Er yes pretty much every time?
Back end of last season we largely lined up:
Dubravka, Krafth (right sided centre back or right back), Fernandez (centre back), Dummett (left sided centre back or left back), Murphy (right wing back or right winger), Ritchie (left wing back and we will say left winger but not really anymore), Longstaff (centre mid), Willock (mainly centre mid), Shelvey (centre mid), Wilson (forward), ASM (forward)
Others to play were Schar (used as centre back), Lascelles (used as centre back), Joelinton (used as wide forward or striker), Almiron (used as wide man or forward), Clark (used as left sided centre back), Manquillo/Lewis (used as full backs or wing backs), Hendrick (used mainly in centre mid), Carroll (used as striker), Hayden (used mainly as centre mid but he is a utility player anyway comfortable at centre back, full back, wide midfield).
So yeah he largely plays players in positions they are comfortable in. I mean not all of them are good players in any of their preferred positions but that is a different matter.