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In this episode of Workday Playdate, Erin shares the story of how one question—“How do people actually do this?”—helped her go from improv workshop facilitator with zero keynote bookings to speaking on stages at Amazon, LinkedIn, and major association conferences. Along the way, she discovered that curiosity is a career-building practice.
Erin breaks down the five curiosity practices she used to build her speaking career from scratch and how she applied those same practices to help team member Cristy von create her first keynote. Whether you’re navigating a career pivot, developing your leadership skills, or wondering what your next move should be, this episode will help you stop waiting for the perfect plan and start pulling the thread.
Inside This Episode:
- Curiosity Is a Practice, Not a Personality Trait: Discover why curiosity can be intentionally practiced and how asking better questions can fuel career growth, leadership, adaptability, and collaboration.
- Study People Who’ve Already Done It: Erin shares why researching people who are already where you want to go can reveal the path, shortcuts, and questions you didn’t know to ask.
- Learn Before You Hire: Before investing in a coach, mentor, or course, Erin explains how free content can help you do your homework, find the right fit, and make smarter career development decisions.
- Borrow the Room Before You Build Your Own: From free speaking gigs to the “rubber chicken circuit,” Erin shares why small stages can become your curiosity lab for practicing, gathering feedback, and refining your skills.
- Get Curious About the Community: You don’t have to figure everything out alone. Learn how finding the right professional community can expand your perspective, strengthen your network, and help you understand where you fit.
What to Do Now:
- Name Your Next Move: Identify one career move, skill, opportunity, or goal you want to pursue next. Don’t worry about the whole plan yet. Start with the question: How do people actually do this?
- Find the People Who Know: Identify two or three people who have already done the thing you want to do. Study their paths, content, and choices—and ask what you can learn from them.
- Learn Before You Invest: If you’re considering a coach, mentor, course, or program, start with their free content. Get curious before you get out your credit card.
Your Freebie
The Confident Leader’s Toolkit: Want to show up as a more confident, authentic leader without feeling like you have to perform? Download this practical 4-step guide to craft an intentional professional persona, so you can lead with clarity, confidence, and presence without burning yourself out.
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
Connect with Erin Diehl
🌟 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.
