30 Lessons from 30 Top Product Leaders
30 bite-sized lessons on crafting great products, becoming an AI-native product leader, and advancing your product career
Dear subscribers,
Today, I want to share 30 lessons from 30 leaders from my Behind the Craft podcast.
Speaking of the podcast, I have a great line-up of guests coming up, including:
Product leaders at OpenAI, Anthropic, Google DeepMind, and YouTube
Founders of top AI apps like Granola, Suno, and more
The next few episodes will focus on crafting great AI products and becoming an AI-native product leader. All my interviews are 100% free, so if you want to support me, please consider subscribing to my podcast on YouTube, Spotify, and Apple.
Now, let’s dive into the 30 bite-sized lessons from 30+ hours of conversations.
A quick favor…please respond to the poll below. I’m cooking something good :)
12 lessons on crafting great products
Katie Dill (Chief Design Officer, Stripe): It's just way too easy to ship something that's just “good enough” — we've got to get it out fast, we don't have the resources, we'll come back to it later. It's these micro-decisions every day that will make your product mediocre. So you must hold steadfast to "it's not good enough yet." Let's put another day into it. Let’s have the courage to stop the ship.
Kaz Nejatian (COO Shopify): Many people misunderstand how great products are built. They think a great product comes from a strategy document, but that’s untrue. Great products are built through continuous tinkering and adjustments. Every product that we love has been built this way.
Aravind Srinivas (CEO Perplexity): We don't do product review meetings. My mentality is: Why wait for a review meeting? Just give me the link to try the product so I can give feedback. Then, I'll check again in a few days. This is much faster than spending half a week preparing for a meeting with me.
Fareed Mosavat (ex-Slack): Don’t confuse the work behind the work with the actual work. The actual work is understanding customer problems, identifying solutions, and executing. The work behind the work includes all the intermediate steps — like product briefs, internal meetings, and product reviews. As a leader, you must recognize when this work behind the work takes over.
Yuhki Yamashita (CPO Figma): I think PMs who value craft have:
Attention to detail. They highlight small details that users care about.
Excitement for great experiences. They care about UX outside of metrics.
Emphasis on the user’s POV. They always put themselves in the user’s shoes.
Alex Cornell (Design Director, Meta AI): Designers should resist being too clever. If you get too clever, your interface will be beautiful but hard for users to understand. If I share flashy work, other designers would be stoked by it. But what users think matters and users usually prefer the familiar.
Cem Kansu (CPO, Duolingo): We take pride in using the term "unhinged" positively. When someone at Duolingo says a change is unhinged, the team did a good job. It's part of our product philosophy. Breaking sanitized product norms adds character.
Mihika Kapoor (Figma): If you’re building 0-1, be ready for emotional whiplash. It's natural to think that once you hit a high, the next step will be up and to the right. But it rarely is. Every high was immediately followed by a realization that it wasn't as good as I thought. Being persistent is key.
Lee Robinson (Vercel): The battle is won in the trenches of daily iterations. It could be a two-paragraph docs change because a dev didn’t get something. It could be one small UX issue with an input or button placement. For every developer you talk to, a hundred more don't say anything.
Jon Lax (ex-Meta VP Design): First, make something necessary and useful. Once that’s clear, then work on making it beautiful. Designers often get this backward. I’ve spent a lot of time polishing a product's final 10%, only to discover that it had no discernible effect on user satisfaction. Remember that if your product isn’t in the market, then you aren’t learning.
Dan Siroker (CEO Limitless): You can only have two of three things: scope, quality, and speed. My advice is to pick quality and speed over scope every time. Tech people want to build all kinds of cool features that don’t matter. Instead, start by solving a narrow use case well and then expand.
Lane Shackleton (CPO Coda): Shipping is often the fastest learning method.
We work hard to create a great culture for makers. Our default orientation is: “That seems like an interesting approach. How can we see how it feels? What's the best way to prototype that?”
6 lessons on becoming an AI-native product leader
Claire Vo (CPO, LaunchDarkly): AI lets anyone go from idea to prototype without strong technical skills. You could then put that prototype in front of customers and get feedback. So, candidly, I think PMs will be forced to build for customers directly. I’d love to see the lines between product, design, and engineering blur more so everyone can contribute to crafting the product.
Marily Nika (AI product lead, Google): You've already lost if a formal product review is the first time leadership sees your AI product. Instead, you must seek constant buy-in by communicating often, inviting people to test the product early, and ensuring that leadership understands AI’s non-deterministic nature.
Brian Balfour (CEO of Reforge): AI products have a novelty effect that captures initial attention. But the big question is: “How fast can you improve retention before the novelty wears off?” I’ve seen data showing that AI products retain at a much worse rate than non-AI products.
Tomer Cohen (CPO LinkedIn): Think fast and slow about the objective of your algorithm. You think fast by starting with your intuition. You think slowly by asking, “What could go wrong?” What could happen if you're successful in making your metric go up? There could be unintentional consequences, like spammers, bad actors, and filter bubbles.
Miqdad Jaffer (OpenAI): To address AI's non-deterministic nature, define clear product principles early. For example, the “let the merchant decide” principle led us to design a UX where merchants could review AI suggestions. We don’t want AI to sell stuff without the merchant's knowledge.
Dan Shipper (CEO Every): We're moving from a world where much IC work will become work where we’re managing AI models. If the metaphor for previous programming work was a sculptor, where every little chip is something you do, we're moving from that to thinking more like a gardener. You create the conditions for the plant to grow by adjusting the soil, etc.
12 lessons on advancing your product career
Ethan Evans (retired VP Amazon): The magic loop to advance your career:
Do your job well. Check-in regularly with your managers and peers to verify that you’re doing your current job well.
Ask your manager how you can help them. Managers love getting asked this question and always have something they need help with.
Do what they ask. Complete the task and update your manager along the way. Repeat steps 2-3 a few times to build trust.
Ask how you can help in a way that aligns with your goals. This could include increasing your scope, getting promoted, or joining a new team.
Do what they ask and repeat the loop from step 4.
Shishir Mehrotra (CEO Grammarly): Be selfless, people can spot selfishness from a mile away. They can tell if you're solving a problem or seeking credit. When you identify a problem outside your control, you must help others see why it matters. If they suspect an ulterior motive, they won’t listen to you.
Jiaona Zhang (CEO LinkTree): You must understand your career like a product. When building a product, you want to deeply understand who you're building for. What do they want? What are their pain points? You need to think about your career the same way. Too often, people just follow what others do or check boxes that seem "right." That’s leading so many PMs to burn out or want a change.
Sharmeen Chapp (Product at Stripe): There's a misconception that empathy and holding a high bar are mutually exclusive, but I don't believe that's true. You can do both. Giving tough feedback is kinder in the long run because it helps others grow. Just ensure your feedback is actionable so people know how to improve.
Satish Mummareddy (ex-Meta): Be someone that leaders want to sponsor by solving complex problems for them. When you're working on a leader's critical issues, they naturally invest time in the work and, by extension, in you. When you join a new team, you typically start with the least desirable projects. The key is to hit a high bar, even on seemingly small tasks, to earn the right to get priority work.
Scott Belsky (CPO Adobe): Empathy needs to come before vision. Empathy for the customer and their problem should drive you. You must talk to customers, watch them go about their day, and ask why they’re struggling with something to gain insight into crafting a compelling vision.
Justin Welsh (solopreneur): You should spend time on the 20% of things that maximize 80% of your intended outcome. Here’s how I do it:
Pick an intended outcome. Let's say it's to grow business revenue.
List every task you complete during the week. This could include writing, meetings, administrative work, and other activities.
Write the impact and hours for each task. Score each task from 1-10 based on how it helps your goal.
Calculate the ROI. Divide each task's impact score by the hours it takes. Sort all tasks by this ratio to see what's worth your time.
Eliminate, simplify, automate, and delegate (ESAD). Eliminate unimportant tasks and simplify complex ones. Then, automate or delegate.
Sanchan Saxena (VP Atlassian): Success is 80% luck and 20% skills. The people who are telling you otherwise are trying to sell you something. You get lucky by imagining the best-case outcome. Don't prepare for failure. Prepare for success. Try it, and you’ll see how it changes how you operate, show up at work, and what you aim for. That’s life advice, not just product management advice.
Chris Jones (SVPG): You must keep your network up. A good network will offer advice, mentorship, and job opportunities in good and bad times. It doesn’t have to have a big agenda, but keeping your network alive is important. That way, when there’s a downturn, you can be at the top of your mind for your network just like others are at the top of your mind.
Sachin Rekhi (founder and ex-LinkedIn): I got into product to talk to customers and design features. Instead, I rarely talked to customers directly - I had teams of PMs for that. While I owned high-level vision, the day-to-day work I loved about the products had disappeared. I was in my zone of excellence - work I was good at but found draining. I realized continuing on this path would take me further from the parts of the product I loved.
Elena Verna (Growth Dropbox): Imposter syndrome is a superpower. If you feel imposter syndrome, use it to make sure you know your shit before you open your mouth. When you feel imposter syndrome, you learn and do something outside your comfort zone. Lean into it because it could take you to the next level.
Deb Liu (CEO Ancestry): I want all parents to realize this is their most important job. You're replaceable at work, but you're not at home. Don't wait for "someday" to do important things with your family.
Wrap up
Hosting the Behind the Craft podcast takes time and effort, but I love doing it to:
Learn from smart people every week.
Share my learnings with all of you.
Thank you for watching. Let me know if you have suggestions for guests I should interview next.
Thank you for such an amazing collection!
Thanks Peter for compiling and bringing this up. It is of great help to read the snippets in easy bullets.