The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack)

**Jessica Fain** (0:00)
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, we forget those skills and those talents.

**Lenny Rachitsky** (0:11)
It's your fault if the leaders didn't buy into your idea.

**Jessica Fain** (0:14)
People completely misunderstand how executives make decisions, what is going on in the heads. I describe an executive's calendar as a strobe light going off. You wake up at 8 a.m., you've already got a huge list of urgent things going on. They have not had the time, the energy, the wherewithal to center your problems.

**Lenny Rachitsky** (0:34)
What are their goals? What are they trying to do? How are they measured? Connect the thing you're pitching them with that success.

**Jessica Fain** (0:39)
There's ways for us to ask much more interesting questions of our executives. Tell me what the board is pushing you on. Execs want to be successful too. They want to be good at their jobs.

**Lenny Rachitsky** (0:50)
Sometimes you have the best idea and they just don't buy.

**Jessica Fain** (0:52)
One of the biggest things you can do to build trust is kill things, deprioritize things. If you're thinking about how do you be more senior, how do you show up in a way that is in a leadership mindset, you get paid to be a domain expert. Your executive is looking for you to be the deepest person in the room. Bringing your expertise to bear is absolutely crucial. You have to act like a CPO.

**Lenny Rachitsky** (1:17)
Today my guest is Jessica Fain, who's been a product leader at Box and Slack and Brightwheel and now at Webflow. And she has gotten very, very uniquely good at the art and science of influence, and in particular influencing executives. Influence might be the single highest leverage skill for product leaders outside of AI. We actually get into how AI is changing the skill of influence. I've never heard a podcast conversation get deep into the art and science of influence, how to actually change people's minds, and the mistakes that people make when they're trying to influence leaders. We get very tactical and very specific. There's a bunch of stuff in this conversation that I've never heard before or thought about. I am very excited for you to learn from Jessica. Before we get into it, don't forget to check out lennysproductpass.com for an incredible set of deals available exclusively to Lenny's newsletter subscribers. Now let's get into it after a short word from our wonderful sponsors. This episode is brought to you by Omni. Many product teams today are in the process of debating how to ship AI analytics. The hard part is obvious. Having an LLM guest at SQL in production is a huge mess and just a bad idea. Omni takes a different approach. They have a semantic layer built in so that when you embed their analytics, the AI actually knows your business definitions, not just your raw tables. You can test queries, validate the reasoning, and lock down permissions before anything hits production. If you want AI analytics in your product without building the whole stack from scratch, check out omni.co.uk-lennys for a free three-week trial. Companies like Perplexity, DBT, and BuzzFeed use Omni to ship analytics their customers can trust. That's omni.co.uk-lennys. This episode is brought to you by Lovable. Not only are they the fastest growing company in history, I use it regularly and I could not recommend it more highly. If you've ever had an idea for an app but didn't know where to start, Lovable is for you. Lovable lets you build working apps and websites by simply chatting with AI. Then you can customize it, add automations, and deploy it to a live domain. It's perfect for marketers spitting up tools, product managers prototyping new ideas, and founders launching their next business. Unlike NoCo tools, Lovable isn't about static pages. It builds full apps with real functionality, and it's fast. What used to take weeks, months, or years, you can now do over a weekend. So if you've been sitting on an idea, now is the time to bring it to life. Get started for free at lovable.dev. That's lovable.dev.
Jessica, thank you so much for being here. Welcome to the podcast.

**Jessica Fain** (4:00)
Thanks for having me.

**Lenny Rachitsky** (4:02)
It's my pleasure. Let's set this conversation up. We're going to be talking about the skill and the art of influence, and in particular, influencing executives and leaders, people above you that you want to convince to do things you want them to do. Help us understand why this is worth people's time. Why is this worth the next hour of someone listening to this? Why is this skill so important to people's careers?