Leadership and Uncertainty: A deep dive into unknown unknowns

Continuing on the uncertainty theme, I am hosting a series of conversations to contemplate and grapple with how we lead, learn, educate, and think in a manifestly uncertain world. The first discussion in this series of live webinars is Friday, May 22.

The present invites us to contemplate and grapple with how we lead, learn, educate, and think in a manifestly uncertain world. At the same time, media and messaging bombards us with predictions and “answers” about the future, as if to reinforce our obsession with control and certainty. What seems to be missing, at least for me personally, is a place to ponder the nature of uncertainty itself — in intentional conversation with other people. (Socially distanced, of course.)

So, I asked some fascinating and intriguing leaders and contemplatives to join me over a series of webinar discussions about uncertainty. In my invitation to these panelists, I described the modus operandi: “These sessions are intended to be informal conversations that explore uncertainty with fellow colleagues, thinkers, and leaders who are interested in learning from/with one another, publicly.” This isn’t about the answers, it’s about the questions.

Six conversations are scheduled, with six cohorts of guests. Conversations will be livestreamed and later available via podcast. The first conversation is this Friday. Please join us in real-time, if you are able.


Conversation 1 – Friday, May 22, 9-10 AM EST (Register)
Conversation 2 – Wednesday, May 27, 12-1PM EST (Register)
Conversation 3 – Friday, May 29, 12-1PM EST (Register)
Conversation 4 – Monday, June 1, 8:30 PM – 9:30 PM EST (Register)
Conversation 5 – Tuesday, June 2, 8:30 PM – 9:30 PM EST (Register)
Conversation 6 – Wednesday, June 3, 12-1PM EST (Register)

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Shelley, James. (2020). 'Leadership and Uncertainty: A deep dive into unknown unknowns' Originally published on May 20, 2020. Cited version last modified on October 31, 2020. Accessed on December 2, 2020. Licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License. Permalink: https://jamesshelley.com?p=16674
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One thought on “Leadership and Uncertainty: A deep dive into unknown unknowns

  1. Hi James,
    Sorry I missed your first conversations on the topic of uncertainty. I will receive it later as a podcast. I will try to register for your on May 27.
    The topic of uncertainty is definitely required during this very unpredictable time. I believe that societies have always existed with the concept of uncertainty …in many ways this concept was the only certainty in the lives of our ancestors who were not capable of understanding or controlling many natural forces in their lives. They lived with little expectation that life might improve from generation to generation. Only in our industrial, post industrial and computerized societies has the concept of creating a ‘ better’ world under the guise of ‘progress’ been enunciated as a ‘normal’.
    As we gradually, and not so gradually, raised our individual and community expectations for the future over the centuries, we began the process of believing that human kind could actually control its own destiny oblivious to the harm we were inflicting upon the earth.
    These increased expectations are accompanied by a degree of disappointment and uncertainty when these expectations are not met. Former generations lived a simpler life with personal and societal visions that reflected their limited ability to change their world professionally and personally.
    A more complex society innately creates more stress and uncertainty simply because these expectations puts pressure upon each individual to ‘ perform’.
    This pandemic has only exasperated our society’s preoccupation with stress; it did not create an era of uncertainty…it only reinforced our inability and desire to control our lives. The realization that this premise is untrue has further eroded our obsession with creating a ‘ certain’ future.

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