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Rachel Lockett

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2025-11-23
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2025-11-23
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  1. Well, I'm going to give you an example of a client. I'm going to call him Jeff, who runs an AI company. And he was essentially playing the role of the head of product also. And he had a growing number of engineers and designers. And his customer base was growing rapidly. Started to feel completely overwhelmed. So he came to me and we started coaching together. And soon he realized that he was the blocker on every decision, every business decision, every product decision, and he was resenting it. He wanted his team to take more ownership. But with some coaching, he realized he was training his team to come to him with every decision because he had always operated that way. Decided to create squats and have small pods of engineers, product leaders, and designers focus on subsets of the team. Very normal as you have a small startup scaling.

    2025-11-23 · Lenny's Podcast · A guide to difficult conversations, building high-trust teams, and designing a life you love | Rachel Lockett · IDENTIFIED FROM THE TRANSCRIPT · source

  2. This actually happens to me all the time in talent conversations because I have a background in being in HR business partner and I'm working with CEOs and they're thinking about building their leadership team and I want everyone to have a very rigorous stance on their talent because if you have an A plus squad, you're going to do great things in the world. And sometimes they come up with an idea to performance manage someone who's clearly not working in the role, but think, oh, maybe I'll wait six months and then we'll have a conversation. I have a strong point of view. I'm not going to let that slide, but I'm going to say, help me understand why that is a good idea. And I'm going to press on that. And if they don't come to an idea that I'm aligned with, I'm going to share openly my perspective while still empowering them to solve their own problem.

    2025-11-23 · Lenny's Podcast · A guide to difficult conversations, building high-trust teams, and designing a life you love | Rachel Lockett · IDENTIFIED FROM THE TRANSCRIPT · source

  3. Yeah, and the other thing that does when you're curious and you don't just shut down someone's idea is you're helping them think. You're not helping them realize they're going to screw it up unless they come to you for advice. You're helping equip them with the right questions to ask and the right skepticism to have. And so it's always useful to be in conversation when someone who reports to you has a different worldview than you do. There's some reason they came up with this great idea that you think is a terrible idea. And actually that's where the learning happens.

    2025-11-23 · Lenny's Podcast · A guide to difficult conversations, building high-trust teams, and designing a life you love | Rachel Lockett · IDENTIFIED FROM THE TRANSCRIPT · source

  4. Yeah, okay, I think that's great. So if you have a really strong negative reaction to what they're sharing, of course, it doesn't behoove anyone to hide that. I think you get curious, hey, tell me understand how you came to that conclusion because here's my reaction to that. So you're honest, but you're also curious. So coaching in a manager or a leader context is not the same as in an executive coaching conversation. You're managing this person. You're responsible for their outcomes.

    2025-11-23 · Lenny's Podcast · A guide to difficult conversations, building high-trust teams, and designing a life you love | Rachel Lockett · IDENTIFIED FROM THE TRANSCRIPT · source

  5. Yeah, this is definitely you want a coach when you think the person you're talking to has the right context and can solve their own problem. That's a premise of coaching. You wouldn't coach if someone needs your guidance and comes to you and says, hey, I'm trying to take my company public. You took your company public. Can you tell me exactly the steps you took to get there? Not a good time to coach.

    2025-11-23 · Lenny's Podcast · A guide to difficult conversations, building high-trust teams, and designing a life you love | Rachel Lockett · IDENTIFIED FROM THE TRANSCRIPT · source

  6. And once they start talking about their reality and where they're stuck, then they realize, oh, I'm stuck because my cross-functional partner is blocking me and I don't have any relationship with them. I need to go meet with them, actually, and just have a breakthrough conversation, tell them where I'm stuck. So sometimes talking this out loud, just creating that space for them is going to help them tremendously.

    2025-11-23 · Lenny's Podcast · A guide to difficult conversations, building high-trust teams, and designing a life you love | Rachel Lockett · IDENTIFIED FROM THE TRANSCRIPT · source

  7. Exactly right, and you don't have to do it in this order. These are just four kinds of questions. So you might come and someone's super clear about their outcome. You know that. You don't need to spend any time asking them questions about that. Maybe you just want to really dig in on where they stuck.

    2025-11-23 · Lenny's Podcast · A guide to difficult conversations, building high-trust teams, and designing a life you love | Rachel Lockett · IDENTIFIED FROM THE TRANSCRIPT · source

  8. The R in the grow model is about your current reality. Where are you stuck? What are your current challenges? What have you tried? The O is about your options. So let's expand the opportunities that you can understand of the choices you have in front of you. What are the various paths you could take? And the W in the Grow model is the way forward. What are you going to do next? So this sounds simple. And it is simple if you take the time and space to listen carefully and ask any of these questions. The people on your team will appreciate the space and time to unlock an option that they didn't think of before and walk away with a concrete next step.

    2025-11-23 · Lenny's Podcast · A guide to difficult conversations, building high-trust teams, and designing a life you love | Rachel Lockett · IDENTIFIED FROM THE TRANSCRIPT · source

  9. Yes. So that's listening. Second skill, powerful questions So asking powerful questions means I'm curious about what's really going on. And there's not one right answer. So a powerful question helps you gain insight and it takes you to a new solution set you didn't have before. It's not me leading the witness. I'm not trying to guide you to a specific answer. That wouldn't be a powerful question. So, something that I like to equip leaders with is four kinds of questions. You can ask to unlock insight. So, the first kind is I use a grow model. So the grow model just is four different categories of kinds of powerful questions. So the G in Grow is goal. So what does success look like? What's the outcome that you want to have? Any question that's around defining the best case scenario

    2025-11-23 · Lenny's Podcast · A guide to difficult conversations, building high-trust teams, and designing a life you love | Rachel Lockett · IDENTIFIED FROM THE TRANSCRIPT · source

  10. And even things that I'm guessing, and I can say, is that right? And you can say, no, actually, I'm not conflicted about the challenges of being a dad. I just am so joyful. And then now I understand where you're coming from, and so do you.

    2025-11-23 · Lenny's Podcast · A guide to difficult conversations, building high-trust teams, and designing a life you love | Rachel Lockett · IDENTIFIED FROM THE TRANSCRIPT · source

  11. Great. Yeah, there's an element of synthesizing what I'm hearing verbally. That's the focus listening part. And then mirroring back the emotions that I'm noticing.

    2025-11-23 · Lenny's Podcast · A guide to difficult conversations, building high-trust teams, and designing a life you love | Rachel Lockett · IDENTIFIED FROM THE TRANSCRIPT · source

  12. Yeah, there's some emotional connection when you listen actively. And that took less than a minute. So, what I want to invite listeners to understand is that active listening doesn't mean you're setting up an hour coaching session with every person on your team. No one has time for that. But even in the time you're already spending, just focusing on the other person in a way that is novel and really gives them their full attention so you can see their feelings under what they're saying goes a long way to motivating your team and helping them understand what's actually happening under the surface in this situation.

    2025-11-23 · Lenny's Podcast · A guide to difficult conversations, building high-trust teams, and designing a life you love | Rachel Lockett · IDENTIFIED FROM THE TRANSCRIPT · source

  13. Yeah. And I see you when you talk about being a father. Initially, I saw you really squirm in your chair. Like, whoa, this is a big question. And, you know, you looked up and down and kind of avoided my eye contact at first because my sense is you love being a dad and it's so challenging. It's so tiring. And I'm hearing both of that in your answer, like the high joy and the discomfort in having to sleep train and having to disappoint and navigating challenging behavior.

    2025-11-23 · Lenny's Podcast · A guide to difficult conversations, building high-trust teams, and designing a life you love | Rachel Lockett · IDENTIFIED FROM THE TRANSCRIPT · source

  14. Okay, how about this? I'll demonstrate some level three listening. I'm going to ask you a question. Told me earlier you're a father. Is it like to be a dad?

    2025-11-23 · Lenny's Podcast · A guide to difficult conversations, building high-trust teams, and designing a life you love | Rachel Lockett · IDENTIFIED FROM THE TRANSCRIPT · source

  15. Level 3 lessening is global listening. So that's when I'm hearing beneath the words and hearing what you're communicating, not just what you're saying. I see your body language. I notice your tone of voice. I know the context around what you're talking about. And I can reflect back more insight about what's happening than you're aware of because I'm understanding everything you're communicating. So dropping into level three listening is what great leaders do when they're influencing, when they're selling, when they're pitching a vision, and definitely when they're coaching. Do you want to try it

    2025-11-23 · Lenny's Podcast · A guide to difficult conversations, building high-trust teams, and designing a life you love | Rachel Lockett · IDENTIFIED FROM THE TRANSCRIPT · source

  16. This is rampant in tech and great leaders flipped that script and tune in. They're the kinds of leaders who walk into a room and they can see the elephants. They can name them. They can ask the hard questions to get people collaborating. So there's actually three levels to listening. So the first level, listening level one is internal. Let's say you're talking to me about a problem. I'm thinking about the implications of that problem on me. I'm completely distracted with my own inner dialogue. That's level one. Most people go through their world, rushed, and in level Level two listening is focused. So you're talking to me and I can repeat back what you're saying. So I am listening to the words you're describing. And that's typically what happens in a good one-on-one. We're problem solving together. I'm focused on your words.

    2025-11-23 · Lenny's Podcast · A guide to difficult conversations, building high-trust teams, and designing a life you love | Rachel Lockett · IDENTIFIED FROM THE TRANSCRIPT · source

  17. Okay, so the first skill is active listening. And Lenny, you're probably a good listener because this is what you do for a living is you listen to the people who come on your podcast. But I don't know if you've seen Fight Club. There's a quote most people aren't listening. They're just waiting for their turn to talk

    2025-11-23 · Lenny's Podcast · A guide to difficult conversations, building high-trust teams, and designing a life you love | Rachel Lockett · IDENTIFIED FROM THE TRANSCRIPT · source

  18. Yeah, it's an urgent issue, and you actually have an answer that you want to drive. So don't coach and make it a game. Like, you want your person on your team to guess what's in your mind. That's not a good time to coach. You have something you absolutely want them to do. You know the right answer. You want them to be motivated to go do it. Advise them. Help them see the path. But most leaders over index on that solution. So I want to share. Maybe Lenny, I can teach you two skills that I think are the basics of leader coaching that you can use in your own life tonight with your wife. She's going to love this. And hopefully your listeners can use them too.

    2025-11-23 · Lenny's Podcast · A guide to difficult conversations, building high-trust teams, and designing a life you love | Rachel Lockett · IDENTIFIED FROM THE TRANSCRIPT · source

  19. Yeah, that's a great analogy. I love that. I think leaders make things up when they don't have answers sometimes. Person comes to you with a problem and you just want to help. But the best way to help is actually doing something that most leaders don't do well. It's attuning to what is the context? What does this person need? What are they blocked on? And ask them with those questions so that they can solve their own problem.

    2025-11-23 · Lenny's Podcast · A guide to difficult conversations, building high-trust teams, and designing a life you love | Rachel Lockett · IDENTIFIED FROM THE TRANSCRIPT · source

  20. So coaching is actually a learnable skill, obviously, because there's tons of coaches around Silicon Valley, but you don't have to coach in the same way that an executive coaches. You can shift your energy into curiosity when someone brings you a hard problem to solve and create space to get curious and help them solve their own problem. So obviously sometimes advising is the right path. If there's an urgent issue, the person coming to you doesn't have the skill they need. That's a time to advise and help. Leaders over rotate, assuming the people that they've hired who are experts in their domain need them to solve the problem. So I think it's useful for your listeners to actually know that coaching's an alternative and I can help them learn some basic skills around this.

    2025-11-23 · Lenny's Podcast · A guide to difficult conversations, building high-trust teams, and designing a life you love | Rachel Lockett · IDENTIFIED FROM THE TRANSCRIPT · source

  21. But great leaders know that when you try to advise and have the answer all the time, you're not actually equipping your team to go solve the hard problems. You're training your team to come to you with all of the hard problems. Coaching is a different way. It's an alternative path that unlocks brilliance in your team and is way more motivating for the people around you.

    2025-11-23 · Lenny's Podcast · A guide to difficult conversations, building high-trust teams, and designing a life you love | Rachel Lockett · IDENTIFIED FROM THE TRANSCRIPT · source

  22. Think that most leaders, especially technical leaders, assume they have to have all the answers. Have climbed the ladder in whatever realm they're in because they've been dependable, reliable, the smartest person in the room. When you're leading a quickly scaling company, you quickly have less context than the people you're around. And the way you were operating before doesn't work because you don't have the ability to wrap your arms around every problem in a deep way. So I've seen leaders at every phase from frontline managers up to running an 8,000 person company struggle with knowing when do I have to have the answer and when I don't have the answer, what options do I have?

    2025-11-23 · Lenny's Podcast · A guide to difficult conversations, building high-trust teams, and designing a life you love | Rachel Lockett · IDENTIFIED FROM THE TRANSCRIPT · source

  23. It's the largest Ethereum L2 in the world, and it's a community of creators and developers. And he is having a great time, like he's having more fun than ever. And so I think for the people who are committed to excellence and impact, recognizing that if they lean into their gifts and they get back into their purpose, they can have more fun while having an impact on the world.

    2025-11-23 · Lenny's Podcast · A guide to difficult conversations, building high-trust teams, and designing a life you love | Rachel Lockett · IDENTIFIED FROM THE TRANSCRIPT · source

  24. A client I've seen for 10 years, and he's a person who exemplifies a commitment to personal growth. I started working with him when he was a frontline engineering manager at Coinbase. And we talked about who he is, what his strengths are, and his bigger picture why. And he talked about this dream of creating a global movement one day. He was really focused on building community and he thought the path for creating possibility in the world around him was creating a strong community around him. And he continually worked on his leadership capacity. And over the 10 years, at some point, he created a tattoo on his arm that's a son with a redwood grove around it that reminded him of his core strengths and his purpose. And today, guess what he's doing, Lenny?

    2025-11-23 · Lenny's Podcast · A guide to difficult conversations, building high-trust teams, and designing a life you love | Rachel Lockett · IDENTIFIED FROM THE TRANSCRIPT · source

  25. Yeah, that's true. I mean, it's vulnerable to seek help, but I think your audience, I know to be incredibly committed to growth, I hear people who come on your podcast and they've spent decades focused on self-improvement. And I actually want to tell you a story about one of my clients who loves your podcast and I was talking to him last week.

    2025-11-23 · Lenny's Podcast · A guide to difficult conversations, building high-trust teams, and designing a life you love | Rachel Lockett · IDENTIFIED FROM THE TRANSCRIPT · source

  26. Yes, exactly. It is achievable, and it's actually most natural. Want to care about the people they work with? They want to empower those around them, but sometimes the busyness of our world gets in the way and the urgency of the litany of things to do distracts you from the people in front of you. And actually, if you really understand the talent around you and you create an environment where they can be successful, your business will thrive.

    2025-11-23 · Lenny's Podcast · A guide to difficult conversations, building high-trust teams, and designing a life you love | Rachel Lockett · IDENTIFIED FROM THE TRANSCRIPT · source

  27. Genuinely, I hope that your listeners take away that the human side of business building is incredibly fun and impactful and that it's easy to do. They can do it with simple tools. So I'm hopeful that through this conversation, heads of product, heads of engineering, founders, walk away feeling more empowered and more motivated to attune to the people around them

    2025-11-23 · Lenny's Podcast · A guide to difficult conversations, building high-trust teams, and designing a life you love | Rachel Lockett · IDENTIFIED FROM THE TRANSCRIPT · source

  28. When people are in their gifts and their strengths, they have more energy. We all have more energy when we're operating from the things we naturally are good at. It's no one else's job to help you live in your gifts. What I notice in big companies is people are often annoyed or frustrated with their management for not making their job more interesting. No, your manager's job is to help you perform in the job you are hired to do. It's your job to navigate your career.

    2025-11-23 · Lenny's Podcast · A guide to difficult conversations, building high-trust teams, and designing a life you love | Rachel Lockett · IDENTIFIED FROM THE TRANSCRIPT · source

  29. We operate in tech, like we're supposed to give all of ourselves, all of our time, all of our energy to this endeavor. And it's purely logical. That's not at all true. It's completely emotional. Professionals have feelings. People, when they want to have a conflict, they come in ready to prove their point. There's a misguided view that the goal is to convince the other person that what they're doing is wrong. Actually, the goal of any conflict is to create mutual understanding.

    2025-11-23 · Lenny's Podcast · A guide to difficult conversations, building high-trust teams, and designing a life you love | Rachel Lockett · IDENTIFIED FROM THE TRANSCRIPT · source

  30. Most leaders, especially technical leaders, assume they have to have all the answers. People have climbed the ladder because they've been dependable, reliable, the smartest person in the room. But great leaders know that when you try to advise and have the answer all the time, you're not actually equipping your team to go solve the hard problems. You're training your team to come to you with all of the hard problems.

    2025-11-23 · Lenny's Podcast · A guide to difficult conversations, building high-trust teams, and designing a life you love | Rachel Lockett · IDENTIFIED FROM THE TRANSCRIPT · source