A Matter of Place by Michael Rosenthal

(2006/5766) In Parashat Devarim, Moshe recalls in his speech three
seemingly random stories in succession: the introduction of
the judging system, the deploying of spies into Eretz Yisrael,
and Bnei Yisrael attacking the Emorim in Eretz Yisrael.  Why
does he mention these stories at all, and why specifically next
to each other?
Perhaps we can find the answer by examining the results
of each story.  In retelling the story of implementing the
judging system, Moshe first gives Bnei Yisrael a blessing that
they should increase in size, then continues that he instructed
them to find wise and distinguished men to judge them.  Bnei
Yisrael agreed to this suggestion, and we hear nothing
negative about the experience.
The stories about the spies and attacking the Emorim, on
the other hand, are presented entirely differently.  Moshe
gives no blessings, he does not tell of introducing the ideas to
Bnei Yisrael before implementing them, and in the end, he
describes how Bnei Yisrael ignored Hashem’s instructions
and caused major problems for themselves.  In the story of
the spies, they were punished with being banned from
entering Eretz Yisrael because of the slander about the land,
and in the story of the Emorim they were defeated because
they attacked despite Hashem’s warning not to.
It seems that Moshe recounts these stories together in his
speech to stress that the best results occur when the people
use their best judgment to evaluate the ideas of their leaders,
rather than overwhelming their leaders with suggestions or
overruling them.  It is not for the people to pressure their
leaders into agreeing with their ideas or to simply override
what a leader says, as they did in the stories of the spies and
the Emorim.  Rather, they should either approve or
disapprove the suggestions of their better-educated leaders,
as they did with the suggestion of the system of judges.  The
leaders, meanwhile, must do their part, contributing helpful
and well-thought- out suggestions.  If both parties act within
these bounds, their potential for success is boundless.

The Middle Road by Yitzchak Richmond

In Hashem’s Hands by Nachi Friedman