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Published · transcript-backed

Jessica Fain: recommendation

22 Mar 2026 Lenny's Podcast The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack)

“They are running around context switching in the most insane ways I've ever seen, and everything that comes across their plate is an emergency. So one of the biggest tactics I think is so important is, just take 30 seconds at the top of a meeting.”

— Jessica Fain

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Speaker
Jessica Fain
Attribution
Verified speaker
Claim type
recommendation
Recorded
22 Mar 2026
Publisher
Lenny's Podcast

Transcript context

…What's an example of that when you talk about, people don't understand how product leaders actually make decisions, how they decide what to do, what to listen to, what's an example? Oh my gosh. I think the biggest example of this is people don't understand executive calendars. A lot of times on Google Calendar, it's blocked. You can't see what they're working on, but I describe an executive's calendar as like a strobe light going off. You wake up at 8:00 AM, you've already got a huge list of urgent things going on. You go from a meeting with finance on a budget, to an interview for another executive, to a people problem, to a legal problem, to a product review. And the product manager coming to that product review, or the leader who's trying to make a pitch, thinks, "I've been prepping for this meeting for two weeks, three weeks, maybe six weeks since we last spoke," but the executive coming into that session hasn't thought about you since. They may not have gone to the bathroom today, right? And you have to understand that they have not had the time, the energy, the wherewithal to center your problems and you have to help them get into that mindset. So this is as simple as, execs are people too, right? They are running around context switching in the most insane ways I've ever seen, and everything that comes across their plate is an emergency. So one of the biggest tactics I think is so important is, just take 30 seconds at the top of a meeting. Why are we here? What happened the last time we talked? Why is this important to you? Why is this meaningful? And really remember that they are not thinking just about you. They are optimizing for a global maximum and not for the local that you're optimizing for. Essentially, this is how to help someone in this world that is running around from meeting to meeting without context on most things, maybe hasn't have time to go to the bathroom. How do we help them see what you want them to see, and maybe buy into your vision and suggestions?…

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