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  • Writer's pictureMargaret Cissel

Your Winter Break Job Search To Do List

We know that the weeks between Thanksgiving and Winter Break are busy times for teachers, especially this year as schools navigate between in-person and remote learning.  Hopefully, you find yourself with some well-deserved downtime during Winter Break and you can steal a few moments to think about your independent school job search.

This has been a tough year to plan ahead and while plans often change at the last minute, it is highly likely that the hiring season will be conducted virtually again this year.  Schools will continue to have openings for the fall, so it never hurts to explore new jobs in schools even if you’re just curious about making a possible move.  You never know when your dream job may appear!  Below are some actions you can take over Winter Break so you’re ready to hit the ground running and find your next administrator or teaching job in an independent school in 2021.

Of course, you can always reach out to your Placement Manager at Educator’s Ally at any point to discuss the below in more depth. We love hearing your hopes and ideas for your future job search.

  1. Define the right fit for you

  2. Think about what types of opportunities and kinds of schools appeal to you.

  3. Is this the year you start to explore leadership positions?

  4. Have you always wondered what it would be like to teach in a school with a different philosophy than your current school?

  5. Does a cross-country move sound fun?

  6. EA Tip: Casting a wide net in terms of location, school type, and position will increase the number of potential opportunities your Placement Manager will be able to share with you (which means increased odds of an offer!).

  7. EA Tip: Keep an open mind, there’s no harm in hearing about something new.

  8. Review and edit your resume

  9. Have your responsibilities changed since your last search?

  10. What professional development sessions have you attended?

  11. Were you able to attend this year’s virtual People of Color Conference or other virtual conferences?

  12. Have you served on any committees?

  13. Did you start or complete a graduate program?

  14. Are you an Associate Teacher with sole responsibility for a pod of students?

  15. EA Tip: Be sure to include information about your remote teaching.

  16. What technologies did you use?

  17. Did you attend any professional development sessions about remote or hybrid learning?

  18. Are you coordinating remote learning for your whole division or providing in-house professional development for your colleagues on this topic?

  19. EA Tip: Share your updated resume with your Placement Manager so they can offer feedback.

  20. Draft a cover letter

  21. Having a strong cover letter template you can tweak for each search will save you time and stress this hiring season.

  22. Feeling confident in your cover letter template will make it easier for you to apply for more positions.

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

  24. EA Tip: Share your drafted template with your Placement Manager so they can provide additional ideas or edits.

  25. Ask for references

  26. 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.

  27. If your search is confidential, are there any colleagues who you trust to keep your job search quiet?

  28. EA Tip: Ask your references soon so they have time to write a thoughtful letter.

  29. EA Tip: Remember you can share your Placement Manager’s email with your recommender so that they can send their letter confidentially.

  30. EA Tip: 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.

  31. Film a (virtual) demo lesson

  32. If you are teaching in-person, filming a lesson of yours will be useful in your job search this year. Having a demo lesson available will allow potential schools to see an example of your work (of course, this will need to wait until after break when students return).

  33. Another option is to record yourself teaching a virtual lesson. Plan a sample lesson or morning meeting and film yourself teaching as if your students were present.  This can showcase how you creatively use technology to engage your students and how quickly you’ve adapted to online learning.

  34. EA Tip: Read our blog on virtual lesson tips here.

  35. Reflect on 2020

  36. The pandemic has been hard on everyone, and has especially upended how we teach and learn. Think about how the transition to remote or hybrid learning (or switching back and forth between in-person learning) has gone for you and your school.  What have you learned about yourself?  Did you discover new skills?  Has your teaching changed and adapted for the better?  What did you learn in the spring that you changed for this fall?

  37. How does your identity affect your teaching, students, and colleagues? What steps have you made to make your classroom and curriculum a more inclusive and equitable place?  What personal steps have you taken to explore your identity?  What anti-racist and anti-bias work have you done, even if not through official channels at your school?

  38. This hiring season, you will be asked about online learning and your experience in DEI and anti-racist work, so thinking about how you’d answer possible interview questions on the topics will help you prepare.

  39. Connect with EA

  40. If you aren’t already working with EA, apply now! Your Placement Manager is a great resource to review your documents, help with interview prep, answer questions along the way, and (not to mention!) 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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