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

Page: https://stenobird.com/podcast/per-my-last-email-6868760/should-you-be-friends-with-your-boss-3-more-career-dilemmas
Text version: https://stenobird.com/podcast/per-my-last-email-6868760/should-you-be-friends-with-your-boss-3-more-career-dilemmas.md
Podcast: [Per My Last Email](https://stenobird.com/podcast/per-my-last-email-6868760)
Published: 2026-05-11T10:00:00+00:00
Episode link: https://www.podtrac.com/pts/redirect.mp3/pdst.fm/e/tracking.swap.fm/track/bHsDpvy53mYwJpnc1UL5/traffic.megaphone.fm/MOBI7783559164.mp3?updated=1778266842
Audio file: https://www.podtrac.com/pts/redirect.mp3/pdst.fm/e/tracking.swap.fm/track/bHsDpvy53mYwJpnc1UL5/traffic.megaphone.fm/MOBI7783559164.mp3?updated=1778266842
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Duration seconds: 1974

## Resource

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 your ad choices. Visit megaphone.fm/adchoices 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! Learn more about your ad choices. Visit megaphone.fm/adchoices

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