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Ask the average person what it takes to be a great leader and you will surely hear a bevy of characteristics and qualities, such as visionary, communicator, motivator, and charismatic. Perhaps you will also hear such idealistic qualities as humble, possessor of strong character, and servant of others. All of these relate to how a leader is perceived by others and how he relates to them. While these attributes unquestionably assist leaders in their work with their people, they will still under-deliver if they lack one critical but often overlooked internal quality: self-esteem.

Self-esteem is defined as the degree to which individuals feel comfortable with who they are, believe that they have inherent value as people, have the ability to demonstrate that value, and are confident in their ability to successfully achieve their own measure of success. It isn’t about being boastful, self-centered, or domineering. Rather, it’s about representing ourselves with quiet confidence, as an equal among equals, and leading others from a position of internal strength.

Self-esteem is vital for leaders because it’s what gives them the courage to lead, to pursue success, to and be decisive. A leader with high self-esteem does not feel threatened by others’ ideas, nor will they have a problem with hiring great people and empowering them to accomplish incredible things. Strong self-assurance makes the leader want to see the best in others and help them succeed, knowing that others’ success is ultimately their own. He puts the organization first and is the most committed person in the building. A self-confident leader is more concerned about being part of something great and accomplishing the task than worrying over who will get what position or what recognition.

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One of the greatest challenges that confronted me when I assumed the role of head of school was the contrast in personalities between my predecessor and me. In many ways we were polar opposites, including our general affect, how we interacted with others and in the amount of quiet, private time (with the door closed) that we wanted or needed to function effectively in our jobs.

At the time, I really didn’t appreciate this issue. To me, I was who I was and I assumed that everyone else would simply get used to dealing with a new boss. In hindsight, I feel that I could and should have taken more time to understand my personality and, by extension, leadership profile and how that may impact those around me, especially when they were used to something very different. While personality differences between leaders are to be expected, when they represent a major shift then there can be a difficulty in adjustment for everyone involved. And that difficulty became apparent soon enough in my situation.

One of my favorite leadership training sessions is based on the True Colors Personality Assessment. In this system, people generally identify as being one of four colors: blue, green, gold or orange.

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A story is told about a reporter who was interviewing a successful bank president. He wanted to know the secret of the man’s success. "Two words”, he was told, “right decisions.” “And how do you make right decisions?” asked the reporter. The reply: “One word: experience.” The reporter pressed on. “And how do you get experience?” he asked. To which the banker replied, “Two words: wrong decisions.”

We all recognize the importance of job and life experience, especially for leaders. Experience gives leaders context for important decisions that they must make and insight into how best to lead, motivate and respond to their people. Experienced leaders have been through the wringer before and can use their past learning and decisions to guide them moving forward.

Yet, for many new leaders, experience can be hard to come by. And in today’s fast-changing, competitive environment in which more and more young people are assuming leadership roles, it can be critical for them to find ways to gain experience quickly in order to ensure that they make as few “wrong decisions” as possible, for their own sake as well as for those that they lead.

What can new and aspiring leaders do to gain the benefits of experience when they simply don’t have much on-the-job learning under their belts?

1. Go for training – Identify educational programs that are reputable, respected, and, more importantly offer cutting-edge instruction and hands-on learning that translates well into real-life situations. 
2. Volunteer – See if volunteer opportunities exist for such things as such as managing a project for an overworked leader. (If they presently don’t, go ahead and pitch an idea. Someone is bound to take you up on it if they think that you can help.) Use the opportunity to engage in meaningful work as well as reflective conversations about the leadership task. In this way you can learn much about leadership and how to plan for it in a low stakes environment where there is less pressure to perform and risk of backlash.

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In an earlier post, we presented a number of strategies to help us feel more fulfilled at work. Below are some additional techniques that can deepen our sense of satisfaction from the work that we do each day.

Engage in job crafting

Just because you have a particular job title doesn’t mean that you have no control over how you perform your duties. Take initiative to alter your role by adding, emphasizing, revising, delegating or minimizing tasks and interactions in pursuit of greater meaning. For example, hospital cleaners who lack patient contact stepped up to provide emotional support to patients and their families, and technology associates began volunteering for mentoring, teaching and training roles.

When people craft their jobs, they become happier and more effective. In an experiment at Google, salespeople and administrators were invited to spend 90 minutes doing the Job Crafting Exercise. They mapped out ways to make their tasks and interactions more meaningful and contribute more to others. Six weeks later, their managers and co-workers rated them as happier and more effective. When they developed new skills to support more significant changes, the happiness and performance gains lasted for at least six months.

You may not have the authority to craft your jobs fully, but you can decide on which areas to spend more of your time and invest more of your energy.

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Every holiday has its distinct service and means of connecting us more deeply to God. On Rosh Hashana we focus on coronating our King. On Yom Kippur we engage in deep repentance. Sukkos allows us to remember our true Source of protection and bounty. The service of Chanukah is to shine the light of Torah and adherence on a dark reality that mocks us at our core. Such light can only be generated by a deep engagement that extends well beyond lip service or surface-level devotion.

Where does such depth of commitment come from? How can we genuinely resist all of the pejorative messaging that is constantly broadcast through our soundwaves? Here are some ideas that might help.

1. Turn off the sound – The easiest way to withstand negative messaging is to not hear it. There is no mitzvah to be a full consumer of all the world has to sell us. Keep in mind that certain industries in particular, such as entertainment and the arts, are populated by those with a particularly strong godless, humanistic vantage point which rejects historical truths and values that can’t be quantified by science. When we invite them into our world we make it doubly difficult on ourselves to filter out that which is harmful.

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For most of us, the holiday season is a season of happiness. We get together with friends and family to celebrate our relationships. We also give gifts as a way of demonstrating our love and affection and how much others mean to us.

Many businesses also gift their customers and business associates during this season. They appreciate the special relationship that they’re forged with their clients and consumers and use this time to demonstrate their appreciation. They have built strong relationships and want to make sure that they remain strong in the year ahead.

The importance of developing happy customers is clear. When our customers are deeply satisfied and sing our praises and refer us to others, it helps to build our business on so many levels. We want to have Raving Fans, which, as Ken Blanchard wrote in his book, “Raving Fans,” are fans that “are so devoted to your products and services that they wouldn't dream of taking their business elsewhere and will sing from the rooftops about just how good you are.”

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While the stakes for most business and organizational leaders are far lower than they were for Judah, there are many situations in which marketplace or boardroom victory seems as remote as it did in the Judean caves of the second century BCE. As leaders, we often face circumstances, such as market conditions, lack of funding, or the absence of internal support, that threaten to derail us. We want to persist anyway but recognize the uphill challenges that we will be facing under such circumstances.

What can leaders do inspire themselves and their people to persevere with their dreams when the odds are stacked against them?

• Get a heavy dose of cold water – Leaders who want to succeed when others tell them that success isn’t possible would do well to begin with some honest soul searching. What are the challenges that everyone is talking about? Why are so many predicting your failure? Am I personally biased or do I really have something special here? If, despite their contrarian arguments you feel that your the goal is attainable and you can win, then go for it with everything that you’ve got.

When I left my last position as head of school, I debated back and forth as to whether I should pursue a new principalship or try my luck in the coaching arena. In the end I decided that I really wanted to and parlay my experience and past successes in delivering high-impact trainings. But there were very few people who had done this successfully and so I got on the horn with as many people as I could to figure out why others either hadn’t tried or hadn’t succeeded. After determining that I had a blueprint for a successful foray I committed to my current path and have never looked back

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As I researched this topic I was struck by the extent by which all people, not just back office or less prominent professionals, identify meaning and purpose as central elements of their job satisfaction. We all seek affirmation and want to know that the work that we do makes a difference. Mary Kay Ash once said, “Everyone has an invisible sign hanging from their neck saying, 'Make me feel important.' Never forget this message when working with people.”

Money alone is not what motivates us. In fact, while meaningful pay is certainly a key element in selecting and remaining in a job, compensation is usually not at the top of what motivates us to come to work every day. Purpose, more than any quality, is what we value most.

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