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Ugly-Sweater Leadership Moments

Wise leaders actively seek the truth they don't want to find.

(originally published by Booz & Company)

The lead-up to the Olympics brings plenty of opportunities for us all to anticipate, and reflect on, the thrill of victory and the agony of defeat. Life, and leadership, serve them up in large measure. Sometimes, whether we win or lose is out of our hands—but often we play both victim and villain.

I wonder who’s to blame for the U.S.’s ugly Olympics sweater. While I would be proud to represent my country and wear its colors, it would be hard to happily don a sweater that evokes images of a repurposed bedroom quilt. Imagining the creative process of Ralph Lauren’s team brings a smile to my face: Sitting in a teepee nestled in wildflowers on the Double RL Ranch, the team pitches their ideas. Ralph Lauren sees the crazy quilt cardigan and leans forward, apparently seeing what others cannot, and signals his approval. Aghast, Ralph’s minions are dumbstruck and afraid to speak their minds—sure that, in the process of designing polo shirts adorned with ponies of various sizes, they have lost their artistic mojo.

We all have our ugly-sweater leadership moments. Years ago, while on a business trip, my boss called me late at night with some unexpected and unpleasant news. While closing the books for the year, one of my direct reports had submitted a stack of unpaid invoices totaling in the high six figures. Throughout the year, he had buried them in his desk drawer, with the intention of paying them as he could, without blowing his budget. But he never did because he never could. As the year came to a close, so did my reputation as a fiscally sound leader.

Whose fault was it? He had the opportunity to submit a new forecast on a monthly basis; we all worked together collaboratively to consolidate our forecasts and adjust our operating plans to hit the overall target. But we never discussed the option of exceeding our budget because in our company, and in my department, it just wasn’t done.

I realized, then, that the monthly forecasting meetings were a joke. We’d ask the question, “Are you going to hit your annual budget?” But anything other than “yes” was an unacceptable answer. My sneaky employee understood the rules of the game: Don’t tell me the truth, just tell me what I want to hear. So while I was disappointed in him, I was even more disappointed in myself.

Leaders do this frequently: They set up a good-news culture, where the devil’s advocate or truth-teller is quickly dismissed. When walking the halls, they ask ineffective questions like, “Is everything okay?” or “How are things going?” Because really, they just want to hear soothing, but information-free, non-answers like “yes” and “great!”

Wise leaders, however, have the courage to seek information they don’t want to hear, by asking questions in a way that makes it easy for people to tell the truth. So, how can you do that?

Seize the moment by being alert and available. People who have something to say, but not the nerve to say it, are often compelled to find opportunities to get closer to the bright lights of power and pose seemingly innocuous questions. Leaders who find that they are being “stalked” in this manner should recognize that people with less power often hide behind questions with the hope that those with more power will allow them to share what’s on their mind. In these situations, leaders should learn to ask questions, rather than answer them.

Leaders should learn to ask questions, rather than answer them.

Expose people’s fears. Sometimes, it’s best to pose questions that assume there’s room for improvement such as “What keeps you up at night?” or “How are we making it hard for you to do your job?” Also, shift perspectives and explore risks by asking questions such as “What may cause us to fall short?” or “If you could have three wishes to help guarantee success, what would they be?”

Promote safety by connecting personally and informally. Try having your next meeting in a coffee shop rather than a conference room (or teepee) and act on the information you gather there without divulging the source.

Ugly-sweater leaders are often dumbfounded when they find that their minions have held back important information. And I am always dumbfounded by their dumbfounded-ness. After all, who in their right mind would expect those further down the power grid to reveal the cold, hard truth without significant encouragement? I recently found myself in this situation, with important information that I decided not to tell. When I examined my motives, I realized that I was unwilling to assume the risk of communicating into a black hole, void of senior-level relationships or context. I reasoned that what I had to say would not—could not—be heard in a top-down culture where relationships were tight-knit and decisions and information were closely held.

Leaders who are unable to tap into the truth only have themselves to blame when things go wrong. Get out of your head and step off your podium (or out of your teepee, as it were). Have the courage to seek the truth you don’t want to find by trading in the power of your position for the power of information.

Susan Cramm

Susan Cramm, leadership coach, author, and former CFO and CIO, is committed to the principle that the best leaders take care of business by taking care of the people entrusted to their care.


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