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.