Well no, we can't know what is happening behind the scenes, that is my point. You don't know who decided what to say and whether it should be a choice. This is why I don't think anyone should be pointing fingers at any individual. Nor do I see an issue with the way it is presented. All drivers are given choices in strategy and Lando is very close to the engineers. He know what they mean and what they are getting at far better than we ever do. The fact that it was a choice between covering Max or going for the win makes clear that the team knew it was a risk and the softs may not cover Verstappen.
However, the team were expecting to come out just behind Lewis with a big old tow and immediate DRS, which would have changed this entire conversation, irrespective of whether he'd got past him. If the pit had gone well,Lando with fresher tyres on had a good chance of getting past Hamilton Quickly, getting fresh air and giving Ham dirty air, and put Ham as a buffer between Max and Lando.
Still it'd been the wrong tyre, but it would have been much less clear and the conversation about presentation non existent because the question being asked was never a problem, the problem was the data and the decision that led to a perfectly normal racing choice. And of course the pit stop the stopped us from getting DRS and a tow to at least hang behind Ham and only fight Max at the very end.
So for me the teams question, "Do you want to take a risk for the win? Do you need softs for a quick attack or meds for the long haul?" was perfectly fine. Of course you've got to ask the driver, it's nuts to think you're not going to ask the driver.
In terms of Oscar, it's appropriate that they might not have risked softs because he was cruising to 4th and had no need for that risk so the new medium was the only option, there was nothing for him to risk