Workday Playdate

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

• Melody’s LinkedIn
• Melody’s website

• Erin’s website
• Erin’s Instagram
• Erin’s TikTok
• Erin’s LinkedIn
• improve it!’s website
• improve it!’s Instagram

🌟 Learn more about Workday Playdate: https://www.learntoimproveit.com/podcast-page
🎤 Book Erin to speak: https://www.learntoimproveit.com/keynote-speaker
📚 Workshops & Team Experiences: https://www.learntoimproveit.com/experiential-training
💌 Learn more about Erin: https://www.itserindiehl.com/meet-erin
📱 For more information on improve it! visit www.learntoimproveit.com.

If this conversation made you think differently about work, leadership, or building joyful teams, please follow Workday Playdate on Apple Podcasts or Spotify, leave a review, and share this episode with someone who could use more play in their workday.

For more information on improve it! visit www.learntoimproveit.com.

🌟 Learn more about Workday Playdate: https://www.learntoimproveit.com/podcast-page
🎤 Book Erin to speak: https://www.learntoimproveit.com/keynote-speaker
📚 Workshops & Team Experiences: https://www.learntoimproveit.com/experiential-training
💌 Learn more about Erin: https://www.itserindiehl.com/meet-erin
📱 For more information on improve it! visit www.learntoimproveit.com.

If this conversation made you think differently about work, leadership, or building joyful teams, please follow Workday Playdate on Apple Podcasts or Spotify, leave a review, and share this episode with someone who could use more play in their workday.

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.

• Erin’s website
• Erin’s Instagram
• Erin’s TikTok
• Erin’s LinkedIn
• improve it!’s website
• improve it!’s Instagram

🌟 Learn more about Workday Playdate: https://www.learntoimproveit.com/podcast-page
🎤 Book Erin to speak: https://www.learntoimproveit.com/keynote-speaker
📚 Workshops & Team Experiences: https://www.learntoimproveit.com/experiential-training
💌 Learn more about Erin: https://www.itserindiehl.com/meet-erin
📱 For more information on improve it! visit www.learntoimproveit.com.

If this conversation made you think differently about work, leadership, or building joyful teams, please follow Workday Playdate on Apple Podcasts or Spotify, leave a review, and share this episode with someone who could use more play in their workday.

In this episode of Workday Playdate, Erin tackles one of the trickiest parts of professional growth: keeping your mentor relationship alive and thriving. Finding a mentor is like landing the perfect avocado - rare, precious, and you don’t want it to spoil. This episode is packed with improv-inspired strategies to help you nurture that connection, create a two-way relationship, and turn “one coffee chat” into long-term mentorship magic. Whether you’re a new grad navigating your first job, a career changer looking for guidance, or a freshly promoted manager wondering how to level up, this conversation is your roadmap for building relationships that last, without awkwardness or ghosting. Inside This Episode:

• Why mentorship is about clarity, not coffee (and how to define your “why”)
• The calendar hack to keep your mentor connection alive
• How to give back and create a two-way street (yes, even as a mentee!)
• Why celebrating small wins keeps mentors invested in your growth
• The improv-inspired mindset shift — how “yes, and” transforms your mentorship

• 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.

• Erin’s website
• Erin’s Instagram
• Erin’s TikTok
• Erin’s LinkedIn
• improve it!’s website
• improve it!’s Instagram

🌟 Learn more about Workday Playdate: https://www.learntoimproveit.com/podcast-page
🎤 Book Erin to speak: https://www.learntoimproveit.com/keynote-speaker
📚 Workshops & Team Experiences: https://www.learntoimproveit.com/experiential-training
💌 Learn more about Erin: https://www.itserindiehl.com/meet-erin
📱 For more information on improve it! visit www.learntoimproveit.com.

If this conversation made you think differently about work, leadership, or building joyful teams, please follow Workday Playdate on Apple Podcasts or Spotify, leave a review, and share this episode with someone who could use more play in their workday.

In today’s snack-sized dose of Workday Playdate, Erin’s flipping the mentorship script and serving up a strategy that’ll make your mentor want to shout your name from the rooftops. Spoiler: It’s not about being the smartest in the room. It’s about showing up with intention. The Problem: We all say mentorship matters, but too often mentees treat it like a vending machine: insert question, get answer, disappear. That’s not how real relationships (or career growth) happen. The truth? Mentees who bring energy, curiosity, and follow-through are the ones who win every time. The Improv Hack to Try: The Callback Technique Ready to become a mentee your mentor brags about? Start here: Call. Back. Something. The next time you meet, reference a tip or insight your mentor gave you and share what you did with it. Show you were listening and taking action. This tiny move builds massive trust and shows you're not just in it for advice, you’re in it for growth. Why it works: Improv callbacks create connection and continuity, and the same is true in mentorship. When you “call back” something from a past interaction, you’re not just remembering, you’re reinforcing. This keeps mentors invested and mentees unforgettable. Wednesday Tease: Episode 300: “You Found a Mentor—Now Here’s How to Keep the Relationship Thriving.” Your next step? Don’t miss this milestone episode! Erin goes deep on how to nurture the mentorship beyond the first coffee, with more improv-inspired tips to keep the momentum going. Because mentorship is a relationship, not a transaction. 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.

• Erin’s website
• Erin’s Instagram
• Erin’s TikTok
• Erin’s LinkedIn
• improve it!’s website
• improve it!’s Instagram

🌟 Learn more about Workday Playdate: https://www.learntoimproveit.com/podcast-page
🎤 Book Erin to speak: https://www.learntoimproveit.com/keynote-speaker
📚 Workshops & Team Experiences: https://www.learntoimproveit.com/experiential-training
💌 Learn more about Erin: https://www.itserindiehl.com/meet-erin
📱 For more information on improve it! visit www.learntoimproveit.com.

If this conversation made you think differently about work, leadership, or building joyful teams, please follow Workday Playdate on Apple Podcasts or Spotify, leave a review, and share this episode with someone who could use more play in their workday.

In this episode of Workday Playdate, Erin unpacks what employee engagement really looks like in today’s world with Dr. Angela Jackson, founder of Future Forward Strategies. Forget the ping pong tables and perk-loaded culture decks. This is about centering worker voice, listening with intention, and designing workplaces that actually work, for everyone. Whether you’re leading a team, managing up, or trying to make your 9–5 feel more like a “want to,” this conversation delivers bold, strategic insights for building motivated, mission-aligned teams in the modern workplace. Inside This Episode:

• Why real engagement starts with ownership, not office snacks
• The overlooked ROI of actually asking your people what they care about
• How data and feedback loops can drive meaningful culture change
• Post-pandemic playbooks: what’s working now (and what’s not)
• How to bring contractors and non-traditional workers into the mission

• 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.

• Dr. Angela’s company website
• Dr. Angela’s personal website
• Dr. Anglela’s LinkedIn

• Erin’s website
• Erin’s Instagram
• Erin’s TikTok
• Erin’s LinkedIn
• improve it!’s website
• improve it!’s Instagram

🌟 Learn more about Workday Playdate: https://www.learntoimproveit.com/podcast-page
🎤 Book Erin to speak: https://www.learntoimproveit.com/keynote-speaker
📚 Workshops & Team Experiences: https://www.learntoimproveit.com/experiential-training
💌 Learn more about Erin: https://www.itserindiehl.com/meet-erin
📱 For more information on improve it! visit www.learntoimproveit.com.

If this conversation made you think differently about work, leadership, or building joyful teams, please follow Workday Playdate on Apple Podcasts or Spotify, leave a review, and share this episode with someone who could use more play in their workday.

In today’s snack-sized dose of Workday Playdate, Erin’s serving up a spicy truth: no amount of kombucha or karaoke can fix what’s really broken when it comes to employee engagement. The Problem: Only 33% of U.S. employees are engaged at work. And, spoiler alert: swag won’t save us. Connection is the missing link, not cold brew on tap. The Improv Hack to Try: The Scene Partner Swap Flip the script. Instead of waiting for someone else to boost morale, ask: If I were my boss or teammate… how would I help ME feel more engaged? Then act from that mindset for one week. Engagement isn’t entertainment, it’s a feedback loop. Start it. Why it works: Improv teaches us to make our scene partner look good. This mindset shift invites ownership, empathy, and action from any seat in the org chart. Wednesday Tease: Episode 299 — “Want to Nail Employee Engagement? Here’s What Actually Works (No Gimmicks Needed)” featuring Dr. Angela Jackson. Get the real drivers of motivation, leadership, and growth path design, no pizza party required. 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! ·       Erin’s website ·       Erin’s Instagram ·       Erin’s TikTok ·       Erin’s LinkedIn ·       improve it!’s website ·       improve it!’s Instagram

For more information on improve it! visit www.learntoimproveit.com.

🌟 Learn more about Workday Playdate: https://www.learntoimproveit.com/podcast-page
🎤 Book Erin to speak: https://www.learntoimproveit.com/keynote-speaker
📚 Workshops & Team Experiences: https://www.learntoimproveit.com/experiential-training
💌 Learn more about Erin: https://www.itserindiehl.com/meet-erin
📱 For more information on improve it! visit www.learntoimproveit.com.

If this conversation made you think differently about work, leadership, or building joyful teams, please follow Workday Playdate on Apple Podcasts or Spotify, leave a review, and share this episode with someone who could use more play in their workday.

In this episode of Workday Playdate, Erin flips the mentorship script. No more waiting for a career fairy godparent to swoop in with the perfect job offer—this is about building real relationships that actually move the needle. Whether you're fresh out of school, mid-pivot, or just tired of one-sided networking coffee dates, Erin delivers a refreshingly practical (and improv-inspired) five-step framework to help you find the right mentor and become the kind of mentee they want to invest in. From staying close to your current circle to building your own career Avengers-style “board of advisors,” this episode is packed with tools to help you stop wishing for mentorship magic and start building it. Inside This Episode:

• Why being “mentee material” matters more than having a polished pitch
• How to spot potential mentors hiding in plain sight
• Ways to offer value before asking for guidance
• Why mentorship is a long game (and how to play it well)
• How to build your own personal board of advisors

• 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.

• Erin’s website
• Erin’s Instagram
• Erin’s TikTok
• Erin’s LinkedIn
• improve it!’s website
• improve it!’s Instagram

🌟 Learn more about Workday Playdate: https://www.learntoimproveit.com/podcast-page
🎤 Book Erin to speak: https://www.learntoimproveit.com/keynote-speaker
📚 Workshops & Team Experiences: https://www.learntoimproveit.com/experiential-training
💌 Learn more about Erin: https://www.itserindiehl.com/meet-erin
📱 For more information on improve it! visit www.learntoimproveit.com.

If this conversation made you think differently about work, leadership, or building joyful teams, please follow Workday Playdate on Apple Podcasts or Spotify, leave a review, and share this episode with someone who could use more play in their workday.

In today’s snack, Erin’s busting the myth that a mentor is just going to magically appear and fix everything. The Problem: We’ve all heard it—“You need a mentor!” But asking for one feels like proposing after two dates. We freeze, wait, and convince ourselves no one has time for us. The Improv Hack to Try: The Spotlight Flip Instead of waiting for someone to spotlight you, flip the light on THEM. Next time you meet someone you admire, ask: "I love how you [specific thing]. If you were giving a TED Talk to your younger self, what would it be about?" No pressure, just pure curiosity. Why it works: In improv, making others look good builds trust. Spotlighting someone makes them more likely to engage with you, so mentorship might follow naturally. Bonus Tip: Mentorship isn’t always formal. Keep a list of “unofficial mentors” to learn from passively. Wednesday Tease: Catch Episode 298 this Wednesday: Stop Waiting for a Mentor to Magically Appear—Start Here Instead. Don’t miss it! Feeling overwhelmed in high-stakes moments? Download our latest free resource—The Clarity Under Pressure Toolkit—a concise guide to navigating uncertainty with poise. In just five minutes, you'll learn how to center yourself, assess the situation, and respond with confidence. This actionable toolkit equips you with the tools to stay grounded and make clear decisions when it matters most.     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.

• Erin’s website
• Erin’s Instagram
• Erin’s TikTok
• Erin’s LinkedIn
• improve it!’s website
• improve it!’s Instagram

🌟 Learn more about Workday Playdate: https://www.learntoimproveit.com/podcast-page
🎤 Book Erin to speak: https://www.learntoimproveit.com/keynote-speaker
📚 Workshops & Team Experiences: https://www.learntoimproveit.com/experiential-training
💌 Learn more about Erin: https://www.itserindiehl.com/meet-erin
📱 For more information on improve it! visit www.learntoimproveit.com.

If this conversation made you think differently about work, leadership, or building joyful teams, please follow Workday Playdate on Apple Podcasts or Spotify, leave a review, and share this episode with someone who could use more play in their workday.

In this episode of Workday Playdate, Erin throws out the five-year plan, the “dream job” myth, and that tired advice to just “follow your passion.” Instead, she’s joined by creative powerhouse and Mighty Forces founder Amanda Hirsch to help you rethink what career ownership actually looks like today. From office misfit to author, storyteller, and mom, Amanda shares the real talk behind taking back your path when no one else is handing you a roadmap. This episode is for anyone stuck in career limbo, burnt out on job titles, or wondering what’s next (without needing a full reinvention). Whether you're pivoting, plateauing, or plotting your next move, Erin and Amanda remind us: life is more improv than plan, and you're more ready than you think. Inside This Episode:

• Why waiting for “clarity” might be keeping you stuck
• The high cost of chasing the perfect job
• How to take action even when you don’t have it all figured out
• The power of storytelling in reclaiming your career narrative
• What Amanda learned from being a misfit—and why that might be your superpower
• One small step you can take this week to start owning your path

• 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.

• Amanda’s website
• Amanda’s LinkedIn
• Mighty Forces website
• Amanda’s Instagram
• Amanda’s TikTok

• Erin’s website
• Erin’s Instagram
• Erin’s TikTok
• Erin’s LinkedIn
• improve it!’s website
• improve it!’s Instagram

🌟 Learn more about Workday Playdate: https://www.learntoimproveit.com/podcast-page
🎤 Book Erin to speak: https://www.learntoimproveit.com/keynote-speaker
📚 Workshops & Team Experiences: https://www.learntoimproveit.com/experiential-training
💌 Learn more about Erin: https://www.itserindiehl.com/meet-erin
📱 For more information on improve it! visit www.learntoimproveit.com.

If this conversation made you think differently about work, leadership, or building joyful teams, please follow Workday Playdate on Apple Podcasts or Spotify, leave a review, and share this episode with someone who could use more play in their workday.