Lenny's Written Position
The GAIN framework (Goal, Actions, Impacts, Next actions) is more effective than typical feedback because framing feedback around what someone stands to gain is more motivating than focusing on what to avoid.
Sharing observations of actions and their impacts is far more effective than making judgments, because critical judgments almost guarantee defensiveness and derail conversations.
Even flattering judgments like 'You're a rockstar PM' can destroy growth mindset and foster people-pleasing, because if success is attributed to brilliance then failure implies lack of it.
Saying 'I'm giving you these comments because I have very high expectations and I know you can reach them' more than quadrupled revision rates compared to a neutral framing.
Saying 'Feel free to say no' when making a request doubled the percentage of people who said yes, because supporting autonomy preempts resistance and engenders goodwill.
Acknowledging your own contribution to a problem before giving feedback is one of the most disarming approaches available, because it prevents the recipient from fixating on your role in the situation.
Burnout conquerors overcommunicate not just what they are working on but how they work — their boundaries, constraints, strengths, and decision-making preferences — using a 'How I Work' document.
Skip leads should never offer strong opinions or make decisions on the spot with skip reports, as this undermines their direct-report managers and creates contradictory directions.
Every team member should attend at least 50% of user research sessions because hearing a user directly express a pain point makes team members far more likely to act on it than hearing a secondhand summary.
Every successful person became successful because they were skilled at asking for help, and failing to build this muscle actively slows your career trajectory.
The fear of appearing incompetent when asking for help is usually unfounded; people rarely perceive someone as weak or burdensome when they make a thoughtful, unentitled ask.
Effective help requests follow a six-part structure: signpost, clear request, rationale, why them, timeline, and opt-in/out.
There are five distinct types of help you can seek: perspective gathering, information/knowledge, task progression, empathetic support, and advocacy.
The Trust Vault is a metaphor for how much trust your user base has in you; it can be filled and depleted, and you should measure it with periodic surveys asking users to rate how much they trust your staff to do the right thing.
Public forums are the wrong place for nuanced product discussions; instead form a private advisory council of representative users who can give candid feedback without the incentive to 'win' the conversation.
If you ask users for feedback but do not act on it, you burn more trust than if you had never asked; the golden rule is to ask for feedback only if you will genuinely consider it.
Engineers spending 20% of their time on customer support actually makes product development faster, not slower, because teams figure out what matters to customers quickly.
Podcast Moments
“When we presented Sonos, it was rejected because it's not entertainment-like. We argued about that because I said, 'This is outside looking in, but I don't see you as an entertainment company.' Humans do like to be comfortable. Part of our job here is to help people to give the confidence going bigger and being uncomfortable.”
Naming expert shares the process behind creating billion-dollar brand names like Azure, Vercel, Windsurf, Sonos, Blackberry, and Impossible Burger | David Placek (Lexicon Branding) · David Placek
“If they come to me upset, I try to focus them less on how you litigate another person's impression of you and more on what is the action that you can take to counter-program the narrative that you are afraid that this other person has of you.”
How to build a team that can “take a punch”: A playbook for building resilient, high-performing teams | Hilary Gridley (Head of Core Product, Whoop) · Hilary Gridley
“I talk about what I call the magic questions, but the thing about magic questions is they're not actually questions, they're statements and they end with, 'Do you agree?' or 'Is that right?' You're teasing out the mental model rather than asking them to explain it to you.”
How to build a team that can “take a punch”: A playbook for building resilient, high-performing teams | Hilary Gridley (Head of Core Product, Whoop) · Hilary Gridley
“The question that I often ask is how have I been complicit in creating the conditions I say I don't want. The purpose of this question is actually to evoke your own agency.”
How have I been complicit in creating the conditions I say I don’t want? | Jerry Colonna (CEO of Reboot, executive coach, former VC) · Jerry Colonna
“My number one guidance I would give to any startup founder is create a lot of opportunities for people to give you feedback inside the product. When you're building AI products, it's a constant stream of user feedback. For people thinking about not building AI products, it's going to be hard to compete with something that has such a tight feedback loop.”
Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js) · Guillermo Rauch
“You can continue to think that way and your career might be fine, but if you embrace that if you manage your boss, they're going to appreciate you much more, you're going to get more opportunities, you're going to have more trust with them.”
Become a better communicator: Specific frameworks to improve your clarity, influence, and impact | Wes Kao (coach, entrepreneur, advisor) · Wes Kao
“As you move up the triangle of the content hierarchy of BS, there's less and less room for BS. In a cohort-based course where your students are right there with you, if you're saying something that doesn't really make sense, there could be a whole conversation happening in Zoom chat.”
Become a better communicator: Specific frameworks to improve your clarity, influence, and impact | Wes Kao (coach, entrepreneur, advisor) · Wes Kao
“When you're talking to someone and explaining something, there's usually a moment where their eyes light up because they are genuinely interested. Make note of those moments because their face can't lie. Cut out all the parts that make people go dead in the eyes.”
Become a better communicator: Specific frameworks to improve your clarity, influence, and impact | Wes Kao (coach, entrepreneur, advisor) · Wes Kao
“You have to deliberately not act on the feedback of many of your early users, and this is at the same time as listening to people intensely and building what people want. That's what we're here to do, is to make something that people want, but it can't be all people.”
Superhuman's secret to success: Ignoring most customer feedback, manually onboarding every new user, obsessing over every detail, and positioning around a single attribute: speed | Rahul Vohra (CEO) · Rahul Vohra
“Hope for the future is so important. I know this is going to be challenging for you to hear, not going to promote you, but I want you to know this. It's really important to me that you're able to succeed in your career here.”
Scripts for difficult conversations: Giving hard feedback, navigating defensiveness, the three questions you should end every meeting with, more | Alisa Cohn (executive coach) · Alisa Cohn
“They're trying now to be the leader who everyone loves, but what really needs to happen very often is, we need to drive towards results. This employee continuing to not really do a great job, you don't want to push them because you don't want to upset them. Ultimately, that leads to the demise of your company.”
Scripts for difficult conversations: Giving hard feedback, navigating defensiveness, the three questions you should end every meeting with, more | Alisa Cohn (executive coach) · Alisa Cohn
“When someone gets defensive, don't match their energy. Say: 'I can see this is hard to hear. I want to give you a moment. We can come back to this.' That pause is incredibly powerful.”
Scripts for difficult conversations: Giving hard feedback, navigating defensiveness, the three questions you should end every meeting with, more | Alisa Cohn (executive coach) · Alisa Cohn
“The best script for hard feedback is SBI: Situation, Behavior, Impact. Here's the situation, here's the behavior I observed, here's the impact it had. It removes the judgment and makes it about observable facts.”
Scripts for difficult conversations: Giving hard feedback, navigating defensiveness, the three questions you should end every meeting with, more | Alisa Cohn (executive coach) · Alisa Cohn
“I use AI to essentially do a voice-of-the-customer pipeline automatically. It processes all customer calls, tags them with themes, and then I can go pull up exactly what people said about a given topic.”
Unorthodox PM wisdom: Automating user insights, unselling job candidates, logging every decision, more | Kevin Yien (Stripe, Square, Mutiny) · Kevin Yien
“Yes, you are a data scientist, but your goal is to figure out what's happening. And if that means that you're going to pick up the phone and call customers, then that is what you're going to do to roll up your sleeves.”
Building a world-class data org | Jessica Lachs (VP of Analytics and Data Science at DoorDash) · Jess Lachs
“The moment the customer felt compelled enough to go out of their way to talk about some problem, that's an unbelievable gift. I will leave a meeting to just get one message back to them.”
Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead) · Jeff Weinstein
“We show up four to eight people total pretend to be some company with some outcome problem. Rule one is you do not work at Stripe and rule two is we're not here to solve any problems. This is just about practicing empathy for the customer.”
Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead) · Jeff Weinstein
“Curiosity is a superpower in product. When someone says something you disagree with, instead of arguing, try saying 'fascinating, tell me more.' You will learn things you never expected.”
Making an impact through authenticity and curiosity | Ami Vora (CPO at Faire, ex-WhatsApp, FB, IG) · Ami Vora
“People think asking for what they want is selfish. But actually, when you're clear about what you need, you make it easier for everyone around you. Ambiguity is what creates conflict.”
Why not asking for what you want is holding you back | Kenneth Berger (exec coach, first PM at Slack) · Kenneth Berger
“At Slack, one of the things I learned was that the best product decisions came from people who were willing to say what they actually thought, even when it was uncomfortable. The culture rewarded directness.”
Why not asking for what you want is holding you back | Kenneth Berger (exec coach, first PM at Slack) · Kenneth Berger
“I feel that you don't care and I feel you're being insensitive are not feelings, and that's where we make our biggest mistakes when it comes to feedback.”
How to build deeper, more robust relationships | Carole Robin (Stanford GSB professor, “Touchy Feely”) · Carole Robin
“Questions that start with what, when, where, how. Stay away from why.”
How to build deeper, more robust relationships | Carole Robin (Stanford GSB professor, “Touchy Feely”) · Carole Robin
“We don't understand that we are only privy to two out of the three, so I know what's going on for me and I know what I did. I have no idea what happened on your end.”
How to build deeper, more robust relationships | Carole Robin (Stanford GSB professor, “Touchy Feely”) · Carole Robin
“Anger is a secondary emotion. Really what's going on is you're afraid or you're hurt.”
How to build deeper, more robust relationships | Carole Robin (Stanford GSB professor, “Touchy Feely”) · Carole Robin
“The most robust relationships are the ones that have been through conflict and survived. If you've never had a hard conversation with someone, you don't actually have a deep relationship. You have a pleasant one.”
How to build deeper, more robust relationships | Carole Robin (Stanford GSB professor, “Touchy Feely”) · Carole Robin
“If you say, 'Do you have any feedback for me?' You're wasting your breath. The other person's going to say, 'Oh no, everything's fine.' The question that I like to ask is, 'What could I do or stop doing that would make it easier to work with me?'”
Radical Candor: From theory to practice with author Kim Scott · Kim Scott
“Do not write down my question because if you sound like Kim Scott and not like yourself, then other people are not going to believe you want the answer. It needs to sound authentic to you.”
Radical Candor: From theory to practice with author Kim Scott · Kim Scott
“If everybody can write down their question, who they're going to ask it of and then pop it into their calendar right now, this will be one of the most productive podcasts in all of podcast land.”
Radical Candor: From theory to practice with author Kim Scott · Kim Scott
“It's knowing that, oh, there's a human, they know I care about them. So when the feedback is coming like raw, they know that it's in their best interest because I've shown enough times that I genuinely care about the person behind the role.”
Crafting a compelling product vision | Ebi Atawodi (YouTube, Netflix, Uber) · Ebi Atawodi
“If you give me feedback, I'll be like, 'Hey, thank you so much. This is super helpful,' because people are like, 'Oh, he actually likes the feedback.' Now, inside my heart might be melting. I'm like, 'Oh, I thought I got better at this.' But externally, I'm like, 'Hey, thank you,' and I mean it. I think that's the key that most people don't focus on. And if you get more feedback, then you'll just get better at the things.”
Leveraging mentors to uplevel your career | Jules Walter (YouTube, Slack) · Jules Walter
Cutting Room Floor
Guest insights on this topic that Lenny hasn't (yet) written about in his newsletters. Potential material for future posts.
“As you move up the triangle of the content hierarchy of BS, there's less and less room for BS. In a cohort-based course where your students are right there with you, if you're saying something that doesn't really make sense, there could be a whole conversation happening in Zoom chat.”
Become a better communicator: Specific frameworks to improve your clarity, influence, and impact | Wes Kao (coach, entrepreneur, advisor) · Wes Kao
“When you're talking to someone and explaining something, there's usually a moment where their eyes light up because they are genuinely interested. Make note of those moments because their face can't lie. Cut out all the parts that make people go dead in the eyes.”
Become a better communicator: Specific frameworks to improve your clarity, influence, and impact | Wes Kao (coach, entrepreneur, advisor) · Wes Kao
“Hope for the future is so important. I know this is going to be challenging for you to hear, not going to promote you, but I want you to know this. It's really important to me that you're able to succeed in your career here.”
Scripts for difficult conversations: Giving hard feedback, navigating defensiveness, the three questions you should end every meeting with, more | Alisa Cohn (executive coach) · Alisa Cohn
“They're trying now to be the leader who everyone loves, but what really needs to happen very often is, we need to drive towards results. This employee continuing to not really do a great job, you don't want to push them because you don't want to upset them. Ultimately, that leads to the demise of your company.”
Scripts for difficult conversations: Giving hard feedback, navigating defensiveness, the three questions you should end every meeting with, more | Alisa Cohn (executive coach) · Alisa Cohn
“When someone gets defensive, don't match their energy. Say: 'I can see this is hard to hear. I want to give you a moment. We can come back to this.' That pause is incredibly powerful.”
Scripts for difficult conversations: Giving hard feedback, navigating defensiveness, the three questions you should end every meeting with, more | Alisa Cohn (executive coach) · Alisa Cohn
“I use AI to essentially do a voice-of-the-customer pipeline automatically. It processes all customer calls, tags them with themes, and then I can go pull up exactly what people said about a given topic.”
Unorthodox PM wisdom: Automating user insights, unselling job candidates, logging every decision, more | Kevin Yien (Stripe, Square, Mutiny) · Kevin Yien
“Yes, you are a data scientist, but your goal is to figure out what's happening. And if that means that you're going to pick up the phone and call customers, then that is what you're going to do to roll up your sleeves.”
Building a world-class data org | Jessica Lachs (VP of Analytics and Data Science at DoorDash) · Jess Lachs
“We show up four to eight people total pretend to be some company with some outcome problem. Rule one is you do not work at Stripe and rule two is we're not here to solve any problems. This is just about practicing empathy for the customer.”
Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead) · Jeff Weinstein
“At Slack, one of the things I learned was that the best product decisions came from people who were willing to say what they actually thought, even when it was uncomfortable. The culture rewarded directness.”
Why not asking for what you want is holding you back | Kenneth Berger (exec coach, first PM at Slack) · Kenneth Berger
“We don't understand that we are only privy to two out of the three, so I know what's going on for me and I know what I did. I have no idea what happened on your end.”
How to build deeper, more robust relationships | Carole Robin (Stanford GSB professor, “Touchy Feely”) · Carole Robin
“Anger is a secondary emotion. Really what's going on is you're afraid or you're hurt.”
How to build deeper, more robust relationships | Carole Robin (Stanford GSB professor, “Touchy Feely”) · Carole Robin
“Do not write down my question because if you sound like Kim Scott and not like yourself, then other people are not going to believe you want the answer. It needs to sound authentic to you.”
Radical Candor: From theory to practice with author Kim Scott · Kim Scott
“If everybody can write down their question, who they're going to ask it of and then pop it into their calendar right now, this will be one of the most productive podcasts in all of podcast land.”
Radical Candor: From theory to practice with author Kim Scott · Kim Scott