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The Biggest Problem Remote Working Startups Need to Solve

The Biggest Problem Remote Working Startups Need to Solve
By Vin Narayanan
Date February 15, 2022

Remote work isn’t going away. Workers want it — even if the companies that employ them don’t. And because companies are competing hard for top talent, they have to offer some flexible working options. 

That doesn’t change the fact that it’s HARD to collaborate remotely. It’s one of the biggest pain points of every remote working environment. It’s why many companies (and workers) are moving to a “hybrid” work model where workers come into the office part time and work from home part time.

The idea is that workers can collaborate on their “in office” days and do their other work remotely. That sounds nice in theory. But it has one major problem: the best and most innovative solutions are a result of serendipity.

Merriam-Webster defines serendipity as “the faculty or phenomenon of finding valuable or agreeable things not sought for” (emphasis mine).

In remote work environments, almost every bit of information is “sought.” People ask others for meetings. They seek specific answers or bits of information in Slack or other messaging platforms. They email others for thoughts and opinions. Very few interactions are “unstructured.”

Yet unstructured or unexpected interactions are a critical part of the working process. You can’t schedule genius — or strokes of luck.

I spoke with a founder recently about her journey. It involved her having chance encounters at meetups and walking up and down hallways to find other people who might be able to help. Those moments of serendipity that put her on a path to success are extremely difficult to replicate in remote environments.

Bouncing ideas off other people in the moment, overhearing conversations that spark a thought or just being able to talk through something without scheduling a call or working around someone’s “focus” time are all important parts of the work process that the current crop of remote working tools just can’t handle.

So as I evaluate the next crop of remote working startups, I’m not interested in the next great email or calendar product (though I’ll use them!). I want to know which startups will bring serendipity to remote work. That’s the biggest problem that needs solving. And I believe the startups that “solve” serendipity will be the next Zoom or Slack for startup investors.

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