Episode 301: Real Talk: How to Stop Guessing What Your Boss Wants and Start Managing Up with Confidence with Melody Wilding

Written By Erin Diehl
 
 
 

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In this episode of Workday Playdate, Erin takes on the murky waters of managing up and turns your inbox dread into actionable career confidence. Because if you’ve ever reread a Slack message five times wondering if your boss is mad at you…you’re not alone. 

Joining us is Melody Wilding—therapist-turned-career coach, author of Managing Up, and the workplace whisperer you never knew you needed. With deep insights on emotions, communication, and high-achiever burnout, Melody helps you build better relationships up the chain without losing your sense of self. 

Managing up is a skill, not a personality trait. 

Melody breaks down why ambitious, empathetic employees—especially “sensitive strivers”—often second-guess themselves at work. She offers practical tips to communicate confidently, ask for what you need, and stop letting fear drive your interactions with your manager. 

Boundaries build trust. 

We talk about emotional labor, saying “no” without guilt, and why managing up is actually about managing yourself first. You’ll learn how to advocate for your needs without over-explaining or over-apologizing. 

Your manager isn’t a mind reader. 

This episode gives you permission to speak up, ask smart questions, and steer your career forward with intention. And don’t worry—we give you a super doable first step to start the conversation today. 

Feeling stretched thin but still trying to “stay positive”? Grab our free Positivity Without Pretending Toolkit. It’s a quick, honest reset for people leaders who want to show up without faking it. In five minutes or less, you’ll reframe, refuel, and lead with heart (even when you're running on fumes). Download it now and take the pressure off.

No, You Hang Up First (Let’s Keep Connecting) 

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Connect with Melody Wilding 

Connect with Erin Diehl x improve it! 

 
Erin Diehl
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Snack 24: How to Make Managing Up Feel Natural (Not Cringey)