March 25, 2025
Episode 131: How Uncertainty Improves Teamwork with Maggie Jackson
In this episode of The Future of Teamwork, Dane Groeneveld speaks with Maggie Jackson—journalist, social critic, and author of Uncertain: The Wisdom and Wonder of Being Unsure—about the power of not knowing and how it shapes collaboration, leadership, and human connection.
Together, they explore how modern work environments often reward certainty and speed, even when deeper thinking is needed. Maggie shares why uncertainty isn’t a flaw to fix, but a space where better questions—and better teamwork—can take shape. Whether you’re leading a team or contributing to one, this conversation offers a fresh lens on how to navigate complexity, listen more openly, and make room for curiosity.
How Uncertainty Improves Teamwork with Maggie Jackson
Guest Bio
Maggie Jackson is an award-winning author and social critic with a global reach. Her latest book, Uncertain: The Wisdom and Wonder of Being Unsure, explores why we should seek _not-_knowing in an era of angst and flux. Nominated for a National Book Award, Uncertain was named a best book of the year by the Next Big Idea Club (curated by Malcolm Gladwell, Susan Cain, Dan Pink and Adam Grant), as well as by Library Journal, Greater Good magazine, and the Artificiality Institute. Uncertain is the Independent Publishers of New England 2024 “Nonfiction Book of the Year.”
A past foreign correspondent in Asia and Europe and a popular former Boston Globe columnist, Jackson also has written for many major U.S. and international publications, including The New York Times. Her acclaimed book Distracted (2nd ed., 2018), now lauded as a modern classic, sparked a global conversation on the costs of fragmenting our attention. Known for her prescient writings on social trends, Jackson has advised leading executives, scientists, educators, and change-makers worldwide. She swims nearly every day year-round in the Atlantic – a pursuit she calls her “daily dose of uncertainty.”
Key Takeaways
00:00 Introduction to the Future of Teamwork Podcast
01:24 Meet Maggie Jackson: Author and Social Critic
02:01 From Foreign Correspondent to Exploring Technology’s Impact on Humanity
04:07 The Trilogy of Uncertainty
05:37 The Impact of Technology on Attention and Connection
10:14 The Role of Uncertainty in Leadership and Teams
16:21 The Power of Disagreement and Diverse Perspectives
20:09 Harnessing Uncertainty for Better Decision-Making
23:27 The Importance of Process Over Outcome
28:03 Embracing Strategic Uncertainty
28:59 Tolerance of Uncertainty: A Key Personality Trait
30:55 Building Resilience Through Exposure Therapy
33:03 Leadership and Uncertainty in High-Stakes Environments
37:06 The Power of Maybe and Positive Disagreement
42:41 Feedback and Uncertainty in the Workplace
47:02 The Role of Uncertainty in Creativity and Relationships
53:06 Final Thoughts and Resources
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