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  • Kris Cosca, EdD

I am Applying for a Job... Tell My Boss?

Updated: Aug 21, 2023

Should I Tell My Boss I am Looking for Another Job?

Should I tell my boss I am looking for another job? This is a frequently asked question. It is asked for different reasons by different people. Sometimes they believe they will not get the job and so they don’t want to upset their boss that they are looking. Other times they adore their boss and don’t want to hurt their feelings. But the most common reason people don’t want to tell their boss is fear… fear of retribution or of damaging a relationship

Yes, You Should

I have a short answer to this question. Yes, you should tell your boss you are looking. The positives of telling them you are looking almost always outweigh the negatives. Telling your boss that you are looking allows you to control the narrative, the timing, and the location of your telling them… It lets you tell them the story you want to tell controlling as many variables as you can.


First, and from a totally practical perspective, you should have a letter of recommendation from your boss or should use your boss as a reference. This is really hard to do if they do not know you are looking.

Second, and this is from a more humanistic perspective, consider the alternative to not telling them and how they will feel when they find out… because they will find out! The most likely ways for them to discover this are to hear from someone else on your campus who knows you are applying, through their leadership network, or through an official or unofficial reference check (yes, both happen!). Put yourself in your boss’ shoes. Imagine how you would feel to discover one of your key leaders on campus was looking for a job without trusting you enough to let you know.

Now hold these two scenarios up to each other. In the first, you control the narrative about your exploring another great opportunity, and the second where your boss is surprised by your application not understanding why you are applying or, more importantly, why you didn’t trust them with this important information. Which option is more likely to harm the relationship?

But Aren’t There Times When This Could Be Used Against Me?

I also know it is possible, though unlikely, that your looking for another position will be held against you in the future. It is a reasonable fear in certain circumstances, however, my question for you is this… will they find out? If they do find out, will it be better for you to have told them or for them to find out that you were keeping your application from them? There is always a chance you will not get the job and which of the two situations leaves your relationship stronger?

When applying for a job, I believe it is almost always better to tell your boss that you are looking. I hope this short blog helps you to realize the same thing!

Let me know your thoughts, any other topic you would like me to write on, and if there is anything I can do to help!

Your dream job could be just a click away. Click here for your free 10-page PDF with 15 steps to help you get your dream principal or assistant principal dream job or here for a seven-minute video that will help you better paint a picture of yourself being successful in your dream job! And here if you want some principal and assistant principal interview questions

Kris Cosca has dedicated his career to public schools for 30+ years as a teacher and administrator. Most recently, he served as superintendent of a 7,500-student K-12 district in Novato, California. Kris has experienced the joys and the challenges at every level – from the classroom to the school board room. He navigated curriculum changes, enrollment challenges, pandemic restrictions, labor negotiations, and staff burnout. As a leadership and career coach, Kris now shares his expertise with Next Level Leadership Services clients.

​Public service runs in the family. Kris' father was a long-time district superintendent in Southern California, his mom was an occupational therapist in a state hospital for her entire career, and Kris married a high school science teacher with whom he has two adult children who are both studying to teach science. Dedicated to his Napa Valley community, Kris serves on the Connolly Ranch Education Center board of directors and supports local, environmentally-friendly acts of kindness through his Facebook Group, Earth's Everyday Heroes.

​Kris also is an avid outdoorsman who fly fishes, ties flies, backpacks, hikes, completes ultramarathons, and cycles.


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