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Within in a few months my dream will come true. I will have published my first book. This book is the product of three plus years of effort, including settling on a topic (becoming the new boss, a book for new leaders to experience sustained success), identifying a target audience (new leaders, primarily on the front-end of their leadership journey), doing lots and lots of writing, testing my content online through regular leadership posts, finding an editor and publisher, and working through the complex publishing process (even the cover design can be a big, time-consuming and emotionally charged deal).  

Without question, this is an exhilarating feeling. Not only am I proud of what I have achieved, but I am super excited to know that very soon I will be able to share my ideas and experiences with so many others.

I often reflect on how I got here and how difficult it may have been had I tried to achieve this goal as a full time head of school (my previous position). Leaving aside the fact that my experiences in that position provided much of the fodder for my text (something that I likely could not have shared freely while under contract), I think that the rigors of full time employment would have made such an undertaking daunting, to say the least. Without having real control over my time and with the many demands of school leadership, how could I have possibly seen this process through? The likely answer is that I wouldn’t have. And I suspect that many leaders with great content, ideas, anecdotes, experiences and achievements feel similarly.

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Today’s weather up in the northeast (US) was far from ideal, at least if you were hoping to go in to work. After three rounds of shoveling, there’s still no end in sight to the white invasion that has made travel and general life activity a challenge. But the good news is that the time outside has given me opportunity to reflect and ponder how snow-related lessons can have a positive impact on us today and well into the (hopefully warmer) future. These are some of the ideas that came to mind:

1. Be prepared – Nothing spells doom for a day like today than the absence of proper preparation. Knowing that a storm was looming, I made my way out to the shed yesterday to get the snow blower, shovels, etc. We also stocked up on food staples and other necessities. In life we also need to be prepared for what’s to come. Sometimes these challenges are in the “forecast”. Sometimes they arrive will more suddenness. Either way, the better prepared we are, the likelier that we can take life’s challenges in stride.
2. Plan for the worst but expect the best – One never really knows what weather you’re going to get, which is why the weathermen like to cover themselves with a wide range (say, 12”-24”, for example). While we need to prepare for the worst, we should always expect the best, and plan to maximize our days rather than succumbing to the “what can I possibly get done on such a day?” mindset.

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One of the most widely watched TED talks on education was delivered by Rita Pierson. In a moving talk entitled, “Every Kid Needs a Champion”, Pierson, a second-generation educator, emphasized the importance of building relationships with students. She details her experience working with some of the hardest challenges in the system: kids who haven’t tasted academic success and often lack strong adult relationships that can provide guidance and inspiration and also strengthen resolve. Her successes, she says, were to a large degree the result of believing in her charges and giving them a vision of a better tomorrow.

Ironically, having a champion can have its downsides for kids as well. In a recent parenting post by Kathy Caprino, the author cites leadership expert Dr. Tim Elmore, who shared a list of ways in which parents today are failing their children by coddling and crippling them. Such behavior, says Elmore, prevents children from becoming the strong, independent leaders and balanced adults that they are destined to be. According to Elmore, current parental failures include:

1. Not letting our children experience risk – We live in a dangerous world that is full of risk. But instead of allowing our kids to get out there, we seek to provide a strong layer of protection. For kids to succeed, they need to fall a few times to learn it’s normal. Parents who remove risk from their children’s lives will promote low self-esteem and greater insularity in our children.
2. Rescuing kids too quickly – Today’s adults have a propensity to swoop in and take care of problems for them. When we rescue too quickly and over-indulge our children with “assistance,” we remove the need for them to navigate hardships and solve problems on their own.

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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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