Leadership Skills: You Can Learn From the Past, But You Still Have to Lead the Future

There is an interesting moment towards the end of Moshe's life. After forty years of leading the Jewish people, Moshe knows that he will not be the one to take them into the Land of Israel. That responsibility will fall to his student and successor, Yehoshua. As he prepares Yehoshua for what lies ahead, Moshe tells him, “Be strong and courageous.” It is a powerful instruction, but there is something interesting about it. Yehoshua was probably as prepared for leadership as anyone could possibly be. He had spent years beside Moshe, observing one of the greatest leaders in Jewish history. So why did he still need to be told to have courage?

Moshe and Yehoshua came to leadership and leadership skills from very different places. Moshe had almost no precedent to follow. There had never been a leader of the Jewish people in the circumstances he was about to face. From the moment he first approached Pharaoh, he was learning this kind of leadership on the job. In fact, his first attempt to help the Jewish people seemed to make their lives worse. Pharaoh responded by increasing their workload while demanding the same output. Moshe then had to lead a nation out of slavery, through the splitting of the sea and into the wilderness. Along the way came complaints about food and water, the Golden Calf, the tragedy of the spies, Korach's rebellion and countless other challenges. There was no handbook explaining how to lead millions of former slaves through the desert while transforming them into a nation. Moshe had to confront each new challenge as it arrived.

Yehoshua had something Moshe never had. He had Moshe. He had spent years watching his teacher lead. He had seen Moshe under pressure. He had watched how he responded to criticism, disappointment and rebellion. He had seen moments of extraordinary success and moments of terrible failure. Yehoshua therefore entered leadership carrying decades of accumulated experience, even though much of that experience had been gained by observing someone else. Yet Moshe still tells him, “Be strong and courageous.” Perhaps that is because preparation can teach us how others dealt with yesterday's challenges, but it can never completely prepare us for tomorrow's.

Yehoshua was not being asked to become another Moshe. The Jewish people themselves had changed. Moshe had taken responsibility for a nation emerging from generations of slavery and back-breaking labour. They had spent their lives being told what to do by Egyptian taskmasters and suddenly had to learn what it meant to live as free people. Yehoshua, however, would lead a new generation. They had grown up in freedom. His challenge was no longer to take the people out of Egypt, but to take them into Israel. He would have to inspire them to cross the Jordan, confront powerful enemies, conquer the land, divide it amongst the tribes and begin building a functioning society. The lessons Yehoshua had learned from Moshe were invaluable, but the circumstances he faced would never be identical to those of his teacher.

This is true in our own lives as well. We should learn from those who came before us. We should seek mentors, study successful people, listen to our parents and teachers, read books and learn from the experiences of others. One of the great advantages we have is that we do not need to make every mistake ourselves. We can learn from what others got right and from what they got wrong. But eventually, preparation reaches its limit. There comes a point when nobody can tell us exactly what to do because nobody has ever lived precisely the life we are living.

A parent can learn a great deal from the way they were raised, but their children are different people growing up in a different generation. A business leader can learn from someone who built a successful company twenty years ago, but the market, technology and expectations of customers may have completely changed. A community leader can study how previous generations responded to their challenges, but today's community may face problems those leaders never imagined. Even within our own lives, something that worked brilliantly ten years ago may no longer be the right answer today. Wisdom means learning from experience without becoming trapped by it.

Perhaps this is why Moshe does not tell Yehoshua, “Don't worry, you are completely prepared.” Instead, he tells him to be strong and courageous. Experience does not eliminate uncertainty. Preparation does not guarantee success. Courage is necessary precisely because we cannot know exactly what will happen next. We sometimes imagine that confident people act because they are certain of the outcome. More often, they have simply accepted that certainty is unavailable. They gather the information they can, seek advice, prepare carefully, make the best decision available to them and then move forward.

There are times in life when preparation itself can become a hiding place. We tell ourselves we need to do another course, speak to another person, conduct more research or wait until circumstances become clearer. Sometimes that is wise. But sometimes we already know enough to take the next step and what we are really waiting for is the feeling of complete confidence. That feeling may never arrive. Yehoshua had spent decades preparing for leadership and still needed courage when the moment came to lead.

As we approach a new year, there is something particularly meaningful about this message. We should look back and learn from the year that has passed. We should ask what worked, what did not, what we would repeat and what we would change. The past is an extraordinary teacher, but it is not a map of the future. None of us knows exactly what the coming year will bring. We take the lessons with us, but eventually we must turn around and face forward.

Perhaps that is the challenge Moshe was giving Yehoshua, and the challenge for each of us as well. Learn everything you can from those who came before you. Learn from your own successes and mistakes. Prepare yourself carefully. But don't wait until you know exactly what lies ahead before you begin moving. Leadership Skills include learning from the past to lead the future, but at some point, preparation has done its job and courage has to take over.

So as you consider the next step in your own life, ask yourself: Have I genuinely not prepared enough, or have I prepared enough and am simply waiting to feel completely ready?

Sometimes the next stage of our lives begins when we accept that we may never feel completely ready, and move forward anyway.