THE ART OF BEWILDERMENT | A NECESSARY DOSE OF FEELING LOST

When making decisions in business, being in the state of bewilderment is the ultimate taboo. People shift in their chairs in discomfort, conversations stall, facial expressions shift downwards, as if to say, “We’re closed.”

For leadership, the taboo is even more intense. After all, aren’t leaders supposed to know where to steer the group?

Bewilderment always feels like it’s brand new, but it’s actually a very old concept in Western thought. The word “bewilder” is rooted the now-obsolete word “wilder”, means “to go astray”.

Bewilderment is the foundation of what is known as the Hero’s Journey: In movies, poems, plays and stories, heroes spend a lot more time in the wilderness than they do back at home, being celebrated. But, in business, bewilderment is inconvenient, scary–it feels like it messes things up.

In my own career, however, I have come to trust it. Bewilderment is THE critical element of doing my job well. It is my personal secret ingredient to success. And so, I have become very well-acquainted with how it can serve a business. But, you have to get the dosage right. Knowing how long a specific organization can stay in bewilderment, and for what clear purpose, what belongs in the thinking when we’re there, and when to migrate out of bewilderment and into integration, is a skill that everyone can develop with time and experience.

A good example of this is an Analytics Maturity assessment, where the job to be done is to determine how well a company’s data is serving its business, and ultimately to give a score and a roadmap. This requires going intimately into a company’s operations, team ways of working, decision-making and leadership dynamic, analytics culture, and, of course, its data. You’re doing stakeholder interviews, kicking the tires on data and reporting, determining organizational weak points in operations and/or the need for leadership, and designing a pathway to stable business intelligence in what is often very much a “pathless wood”.

But here’s why it all matters–without bewilderment, you miss the crucial details that drive success. Every company, every business venture, every marketing strategy is unique, and without allowing time in your business processes to consider the details and to reflect on those details, you’ll be following a course that isn’t designed for your company.

How to use bewilderment? Structure time around it. Allow 10 minutes of free writing on a page, or 10 minutes of open discussion. Make a clear container–establish that this is a safe space to be open, where no idea is off the table. Use anonymity if you have to. And before you go in, set a clear end-date or end-time, and a clear goal.

Time spent in bewilderment is not time lost–it’s integration, gained. That is bewilderment’s ultimate paradox, and its ultimate gift to business.

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