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The Challenge of Leadership

  • The Challenge of Leadership

    D'varim, Deuteronomy 1:1−3:22
D'var Torah By: 

Focal Point

Thereupon I said to you, “I cannot bear the burden of you by myself. The Eternal your God has multiplied you until you are today as numerous as the stars in the sky.” (Deuteronomy 1:9–10)

  • “How can I bear unaided the trouble of you, and the burden, and the bickering! Pick from each of your tribes men who are wise, discerning, and experienced and I will appoint them as your heads.” (Deuteronomy 1:12–13)

D'Var Torah

In Leadership on the Line, Ronald Heifetz and Marty Linsky state: “To lead is to live dangerously because when leadership counts, when you lead people through difficult change, you challenge what people hold dear—their daily habits, tools, loyalties, and ways of thinking—with nothing more to offer perhaps than a possibility” (Leadership on the Line: Staying Alive through the Dangers of Leading [Boston: Harvard Business School Press, 2002], p. 2).

No leader articulates the frustrations of this dangerous role better than does Moses at the beginning of this week’s parashah, D’varim. As the Israelites near the end of their forty years of wandering in the wilderness, Moses looks back at their history. Here he reflects on the events first encountered in Parashat Yitro, where Moses held the burden of making all judicial decisions and rulings for the Israelites. In Yitro, it is Moses’s father-in-law who sees that the weight of the task is too much for Moses to handle alone. Here, in Parashat D’varim, Moses expresses a level of dissatisfaction with his role that we did not hear in the Exodus account.

And why shouldn’t Moses be frustrated? It’s difficult to be a leader. It’s challenging to hold the vision of a new future as your followers confront your decisions, question your rulings, and loudly express their dissatisfaction with the way things are going. It’s tricky to balance the intricate dance of compromise and consensus while trying to move forward. Moses has spent forty years offering the vision, the possibility, of the Promised Land. For the Israelites, it’s been forty years of sand and quail and manna set against the backdrop of a past that looks more alluring in retrospect than it did in reality.

It’s difficult to be a leader. In these verses, however, Moses does more than share his disappointment at the reality of a leader’s role. His solution to governing the Israelites offers us a vision of a different type of leadership. Moses asks the tribes to select wise, discerning, experienced members whom he can appoint to positions of leadership. By doing this, Moses creates a corps of leaders to share the burden of guiding and leading the Israelites.

Admittedly, this “shared leadership” model still includes a central guide who carries the overall responsibility of leadership. Nevertheless, the model represents change for the Israelites and can serve as an example for those of us who are leaders. Moses cannot continue to lead unaided and alone. He needs others to work with him.

A few years ago, the co-presidents of the Women’s Rabbinic Network created a certificate to honor those who had led the organization in the past. They chose a quote from the Talmud: “There can only be one leader for a generation, not two” (Babylonian Talmud, Sanhedrin 8a). To it they appended their own words: “Two leaders, not one, for us.” Shared leadership is no less a challenge than sole leadership. It can be difficult to get an answer to a problem when the answer requires two people to agree. When more than two people share leadership, achieving consensus may paralyze an organization. Any form of collective leadership can slow down decision making. Yet there are benefits to sharing leadership. The loneliness and frustration of the burden we hear reflected in Moses’s words might have been lessened if he had had a partner with whom to vent.

I have learned that I lead best in partnership with others. I find that bouncing ideas off another person or group of people often shows the way to a more creative vision than I would have had working alone. There’s also a level of accountability and responsibility when I know that someone else is counting on me to uphold my portion of an assignment. For me, the benefits of sharing leadership outweigh any disadvantages that come with having to share decision making and power.

As a teacher, I want my students to learn both to lead and to work in collaboration with others. It’s a challenge to balance these goals. Strong leaders run the risk of feeling the frustration of Moses. Often when student leaders can get everything done alone or cannot share tasks with others, the other students abdicate their responsibility to become involved and leave everything to the leaders. But if those in charge don’t provide some leadership and guidance, nothing will be done. The skills my students are developing will serve them throughout their lives. Today they show their leadership on sports teams, in prayer, and in the classroom; tomorrow they’ll be the heads  of our Jewish community.

It’s difficult to be a leader. Whether you’re involved in student government or synagogue politics, or you’re a Moses bringing your people from the comfortable past to the uncertain future, leadership comes with trouble, burdens, and bickering. But when you have people with whom you can share the dangers of leadership, you can lessen the burdens and bravely move forward to the challenges that face us all.

By the way . . .

  • God said to them: “My children are obstinate, bad-tempered, and troublesome. In assuming leadership over them, you must expect that they will curse you and even stone you.” (Sh’mot Rabbah 7:3 on Va-eira)
  • Finally, cooperation does not imply harmony. The relevant question is not whether conflict will occur when people are playing with ideas or struggling to make decisions together: it will and it should. The question, rather, is whether conflict will occur in the context of competition or cooperation. (Alfie Kohn, What to Look for in a Classroom … and Other Essays [San Francisco: Jossey-Bass, 1998], p. 50)
  • At the heart of all leadership—at any age—is character: the courage to cling tenaciously to a vision, the grit to exhaust yourself in helping others to share that vision, and the toughness to endure the blame for every difficulty along the way. (F. Washington Jarvis, With Love and Prayers: A Headmaster Speaks to the Next Generation [Boston: David R. Godine, 2000], p. 310)

Your Guide 

  1. If leadership can be so difficult and challenging, why do people want to be leaders?
  2. Can leadership ever be cooperative? Can it be shared, or do groups need a single, strong leader to be successful?
  3. Jarvis states that leaders need vision, tenacity, and toughness (or courage). What other characteristics do good leaders need to have?
Reference Materials: 

D'varim, Deuteronomy 1:1–3:22
The Torah: A Modern Commentary, pp. 1,312–1,333; Revised Edition, pp. 1,161–1,173;
The Torah: A Women's Commentary, pp. 1,037–1,062