1. Not correcting problem hires fast enough.
First time founders are often too hesitant to give negative feedback, demote a too-technical manager who should have stayed an IC, or remove a problem employee who isn’t working out.
The anecdote that comes to mind is a local startup that hired a C-level executive’s UI designer friend into their VP of Product role. He was wholly incapable of doing the job but they kept him in the job for 2 years to “give him a chance to grow into it.” Everyone below VP level openly talked about how the VP of Product was incompetent and how to work around him.
The company’s product initiatives ultimately failed to even get started and they had to pivot to entirely services based work. Do not stay at a startup that insists on keeping unqualified people in leadership positions long after everyone in the company has given up on them.
2. Firing the wrong people
The same startup was forced to downsize, largely because their product plans failed to even become defined enough to start under the incompetent VP of Product.
It was the perfect opportunity to fire the VP of Product and his sprawling empire of people who did very little, but they avoided that due to his connections to a C-level executive. Instead, they started cutting engineers. They focused on cutting engineers with the highest compensation out of a misguided effort to cut as few people as possible.
In the process, they lost their key engineers who were holding things together. They sent a message to everyone that incompetence is tolerated if you know the right people. And they lost even more core engineers who quit in the months after those layoffs.
Everyone makes hiring mistakes. It’s how you respond to those hiring mistakes that will seal the fate of the company.