How to determine if you should work to help a struggling employee

As an entrepreneur, you operate with the conviction that you can change the world. So it can be tough to accept that even as you aspire to solve the housing crisis, create ethical AI, or democratize space exploration, the one thing you will never change is another person.

When I first began to scale my startup, I recalled a common mantra, popularized by Lars Dalgaard, a board member at Andreesen Horowitz:

“In the world of startups, it’s important to make a quick decision, and fire fast…It’s one of those rare instances where appealing to the ‘angels of our better nature’ might in fact be the very thing that kills your company.”

But when it comes to implementation, I quickly learned “fire fast” is not as easy as it sounds.

Should I continue investing in a struggling employee? Am I holding them back by overcoaching and forcing a fit?


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