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Here's What Happened When An Employee Told Steve Jobs Something Couldn't Be Done

Lisa Eadicicco
Steve Jobs Apple CEO Founder Portrait Illustration

Mike Nudelman/Business Insider An illustration of Steve Jobs. Apple cofounder and former CEO Steve Jobs' reputation preceded him in many ways. Many have attributed Apple's success at least in part to Jobs' obsession with detail and perfection.

So you can imagine he wouldn't settle for being told that something could not be done. One former Apple and NeXT employee told Business Insider what it was like to face Jobs and tell him one of his assignments was impossible.

Ken Rosen, a managing partner at the consulting agency Performance Works, had the chance to work with Jobs at NeXT during the late 1980s and early '90s. Although Rosen worked at both Apple and NeXT, he only directly worked with Jobs during his tenure at the latter company.

Rosen, an emerging markets manager for NeXT at the time, took on the task of working with Jobs on a keynote presentation for a new product. 

It was during that time Rosen learned one of the most valuable management lessons of his career, Rosen told Business Insider.

Jobs told Rosen he wanted five specific things in the keynote. 

"I no longer remember what, but I just remember there were five things he wanted to show in the demo," Rosen said. "And we worked for a couple of days, and at the end of those days we realized we could do all but one."

Rosen had no choice but to tell Jobs that only four out of the five tasks could be accomplished in time for the keynote.

"I really tried to have a relationship with Steve where I didn't sandbag," Rosen said. "I would never want to tell him something couldn't be done if it in fact could be done."

Here's how Jobs reacted:

"He put his hand on my shoulder in this very fatherly to the point of patronizing way," Rosen said. "And he said, 'We need to do that one, too,' and just walked away."

Rosen said he felt annoyed at first after hearing Jobs' reaction. He wanted Jobs to trust his judgment and believe his team tried its hardest to finish the task at hand. But, of course, he went back to his partner at the time and continued working on the problem.

"The bottom line is we figured out how to do it," Rosen said. "And for Steve it was just another day at the office ... But I think there was something to that even for me. [The idea] that you can do something you don't think you can do, but you've got to find a way, is a useful way to look at challenges."

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