Scripture states: Praiseworthy is he who contemplates the needy [dal], on the day of evil Hashem will deliver him (Tehillim 41:2). This verse can be understood on several levels. We should therefore explore it, for it can teach us several aspects of chessed-kindness.
The simple meaning of the word dal, “the needy,” is simply a financially poor person who does not have basic needs. It therefore requires the “contemplation” and intelligence of the one who will be reaching out to him to make sure that the needy person will not lack those necessities that all people require, such as food, clothing and a roof over his head. All these items require forethought to guarantee that the poor person will receive the maximum benefit with the least amount of trouble. About this the Sages commented: “The reward for tzedakah is paid only in accord with the amount of chessed-kindness it contains” (Sukkah 49b).
Now, if the benefactor can be even more thoughtful about it, and give the needy person the tzedakah in a manner that he does not know where it came from — fortunate is the benefactor’s lot! In any event, even if the tzedakah cannot be given anonymously, one should be exceedingly careful to give the tzedakah in private, to spare the recipient embarrassment.