He must stand together with the people. He must give them courage and succor to go on, to triumph over pain and adversity, to withstand challenge, and to succeed under difficult circumstances, While many leaders possess both of these qualities, some have a difficult time discerning when to exercise strength and aggressiveness and when to be flexible and supportive. Chazal tell us that when Avraham Avinu died, all of the world leaders stood in a row as mourners to lament his passing. Woe is the ship that has lost its captain. Land and water are analogies for two divergent situations.
Land symbolizes stability, normalcy and peace.
Some leaders are great in times of peace, when everything seems to go smoothly, when all factions of the community seem to get along, when everyone sublimates himself to Torah directive as expounded by the gedolei ha'dor. If things were to change, if a crisis were to appear, this leader would probably disappear. The alternative type of leader seems to thrive on crisis. He is able to stand tall. He leads his flock during crucial periods, when the correct decision means survival and ambiguity can instantaneously transform into serious dilemma.