68. Madoff and Cramer Plead Guilty: How to Respond When Guilty as Charged

In an ironic coincidence, two prominent public figures pleaded guilty on the same day in March 2009: Bernie Madoff to a judge, and Jim Cramer to Jon Stewart. Mr. Madoff, caught red-handed on 11 felony counts of swindling stocks, had to confess; Mr. Cramer, caught red-handed of hyping stocks, did not. Hyperbole is not a crime—yet. But if Mr. Cramer’s admissions were an effort to tell the public that he intended no malice, he could have done so more positively. Instead, he withered in the line of Mr. Stewart’s fire.

Jim Cramer certainly had the wherewithal to stand up for himself in a contentious exchange, such as his appearance on The Daily ShowF68.1 was sure to be. As a Harvard-trained attorney (including a stint as a research assistant to the famously contentious Alan Dershowitz) and as a seasoned television professional, Mr. Cramer surely knew a thing or two about handling tough questions. Moreover, Mr. Stewart’s questions were not surprising—he had spent the three prior episodes that week trashing Mr. Cramer and CNBC. USA TodayF68.2 had touted Mr. Cramer’s appearance with a banner headline, and Business WeekF68.3 had called it the “week-long match of the century.” Mr. Stewart himself previewed the encounter as a “battle between a man who makes people laugh for a living and whatever people think I do.”

Yet when Jim Cramer took his place in the hot seat, he capitulated completely. As Jon Stewart repeatedly berated him, Mr. Cramer repeatedly agreed, saying, “Okay,” or “You’re right,” or offering shoulda’, woulda’, coulda’ replies. And when not agreeing with Mr. Stewart’s charges, Mr. Cramer shifted the blame to “the regulators” or to the “lying CEOs.”

Worse still was Mr. Cramer’s presentation. On his own CNBC show, Mad Money, he usually stomps around the set shouting loudly and waving his arms wildly. Seated across from Mr. Stewart, Mr. Cramer spent most of his time docilely nodding his head in agreement or shrugging his shoulders, his arms splayed open in submission.

Did Jim Cramer prepare himself, as anyone with a modicum of experience with tough Q&A sessions would? Did he anticipate a list of the worst-case questions? In fact, before Mr. Cramer came onstage, Mr. Stewart performed his own mock preparation session: responding to shouted questions from off-screen voices while seated against a bare brick wall, under the glare of a naked light bulb.

What could Jim Cramer have been thinking? If he wanted to make amends to the public he had misled, he could have done so on his own turf, to his own unseen and unheard audience. Instead, he went into the lion’s den and submitted to a scathing dressing-down from Mr. Stewart.

Even Jon Stewart was perplexed. In his closing remarks, he turned to the camera and said, “I hope that was as uncomfortable to watch as it was to do.”

We all make missteps or mistakes at some point in our careers. If those mistakes are similar to those of Messrs. Madoff and Cramer, they are matters of accountability and are beyond repair. If they are honest mistakes, here is how to handle them: Take a lesson from Jon Stewart’s mock grilling. Prepare a list of tough questions about your blunder and have a colleague or colleagues fire them at you in a practice session. In your answers, be completely honest and admit your responsibility, but then promptly go beyond your admission and offer what corrections you have made or will make. Give more weight to your corrections than to your admissions. Repeat the mock grilling until you become fluent and succinct. By the time you step into the real Q&A session, unlike Jim Cramer, you will present a positive image.

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