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

Written By Erin Diehl
 
 
 

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In today’s snack-sized dose of Workday Playdate, Erin’s flipping the “fear your boss” script and serving up an improv-inspired reframe that’ll help you manage up with confidence, not chaos. Spoiler: It starts with a Slack message and ends with you owning your power. 

The Problem: 

You get a vague “Let’s chat” from your boss and spiral. Are you getting fired? Forgotten something? Turns out, you’re not alone. Gallup says 70% of team engagement depends on your manager... but only 30% of early-career pros feel confident talking to theirs. Most of us are winging it. Badly. 

The Improv Hack to Try: Play the Status Shift 

In improv, every scene has a status dynamic, and you can shift it. So instead of acting like a nervous squirrel asking for approval, show up like a grounded scene partner. Sit tall. Pause before you speak. Lead with thoughtful questions like: 

“Does this align with your priorities?” 

You’re not pretending to be the boss. You’re showing you’re a partner in progress. That small shift builds trust, signals self-assurance, and makes managing up feel human. 

Wednesday Tease: Episode 301 — “Real Talk: How to Stop Guessing What Your Boss Wants” 

Get ready for a career-changing convo with Melody Wilding: human behavior expert, executive coach, and author of Managing Up. She’s bringing real talk, hilarious insights, and zero fluff to help you navigate tough convos and lead from where you are. 

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 Erin Diehl x improve it! 

 
Erin Diehl
Next

Episode 300: You Found a Mentor - Now Here’s How to Keep the Relationship Thriving