
Should You Be Friends With Your Boss? + 3 More Career Dilemmas
From Per My Last Email by Morning Brew
May 11, 2026 · 33 min
About this episode
Kaila and Kyle answer listener-submitted questions about career dilemmas and advice.
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 Want to get all of Kaila & Kyle’s career resources? Subscribe to Per My Last Email: https://www.permylastemailshow.com/ Watch Per My Last Email on YouTube: @PerMYLastEmailShow Follow Per My Last Email Instagram: @permylastemailshow TikTok: @permylastemailshow Twitter: @permylast_email Have a question for us? Send us an email or voice note to permylastemail@morningbrew.com Learn more about…
People in this episode
Hosts: Kaila, Kyle
Topics covered
- career advice
- work dilemmas
- remote work
- merger preparation
- friendship with boss
Keywords
- career advice
- work dilemmas
- remote work
- raise
- merger
- friendship with boss
Sponsors
Granola
Mentioned in this episode
Organizations: Morning Brew
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