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Jessica Fain: evaluation

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)

“" I think that execs are moving so quickly that they won't always give you that context of urgency and so you have to ask for it.”

— Jessica Fain

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

Transcript context

…And obviously, everyone's so busy. There's already so much work on their plates. You can't just hop on it. Everything an exec says. There's also this classic advice of sometimes execs just say something and everyone takes it so seriously. "Oh, I have to do that." And sometimes they're just saying it in passing. So it's a balance of take the opportunities, don't [inaudible 00:42:13] single thing. Yeah. And a great question to ask in that scenario is how strongly do you feel about this? So if you hear something that they say really strongly, or how urgent do you think that is? Or, "Hey, here's what the team is working on now. Do you think that that trumps these priorities?" And if they say," Yes, listen, do the thing that they say trumps it. "It's not about jumping on every request or taking every piece of feedback, it's about contextualizing it and why they believe that, what they think the urgency is, and then actually responding to that. So more often than not, they'll say," I wonder if we could do this kind of study. "And people will go and say, "Oh my gosh, we have to go run that study right now. We have to deprioritize everything else." But if you say to them, "Hey, that's a really cool idea. I like that. Do you think that that's more important than these three other studies or three other projects that we're working on now?" And they'll say, "Oh no, no, no. That's a random idea. Put it on the backlog. " I think that execs are moving so quickly that they won't always give you that context of urgency and so you have to ask for it. This is something I've been working on getting better at as a leader. This is just an idea, this is a mandate, this is something I want to see, but it's hard. Sometimes it's hard to remember to do that because your brain is spinning with ideas. This comes back to your point about getting into the mind of the person in the meeting, the leader. They're running around all day. I think you call it a strobe. You're just like, bam, another meeting next meeting, next meeting, next meeting without a lot of context and they just say things, and sometimes it's important to them, sometimes not, which comes back to one of your tips at the beginning of this chat is spend 30 to 60 seconds at the beginning just giving them a little context on what the heck. What would you recommend in that 30, 60 seconds? What are some key bullet points of what you want to communicate?…

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