Cressida is not really suited for that kind of calculating existence of briefing and counter-briefing.
They did not strike her as calculating or devious; maybe a bit hapless.
With his own colorful past as a criminal defense attorney for the Mob, he is smart, calculating, and crazy as a fox.
1710, "carrying out calculations," present participle adjective from calculate. Meaning "shrewdly or selfishly seeking advantage" is attested from c.1810.
1560s, "to compute, to estimate by mathematical means," from Latin calculatus, past participle of calculare "to reckon, compute," from calculus (see calculus). Meaning "to plan, devise" is from 1650s. Replaced earlier calculen (mid-14c.), from Old French calculer. Related: Calculable.