I recently posted a job description for an Executive Assistant. As I prepared to write the post, I recalled that I had one that I had written a few years back that with a few updates would likely work. I pulled it up and my visiting brother-in-law, Maccabee Avishur, who is the Senior Director of Prizmah Services, a master educator and an educational consultant, scoffed at what he saw. He asked me why would I post that to which I said “it is a pretty standard job posting.” He responded, “exactly and is that what you are looking for? Standard?.” No, I wasn’t, and he suggested I write a job description in my voice that gives the reader a sense of who I am and what I am looking for. So, I begrudgingly agreed to try a rewrite and quickly started to have a lot of fun with it. In the end, the new job description looked entirely different than the original. In addition, I found myself with almost ten times the amount of applications than when I had posted for the similar position three years ago.  Plus, the applicants tended to be more creative and unique which is what I was looking for. Below is the original job description followed by the reimagined one, which is followed by my favorite cover letter from an applicant.



GENERAL DESCRIPTION: The Administrative Assistant to the Principals is responsible for working directly in an administrative support role and reports directly to both the Principal and General Studies Principal.

QUALIFICATIONS: High school diploma or GED; supplemented by minimum two (2) years previous experience that includes secretarial or clerical work, or any equivalent experience which provides the required knowledge, skills and abilities to perform the essential job functions.


  1. Requires strong service-related people skills and problem solving skills as this position is generally the first contact with those requiring the Principals and has significant responsibility in representing the school.
  2. Requires strong verbal and written communication skills due to interaction with the general public, school personnel, parents and students on a regular basis as well as responsible for editing and writing various school communications.
  3. Requires strong, positive interpersonal relationship skills between students, staff, parents, and community members.
  4. Requires strong organizational skills to balance demands of a multi-tasking position.
  5. Requires strong technology skills in the areas of office software, electronic communication, database systems, word processing, spreadsheets, and office equipment operation; i.e., phones, fax, and copier (knowledge of photoshop a plus).



THE QUESTION: Are you interested in being part of the educational revolution? Then read on my friend.

THE ANSWER: We are looking for someone great to be our new EXECUTIVE  ASSISTANT TO THE HEAD OF SCHOOL. This individual is responsible for working directly in an administrative support role and reports directly to the Head of School. Akiba-Schechter is a vibrant Jewish Day School community of students, staff, parents and the occasional rabbit from the park across the street. We are a family devoted to the teaching and learning of all the children and staff in our building. We are devoted to celebrating and preserving childhood while being a leader in the field of education. We are committed to creating a positive culture for our students and staff, and we are looking for someone to help support our new and exciting Head of School in continuing to do just that.


A College diploma or higher; ideally supplemented by a minimum of two (2) years previous experience that includes administrative or clerical work, or any equivalent experience which provides the required knowledge, skills and abilities to perform the essential job functions. However, we also feel strongly that your degrees and experience do not define you so if you think you are the right person for this position apply. We are just looking for someone with the right energy, creativity and work ethic that loves everything listed below.


  1. the sound of little kids with huge smiles on their faces because they are enjoying school
  2. interacting with people of all ages (the kids, their parents, grandparents and all the teachers who adore them)
  3. solving little problems, big problems and the occasional middle of the road problem
  4. representing an amazing school community
  5. expressing yourself with your strong verbal skills and writing the occasional magnum opus in the form of a memo, email or newsletter
  6. being creative and sharing your ideas because you know your ideas rock
  7. organizing a highly creative Head of School who needs to be told once in while to put the skateboard away and finish that letter
  8. not one, not two, not three, but a multitude of tasks
  9. Apple, but can tolerate Windows
  10. database systems, word processing, spreadsheets….ok you don’t love them, but you know how to use them and use them well. Knowing and loving Adobe Creative Suite would be a plus.
  11. that there is no “I” in team, but have occasionally smirked at the fact that “me” is in it
  12. the idea of working at a school that is leading the way in education and you want to be a part of it

This is a full-time position, and if you are interested, please email with the subject “I AM IN!”



My name is (name taken out) and I am the clerical assistant and nerd that you need for this job. Let’s start with the concrete facts. I’m a former entrepreneur that owned his own comic book store for 5 years. I am proficient on Mac and PC and have a great understanding and knowledge of the entire MS Office Suite. I am organized, creative and focused. As a single dad I love kids. As a graduate with a degree in graphic design I am great at using the adobe line of products. I am a team player and self starter and always willing to go the distance be it showing up early or staying late or giving up a weekend to accomplish our goals and tasks.

Now onto the other intangibles that make me perfect for this job. I am a social butterfly that believes in genuine connections with people. I am witty, funny (at least in my own mind), natural leader and creative problem solver. I often ask, “What would Batman do?”

I do believe I possess the skills needed to get my Head of School to get off the skateboard or at least be able to get him to sign or draft the letter after a few kickflips and ollies. I love working with kids and seeing the future sprout up before my eyes. I also commit to jobs and tasks I believe in. Education being something I value greatly I would excel in a school setting helping make a place run well.

So attached is my resume for your review I hope to meet with my new boss soon.


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