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Josh KleinJosh Klein is a professional hacker who examines systems and helps people understand how to affect change within them. Speaking at conferences like TED and the World Economic Forum’s annual meeting in Davos, and to companies such as Microsoft and Oracle, he recently teamed up with Bill Jensen, President/CEO of The Jensen Group to write the new book, “Hacking Work“.

Called one of the top breakthrough ideas for 2010 by the Harvard Business Review, “hacking work” is all about working smarter by strategically working around bureaucratic processes. I caught up with Josh to talk about business innovation, key creative problem solving tactics, and his childhood negotiation with the tooth fairy.

Nancy Garcia: Tell me a little bit about when and why you became a hacker.

Josh Klein: Not sure how you determine this — it reminds me a lot of when my gay friends were coming out and we’d laugh about their parents trying to figure out when it had all happened. It’d just always been that way.

One thing that was a pretty good indicator, though, was when I was six or seven and I had an altercation with the tooth fairy. Apparently, I wrote a note explaining that I understood that good teeth were in high demand, but that unfortunately due to inflation the price had gone up from $0.25 to $1.00. I even provided a couple of my friends’ addresses so the tooth fairy could check the market rate.

I’m still not sure if I got a dollar or a quarter in the end (my folks refuse to tell me, stating that it cost them another night’s sleep trying to figure out), but the attitude sure stuck with me: Systems exist to be optimized, and that evolution can come from any of the participants within it.

NG: For a lot of folks, hacking brings with it negative connotations. You focus on the positive side. Has it been difficult for you to convince people that you are not evil?

JK: Most people get it once they understand that the term “hacking” comes from mechanical engineers, who would “hack” (maybe from “hacksaw”?) pieces of a car together in new and often unintended ways. For example, a glass-packed muffler was a lot less efficient in terms of mileage if you broke the glass, but it makes for a hell of a throaty growl when you’re cruising down the strip! Same with over boring your carburetor, or any one of thousands of other little things that optimize for whatever behavior you’re looking for.

That’s the same sort of creative problem solving and innovation that characterizes hacking today. With the arrival of the internet as we know it today we’re seeing an explosion of this kind of hacking, both for good and for evil, because people everywhere have access to more information than ever before. Getting mastery over any given system is just a matter of interest and talent, rather than access.

The result is like a hammer — you can kill someone with it, or you can build a house, but you wouldn’t call the former carpentry. Similarly, real hardcore hackers would rather demonstrate their chops for the benefit of everyone (white hat hacking) than just go about destroying things.

NG: Many industries, especially traditional media industries, are in the midst of changing their infrastructures to more directly address shifting media consumption habits. What are the most common mistakes you see companies/businesses make during these sorts of transition periods? What kind of advice can you offer to executives in the midst of this sort of restructuring who are perhaps adjusting their perspectives, taking into account today’s new media landscape?

JK: The biggest — and most common — mistake I see is traditional advertisers and corporations treating new, many-to-many media like traditional, one-to-many media. A Twitter account is not a billboard, and treating it as such will only earn you scorn.

This extends pretty deeply into the entire shift towards new means of media consumption. Increasingly we’re seeing consumers that want a one-to-one relationship with a brand, and those companies that provide it — be that through a hyper-personal Twitter account, superior customer service, or radically transparent leadership — garner serious fans. Conversely, companies that attempt to hide corporate issues, obfuscate access to information of interest to customers, or deny responsibility for mistakes can get bitten pretty hard when the public decides to call bullshit.

A lot of this has to do with the empowerment of the consumer, but it’s being met in the middle by the inability of large bureaucracies to innovate or respond fast enough to market shifts.

NG: What are the top five hacking tactics you use regularly or that have made the most impact on you/your career?

JK: My top 5 hacking tactics (at the moment):

  1. Make it normal. By getting comfortable enough with a system that its inhabitants accept you into it you can more readily exploit it.
  2. What’s “obvious”? Understanding people’s expectations of a system is almost always a great way to find vectors to tweak to produce unexpected results.
  3. Learn the basics. Presentation skills, good writing, and being able to work well with others are universal capabilities you’ll need to be successful in *any* tautology. Having those things down makes infiltrating other arenas a thousand times easier.
  4. Do your homework. Google someone before you meet with them; read their tweets, scan their Facebook page, and see if there’s any press you can mention in your meeting. Knowing what they’re interested in – and proud of – goes a long way in making for a productive conversation. This goes for companies, too!
  5. Think different. This sounds easy, but it isn’t. Human beings are social creatures who have been successful because of their ability to absorb and act within social norms. Hacking a system means understanding these norms well enough to be able to act, but resisting them enough to see outside them. Practice flipping things on their head – take what’s good and describe it as bad, and vice versa, or take issues of largeness and describe them as being small. Inverting expectation is an easy way to examine a system in a new way and can lead to big insights.

Nancy Garcia is digital strategist for Piehead.

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