De Milliano: Bad executive hires drive star employee attrition by destroying trust
Eeke de Milliano · What makes (or breaks) executive hires | A deep dive with Eeke de Milliano (Stripe) · Mar 6, 2025 · at 8:57
Eeke de Milliano, Global Head of Product at Stripe, explains why leadership hiring carries much higher organizational stakes than hiring individual contributors.
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“Reason number one why it's bad, but like reason number two why it's bad is because everyone looks at that bad hire or that bad fit, basically. Again, like, I don't think they're generally bad people, but like that person who isn't a good fit, and they look at the leader who hired that person, either the founder or the exec, and they now all of a sudden don't trust that exec or that founder's judgment. In the end, judgment is almost like the most important value you have as a founder or as a leader, and that gets really bad, and that's when your, you know, star employees start quitting because All of a sudden they kind of feel like, hey, I actually, I'm not sure I trust this person's judgment anymore.”
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