Saul inquired of the Lord, but he did not seek the Lord's guidance

So Saul inquired of the Lord, but the Lord did not answer him – not by dreams nor by Urim nor by the prophets.

~ 1 Samuel 28:6

He [Saul] did not seek the Lord’s guidance, so the Lord killed him and transferred the kingdom to David son of Jesse.

~ 1 Chronicles 10:14 

So Saul “inquired”, but he did not “seek” the Lord’s guidance.  How do you inquire, but not seek?  Here is my best guess. 

The NET rightly uses two different words to translate these two different verbs.  The KJV translates them both as “enquire”.  The verb used in 1 Samuel is the Hebrew word sha’al which means to ask, enquire, borrow, or beg.  The verb used in 1 Chronicles is the Hebrew word darash which means to resort to, seek, seek with care, enquire, or require. The root of darash means to trample or to beat a path.  It carries with it the notion of frequently.  When someone seeks they search after.  This is actually the verb that is used in the 1 Samuel 28:7 about Saul’s trip to Endor.

So Saul instructed his servants, “Find me a woman who is a medium, so that I may go to her and inquire (darash) of her.” His servants replied to him, “There is a woman who is a medium in Endor.”

Saul had to find the witch to seek/inquire of her.  So God killed Saul, because he “darash” the witch, but not Him.  This verb is used earlier by the writer of 1 Samuel to describe Saul. Before Saul was king, he came to seek/inquire of the Lord. 

(Now it used to be in Israel that whenever someone went to inquire (darash) of God he would say, “Come on, let’s go to the seer.” For today’s prophet used to be called a seer.) 1 Samuel 9:9

Now this is not to say that God does not respond to Sha’al, he does.  Before seeking a witch in Endor, Saul had inquired (sha’al) of the Lord, the same way he had many times.  He even threw the holy lots, the Urim.  Back in 1 Samuel 14:24, Saul had made a foolish oath to that anyone who ate before dark would be cursed.  In verse 36, Saul wants to go after the Philistines at night, but the Priest insists that they must approach the Lord first.  So Saul asks (sha’al), in verse 37, but God refused to answer him.  Saul assumes that someone has invited the curse of God upon the army through their sin.    They use the holy lots that eventually fall on Jonathan who had broken the oath.  So God answered Saul by pointing out his son.  Saul would have killed his own son, if the army had not rebelled against their king in protest.  God sometimes answers Sha’al.  In 1 Samuel 28, God expected more from Saul.

The best I can figure the main difference between Sha’al and Darash is persistence.   They both have essentially the same meanings otherwise.  When God refused to answer Saul, Saul went and sought another avenue.  Obviously Saul’s sha’al was intensive: dreams, holy lots and prophets plural.  Still, it was not good enough for God who apparently expected more.  Consider the labor involved in the darash.  Saul went under the cover of night in disguise to a woman that he had been unable to kill.