Are we really doing this again?
What if the technical director/director of football buys Player A and the manager doesn't want him? We got De Bruyne all those years ago under Emenalo and Mourinho decided he was done with him after like 5 games. The key thing is the manager and board need to work together to identify targets for the best of the club rather than one figure trying to impose themselves over the other. That is how Klopp and Guardiola have been able to operate and get the players they want at Liverpool and Man City respectively. They didn't just have the players thrown onto them to manage.
Unless we go hire a manager who primarily plays with a back 3 in the future, am not worried about whether the likes of Chilwell will fit in. He's not a system player like Jorginho. It's funny how you only mentioned Chilwell when Lampard was also the one who asked and got Ziyech, Werner and likely soon Havertz. Not worried about them being system players then?