Evidence receipt / evaluation
Published · transcript-backedJessica 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 one thing that really trips people up is execs are so good at seeming certain. They say things in an authoritative way with confidence, with surety, because so much of their work is having to make those ultra-fast decisions with little information.”
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- Speaker
- Jessica Fain
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- Claim type
- evaluation
- Recorded
- 22 Mar 2026
- Publisher
- Lenny's Podcast
Transcript context
…The fact that, just the fact that I have so many of these people on the podcast, what a sign of an incredible team. Okay. So yeah, so most people do not work for a Stewart that has incredible product sense, really cares about craft. And most people are like, "He or she is so wrong about what we're doing, this is such a mistake. They don't listen, they don't know what they're talking about." How do you deal with that? One assumption I have of how folks may misunderstand this skill is that they have to be a yes man. They have to take everything that the leader said and do exactly that. That is absolutely wrong. You get paid to have an opinion, you get paid to be a domain expert. And in a lot of ways, your executive is looking for you to be the deepest person in the room, especially if they're good at their job, right? They're looking for you to be the expert. And so, bringing your expertise to bear is absolutely crucial. Elon Frank, who was my boss at Slack as well, is now CPO of Checker, he always had a customer anecdote in his back pocket. I can hear him in my head saying, "I was just on site last week with so-and-so and they said blah, blah, blah." He always brought his expertise to bear, and many of the executives at Slack were not from a strong enterprise background, so he could bring that to the forefront. I think that has to be married again with that curiosity and empathy. If you hear something that you don't agree with, this is something that a guy my team does super, super well right now. He'll hear something that flies in the face of the data he's seeing, the insights he's gotten, his experience in his domain expertise, and he'll say, "That's so interesting. What led you to believe that?" That kind of question is actually curious, about this person said something that I think is dumb, but there must be something behind it. And so if I actually care what's behind it, and what you end up doing in that question is co-creating with the person who offered the opinion in the first place. You're able to say to them, "I'm interested in what led you to that belief, your experience. Did you have a meeting last week? Are you getting pressure from the board right now in a certain way? What is leading you to that belief? " I think one thing that really trips people up is execs are so good at seeming certain. They say things in an authoritative way with confidence, with surety, because so much of their work is having to make those ultra-fast decisions with little information. But if this is someone who is also a learner, who also has a growth mindset, then if you are able to help them unpack why they believe something and then respond with your own domain expertise, you are able to get to a better solution together. I love these very tactical phrases and tips for how to deal with someone, say a leader. Let's just say this is like they're a director of product, VP of product, CEO that you're trying to convince to agree to plan. So the phrase you're suggesting here is, "That's so interesting. What led you to believe that?" Anything else along these lines, say you're pitching a product or an idea to say a VP of product and they're just like, "Hmm. What else works?"…
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