Decisions as hypotheses and revisiting assumptions

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In a world that feels increasingly uncertain, making confident business decisions is hard. So we grasp for certainty. Numbers feel certain, but they often give us the false comfort of measuring the wrong things. In her book Embracing Uncertainty, Margaret Heffernan explores a different approach. Looking at artists, writers, and musicians, she asks what we can learn from people who produce extraordinary work in conditions where the future simply can’t be known. In this episode, Dart and Margaret discuss the hidden costs of certainty, why systems built around prediction can undermine human agency, and how artistic ways of working offer a different relationship to risk, failure, and learning.

Margaret Heffernan is an author, playwright, and former CEO who has run multiple businesses in the U.S. and U.K. Her TED Talks have been viewed more than fifteen million times.

In this episode, Dart and Margaret discuss:
- The pressure to be certain
- Why uncertainty is treated as a problem
- How prediction slides into control
- Why systems reduce human agency
- Why total certainty would strip away human choice
- How technology trains us to comply rather than think
- What artists do when the future can’t be known
- How power disrupts independent thinking
- The courage required to let go as a leader
- And other topics…

As Chief Executive of InfoMation Corporation, ZineZone Corporation, and then iCast Corporation, Margaret Heffernan was named one of the “Top 25” by Streaming Media magazine and one of the “Top 100 Media Executives” by The Hollywood Reporter. Her books include A Bigger Prize, Beyond Measure, Uncharted, and Willful Blindness, which was named one of the most important business books of the decade by the Financial Times.

Her TED Talks have been viewed more than fifteen million times. She is Professor of Practice at the University of Bath and, through Merryck & Co., mentors CEOs and senior executives of major global organizations. In 2023 she was inducted into the Thinkers50 Hall of Fame for her lasting contribution to management thinking.

Resources Mentioned:
Margaret’s books:
Embracing Uncertainty: How Writers, Musicians, and Artists Thrive in an Unpredictable World:  https://www.amazon.com/Embracing-Uncertainty-writers-musicians-unpredictable/dp/1447372670
Uncharted: How to Navigate the Future: https://www.amazon.com/Uncharted-Navigate-Future-Margaret-Heffernan/dp/198211262X
Willful Blindness: Why We Ignore the Obvious at Our Peril: https://www.amazon.com/Willful-Blindness-Ignore-Obvious-Peril/dp/0802777961

Connect with Margaret Heffernan:
Website: https://www.mheffernan.com/
LinkedIn: https://www.linkedin.com/in/margaret-heffernan-ab5205/

Work with Dart:
Dart is the CEO and co-founder of the work design firm 11fold. Build work that makes employees feel alive, connected to their work, and focused on what’s most important to the business. Book a call at 11fold.com.