A leadership role calls for boldness; you can't be timid over every detail.
Tips
history
From 《淮南子·人间训》: "the sage is reverent with small things and cautious with minute ones, moving always in season." The original was pure praise; modern tone tilts critical, implying timidity.
usage
Usually mildly negative today - suggests the person is too careful to take initiative. Compare with the genuinely positive 小心谨慎.
