Workday Playdate – Details, episodes & analysis

In this Workday Playdate, Erin tackles one of the most searched topics at work: feeling stuck in your career.

If you’ve ever thought, “Is this it?” or felt trapped between comfort and craving something more, this episode gives you a simple, actionable framework to stop spiraling and start moving. Career growth is about small, intentional steps that change your trajectory.

Inside This Episode:

• Feeling Stuck at Work? You’re Not Alone: Why burnout, disengagement, and lack of clarity are more common than you think, and what they’re really telling you.
• Energy Before Strategy: Why you can’t think your way out of burnout and how resetting your energy unlocks better decisions and career clarity.
• The “Improv Your Way Out” Framework: A five-step method to help you get unstuck, gain direction, and start taking action today.
• Call the Scene: How naming your current reality (honestly) is the first step to changing it.
• Yes, And Your Life: How to hold gratitude and desire for more—without guilt or self-judgment.
• Create Your Next Career Identity: Why stepping into a new “character” helps you align your actions with who you want to become.
• Baby Steps > Big Leaps: The secret to career change that actually sticks (hint: it’s not quitting your job tomorrow).
• Upgrade Your Environment: How the people around you either accelerate or drain your growth.
• Mindset, Habits, Environment: The real drivers of career fulfillment and how to start shifting all three.
• Small Moves, Big Career Shifts: Why consistent, aligned action beats waiting for the “perfect” moment every time.

What to Do Now:

1. Call It + Claim It: Write down what you’re currently tolerating at work—and what you actually want instead. Clarity creates momentum.
2. Take One Aligned Step: Don’t wait for a full plan. Send the email, start the conversation, or try something new this week. Small moves shift everything.
3. Upgrade Your Energy + Circle: Reset your mindset (hello, Positivity Without Pretending Toolkit) and spend more time with people who challenge and energize you.

Your Freebie

You don’t need to fake a good attitude to be a great leader. But chances are, you’ve been taught to push through instead of reset.

Enter your free resource: The Positivity Without Pretending Toolkit. A quick, human-centered reset designed to help you shift your mindset, refuel your energy, and show up with authenticity, especially on the hard days.  

Download the Positivity Without Pretending Toolkit here.

And thank you to our sponsors Intuit Quickbooks Payroll. To learn more visit:   https://quickbooks.intuit.com/workforce/

Connect with Erin Diehl x improve it! https://www.learntoimproveit.com/leadership-playground

• Leadership Playground online membership community
• 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.

In this Workday Playdate, Erin brings together innovation experts Rich Braden and Tessa Forshaw to challenge everything you thought you knew about creativity at work. This episode proves that innovation is not reserved for a select few, but something everyone can access through mindset, play, and small, intentional actions.If you’ve ever thought “I’m not the creative type,” this conversation will expand your definition of innovation and give you practical ways to bring more curiosity, experimentation, and whole-brained thinking into your day.About the Guests:Rich Braden is an innovation strategist, educator, and global speaker who helps organizations unlock creativity through human-centered design, play, and experimentation. With experience spanning corporate, startup, and academic environments, Rich is known for making innovation accessible, actionable, and energizing.Tessa Forshaw is a creativity and innovation expert, educator, and consultant focused on helping individuals and teams activate their innate creative capacity. Her work blends research, facilitation, and playful practice to challenge limiting beliefs and build cultures where innovation thrives.
Inside This Episode:

• Innovation Isn’t Exclusive: Why the biggest barrier to creativity is the myth that only certain people (or roles) are “allowed” to innovate.
• Whole-Brained Thinking Wins: How blending analytical rigor with creative exploration leads to better problem-solving, smarter decisions, and more innovative outcomes.
• The Play Advantage: Why improvisation, curiosity, and experimentation aren’t “nice to have”—they’re essential tools for unlocking new ideas and embracing failure.
• Mindset > Talent: How small, intentional mindset shifts can reignite creativity and help you move from “right vs. wrong” to “what’s possible?”
• Diverge, Then Converge: The airplane metaphor for brainstorming that helps you generate bold ideas and actually land them.
• Innovation in Action: Practical ways leaders can lower the bar, model experimentation, and create cultures where risk-taking is rewarded (not punished).
• Small Moves, Big Impact: Why innovation isn’t about big breakthroughs—it’s about consistent, everyday experimentation.

What to Do Now:

1. Try “Yes, And” Today: In your next meeting, build on someone’s idea before critiquing it. Watch how quickly energy and creativity shift.
2. Run a 10-Minute Diverge/Converge Sprint: Set a timer. Generate as many ideas as possible (no judgment), then switch modes and narrow to your top 1–2 actions.
3. Lower the Bar for Innovation: Pick one small experiment you can run this week.
4. Model the Behavior You Want: As a leader (or future leader), openly share a risk you took or a failure you learned from to create psychological safety for others.

Your FreebieYou already have strengths that make you a powerful leader. But chances are, one of them is doing more heavy lifting than you realize.Enter your free resource: The Human Leadership Edge Quiz. In just 10 quick questions, you’ll discover the leadership strength that sets you apart in the age of AI and how to use it more intentionally with your team.Take the Human Leadership Edge Quiz here.And thank you to our sponsors Intuit Quickbooks Payroll. To learn more visit:  https://quickbooks.intuit.com/workforce/
Connect with Rich Braden and Tessa Forshaw

• Rich’s LinkedIn
• Tessa’s LinkedIn
• Rich and Tessa’s book, innovation-ish

Connect with Erin Diehl x improve it!

• Leadership Playground online membership community
• 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.

In this Workday Playdate episode, Erin delivers a no-fluff leadership reset in How to Not Suck at Being a Boss. Erin breaks down how reactive habits quietly erode trust (hello burnout and disengagement) and replaces them with a five-step framework rooted in emotional awareness and clear communication.Inside This Episode:

• Autopilot Leadership: Why reactionary management drains morale and how to interrupt it
• Energy Sets the Tone: How your emotional state shapes culture, creativity, and results
• Listen to Understand: Stop fixing. Start hearing. (Yes, it changes everything.)
• Clear Expectations: Saying it out loud + writing it down = fewer misunderstandings
• Psychological Safety: Celebrating effort, learning, and growth to build real trust
• Lead Yourself First: Self-awareness, reflection, and owning mistakes like a pro
• The Five-Step Framework: Erin’s simple roadmap to becoming a more effective boss
• Improv at Work: Why “blocking the scene” kills connection—and what to do instead
• Yes-And Check-In: A practical exercise to deepen presence in daily team moments
• Embrace Imperfection: Leading with humanity beats leading with control

Who This Episode Is For:

• New managers and seasoned leaders who want to level up
• People leaders building emotionally safe, high-performing teams
• Humans navigating burnout, disengagement, or workplace uncertainty
• Remote and hybrid leaders craving deeper connection
• Anyone ready to lead with more empathy, clarity, and play

Your Playdate PracticeThe “Yes, And” Check-in: This week, when a team member comes to you with an issue, listen to understand, not to respond. Once they finish sharing, say, “Tell me more.” When they tell you more, say, “Yes I hear you, and here's how I can support you through this.”
Your FreebieYou want to support your people the same way you want to be supported—but in fast, emotionally charged moments, the right words can be hard to find.Enter, your free resource - Human Leadership in the Age of AI: An Empathy Playbook. It gives you a simple, 3-part list of human-first phrases you can use in meetings, emails, and one-on-ones.Empathy isn’t extra anymore. It’s essential. Download your Empathy Playbook 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.

What if the secret to conquering chaos, leading with confidence, and transforming stress into ease was as simple as your next breath? This week on the podcast, I sat down with breathwork expert Samantha Skelly to uncover the transformative power of intentional breathing. As the Founder of Pause Breathwork, Samantha Skelly is on a mission to help others unlock their infinite potential though breathwork. And her next big focus is making breathwork accessible & affordable to humanity, worldwide. From hilariously relatable mishaps (like sending a 10-year-old email to thousands) to life-changing strategies for managing energy and embracing joy, Samantha shared tools that could shift how we approach work, leadership, and even self-healing. Here were some of my favorite topics that we covered in the episode:  1. Managing Emotions Through Breathwork Samantha introduces the concept of consciously choosing your breath pattern to influence how you feel. Instead of letting anxiety take control, she suggests asking yourself what you want to feel, like confidence or clarity, and then adjusting your breath accordingly. By using deep, intentional breaths, you can activate the parasympathetic nervous system (the “rest and digest” state), helping you feel grounded, even in high-stress moments. Btw, if you’re looking for another breathwork expert on the pod, I think you’ll love this one with Erin Telford: The Art of Breathwork: Mastering Self-Love and Living Fully with Erin Telford 2. Real-Life Example of Breathwork Samantha recounts an intense experience right before recording this episode, where an old, out-of-date email was accidentally sent to her entire mailing list. She describes feeling an initial surge of rage, then using breathwork to regain her composure and approach the situation with clarity. By taking two deep breaths and extending the exhale, she shifted from a “fight-or-flight” response to a calmer, problem-solving mindset.  3. Shifting Mindsets from Stress to Ease I reflect on my own experience with stress in building my company, improve it!, sharing how I used to view stress as a badge of hard work. In response, Samantha offers a framework called LIFE: Lucrative, Impactful, Fun, and Easy. She encourages business owners to allow success to feel easy and fulfilling instead of always hard-earned, emphasizing the importance of self-love and creating a business model that sustains rather than drains energy. For all things breathwork and how to start incorporating it into your daily routine (and why you should!), listen to the full episode. It'll blow your mind with how simple it is + the impacts it can have.   No, You Hang Up First (Let’s Keep Connecting)

• Did today’s episode resonate with you? Leave us a review sharing your favorite breathwork 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 about breathwork that we can answer, or a question about something else? 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 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.

Show Links

• Purchase I See You! A Leader’s Guide to Energizing Your Team through Radical Empathy here and the Resource Guidebook that was built in conjunction with it here.

Connect with Samantha Skelly

• Samantha’s LinkedIn
• Samantha’s website
• Pause Breathwork website

Connect with Erin Diehl x improve it!

• Erin’s website
• Erin’s Instagram
• Erin’s LinkedIn

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

What if five minutes could change everything about how you lead, connect, and thrive? In today's episode, I reveal the powerful daily gratitude practice that shifted my mindset from scarcity to abundance—fueling not only my own growth, but transforming my team dynamics and leadership resilience. If you’re ready for a simple, impactful habit to elevate your life and work, this post is for you! Here’s a quick look at how gratitude can revolutionize your life and leadership, just as it did for me. 1. Gratitude Enhances Mental and Emotional Well-Being Gratitude has profound effects on mental health, reducing anxiety and depression while boosting overall mood. In this episode, I begin by sharing how this practice helped me refocus from a scarcity mindset—where stress and fear of “not enough” clouded my vision—to one of abundance and peace. Listing just a few daily “wins” and things I’m grateful for gives my mind a positive focal point and sets the tone for my day. Practicing gratitude helps you focus on what you have, rather than what you lack, cultivating a mindset that energizes and uplifts both you and your team. And if you’re looking for more info on forming an abundance mindset, I think you’ll love this ep: Episode 202: Self Worth = Net Worth: How to Live in Abundance 2. Fostering Team Relationships through Gratitude Integrating gratitude in a team setting doesn’t just enhance your day, but strengthens your team dynamics. I found that a simple habit of sharing appreciation with my team, both in private conversations and during meetings, lifted our collective spirit. This genuine acknowledgment brought cohesion and positivity to our interactions, boosting communication and morale. With everyone aligned and motivated, our work flowed better, and the energy shifted toward collaborative success, building a work environment that supports growth and achievement. 3. Building Resilience as a Leader With gratitude as a grounding practice, I noticed an increased resilience to daily challenges. For instance, when obstacles like travel delays or sudden issues arose, my gratitude practice allowed me to pause, reframe, and face these situations with a calmer, more adaptive mindset. Instead of letting stressful moments dictate my mood, I embraced each challenge as a lesson, focusing on what was still within my control. This approach not only supported my emotional regulation but also set a positive example for my team, showing them how to navigate challenges effectively. 4. Long-Term Leadership Impact Sticking to my gratitude practice has had a long-lasting impact on my leadership style, making me a more empathetic, balanced, and approachable leader. The effects extended beyond my professional life, enhancing my relationships as a parent, spouse, and friend. Embedding gratitude into your routine has a ripple effect—it supports personal growth and allows you to lead from a place of compassion and joy, ultimately making a positive impact on your entire team and community. 5. Start Your Own 5-Minute Gratitude Practice The episode outlines a straightforward gratitude practice: reflecting on past wins, listing things you’re grateful for now, and setting intentions for the day. This five-minute habit can be done verbally, digitally, or in a journal and serves as a daily reset, focusing your energy on the positives. By committing to this practice, you’ll find shifts in mindset and improved emotional regulation that benefit your leadership style, relationships, and personal growth. To dive deeper, listen to the full episode, and discover how gratitude can transform your leadership and inspire those around you. And if you remember nothing else from this gratitude practice, remember this: what you focus on grows. Start each day by honoring the good, and watch how it attracts more positivity, resilience, and connection into your life and leadership.   No, You Hang Up First (Let’s Keep Connecting)

• Did today’s episode resonate with you? Leave us a review sharing your favorite gratitude practice detail 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 about gratitude that we can answer, or a question about something else? 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 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? Click here, scroll to the bottom of the page, and we’ll meet you in your inbox. :)

Show Links

• Purchase I See You! A Leader’s Guide to Energizing Your Team through Radical Empathy here and the Resource Guidebook that was built in conjunction with it here.

Connect with Erin Diehl x improve it!

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

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

If you don’t take the time for yourself, the time will take itself and go elsewhere. Sound familiar, especially during the holidays? Yup, you’re not the only one. In today’s episode, Erin shares her 4-step strategy for finding balance between giving to yourself and giving to others during the holiday season. Erin also shares:

• What a “Bliss List” is and why you need to make one
• Why you should start making connections between the times you get sick to what’s going on in your personal and professional lives
• How to give yourself rewards (and actually schedule them) that contribute to your health holistically

If you’re looking for a new way to schedule self care—this is the episode for you. If you liked this episode, you can keep the party going with:

• Episode 256: How Can Leaders Embrace Career Curves? Insights from 'No Straight Path' Host Ashley Menzies Babatunde

 Show Links:

• Did today’s episode resonate with you? Leave us a review sharing your favorite self care strategy 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 about self care that we can answer, or a question about something else? Leave us a Speakpipe audio clip and we’ll answer it in an upcoming episode.
• Purchase I See You! A Leader’s Guide to Energizing Your Team through Radical Empathy here and the Resource Guidebook that was built in conjunction with it here.

Connect with Erin Diehl x improve it!:

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

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

Does your job search feel like it’s its own full-time job that’s not leading anywhere and also not paying you? You’re not alone. In response to this Q, Daisy Auger-Domínguez--a cross-sector global leader, speaker, author, and advisor on future readying workplaces, fostering inclusion, and addressing burnout at work—joins Erin today to discuss 4 strategies to avoid burnout while you’re in the heat of the job search. Daisy also shares:

• How to make your networking smarter, more focused, and consistent towards what you’re trying to accomplish in your career
• How to recognize burnout when it does occur as you’re job searching and what to do about it
• Why remembering what excites you about the job search is crucial to preventing burnout and actually getting the job you want

If you’re looking for a fresh perspective on the job search—this is the episode for you. If you liked this episode, you can keep the party going with:

• Episode 256: How Can Leaders Embrace Career Curves? Insights from 'No Straight Path' Host Ashley Menzies Babatunde

Show Links:

• Did today’s episode resonate with you? Leave us a review sharing your favorite strategy that Daisy shared 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 about job searching or burnout that we can answer, or a question about something else? Leave us a Speakpipe audio clip and we’ll answer it in an upcoming episode.

Connect with Daisy Auger-Domínguez:

• Daisy’s website
• Daisy’s books
• Daisy’s LinkedIn

Connect with Erin Diehl x improve it!:

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

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

When you're building inclusion for those around you at work, but you yourself are not feeling included, what do you do about that? This question from a listener really begs us to consider what’s within the locus of our control vs. what's not when it comes to inclusion at work. In response to this Q, Erin gives you 5 ways to go from excluded by others to including yourself and 5 ways to cope if leadership is excluding you, not necessarily your team/coworkers. Erin also shares:

• How to take situations that hurt your feelings and transform them into opportunities for empathy
• Why changing your environment could be the secret to feeling more included
• How to change your status in low stakes situations to lead to higher levels of brainstorming, connection, and consideration by your leadership team

If you’re looking for a fresh perspective on inclusion—this is the episode for you. If you liked this episode, you can keep the party going with:

• Episode 249: Demystifying Diversity with Daralyse Lyons: How Can Embracing Biracial Identity Lead to a More Inclusive Workplace Culture?

Show Links:

• Did today’s episode resonate with you? Leave us a review sharing your favorite coping mechanism that Erin shared 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 about inclusion that we can answer, or a question about something else? Leave us a Speakpipe audio clip and we’ll answer it in an upcoming episode.

Connect with Erin Diehl x improve it!:

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

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

Jon Macaskill and Will Schneider are hosts of the Men Talking Mindfulness Podcast—a project geared towards breaking barriers, fostering resilience, promoting peace, and developing a new masculine. Jon is a retired Navy SEAL and leadership consultant, and Will is a wellness consultant and teacher. In today’s episode, Jon and Will join Erin to discuss all things mindfulness in response to a listener question—particularly about how men can practice mindfulness inside and outside of work. Jon and Will share one important strategy that you can implement today to help create psychological safety for men at work. Jon and Will also share:

• Mindfulness practices you can start incorporating today
• An acronym for F.L.O.W. that you need to know
• A simple breathwork technique you can use anywhere, anytime

If you’re looking for a fresh perspective on mindfulness—this is the episode for you. If you liked this episode, you can keep the party going with:

• Episode 254: Busy Brain? Dr. Romie Shares Her Top Mindfulness Techniques for Stress Management

Show Links:

• Did today’s episode resonate with you? Leave us a review sharing something about this episode that you’re going to utilize 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 a question about mindfulness and how it plays out at work that we can answer? Leave us a Speakpipe audio clip and we’ll answer it in an upcoming episode.

Connect with Jon Macaskill and Will Schneider:

• Jon’s LinkedIn
• Will’s LinkedIn
• Men Talking Mindfulness podcast

Connect with Erin Diehl x improve it!:

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

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

In today’s episode, Erin answers a question from a listener about what to do when you start to outperform your boss. It’s juicy, it’s complicated, and...it’s manageable. Erin gives you a six-step strategy for how to handle a situation like this, especially if you’re overperforming and underappreciated. Erin also shares:

• The differences between Upset U and Upward U
• How to be the leader you want to be led by
• How to offer solutions when you receive criticism

If you’re looking for an answer to a tricky situation for now, for the future, or to share with a friend who’s going through this—this is the episode for you. Special sprinkles on top of this episode:

• How loglines can work in businesses and not just movies

If you liked this episode, you can keep the party going with:

• Episode 257: What Are the Secrets to Transforming Siloed Teams into Collaborative Powerhouses?

Show Links:

• Did today’s episode resonate with you? Leave us a review sharing something about this episode that you’re going to utilize 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 a question about leadership dynamics this month that we can answer? (ie, “What should I do if I don’t feel like I can be honest with my boss?”) Leave us a Speakpipe audio clip and we’ll answer it in an upcoming episode.

Connect with Erin Diehl x improve it!:

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

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