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May 21, 2025 32 mins

In this episode of the Learning from Smart People Podcast, Rob Oliver talks with Jessica Eastman Stewart, founder of the Joyfully Managed Team. A former nonprofit executive turned systems strategist, Jessica shares how leaders can create joyful, productive teams and more ease in their own leadership. From implementing a “Polish Week” to embracing authentic appreciation practices, this conversation is packed with insightful, practical advice to help your work life run smoother and feel better.

Here are some of the key points Rob and Jessica discuss:

  • Why joy might actually be the whole point of life—and leadership
  • The importance of diversity in team-building and decision-making
  • Why self-awareness matters when assembling or managing a team
  • How executive coaching can reveal hidden leadership blind spots
  • What a “Polish Week” is—and how it helps clean up cluttered systems
  • Examples of tasks you can tackle during a Polish Week (like decluttering tabs!)
  • How systems and structure can create space for more joy and ease
  • The myth of constant productivity and why “cleanup time” is essential
  • Strategies for managing tabs, bookmarks, inboxes, and brain clutter
  • The power of declaring “inbox bankruptcy” to reset your workflow
  • Why appreciation is one of the most effective joy-generators for teams
  • Different languages of appreciation and how to tailor them to your people
  • How leaders can use reminders and planning to make appreciation routine
  • Why symbolic gestures can be just as meaningful as tangible rewards
  • How Jessica uses email, Instagram, and freebies to spread joyful leadership tips

Jessica offers a free editable "Polish Week Checklist" to help you get started with tidying up your systems: https://bit.ly/Polish-Up-My-Systems

You can learn more about Jessica and connect with her through these links:

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