Article Highlights

  • Many tech startups face similar challenges, e.g. hiring, product fit, growth, retention, etc.

  • There is a temptation to solve problems in a vacuum and "go it alone."

  • While learning from first principles is unequivocally important, leaders often benefit more from building a habit of interviewing at least one expert per week to improve their thinking on their #1 challenge.

Where I'm coming from

I've noticed a trend. Having been an advisor to high-growth startups for 4-5 years now, one thing stands out: most of the companies I work with are trying to solve very similar problems, but often do so in isolation. This allows me to add value by connecting people or sharing some best practices, but I challenge them: "Who else did you meet with to explore this topic?"

Ray Dalio's landmark book, Principles, offers some additional guidance in the form of two principles that leaders could benefit from:

Principle 3.2 Practice radical open-mindedness. a) Sincerely believe that you might not know the best possible path and recognize that your ability to deal well with "not knowing" is more important that whatever it is you do know.

Essentially, Ray Dalio is encouraging us to embrace intellectual humility. Start with what you know you don't know. If you're new to an industry or company, this list is likely to be quite long. That's okay. The most important part of all this is a sober appraisal of what is known vs. unknown.

Later, once you've done you're preliminary research and assembled some viewpoints, its time to spar, intellectually, with other people. Ray suggests seeking those with high "believability" which he defines as having done X with success 2-3 times and a cogent rationale to go with it:

Principle 3.4 Triangulate your view with believable people who are willing to disagree.

As he says it, "By questioning experts individually and encouraging them to have thoughtful disagreement with each other that I can listen to and ask questions about, I both raise my probability of being right and become much better educated."

With this in mind, leaders could benefit from building a habit of interviewing at least one expert per week to improve their thinking on their #1 challenge.

Here are a few practical services that can help you get out of your own head and absorb perspectives from other people with (potentially) high believability:

  • Meetup: a community-managed service that brings people together on a common interest. I've attended and spoken at numerous meetups from topics ranging from Ethereum to Leadership to Customer Success. All were worthwhile because I got to interrogate other folks with relevant experience (to learn), and have others challenge my beliefs (to iterate).

  • Shapr: a popular new service that's described as Tinder for professionals. Swipe for 1 minute per day and get matched with other professionals.

  • Quora: ask a question, hope for high-believability responses.