It hurts to ask
“It never hurts to ask!”
I get this advice a lot. It’s bullshit and we all know it.
We hate getting asked for things we don’t want to give. It’s painful at a visceral level to have to say no. We generate narratives about the asker to justify the “no” we have to deliver that range from “they are CRAZY to ask me for this” to “what a snake to ask for something so out of bounds”.
It doesn’t matter that they were “just asking” and that we’re free to push back or say no - the emotional damage of the ask is done when the ask is made. Just recently, I’ve seen an investor get bad feedback on a close friend of mine because of two “asks” he made in previous compensation negotiations. I can’t think of a worse reason to harbor bad feelings against a startup executive, but I’m not surprised. Because it hurts to ask.
Beyond the personal toll asks take, each ask has an outsized effect on slowing...
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