Rabbi Akiva Eger (1761-1837), in one of his responsa (7), addresses the question of whether a woman can fulfill her obligation of Kiddush by hearing the recitation from a boy who has just become a Bar Misva. A boy becomes obligated in Misvot as an adult once he reaches physical maturity, and with many thirteen-year-old boys, it is uncertain whether this has happened. Rabbi Akiva Eger therefore rules that a woman should not rely on a Bar Misva boy’s recitation of Kiddush, since it is uncertain whether he is obligated in Misvot such that he can recite Kiddush for adults. Instead, Rabbi Akiva Eger writes, the woman should recite the words of Kiddush along with the boy and fulfill her obligation this way. Hacham Ovadia disagrees, and rules that one may assume that a thirteen-year-old boy has reached the point of physical maturity required for Misva obligation, and therefore one may fulfill his or her Kiddush obligation by hearing it recited by a thirteen-year-old.
In this responsum, Rabbi Akiva also touches upon a different question, namely, whether one can fulfill the obligation of Kiddush without holding the Kiddush cup. In the case under discussion, the boy recites Kiddush while holding the cup, and the woman must recite the words because she cannot (according to Rabbi Akiva Eger’s opinion) fulfill her requirement through the boy’s recitation. Rabbi Akiva Eger raises and discusses the question of whether the woman can fulfill her obligation in this manner, as she does not hold the Kiddush cup in her hand as she recites the words. The Mishna Berura (Rav Yisrael Meir Kagan of Radin, 1839-1933) rules that in this case the woman must have her own Kiddush cup which she holds as she recites Kiddush, as otherwise she cannot fulfill her obligation.
The Ben Ish Hai (Rav Yosef Haim of Baghdad, 1833-1909), in his work Rab Pe’alim, addresses the more common case of one who recites the words of Kiddush unclearly, inaccurately or inaudibly. Those listening to the recitation must hear every word, and every word must be pronounced correctly. Therefore, if the one reciting Kiddush mumbles, mispronounces words, or does not recite them loudly enough, the others at the table do not fulfill their obligation. In such a case, one must recite his own Kiddush, as he cannot rely on a recitation that is done improperly or inaudibly. The Ben Ish Hai writes – based on the rulings of earlier authorities, including Rav Zalman and the Hida – that in this case one can fulfill his obligation even though he does not hold the Kiddush cup. As long as he sees the Kiddush cup held by the person reciting Kiddush, this suffices under the circumstances. Although it is certainly preferable for one to hold the Kiddush cup as he recites Kiddush, under such circumstances, where one cannot rely on the person reciting Kiddush and needs to recite the words along with him, he can fulfill his obligation even though he does not hold the Kiddush cup in his hand. The Ben Ish Hai applied this ruling to Habdala, as well. Based on a ruling of the Hida, the Ben Ish Hai writes that if one, for whatever reason, does not want to fulfill his obligation by listening to the Hazan’s recitation of Hadbala, he may recite the words along with the Hazan, even though he does not hold the cup. As mentioned, however, it is preferable for one who recites Kiddush or Habdala to hold the cup during the recitation.
Summary: If a person reciting Kiddush for others does not pronounce the words properly, or does not recite them loudly enough, the people at the table should recite the words along with him, and they can fulfill their obligation in this fashion even though they do not hold the Kiddush cup. Preferably, however, one who recites Kiddush should hold the cup during the recitation.