March 31, 2025

Tackling Difficult Conversations with Erin McGoff

Tackling Difficult Conversations with Erin McGoff

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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