Feedback Void

There is a certain allure to someone who marches to the beat of their own drum. Framed negatively, it’s stubbornness or a refusal to heed the warning of others; positively, it’s harboring deep conviction and blazing a trail to prove naysayers wrong. Silicon Valley’s version comes in the form of “outside the box” founders, while modern finance offers hedge fund managers who use malapropisms to divine life’s purposes.

Certainly, when starting out, inventing mental models deviating from the norm almost necessitates betting against conventional wisdom. Founders often construct elaborate founding stories that emphasize how they flowed against the grain, discovered a niche others missed, and wedged it successfully into the business they now employ. The criticism would be that this level of stubborn belief and conviction is a boon during the 0-to-1 phase of development, but eventually evolves into a burden with product maturity; the attributes that make founders successful usually don’t apply to later-stage managers.

But at the same time, with success comes fame and fortune, and the rich and powerful often end up attracting enablers and hangers-on, replacing the vocal doubters and objections at the start of the journey. It builds a bubble for the purveyor of said ideas, where the dearth of critical feedback eventually festers into tragic blind spots.

The power dynamics and our shared social/political/economic hierarchies make this the default outcome. CEOs usually don’t get honest opinions from their employees, and sometimes not even from their board of directors either. Powerful political figures have layers of bureaucracy that can moderate anything too critical, even as lobbyists flatter to further influence. Celebrities have their friend cliques as well as feed off of one-sided, parasocial relationships with their fans.

Extremely Hardcore is a recent book that chronicles the past ~2 years of Elon Musk’s purchase and privatization of Twitter. The stories that the author gathers from former employees, investors, and other journalists paint a picture of someone who prides himself in contrarianism—identifying those who would categorize as his “enemies” and mechanically take the opposing stance—while those around him cheered on and validated his instincts. The result has been a series of misguided initiatives to “fix” the platform, usually failing to achieve their stated impacts, all the while punishing dissent1.

It takes some humility and foresight to recognize this trap and avoid falling in. A piece of advice I’ve received from a couple of CEOs and CTOs: intentionally hire people who think differently and come with complementary skillsets, and work really hard to listen to their feedback2. This segues with the recent management philosophy around creating safe spaces, but the value goes beyond team satisfaction; the critical feedback garnered from disparate perspectives is precisely the hedge needed to keep boneheaded ideas from traveling too far.


  1. Usually by unceremoniously firing the messengers.

  2. Whether you take action on that feedback is another thing altogether; there’s an art to receiving feedback as well as giving it.

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