Workday Playdate 301: Real Talk: How to Stop Guessing What Your Boss Wants and Start Managing Up with Confidence with Melody Wilding
In this episode of Workday Playdate, Erin gets real about one of the toughest career skills no one really teaches you: managing up with confidence. Because let’s be honest, trying to figure out what your boss actually wants can feel like decoding emoji hieroglyphics at 11 PM.
Enter Melody Wilding: therapist-turned-career-coach, emotions researcher, and author of Managing Up. Named one of Insider’s “most innovative career coaches,” Melody is here to help you stop overthinking every Slack message and start building a relationship with your boss that’s rooted in clarity, confidence, and collaboration.
Whether you’re a new grad navigating your first 1:1, an early-career professional trying to stand out without burning out, or a sensitive striver who struggles to speak up, this episode will help you transform anxiety into action and guesswork into game plans.
Inside This Episode:
- What managing up really means (and why it’s the fastest way to build trust and grow)
- The 3 toughest conversations to have with your boss — and how to start them
- Why “sensitive strivers” are actually management superstars (with the right mindset shift)
- How to protect your boundaries without damaging your reputation
- One simple step you can take today to feel more confident in every manager conversation
Who This Episode Is For:
Early-career rockstars. Career changers. Anyone tired of reading between the lines of vague emails and ready to build real, human, mutually beneficial relationships at work.
Stop guessing what your boss wants. Start showing up like the leader you’re meant to be.
Listen now and share this episode with a friend who’s stuck in the “do they hate me?” spiral. Let’s make managing up feel less like a guessing game and more like a playdate.
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 Melody Wilding
Connect with Erin Diehl x improve it!