There’s a great TED Talk by Simon Sinek about how great leaders inspire companies by asking "why?" I think it also goes a long way toward explaining why big companies don’t handle change well. It’s not that they can’t ask "why?", it’s that the answer doesn’t make sense at their scale, though it should. Times change and big companies don’t like to change with the times.
At the opposite end from big industrial companies sit startups, nearly every one of which begins with an effortless expression of "why?" Big companies ask "what?" then "how?" but almost never "why?" according to Sinek, who I think has it absolutely right. But good startups are motivated from birth by "why?" Nearly every good startup begins with "why?" and that"why?" is traditionally quite simple — because the founders want one for themselves. A hardware device or software application doesn’t exist and they’d really like one, so they invent it. For startups "why" is easy. If it isn’t easy then you probably don’t have a good startup. If as a founder your answer to "why?" is “to get rich” you are in the wrong job. Applied to a more mature company, looking at Apple we can see the why of the iPod and iTunes was “to take your entire music collection with you wherever you go.” That sort of thinking isn’t common in big companies. Some of this is due to scale, some due to arrogance, and some to simply losing their way. But no matter how big a company grows, asking "why?" is still vital for continued success. They just don’t know it.
Back in 1986 Adobe launched Illustrator, Adobe’s first consumer product. The "why?" for Illustrator was “because (Adobe founder) John Warnock wants a drawing program,” which is a classic startup reason. The business plan had the new consumer division with a net-net positive cash position of $87,000 after five years. Millions invested creating an entire new business for a new set of customers through a completely new distribution channel for a lousy $87,000? Most companies would never have done it. Yet if you look at Adobe’s market cap of $13 billion today probably 90% of that is based on consumer and professional software that began with Illustrator. That $87,000 grew to $13 billion over 25 years.
Adobe was lucky to have a curious founder still at the helm. It was lucky to be making enough money to risk a few million on an alternate future, too. But 2011 is nothing like 1986. Looking five years ahead for business justification isn’t done any more because five quarters is a long time in business today. But then the average CEO tenure is also four years, so what? And that’s why big successful companies roll over and die.

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