The Best Advice I've Ever Received

“Advice is one person’s experience generalized”, an entrepreneur told me once. “It’s a single point of view with all kinds of survivorship and attribution bias. Advice can be a terribly dangerous thing, because it can be used as a shortcut for thinking.”

When I asked how he responded to requests for advice, because as a successful entrepreneur he was often solicited for it, he replied that he first shared the structure and the framework he used to look at the problem. Only after discussing that, did he reveal the details about he and his team had arrived at a decision.

Each time someone asks for advice, I remember that conversation and the wisdom that entrepreneur shared with me. And I wonder whether what I’m about to say is as helpful as the little piece of paper tucked into a fortune cookie, an out-of-context recommendation, that can be easily misinterpreted.

When I reflect on the best advice I’ve received in my life, it has never been the counsel that provided an immediate point-of-view on an answer. Rather, it was the guidance that started as a single probing question that I couldn’t answer immediately, a question that invited me to look upon the puzzle with a new perspective and demanded deeper thought. A little Buddhist Koan.

I suppose that’s why I gravitate to frameworks and data when I write. Both are starting points for a series of questions about what is similar and unique in different cases; what applies and what doesn’t. This process of comparing and contrasting, of testing and defeating assumptions, that’s what leads to insight. By accepting advice at face value, we simply copy someone else’s answer, which is just as valuable as following the recommendation of a fortune cookie.

When someone next asks you for advice, I challenge you to take a moment and think about the right question to ask or the right framework to frame the problem, rather than the best recommendation to make. It might be the best advice you’ve ever given.

Published 2014-07-25 in Startups  Best Practices 


I am partner at Redpoint. I write daily, data-driven blog posts about key questions facing startups. I co-authored the book, Winning with Data. Join more than 20,000 others receiving these blog posts by email.

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