Workday Playdate Snack 24: How to Make Managing Up Feel Natural (Not Cringey)
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)
- Did today’s episode resonate with you? Leave us a review sharing your favorite insight and we’ll send you a free signed copy of I See You! A Leader’s Guide to Energizing Your Team through Radical Empathy.
- Have another question that we can answer? Leave us a Speakpipe audio clip and we’ll answer it in an upcoming episode.
- Don’t want to miss another episode? If you’re a Spotify listener, find our show here and click “Follow.” If you’re an Apple Podcast listener, click here and make sure to hit “+Follow.”
- Want access to a bunch of free resources for your work life? This is your personal jackpot that gives you access to the frameworks that help us thrive both personally and professionally. Whether you’re trying to improve your daily routine, flesh out an idea that you’ve had for quite some time, or want to add more play into your day - these resources have got your back.
- Want 2 emails a week from us? One with a quick tip you can implement right away to enhance your personal and/or professional lives & one of our famous F.A.I.L. Fourward Friday newsletters? Subscribe here.
Connect with Erin Diehl x improve it!