"One day when she came to Othniel, she urged him to ask her father for a field. When she got off her donkey, Caleb asked her, 'What can I do for you?' She replied, 'Do me a special favor. Since you have given me land in the Negev, give me also springs of water.' So Caleb gave her the upper and lower springs. The descendants of Moses' father-in-law, the Kenite, went up from the City of Palms with the people of Judah to live among the inhabitants of the Desert of Judah in the Negev near Arad." NIV translation
This passage shows us the failure of the leaders of Israel as Caleb gave his daughter land and water in the desert. This is not a bad thing in itself; the bad thing is that we do not see any mention of taking the matter to God to see what His will was in the matter.
"Then the men of Judah went with the Simeonites their fellow Israelites and attacked the Canaanites living in Zephath, and they totally destroyed the city. Therefore it was called Hormah. Judah also took Gaza, Ashkelon and Ekron - each city with its territory." NIV translation
The men of Judah kept their word and went with the Simeonites to battle the Philistines. They were able to take the cities to the west and on the coast. These were important commercial cities as they were on the main route from Egypt to Mesopotamia.
"The Lord was with the men of Judah. They took possession of the hill country, but they were unable to drive the people from the plains, because they had chariots fitted with iron. As Moses had promised, Hebron was given to Caleb, who drove from it the three sons of Anak." NIV translation
Here, we see the failure of Judah to completely drive out the people from the lands that they conquered. This is one of the main limitations of men as leaders in that we are willing to compromise. The land had been given to them and, instead of taking full possession of what God gave them, they compromised and took what they could with their own strength. This compromise had consequences for the people of Israel and the same is true for us, as Christians, in our walk in this world.