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Definition of calculating : 1. Given to contrivance or forethought; forecasting; scheming; as, a cool calculating disposition.
2. of Calculate
3. Of or pertaining to mathematical calculations; performing or able to perform mathematical calculations.
4. The act or process of making mathematical computations or of estimating results.

Synonyms:

conniving, calculative, hard, intelligent, attitude, collusive

systematizing, gauging, computing, reckoning, quantizing, ranking, planning, concluding, deducing, thinking, presuming, summing, guessing, considering, supposing, valuing, counting, totaling, weighing, scheming, inferring, scheduling, assessing, tallying, dividing, determining, evaluating, surmising, plotting, approximating, programming, scoring, studying, rationalizing, rating, judging, multiplying, measuring, accounting, figuring, adding, enumerating, quantifying, triangulating, appraising, estimating

calibrating, surveying, testing, scaling, benchmarking

contemplating, cerebrating, imagining, envisioning, cogitating, brooding, musing, deliberating, pondering, reasoning, reflecting, speculating, concentrating, debating, daydreaming, analyzing, meditating

crafty, masterly, masterful, serpentine, foxy, smooth, devious, sharp, quick, slick, subtle, designing, wily, sly, artful, skillful, cunning, witty, slippery, deft, clever, astute, snaky, tricky, shrewd, wary, feline, canny, ingenious

Usage examples:

• Well, without calculating I should imagine it would be a very minute fraction of an inch. - "Amusements in Mathematics", Henry Ernest Dudeney.
• But in calculating that way we shall be employing what reason we have. - "Public Opinion", Walter Lippmann.
• It is not as if I were cold and calculating- so don't despise me altogether. - "The Metropolis", Upton Sinclair.