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Lenny Rachitsky: observation

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)

“Your job is to help them see how massive an opportunity this is and not just give you what you want, but just like, wow, okay, here's the way to unblock this thing.”

— Lenny Rachitsky

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Speaker
Lenny Rachitsky
Attribution
Verified speaker
Claim type
observation
Recorded
22 Mar 2026
Publisher
Lenny's Podcast

Transcript context

…Yeah. We should have a stamp, like influenced, at the end. So I think one of the things that people misunderstand is the constraints that they are bound by versus their leadership. Execs are not ... They don't have the same boundaries of budget and headcount and timeline that you feel. They can move people around in the organization. They can ask for more resourcing. They can get creative. They can elevate projects, kill projects. And so you have to come to them with that mindset of, "Hey, with today's resourcing, with this many engineers or this kind of tooling or this kind of investment, here's what I can get. But I'm thinking of the 10X case. I'm thinking of the accelerated case. And if that's what you want, and if that's aligned with your incentives, here's what I need to be successful." And so I think that people think, "Okay, well, I've got my pizza team and I've got my four engineers and what you're asking is not possible." Well, if it's not possible, tell them why not. Come back and say, "The thing that you're asking for, I'm super stoked about that. I need eight more people. I need you twice a week for an hour. I need much closer alignment with our marketing team, and I'm not sure how to get that." You have to think about what are the constraints that hold you back that they can actually help you a lot with. And people miss out on this all the time, of not asking for what they need to be successful, especially when the ask from the executive seems unreasonable. This is such a good piece of advice. Just if you get them excited enough, things can significantly change in terms of resources and prioritization. Your job is to help them see how massive an opportunity this is and not just give you what you want, but just like, wow, okay, here's the way to unblock this thing. Here's how we can go like, okay, this is going to be our new big bet. Let's go big here. Yeah, absolutely. This is going to be our new big bet. And this comes back to aligning with what the company's trying to accomplish and also the urgency. So some things, if you added a dozen more people or perfect alignment with go to-market, yeah, you could get them to market faster. But is that the most important thing for the company goals? Is right now the answer? Is accelerating this in this way actually going to do more? Or is it something else that's actually more aligned? And so I think it's still being so rooted in the company goals and what the exec is trying to accomplish and what your users really need to be successful so that you can say, "In order to accelerate our goals, here's what we can do."…

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