Lessons from Jessica Fain (Webflow, ex-Slack) on Lenny’s Podcast
Jessica argues that the main skill that separates great product people from good ones is the ability to influence people and to get buy-in from your executives.
Here are my main take aways from the episode:
Influence vs Politics
Jessica points out that influence isn’t about playing silly politics. The main distinction is that politics is about manipulating outcomes for personal gain whereas influence is about taking people along the ride.
Influence is about increasing the odds that your good ideas survive and that your stakeholders understand why you are pushing for something specific.
Take away: Treat your executive as a key user. Approach stakeholder conversations like discovery interviews, not approval gates. You’ll end up with better outcomes and a better product.
Understand How Executives Actually Work
Jessica describes an executive’s calendar as a strobe light. They wake up to a list of urgent fires. They jump from a finance review to an interview to a legal problem to your product review. They haven’t thought about your project since the last time you met while you’ve been preparing for this meeting for weeks.
You need to help set up the context so that they understand right away why the thing you are pushing for matters.
Spend the first 30 seconds of any meeting setting context:
- We’re here to discuss X.
- Last time we met, we left off at Y.
- The goals for today are Z.
- Here’s how we’ll run this meeting.
Then ask them “Was there anything else you were hoping to cover today?”
If you’re doing a doc review, add a “Themes for Discussion” section at the top. Bubble up the most controversial or consequential points that can only be resolved in a meeting. Anything they can answer offline, handle offline.
Align With Their Incentives, Not Just Yours
Executives have their own pressures: board targets, OKRs, company-level metrics they’re accountable for. Your job is to understand those incentives and connect your work to them.
You need to comprehend how you orient your entire team so that everything aligns with the company startegy/ mission. For instance, your exec is chasing is enterprise revenue growth, and your team’s work doesn’t clearly ladder up to that, you’re going to struggle for buy-in regardless of how good your idea is.
Jessica makes a clear point about asking better questions.
Some to try:
- “What’s the board pushing you on right now?”
- “What pressures are you facing that keep you up at night?”
- “What are the key inputs to your success this quarter?”
Don’t forget that everyone has a boss – even your CEO will be getting pressure from somewhere. Understanding that pressure helps you frame your work as something that makes them more successful, not just something they need to approve.
Show your thinking
A common mistake is presenting only one option and leaving out all the different options that you considered, weighed off and left behind.
Jessica recommends presenting two or three options with clear reasoning for why you’re recommending one over the others. Be ready to show your reasoning and the trade offs you have considered – they will appreciate knowing that you came to a certain solution because you have looked at the data and understood the consequences behind the various options.
The related idea from the Minto Pyramid is worth noting here: lead with your recommendation, then support it with reasoning, rather than building up to a conclusion. However, this isnt a set in stone approach, some execs may want to read the whole doc, some may want data, some may want custoemr stories. Adapt your story to your audience.
Go In to Learn, Not to Convince
Approach your stakeholder meetings with curiosity and with a genuine intent to learn why they are thinking a certain way. Use the exec’s domain expertise, broader context, and experience to make your thinking better. When they say something you disagree with, resist the urge to push back immediately. Try:
- “That’s really interesting. What led you to believe that?”
- “How strongly do you feel about this?”
- “Do you think this trumps what we’re currently prioritising?”
These questions show genuine curiosity, and they help you extract the reasoning behind your execs’ position. Execs are practised at sounding certain. But often, when you dig in, you’ll find the conviction is softer than it sounds, or you’ll discover context you were missing.
Build Trust Before You Need It
Trust is the foundation that makes everything else work.
Show results. Ship things. Feed back the outcomes. “We worked with you on this, we shipped it, here’s what happened.” Impact builds momentum for your next, riskier idea.
Kill things. One of the most trust-building moves is to deprioritise or kill your own work. It signals you’re optimising for company outcomes, not protecting your scope. Execs notice this immediately.
Shrink the change. If an idea feels too risky for a full commitment, propose a one-week proof of concept or a time-boxed experiment. Reduce the stakes so the exec can say yes more easily. Set a clear check-in date: “We’ll come back to you on Friday with what we’ve learned.”
Invest in casual time. Not every interaction should be a pitch. Spending informal time with a leader, getting to know how they think, understanding their communication style, pays when you do need to make the big ask.
Think Like a CPO
If you want to grow into senior product leadership, you need to broaden your perspective beyond your feature or team. The execs who got to where they are did so by developing peripheral vision across the whole business.
Jessica puts it plainly: you get paid to be a domain expert. Your exec is looking for you to be the deepest person in the room. But depth alone isn’t enough. You also need to connect your work to the broader company mission and strategy.
Ask yourself: would the CEO be excited about what I’m shipping? If the answer is “they wouldn’t care,” that’s your sign. The people who get seen as strategic thinkers are the ones who consistently connect the dots between their local work and the global picture.
Why Influence Matters
As execution complexity drops and everyone becomes a builder, the skills that matter most are the distinctly human ones: having novel ideas grounded in user empathy, getting buy-in for those ideas, and building momentum to fund not just the V1, but the much harder V2, V3, and beyond is crucuial.
In this new AI world where everything can be built, the PM’s value shifts to choosing what to build, generating excitement, and rallying others to the cause.
Strategic clarity empowers teams to move fast in the right direction. And influence is how you get there.