Win an Oscar or be CEO of Etsy?

Last week at the Collaborative Gain Council meetings in New York, I interviewed Chad Dickerson (on the right with me before we go on stage), CEO of newly-public Etsy, and learned that his ‘secret to success’ seems to be the same as the Mexican filmmakers Inarritu, Del Toro, and Cuarón, two of whom recently won back-to-back Best Director Academy Awards.

Let me explain.

As part of my research before interviewing Chad, I reached out to Council members, industry friends, and my various networks to ask what questions people would like me to ask.

Irene Au, Councils alum, longtime friend, and now Operating Partner at Khosla Ventures, responded with a simple question for Chad.

She suggested I ask the following:

Chad is one of the nicest guys on the planet. He’s humble, smart, and has that Southern charm; he defies the stereotypical Internet startup CEO.  Ask him what he thinks is the secret to his success.

Once we were on stage, Chad and I had a long and fruitful discussion. At the end of our hourlong conversation, I asked Irene’s question.

Chad’s answer was simple – and went to the heart of why I started the Councils over a decade ago.

He said:

I ask for help.

Surprisingly few leaders are willing to ask for help – and to do so repeatedly. Chad is. And he believes it’s the secret to his success. That doesn’t surprise me. Asking for help is what I call an ‘ordinary superpower’ – that’s how I described it in my TEDx talk last year.

It’s also, as I mentioned, the reason I started the Councils in 2003 with Marissa Mayer and others: I wanted to create a community and context where Internet leaders could safely ask each other for help and listen to what their peers had to then say to them.

While many leaders are unwilling to ask for help and listen to the responses – most of the best are. The Los Angeles Times published a feature article earlier this year about the “Three Amigos” – i.e. the three Mexican filmmakers and longtime friends, two of whom remarkably won Best Director Oscars in 2014 and 2015 for Gravity andBirdman, respectively.

It turns out the secret to their outsized success: they ask each other for help continuously.

Alfonso Cuarón, whose film Gravity won the 2014 Oscar for Best Director, described to the Los Angeles Times how much he asks his two friends for help when creating and directing a film:

There’s no film that I do that doesn’t go through their eyes and their hands.

The article went on to explain their process in greater detail:

They’ve all been mentioned in various credits on one another’s films, but more often than not the work they do for each other is a labor of love. ‘It’s not about ego or yourself,’ says Inarritu from a recent shoot in Alberta, Canada, for his forthcoming film, ‘The Revenant.’ ‘It’s about how to make the film better.’

In my years of building the Councils and repeatedly urging thousands of Internet leaders to ask for help from their peers, colleagues, and customers, I can say that one of the main obstacles most leaders have to this very simple and powerful activity is ego. Like Inarritu suggests above – ego can get in the way of asking for help (and of then listening to the responses).

Many people seem to think that asking for help is a sign of weakness, rather than as Inarritu says, “to make the film better.” Many executives seem to fear that asking for help says something negative about them personally or about the quality of the work they do. Paradoxically, it’s quite the opposite. In fact, it’s how Inarritu did such a good job that he won Best Picture, Best Director, Original Screenplay, and Cinematography at this year’s Academy Awards.

I wrote about asking for help from customers in my co-authored book, Customers Included. I plan to write more about asking for help from peers and employees in the future, so let me ask you:

Do you ask for help? In this regard, are you like Chad Dickerson and these three great Mexican filmmakers? How about your company culture? Does your company support its employees to ask for help? Or do you – or your company – see it as a sign of weakness?

I’d love to hear your stories.

– Phil Terry


1. Conversation between Chad Dickerson and Phil Terry, Wednesday, April 22, 2015
2. Ali, Lorraine. “Reel Amigos.” Los Angeles Times, February 21, 2015. A1. Print.

About the Author

Phyl Terry

Phyl Terry, Founder and CEO of Collaborative Gain, Inc., launched the company’s flagship leadership program – The Councils – in 2002 with a fellow group of Internet pioneers from Amazon, Google, and others. Thousands of leaders from the Internet world have come together in the last 15 years to learn the art of asking for help and to support each other to build better, more customer-centric products, services, and companies.

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