Numbers 10:29

"And Moses said unto Hobab, the son of Reuel the Midianite, Moses' father-in-law, We are journeying unto the place of which Jehovah said, I will give it you: come thou with us, and we will do thee good; for Jehovah hath spoken good concerning Israel. And he said unto him, I will not go; but I will depart to mine own land, and to my kindred. And he said, Leave us not, I pray thee; forasmuch as thou knowest how we are to encamp in the wilderness, and thou shalt be to us instead of eyes. And it shall be, if thou go with us, yea, it shall be, that what good soever Jehovah shall do unto us, the same will we do unto thee."

There is a whole hateful of problems concerning this passage. First of all, there is what some call the moral problem. Why would Moses who had God Himself as the guide of Israel have sought so earnestly to have Hobab also? We shall not seek to improve the answer given by Maclaren:

What did Moses want a man for, when he had the cloud? What do we want common sense for, when we have the Holy Spirit? What do we want experience and counsel for, when Divine guidance has been promised us? The two things work together.[24]

God's promise of guidance and success never relieved any person of the utmost watchfulness and labor toward the same objective. It will be remembered that God had promised Paul that his life and the lives of all on board the ship would be spared, but it was precisely the watchfulness and alertness of Paul that prevented sailors from lowering a boat and abandoning all on board to certain death (Acts 27:30-32).

Then, there are a number of other problems enumerated by Thompson:

(1) Hobab is here called a Midianite, but in Judges 4:11, he is said to be a Kenite. "Hobab was the leader of a group known as the Kenites, a Midianite clan (Judges 1:16; Judges 4:11)."[25] What is wrong with calling a man a "Texan" on one occasion, and an "American" on another?

(2) Moses' father-in-law is called "Reuel" (Exodus 2:18), "Jethro" in Exodus 3:1 and "Hobab" here. Due to missing information, "This problem is insoluble."[26] The word here rendered father-in-law, in Hebrew, actually may mean father-in-law, brother-in-law, or some other close family relationship.[27] There is also the question (unknown) as to whether any one, any two, or even all three of these names may have referred to one individual. Also, it is not clear whether the name Reuel, for example, might not have been a title held by Jethro, or whether Jethro might have been a title held by Reuel. It is a careless scholar indeed who can bring himself to allege a "contradiction" in any area where such a profound lack of information exists.

(3) Did Hobab actually go with Moses? "From Judges 1:16, it appears likely that Hobab acceded to Moses' request."[28]