As a reminder for this series, we will not be considering his background or upbringing or training but will solely focus on his time as the king of Israel. This decision helps isolate his defining moments as a leader regardless of the rich or poor leadership development that he went through.
Saul starts off well in 1 Samuel 10-11 where he is named king and then gets to work. As he is announced as the chosen one to be king, people bring him gifts; however, a group of people immediately disrespect him without a gift but with grumbling. Saul ignores the disrespect to himself but cannot ignore the disrespect of an Ammonite to a Hebrew town. After the victory, those fighting by his side want to go kill those who refused to bring him a gift but Saul does not want to take action. He wanted to build unity instead of creating further division - something an initiator will do.
Saul then has to deal with his first challenge as the Philistines, the ever-present enemy of Israel, rise up to cause problems. Saul organizes an army, including is son Jonathan, and awaits the prophet Samuel. While waiting, many of the soldiers are overcome with fear and decide to leave. Saul, in seeing people leaving, decides to take action to keep everyone together - he offers the sacrifices (something he should never do as it violates his purpose). No sooner had he finished the act, Samuel appears and asks what he has done and declares he acted foolishly (1 Samuel 13:11, 13). Unfortunately, these disobedient actions by Saul would not be an isolated incident (see 1 Samuel 15).
The war with the Philistines created accolades for the one chosen to follow Saul as David killed Goliath. This amazing victory gained favor with others and causes significant jealousy on the part of Saul. This envy arose in 1 Samuel 18:7 as we see both Saul and David returning from a successful campaign against the Hebrew enemies. The common song of celebration said: "Saul has slain his thousands and David his ten thousands." Saul, as the initiator and 1st king, had to be the best and, from this point forward, he viewed David as a threat. He acted in foolish ways to remove David as a threat: (1) trying to kill him with a spear several times, (2) attempting to have the Philistines kill him through a stealthy wager that failed, (3) chasing him across the kingdom to trap him, (4) killing several priests for a supposed disrespect to him, and (5) cursing his own son Jonathan and threw a spear at him for supporting David.
Finally, we see Saul's failure to admit his mistakes and then act accordingly to change. When he disobeyed God in 1 Samuel 15, he lied to Samuel; and when caught in the lie, blamed the people for the disobedience. He was the leader and could have restrained them but, as the initiator, he did not want to make the tough call. Later, in 1 Samuel 24, David could have killed Saul but did not. After finding out how David acted righteously, Saul admitted his mistakes in pursuing David and knew that he would be kind over Israel; however, he would later continue to chase David in jealousy to kill him.
Ultimately, Saul's rash actions and disobedience removed any opportunity for a royal dynasty for his sons. As the initiator, he established an awful example of what a king/leader could and should be. Yes, he started the line of Hebraic kings but he did not start them well.
Leaders that are initiators (e.g. starting a new organization) would do well to learn from the example of Saul. Specifically, we can learn several lessons from this failed leader of Israel.