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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)

“You need to go work somewhere else. But if you respect them, if you think they have something to offer you, that they got to the place that they're at because they learned and they developed a skill that you're trying to gain, awesome.”

— Jessica Fain

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Everything needed to verify it.

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

Transcript context

…Also former podcast guest. Also former podcast guest, former CPO at Calendly and Glassdoor and now at Microsoft, and Annie's just the best. She always said to me, "It's not my fault, but it is my problem." And I think that that's the vantage point that a product leader has to have, especially if they're trying to put themselves in the shoes of an executive. As product managers, one of our best sets of skills is curiosity, and empathy, and trying to understand our users. But the moment that we're talking to an executive or to a stakeholder, we forget those skills and those talents, and we begin to think about our ideas, getting that approval, getting to the next meeting, whatever it might be, the incentive that we are driving. We don't think about the curiosity and empathy for what they're thinking about, for what their incentives are, for how their day has been. And, if we can take some of those skills of building great products and think about our executive as our key user here, then we can have a much, much more productive conversation. I think one of the most disastrous things you can do is going into a meeting just looking for approval for your plan. Instead, if what you go in with is, how can I learn? How can I strengthen this plan? How can I use the domain expertise, the context, the experience that this person brings to the table, and imbue that into my product work? Both the executive will like you better, because they will feel like you have actually built product alongside them. But, you will also end up with a better product. I often hear people say to me, "Oh, they just don't get it. They don't see what I see. They're not in my meetings. They don't know how hard this is." Fine. If you don't respect that person, if you don't believe they know something you don't, you need to quit. You need to go work somewhere else. But if you respect them, if you think they have something to offer you, that they got to the place that they're at because they learned and they developed a skill that you're trying to gain, awesome. Take the feedback, take the insight, ask questions, and don't just treat it like a rubber stamp, because that's a failure state, and it's a failure state that they don't like. I want to dive deeper into this stuff, but first, something on my mind is some people might be turned off by this topic in terms of, it may feel icky of just like, "Oh, I don't want to try to be this manipulative person, and deal with politics and influence. I just want to do awesome work. Why do I have to do this?" Speak to that person that's kind of just feels icky about building this and working on this and being this person.…

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