Is Your Boss Too Conservative? How “What If” Turns Into “What’s Next”

Some leaders look at the crazy ones—the Idea Monkeys—in their companies as painful distractions. Others look at their special brand of vision as the keys to the proverbial kingdom.

Which mindset is best? Do you feel comfortable challenging convention? Are you a (Ring)leader who encourages and focuses on dreaming, or do you think it is your job to save the company from the crazy Idea Monkeys? Your answer will determine whether your company leads or follows.


Now, before we go further, let me stress there is nothing wrong with being a fast-follower. Coca-Cola didn’t invent no-calorie soft drinks, but today it dominates the market with Diet Coke. Did Victoria’s Secret invent the lingerie specialty store? Nope. But they may soon be a $10 billion brand. HP did not invent the computer printer. You get the idea.

On a recent vacation to Barcelona, I stayed at a buddy’s house. Barcelona is a wonderfully busy city, housing some 1.6 million people in 39 square miles, so like many cities’ space, it is at a premium—literally. A guide told our group that many of his friends must spend more than 60 percent of their monthly pay on rent alone.

My buddy lives in one of the most sought-after neighborhoods in Barcelona. I know this is true because every taxi driver we hired told me so. Since my friend lives in a primo building, he gets the ultimate residential benefit: underground parking. Unfortunately, lack of space in the city means his garage eats cars for breakfast. It is so small and full of concrete pillars that every vehicle in it is scarred with scratches, dents and bruises from the ravenous columns throughout the garage.

All of this leads to a potentially world-changing question: Why do new cars have to be shiny, smooth and pristine? It is not as silly as it first sounds. People pay architects a premium for “weathered” New England cottages; vintage jewelry is often much more expensive than new; and don’t even get me started on leather jackets, boots and furniture. Imagine owning a car that became cooler the more beat-up it got. Imagine shunning body shops, car insurance agents and even car washes. You would hope for hail and park as close to the shopping carts as possible—the more dings the merrier!

Nonsense says the conservative business leader, the insurance agent, the repair shop and the car dealer—all of whom depend on shiny cars for a paycheck. Who in the world would buy a car that looks used the first day you get it? Yep, that’s probably the same reaction the person who suggested stonewashed jeans got from the head of marketing at Brand X. Now people are paying hundreds of dollars for weathered clothing.

Challenging convention is how the best new ideas happen. Again, pioneering a new market is costly, and radical innovations don’t always work. Remember Apple’s Newton? (If you don’t, you are not alone, and that’s the point.) But there is nothing better than radical innovation to get a company focused and its employees enthused. For a car-related company, the “rugged” look could be just the thing. At the very least, people would no longer fear dents and dings.

In addition to cramped parking lots, Barcelona is also the former home of Antonio Gaudi, an architect who dared to question convention. For example, he asked why we build homes, offices and churches containing straight lines when the natural world has almost no straight lines. His fanciful, organic buildings were ridiculed by many in his time, but today—thanks to works like La Sagrada Familia—he is considered a genius.

Speaking of homes, why are most still built one two-by-four at a time, under the rain, snow and warping sun, by hundreds of thousands of unconnected trades people? Can you imagine cars being built that way? Cars used to be built one bolt at a time until a guy named Ford questioned convention and created a manufacturing process that changed the world. My bet is that the carmakers of the time scoffed at his idea. They made money by putting together cars one at a time.

Would that have been you?

All great business ideas start with a question that challenges convention. And the greatest ideas of all are often met with cynicism at best and lobbyists and lawsuits at worst.

What were some of those questions? That’s easy.

Why can’t I trade stocks at home?

Why do I have to pay late fees?

Why do I need to call a lawyer for legal advice?

Why do I have to save all my information on a hard drive?

Why don’t cars drive themselves?

Why do I have to buy a whole album full of music when I only like one song?

Why can’t I just borrow bikes, cars and trucks when I need them?

Why does the post office have to deliver all the mail?

You may recognize some of these questions by the companies who asked them. Hint: E*TRADE, Netflix, LegalZoom, Rackspace, Google, iTunes, Zipcar, FedEx.

Is your team doing the asking or doing the scoffing?

Creative geniuses are natural challengers of convention, and companies that can empower these types of thinkers by backing them with the right culture and disciplined processes win.

Challenging what others won’t will often produce fresh insight and with it the opportunity to develop an industry-changing new product or service.

Where do you start? I recommend that you learn to recognize the telltale signs of challenging sacred conventions. The next time you find yourself getting angry about or laughing hysterically at a crazy new idea, stop for a minute and reflect. From my experience, there’s a pretty good chance that you’ll strike gold if you dig a little deeper.

First published on July 31, 2012.

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