In this episode, Kaila and Kyle discuss how to have those difficult conversations at work with career advice expert Erin McGoff of @advicewitherin. From addressing your lazy coworker to handling your micromanaging boss, Kaila, Kyle, and Erin offer specific tactics and approaches for conducting these challenging conversations.

00:00 Intro

00:55 How Advice With Erin got started

03:49 Stats on how much people avoid having difficult conversations

04:34 How Erin recommends approaching difficult conversations broadly

08:25 How to prep for having a difficult conversation

14:34 Difficult conversation scenario 1 - Telling your boss that you’re quitting

19:25 Difficult conversation scenario 2 - How to address your anxious coworker

24:41 Difficult conversation scenario 3 - How to deal with a micromanaging boss

29:28 Difficult conversation scenario 4 - How to address a team member who isn’t pulling their weight

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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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