The best young founders know they need mentors.

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Chip Conley’s experience at Airbnb seems to be turning out so well, it could almost make you Millenials wish you were sage 52-year olds.  Well…maybe not.  But it certainly makes this older Baby Boomer want to have more of Conley’s experiences working with you “youngsters” – my word, not his.  It sounds like great fun.

This is a story of the multi-generational work experience we’ve all dreamed of – people of varying ages enjoying each other’s company while appreciating and learning from each other’s strengths.   My guess is that much of the success of the Airbnb story is a direct result of Conley’s egoless attitude and his open-minded approach.  But, kudos also to the Millenials who had the wisdom to value his.

Conley’s article provides insight for anyone, really, going into a work situation charged with a specific task, but especially for an older outsider going into a younger, established culture.  Conley tells us, “I was ‘an old-school’ hotel guy and had never used Airbnb. I didn’t even have the Uber app on my phone. I was 52 years old, I’d never worked in a tech company, I didn’t code, I was twice the age of the average Airbnb employee, and, after running my own company for well over two decades, I’d be reporting to a smart guy 21 years my junior.”

But he took the job of “Head of Global Hospitality and Strategy” anyway and was charged with “helping turn their growing tech startup into an international giant.” (Think he’s succeeding?)

Here’s some of his 50-something wisdom, and the article has plenty more:

  • “First, I quickly learned that I needed to strategically forget part of my historical work identity. The company didn’t need two CEOs, or me pontificating wisdom from the elder’s pulpit.
  • “The second thing I learned…can be summarized in a one-line trade agreement: ‘I’ll offer you some emotional intelligence for your digital intelligence.’
  • “I also learned that my best tactic was to reconceive my bewilderment as curiosity, and give free rein to it. I asked a lot of ‘why’ and ‘what if questions, forsaking the ‘what’ and ‘how’ questions on which most senior leaders focus.”

Chip Conley’s a smart man.  Who says you can’t teach an old dog new tricks?

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