Or HaChaim on Deuteronomy 1:14/אור החיים על דברים א׳:י״ד

1 ותענו אותי ותאמרו טוב הדבר, "you responded to me by saying that the matter was good, etc." Our sages in the Sifri claim that Moses' answer implied that he was critical of the people having approved so readily of his proposal. He felt that they should have objected by saying that surely it was preferable to be instructed by the teacher himself to being instructed merely by the pupil or even by the pupil's pupil. I believe it is possible to explain this verse as a compliment for the Israelites. Actually, the Israelites were sorry not to be instructed forthwith by Moses personally. However, they were willing to put up with this realising that they were doing Moses a personal favour by relieving him of some of the constant pressure he was under. This is the meaning of the words טוב הדבר, "it is a good thing to relieve the pressure from our teacher Moses, even though it is difficult for us to start learning from your pupil instead of from you directly." The words אשר דברת, "which you have spoken," refer to the harsh words Moses had said to the Israelites concerning things which they would have to do. Even though this statement is encapsuled here within the general admonitions, it is possible that Moses was angry also concerning the response of the Israelites.

2On the other hand, Moses was astute enough to formulate his words in such a way that they could be understood as a double-entendre. 1) They could be construed as a criticism as pointed out by Sifri; 2) they could also be interpreted positively as we have tried to explain. The reason Moses did so was because the Israelites could be divided into two categories. There was a category of righteous people; there was also, however, a category of cantankerous people, people who did not miss an opportunity to find fault. The righteous people accepted Moses' words as complimentary; the cantankerous people saw in Moses' words a criticism of the attitude they had revealed.