Awkward Conversations | Foundation 5 – Lesson 8

Go back to Job Search Prep Syllabus.

There are a number of awkward conversations you are going to have during your job search. Some will include re-introducing yourself to someone who forgot who you are; some will be about money; some will be about the type of work you’d be doing. Sometimes, you’ll find yourself on the defensive, and sometimes, you’ll be applying the pressure.

Regardless of the specifics of the conversation, there is an approach you can use to make these conversations go easier:

Picture the next conversation after the one you’re about to have.

For example, if you need someone to forward your resume, the next conversation after this one should be when the person calls you back proactively, and tells you—excitedly—”Hey, I got in touch with Jim, he’s got your resume, and he said to call him by Wednesday if he hasn’t already reached out to you by then.” Now, working backwards, we know that the conversation you’re about to have needs to end at a place that makes this “next” conversation possible.

Continuing to move backwards, we can then figure out the tone and message for this conversation… before long, while the conversation doesn’t become easy, it does become less awkward.


Once again, put this lesson to use as you continue the exercise from yesterday.

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