I was on the board of a company that had a milestone to hire a vice president of sales by a certain date. We even had a budget to engage a recruiter to help us find the right candidate. Long story, short, we narrowed the selection to two candidates. The selection committee from the board, including the investors who had set the milestone, met with the candidates individually, and we endorsed the CEO’s recommendation.
Milestone met. Next round of funding closed. All is good… NOT!
To this day, it is my opinion that this specific decision led to the company’s ultimate failure (and the loss of over $5 million of investor money).