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The most useful leadership book you’ve never read

A few years ago, after a long career in magazines, I realized I needed to reinvent myself professionally and entered the unfamiliar world of working at Big Retail. Like any newcomer, I had to learn to adapt. My biggest challenge was understanding how C Suite leadership works: why some decision makers are inherently more relevant, with a better handle on where retail is headed, not just where it has been. So I studied quarterly earnings records, a free crash course on How Leaders Think, as well as several classic business books, which often contained high-quality ideas that were better in theory than practice. Then I found it Geeks and Oddities: How Era, Values, and Defining Moments Shape Leaders.

This book was written by Warren G. Bennis and Robert J. Thomas, and was published by Harvard Business School Press in 2002. What potential value would a book on leadership published at that moment have today? Many contemporary readers will likely stumble upon the book’s title, which is highly objectionable (if not downright offensive) by today’s hot-button standards. What insights might we glean from a book that appeared when Google was just four years old and Mark Zuckerberg was finishing high school – a moment when many of us thought the digital revolution would solve all our problems?

Full of practical and implementation vision, Geeks and Geezers Provides a clear analysis of the similarities and differences between leaders. The lessons learned may be more important than ever in today’s turbulent retail environment.

Map vs compass command

The co-authors posit that while analogue-oriented “geeks” rely on maps, more digitally innovative “geeks” need only a compass. These navigational metaphors are apt, given how much corporate America likes to refer to business transformations as “journeys.”

It’s a simple and effective way to evaluate leadership ideas and actions, and this practical concept helps me quickly classify the type of executive I’m hired to support: The Map Leader sticks to well-worn paths and can only go where others have gone before. They follow predetermined methods and are fortunate to change their minds, even at the initial stage when the idea seems problematic on paper. When dealing with this type of leader, I do the best I can with what’s in front of me, saving my suggestions to help the team tasked with executing the strategy, flaws and all.

Geeks represent the leadership of the compass, and once they can identify the general direction in which a culture is headed, they are ready to find a path of their own making, even if the terrain is unfamiliar. Working on their strategic plans collaboratively is more productive because these leaders are attuned to the possibilities of discovery and uncertainty, making them flexible about how to get to their destination.

With the obvious caveat that a company’s problems are never single-rooted, I have a few examples of map/compass leadership problems that I’ve witnessed firsthand.

Navigating large retail businesses

Working for the newly appointed CEO of Compass at a famous American clothing company, whose map-shaped predecessor could not let go and remain on the board, was like watching two cars trying to park in the same place, paralyzing traffic on all sides and blocking progress. I’ve also watched a large American bed and bath organization declare bankruptcy because the “transformation” CEO, who was most likely hired because the board mistook him for a compass when it was actually a map, was unable to generate a strategy to target that goal. Specific clients of the company. Instead, he mechanically implemented merchandise tactics that had worked in his previous position at a competing retailer, alienating shoppers and collapsing the 50-year-old company in less than three years.

There are also instances where I was not behind the scenes, but observed and applied the Map-Compass theory strictly from the outside.

In February 2020, under Compass’s leadership, the first CEO from outside the company was appointed, LL Bean made his catwalk debut at New York Fashion Week In collaboration with Todd Snyder. A century-old utilitarian heritage brand meets the influence of a designer known for his relaxed modern style with classic American menswear that turned function into fashion: smart and relevant. And in October 2020, when the outdoors had a special appeal, the same CEO made a limited section of branded gear available on a third-party site (Zappos), something heritage retailers were loathe to do at the time.

Hybrid idealism

To me, retail map leaders are any executives who don’t care or respect the ongoing shifts in consumer culture in this volatile new era, easily demonstrated by mistakes like tone-deaf marketing emails advocating “spend more to save more.” And in financial call transcripts, they inevitably blame the dwindling numbers on the economy — irresponsible in an election year — or they blame their clients — as if, somehow, we’re not shopping enough. Their reactionary mentality and data blindness are even more evident when compared to the visionary statement made by Uniglo founder and CEO Tadashi Yanai during his presidency Year-end earnings call, when expectations were for 18% growth: “People are looking to reduce excess and frills and live simply in their own way.” compass. Great moment.

My favorite example is the map and compass hybrid: CeraVe skin care ads, featuring deadpan actor Michael Cera. What could have been a run-of-the-mill celebrity endorsement (map) became a clever and comedic compass, with the company reassuring us that despite what he may claim, Cera is not the founder of CeraVe, which was reinforced in a website containing an X-ed out photo of the actor, to Next to this message: “Developed in collaboration with dermatologists. Not Michael Cera. He is not a dermatologist.” I’ve never worked with Compass leaders who said yes to this idea, but I would have loved to have been in the room to have that discussion.


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