This Week #8: Splitting equity with late-joining co-founders, favorite roadmap templates, and small changes that improve your org

With special guest contributor Hunter Walk!

Hello and welcome to my humble newsletter, where I attempt to answer your questions and offer candid advice about building product, driving growth, working with other humans, and anything else that’s stressing you out at the office 🤝

If you’re returning from last week, thank you! If you’re new, nice to have you! Help spread the word by telling your friends 🙏

New this week: Special guest contributor Hunter Walk 🔥🤩🤯 answering one of your questions! Also, watch out for something very special coming next week.

On to this week’s questions…

Q: I have bootstrapped my startup to our recently launched MVP by using paid contractors, and I’m now looking to bring in key team members (at least a CTO) as co-founders. Given that I have not raised any funds yet, one of the potential CTO candidates has agreed to join me on an equity basis. What do you recommend I offer the CTO candidate to demonstrate that I really want to work with him as a co-founder, but at the same time not make a decision that will deter potential investors (e.g. issuing him preferred instead of vested common stock for his work/contributions)?

Though I’ve had a bit of experience with this, I wanted to make sure you got as complete and accurate an answer as possible — thus, I turned to the man, the myth, the legend: Hunter Walk. Hunter is a partner (and co-founder) at Homebrew, former PM at Google (AdSense, YouTube), has personally worked with over a hundred early-stage startups, and has shared a few strong perspectives on equity splits. He generously offered to share his perspective on your situation:

Congrats! Bringing on a key technical leader is a milestone that you should be proud of, and which will impress any potential investors. Your question around equity has a few components, but directionally you’re exactly right:

  • What’s the CTO’s value? If they’re a true cofounder, would you consider giving them equity starting around 10% of the company — all the way up to a share equal to yours? For a very early stage company, we see “late-arriving cofounders” all the time. Otherwise, senior engineers/founding team would usually receive 1-5% of the company. These are all averages and situations definitely differ.

  • The stock grant should be common shares with a standard vesting schedule. Even outside of investors, this will give you comfort that you have time to evaluate this new team member before handing away meaningful portions of your company. Any venture investor will likely begin a vesting schedule for you as well.

  • Given that they’ll start work during the vesting period, the CTO might ask for something from you which signifies commitments — such as if they’re terminated without cause pre-vesting cliff, that you grant them some negotiated amount of stock. In my mind, this seems fair. 

Good luck! Building a team and a culture is the best part of building a company!

Thank you, Hunter!

Q: What’s your favorite roadmap template that you like to use?

Yes! Here you go! This is courtesy of my former Airbnb colleague, Andrew Chen (not that Andrew Chen), who had some of the most thoughtful and well-executed roadmaps of any PM I’ve ever worked with. I’ve tried a lot of different tools over the years, and I always find myself always coming back to Google Sheets 🤷‍♂️

Below is a peek, but make sure to check out the full template.

Option 1: Organized by lever (my preference)

Option 2: Organized by product

Bonus: A timeline per team member

If you have something better, I’d love to see it! Reply to this email and share the wealth 🧐

Q: What’s one thing you’ve changed within your organization that has made your team meaningfully more effective?

I asked this question of you all last week, and you delivered 💛 We got a boatload of great stuff (and also ended up rocketing to the top of the Substack engagement rankings 😬).

Here are your top ten highest rated ideas:

  1. Keeping track of every piece of customer feedback we receive, and then actually following up after we've made improvements to let people know they've been heard. I created a template in case anyone is interested in trying out our methodology.” — Justin Hales

  2. Delivered monitoring/analytics with each feature implemented in the product. This made it easy to justify more budget by having a backlog of a pretty deep set of analytics by the time we were a few months into the project.” — Jacob M

  3. “After reading ‘Trillion Dollar Coach’, I liked the idea of ‘Trip Reports’. So I introduced a variation of that in our team meetings. Every Monday morning, I asked the team to send me photos of their weekend/vacation. I collated it into individual slides and at the start of our team meeting, we went around the room talking about your photos! (15 mins). This had a positive impact on the team. We got to know each other as humans outside of work. We let our guard down before talking about work. Especially great for new starters!” — Saffad Khan

  4. “I'm in an engineering first org, so I had to introduce product into our development processes in a valuable and non-intrusive way. I did this by introducing Product Discovery documents on topics that we want to address with the following structure.” — Yehia Khoja

  5. We started to have ‘monthly social events’ -- a rotating set of activity-based events that each person on the team would host. Anything from MassVR to Game Show Game Show. The structure shifted a decidedly introverted team to become much more collaborative and for the newer folks on the team to ask others for help. This then set up a structure where we now have weekly "pod" meetings where various folks collaborate on technical design, coding, and strategy in a way that I never expected!” — Shashin

  6. “Moving over to Basecamp instead of using Google Drive / Docs / Sheets.” — Monica Banks

  7. “(1) Daily Virtual Scrum over slack, where the team shares what are the things they are targeting to achieve that day. And at the end of the day, they share the status update against each line item they shared in the morning. It reinforces for the team to go through the allocated task, and think first thing in the morning, before they start executing, (2) Product Reviews every week/bi-weekly. We keep changing frequency based on the backlog, (3) We started writing the mission, vision, and strategy for the subsequent products that we are planning to introduce. It helped me personally to avoid many mistakes we did in the past based on this link where you shared, Lenny.” — Vikram

  8. “Created a deck on business terms used at our company that many may not be familiar with. Things like MRR, ACV, CAC, CTR, ASO, etc. The idea was to enable everyone to be more proactively involved in discussions whenever these terms are thrown around. Now we showcase this deck to every new joinee at the company during their onboarding! Public link to the deck.” — Sudeep Shukla

  9. “Normally developers would do a ‘Technical Conception’ before a project begins, and that would take a few days or weeks. What I now do as a Product Manager is a ‘Pre-Technical Conception & Legacy study’, where I:

    • Study the legacy product where the team will have to work on. I study all functional aspects, write documentation (super important) to keep track of my studies,and explain how the features & logic work.

    • While studying the function, I also take time to note down all technical aspects that I can understand (ex: database structure of this functional perimeter, API calls during feature interactions, workflow, etc) or any leads/suggestions I can give to the developer so that can help them do the Technical Conception faster.

    • This is a totally new process I created in my team & company. Not only did it benefit a lot the team, but it made the project deliveries significantly faster by making the developers obtain knowledge in advance and do very fast Technical Conceptions.

    Our development time of projects went 300% faster.” — Chaz

  10. “After reading 📚 UX for startups and other UX books in my first 2 weeks after joining the startup, we experimented with setting aside a day where all engineers 👨‍💻 focused on a certain list full of UX annoyances (not bugs) then send out an email with all improvements as we ate pizza 🍕 while solving them

    • 🚨On D-day, there was only 1 engineer who was available because the rest had emergencies.

    • We (me as UX & Front-end of course after discussions with the PM) moved the tickets from: 'Design in progress' 👉'Ready for Dev' 👉 'In Progress' 👉 'Code Review' 👉 'QA' 👉 'Done'

    • 🎉We managed to address 10% of all the UX annoyances.

    • After reflecting with the team 🧠, because we work in an agile way, we all decided that for every sprint ♺, we will be picking 1-2 UX Annoyances 😡 and adding them to the Backlog.

    This was a victory for the team! 🙌 Now we are not just looking at Painkillers (PM vs UX) but also Vitamins!” — Lewis Kang'ethe Ngugi

Thank you all for your ideas! Read the full list here, share yours if the mood strikes.

That’s it for this week!

Inspirations for the week ahead

  1. Read: Beyond Coffee — A Sustainable Guide to Nootropics, Adaptogens, and Mushrooms. Written by James Beshara (of Tilt, and Below the Line podcast fame), and just released today. It’s the most informative, well-research, and digestible (pun intended) read on these substances you’ll ever find. 🧠

  2. Watch: Advice on Organizing and Running Growth Teams from Dan Hockenmaier and Gustaf Alströmer. This video is from earlier this year but I just discovered it, and was super impressed with how much damn wisdom it has packed into it. 📈

  3. Subscribe: Nonzero Newsletter by Robert Wright. Wright wrote some of my favorite books, like Why Buddhism is True and Nonzero, so I was rather excited to find that he has his own Substack now. And it’s awesome. 🤓

If you’re finding it valuable, please share this newsletter with your friends.

And if you’d like some advice yourself, or just want to say hi, just reply to this email. I’ll tackle three reader questions each week (keeping your name and company anonymous) until you quit sending me questions. I definitely won’t have all of the answers, but hey, it’s free 🤷‍♂️


Lenny 👋

Share one thing that you’ve changed within your organization that has made your team meaningfully more effective

I’m traveling this week, so instead of skipping a week let’s try an experiment and throw out a question to y’all:

🤜 Share one thing that you’ve changed within your organization that has made your team meaningfully more effective  🤛

This could be anything from a new design review process, to how you approach meetings, to a sweet new template everyone loves. Click the big orange button below to share one thing that comes to mind, and upvote your favorite ideas — this should take no more than a couple of minutes. Go!

View 19 comments →

This Week #7: Effectively communicating about a failure to execs, managing founder expectations, and hiring a Director of PM

Hello and welcome to my humble newsletter, where I attempt to answer your questions and offer candid advice about building product, driving growth, working with other humans, and anything else that’s stressing you out at the office. 🤝

If you’re returning from last week, thank you! If you’re new, nice to have you! Help spread the word by telling your friends to sign up here. 🙏

New this week: A friendly reminder to click the little grey heart up near the headline, if you find this newsletter valuable. <3

On to this week’s questions…

Q: What are your thoughts on communicating failure, like missing our team’s set goals? I’m new to my job and the first idea I pitched got buy-in very quickly. However, even through the initial user tests went great — the actual MVP we launched is doing horribly. I am struggling on how to communicate this, and which actions to take. Unfortunately I am in a quite “old-fashioned” environment where sharing failure is not common.

Before getting into how to deliver bad news, a few suggestions to get your mind in the right place:

  1. Failure is super normal: A large percentage of technology projects fail. I would venture to say MOST projects fail, in one way another. Why? Because you’re doing something that has never been done before. That’s what makes them worth doing.

  2. You aren’t the project: Don’t equate a project’s success with your personal success. You are doing a job, to the best of your abilities. You’ve had successful projects in the past, and you will again. You’ve also had failures in the past, and you will again. And some of the best work happens when taking a big risky bet.

  3. It’s not that big of a deal: I’m going to assume no one died, no one got hurt, and that you didn’t blow a bunch of money and resources. If true, all that was really lost was some negligible amount of resources and time. To a large company, that is not a big deal. It happens all the time. This is part of the game in business. It will likely be forgotten within the year.

Now, a few suggestions for how to frame bad news to leadership:

  1. Be up front: The truth will come out. Don’t try to hide it. More than that, I’d encourage you to lean into it: “This project failed. Let me tell you what happened, what we’ve learned, and what we’re recommending as next steps.” Leaders respect people who are clear-headed, up-front, and take responsibility.

  2. Stay positive: Avoid coming into the discussion looking down and depressed. Your energy and body language will influence how folks feel. Smile, be friendly, and convey optimism for the future.

  3. Separate the idea from the execution: When a project fails, sometimes it’s because the idea was bad, but sometimes it’s because it was executed badly. It’s easy to assume that it was a bad idea, especially if you were the one executing it, but I’d encourage you to take a hard look at the project and decide if it’s worth taking another shot at it with a different approach.

  4. Describe the journey the project has been on: Before diving into the results, paint a (succinct) picture of the sequence of events the led you to launch this MVP. It sounds like there was a lot of excitement for this idea — remind people why they were so bullish on it. Include early successes, user quotes, and learnings along the way. A visual timeline is often a good way to present this.

  5. Share what worked: What did you learn through this experience? What theories did you disprove? What surprised you and your team most? As Eric Ries taught us, the best way to measure the progress of new endeavors by how much you’ve learned.

  6. Have a clear plan for next steps: Building on the previous point, it’s extremely important that you have a clear recommendation for what to do next. This is how you turn a failure into an opportunity. Looking at the learnings from this experience, what should the company do next? Folks will be looking to you to guide them. This could be simply killing the project quickly and moving on. Or pivoting to something that showed signs of success. Or taking a whole new approach to the same problem. I’d spend most of your time thinking through this part.

  7. Show you care: Your company leaders will want to feel that you are committed and excited about the work, and to moving forward on whatever path ends up being chosen. If you do still care — make that clear.

Bonus: Watch this documentary about General Magic to see how beneficial failure can sometimes be.

Q: How do you, as a product managers, manage expectations with founders when their idea has to change? We’re well funded, and have been trying to scale a product — but it’s not working. We’re also feeling a lot of pressure from the board.

I’ve included this question because there’s a lot of overlap between it and the previous question, but with two important difference: (1) the attachment to the idea will be much stronger, and (2) the impact of changing it will be much larger. Basically, it’s a much harder version of the above question. Sorry 😭

When looking to change someone’s mind about something they firmly believe in, here are some tactics that have worked for me:

  1. Bring them on the journey with you: It takes time to change someone’s mind. Particularly something as big as a founder’s core idea. How might you bring them along the same journey you went on that convinced you that this was the wrong direction? What were the key data points, experiences, and learnings for you? Share them as you experience them, with your takeaways, and always with a “here’s what we’re doing next to continue learning how to make it work.” I share a story of this kind of experience in the introduction to this essay.

  2. Align on the key hypothesis and test them one by one: Something is keeping your founder convinced this is a great idea. Listen to these insights, and the assumptions behind them. Then, together, come up with a set of tests that you can cheaply run to vet these assumptions. Ask what would convince them that maybe this isn’t right. At some point, you’ll either run out of things to test, or you’ll be able to show that maybe it’s working.

  3. Stay optimistic: It’s important that you come across as being on the same side as the founder — you are there to help uncover how to make this work. Be the person that comes up with the hypothesis to test, with next steps after each test, and a running set of conclusions.

  4. Show them irrefutable data: Even though data isn’t everything at this stage, there often is compelling data (either quantitative or qualitative) that can paint a pretty clear picture of what’s not working. An approach here is to work backward from what a compelling case for pivoting would be (e.g. what data points would this need, what kinds of quotes would you need from users), and then go get those.

  5. Have someone they trust convince them: It’s often tough and IC on the team to convince the founder of anything they don’t want to believe. Does the founder have a trusted advisor that you can pitch on your perspective, and then work together to influence the founder?

  6. Give the founder a chance to save face: It’s difficult for anyone to admit they are wrong. Especially a company leader. Knowing this, find a way to make it feel like less of a failure and more of an evolution based on new learnings. “You made a decision based on prior information, and it was the right one given what you knew, but now that we know more, it makes sense to change direction.”

  7. Accept they may never change their mind: I have many friends who have worked for founders are CEOs who are extremely stubborn and essentially are impossible to convince they are wrong. If you begin to feel that’s the case in your company, step one is to recognize that, and step two is to decide if you want to continue working in that environment.

Q: Could you flip the "interviewing for a Director PM role" question from a few weeks back and share your thoughts on what interviewers should look for when hiring a Director of PM?

I’ve recently come across the writings of Jackie Bavaro, who has some stellar content on hiring Product Managers. So first of all, go read this and then this. In addition First Round has a great roundup of PM hiring advice.

Now, what is different between hiring a Director of PM vs. an IC PM? I’d say the top three differences are that they will be (1) managing PMs, (2) taking on large scope, and (3) working closely with senior leaders. Here are some of my favorite interview questions for the seven key skills to focus on for interviewing PM Director candidates (same as the previous answer, plus two new ones to keep things interesting):

  1. Long-term strategic thinking

    1. Have them pick a 3+ month-long project they’ve led and are proud of, and to walk you through it from inception to completion. I jump in along the way to explore how they thought strategically about each step of the process.

    2. Present them with a sample challenge that you’re facing at our company and have them talk through how they wouldd tackle this problem, from vision to strategy to through the execution.

    3. Taking the above concept further, I’ve found great signal in giving a candidate 2 hours to tackle a challenge, on their own at a desk in the office, and then to present their proposal to the interview panel.

  2. People leadership

    1. “When I ask them, what would people you’ve managed in the past say about you? What about people your peers?”

    2. ‘Tell me about a time you’ve had to deal with a low-performer. How did you communicate something was wrong? And what did you do to help them improve?”

    3. “Tell me about a time when a team you were leading didn’t gel. Why do you think that happened, and what have you learned?”

  3. Stakeholder management

    1. “Tell me about a time you took the initiative and make something happen that needed to happen.”

    2. “Tell me about a time you strongly disagreed with your manager. What did you do to convince them that you were right, and what happened?”

    3. “Tell me about a time you were behind schedule on a high-visibility project — how did you communicate the news to stakeholders? How’d it go?”

  4. Impact

    1. “What measurable impact have you had at your previous companies?”

    2. “How do you measure the impact of someone in your role?”

    3. “Say we look back a year from now, what kind of impact would you like to have made?”

  5. Communication

    1. “How do you keep your team updated on what’s happening higher up in the org?”

    2. “How do you keep your stakeholders updated on what’s happening within your team?”

    3. “Tell me about a time you messed up communicating something important to either your team or to execs — and what did you learn from that?”

  6. Decision making

    1. “Tell me about a time you had to make a decision that was counter to what your team wanted. How did you work through that?”

    2. “When do you wait for consensus vs. making a call yourself?”

    3. “Tell me about a time when you went against what the data was telling you?”

  7. Vision

    1. “Tell me about a time you had to develop a vision for a product or team.”

    2. “How important is it to have a vision for your product or team?”

    3. “What was the vision for your previous product or team?”

  8. Hiring

    1. “Tell me about one of your favorite (or hardest) hiring experiences in the past — how’d you find them, how’d you close them?”

    2. “How much of your time do you expect to spend hiring?”

    3. “What’s your standard interview loop process?”

Bonus: Other questions I love

  • “What’s something you’re better at than most other people? What’s your superpower?”

  • “What’s something you’re working to improve?”

  • “What was your biggest product mistake? What did you learn from it?”

That’s it for this week!

Inspirations for the week ahead

  1. Watch: Camera Drone Follows Rollercoaster to Capture Dizzying Cinematic Footage — 👌

  2. Listen: Nir Eyal on Below the Line podcast — Practical tips to become less distractable 🤫

  3. Behold: Our Dazzling Night Sky When the Milky Way Collides with Andromeda in 4 Billion Years 🤯

If you’re finding it valuable, please share this newsletter with your friends.

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And if you’d like some advice yourself, or just want to say hi, just reply to this email. I’ll tackle three reader questions each week (keeping your name and company anonymous) until you quit sending me questions. I definitely won’t have all of the answers, but hey, it’s free 🤷‍♂️


Lenny 👋

This Week #6: Cultivating good relationships with distributed co-workers, building trust to accelerate growth, and leveling up as a PM when you have extra time

With special guest contributor Hiten Shah!

Hello and welcome to my humble newsletter, where I attempt to answer your questions and offer candid advice about building product, driving growth, working with other humans, and anything else that’s stressing you out at the office. 🤝

If you’re returning from last week, thank you! If you’re new, nice to have you! Help spread the word by telling your friends to sign up here. 🙏

New this week: The one and only Hiten Shah guest-answering one of your questions. Don’t miss it! 😍 

On to this week’s questions…

Q: In the next year, more and more of the engineers and designers I’ll be interacting with will be remote. What advice do you have for cultivating a good relationship with remote engineers and designers?

Since I have very little experience with extended remote work myself, I decided to ask someone who has lived (and written about) this life for years, Hiten Shah, to take this question. He immediately (and generously) agreed. If you don’t know Hiten, he’s a legend. Not only is he one of the nicest, most insightful, and most helpful people you’ll ever meet, he also co-founded four companies (KISSmetrics, Crazy Egg, Quick Sprout, and most recently FYI), has invested in 100+ more, and for years has been putting out loads of rich content about startups, growth , and appropriately . . . remote work. Here’s Hiten’s take:

On a distributed team, you are not in the same physical space, so you don’t get to see each other in-person. You don’t get to just walk up to someone’s desk and show them something, or ask them a quick question. Instead, all of the forms of communication with your team are digital: text, voice, and video.

As a result, remote work leads to an increase in miscommunication.

For engineers and designers, the number one impact of miscommunication is being forced to redo work, and make unexpected changes after you think you are done. All because of something that got lost in translation.

Good relationships with remote engineers and designers require ensuring that there are methods for avoiding miscommunication. You do this by maintaining clarity. Your goal on a remote team is to create a culture where it’s OK to ask for clarification when something feels unclear. This is the key to successfully working on a remote team. Ensuring that everyone is on the same page about exactly what needs to be done.

Here are a few tactical best practices to help you build good relationships with your co-workers:

  1. Always write things down: Whenever you’re on a call, make sure that anything that’s important gets written down. Options that were discussed, decisions that were made and next steps, plus who is going to do them. Go even further for your recurring meetings and have a single document that incorporates an agenda and structured meeting notes of what was discussed each time. It’s also important to fully and clearly document specs to ensure understanding. The more that gets documented, the better.

  2. Screenshare when possible: If you’re talking about work that an engineer or designer is doing, screenshare and go right into the tool where their work and tasks are documented. For example, this could be your ticketing system, a spec document or even an Invision prototype. Work together by having a discussion, going back and forth on the feedback and ideally collaborating in the appropriate tool while on the call. This way nobody has to remember to update things later.

  3. Postmortem everything that’s shipped: Especially whenever larger bodies of work are completed and shipped to customers. Marketing, product, big customer wins. It should all be postmortemed to understand what went well and what didn’t. This way you are constantly assessing how things are going and are able to discuss how to improve them. Having great process and documentation is the key to remote work. You can’t just come up with a process and expect it to work well for you without reviewing and iterating it.

For more remote work best practices that are backed by research that we’ve done, read these 11 best practices for working remotely written by my co-founder Marie.

Thanks Hiten!

Q: I work at a Fintech company — how would you think about growth here? Our main challenge is building trust with users (because without that they won’t want to share any of their information), and not being a daily use product.

First of all, let’s talk about a few ways you can build trust with users:

  1. Social proof: If people that you trust are using a product, you’ll certainly be more likely to trust it. Some examples of this in action. How might you leverage data and testimonials from people already using your service to create social proof — how many people are using it, what kind of people, from where, and for what purpose? Help your users immediately see that people just like them are already using and loving your product.

  2. Authority: If someone in authority has vetted a product, you’ll be much more likely to trust it. Some examples of this in action. How might you surface your certifications, approvals, badges, awards, seals, or endorsements from authority figures? How might you acquire more of these? Whatever you have — make sure your users see these early and often.

  3. Guarantees: If something goes wrong, who’s got my back? What’s the downside of giving this product a shot? How might you make your users feel like they’ll be safe and protected no matter what? The Airbnb Host Guarantee was an incredibly powerful tool for getting new hosts over the hump of opening their home up to strangers.

  4. Reputation: This is likely less relevant to your business, but reviews from other users (e.g. Yelp reviews, Uber reviews, Airbnb reviews) are one of the most powerful ways to communicate trust. If many other people have had a good experience, it’s likely you will too. Here’s a good read on this topic.

  5. Great UX: A badly designed site/app immediately introduces suspicion. Particularly when dealing with money. Pay attention to the details — the resolution of images, padding, grammar, performance, and general visual polish. Listen for these issues in user research. Little things can make a big psychological impact here. Watch Joe Gebbia’s TED talk about how Airbnb designs for trust.

  6. Deliver: With our increasing interconnectedness, word-of-mouth spreads quickly. Particularly if you do something wrong. Nothing destroys trust in your brand more quickly. At the same time, if you consistently provide a great experience, and deliver on your promise — that’s how you’ll build real long-term trust. The Amazon Flywheel is a good example of this in action.

With that in mind, three growth levers I’d suggest you explore:

  1. Top-of-funnel: Referrals. For a product that relies on trust, there’s nothing more powerful than an endorsement from a friend. Airbnb had a similar trust challenge, both on the guest side (“stay in a stranger’s home, are you crazy?”) and on the host side (“have a stranger stay in my home, are you crazy??”). Referrals proved to be the single biggest attributable growth lever on both sides of the marketplace. When designing your referrals program, it’s important that (1) the referer has a meaningful incentive, be it cash or credits, that (2) this program is easily discoverable, and that (3) you are incentivizing the right behavior — the referral reward should only pay out once the new user has hit a valuable milestone.

  2. Mid-funnel: Landing page(s). Start building trust from the first moment a user visits your site. How might you leverage some of the ideas I referenced above to instill a strong sense of trust in your product immediately? How might you continue that message throughout the remaining experience? What concerns do people have, at which stage of the flow, and what are you doing to address them? Also, no matter what you’re selling — is the value prop for your product crystal clear? What will compel users to stick around? Make sure to show these pages to real users and listen to their reactions. Continue iterating on this indefinitely.

  3. End-of-funnel: Remind users of the value you’re providing. Without knowing what exactly it is your product is, I’ll take a guess and assume that it’s a “set it and forget it” kind of service, where you sign-up, connect your financial accounts, and good things happen for me. If true, then find ways to remind users of all of the good that you’re doing, and why they’d be fools for quitting. Wealthfront and Betterment do a great of this with a regular email showing me how much interest I’ve earned lifetime with them.

Q: I’ve been a PM at a startup for about 18 months. A few months ago the business shut down, and for a variety of reasons I’ve decided to take some time off to do some extended travel. With months of travel ahead of me, I’d like to use this time to level up my PM game, and I wanted to get your advice on what you think would be the highest leverage learning opportunities during this time.

Truthfully, it’s tough to get significantly better at product management without actually doing product management. No amount of reading, classes, or discussions will be as good a teacher as doing the actual work. However, having time to step back, to process, to read deeply, and to build complementary skills is a rare gift and can indeed accelerate your progress once you return to the job. Here are a few things I’d suggest for your time off:

  1. Follow your energy: What have you been yearning to do or learn while employed, but have been unable to because you’ve been too busy or lacked the energy? Maybe it’s learning to design, or learning to code, or getting better with data. Do that. Do the thing that you are most pulled towards. Even if it’s not directly beneficial to your job today, at the worst you’ll feel much better finally having scratched that itch.

  2. Read, with a goal: Determine 2-3 skills you most want to develop (strategy? execution? leadership?), pick a set of books and articles that speak to these skills, and work through them. Here’s a set of curated articles and books I previously put together for each of the primary PM skills. I’m happy to share more if you let me know what skills you’d like to focus on. Be careful adding too many items to your list, or book/articles that you aren’t excited about, because you’ll quickly get bored or overwhelmed, and lose motivation.

  3. Read, without a goal: Not all things need to be goal-oriented. Make time to read stuff you’re super excited about even if it’s only tangentially related. Biographies, history books, and documentaries are great for this. As an example of this in action, here’s the story about how Walt Disney’s biography changed Airbnb’s strategy.

  4. Write: One of the main reasons I’ve started writing is because it helps me learn. Consider doing some writing, reflecting both on what you’ve learned over the past 18 months, and on the reading that you’re doing on your time off. This can be as simple as a bullet list of PM learnings, or as in-depth as a Medium article.

  5. Take experiential classes: At a high level, product management, as a skillset, is a combination of leadership + business thinking + product design. Instead of reading about these skills, find some local classes that will help you build them in a different context. Want to work on leadership — maybe take a class on teaching an adventure sport. Want to work on business thinking — maybe take a class on running a local business. Want to work on product design — maybe take a class making pottery. Use this opportunity to look beyond the digital world.

That’s it for this week!

Inspirations for the week ahead

  1. Read: Which Way Do You Run? by Ben Horowitz — “Almost all CEOs know where the problems are, but only the truly elite ones run towards the fear.” 💪

  2. Listen: The Portal by Eric Weinstein — An fantastic new podcast that will make you smarter. Start with the episodes with Andrew Yang, Werner Herzog, or Peter Thiel.

  3. Watch: Optical grape sorting 😳

If you’re finding value here, please share this newsletter with your friends.

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And if you’d like some advice yourself, or just want to say hi, just reply to this email. I’ll tackle three reader questions each week (keeping your name and company anonymous) until you quit sending me questions. I definitely won’t have all of the answers, but hey, it’s free 🤷‍♂️


Lenny 👋

This Week #5: Overcoming impostor syndrome, introducing growth to an org, and how to partner with your Data Scientist

Hello and welcome to my humble newsletter, where I attempt to answer your questions and offer candid advice about building product, driving growth, working with other humans, and anything else that’s stressing you out at the office. 🤝

If you’re returning from last week, thank you! If you’re new, nice to have you! Help spread the word by telling your friends to sign up here. 😎

New this week: A guest contributor 😍 Check out the second question about impostor syndrome. And from last week — our comment experiment from last week didn’t work. Turns you need to be on a paid plan for that feature to work. This is how we learn. 😩

On to this week’s questions…

Q: I’m wondering if you had any thoughts on imposter syndrome and Product Management? This job is really freaking hard and most days I feel like I’m terrible at my job despite external signals like getting put up for promotion.

I ❤ this question. I went through some serious imposter syndrome myself for several years (does it ever totally go away?) right after a promotion at Airbnb. I had this sense that if I made a single mistake, in a meeting or with a launch, even once, everyone would see that I have no idea what I was doing and that everything would crumble. It was real and it was rough. What helped me most during that period was actually talking to a professional coach. She helped me see different perspectives that I hadn’t seen, to understand that the downside wasn’t as bad as I thought, and that things were actually going really well.

🎉 As a treat for you all, my favorite executive coach Kate Hosie generously offered to share her advice on this question! Occasionally I’ll ask experts in a field to take certain questions, and this week we’re very lucky to have Kate help out. Enjoy! 🎉

I have a few points of view on this question, coming from different angles. I’ll be starting from a place of self-compassion or acceptance about your Imposter Syndrome, and then shifting more towards a position of growth. Try not to think of these as mutually exclusive, believing that the only way to grow is to judge yourself. Instead, self-judgment prohibits sustained healthy growth. It’s really difficult to improve ourselves when we don’t even want to truly look at ourselves. Instead, if you can imagine a polarity with self-compassion and acceptance to the far left, and growth to the far right, ask yourself what you recommend most for yourself right now. I sometimes see my work as both "comforting the afflicted and afflicting the comfortable", so knowing whether you’re more afflicted or maybe a little too comfortable may help you to decide what’s more important right now:

  1. See it as a sign of success: Imposter Syndrome is normal and is generally a sign that you’re enjoying some degree of success in your life. Think of it this way; if you were pumping gas or stacking shelves somewhere, you wouldn’t be experiencing Imposter Syndrome. So, first of all, you could stop and give yourself a pat on the back for at least being in a role that’s challenging enough to warrant having Imposter Syndrome about in the first place. As I’ve mentioned above, acceptance is underrated and the first step in any real change.

  2. See the truth in it: Sometimes people experience Imposter Syndrome because it’s true. You may be in a new role or a new industry. Your role may be growing faster than you are. This happens all day long so, no judgment. However, the degree of negative emotion you’re experiencing regularly is directly related to the level of responsibility you’re taking in your life. It’s like a see-saw or teeter-totter; when negative emotion is up, responsibility is down. And vice versa. Only every single time. So, if your negative emotions are recurring it can help to step back and ask yourself where you’re not taking responsibility in your role. For example, where are you procrastinating, making excuses, blaming others, not addressing root cause issues, ignoring structural problems, not developing yourself but instead just coasting, not really delivering but instead going through the motions? Look for where you’re out of integrity with yourself and what you know you need to be doing.

  3. Look for burnout: Start to pay attention to what degree this feeling of you being an imposter is valid, and to what degree this may just be what I call “the burnout talking”. Career burnout is very common and can be primarily traced back to three causes: 1) over-caring, 2) lack of appreciation, and/or 3) not working to your strengths or at the appropriate ability. Burnout directly impacts our self-confidence and our self-talk invariably suffers, where we start to think that we’re not actually that good at what we’re doing anyway. Not a fun loop to find yourself in. I’ll speak to these causes of burnout one at a time:

    • Over-caring: To what degree are you caring appropriately about your work? Versus over-caring, where your identity is all wrapped up in what you do and the rest of your life is suffering from malnourishment. If you’re over-caring you’re likely to be over-investing and have lost your sense of perspective. Perspective Taking Capacity (PTC) is critical in leading others through ambiguity and it’s often lost when we don’t take sufficient breaks, vacations, or sufficient care of ourselves. A typical scenario is when someone sacrifices sleep to get more done, thinking that they will only be impacted physically by the sacrifice. However, a lack of sleep impacts us physically, mentally, psychologically, and emotionally. How much sleep have you been getting lately? To what degree is that impacting how you feel about yourself? I will hazard a guess and say, more than you likely realize. Focusing on your own peak performance, or what I prefer to call “optimal functioning”, through getting your energizing and restoration habits in place is critical and almost invariably requires a greater focus on recovery than most people give themselves. 

    • Lack of appreciation: This is also pretty common. You can be grinding things out and no one even notices or cares, or even worse, you may feel criticized or judged for everything you have yet to do. If you expect appreciation to come from above then you’re limiting yourself. Studies done on burnout recovery and prevention show that appreciation from peers is just as impactful as appreciation from whoever you’re responsible to, so think about how you may like to build this into or across your own teams and peer groups as a permanent structure in how you run your meetings, conduct your 1:1’s, etc. Also, acknowledging your own progress helps. It’s easy to see everything we still have not yet done, so find a way to pay attention to your own progress and celebrate that where possible. We can’t get everything done in one day, one week, but it’s highly likely that you’re always moving forward. Don’t lose sight of that and give yourself some credit.

    • Not working to your strengths or at the appropriate ability: Most people build their careers on what depletes them. To what degree do you even know what your intrinsic strengths are, or what is naturally energizing for you versus what you find depleting? Knowing and using your strengths will help you avoid burnout. When you avoid burnout you will be less inclined to experience that fun voice in your head that we call the Imposter Syndrome. Also, you would think that operating at a level below your actual ability would make you feel better about yourself, but the reverse is true. It diminishes your self-confidence. So, you may like to step back and ask yourself if you’re operating at the right level or whether you’re living on your knees. No judgment, please. Just curiosity and compassion, which will allow you to be more honest with yourself. 

  4. Sometimes the job is just plain hard: Product Management is challenging. And that’s OK. You don’t need to be perfect. What I do suggest for people in highly complex roles is that they do four things in particular, which comes from The Four Factor Model I learned from Professor Michael Cavanagh, who is an expert in complexity theory from the University of Sydney. Those things are:

    • Keep your Perspective Taking Capacity (mentioned above) by looking at the big picture — more broadly than you would normally be inclined to do. A simple way to picture this is imagining that you’re working at ground level versus looking at things from the top of a tall tower. When you’re at the top of the tower you have Perspective Taking Capacity and an elevated ability to see all the connected parts. You can’t do this if you’re grinding it out at the coal face. If you’re leading others, the top of the tower is where you need to spend most, if not all, of your time, and to help others see what you can see from that vantage point.

    • Take responsibility for your own Mindfulness, for example by starting some kind of meditation practice of even ten minutes a day using something like Headspace. This will help you keep yourself calm amongst all of VUCA (Volatility, Uncertainty, Complexity, and Ambiguity) elements you, your organization, your industry is exposed to.

    • Ensure you have a clear shared Purpose with those around you to keep you aligned when everything starts to come undone. It will bring you back to what matters most and prevents thrash.

    • Stay in Dialogue. Talk often, talk broadly, and listen to people you don’t want to listen to. Stay open. Share what you see when you see it. This takes the burden from you and you will find that you are a part of a shared responsibility. You can’t do your role on your own. Remember that. A great PM doesn’t try to work things out on their own, but instead stays in good open relationship, and in dialogue, as things constantly emerge. Be an open system. This is realistic. Be realistic.

You can learn more about Katherine Hosie at, or by emailing her at

Q: What’s your advice for introducing growth to a company, which has a pretty standard way of thinking about it, i.e. “sales and marketing”? The more involved I get, the more I notice that we can really benefit from switching our mentality towards “growth” and breaking down the barriers between marketing, product, sales, etc.

I’m inferring that you want to introduce a more cross-functional and “analytical” mindset to growth — what used to be known as “growth hacking” but is now known as just a “growth team”:

[A growth team] is a hybrid of marketer and coders, who looks at the traditional question of “How do I get customers for my product?” and answers with A/B tests, landing pages, viral factor, email deliverability, etc. On top of this, they layer the discipline of direct marketing, with its emphasis on quantitative measurement, scenario modeling via spreadsheets, and a lot of database queries. If a startup is pre-product/market fit, [a growth team] can make sure virality is embedded at the core of a product. After product/market fit, they can help run up the score on what’s already working.

— Andrew Chen, Growth Hacker is the new VP Marketing

Good news: You’re right for trying to make this shift. There’s no question that the tighter and unified your product, data, engineering, research, marketing, and sales teams are, the more bottom-line impact (and less waste) you’ll end up seeing. It just makes sense — fewer silos, more collaboration, being data-informed, and leveraging complementary skill-sets leads to better outcomes. This is how all companies should and will operate eventually, and you’re pulling your company towards that future.

Bad news: This will be hard. Once a company has a certain mindset for how growth happens, and enough senior leaders who want to protect their jobs/teams/power, it’s difficult to dislodge.

Good news: Reality isn’t going to change because people don’t want it. Change will come for your growth org eventually, whether folks like it or not.

A few suggestions for how to accelerate the shift towards a “growth team”:

  1. Bring in experts: Invite growth leaders from companies that your leaders admire to meet with your company’s leaders. Or even have them do a fireside chat that leaders attend. Ask them pointed questions about how they operate, and how marketing and sales fit in. An outside voice is often very impactful. These sorts of chats had a big impact at Airbnb.

  2. Benchmark against other companies: A lighter-weight approach to the above would be to simply talk to these external folks yourself and collect learnings. Then, build that into a pitch that you share with your execs.

  3. Get buy-in from the top: For a real growth org to spring up, you need support from the CEO (or another senior leader). They need to make it clear that this is important and requires the support of the existing marketing and sales leaders. Without this, you’ll run into all kinds of friction, politics, and tension. Why? Because people will feel like their jobs are being threatened. Help them see where they’d fit into this new structure.

  4. Run an experiment: If you can’t get buy-in on a big change, get buy-in for a small change — ask for a six-month experiment where you pull together a data scientist, an engineer, a PM (and ideally a designer and researcher), and see what kind of impact you can make. Then, show your leaders how much (measurable) growth this small investment has made, and what you do with 5x more resources. Try to actually get six months — otherwise, you’ll risk running out of time by the time you figure out how to operate as a team, instrument the product, design, build, launch, and wait for the results of your experiments.

  5. Become a thought leader within the org: Send a weekly “This Week in Growth” email highlighting learnings from your company, and other companies. Invite weekly or monthly speakers to talk about growth to your team. Start a Slack room where you jam on growth topics. Share podcasts, share articles, share books about growth. Become the person everyone thinks about when they think “How the heck do we drive more growth??”

See Question #3 in this previous post for advice on how to build your growth team once you have buy-in.

Q: I recently joined a company as a data scientist. While the team I am on is great and supportive, the engineering and product leads have not had much experience working with data scientists and the like. As a result, we have found it difficult to work out our processes and I don't feel I am contributing as much as I would like. So I suppose, in short, my question is - how have you found success using data specialists in cross-functional teams?

In my experience, having a data scientist on your team is like having a superpower. You’ll see things you wouldn’t have seen, make faster + better decisions, and have significantly more impact. Eventually, your teammates will realize this too.

Here’s what you do. Send the following email to your partners on the team, and if they disagree, send them my way:


I asked this guy Lenny for advice on how to get the most value out of your Data Scientist, here’s what he said:

  1. Treat them as a partner: Share *what* you are trying to achieve and *why*, not just the queries you need run. If they are senior (and good), you’ll be astounded by how many new ideas and novel insights they’ll bring to the table. 🤝

  2. Know what motivates them: Find out what kind of work your DS partner enjoys doing most, and try to give them as much of that type of work as possible (when there is flexibility). Some DSs love knocking out answers to questions. Some love tackling long-term deep problems. Some love low-level infrastructure work. 🤗

  3. Prioritize asks: DSs are often barraged with questions, seemingly always urgent — a lot of “this’ll be quick!” Work with your DS on a (public) prioritized list of outstanding TODOs, and when new asks come in, work together on the updates priorities. Review together weekly. 🧐

  4. Know what you’ll do with the answer: For the questions you ask your DS, have a clear and precise answer for “What will you you do with the answer when you have it?” Your DS should ask you this each time. You will find that many of the things you want to know are not actually going to change anything, and thus not worth looking into.

  5. Share findings widely: Each time a data question is answered or an insight discovered, encourage the DS to share it with the wider team and other DSs. Try to save them somewhere that will last. This information is gold for when you are looking for new ideas. 🗣

  6. Put them in the spotlight: Encourage your DS to be the one sharing their work in meetings, presentations, brainstorms, etc. Help them get the credit they deserve for the work they do. 👏

  7. Find a balance: Don’t be data-driven — be data-informed. Use the insights from the data as one input to a decision (so critical), but leave a bit of room for other inputs beyond data. 🤔

That’s it for this week!

Inspirations for the week ahead

  1. Watch: General Magic — An inspiring, gripping, and improbable story about a small company in the ’90s influenced much of the technology we use today. It’s also an excellent case study in what happens when you lack product management. 🤪

  2. Read: Three Big Things: The Most Important Forces Shaping the World — If you love Sapiens, you’ll love this. 🤓

  3. Learn: How to Put on a Duvet Cover — Life will never be the same 🤯

Please share this newsletter with your friends if you’re finding it valuable.

And if you’d like some advice yourself, or just want to say hi, just reply to this email and ask! I’ll tackle three reader questions each week (keeping your name and company anonymous) until you quit sending me questions. I definitely won’t have all of the answers, but hey, it’s free! 🤝


Lenny 👋

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