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Working for Entrepreneurs – A Survival Guide

“But I don’t want to go among mad people,” Alice remarked.
“Oh, you can’t help that,” said the Cat: “we’re all mad here. I’m mad. You’re mad.”
“How do you know I’m mad?” said Alice.
“You must be,” said the Cat, or you wouldn’t have come here.”

Lewis Carroll, Alice in Wonderland

The executive was feeling pretty good. One of the fastest-growing entrepreneurial companies in Canada wanted him to be its new Chief Operating Officer. Discussions had moved quickly with the celebrity founder himself making the case that the firm’s over-burdened systems and processes desperately needed the executive’s world-class operational experience. Topping it off, the word ‘successor’ was whispered at the close of one late night discussion. After some heart-wrenching deliberation, the executive decided there would never be a better opportunity to catapult his career. He accepted the company’s offer and resigned from his employer of twenty-three years………Six months later he was unemployed, richer only by the knowledge that his impeccable credentials had in fact been glaringly lacking of the only experience and skills that truly mattered.

Professional managers are typically hired into entrepreneur-led firms with two sets of challenges, though only one is openly discussed during the courtship process. There are the business and function-related challenges for which the individual is being hired, most commonly some variation of professionalizing, driving, stabilizing and/or bringing specialist management experience to the business. And then there are the less clearly defined challenges of fitting into a company defined and dominated by a single individual, the entrepreneur. For the uninitiated, this is the proverbial rabbit’s hole where wonder and sometimes madness await.

As a breed, entrepreneurs are a unique lot. The word itself derives from the French word enterprise, which was used in the 12th and 13th centuries in reference to actions of war. The word entreprendre meant to “attack a person or a castle for pillage or to take prisoners for ransom”. Though time softened the term’s marauding sharp edges, the entrepreneur has always been associated with risky behavior and a rule-breaking ethos, one untethered to the customs and norms held by the dominant society. The distinction between deviating from the norm and deviance is at times lost on some entrepreneurs.

Modern day entrepreneurs are noted much more for their laudable ends than the means by which they secure them. Images of scoundrels have given way to paragons of innovation, and economic benefit. Entrepreneurs are now coveted by all levels of government and policy makers who fuss to attract, fund, and incubate them. Corporations seek to inject their spirit into their cultural blood streams while schools try to create them through all manner of innovation and entrepreneurship curriculum. But image makeovers notwithstanding, prototypical entrepreneurs remain rebels, contrarian outsiders who because of circumstance, circuitry, or destiny see opportunities where others do not, and challenge the convention. And their sine qua non is obsessive passion, hard work, unconventional thinking, salesmanship, ambition and a never-say-die drive. Working for such individuals must, however benignly, differ from the experience of working within more traditional corporate walls.

Over the next few posts we look at several entrepreneur prototypes and their implications for executive success, and failure

About The Author

Robert Hebert, Ph.D., is the Managing Partner of Toronto-based StoneWood Group Inc, a leading executive search firm. He has spent the past 25 years assisting firms in the technology sector address their senior recruiting, assessment and leadership development requirements.

Dr. Hebert holds a Masters Degree in Industrial Relations as well as a Doctorate in Adult Education, both from the University of Toronto.