When Moshe anticipated the need to transfer leadership before his imminent death, he selected Yehoshua to succeed him.
Out of all the possible candidates, Yehoshua was apparently the most suitable candidate, as he had been Moshe’s faithful steward for many years, and had been entrusted to scout the land of Israel, and resisted the conspiracy that led to the lost generation that would wander the desert for 40 years.
Yet we find that someone else actually led the resistance to the conspiracy and tried (and failed) to dissuade the people from overreacting: Moshe’s brother in law, Caleb.
So why was Yehoshua chosen to lead?
Perhaps it is because Yehoshua embodied a quality of humility that Caleb did not.
The scouts were senior members of their tribes, and the Zohar says that the conspiracy was motivated by perceiving the Land of Israel as a threat to the status quo, and they would lose all their influence.
The Kozhnitzer Maggid explains that while Yehoshua would have no interest in retaining power per se, he could have joined the conspiracy to avoid his succession in the wake Moshe’s death.
To protect the integrity of the scouting mission, Moshe blessed his steward that God would safeguard him; and changed his name from Hoshea to Yehoshua before he set out.
R’ Menachem Mendel of Rimanov cautions a leader who is too humble to stand up for what is right for the sake of avoiding conflict.
R’ Yissocher Frand notes the remarkable lesson that while negative traits like anger are damaging on their face; positive traits like humility can be insidious when imbalanced too. Any agenda – however noble – can cloud our judgment.
R’ Shai Held notes that the humility that was almost Yehoshua’s undoing on his first journey to Israel would be the making of him on his second.
While Caleb was fearless in the face of an angry crowd; that is not a feature in military strategy. A moment of pause for deliberation is a good thing for planning, and Yehoshua would be better at that than Caleb.
Some moments require decisive action; others require reflective contemplation. It is not always clear which is called for under the circumstances, but the example set by Yehoshua is exhaustive – in the face of danger he wasn’t aware of, his mentor’s foresight protected him – עשה לך רב.
One of the best pieces of advice in any field is to seek an experienced perspective from someone looking out for us who is impartial to our self-serving biases.