen if they're trying to engage every customer on the issue of race. Also, most of them won't be willing to initiate a conversation on a potentially controversial topic even if it *is* during a slow period. They don't want to upset the customers.
I don't know what the CEO was thinking when he came up with this idea... maybe it's just an early April Fools... maybe he needs to go on that undercover CEO show to be reminded of the reality of working in a customer service position.
What I've noticed about many liberal heads of corporations is that they desperately want to be seen as being on the side of the poor and oppressed...social justice and all that.
So here's a guy smart enough to accumulate close to three billion dollars, and he's mortified that he might be one of those dreaded one percenters who just don't care about the poor and oppressed. So he comes up with this thoroughly wacky idea.
Only liberals think of these things. I'll bet many of the people (fellow liberals) of the board inwardly groaned when he proposed this nutty idea.