IPA: //kælˈkjʊl.eɪ.tɪŋ.li//
KK: /kælˈkjuleɪtɪŋli/
In a way that shows careful thought and planning, often for selfish reasons.
She approached the negotiation calculatingly, considering every possible outcome.
Calculatingly → It is formed from "calculating" (from Latin "calculare", meaning to count or compute) and the suffix "-ly" (meaning in a manner of). The word "calculatingly" means in a manner that involves careful consideration or planning, often with a sense of shrewdness or cunning.
Think of someone who is 'counting' or 'computing' ('calculare') their actions 'in a manner' ('-ly') that shows careful thought or strategy.