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  • Writer's pictureMargaret Cissel

Your Job Search Over Winter Break

We know that the weeks between Thanksgiving and Winter Break feel hectic for everyone, and that goes double for teachers!  Hopefully, you find yourself with some well-deserved downtime during Winter Break, and in-between time with family and friends, you can steal a few moments to think about your job search.  Below are some actions you can take so you’re ready to hit the ground running and find your next administrator or teaching job in an independent school in 2020!

  1. Define the right fit for you

  2. Think about what types of opportunities and kinds of schools that appeal to you.  Is this the year you start to explore leadership positions? Have you always wondered what it would be like to teach in a school with a different philosophy than your current school?  Does a cross-country move sound fun?

  3. Casting a wide net in terms of location, school type, and position will increase the number of potential opportunities to which you can apply (which means increased odds of an offer!).  Keep an open mind, there’s no harm in hearing about something new!

  4. Review and edit your resume

  5. Have your responsibilities changed since your last search?  What professional development classes have you attended? Have you served on any committees?  Did you start or complete a graduate program?

  6. Draft a cover letter

  7. Every job you apply to should receive its own tailored letter speaking to the specific position, but it can be helpful to get a head start on the bulk of your cover letter that isn’t school-specific.

  8. Ask for references

  9. If your search isn’t confidential, ask a few supervisors if they would be willing to serve as a reference and even write a letter on your behalf.  Ask soon so they have time to write a thoughtful letter.

  10. If your search is confidential, are there any colleagues who you trust to keep your job search quiet?  Former colleagues or supervisors who have moved on from your current school or who you worked within a previous position are good people to ask.

  11. Connect with EA

  12. If you aren’t already working with EA, apply now!  Your Placement Manager is a great resource to review your documents, answer questions along the way, and connect you with your next dream job in a school.


Educator’s Ally is a highly personalized placement agency that connects teachers and administrators with independent day and boarding schools nationwide. Since 1975, EA’s dedicated approach to recruiting has been valued by schools and candidates alike.

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