20 Product Lenny Rachitsky on The 3 Key Roles of the Product Manager, 5 Skills All The Best PMs Have, When To Hire Your First PM, How to Structure the Hiring Process for PMs & What Leaders Can Do to Make Their PMs Successful

In this episode of "20 Product," host Harry Stebbings is joined by Lenny Rujitsky, an influential figure in the product management space with over seven years of experience at Airbnb and a successful product management newsletter on Substack. Lenny discusses the importance of never settling for good enough, setting high standards, and working backwards from the ideal customer experience. He also shares insights on the role of a product manager, emphasizing the importance of shaping, shipping, and synchronizing the product while aligning with the business's goals. Additionally, Lenny provides valuable advice on hiring the first product manager, suggesting that founders should wait longer than they think is necessary and focus on finding candidates who have driven impact, collaborated effectively, and can adapt to the startup environment. He also touches on the challenges and rewards of angel investing, his approach to writing engaging content, and the long-term commitment it requires.

• Harry introduces Lenny Rujitsky as a seasoned product leader with over seven years of experience at Airbnb.
• Lenny has transitioned to running a successful newsletter and is an active angel investor with investments in companies like Figma, So Rare, Clubhouse, and more.
• Lenny is also known for his course on product management.
• Harry praises Lenny's genuine and kind nature and their friendship.

"Lenny is one of the ogs of product. Having spent over seven years at Airbnb as a product lead, he left to start his newsletter."

This quote highlights Lenny's experience in the product field and his venture into creating a popular newsletter.

• Product Board is a tool trusted by product managers and leaders to help bring products to market faster.
• Over 5000 companies use Product Board for product development.
• Maze is a research tool that allows product teams to gain user insights quickly with features like prototype testing, card sorting, and surveys.

"Product managers love product board, and product leaders trust product board to help them create products that matter."

This quote emphasizes the value of Product Board to product managers and leaders in developing and launching successful products.

• Lenny was born in Ukraine (formerly USSR) and immigrated to LA with his family.
• He started his career as an engineer at a startup in San Diego and eventually led engineering.
• Lenny founded a company in Montreal, which led to his connection with Airbnb and his eventual acquisition.
• At Airbnb, Lenny transitioned from engineering to product management and contributed significantly to the company's growth.

"The whole team basically joined as an engineer and he realized I should be a product manager instead of an engineer."

This quote explains Lenny's shift from engineering to product management during his time at Airbnb.

• Airbnb's success is attributed to its high standards and innovative approach.
• The company culture encourages going beyond the minimum and striving for unique solutions.
• Lenny shares an anecdote about the co-founder's expectation to create something the internet has never seen before.
• Airbnb's strategy involved working backwards from the ideal customer experience, inspired by storyboards used in films.

"One is just this idea of never settling for good enough and always setting the bar incredibly high."

Lenny explains how Airbnb's culture of high standards and innovation influenced his approach to product management.

• Product management is a multifaceted role that involves shaping, shipping, and synchronizing product development.
• It is about understanding customer insights, prioritizing features, and aligning teams to drive business impact.
• There is no universal definition of product management, as it varies across organizations and individuals.

"Basically, your job as a PM is to shape the product, to ship the product, and to synchronize the people and all of that in order to drive impact for the business."

Lenny provides a concise definition of the core responsibilities of a product manager.

• Listening to customers is crucial, but it's important to focus on their pain points rather than their proposed solutions.
• Lenny advises against building features solely based on customer requests without considering the overall user experience.
• He shares an example of Airbnb's decision not to implement a sort-by-price feature due to its negative impact on bookings.

"What you want to be listening to is what pain points do they have that you can then think about how to solve most creatively?"

This quote suggests that product managers should seek to understand customer pain points to create innovative solutions.

• Product managers should focus on past user behaviors rather than predictions of future actions.
• Observing product usage and inquiring about past issues can provide valuable insights for improvement.
• Lenny recommends the book "The Mom Test" for learning about effective customer research methods.

"What you want to focus on is what have you done in the past? What problems have you had that we can maybe solve for you?"

Lenny emphasizes the importance of understanding customers' past experiences to inform product development decisions.

• Founders often contemplate the timing for hiring their first product manager.
• The advice is to wait longer than anticipated to ensure the founder's vision and team dynamics are well-established.
• Product managers can become a redundant layer if hired too early, as founders typically have strong opinions and directions for product development.
• Three signs indicating the need for a product manager include frequent bottlenecks in decision-making, frequent misalignment among team members, and opportunities to explore new directions or ideas.

"My first piece of advice always is you should wait longer than you think you need to."

This quote emphasizes the importance of delaying the hiring of a product manager until it's absolutely necessary, to avoid potential complications in team dynamics and decision-making processes.

• The titles "Head of Product" and "Chief Product Officer" (CPO) are often used inconsistently.
• Typically, the first product manager hired is called the Head of Product.
• A CPO is a very senior role, usually filled when a company has a dozen or so product managers and is ready to scale its product efforts significantly.

"Chief product officer is usually like a very senior person that has done product for a long time."

This quote clarifies the distinction between the Head of Product and CPO roles, highlighting that a CPO is a senior position with significant experience in product management.

• The hiring process for product managers should assess key skills: execution, collaboration, leadership, vision and strategy, and customer insight extraction.
• A recommended approach involves a full-day interview with a project presentation and one-on-one interviews.
• The project aims to gauge the candidate’s problem-solving approach and instinct rather than finding the perfect solution.
• One-on-one interviews should cover the five key skills and cultural fit, with questions distributed among interviewers.

"There's a lot of ways to do it. Unclear exactly what the best way to do it, but the way I like to approach it, and it works, seems to work, is you basically bring a candidate in for a whole day."

This quote suggests that while there is no one-size-fits-all approach to hiring, a full-day interview with a mix of projects and one-on-one sessions has proven effective in assessing a candidate's fit for the product management role.

• Product managers often make the mistake of jumping to solutions without fully understanding the context or asking clarifying questions.
• Founders can mistakenly assume that a candidate will be a great PM based on their public persona or experience at a large company, which may not translate to success in a startup environment.

"One mistake that PMS often make is jumping to a solution."

This quote highlights a common error in product management interviews, where candidates focus on providing solutions rather than demonstrating their problem-solving process and understanding of the context.

• A PM might not be suitable for a startup if they have only demonstrated success in a large company environment, which operates differently from startups.
• Public thought leadership in product management does not necessarily equate to practical effectiveness in the role.

"It's a lot different to do the job than to be talking about it."

This quote warns against overvaluing a candidate's public commentary on product management without evidence of their ability to perform the role effectively in a practical, hands-on context.

• Individuals from companies like Facebook and Google may have the ability to succeed in a startup environment.
• Shorter tenure at a top-tier company may indicate adaptability to startup culture.
• Diverse company experience suggests flexibility and less likelihood of being entrenched in one way of working.
• The ability to think freshly and not just replicate big company methods is crucial.
• Preparedness for the distinct challenges of startup life is essential for success.

"One is they haven't been there that long and that way of working isn't fully trusted."

This quote suggests that a shorter duration at a big company might mean the individual hasn't fully assimilated into the larger company's culture, making them potentially more adaptable to a startup environment.

"Two, probably that they've worked at other companies and it hasn't been like Google hasn't been 80% of their career."

The diversity in work experience can be a sign of an individual's flexibility and adaptability, which are valuable traits in a startup setting.

• Product reviews are critical for product teams, especially product managers.
• Common issues in product reviews include losing focus on the problem being solved and getting sidetracked by design details.
• It's important to start reviews by clearly stating the problem the product or feature is intended to solve.
• Clarifying the type of feedback desired from the review can save time and keep the review focused.

"A lot of times you come to a product review, you're like, oh, check out these great new designs. Here's how it's going to work. Here's the flow, here's the interactions people start getting sucked into. It's like, awesome. Look at these colors."

This quote highlights the tendency for product reviews to become fixated on aesthetics rather than the underlying problem the product is addressing.

"You always want to come back to, here's the problem we're trying to solve with this feature."

Emphasizes the importance of maintaining focus on the problem during product reviews to ensure the product's development aligns with the intended goals.

• The size of the review group should be as small as possible to maintain efficiency.
• Include only those directly involved or necessary for the feedback process.
• Remote work may allow more people to listen in without actively participating, but the core group should remain limited.

"The rule of thumb is you want to make it as small as humanly possible while making sure people that need to hear that feedback are in the room."

This quote indicates the importance of keeping meetings streamlined to avoid unnecessary complexity and time wastage.

• A great designer is invaluable and can enhance the entire team's work.
• Treat designers as partners, not subordinates.
• The PM identifies the problem, and the designer focuses on the solution.
• Avoid being overly prescriptive with designers to encourage their creativity and problem-solving skills.

"Having a great designer is like having a superpower on your team, in my experience, because everything just gets better."

The quote emphasizes the significant impact a skilled designer can have on the team's morale and product quality.

"The PM's job. 80 20. 80%. Their job is to identify the problem that needs to be solved and make clear, here's what we're trying to solve and here's all the information around it."

This quote delineates the roles within a product team, highlighting the PM's responsibility for problem identification and the designer's role in crafting solutions.

• Onboarding should include meetings with key team members, reading material, and customer interactions.
• Building trust is crucial for a new PM to effectively lead the team.
• Leaders can foster trust by expressing confidence in the new PM and helping them achieve a quick win.

"You need the team to feel they can trust this person because they're kind of this leader that has just joined and now they have to listen to their judgment and kind of follow them."

This quote stresses the importance of trust in the relationship between a new PM and the existing team.

• A PM can lose the team's confidence by making poor decisions, being overly opinionated, and not listening to the team.
• It's vital for PMs to ensure that team members feel their input is valued and considered in decision-making.

"A PM, by default, can kind of drive the ship and it's easy for them to just be, I know what I'm doing, leave me alone."

This quote highlights the potential pitfalls of a PM who does not collaborate or value team input, which can erode trust and confidence.

• Mistakes offer valuable learning opportunities.
• It's essential to conduct thorough research to ensure a product addresses a real problem.
• Knowing when to pivot or abandon a project is a critical skill.

"The biggest product mistake that I made. So the first product that I worked on at Airbnb... Nobody really wanted to do this."

This quote is an admission of a past mistake and underscores the importance of validating a product concept with actual user demand.

• Regular reevaluation of projects to assess their impact and potential is necessary.
• Decisions should be based on metrics and the alignment with broader business goals.
• Leaders should treat failures as learning experiences and not diminish team confidence.

"How this played out is we were working on this for, like nine months, launched a quick version of it, and... the metrics were just like, not great."

This quote illustrates the importance of using concrete metrics to evaluate a product's success and knowing when to redirect efforts based on those metrics.

• Recognizing when to move on from a project is crucial for both career progression and emotional well-being.
• Teams often get fixated on making a particular project work, but acknowledging that it was a company directive rather than a personal choice can facilitate the transition away from it.

"That really helps because a lot of times people, teams are just like stuck. Just make this work. We really need to make this work. And if at some point you're just like, okay, it wasn't like even our idea. A lot of times let's just try to move on to something else that helps career wise and even just like emotionally speaking of kind of lessons from."

This quote emphasizes the importance of not being personally tied to a project's success or failure, as emotional detachment can help teams pivot more effectively.

• Angel investing has taught that having an amazing product alone is insufficient for success.
• Key factors for a successful product include solving a real problem and having a scalable growth strategy.

"Honestly, one of the things that I've learned from angel investing is just how the product itself is like an amazing product is not enough. There's so many amazing products that just have died."

Lenny Rajitsky points out that even outstanding products can fail if they do not address a significant problem or lack a growth strategy. This insight has influenced his approach to evaluating products.

• A great product must address a genuine problem to be successful.
• Growth strategies such as virality, SEO, or paid growth are crucial for reaching users at scale.

"Specifically, are you actually solving a problem people want? That's the fundamental element of all these things. And if a product is incredible but not solving a real problem, it doesn't matter, it's going to die."

Lenny Rajitsky highlights the foundational importance of solving a real problem in product development, suggesting that without addressing a genuine need, even the best products are doomed to fail.

• Lenny Rajitsky prefers the informal, low-pressure aspect of angel investing over the responsibilities of a full-time venture capitalist.
• He dislikes the tasks typically associated with VC work, such as financial modeling and fundraising.

"I like the angel investing layer of investing where it's like chill life, where I'm not responsible for a lot of people's money. I don't have to go chase deals on behalf of other people."

This quote reflects Lenny Rajitsky's preference for the relaxed and autonomous nature of angel investing compared to the more demanding and structured world of venture capitalism.

• Lenny Rajitsky is hesitant to scale up his investment activities despite encouragement, prioritizing personal joy over potential financial gains.
• He actively avoids activities that do not bring him joy, including managing a large investment fund.

"I've been trying to be very good at paying attention to things that bring me joy and doing more of those things and doing less of things that don't."

Lenny Rajitsky explains his approach to work and life, focusing on joy and fulfillment rather than scaling up activities that may lead to stress or dissatisfaction.

• An MVP should be clever and test the core concept of the product.
• Lenny Rajitsky recalls a startup with an MVP that involved travelers purchasing items internationally to deliver to customers.

"There's a startup that was helping you buy things internationally cheaply by finding someone traveling already from that country, and they go buy it and throw it in their backpack and then come to the US and deliver it to you or some central hub that gets delivered to you."

The quote describes an innovative MVP idea that leverages existing traveler routes to facilitate international purchases, showcasing creativity in testing a product concept.

• Opinions on tools and platforms can change over time based on utility and experience.
• Lenny Rajitsky has come to re-appreciate Slack as a powerful and easy-to-use platform for community engagement.

"I think Slack is something I've kind of come to re appreciate recently. I think Slack went through this like, it's so big and bulky and annoying. But I use it a lot now with the newsletter community and I've learned to reappreciate how great that product actually is."

This quote indicates a shift in Lenny Rajitsky's perception of Slack, moving from viewing it as cumbersome to recognizing its strengths in facilitating community interactions.

• The writing process involves selecting topics that generate excitement, as enthusiasm leads to better content.
• Different types of posts require different approaches, such as direct answers, guest posts, or research-driven content.

"I pick a topic I'm excited to write about up because I find that if I'd write about things I'm not excited about and things that just people want me to write about, it doesn't end up right."

Lenny Rajitsky underlines the importance of passion in the writing process, suggesting that writing about topics of genuine interest results in higher-quality content.

• Consistent content creation can be demanding, with the pressure to produce quality content regularly.
• Lenny Rajitsky discusses the challenge of maintaining excitement for new topics and the continuous cycle of content production.

"It's kind of just this never ending need to write something awesome. On the one hand, it's so incredible how much this generates and allows me to live the life that I lead. On the other hand, it's like in theory, I have to do this for the rest of my life because people are paying me monthly, buying annual plans for the next year."

The quote captures the dual nature of content creation: the rewarding aspect of influencing one's lifestyle and the daunting prospect of an endless cycle of production.

• New product leaders should seek feedback from their team on areas for improvement and act on it to create quick wins.
• Understanding the resources needed for a team's success is critical and should be assessed from a fresh perspective.

"Suggest that they ask everyone on their team, what's just like bugging you? What's something that we should improve? What's a process that's annoying? What's something that we can fix? And then go fix something."

Lenny Rajitsky advises new product leaders to engage with their teams to identify and address immediate issues, thereby establishing credibility and positive momentum.

• The goal is to improve the perception of product managers and demonstrate their value in enhancing team efficiency and happiness.
• There is a desire to change the negative stereotype that PMs are not beneficial to a team.

"So a lot of people really dislike product managers. And that makes me very sad. I think it's because a lot of people have worked with bad product managers and they kind of create this bad brand of PMS."

Lenny Rajitsky expresses concern over the negative reputation of product managers and suggests that improving the quality of PMs can alter this perception.

• Companies like Figma, Stripe, Tesla, and SpaceX have product strategies that impress due to their forward-thinking and long-term vision.
• Lenny Rajitsky admires the methodical approach these companies take to achieve their ambitious goals.

"SpaceX, I guess, is a good example, which is like a very obvious, just like 100 year roadmap vision, time horizon. It's just like this methodical approach to get to this insane vision step by step by step."

The quote praises SpaceX's strategic planning and its ability to execute a long-term vision through a series of methodical steps.

• Harry expresses his appreciation for Lenny Rajitsky's insights and encourages listeners to subscribe to his newsletter.
• Lenny Rajitsky thanks Harry for the conversation and looks forward to future interactions.

"Thanks so much Harry. This was awesome. Thanks. It was such a pleasure and honor."

Lenny Rajitsky concludes the conversation by showing gratitude for the opportunity to share his experiences and perspectives.