Jessica Fain's best product ideas kept dying, and she couldn't figure out why. So at eight and a half months pregnant, she pitched @SlackHQ's CPO @aunder on becoming her Chief of Staff. She wanted to see how executive decisions actually get made from the inside.
What she learned changed everything she knew about influencing execs.
People don't realize that an executive's calendar is like a strobe light going off. Budget meeting, a people problem, a legal issue—then your product review. You've been prepping for three weeks. They haven't thought about you since the last meeting. They may not have gone to the bathroom today.
And most people walk into that meeting chasing a quick yes.
Instead, she learned to treat execs like she treats her users—with the same curiosity and empathy.
Jessica has since led product teams at @SlackHQ, @Box, @brightwheel, and now @Webflow.
In our very tactical conversation, she shares:
🔸 The 60-second meeting opener most PMs skip
🔸 Why "that's so interesting, what led you to believe that?" can help you disarm an exec
🔸 How to align your pitch with what your exec is actually scared about
🔸 "Stewart plus two more"—her playbook for responding to a CEO's feedback
🔸 Why killing your own project is the ultimate trust-building move
Listen nyoutu.be/RP4vJeIb7WUiOEige