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The Monsters under the Desk

The true test of a strategic leader is being able to recognize, and having the courage to eradicate, subtle problematic ideas.

For me, the scariest Halloween stories have always been those with monsters under the bed: demonic creatures skulking in the innocuous settings of everyday life. The same is true with corporations. Often the most frightening threats to success lurk in everyday practices. So when my friend Bruno began to explain why he had resigned from his executive position at an enterprise software company by saying, “It seemed like such a minor thing at first,” I knew that something truly awful was going to follow.

Bruno was one of the company’s sales leaders. He was the “opener,” the company’s chief evangelist and visionary, gifted at persuading customers to transform their entire business with a software overhaul. But he rarely got a chance to personally close the deal.

At some key point in every major pitch, the company parachuted in another senior sales leader named Cliff. Cliff was the “closer.” He ran the group that sold much cheaper functional software packages. Inevitably, there would come a moment when the customer realized that his or her company couldn’t afford both Bruno’s comprehensive approach and Cliff’s upgrades. Most clients chose the expedient approach: buying Cliff’s smaller packages and postponing the purchase of Bruno’s enterprise solution. Not only did this mean a smaller sale, but it was terrible for the customer’s strategy. Bruno had to grit his teeth as he watched the companies delay making the changes they needed and lose ground to their more capable competitors.

Through all of this, Bruno and Cliff were friendly. Until one night when the two men stopped for a drink after a sale closed. Cliff raised a glass to Bruno: “I admire the way you set these deals up for us.”

“What do you mean?” asked Bruno.

“Well, by the time you’ve laid out their future,” Cliff said, “they realize that we really know their business. It makes it easier to sell them the upgrades.”

Bruno was speechless. Instead of regarding him as a rival with a contradictory philosophy, Cliff thought Bruno was just part of his team. Sitting there, Bruno had to stifle a wave of indignation. Because Cliff closed the deals, he was always credited with higher sales — which meant he was fast-tracked and would be promoted sooner. What stung the most, Bruno said, was the realization that everyone else thought he was playing Cliff’s game, and that he too, then, must have thought that Cliff’s approach was better than his own.

These monsters under the bed — or desk — are subtler than the ones in most Halloween fare. They take the form of prevalent but unnoticed and stubborn ideas that consistently, mindlessly destroy value. It can take real leadership even to recognize a problematic idea, let alone supplant it.

In Bruno’s case, three such monsters lurked under his desk. First, there was an idea about reward — that whoever delivers the end result deserves the lion’s share of credit, no matter how many others laid the groundwork. Second, an idea about selling for the short term — that you always sell whatever you can, as soon as you can, because that’s what counts in the performance data. And third, a deal is a deal — that every deal is considered on the basis of the revenue it generates, regardless of its impact on the client or the company.

Deals like these are addictive. As credit accrued to Cliff at Bruno’s expense, it made it harder to reverse course. Worse still, Bruno’s instinct that they would lose customers had proved prescient. Some were already gravitating away from the company; as they adopted cloud computing, it became easier for them to switch systems and to associate Bruno’s company with all those costly legacy upgrades.

Stories like this help explain why leadership remains a compelling topic in management literature. (It’s one of strategy+business’s most popular topics.) It’s not because people expect to find answers. Reliable universal answers are rare in leadership writing.

But we know that, as leaders, we are constantly fighting monsters under the desk. The entrenched habits that we hate are hard to see as such. They often seem like the right thing to do, and even as we hate them, we do them anyway. Who, after all, could argue against selling as much as we can this month? Or giving credit to the people who close a deal? Or valuing deals according to their revenues?

The entrenched habits that we hate are hard to see because they’re embedded in everyday practice.

That nagging inner feeling that something is wrong, and the willingness to listen to it, is the first step toward truly strategic leadership. As Bruno’s story shows, it’s difficult to take that step, even for the best of us. Sometimes you really don’t think you’ll ever win, because the monster under the desk is really, as in all horror stories, residing inside yourself. How do you bring out that story without sounding shrill? How do you make your colleagues see it in themselves and change their habits?

The answer is simple to say: You learn to name the monsters, and talk about them, dispassionately and repeatedly. You learn patience and persistence. And you decide, in the end, how much you care. If you care enough about the enterprise, you have a huge task ahead of you. That’s the task we call leadership.

Art Kleiner

Art Kleiner was formerly editor-in-chief of strategy+business.

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