It's telling him to try harder and keep cool. You push him too hard he's mental health drains faster and he starts making mistakes, but some times you have to risk it. Bobs only start overtaking without problems around lvl 35, before that they do tend to just kiss the other cars instead of overtaking.
And yes, softs are always better, and they don't ware out until the endurance races, but imo they just make races way too easy.
Thanks. I just started him in some races he'd been struggling in with simply changing to softs and he's tearing it up.