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improve it! Podcast – Developing Teams and Leaders Through Play, Improv & Experiential Learning

May 13, 2020

“You gotta get through the discomfort of ‘this doesn’t look like something I have experienced and am comfortable with,’ but it’s going to push us ultimately, and hopefully into something better.” - Kyle Stapleton



Each week, your failed it! podcast host and improve it! founder Erin Diehl, will take you on a comedic journey that flips the “highlight reel” of Instagram on its head and shows you the grit, creativity and determination it takes to overcome your disappointments, embrace the suck, and design the career you’ve only dreamed about. 


On today’s failed it! episode, host Erin Diehl introduces the Senior Manager of Culture & Experience at WarnerMedia Studios, Kyle Stapleton to speak about his lessons in failure and his embodiment in creating soulful, human work experiences.


Welcome to failed it!


Tune in to how innovator Kyle proves that the fortune sure does favor the bold by the highlights below:

  • [5:49] Kyle’s failure resume
  • [13:44] If you’re an innovator, surround yourself with integrators
  • [14:14] Book - Rocket Fuel by Gino Wickman & Mark C. Winters
  • [16:55] The quarantine adjustment using the innovator mindset
  • [19:30] Breaking down old habits and embracing change; be smarter and work different
  • [20:06] Quarantine gave a chance to pause and reflect
  • [23:01] improve it!’s WFH (work from home) membership
  • [24:49] Chicken Champion Moment (getting comfortable with the uncomfortable)
  • [26:11] The fortune favors the bold - value of speaking up
  • [31:53] 3 action items for others to improve themselves (be a rebel, make sure you’re serving, take the opportunity to clean your slate)
  • [39:58] Today, Kyle failed at…
  • [41:13] With every failure, you learn
  • [41:30] Fail Yeah!
  • [43:13] You can follow Kyle on Twitter and LinkedIn
  • [43:40] Screenshot you listening and tag us using #faileditpodcast!
    • Instagram: @learntoimproveit
    • Facebook: @improveit


Kyle Stapleton is Sr. Manager of Culture and Experience for WarnerMedia Studios, the creative production engine that supports WarnerMedia brands like TBS, TNT, HBO Max,Cartoon Network, [adult swim], NBA TV, truTV, CNN, Bleacher Report, and more. There he fosters an environment that empowers top creative talent to shape culture through stories. This entails working across the employee life cycle, from talent attraction and onboarding through engagement, inclusion, and development. His team’s goal is to make WarnerMedia the world’s preeminent destination for multimedia creatives.


As part of his interest in designing more soulful, human work experiences, Kyle co-founded the Atlanta chapter of CULTURE LABx, a global community of EX professionals experimenting with the future of work. He also advises and champions organizations working at the intersection of Atlanta’s cultural impact and civil rights legacy, such as Atlanta Influences Everything, Generator, and Future Foundation.


Kyle also co-hosts TuneDig, a podcast about music discovery born from years of working with record stores. He earned his bachelor’s and MBA from Georgia State University’s Robinson College of Business. He and his wife Caralee, a visual artist and curator, are proud lifelong ATLiens.



Erin Diehl is the founder and Chief “Yes, And” officer of improve it! and host of the failed it! Podcast. She’s a performer, facilitator and professional risk-taker who lives by the mantra, “get comfortable with the uncomfortable.” Through a series of unrelated dares, Erin has created improve it!, a unique professional development company that pushes others to laugh, learn and grow. Her work with clients such as United Airlines, PepsiCo, Groupon, Deloitte, Motorola, Walgreens, and The Obama Foundation earned her the 2014 Chicago RedEye Big Idea Award and has nominated her for the 2015-2019 Chicago Innovations Award.


This graduate from Clemson University is a former experiential marketing and recruiting professional as well as a veteran improviser from the top improvisational training programs in Chicago, including The Second City, i.O. Theater, and The Annoyance Theatre.


When she is not playing pretend or facilitating, she enjoys running by the lake and patio dinners with her husband and son, and their eight pound toy poodle, BIGG Diehl.


You can follow the failed it! Podcast @learntoimproveit on Instagram and facebook, and you can follow Erin here on Instagram. We can’t wait to connect with you online!