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Rachel Lockett

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130
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2025-11-23
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2025-11-23
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  1. Yeah, find me at locketcoaching.com. And how can listeners be useful? Listeners should turn towards each other, build great relationships, and send CEOs and co-founders my way if they need coaching.

    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. My gosh. So, my daughter is really into Roll Dahl. Love roll dog because he's completely irreverent and he has a crazy imagination. So we've been reading witches, Matilda, all of his books. And both my kids love it. So they're five and seven.

    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. I have a quote that is on my desk, and I love it. Ready? If you can see your path laid out in front of you step by step, it's not your path. Own path you make with every step you take. That's why it's your path. That's the Joseph Campbell quote.

    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. Been recording trainings on Loom for some of my clients that are, it's a scaled holding company. So I'm able to scale training in a really human connected way.

    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. Oh god, I just went to Kpop Demon Hunters with my daughter. It's so embarrassing. But that's what we dress as for Halloween, like everyone else in 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

  6. Want to share is that the world is getting more lonely. A lot of research on this, but it's also obvious in my coaching sessions that people feel more alienated from one another. And actually building businesses is an inherently human endeavor. So I'm a fan of this AI boom. I appreciate that we have more technology at our fingertips than ever before. Want to encourage listeners to Think of themselves as leaders who bring humans together to self actualize, and that they have to actively overcome the default state, which is blind, grind, and loneliness. So I think this is a call to action for your listeners to connect with the people around them, lead healthier teams, create environments where connection is inevitable, and that they will have more fun and build better businesses because of that.

    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. So that they can access between just some extra spot support. They're going to this conversation. How should they approach it? They're anxious about this team meeting. How can they make the most of it? More tactical support. I see personal coaching as Still critical for what is your vision of your life? How do you want to shift your core behavior to align with that vision? But that AI can play a real helpful role in between on the tactics.

    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. Finally, and I'm experimenting with AI in a way to support my clients between sessions. So I've gotten some feedback from my clients that they would like more interaction between our sessions. And they're always allowed to email me or text me. I'm available to them. But I think they want to be really respectful of my time. And so some people do reach out and ask me questions and other people wait for our session. So I'm curious about the future of coaching, how in between sessions clients can get access to more of an AI support where they, the bot has all of their context, their development plan that we created at the beginning. So that's their goals for our work together, how they want to grow. Some of my core frameworks and my beliefs and my training and the granola notes from all of our sessions.

    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. Secondly, I use, I just use ChatGPT to help me plan my retreats. I run a women's organization, and we have eight retreats a year. And it's a great tool to think expansively about new activities once I've gotten the core objectives down and I have a bunch of ideas about what I want to do. It gives me new creative ideas. So I can put in like, here's my objective, here's my goal, here's my audience, here's my last retreat that I ran. I kind of want three new ideas for this session. So it'll give me kind of creative energy that I otherwise would need to get together with other coaches to discuss. And I do that 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

  10. There you go. So I use granola to take notes in our session so I can be fully present with my clients. And I can give them a synthesis of what happened and the next steps they committed to after our session. Also, use it. I put them in a folder for every client, and so I can look at insights across our work together. What are the deeper things that are happening? What are the patterns that are taking place? I have these in my head, but actually it's a great tool to see over time, oh yeah, we talked about that in our first session. Let's bring that back because that's what you're So it helps me create the kind of transformation that I want for all my clients.

    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. Yeah, it's a great question. So as a coach, I use AI in a couple key ways that I'm grateful for. One, I use granola, which I saw you give away to your listeners.

    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. So, around this one page plan, the reason I like a rhythm is you can kick off the year with the plan. That's really simple, easy to understand. Everyone can have it accessible. And every quarter you can get together to reflect what worked, what didn't work. I really like the question, what's an inconvenient truth? Are the things that need to be talked about, that no one's talking about because you're too busy. That's the power of combining a simple plan, whether it's one page or not, that aligns you from the top to the bottom, your vision all the way down to your quarterly goals. And a time where you stop, pause, discuss, reflect, have a little spacious energy. It's not unlike what you said about your own time. You are the executive team. You want a little bit of spacious time to tinker, reflect.

    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. When do you come together to kick off the year and share your strategy and vision again and talk about the goals? When you come together to reflect on what's working and not working, and how do you do that? And in what groups? And are you honest or are you just kind of doing it as a quick exercise to move on to what's pressing? So just like I said in co-founder dynamics, a key is to step out of the dance floor and to get onto the balcony. Executive teams leading a complex business need time away from being in the business to work on the business.

    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. Yeah, what I see is clarity and alignment. And I also see more connection. So I want to name that it's not just about having a plan, it's about how you create it, how you reflect on it, and how you come together around it to celebrate wins. So in my opinion, a very underattended to part of building a business is an operating rhythm.

    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. And I love how they instituted that with their portfolio. And I saw the power of it. They've collected some data that their portfolio companies that actually institute the people first operating rhythm result in higher returns. So they're very committed to this strategy. And after operating with CEOs in their rhythm, I took some of those ideas and started to help other founders and other leaders with some of the same concepts in my own way.

    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. So I actually got this idea of the one page plan from Alpine Investors. They do a something called the People First Operating Rhythm, and they successfully implemented that at their portfolio companies. And I work in concert with Alpine, so I work with some of their portfolio CEOs to execute this rhythm. So it's not just about a one-page plan. It puts your vision and your values on the first column, your strategic intentions, and your KPIs on the second column, your annual goals on the third, and your quarterly goals on the fourth, so that no matter what you're talking about in terms of what are we doing for the next year or the next quarter, how do we prioritize, it's always in tandem with your core KPIs, your strategy, and your vision.

    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. Yeah, thanks for asking that question. I think typically companies have. Complicated the process of aligning their vision, their strategy, their goals, and the way people behave with each other, their values, so that all of these things live in different places, are talked about to a different degree, resonate to employees differently. And if you asked anyone at the company, what are your top three priorities and how do they relate to the vision? It's not an easy answer. So, the reason I like the one page plan concept is it's simplifying. It's a way for the leadership team to come together and align around what are we doing here? What is our role in it? And how do we communicate it so that the whole company has clarity and knows how the work they're doing ladders up to our big picture vision that we're all committed to?

    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, and I wanted to just, I want to make a distinction between that. What we talked about earlier, which was lean into your strengths. Because I don't believe people should suffer through the day grinding doing work that's depleting. That's not a learning opportunity. Inner personally, when you're avoiding something, it's because you care about something, avoiding your emotions is what I want to encourage people against. We have to feel our feelings all the way through, be present to our feelings, and interact with others in a way that acknowledges our feelings. That's what I want to encourage. Because actually that's not deadening. That's enlivening. And there's learning there.

    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. My perspective, you know, I talked at the beginning about how I'm obsessed with the human side of business building and my belief is that talent and the environment that you put your talent in is everything. Yes, building a product in a business is about building something that users need. It's about product market fit and then the wave you're on, timing is important, right? You're going to build a different size business if you're in a sector that's not growing. Then right now, if you're in the middle of AI. True. You're writing a timing wave and you're solving a core need. But everything besides that is so human. It's about talent and it's about the environment. So you need to create the conditions such that your talent can 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

  20. Yeah, I think that also it depends on the stage of business you're in. So, I see a lot of companies build a leadership team. And then a year later, the size and stage of their business is dramatically different. And they start to realize, oh, the CFO that was really fine back then is now completely wrong. He should be the controller. Okay, great. So reckon with that, like recognize that in how you're interacting with your current CFO, put out a search. Like there's many things you can do that aren't firing someone, but in quickly scaling businesses, it's natural that the leadership team's job will change and that you'll have to make some evolution over time.

    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. Exactly. It's very clarifying because it's binary. People have a physical sense, just like we talked about a full body, yes, before. You have a immediate reaction that is honest to that question, that provides clarity.

    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. They realize, I asked them, would you enthusiastically rehire this person for the same role? Which is the question we always ask at Stripe. And when the answer is no to that, no matter how many difficult conversations you have, this is not going to work. So then you have to take action. And even engaging in the hard conversation and seeing what happens can lead you to the clarity that you need to take action on talent that's not working.

    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. Love that. Yeah, it's like, what's important here? What do I have to learn here is a question you can ask yourself. You're avoiding something. I often see this in talent management situations. A CEO has an underperforming COO. Avoiding a conversation because they keep getting let down, and actually, they kind of know deep down this is not working out. Want to face it, it's too much work, they need to just keep plowing forward. And when we really take space to think about their feelings and needs,

    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. Maybe you don't tattoo NBC. It doesn't have a good acronym, you know, just print it out and put it right next to your screen or something. All right. All right.

    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. And so that's the instigator to know okay, I need to talk to this person. We need to clear this up. For example, I was working with a CEO whose co-founder was constantly undercutting his decisions and criticizing him. And there was something happening where they'd gone from being this great dynamic duo fundraised, hired a few leaders, and then all of a sudden he was getting kind of daggers thrown at him all the time. And it was exhausting and frustrating and confusing. So that was a time where he used NBC to address what is happening here. And it turned out that the co-founder was really frustrated with how he was spending his time. He didn't want him to be off selling. He wanted him to be helping him with product vision. And they had a totally different conception of how the CEO should be spending his time.

    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. Yeah, no, I think that's a great framework for when you want to go interact with someone around something that's not working for you. I think typically a difficult conversation arises because some feelings are coming up for you and you have a need that's not being met.

    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. And I see many leaders when they're in a challenging interpersonal conflict, being in victimhood, being in blame, or being in hero, I'm just going to do it for them and forget it. They're having such a hard time getting this done. I'm just going to do it. Instead, take responsibility for your part. What is my peace in making this dynamic happen? And how can I address 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

  28. There is always something that we're doing. So entering any conflict conversation with humility and curiosity about the other person's experience is critical to setting the table for Commitment to come out better and stronger. So no model, NVC or otherwise can fix a person who's coming in rigid and full of blame. I really love the 15 commitments to conscious leaders. I don't know if you know that book, but one of the concepts is about taking 100% responsibility. Not being in the world of blame, being a victim, or being a hero.

    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. And there's something to learn from it. So first, I want leaders who are listening to think, this is hard because I have something to learn here and because it matters. So instead of avoiding it and running away, I'm going to lean into this moment. And I'm going to come out of it, not just having solved this dynamic and not just having said my piece, but having built a skill. Reason I focus on interpersonal dynamics is because the quality of our relationships determines the quality of our life. I really believe that. And if you cannot have conflict, you can't have healthy relationships. We are going to disagree with the people we love or care about or are building a business with First, I just want listeners to reframe ambivalence and interpersonal challenge to Think of them as a growth opportunity. Second

    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. Yeah, well, first of all. Difficult conversations makes you want to run away. The marketing on conflict is poor. I want to reframe that. My belief is when we feel internally ambivalent, we have two inner parts at war. And there's something really beautiful and important to pay attention to. There's something to learn when we have ambivalence. We are in conflict, something important is at stake. We care deeply about what we're building, about the person that's letting us down. So the reason it's hard is because there's such an emotional component to 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

  31. Exactly. If you can say, I feel like even if you add like or I feel that, you're probably going to add a fact. It should be an emotion word after I feel.

    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

  32. Yes, and I want to make one note I forgot to say, which is feelings are emotions. So sometimes people say things like, I feel like you're being a jerk. That's not a feeling, obviously. A feeling is a sensation in your body that results in an emotion. So naming a feeling is actually not easy for technical leaders sometimes. I want to make that point because emotions are what get you to the underlying humanity of connection. Emotions are the key to soliciting empathy.

    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

  33. That's exactly right. And sometimes the other personals will hear that and have a different story or different perspective, right? So they might say, okay. I can honor that request, or I hear that request, and I hear your feelings, but let me explain what happened for me. And one way you could do that is, are you open to hearing that? So they're able to share their side too. You don't have to just agree with the person's request. As long as you're setting this tone, the other person's more likely to contribute in a way that achieves mutual understanding because they're going to share, once you're vulnerable, they're going to share their vulnerability.

    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

  34. Exactly. It also acknowledges that professionals have feelings. I think that 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. And if we ignore our feelings, they will bubble up and we will be unconsciously acting from 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

  35. Great. Yeah. So Carol Robbins created this movement, right? There's lit. A lot of founders go to her model that's for founders. And this is all about, they talk about a net that you can talk about your feelings and your reaction. But as soon as you cross the net to blaming someone else or making an assumption, they're going to have a defensive response. But you can be incredibly bold and brave if you stay on your side of the net. So this model helps you do that because it's really about sharing your emotions and your needs and making a request without blame

    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

  36. Lenny, try this with your wife tonight. NBC is a powerful tool. And actually, it's very akin to most models that are about connection. The Stanford Business School course that has a tea, it's called Touchy Feely that everybody loves.

    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

  37. Might make a request. I'd like to ask you next time you have a sprint planning meeting to include me as optional, or to send me the roadmap afterwards that you align on. The other person doesn't have to meet my request. They might make a counter proposal, but the most important thing of this model and this conversation is that the other person understands what I'm going through and they don't feel reactive so that we can have a mutual conversation about what's going on.

    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

  38. This is me sharing my feelings so the other party can empathize and understand what I'm going through without being defensive. The third step is needs. What are my universal human needs related to this topic? We all have needs. This is not requiring anything of the other person, just helping them understand my needs that are not met. So, I have a need for clarity. I have a need for collaboration. I have a need for connection, whatever that is. And lastly, the step is to make a request. Now, in this model, the request is an olive branch to help the other person meet you and see you. It shouldn't be something that's impossible to do. It should be actually something quite small and easy to achieve for the other person to feel successful in connecting to you and understanding you. So in this case,

    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

  39. He might have a totally different story about what's happening. So I'm going to give you a framework that I like that many of my clients use. It's from Marshall Rosenberg's nonviolent communication. He has a book and a framework. So it's four steps. The first step is observations. So my job is to note what is happening factually. Example, I noticed that in the last three sprint planning meetings, you didn't show me to those conversations or share with me the roadmap. That's an observation. It's a fact. I could take a picture of it and no one would argue with it. The next step is feelings. So I'm going to express my feelings without blame. So I felt anxious not knowing what was on the roadmap for the week. I felt confused about whether that meeting happened or not because I wasn't included.

    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

  40. First of all, people, when they want to have a conflict or they want to engage in something that's not working, they come in armored and ready to prove their point. It's natural. You've been thinking about this for reading over whether you should mention it. You finally get to the point of engaging. And often 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. So, when I go in to have a conversation with, let's say, my husband who's not doing his share of the parenting, my goal is to help him understand what I'm struggling with. That he can empathize, see clearly what's happening, and perhaps meet my needs in some way. But it's not for me to prove to him how little he's doing in the house.

    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

  41. It takes an evolved facilitator, like one of the co founders being able to hold space for both their frustration and their empathy. In a dynamic that is challenging. So outside support is useful. Sometimes it's actually a team member. It's an HR leader. It's the GC who happens to have great people skills. You don't always need a coach, but you need space to be vulnerable, open, and curious. So if you can create that on your own, that's great. I think it's definitely possible.

    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

  42. I mean, in a marriage, you're building a life with a partner. So the only difference is a marriage is rooted in sexual attraction and love. And that's not the case always in the co-founder dynamic, but I have worked with couples who are also co-founders, but there should be some element of love for your co-founder. In fact, I think that when you work closely with colleagues and you really are able to see their gifts and enable them, you can't help but love 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

  43. And after that conversation, it was really clear that one of the co-founders was unhappy and didn't appreciate the other one and was not going to change and realized he was a big part of the problem. And I think is going to leave the business. But that's still success because it's clarity. You're not muddling in the dark, frustrated, unconscious about the interpersonal dynamics you're in. You're making a choice based on your strengths and what the business needs and this relationship dynamic that you're in to either be in it or to lovingly step out of 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

  44. Was an important start to their healing. And over our coaching, they turned back towards each other and they created more of a rhythm of how they would get together without me involved. And they ended coaching after our arc feeling renewed and really recommitted. They made some changes on their leadership team to fill their gaps. They also started, I think, meeting once a week virtually. And they started a cadence of getting together in person quarterly. And I don't mean to say that just that time means you're going to heal. Sometimes coming together and really grappling, I had one last week where we all came together. We had a great full day in-person discussion about how they were making this co-founder duo, how they were making decisions.

    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

  45. What I saw them do is one, they named current state really well. They were both able to share. We did use a 360, so they got feedback from their teams and then shared it with one another. But they were able to be open and vulnerable in what was working and what wasn't working. Not immediately, but over time. And they realized they used to love being partners in this work, but as they began to lead different teams, they grew very distant from one another. They were living on opposite sides of the country and actually just coming together and realizing what each other was missing and how lonely it is to lead this scaling company without each other's support and how they actually needed the counterbalance to their strengths and didn't have 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

  46. Give you an example of this PR duo running a fierce business scaling really fast. And at one point when they started, you had the visionary who was great at selling business. They were both incredible with PR. And the partner was incredible operationally. So as the business scaled, one took on a lot more business development and the other took on all the internal things, but was exhausted by all this people management and all of the elements of kind of running a scaled team that she didn't expect to have to do. And when they came, I think both of them weren't sure, can we figure this out? Do we want to just sell this thing? Do we want to keep going? Think someone said end it or send it was what one co founder said to me. You know, they're coming at this decision point.

    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

  47. Cofounders typically come to me either in this early phase where they want to intentionally build something great and they want to set it up for success. More often co-founders come when they're really frustrated with one another. They feel the tension is palpable. They can't stand it anymore, but they're still really deeply committed to the business. So they don't see an out. And they knew that at some point they really loved this co-founder. So they see a possibility of recovering. And that's why they want to go get a 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

  48. Really like the Enneagram. I think you can also simply tell each other here are my strengths. Here's what I see as my weaknesses. And what do you think? Give me some feedback. Do you agree? And you can do that with each other without any personality assessment if you want to just be scrappy and have an open connected conversation about You can even say, what are the gifts I bring and the weaknesses I have, and how will I cover those? How will I lean into my gifts? How will I cover my weaknesses? And how will you? And then I think it's worthwhile having a conversation about what are the gaps neither of us cover that we're likely going to need as we build this business.

    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

  49. How are we going to make decisions? How are we going to deal with conflict? These are things you can go to intentionally at design with your co-founder.

    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

  50. Yeah, here's what I commit to do. So I have recently I actually wrote an article with first round and we created a document to help co-founders think about what to integrate into their check-in. So we put out weekly check-in, monthly check-in, and annual and just questions to sit down and ask each other. Active listening skills will come in handy in those conversations, but it's about taking space out of hustling and running the business to think about the business from a kind of rather I like to say instead of being on the dance floor, you need time on the balcony to look down at what's happening. How are we doing? Is this still working for both of us? And the vows are really about how are we going to be together? How are we going to show up? Like what's our culture that we're creating? Even if you don't want to go through a whole culture exercise early on in building your company, you should have some sense of how you want to show up for each other.

    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