Lenny's Podcast Transcripts

Transcript

Lenny Rachitsky[00:00:00)]When clients come to you, what is the biggest gap they have that is keeping them from being successful as leaders?

Rachel Lockett[00:00:06)]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. Lenny Rachitsky[00:00:27)]Difficult conversations are difficult. How do we help people make them less difficult?

Rachel Lockett[00:00:32)]We operate in tech. 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,

Talk about what you've learned about helping leaders in tech avoid burnout. Rachel Lockett[00:01:01)]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,

The power of this is this makes your life so much better. Rachel Lockett[00:01:28)]Lenny, let's try it. So, I want you to tell me a challenge,

something that you're struggling with. Lenny Rachitsky[00:01:34)]The main thing I struggle with these days is just... Today, my guest is Rachel Lockett, an executive coach and former longtime HR leader at Pinterest and at Stripe. She works with CEOs, and founders, and leaders at tech companies on both ways that they are, emotional and positive intelligence, resilience and courage, and what they do, setting vision and strategy, prioritizing, and building trusted and accountable teams. She's someone I've heard a lot about over the years from other podcast guests, and this conversation is powerful. It's jam-packed with advice, and tips, and frameworks that'll make you a better leader and also a better person. We even do a couple live coaching sessions to demonstrate some of Rachel's approaches. And as you'll see, I had a number of epiphanies during this conversation. If you enjoy this podcast,

don't forget to subscribe and follow it in your favorite podcasting app or YouTube. It helps tremendously.[00:02:26)]And if you become an annual subscriber of my newsletter, you get a year free of a ton of incredible products, including Devon Lovable, Replit Bolt, NNN, Linear, Superhuman, Descript, Wispr Flow, Gamma, Perplexity, Warp, Granola, Magic Patterns, Raycast, JPRD, Mobin, and Stripe Atlas. Head on over to lennysnewsletter.com and click Product Pass. With that,

I bring you Rachel Lockett after a short word from our sponsors.[00:02:49)]1.3%, it's a small number, but in the right context, it's a powerful one. Stripe processed just over $1.4 trillion last year. That figure works out to be about 1.3% of global GDP. It's a lot, but it's also just 1.3%. Stripe handles the massive scale and complexity of many of the world's fastest-growing enterprises, including 78% of the Forbes AI 50 and more than half of the Fortune 100.

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off at vanta.com/lenny.[00:04:59)]Rachel,

thank you so much for being here and welcome to the podcast. Rachel Lockett[00:05:03)]Thank you so much for having me,

Lenny. I am honored to be here. Lenny Rachitsky[00:05:06)]I'm honored to have you here. I was going to start with a different question, but we were chatting ahead of this conversation and I always like to ask guests, what do you want people to get out of this conversation? And I loved your answer, so I just want you to share this. So, let me just ask you, what are you hoping people get out of the conversation we're about to have?

Rachel Lockett[00:05:23)]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. Lenny Rachitsky[00:05:47)]So, what I'm hearing is just if you're struggling with the human side of building a product, building a team, building a company,

there are answers. You can do it. Rachel Lockett[00:05:56)]Yes, exactly. It is achievable, and it's actually most natural. Leaders 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. Lenny Rachitsky[00:06:22)]I think the hardest part of this for people is just there's the knowing this can be helped with. The other is just being vulnerable enough to seek help and to take this on because it's so hard. Just like, "Oh, maybe I'm not a great manager."

That doesn't feel good. Rachel Lockett[00:06:37)]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 of 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. He's a client I've seen for 10 years,

and he's a person who exemplifies a commitment to personal growth.[00:07:08)]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 sun with a redwood grove around it that reminded him of his core strengths and his purpose. And today, guess what he's doing, Lenny?

He's not only killing it- Lenny Rachitsky[00:08:02)][inaudible 00:08:02]

vision. Rachel Lockett[00:08:02)]... but he's running a community,

a global community for Coinbase called Base and the Base app. Lenny Rachitsky[00:08:08)]Oh,

wow. Rachel Lockett[00:08:08)]It's the largest Ethereum L2 in the world, and it's a community of creators and developers, and he's having a great time. 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. Lenny Rachitsky[00:08:33)]This story reminds me of just why I love these sorts of conversations because the sort of stuff we're going to be talking about, and we'll get into it right after this final preamble, is stuff that's usually locked away in these very small rooms, are only accessible to folks with a bunch of money. This is stuff people pay tens of thousands of dollars, hundreds of thousands of dollars for over the course of their career. And I just love the idea of sharing all this with everyone to help all learn from the stuff that you've learned from all these people you've worked with. So, I'm really excited to be digging into stuff. The first thing I want to dive into, I actually asked you, when clients come to you, what is the biggest gap they have that is keeping them from being successful as leaders? And you told me it's essentially knowing when to coach versus knowing when to just tell people what to do and learning to coach. Talk about what you see there, why this is so important,

and how you help people develop the skill. Rachel Lockett[00:09:24)]I think that most leaders, especially technical leaders, assume they have to have all the answers. People have climbed the ladder in whatever realm they're in because they've been dependable, reliable, the smartest person in the room. But 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? (00:10:12): 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. And 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. 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.[00:10:59)]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. But 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. Lenny Rachitsky[00:11:31)]Okay. I'd love to learn those skills. What this makes me think about is there's this famous Harvard Business Review piece. I don't know. It's like 30 years ago maybe about the monkey on the back. You know this piece,

Say more. I think I do. Lenny Rachitsky[00:11:44)]Okay, we'll link to it. It's this idea that as a leader, people always just coming to you trying to give you their monkey that's sitting on their back. And they're like, "Hey, this monkey is causing me all this problem. I don't know what to do. But this monkey, here you go. You take it, and feed it, and help it, figure out what it needs." And the role of a leader is to keep the monkey on the back of the person and help them figure out how to solve the problem,

exactly what you're describing. Rachel Lockett[00:12:04)]Yeah, that's a great analogy. I love that. I think leaders make things up when they don't have answers sometimes. A 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. Lenny Rachitsky[00:12:32)]Let's talk about how to get better at this. But first of all, when you said, "When is it actually smart to just tell them what to do?" You said it's when they don't have the skills to do it. Is there any other kind of heuristics of like, okay, just tell them what to do in these cases?

Rachel Lockett[00:12:43)]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. 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,

Let's do it. I'd love that. Rachel Lockett[00:13:21)]...

She's going to love this. Rachel Lockett[00:13:25)]...

Let's do it. Rachel Lockett[00:13:27)]And hopefully,

Let's do it. Rachel Lockett[00:13:31)]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."

Absolute- Rachel Lockett[00:13:49)]This is rampant in tech. And great leaders flip 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 one. 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 and focused on your words.[00:14:46)]Level three listening is global listening. So, that's what I'm hearing beneath the words. I'm 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. So, do you want to try it?

Let's do it. Rachel Lockett[00:15:25)]Okay. How about this?

Okay. Uh-oh. Rachel Lockett[00:15:32)]You told me earlier,

Yeah. Rachel Lockett[00:15:35)]What is it like to be a dad?

Lenny Rachitsky[00:15:38)]Wow. What is it like to be a dad? It's amazing. It's like the most amazing thing I've ever done in many ways. I love it so much. It's also quite challenging at times dealing with setting boundaries and knowing when to just let him do the thing he's really excited about or just saying, "no," and just letting him cry for a while. That's something I've been dealing with recently, but it's like everything people tell you it is basically in every way except the joy is so much higher, so much higher than you hear from other people because people always talk about all the downsides,

all the pain and challenges. Rachel Lockett[00:16:15)]Yeah, and I see you when you talk about being a father, initially, I saw you really squirm in your chair. Well, this is a big question. And 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. The high joy and the discomfort in having to sleep train, and having to disappoint,

and navigating challenging behavior. Lenny Rachitsky[00:16:51)]Nailed it. That was very nice to hear. Clearly,

you listened to everything I said and that was a really good example of active listening. Rachel Lockett[00:16:59)]What does it feel like to be seen that way?

Lenny Rachitsky[00:17:02)]It feels really nice. It feels really nice to be heard. And it's not just like you're repeating back my words. It's here's what I got out of the level below what you're saying, and the gist,

and the bigger picture. Rachel Lockett[00:17:14)]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 your 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. Lenny Rachitsky[00:17:50)]I think there's just so much power in different words, repeating back what they said. That's almost implied in what you're describing. It sounds like... So, I don't know, like a trick they'll see through. But knowing that you're listening to me and you're going to show me active listening,

it still feels really nice to just hear back what I said. There's a lot of power in that and it's subtle. Rachel Lockett[00:18:10)]Yeah. Great. Yeah, there's an element of synthesizing what I'm hearing verbally. That's the focused listening part, and then,

The emotions. Rachel Lockett[00:18:19)]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. Lenny Rachitsky[00:18:33)]Awesome. Okay,

so this is a core skill of coaching is active listening. Rachel Lockett[00:18:37)]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. But 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 that you can ask to unlock insight.[00:19:17)]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. 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. Lenny Rachitsky[00:20:21)]So, just to reflect back what you're saying, so someone comes to you with a monkey on their back. Here's a problem I'm trying to solve. This percent of my team is just not doing something right or this feature isn't working, something like that. So, first of all, it's listen, be very active in your listening. Reflect back what you're hearing, their emotions. And then, ask them questions around what does success look like for this? What is the goal? What is the goal? What does success look like for the thing you're trying to do here? What does success look like? Two is just what's today's reality? What's happening today? Then, options. Here's options that you think exist. So, this is you asking them what are the options?

Rachel Lockett[00:21:01)]Yeah, what are your paths forward? What could you do next?

Lenny Rachitsky[00:21:03)]What could you do next? And then, this is organic. So, it's not just like one, two, three, four,

Yeah. Lenny Rachitsky[00:21:10)]But the final step is just, okay, what's the way forward? What do you want to do?

I see. Rachel Lockett[00:21:19)]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 are they stuck? 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. Lenny Rachitsky[00:21:48)]And there's kind of an implication here that the person often knows the answer or can come to the answer,

and they just need a little bit of nudge to get there. Rachel Lockett[00:21:56)]Yeah, this is definitely you want to 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. Lenny Rachitsky[00:22:20)]This begs the question, what if they just come to a terrible conclusion and you're just like... Advice on when to actually just like, "What about this instead?"

Rachel Lockett[00:22:30)]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, help 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. You're not setting up an hour-long coaching session, you're just using coaching as an additional tool in your toolkit from advising. And you're creating more space, maybe 15% more space in your one-on-ones,

in your meetings for open-ended questions. Lenny Rachitsky[00:23:14)]I love this phrase, help me understand. One of my managers used to be really good at this, just like... You could tell, he's like, "Help me understand this part of your thinking."

Rachel Lockett[00:23:22)]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. Lenny Rachitsky[00:23:56)]And you may actually be wrong and you may realize, okay,

they actually have the better solution. I get it now. Rachel Lockett[00:24:01)]Yeah. This actually happens to me all the time in talent conversations. Because I have a background in being an 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. Lenny Rachitsky[00:24:49)]To close the loop on this piece of advice, is there an example you could share to make this super concrete for folks?

Rachel Lockett[00:24:55)]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. And he 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. So, he decided to create squads 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. But he didn't have an engineering manager and a product leader for every one of them.[00:26:00)]So, this was a little bit earlier than he was equipped for because he did it out of necessity. And he also realized he needed to create some behavior change for the way he was interacting with that tech lead on each project so that they would take more ownership. So, we really invested in this idea of I'm going to start to set the system up so we have a product review every two weeks, they each have clear KPIs they're driving to that we co-design, and for this next quarter, I'm shifting from the role of deciding on everything to coaching. I'm going to really ask good questions in our check-ins. I'm going to align to the KPIs, ask how things are going, ask where they're stuck. And I just had a session with him last week. It's amazing to see him because he's so much more energized. He said, "The squads are moving so much faster. The teams feel more empowered and motivated." And he has time to pick his head up and plan for 2026...

Rachel Lockett[00:27:01)]And he has time to pick his head up and plan for 2026, and spend his time and his gifts. Which are product,

vision and strategy. So that's more of a global example of what results from leaders shifting from the mode of solving every problem to coaching. Lenny Rachitsky[00:27:19)]That's such a great example of just the power of this, this makes your life so much better. Because other people can start picking up the slack and not come to you for everything. And it's like, listen better, ask a few powerful questions and so much improves,

Everyone around you gets better. Rachel Lockett[00:27:37)]Lenny,

let's try it. Lenny Rachitsky[00:27:38)]Okay,

let's try it. Rachel Lockett[00:27:38)]So I want you to tell me a challenge. It could be a personal challenge, a professional challenge. Just bottom line,

something that you're struggling with. Lenny Rachitsky[00:27:51)]Whoa. The main thing I struggle with these days is just endless work. I feel like this newsletter, I started this newsletter six, seven years ago at this point, and originally it was like, I'm just going to build this chill newsletter, do this on the side. Just kind of chill out for a while. And now it's just like,

it just grows. I couldn't help but make it more awesome and bigger and have this podcast now and other stuff I got going on. So it's always this.[00:28:18)]So I'm in a world now where it's just this ... the way I think about it is the Indiana Jones boulder is constantly in my back rearview mirror just coming at me. Because I need to get a newsletter post out, get podcast episodes out, do all the things associated with that. I'm also just in the middle of ... I have this large Slack community at Twitter and LinkedIn,

so I'm just constantly being barraged with small little asks and things and all these little things that never ... it's hard to just ignore and say no to. So what I struggle with just endless work. I joke that be careful working for yourself if your boss is a workaholic. Rachel Lockett[00:28:53)]I totally relate to that. Okay, so I'm hearing noise, barrage of needs and just constant requests of you online, in your work life. There's always something that you need to be doing. And you designed it that way yourself. So you're kind of aware of, I had this one intention of a path to freedom,

insight. I imagine the newsletter was a fun passion project. And you couldn't help but make it this all-consuming full-time job. Lenny Rachitsky[00:29:27)]That's right. Let me just add,

It's this Indiana Jones boulder constantly chasing me. Rachel Lockett[00:29:41)]Yeah, I can feel the gratitude and the resonance with what you get to do every day. And yet I hear you questioning, why does it have to feel like I'm fighting for my life while I'm doing this thing I love?

Lenny Rachitsky[00:29:56)]That's one way to put it,

yeah. This boulder is squishing me. Rachel Lockett[00:30:00)]I mean,

That's true. That's true. Rachel Lockett[00:30:05)]Okay, so thank you for being vulnerable enough to share that with your listeners and with me. I want to ask you, what would dream state look like? So let's say in six months you're still running this beautiful business that you've created. And you feel differently. What is happening?

Lenny Rachitsky[00:30:33)]What I imagine is the same thing mostly, just much more free time. So more time to experiment and play with other things. And at the same time, the newsletter continues to be awesome and high quality, the podcast continues to be awesome and high quality. So it's continuing to put out the same high quality stuff, just more free time,

less ... the boulders may be smaller. Rachel Lockett[00:30:56)]Yeah, okay. So what does free time enable for you?

When you think about ... I hear your deep commitment to quality products and quality output. But this longing to feel a little bit more playful or flexible with those parts that are essential to you. Lenny Rachitsky[00:31:17)]Very practically, it's time to play around with AI tools. Just explore and just kind of tinker. Versus, okay, all the time I have, I need to focus on the newsletter, make it better for next week. Oh, it's coming out, here's things I got to do. Oh, this podcast, got to prep for that,

got to edit this thing. So it's just time to tinker and explore and just like that kind of stuff. Rachel Lockett[00:31:37)]That makes sense. And what's important about exploring and tinkering to you?

Lenny Rachitsky[00:31:42)]Because in the work I do, I need to stay ahead on where things are going. I can't just sit around and pontificate from a cloud. I need to really understand how things work, what's working, what's not, what's real,

what's not. So being on the ground as much as I can with what's actually going on versus just putting out content. Rachel Lockett[00:31:59)]That makes sense. Your voice is moving really fast. I kind of hear you feeling behind,

even in the way you're describing what you're doing. Lenny Rachitsky[00:32:06)]A good [inaudible 00:32:09]

listening. Rachel Lockett[00:32:10)]What's interesting to me is when you're talking about exploring and tinkering, when you first said it, you said it in kind of a spacious way. It's fun to explore and tinker. You're deeply naturally curious. You find new insights. But then I also heard you say, "And it's a way to stay ahead, I have to do it in order to feel like I'm informed." So what do you make of that difference?

Lenny Rachitsky[00:32:37)]Yeah. Yeah. Those are two sides of the coin. There's another element of ... I guess let me answer that question. I think those are both true, I don't know. The reason I got into this is because it was so fun and so interesting. Just like, here's what's happening,

Yeah. Lenny Rachitsky[00:32:54)]Here's advice, here's ways to improve in the work that you do. So I still love it. It's just I have less time to do that part and more it's just the machine of the treadmill of content, content, content. There's also just spending more ... I didn't even mention this. But just spending more time with my son and my wife, that would be really great just to have more freedom to go do stuff. Which we have a lot of that,

but more is great. Rachel Lockett[00:33:16)]That makes sense. Okay, so the goal that I hear is not so dramatically different from today. It's that you hold on to this high quality output,

but you have space for exploring and tinkering. And for spending quality time with the people you love most. Lenny Rachitsky[00:33:33)]Yes. One way I'm thinking about as you reflect that back is 25%

more free time while everything else continues to be awesome. And the challenge I run into is I sometimes get that extra time and then I fill it with more projects and opportunities. That's the problem right there. Rachel Lockett[00:33:50)]Yeah, there's that inertia of moving fast,

taking advantage of the moment that's coming. Lenny Rachitsky[00:33:54)]Yeah,

yeah. Rachel Lockett[00:33:54)]So that's a perfect shift into, what are your current ways of operating that get in the way of having that 25% of free time?

Lenny Rachitsky[00:34:03)]It's just agreeing to more things. Just like, oh look, I'm kind of free right now. Oh, okay, let's do this talk here. Let's agree to this thing here. So it's just once I feel freedom, I'm like, "Okay, I could do that other thing."

And so I commit to more stuff. Rachel Lockett[00:34:18)]Yeah. And how is that commitment to saying yes to things that come at you serving you?

Not great. Rachel Lockett[00:34:27)]Well,

Yeah. Rachel Lockett[00:34:31)]What benefit does it have to you?

Lenny Rachitsky[00:34:33)]Well, it depends on the thing. I actually have a rule of never doing a talk or going on another podcast or going to events really, because I find I never really get much out of it,

and it distracts me from the stuff I could be doing. So I've set up a lot of policies of just turning down things that don't serve me. But I still crumble and say yes to stuff. Rachel Lockett[00:34:33)]Yeah,

that's smart. Lenny Rachitsky[00:34:57)]So to your point,

there's value here and there when I take on more work. And then I end up overworked again. Rachel Lockett[00:35:04)]Yeah, I'm hearing there's just a pattern,

That's right. Exactly. Rachel Lockett[00:35:18)]Okay. So you're stuck in this kind of addiction to doing more and signing up for more, which is so normal in our world,

and probably most listeners can relate to that. That's kind of the soup we swim in. So we have to be conscious of what inputs we have around us.[00:35:34)]So let's explore your various options that you have in front of you. One that you mentioned already you tried was to make a list of the things you don't want to be doing anymore, like things you want to say no to. And really committing to that and sticking to that. What are the other kinds of things you could do to help you prioritize and create that sacred 25% of extra time for yourself?

Lenny Rachitsky[00:36:01)]Something I've already done, which hasn't kicked in fully yet, but that I'm really excited about is I reduce the cadence of my newsletter and podcast. Which in theory, should be a massive change. But the cadence of the podcast hasn't shifted down yet, it'll happen next year. The newsletter cadences, I basically changed my promise to readers instead of, you'll receive a newsletter every week. Now it's,

Yeah. Lenny Rachitsky[00:36:28)]Which felt huge. The problem is I still like every week I'm like, "Oh, I want to write about this thing. Oh, every week there's nothing's happening, I got to put this out."

So I'm almost not taking advantage of that opportunity. So something I could do is actually not publish every week.[00:36:45)]Another is just bring on some more help. Which is difficult because I've got a lot of good help and there's only so many things other people can do for me that isn't writing an awesome newsletter and recording conversations like this. But I'm always thinking about, and I should think deeper about where can people take more load off my plate?

Rachel Lockett[00:37:04)]Yeah, I love that insight. What I'm hearing is do less in certain areas and think about your team and really expanding the capacity of your team. And be rigorous about the things you can hand off,

that you may have limiting beliefs around the things you need to do versus the people on your team. Lenny Rachitsky[00:37:21)]I might, I might. And then your point I loved,

which is just improve my policies of what I say no to that don't serve me. Rachel Lockett[00:37:29)]Yeah. What are the things you could be saying yes to if you said no to more things?

Lenny Rachitsky[00:37:34)]Just playing around with stuff. Just space to explore and tinker, and just sit around and think. Versus just go, go, go, go,

And your bucket's full with care. Lenny Rachitsky[00:38:04)]I feel that,

I feel that. Rachel Lockett[00:38:05)]Yeah. So what's one thing you could do in the next two weeks that would help you get closer to the kind of spaciousness you want to create?

Lenny Rachitsky[00:38:14)]I love that ... as we go through this, I'm thinking about this growth framework and I love how you're executing it. Like I see it in action,

it's so good. Rachel Lockett[00:38:21)]Yeah, I'm trying to do very simple coaching right now, just [inaudible 00:38:25]-

Lenny Rachitsky[00:38:24)]Yeah, yeah. No,

this is great Rachel Lockett[00:38:26)]...

that it's really easy to follow for your listener. Lenny Rachitsky[00:38:28)]Yeah, yeah. This is great. Okay, so what's the one thing I could do in the next couple of weeks to help you move forward on this? I think one is at least skip a week or two of the newsletter and just actually stick to that plan. But it's tough because the next two weeks I got already planned. I got to write a gift guide, that's my ... okay, so the week after, I'll take a break. Okay,

cool. So two weeks from the recording this I won't publish a newsletter. And then I'm going to revisit my policies on what I say yes and no to. Rachel Lockett[00:38:59)]I love that. Think about everything you're saying yes to and what are things you want to say yes to that you could treat it with. So really consider that it's a trade off every time you say yes to something. The more resonant you are with the end state and what's possible for you,

the easier it is to be disciplined in the near term. Lenny Rachitsky[00:39:20)]I love just that element of here's what you'll get out of this. It's not just no, no, no, no. It's like yes to this other thing you really,

really want to do. Rachel Lockett[00:39:25)]Yeah. Exactly. Yes, say it like a resonant full body yes to the things that are in [inaudible 00:39:32].

Hell yes. Rachel Lockett[00:39:32)]Yeah, hell yes. With an exclamation,

Awesome. Rachel Lockett[00:39:36)]Well thank you, Lenny, for letting me just demonstrate what powerful questions are. And the reason I wanted to do that with you is you brought an example that's actually pretty big. It's an emotional thing, it's a cultural norm, it's a way of being that we've all learned to be through growing up and operating in tech, especially. So even with that kind of topic, using a simple grow model can be useful. But people are coming at your listeners with topics that are very complicated, technical,

What a great ROI for me at least. Rachel Lockett[00:40:37)]What did it feel like to be coached on your own podcast?

Lenny Rachitsky[00:40:41)]It was unusual. I'm just like, wait,

I got to get back to asking you questions. That's where our minds are right now. Rachel Lockett[00:40:44)]Okay, all right, all right. We can flip it, we can flip it. I do want to name that typically when you're coached versus told what to do, you're more bought in. So if I told you, Lenny, I've heard all kinds of leaders come to me talking about being too busy. Here's what you should do. Write a list of all the things you're doing, write the things you're going to delegate, cut out 25%

of the things on your calendar. I could have given you a laundry list of things that I thought you should do without much context. But you're the expert on your own context and actually what resonates. And you're much more likely to do it if you came up with it. Lenny Rachitsky[00:41:22)]I was going to mention that earlier. That is so incredibly true. No one wants to ... unless you ask for advice, very few people are like, "Please tell me what to do."

I really love just unsolicited advice. That doesn't go well. Rachel Lockett[00:41:35)]Yeah. And great leaders often say, "Do you want advice or do you want some space to think about it? Can I help you think it through? Or would you like me to tell you what I would do?"

Great. Lenny Rachitsky[00:41:59)]This is a good segway to something I wanted to spend a little time on,

Yeah. Lenny Rachitsky[00:42:05)]What I'm talking about is stuff that often leads to burnout. I'm definitely not burnt out, but this is a common problem in tech. Where people feel depleted and just go too hard. So many people I've worked with just left tech. I had a colleague at Airbnb,

So peaceful and so wonderful. But I think that's just people go so hard sometimes and then just get burnt out and never want to do anything like this again. I know that you've spent a lot of time on this with founders and you have a really helpful approach. So just talk about what you've learned about helping leaders in tech avoid burnout and feel energized and excited about their work for a long time. Rachel Lockett[00:42:47)]Yeah. Well first of all, I'm glad you brought it up. It's a huge problem. I remember when I was coaching top talent at Stripe, Patrick Collison is really committed to retaining top talent. And I created a program with my team for the top 50 executives in the tech side of the house. And we looked at their engagement scores,

we did coaching circles. And it was so sad to see how exhausted that group of incredibly creative and committed leaders was in that moment.[00:43:19)]And it's so common that people who start with incredible inspiration and incredible capacity start to feel like they've been pushing and pushing and pushing for years. They're parenting, they're leading,

crazy things are happening to the business. And they just can't muster the same kind of motivation they once had. And I see this with my clients all the time.[00:43:44)]So I've also witnessed people who are still inspired and continually energetic and seem to have some secret well of some diesel battery, or I guess I should say a Tesla battery that helps them through really hard challenges, and they're still having a good time. And so what I make of that is that when people are in their gifts and their strengths firmly, most of the time,

they have more energy. We all have more energy when we're operating from the things we naturally are good at and the things we innately love doing.[00:44:25)]So I try to help my leaders see that they can design their lives so they're spending 80% of their time in their gifts. That seems really ambitious because you're stuck within a context that requires a lot of you. Especially when you're executive at a huge company. But I also interact with founders who started a company with great inspiration, an entrepreneurial vision, and their job has obviously changed every six months. Once you fundraise, once you grow a team. And sometimes, especially technical founders will start solving a technical problem they're absolutely obsessed with. They spend three years doing it, the product ships,

and then they're stuck managing a board and a team. And they don't even realize they're doing a completely different job than the one that played to their strengths.[00:45:17)]So one tool I like to give is for people to actually take two weeks and every night reflect on, what are the five things today that gave me the most energy? And what are the five things that depleted my energy the most? If you do that for two weeks and you look at patterns, you can tell, what are the natural gifts that I'm living in? And what are the things that I'm stuck doing that are exhausting?

And they're just slowly ... it's like a slow leak in your gas tank that over time shows up in your daily amount of energy. Lenny Rachitsky[00:45:52)]I so believe this advice is so effective. This is the way I actually approach when I left my job. I very actively did this. I paid attention every day, what gave me energy? And what sapped my energy? And let me just do more of the thing that gave me energy and less of the thing that saps me. I want to talk about just like, there's only so much you can change, but I want to talk about that. And so initially I was like,

Interesting. Lenny Rachitsky[00:46:23)]Doing these calls and talking to people because it's like surface level, here are some things I would do. And it was just so unexciting and energizing. But writing was really energizing,

I love that. Lenny Rachitsky[00:46:36)]And that's what I did,

and I just followed that pole. Rachel Lockett[00:46:38)]And it sounds like maybe you need a refresh,

Lenny. Lenny Rachitsky[00:46:42)]Oh,

interesting. Rachel Lockett[00:46:43)]There's always more tuning you can do to your gifts. You're in this amazing ... you've clearly been successful for a reason, you're in your strengths and you're paying attention to what brings you energy. We can always do that more throughout our life. I think it's a process of continually tuning in to where your spark is. And protecting that spark,

feeding it. Lenny Rachitsky[00:47:05)]I love that insight,

that just blew my mind.[00:47:08)]So very tactically, the way you would do this is for two weeks every night is the idea, reflect back on that day and write down five things that gave you energy,

five things that sap you of energy. Rachel Lockett[00:47:19)]Yeah, there's so many different activities you could use. So that's one. I like an activity of actually asking five to ten people in your life with a very simple email. When I walk in the room, what shows up? What are my strengths? What are the gifts? If you really don't know them and you haven't spent a lot of time in this realm, that's also an opportunity of actually asking the people who know you best, what your core gifts are? And when do you have the most inspiration? (00:47:46): You can also look through your calendar and note themes. Okay, over the last month, what are all the things I look at on my calendar that I'm excited to do? What are the things I dread? Okay, why do I dread those things? What do those things have in common? So there's various ways you can get to what is your zone of genius? But what my invitation is to take that really seriously. It actually takes risk taking,

it takes intention to design your life around your gifts. Lenny Rachitsky[00:48:15)]Is there any advice for actually doing this? Say someone's just like, "Yeah, I got to do this." But most people don't actually do this. Is there a buddy you can nominate, just help you do this? Is it like if you have an EA, they can maybe help you with this? Is there anything you've seen?

Rachel Lockett[00:48:28)]That's a good question. Yeah, I love your ideas. I think that the people around you need to be on board and know what are your gifts. So for example, when I was an HR business partner, my boss bought into this and I explained to her, "Hey, I started at Stripe because I actually know I'm going to be a coach. I'm not going to be Head of HR. But I love working with leaders. So I'm going to do all the compensation strategy and all the org design, and I'm going to help product and engineering leaders. But what I have in the back of my mind is I'm honing my coaching skills." (00:48:56): And so when this opportunity to work on top talent retention came about, it was very aligned in the realm of coaching and L&D, background that I had. So she put me on that. So it's useful to name it to the people around you. What are your gifts? What are your interests? What skills are you really excited to hone?

So that they are in a contract with you to help you and really apply your gifts to the business's needs. So that's one thing.[00:49:23)]When you're a founder, a CEO, when you have the autonomy to consider, what are the role scopes around me? Then you can really hire around it. So I have some CEOs that I work with who are incredible visionaries, great strategists, really good at managing the board, hiring, et cetera. Terrible at managing their team. They hate it. So they hire a COO. And they work in partnership, they have one person who's really internally focused, they get to be externally focused. That works well, it's a symbiotic relationship. If you're honest about your strengths and you're weaknesses,

then you can start to manage around them. Lenny Rachitsky[00:49:59)]This episode is brought to you by Persona, the verified identity platform, helping organizations onboard users, fight fraud and build trust. We talk a lot on this podcast about the amazing advances in AI. But this can be a double-edged sword. For every wow moment, there are fraudsters using the same tech to wreak havoc. Laundering money, taking over employee identities and impersonating businesses. Persona helps combat these threats with automated user, business and employee verification. Whether you're looking to catch candidate fraud, meet age restrictions or keep your platform safe, Persona helps you verify users in a way that's tailored to your specific needs. Best of all, Persona makes it easy to know who you're dealing with without adding friction for good users. This is why leading platforms like Etsy, LinkedIn,

Square and Lyft trust Persona to secure their platform.[00:50:48)]Persona is also offering my listeners 500

free services per month for one full year. Just head to WithPersona.com/Lenny to get started. That's WithPersona. com/Lenny. Thanks again to Persona for sponsoring this episode.[00:51:04)]It's really nice to know what you want to do and understand what your dream life looks like. You also have a job, you have manager, you got things to do, you got responsibilities. So I guess first of all, as you have seen people that are not founders actually make a change to do the things ... to spend more time on their gifts,

Is kind of an implied piece of this. Rachel Lockett[00:51:30)]Yeah, I think sometimes people hire a Chief of Staff to help them and compliment them. Sometimes people design their team with strengths and gifts that they don't have. So it's really ... you can get creative once you really understand, oh, these things give me a ton of energy and these things are exhausting. But I still need to fill this need for the business. What are all the ways I can do it?

Lenny Rachitsky[00:51:52)]And telling your manager, I think,

Absolutely. Lenny Rachitsky[00:51:58)]... here's where I want to go, here's the things I want to get better at, here's the things that give me energy. Can we just try to make as much of my role that?

Rachel Lockett[00:52:04)]Yeah. Especially if you're executing well, people want to retain you. They want to know, what's going to keep you here for the next five years? And typically they think that means moving up the ladder. But maybe it doesn't for you. I think it does take the courage to move horizontally sometimes to get into your strengths. I mean, I've moved horizontally a number of times and I love what I do,

I feel like I'm in my natural gifts. But it took me a few risks and some uncomfortable jobs that didn't feel like they were worthy of my experience in order to get there. Lenny Rachitsky[00:52:38)]What's a good percentage of your work life that should be in gifts and things that energize you versus, okay, I actually got [inaudible 00:52:48]

stuff. Rachel Lockett[00:52:48)]My litmus test is 80%,

that's the goal. Lenny Rachitsky[00:52:48)]80%.

Rachel Lockett[00:52:48)]That's the aspiration. You're always going to have 20% of things you don't love doing. There's just the logistics of getting into the zone that you need to be in. But I really try to push people to think aspirationally, that if you're 80% of the time in your gifts,

how much energy you have to give to the world. It's so much more inspiring.[00:53:09)]So I want to tell you why I'm passionate about this topic because it actually is how I ended up as an Executive Coach. So 10 years ago, I was working at a small company called Remind, and I was running the UX Research team. And the CEO asked me to move into the Product Manager role for the Core Product team. And I was excited for the opportunity. I had non-technical background, but I thought, "Hey, all these strategists are up there creating the roadmap. I can do that. I know exactly what our users need."

So I was excited for this.[00:53:44)]I came into the team, there was I think 12 senior engineers, very opinionated, very skeptical, this non-technical PM, but we worked together. And what I did was I listened. I learned what do our users need? What does this team need? What's working and not working?

And with- Rachel Lockett[00:54:00)]What does this team need? What's working and not working? And within a month, this team was working well together. They were reviewing each other's code base. They were really disagreeing in a healthy way in our team meetings. They felt more connected to users. And I felt like, "Okay, this rhythm is working." But what I was also doing as I was at home stressing in the middle of the night about the new user experience, I couldn't decide which of the designs to go with. I was always over leveraging our data scientists, and I found myself swirling on decisions that didn't need to have so much stress involved. And one day I went for a walk with my colleague Zach Abrams,

and he was a great product manager and he was listening to me ask all these questions about how to sell the vision of what this product would look like in the future.[00:54:55)]And he said, "Rachel, you're a zone of genius or your gift is not being a product strategist, but I've watched you over the last few months, and you have gotten the team more motivated than I ever could, and you've influenced the entire executive team behind your ideas, and that's impressive. You're a people person." And at first I was offended. What? You think I don't have the ability to be a great product leader? And yet I sat with what he said, and I knew he was right. Both my parents are therapists. I never wanted to be a therapist. Here I am. I'm basically a work therapist. I love entrepreneurial energy, I love big vision,

but I'm a people person.[00:55:40)]And I left that, and I realized I love what my coach does. I got trained as a coach. I went into HR leadership. And Zach, who was a gifted product strategist, went on to lead product at Coinbase and BREX and most recently Bridge, which was acquired by Stripe, and he's still my client. And we've watched our journeys over the last decade, and we've both been honing our gifts. Life is more fun when you're in your gifts,

and you have more inspiration and capacity to offer the world. So I just want to share that story because it's helpful to be honest with the people you care about when they seem energized and when they seem depleted because sometimes it's a wakeup call for people to really think about what is their spark and to protect it and to feed it. Lenny Rachitsky[00:56:36)]I love that story because I think most people when they hear this advice and this topic of, "Okay, I am feeling depleted, I'm feeling burnt out," I feel like most people jump to, "Okay, but I can't actually do anything about it. I have a job. I got responsibilities." What I'm getting from this is the most important step is jump to figure out what you actually should be doing. What gives you energy? What your gifts are. It feels like that's the biggest gap for people because once you know that, there are ways to do that. Talk to your manager. "It may not be possible today, but here's where I want to be going. Here's what I want to be spending time on." I love your point you made though about you actually have to be doing well for your manager to listen to you. You can't just be sucking and then like, "Oh, but I want to work on strategy."

Rachel Lockett[00:57:19)]Yeah. Well, it's no one else's job to help you live in your gifts. And what I notice in big companies is people are often annoyed or frustrated with their management for not making their job more interesting. It's like, "No, your manager's job is to help you perform in the job you were hired to do. It's your job to navigate your career." So over the arc of your career, how do you match your gifts with the world's needs? And if the world right now is your company, how do you understand the needs enough so that you can apply your strengths to those needs?

Lenny Rachitsky[00:57:54)]This reminds me, there's a couple of guests I've had on the podcast who did this. They're both founders, so this is specific to founders, but Rahul Vohra at Superhuman, he realized he's not the best executor operations person, so he hired a president that took all that office plate. And then Darmesh, co-founder of HubSpot, he knew from the beginning he didn't want to manage people, so he made a rule with his co-founder, "I will never have reports." And he's the CTO, I believe, and has zero reports,

has no one-on-ones. Rachel Lockett[00:58:23)]Yeah. And I think that it's a beautiful thing to recognize that, but then to actually address the needs of those reports also. I think often people know, "Ugh, I don't want to have one-on-ones,"

but just not having anyone to manage those people is not going to be healthy for your company. So you have to both take your strength seriously and actively manage around your weaknesses. Lenny Rachitsky[00:58:45)]Is there any maybe last piece of advice on this topic of helping people get to a place where they're feeling much less depleted and just more energized at work?

Rachel Lockett[00:58:53)]I would start small. You don't have to leave your job and redesign your life. You can stop going to the optional things that are exhausting. You can leave space between the things that are depleting that you have to go to outside and go on a 30-minute walk and refuel your tank. Start with tomorrow. What are the three things you're going to do to plug up that gas leak and re-energize your spark? It might even be you love to read and you're going to start reading 30 minutes before you go to sleep every night. It doesn't have to be a dramatic life change, but recognize that only you know what is resonant and what is depleting,

and it's your job to take that seriously if you want to show up purposeful and impactful in the world. Lenny Rachitsky[00:59:41)]I love that advice. I've actually started reading before bed for 30 minutes, and that's been so joyful,

like a physical book with a little nightlight. Rachel Lockett[00:59:48)]I agree. I love a physical book. I have a Kindle, I got all the things,

but a physical book on the couch is the best. Lenny Rachitsky[00:59:55)]Yeah, it's just that nightlight is key because sometimes at nighttime you need a night book. So we've been talking mostly so far about individual improvement, how to figure out what you should be working on, just helping learning to coach, things like that. I want to take us up a little level above and talk about team skills, how people get better at working with other people. Something that you are in many ways known for is helping co-founders build better relationships. And in my experience one of the most challenging parts of starting a company is the co-founder relationship. A lot of people don't realize what they're getting into. You're basically getting married to this person in a very high stress situation,

Exactly. Lenny Rachitsky[01:00:39)]And then you not working well together is just a huge issue because that all trickles down, and everyone sees it. And when co-founders leave, it's really bad for everyone. So let me just ask you this, what have you found most helpful in helping co-founders build great relationships, stay happy and productive?

Rachel Lockett[01:00:56)]Yeah, thanks for asking this. I love working with co-founders because I think your core values as a person come out when they interact with someone else's core values. Conflict, healthy conflict or otherwise, is actually where your core values come out. So it's fascinating to watch people try to do something incredibly hard in the context of someone else's vision, someone else's strengths and weaknesses and navigate that together. So there's so much energy in the co-founder dynamic for me and for co-founders themselves. It's actually something that people don't feel comfortable going to their board about or talking to that many people about because it's a private matter. It's almost like in a marriage you go see a couples' therapist, but you don't tell all your friends that you can't stand your partner, but it keeps you up at night. So it's a really tender, important relationship,

and there aren't enough supports for co-founders to navigate it. It's very normal.[01:01:50)]In fact, I know you probably know this stat, 65% of startups fail because of co-founder conflict, and co-founders are in a moment where they're trying to build the future for their business, but also trying to build their own livelihood. So there's so much at stake to get along with your co-founder. I think the core at its core, what you need in a healthy relationship is, one, self-awareness. What do I bring into this dynamic, and how am I being experienced by the other person? What does this other person bring into the dynamic, and how am I reacting to that? So the first is just collective awareness about what is our dynamic. I like to use the Enneagram for this, but there's all kinds of tools,

self-awareness tools that you can use to give a common language to what is my thing and what is your thing.[01:02:46)]A very classic one has to do with roles. CTOs tend to be skeptics. They love facts, they seek knowledge. They want depth of awareness and understanding, and they also like to be self-sufficient. This is a total generalization, but I've seen this pattern over and over again. The CEO is the person who had to sell the vision. They're a person who loves big picture vision strategy. They often are great at influencing others. They love to sell ahead of the reality of what the company's actually built. This creates an inherent tension between blind optimism and skepticism, and it's a dance that these two roles play together. So the first part is knowing the dance you're in,

so you're not just stepping on each other's toes blindly.[01:03:34)]The second step is actually being conscious about the commitment you're making to your relationship. In a marriage, for example, I talk about co-founder vows and recommitments and renewals because in a marriage you get married, and a lot of times people build a family and then they think, "Oh, the relationship will just continue around each other all the time. We're doing this thing together." But just like couples need a date night, co-founders need time and space to connect with each other to come together and say, "How's this working for you? Are we still aligned on our vision and our strategy? How are we working together? What am I doing that's pissing you off? What are the things that have gone unsaid and that we need to talk about?" (01:04:20): But if you're just in the hustle and bustle of running and scaling your startup, you don't make time for that conversation. So I think it's incredibly important for co- founders to make space for their relationship, whether that's a dinner every other week, whether that's going out to lunch regularly, whether that's just touching base business-wise,

but having an in-person quarterly check-in. That space is critical for the health of a co-founder relationship. Lenny Rachitsky[01:04:50)]On that second piece, the vows idea is such a good idea. Is that something you actually recommend, here's what I vow to do?

Rachel Lockett[01:04:56)]Yeah, here's what I commit to do. So 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 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? What's our culture that we're creating? (01:05:43): 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. How are we going to make decisions? How are we going to deal with conflict?

These are things you can go into intentionally and design with your co-founder. Lenny Rachitsky[01:06:03)]Awesome. We're going to link to that post The first step, Enneagram sounds like that's what you recommend,

and this is basically a personality profile that a lot of people love. Rachel Lockett[01:06:12)]I 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 could 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?

Lenny Rachitsky[01:06:50)]What do you recommend people do when they are just like, "Our relationship isn't working great. There's a lot of tension"? All this advice we've been talking about, at the beginning, here's things you can do to set things up for success. Understand what you're good at, what you're bringing to the table. Consciously commit to, here's what I'm going to do, here's what you're going to do. Have these dinners or lunches. I love this metaphor of going out on the balcony and just reflecting on how it's going. So that's all really great. What if you're just already in it and it's really annoying, I don't like this person that much or so much tension constantly. What are a couple things they can do this week, next week?

Rachel Lockett[01:07:27)]Co-founders 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 cofounder, so they see a possibility of recovering, and that's why they want to go get a coach. I'm going to 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.[01:08:17)]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 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? And I think someone said, "End it or send," was what one co-founder said to me. They're coming at this decision point. And 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.[01:09:16)]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 was a important start to their healing.[01:09:48)]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.[01:10:36)]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. Lenny Rachitsky[01:11:16)]I love how similar this is to just the marriage,

all this stuff. This is the same sort of thing you would do. Rachel Lockett[01:11:21)]Totally. I mean 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,

That's a big statement. The other takeaway here is that just get coaching. It feels like that's the solution if things are just not working great. There's only so far you can get just talking. Rachel Lockett[01:12:01)]It takes an evolved facilitator, 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. Lenny Rachitsky[01:12:35)]Outside of the co-founder relationship, do you have any just tactical tips for people to improve their interpersonal skills with just team members, anyone they work with, just people that may struggle like, "Man, I have a hard time with this person. I just have a hard time with a lot of people"?

Rachel Lockett[01:12:50)]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, perseverating 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 so 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 because he might have a totally different story about what's happening.[01:13:54)]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. It is 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. For example, I noticed that in the last three sprint planning meetings, you didn't invite 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. So this is me sharing my feelings so the other party can empathize and understand what I'm going through without being defensive.[01:14:59)]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,

I 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.[01:15:54)]Now, the other person doesn't have to meet my request. They might make a counter proposal,

but the most important thing of this model in 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. Lenny Rachitsky[01:16:12)]Wow. This point about how when you're trying to convince someone of something, when something is going wrong, this point that your goal is not to convince them, that your goal is to have mutual understanding, that just blew my mind,

and I think it's going to change my life. Wow. Rachel Lockett[01:16:32)]Lenny, try this with your wife tonight. NVC 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 T,

it's called Touchy Feely that everybody loves. Lenny Rachitsky[01:16:48)]Yeah,

we've had Carol on the podcast. Rachel Lockett[01:16:49)]Great. Yeah,

And tech. Rachel Lockett[01:16:56)]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. Lenny Rachitsky[01:17:21)]Yeah. So what I was going to say as you were going through this framework is here's me, here's what I saw, here's what I'm feeling, here's what I need. And then now that you have that in context,

here's something I'm asking for versus you did this and you're feeling this and you thought this. Rachel Lockett[01:17:37)]Exactly. It also acknowledges that professionals have feelings. I think that we operate in tech. We're supposed to give all of ourselves, all of our time, all of our energy to this endeavor. And it's purely logical. It'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. Lenny Rachitsky[01:18:00)]And there's this implicit power here that if the person cares about you and loves you or values your relationship, knowing that this makes them feel bad will make them want to change. It's not like you need to tell them, "Change this thing. Oh, I didn't realize this made you upset or that you have this need. And now that I know that, okay, now I see why this is important to you."

Rachel Lockett[01:18:22)]That's exactly right. And sometimes the other person will hear that and have a different story or a different perspective. 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 once you're vulnerable,

they're going to share their vulnerability. Lenny Rachitsky[01:19:00)]Let me remind folks of the framework. I'm going to try using this. I wish it was a handy acronym off. So the framework is share what you've observed, just the facts of what is happening. Just simply, I saw you didn't close the fridge fully. Your feelings of how that made you feel, the needs that your core human need that drives that feeling,

I imagine. And then the request you have of the person. Rachel Lockett[01:19:28)]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. Lenny Rachitsky[01:20:05)]Are there phrases that are just examples of non-feelings, like using the word "you" in the way you describe a feeling probably is not a good sign?

Rachel Lockett[01:20:14)]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. Lenny Rachitsky[01:20:24)]So don't say like, don't say you, don't say that?

Rachel Lockett[01:20:27)]Yeah,

exactly. Lenny Rachitsky[01:20:29)]Awesome. Along this topic, I chatted with a number of clients that have worked with you over the years, and one of the most common themes that they said you help them with is having difficult conversations. And I think we covered actually much of this in what we just talked about,

but I'm curious if there's any other advice you have for helping people have difficult conversations. Let me read a quote from one of your clients. Rachel Lockett[01:20:52)]Oh,

wow. I love this. Lenny Rachitsky[01:20:54)]So she said, "Rachel is exceptional at making difficult decisions clear and making it feel possible to get these decisions actualized."

Is there anything more- Lenny Rachitsky[01:21:00)]... these decisions actualized. Is there anything more there for, because difficult conversations are difficult. How do we help people make them less difficult? Any tips?

Rachel Lockett[01:21:11)]Yeah. Well, first of all, difficult conversations makes you want to run away. The marketing on conflict is poor, so 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. When 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. And there's something to learn from it.[01:21:57)]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." The 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. So first, I just want listeners to reframe ambivalence and interpersonal challenge,

think of them as a growth opportunity.[01:22:56)]Second, there is always something that we're doing to contribute to the conflict, even if it feels like the other person is insane, and is driving us crazy, and we're the innocent party. So entering any conflict conversation with humility, and curiosity about the other person's experience, is critical to setting the table for a 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 a hundred percent responsibility. Not being in the world of blame, being a victim, or being a hero. 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." (01:24:10): Instead, take responsibility for your part. "What is my piece in making this dynamic happen and how can I address it?"

Lenny Rachitsky[01:24:18)]That makes me think about, Jerry Colonna was on the podcast, and he has this famous line that I've always remembered. How are you complicit in creating the conditions that you claim you don't want?

Rachel Lockett[01:24:29)]Yes,

I love that. Love that question. Lenny Rachitsky[01:24:32)]And there's so many, there's three parts to that whole question, I won't get into it. But what you're sharing here is, think about that, figure out how, because your point is, you're always somehow complicit in creating the issue you're complaining about. And use that to help kind of put down the defense of the person like, "Here's what I've contributed to this problem." Do you use the nonviolent communication framework? And I don't know, is that just a general way of trying to have difficult conversations, or is there not a framework?

Rachel Lockett[01:24:58)]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. And so, that's the instigator to know, "Okay, I need to talk to this person. We need to clear this up." (01:25:17): 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 daggers thrown at him all the time. And it was exhausting, and frustrating, and confusing. That was a time where he used NVC 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. Lenny Rachitsky[01:26:02)]Awesome. Just remind folks of the NVC framework, because this is the thing that's hard in the moment. Like, "Oh, what should I be saying?" Observe, feelings, needs,

request. Rachel Lockett[01:26:11)]Yeah, exactly. And there's a nonviolent communication book, if folks are into the framework,

and want to check it out. Lenny Rachitsky[01:26:17)]People need a little... Who was it, you said one of your client's tattooed the vision he had,

Yeah. Lenny Rachitsky[01:26:22)]Okay, there's,

Maybe don't tattoo NVC. Lenny Rachitsky[01:26:25)]Because that may be [inaudible 01:26:25]

Rachel Lockett[01:26:27)]It doesn't have a good acronym. You could just print it out, and put it right next to your screen,

or something- Lenny Rachitsky[01:26:27)]All right,

okay. Rachel Lockett[01:26:30)]...

if you want. Lenny Rachitsky[01:26:31)]No tattoos. I just want to highlight the first point you made in this answer, of having difficult conversations. And then I have one more question for you. Just this point about, if there's something you're afraid of, that is a sign you should do that. There's a quote I often think of. "The cave you fear contains the treasure you seek." And the advice there is just, the thing you're afraid of is a compass too,

the thing you should do. Because there's something important there. Rachel Lockett[01:26:58)]I love that. Yeah. It's like, "What's important here? What do I have to learn here?" Is a question you can ask yourself when you're avoiding something. I often see this in talent management situations. A CEO has an underperforming COO. They're avoiding a conversation, because they keep getting let down, and actually they kind of know deep down,

this is not working out. They don't want to face it. It's too much work. They need to just keep plowing forward.[01:27:27)]And when we really take space to think about their feelings and needs, they realize, I ask them, "Would you enthusiastically rehire this person for the same role?" Which is the question we always asked 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. Lenny Rachitsky[01:28:01)]That is a really cool tip. I did not know Stripe operated that way. We had the CTO of Netflix on the podcast, Elizabeth Stone, and this is very much how they operate. They're always asking a question like that. The way you phrased it was, "Would I enthusiastically rehire this person for the same role?"

Rachel Lockett[01:28:18)]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. Lenny Rachitsky[01:28:33)]And the answer isn't, if it's no, it's not, "Fire them." It's, "You need to do something about it." It could be talk to them about it, put them on a performance plan, put them in a different role. It doesn't mean you have to fire them immediately, so it's not necessarily as scary as it sounds,

if you say no. Rachel Lockett[01:28:47)]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. Recognize that in how you're interacting with your current CFO, put out a search. 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. Lenny Rachitsky[01:29:28)]And I guess it's very important to highlight the importance of operating this way, if you're trying to build a really successful company, is that should be the bar. Is, if you would not enthusiastically rehire this person for this role. If you're trying to build something that's never been built before, and build a company that actually works out really well,

you need to really only have people around that are hitting that bar. Rachel Lockett[01:29:50)]Yeah. My perspective, 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 and 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. You're going to build a different size business, if you're in a sector that's not growing, than right now, if you're in the middle of AI. True. You're riding 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 that you put that talent in. So you need to create the conditions such that your talent can thrive. Lenny Rachitsky[01:30:37)]Such a simple concept, that I think people overlook, is just everything you do is going to be the people that you have around you, and the environment you create for them to operate. I think your point about when you're doing something difficult, just to close out this element, I love this idea that if it feels hard, think of it as a learning opportunity. I think anyone listening to this is like, "Oh, cool, I'm going to learn something. I'm going to get better." It's such a easier,

more motivating way of approaching something that's difficult. Rachel Lockett[01:31:05)]And I want to make a distinction between that and 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. Interpersonally, 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. Lenny Rachitsky[01:31:48)]A final area I want to spend a little time on is, something that I've heard from everybody that you work with, which is the way that you help them operate. So you just talked about the importance of the people you hire and the environment you create for them. And something that you help leaders do is create a very specific way of operating around a one-page plan, and how that kind of trickles down and just makes everything at a company more effective. Talk about this one-page plan,

how you recommend companies operate with this. Rachel Lockett[01:32:17)]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.[01:32:50)]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?" (01:33:14): So I actually got this idea of the one-page plan from Alpine Investors. They have something called the People First Operating Rhythm, and they've 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.[01:34:04)]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. Lenny Rachitsky[01:34:30)]We're going to hopefully link to a template of this one-page plan?

Rachel Lockett[01:34:33)]Yeah,

sure. Lenny Rachitsky[01:34:33)]Okay,

Happy to share. Lenny Rachitsky[01:34:34)]Okay, so let's do that. And then, what kind of impact do you see from companies starting to operate this way to motivate people to do this?

Rachel Lockett[01:34:41)]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.[01:34:57)]So in my opinion, a very under- attended to part of building a business is an operating rhythm. When do you come together to kick off the year, and share your strategy and vision again, and talk about the goals? When do 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? (01:35:25): 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. 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?" (01:35:56): I really like the question, "What's an inconvenient truth?" Air 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.[01:36:26)]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, create,

and come back to the meaningful work you're doing more energized. And leadership teams need that too. Lenny Rachitsky[01:36:45)]Wait, Alpine Investors,

I saw that. I saw that. Lenny Rachitsky[01:36:49)]I love that. Okay, final, final question. I want to take us to AI corner before we get to the very exciting lighting round. I'm going to do kind of a tweaked version. Usually I ask people just, how has AI impacted their work and life? I guess that is the question here, just how has AI changed, I guess coaching, as a coach? But also just, from a client's perspective, how are people using AI to help them in their, I guess life, from a coaching perspective?

Rachel Lockett[01:37:13)]Yeah, it's a great question. So as a coach, I use AI in a couple of key ways, that I'm grateful for. One, I use Granola,

which I saw you give away to your listeners. Lenny Rachitsky[01:37:23)]One free year of Granola, for becoming an annual subscriber of Lenny's Newsletter,

There you go.[01:37:29)]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. I 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 struggling with now."

So it helps me create the kind of transformation that I want for all my clients.[01:38:08)]Secondly, 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 creative energy that I otherwise would need to get together with other coaches to discuss. And I do that,

too.[01:38:50)]Finally, 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.[01:39:17)]So I'm curious about the future of coaching, how in between sessions, clients can get access to more of an AI support, where the bot has all of their context, their development plan that we create 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, so that they can access between, just some extra spot support. They're going into 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 then, AI can play a real helpful role in between,

on the tactics. Lenny Rachitsky[01:40:15)]That is super cool. So that's something you already do,

It's something I'm building right now. Lenny Rachitsky[01:40:20)]You're building,

My clients don't have that yet. Lenny Rachitsky[01:40:22)]Okay. That is great. That is a really good idea. It's not replacing coaching and therapists, let's say, but it's adding a lot more in-between time where you could just talk to us, based on everything you've talked about,

Exactly. Lenny Rachitsky[01:40:47)]Rachel, is there anything else that you want to share or leave listeners with, before we get to our very exciting lightning round?

Rachel Lockett[01:40:55)]What I want to share is that the world is getting more lonely. There's 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 am a fan of this AI boom, I appreciate that we have more technology at our fingertips than ever before. But I 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. Lenny Rachitsky[01:42:03)]What a beautiful way to end it. With that, we've reached our very exciting lightning round. I've got five questions for you. Are you ready?

I am ready. Lenny Rachitsky[01:42:11)]First question, what are two or three books that you find yourself recommending most to other people?

Rachel Lockett[01:42:16)]One of them I said before, The 15 Commitments of Conscious Leaders. And I love Designing Your Life,

by Bill Burnett. Lenny Rachitsky[01:42:25)]I love that book, too. People don't talk about that book enough. Next question. Favorite recent movie or TV show you really enjoyed?

Rachel Lockett[01:42:31)]Oh, God. I just went to KPop Demon Hunters with my daughter. It's so embarrassing, but that's what we dressed as for Halloween,

like everyone else in the world. Lenny Rachitsky[01:42:38)]I have not seen that. I hear everyone talking about it. I am going to try to avoid it, I think. Next question. Favorite product you have recently discovered that you really love? Could be an app, could be a gadget,

Amazing. Rachel Lockett[01:42:51)]I've 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. Lenny Rachitsky[01:43:02)]Do you have a favorite life motto that you often come back to, in work or in life?

Rachel Lockett[01:43:06)]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. Your own path, you make with every step you take. That's why it's your path."

That's a Joseph Campbell quote. Lenny Rachitsky[01:43:27)]Beautiful. Final question. You've got two kids, you said. Do you have any favorite children's books that you most love reading to them, that they've loved most?

Rachel Lockett[01:43:36)]Oh my gosh. So my daughter is really into Roald Dahl. I love Roald Dahl, 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. Lenny Rachitsky[01:43:54)]Have you seen the Wes Anderson stories of his stories, where he takes [inaudible 01:43:58]-

Rachel Lockett[01:43:58)]Some of them,

yeah. They're great. Lenny Rachitsky[01:44:00)]Yeah, they're so amazing. Oh my God. And it's like Roald Dahl is like,

I think it's personifying him. He's like a character in the story. Rachel Lockett[01:44:06)]Yeah, he's a character,

from what I hear about his life. Lenny Rachitsky[01:44:09)]Rachel, this was incredible. I feel like we've very much accomplished what I set out to do, which is just give people all this advice that they never have access to that,

Absolutely. Thanks for having me. Lenny Rachitsky[01:44:28)]I almost forgot to ask you two final questions. Where can folks find you if they want to reach out, maybe consider working with you? And how can listeners be useful to you?

Rachel Lockett[01:44:36)]Yeah, find me at lockettcoaching.com, and how can listeners be useful? Listeners should turn towards each other, build great relationships,

Thank you so much for being here. Rachel Lockett[01:44:50)]Thanks for having me. Take care,

Lenny. Lenny Rachitsky[01:44:52)]Bye,

everyone.[01:44:55)]Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating, or leaving a review,

as that really helps other listeners find the podcast.[01:45:09)]You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.