Translation guide
The ability to judge people and situations well and make good decisions, often in a practical or self-interested way.
The ability to understand situations and people quickly and accurately, and to use this understanding to make good decisions.
Insight, perceptiveness. Refers to the ability to see into the true nature of things. Often used for intellectual or analytical shrewdness.
With his keen insight, he saw through to the heart of the problem.
Foresight, prescience. The ability to anticipate future events or trends. Implies shrewdness in planning ahead.
I'm always impressed by her foresight.
Shrewdness in a practical, worldly sense. Implies being sharp, calculating, and not missing any opportunity. Can have a slightly negative nuance of being cunning.
No one can match his shrewdness.
Keen eye, penetrating insight. A more literary or formal term for sharp perception and judgment.
His keen insight surprised many people.
The ability to manipulate situations or people to one's advantage, often in a clever and sometimes unscrupulous way.
Cunning, slyness. A common word for shrewdness with a negative connotation, implying craftiness and a willingness to deceive.
He succeeded in business through cunning.
Craftiness, wiliness. Similar to ずる賢さ but often implies a more malicious or wicked cleverness.
Cunning born of experience, slyness of an old fox. Used for someone who is shrewd in a worldly, experienced way.
I'm no match for his seasoned cunning.
The ability to make smart, often strategic decisions in professional or public affairs, with an eye for advantage.
Competence and shrewdness in handling affairs, especially in business. Often used in the phrase 敏腕家 (a shrewd operator).
He is known as a shrewd manager.
A go-getter, a shrewd and capable person. Often used for someone who is effective and clever in business or negotiations.
Business acumen, commercial shrewdness. Refers to a natural talent for making profitable decisions.
There is no single Japanese word that perfectly matches all nuances of 'shrewdness'. The choice depends heavily on whether you want to emphasize positive insight, practical cleverness, or negative cunning. Using ずる賢さ when you mean 'astute' will sound insulting.
洞察力 is about deep understanding and perception, often intellectual. 抜け目なさ is about practical, worldly sharpness and not missing opportunities. The former is more positive, the latter can be neutral or slightly negative.
You need to be on guard against his craftiness.
彼女はなかなかのやり手だ。
She's quite a shrewd operator.
彼には商才がある。
He has a shrewd business sense.