May 11, 2026

Should You Be Friends With Your Boss? + 3 More Career Dilemmas

Should You Be Friends With Your Boss? + 3 More Career Dilemmas

In this episode, Kaila and Kyle answer listener-submitted questions around career advice and work dilemmas. From just how friendly you should get with your boss to how to ask for remote work accommodations, this episode addresses a wide range of relatable scenarios.

00:00 Intro

02:56 Question 1 - Can you befriend your boss?

10:37 Question 2 - Can I ask for a raise after a round of layoffs?

15:50 Question 3 - How can I ask for remote work accommodations?

21:57 Question 4 - How should you prepare for a merger/acquisition at your company?

This episode was sponsored by Granola. Head to granola.ai/brew to try Granola for free. That’s granola.ai/brew to try it today for FREE.

Find Granola-generated notes on this episode here: https://notes.granola.ai/t/4c7f65b0-fdee-40ca-9e1c-e9aa332279f7-009c2hma

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Each week on Per My Last Email, Morning Brew’s resident career experts Kaila and Kyle – whose careers have collectively spanned the corporate, government, nonprofit and startup sectors – debate the trickiest challenges in work life, and share tactics on how to overcome them. Share the show with a friend, and leave us a review on your favorite podcast app!


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