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When Experience Is Your Biggest Weakness

The leadership talents you've already mastered are not necessarily the ones that you'll need in the future.

There are many talents and skills required for leading a company today that are radically different from the ones required in decades past.

In a recent New Yorker article focused on departed Target CEO Gregg Steinhafel, Amy Merrick provides a fantastic illustration: 

Even after he became the CEO, earning millions of dollars a year, Steinhafel tried to see his stores as Target's customers might. "I come in and I want to see, How does the store feel?" he told Marketplace's Kai Ryssdal, in 2009. "Is it clean? Are the brand standards right? I quickly look at the check lane--is there anybody waiting in line? Am I excited to be here?" In February of this year, on a visit to a store, he pointed out that its entrance didn't have enough shopping carts and that a mannequin's arm was out of place, according to a Wall Street Journal profile.

All of which, Merrick points out, remains important in retail settings. But none of it equipped Steinhafel to "protect his business or save his job" after last year's data breach at Target's registers.

On some level, it's sad story. Steinhafel, Merrick writes, "was among the best in the business at old-school retail. He took over Target's merchandising, in 1994, when the company was still a nondescript discounter and, over the following two decades, helped transform it into a 'cheap chic' retailer that signed partnerships with designers such as Michael Graves and Isaac Mizrahi."

In other words, he was a gifted leader who had a vision and produced results. But abundant as they were, his skills and talents did not prepare him to lead Target through the data breach. 

What can you learn from this? The chief takeaway is learning to identify your leadership blind spots. 

Hal Gregersen, executive director of the MIT Leadership Center and a senior lecturer at the MIT Sloan School of Management, told me not long ago that business leaders are often blind to the questions they should be asking for two reasons:

1. In most organizations, you get promoted not for asking questions but for providing answers. You advance by voicing the glib sound bites, not the edgy hypotheticals.

2. Once you ascend to the CEO seat, there are barriers precluding your interaction with anyone who might nag you with those hypotheticals.

For example, only a select few employees--who are also high-ranking--report to you directly. And those direct reports tend to kiss your ass and prepare you with "talking points" that will make sure no one gets upset. "It's an insulated world, where the blind spot is not explored," says Gregersen.

To identify your blind spot, Gregersen advises taking actions that will remove the insulation from your world. You might, for example, create a team of independent thinkers, devoted strictly to exploring both your and your organization's blind spots.

You might also set aside a few minutes each day (Gregersen suggests four minutes) to sit in solitude and ponder these questions for yourself. Remember, you don't have to know the answers right away. A solid start is just asking the right questions. 

And if the case of Steinhafel is on your mind, one of those questions would probably be: "How can I address the unnerving reality that my life experience is potentially a weakness, rather than source of wisdom?"

Addressing that reality won't be easy. But identifying it is the only way to begin.

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