TLP472: Embracing Uncertainty with Dr. Margaret Heffernan

Dr. Margaret Heffernan has written six books including “Willful Blindness: Why We Ignore the Obvious at Our Peril” and “Uncharted: How to Navigate the Future,” both widely recognized as top business books.

Dr. Heffernan returns to the Leadership Podcast with insights from her new book “Embracing Uncertainty: How writers, musicians and artists thrive in an unpredictable world.” She challenges conventional wisdom on how we think about decision-making in uncertain times. She reveals why leaders need to step away from predictive algorithms and reclaim their human capacity for intuition.

She discusses the difference between healthy uncertainty and harmful vagueness, sharing practical techniques for leaders who want to make better decisions without drowning in endless analysis. She reveals why agenda-free meetings often produce better results than structured ones, and how silence can be more powerful than speaking.

Through personal examples, Dr. Heffernan demonstrates how apparent failures can become unexpected successes when we learn to sit with uncertainty rather than rush to conclusions.

This episode provides actionable insights for leaders who want to navigate uncertainty with confidence, make decisions with incomplete information, and create space for the unexpected insights that drive breakthrough thinking.

You can find episode 472 wherever you get your podcasts!

Watch this Episode on YouTube | Dr. Margaret Heffernan on Embracing Uncertainty

https://youtu.be/c_jN4HXCa80

Key Takeaways

[03:32] Dr. Heffernan reveals what’s not in her public bio: she’s been trying to grow vegetables for about 10 years and is still absolutely terrible at it, and she’s currently learning Italian, which is a deeply humbling experience.

[04:53] Dr. Heffernan explains that leaders can reclaim intuition for better decision-making by absorbing quality information through everyday observations—like walking city streets or eavesdropping on conversations—to “restock their mental kitchen” with rich ingredients that will inform future choices when needed.

[10:11] Dr. Heffernan confirms that when you slow down, thoughts bubble to the surface – some mundane like “oh God, I forgot to feed the cat,” others valuable like identifying the right person for a job that your brain was processing subconsciously.

[11:59] Dr. Heffernan distinguishes between necessary ambiguity and harmful vagueness by explaining that decisions are always ambiguous because they’re “hypotheses about the future,” but harmful vagueness occurs when leaders don’t ask clear questions or establish what decision needs to be made.

[17:09] Dr. Heffernan describes transforming a board she chairs from having overly strict agendas to focusing on “what are the three most important things we need to be talking about right now,” explaining she has more often seen time wasted from detailed agendas than loose ones.

[20:33] Dr. Heffernan explains that “action is how you search” – you can talk, think, and research forever, but the only way to know if something will work is to start, emphasizing that what really matters is beginning, not necessarily where you start.

[23:06] Dr. Heffernan suggests that risk tolerance may actually be lower than ever before, but people’s level of anxiety drives them to reduce risk, working with wealthy companies whose “risk aversion is almost tangible” despite having enormous resources.

[24:36] Dr. Heffernan acknowledges that artists and musicians must be vulnerable to put themselves out there, but explains that most people she’s worked with have high risk tolerance because “if you’re going to do something meaningful and worthwhile, probably going to be something you haven’t done before.”

[26:35] Dr. Heffernan shares that her book “Willful Blindness” initially seemed like a failure with only a couple of reviews after six months, but took off after making the Financial Times Business Book Award longlist and continues to have readers over a decade later.

[28:53] Dr. Heffernan explains her motivation for writing “Embracing Uncertainty” stems from her belief that “the marginalization of the humanities and the arts, the defunding of the arts” is doing “immense harm” and represents “a gigantic loss, not just to the arts, but to all aspects of life.”

[32:01] Dr. Heffernan outlines her ideal leadership retreat opening: “sending people out for a walk and coming back to report what they saw,” explaining this practice “wandering around stuff” and would reveal amazingly different observations from different people.

[33:43] Dr. Heffernan suggests the better instruction for the walking exercise would be “noticed” rather than “saw” because “you could notice in all sorts of different ways,” allowing people to focus on hearing, feeling, or thinking differently.

[40:57] Dr. Heffernan explains she’s become “much less concerned about planning now,” leaving more margins for things to go wrong and scheduling less frantically to create “space and time for things to happen.”

[42:39] Dr. Heffernan describes a transformative experiment where she appointed herself “the listener” in meetings, discovering that when you’re not looking for moments to speak, “you actually are listening to the person who’s speaking instead of rehearsing in your mind what you’re going to say next.”

[45:48] Dr. Heffernan concludes that leaders should remember “what’s uncertain is a whole range of things that are possible” and warns against “demanding too much certainty too fast” because “what’s certain is what’s known and something you’ve done before,” while innovation requires exploring uncertainty rather than shutting it down.

[46:57] And remember…“Uncertainty is a very good thing: it’s the beginning of an investigation, and the investigation should never end.” – Tim Crouch

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