A guide to difficult conversations, building high-trust teams, and designing a life you love

Rachel Lockett is a sought-after executive coach and former HR leader at Stripe and Pinterest who now works with CEOs, founders, and tech leaders on emotional intelligence, resilience, and leadership skills. In this episode, Rachel shares powerful frameworks for coaching reports, having difficult conversations, avoiding burnout, and strengthening co-founder relationships. She also demonstrates these techniques through a live coaching session with me. *We discuss:* 1. When to coach and when to just tell people what to do 2. The GROW technique for helping people figure out a solution for themselves 3. Techniques for making difficult conversations less difficult 4. Avoiding burnout and designing a more energizing career 5. Building and sustaining a healthy co-founder relationship 6. Creating a one-page plan that aligns your entire company 7. Practical ways AI is transforming executive coaching and leadership development 8. Why you should ask, “Would I enthusiastically rehire this person?” to clarify talent decisions *Brought to you by:* Stripe—Helping companies of all sizes grow revenue: https://stripe.com/ Vanta—Automate compliance. Simplify security: https://vanta.com/lenny Persona—A global leader in digital identity verification: https://withpersona.com/lenny *Transcript:* https://www.lennysnewsletter.com/p/a-guide-to-difficult-conversations *My biggest takeaways (for paid newsletter subscribers):* https://www.lennysnewsletter.com/i/178940830/my-biggest-takeaways-from-this-conversation *Where to find Rachel Lockett:* • LinkedIn: https://www.linkedin.com/in/rhlockett/ • Website: https://www.lockettcoaching.com *Where to find Lenny:* • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ *In this episode, we cover:* (00:00) Introduction to Rachel Lockett (04:58) The human side of business building (09:00) Coaching vs. advising (13:09) Skill 1: Active listening (18:37) Skill 2: Powerful questions (24:49) Real-life coaching example (27:36) Live coaching example with Lenny (41:55) Addressing burnout in tech (51:03) Spending more time working toward your goals (53:09) Discovering her passion for executive coaching (57:36) It's your job to navigate your career (58:44) Why Rachel says to start small (01:00:49) Building strong co-founder relationships (01:06:50) Handling co-founder conflicts (01:12:35) Improving interpersonal skills with team members (01:20:28) Reframing difficult conversations as growth opportunities (01:31:47) The one-page plan for company alignment (01:36:50) Leveraging AI in coaching and personal development (01:42:04) Lightning round and final thoughts *Referenced:* • One-page plan template: https://www.lockettcoaching.com/#resources • Lockett Coaching Leadership Toolkit: https://www.dropbox.com/scl/fi/s74a9cn1ka1ebz6pglypf/Leadership-Toolkit_-Coaching-Rachel-Lockett.pdf?rlkey=yg2m9df2ziwy0fa6p0dt4gcfu&st=dgzvnf76&dl=0 • Renew Your Co-Founder Vows—and Other Tactics for Strengthening the Most Important Relationship in Your Startup: https://review.firstround.com/five-practices-to-strengthen-your-co-founder-relationship/ • First Round Guide to Co-Founder Check-Ins: https://docs.google.com/document/d/1yUosmfMuE-8-sAwPrEPDcGqkJLVLWg5dC2_8lcXm7U4/edit?tab=t.0 • Coinbase: https://www.coinbase.com • Management Time: Who’s Got the Monkey?: https://hbr.org/1999/11/management-time-whos-got-the-monkey • Chuck Palahniuk’s quote from Fight Club: https://www.goodreads.com/quotes/1338270-people-don-t-listen-they-just-wait-for-their-turn-to • Patrick Collison on X: https://x.com/patrickc • Stripe: https://stripe.com • Remind: https://www.remind.com • Zach Abrams on LinkedIn: https://www.linkedin.com/in/zacharyabrams • Brex: https://www.brex.com • Bridge: https://www.bridge.xyz • Superhuman’s secret to success: Ignoring most customer feedback, manually onboarding every new user, obsessing over every detail, and positioning around a single attribute: speed | Rahul Vohra (CEO): https://www.lennysnewsletter.com/p/superhumans-secret-to-success-rahul-vohra • Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building • The Enneagram Institute: https://www.enneagraminstitute.com • How to build deeper, more robust relationships | Carole Robin (Stanford GSB professor, “Touchy Feely”): https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin • How have I been complicit in creating the conditions I say I don’t want? | Jerry Colonna (CEO of Reboot, executive coach, former VC): https://www.lennysnewsletter.com/p/jerry-colonna ... References continued at: https://www.lennysnewsletter.com/p/a-guide-to-difficult-conversations _Production and marketing by https://penname.co/._ _For inquiries about sponsoring the podcast, email [email protected]._ Lenny may be an investor in the companies discussed.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Lenny Rachitsky?

  When clients come to you, what is the biggest gap they have that is keeping them from being successful as leaders?

• 0:05Speaker 01

  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.

• 0:27Lenny Rachitsky?

  Difficult conversations are difficult. How do we help people make them less difficult?

• 0:31Speaker 01

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

• 0:57Lenny Rachitsky?

  Talk about what you've learned about helping leaders in tech avoid burnout.

• 1:01Speaker 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, 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.

• 1:26Lenny Rachitsky?

  The power of this is this makes your life so much better.

• 1:28Speaker 01

  Honey, let's try it. So I want you to tell me a challenge, something that you're struggling with.

• 1:33Lenny Rachitsky?

  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 of live coaching sessions to demonstrate some of Rachel's approaches.

• 2:15Lenny Rachitsky?

  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. And if you become an annual subscriber of my newsletter, you get a year free of a ton of incredible products, including Devon Lovable, Repli, Bolt In It, and Linear Superhuman, Descript, Whisperful, Gamma, Reflexity, Warp, Granola, Magic Patterns, Raycast, Japier, D-Mob, 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. 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.

• 2:58Lenny Rachitsky?

  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. There's a reason I've had more leaders from Stripe on this podcast than any other company. They know how to build great products that scale and that people love. Stripe is also a lot more than just payments. They've also got a category-leading billing solution and a highly optimized checkout experience built specifically to increase your checkout conversion.

• 3:38Lenny Rachitsky?

  Enterprises like Atlassian, Figma, and Urban use Stripe to create fully branded and customized checkout pages with access to more than 125 global payment methods. Join the ranks of industry leaders like Salesforce, OpenAI, and Pepsi that are using Stripe to grow faster and grow GDP. Learn how Stripe can help your business grow at stripe.com.

• 4:01Lenny Rachitsky?

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• 4:45Lenny Rachitsky?

  productive. Establishing trust isn't optional. Vanta makes it automatic. Get $1,000 off at vanta.com/leni.

• 4:59Lenny Rachitsky?

  Rachel, thank you so much for being here and welcome to the podcast.

• 5:03Speaker 01

  Thank you so much for having me, Lenny. I am honored to be here.

• 5:06Lenny Rachitsky?

  I'm honored to have you here. I was gonna 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. Let me just ask you, what are you hoping people get out of the conversation we're about to have?

• 5:22Speaker 01

  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.

• 5:47Lenny Rachitsky?

  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.

• 5:55Speaker 01

  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.

• 6:22Lenny Rachitsky?

  I think the hardest part of this for people is just, there's like 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's, I don't, that doesn't feel good.

• 6:37Speaker 01

  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. 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.

• 7:20Speaker 01

  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. It'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?

• 7:59Lenny Rachitsky?

  Killing it.

• 8:00Speaker 01

  He's not only killing it, but he's running a community, a global community for Coinbase called Base and the Base App. It's the largest Ethereum L2 in the world. And it's a community of creators and developers. And he's in having a great time, like he's having more fun than ever. And so I think for the people who are committed to excellence and impact. Recognizing that if they lean into their gifts and they get back into their purpose, they can have more fun while having an impact on the world.

• 8:33Lenny Rachitsky?

  This story reminds me 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. You know, 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 them 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 thing, 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

• 9:18Lenny Rachitsky?

  to coach. Talk about what you see there, why this is so important, and how you help people develop the skill.

• 9:24Speaker 01

  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,

• 10:05Speaker 01

  when do I have to have the answer? And when I don't have the answer, what options do I have? 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.

• 10:25Speaker 01

  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. 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,

• 11:07Speaker 01

  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.

• 11:30Lenny Rachitsky?

  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?

• 11:41Speaker 01

  Say more.

• 11:42Lenny Rachitsky?

  Okay, so, okay, we'll link to it. It's this idea that as a leader, people are always just coming to you, trying to give you their monkey that's sitting on their back. And they're like, hey, this monkey's causing me a problem, I don't know what to do about 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.

• 12:03Speaker 01

  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.

• 12:30Lenny Rachitsky?

  So we're gonna, 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?

• 12:42Speaker 01

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

• 13:24Lenny Rachitsky?

  She's gonna love this.

• 13:25Speaker 01

  Or anyone you operate with. And hopefully your listeners can use them too.

• 13:29Lenny Rachitsky?

  Let's do it.

• 13:31Speaker 01

  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." 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

• 14:13Speaker 01

  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 worlds 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. I'm focused on your words. Level three, listening, listening is global listening. So that's when I'm hearing beneath the words and hearing what you're communicating, not just what you're saying. I see your body language. I notice your tone

• 14:58Speaker 01

  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?

• 15:22Lenny Rachitsky?

  Let's do it.

• 15:25Speaker 01

  Okay, how about this? I'll demonstrate some level three listening. I'm gonna ask you a question.

• 15:30Lenny Rachitsky?

  Okay. Uh oh.

• 15:32Speaker 01

  You told me earlier, you're a father.

• 15:34Lenny Rachitsky?

  Yep.

• 15:35Speaker 01

  What is it like to be a dad?

• 15:37Lenny Rachitsky?

  Wow. What is it like to be a dad? Uh, it's amazing. It's like the most amazing thing I've ever done. Uh, 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, it's like everything people tell you it is, and so, and basically in every way, except, uh, the joy is so much higher, so much higher than you hear from other people. Because people always talk about all the, all the downsides, all the pain and challenges.

• 16:15Speaker 01

  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 know, you looked up and down and kind of avoided my eye contact at first. Because my sense is, you love being a dad, and it's so challenging. It's so tiring. And I'm hearing both of that in your answer, like the high joy and the discomfort in having to sleep train and having to disappoint and navigating challenging behavior.

• 16:50Lenny Rachitsky?

  Hmm, uh, nailed it. That was very nice to hear. Uh, clearly you listened to everything I said, and that was a really good example of active listening.

• 16:58Speaker 01

  What, what does it feel like to be seen that way?

• 17:02Lenny Rachitsky?

  It feels really nice. It feels really nice to be, to be heard and, and it's not just like you're repeating back my words. It's here's what I got out of like kind of the level below what you're saying and the gist and the bigger picture.

• 17:13Speaker 01

  Yeah, there's some emotional connection when you listen actively and that took, you know, less than a minute. So what I want to invite listeners to understand is that active listening doesn't mean you're setting up an hour coaching session with every person on your team. No one has time for that. But even in the time you're already spending, just focusing on the other person in a way that is novel and really gives them their, 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.

• 17:49Lenny Rachitsky?

  And there's, I think there's just so much power in just, in different words, repeating back what they said. And that's almost implied in what you're describing. Like 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 gonna show me I keep 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.

• 18:10Speaker 01

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

• 18:18Lenny Rachitsky?

  The emotions.

• 18:19Speaker 01

  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.

• 18:33Lenny Rachitsky?

  Awesome. Okay. So this is a core skill of coaching is active listening.

• 18:37Speaker 01

  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.

• 19:07Speaker 01

  So something that I like to equip leaders with is four kinds of questions that you can ask to unlock insight. So the first kind is, I use a GROW model. So the GROW model just is four different categories of kinds of powerful questions. So the G in GROW is goal. So what does success look like? What's the outcome that you want to have? Any question that's around defining the best case scenario. 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.

• 19:47Speaker 01

  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.

• 20:21Lenny Rachitsky?

  Okay, so just to reflect back what you're saying. So this is, someone comes to you with a monkey on their back. Here's a problem I'm trying to solve. This problem, this person on my team is having, is just like, not doing something right, or this feature isn't working, something like that. So first of all, it's listen, be very, be very active in your listening. Reflect back what you're hearing, their emotions.

• 20:43Speaker 01

  Yeah.

• 20:44Lenny Rachitsky?

  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 hear? 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?

• 21:00Speaker 01

  Yeah, what are your paths forward? What could you do next?

• 21:03Lenny Rachitsky?

  What could you do next? And then, and then you, like I, you know, this is organic. So it's not just like one, two, three, four, I imagine.

• 21:09Speaker 01

  Yeah.

• 21:10Lenny Rachitsky?

  The next, the final step is just, okay, what's the way forward? What do you, what do you want to do?

• 21:14Speaker 01

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

• 21:48Lenny Rachitsky?

  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.

• 21:56Speaker 01

  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.

• 22:19Lenny Rachitsky?

  There's kind of like, this begs the question, what if they just come to a terrible conclusion and you're just like,

• 22:26Lenny Rachitsky?

  advice on when to actually just like, what about this instead?

• 22:30Speaker 01

  Yeah, okay, I think that's great. So if you have a really strong negative reaction to what they're sharing, of course, it's not, 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 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 and your meetings for open-ended questions.

• 23:13Lenny Rachitsky?

  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, your thinking."

• 23:22Speaker 01

  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.

• 23:55Lenny Rachitsky?

  And you may actually be wrong and you may realize, okay, they actually have the better solution. I get it now.

• 24:01Speaker 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

• 24:45Speaker 01

  while still empowering them to solve their own problem.

• 24:49Lenny Rachitsky?

  To close the loop on this piece of advice, is there an example you could share to make this super concrete for folks?

• 24:55Speaker 01

  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.

• 25:21Speaker 01

  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.

• 25:43Speaker 01

  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.

• 25:57Speaker 01

  But he didn't have an engineering manager and a product leader for every one of them. 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 like 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.

• 26:41Speaker 01

  I'm going to align to the KPIs, ask how things are going, ask where they're stuck.

• 26:47Speaker 01

  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 and spend his time in his gifts, which are product vision and strategy. So that's more of a global example of what it what results from you from leaders shifting from the mode of solving every problem to coaching.

• 27:19Lenny Rachitsky?

  That's such a great example of just the power of this is 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, so much changes.

• 27:35Speaker 01

  Exactly. Let's try it. 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.

• 27:50Lenny Rachitsky?

  Whoa.

• 27:52Lenny Rachitsky?

  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, 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, like I have this large Slack community at Twitter and LinkedIn.

• 28:36Lenny Rachitsky?

  So I'm just constantly being barraged with like small little asks and things and all these little things that never, it's hard to just ignore and say no to. So, so what I struggle with is just endless work. I joke that be careful working for yourself if your boss is a workaholic.

• 28:53Speaker 01

  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 like a fun, passion project and you couldn't help but make it this all consuming full-time job.

• 29:26Lenny Rachitsky?

  That's right. Let me just add, it's like in so many ways, the most awesome thing I could ever imagine doing also, and extremely fulfilling, and I couldn't think of anything better I'd rather be doing. So I think that's an important element, but still it's this Indiana Jones boulder constantly chasing me.

• 29:41Speaker 01

  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?

• 29:56Lenny Rachitsky?

  That's one way to put it, yeah.

• 29:58Speaker 01

  I mean, Indiana Jones boulder is coming for you.

• 30:01Lenny Rachitsky?

  Oh, man.

• 30:02Speaker 01

  A fight or flight instinct we all have.

• 30:04Lenny Rachitsky?

  That's true.

• 30:05Speaker 01

  Okay. So, thank you for being vulnerable enough to share that with your listeners and with me. I want to ask you.

• 30:16Speaker 01

  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?

• 30:32Lenny Rachitsky?

  What I imagine is the same thing mostly, just much more free time. Some 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, uh, the boulders may be smaller.

• 30:56Speaker 01

  Yeah, okay. So what is free time enable for you? When you think about, I, I hear your deep commitment to quality products.

• 31:05Lenny Rachitsky?

  Yeah.

• 31:05Speaker 01

  And quality output. But this longing to feel a little bit more playful or flexible with those parts that are essential to you.

• 31:17Lenny Rachitsky?

  Very practically, it's time to play around with, you know, AI tools, just like explore and just kind of tinker versus like, 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 gotta do. Oh, this podcast, gotta prefer that, gotta edit this thing. So it's just time to tinker and explore and, and just like, yeah, that kind of thing, that kind of stuff.

• 31:37Speaker 01

  That makes sense. And what's important about exploring and tinkering to you?

• 31:42Lenny Rachitsky?

  Because in the work I do, I need to stay ahead on where things are going. I can't just, you know, sit around and pontificate from a cloud. I need to really understand how things work, what's, 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, you know, putting out content.

• 31:59Speaker 01

  That makes sense. Your voice is moving really fast. You're, I, I kind of hear you feeling behind, even in the way you're describing what you're doing.

• 32:08Lenny Rachitsky?

  Good active listening.

• 32:10Speaker 01

  What's interesting to me is when you're talking about exploring and tinkering. When you first said it, you said it's in kind of a spacious way. Like 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?

• 32:37Lenny Rachitsky?

  Yeah, uh, yeah, those are two, two sides of the coin. I, there's like another element of, I guess, let me answer that question. I think, I think those are both true. I don't know. Cause it's actually like, the reason I got into this is because it was so fun and so interesting. Just like, here's what's happening. Here's what the future. There's advice, here's ways to improve in the work that you do. So there's still, like, I still love it. It's just I have less time to do that part and more. It's just like the machine of the treadmill of content, content, content.

• 33:04Speaker 01

  Yeah.

• 33:05Lenny Rachitsky?

  There's also just like spending more, like, I didn't even mention this, but just spending more time with my son and my wife, you know? That would be really great. Just have more freedom to go, go do stuff, which we have a lot of that, but.

• 33:16Speaker 01

  That makes sense. Okay, so the, the goal that I hear is not so dramatically different from today. It's that you hold on to this high quality output. You have space for exploring and tinkering and for spending quality time with the people you love most.

• 33:33Lenny Rachitsky?

  Yes. The one way I'm thinking about as you reflect that back is like 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.

• 33:49Speaker 01

  Yeah, there's that inertia of moving fast, taking advantage of the moment that's coming.

• 33:53Lenny Rachitsky?

  Yeah, yeah.

• 33:54Speaker 01

  So that's a perfect shift into, um, what are your current ways of operating that get in the way of having that 25% of free time?

• 34:03Lenny Rachitsky?

  It's just like agreeing to more things, just like, oh, look, I'm kind of free right now. Oh, okay, let's do this, uh, let's do this talk here. Let's agree to this thing here. It's 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.

• 34:17Speaker 01

  Yeah. And how is that commitment to saying yes to things that come at you, serving you?

• 34:24Lenny Rachitsky?

  Not great.

• 34:26Speaker 01

  Well, it's serving you in some ways. Like, you're doing it for a reason. What benefit does it have to you?

• 34:33Lenny Rachitsky?

  Well, it depends on the thing. You know, like, I actually have a rule of never doing a talk, or going on other podcasts, 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.

• 34:56Speaker 01

  Yeah, that's smart.

• 34:57Lenny Rachitsky?

  So yeah, it's your point. There's value here and there when I take on more work, but and then I end up overworked again.

• 35:04Speaker 01

  Yeah, I'm hearing there's just a pattern. It's like a reflexive pattern of even though you set a rule for yourself to say no to certain things, and you seem proud of that boundary, you naturally break it, or you fall into filling it with other things.

• 35:16Lenny Rachitsky?

  That's right. Exactly.

• 35:18Speaker 01

  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.

• 35:34Speaker 01

  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?

• 36:00Lenny Rachitsky?

  Something I've already done, which hasn't kicked in fully yet, but that I'm really excited about, is I reduced the cadence of my newsletter and podcast, which in theory should be a massive change, but the podcast hasn't, 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 will receive a newsletter every week, now it's two to four times a month, depending on what's going on, 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, things happening, I gotta put this out. So I'm almost not taking advantage of that opportunity. So something I could do is actually not publish every week.

• 36:45Lenny Rachitsky?

  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.

• 36:56Speaker 01

  Yeah.

• 36:57Lenny Rachitsky?

  But I'm always thinking about, and I should think deeper about where can people take more load off my plate.

• 37:03Speaker 01

  Yeah, I love that insight. If you, 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. You may have limiting beliefs around the things you need to do versus the people on your team.

• 37:21Lenny Rachitsky?

  I might, I might. And then your point I loved, which is just say, improve my policies of what I say no to that don't serve me.

• 37:29Speaker 01

  Yeah. What are the things you could be saying yes to if you said no to more things?

• 37:34Lenny Rachitsky?

  Just playing around with stuff, just space to explore and tinker and just sit around and think versus just go, go, go, go, go.

• 37:43Speaker 01

  Yeah, and I hear, I just see you feel so light and excited in that, like you almost are giddy when you think about that spaciousness.

• 37:50Lenny Rachitsky?

  That'd be so nice.

• 37:51Speaker 01

  And I just want to name, reflect back to you how special that is and how much more creative you could be in your work when you have that space and time and your bucket's full with care.

• 38:03Lenny Rachitsky?

  I feel that, I feel that.

• 38:04Speaker 01

  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?

• 38:14Lenny Rachitsky?

  I love that we're like, as we go through this, I'm like, thinking about this growth framework and I love how you're executing. Like I see you in action.

• 38:21Speaker 01

  Yeah, I'm trying to do very simple coaching right now.

• 38:23Lenny Rachitsky?

  Yeah, yeah, this is great.

• 38:25Speaker 01

  That it's really easy to follow for your listeners.

• 38:28Lenny Rachitsky?

  Yeah, this is great. Uh, 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. So, but it's tough because the next two weeks I got already planned. I got to write, 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 gonna revisit my policies on what I say yes and no to.

• 38:58Speaker 01

  I love that. Think about everything you're saying yes to, and what are things you want to say yes to that you could trade 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.

• 39:20Lenny Rachitsky?

  I love just that element of here's what you will 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.

• 39:27Speaker 01

  Exactly. Yeah. Say like a resonant, full bodied yes to the things that are

• 39:30Lenny Rachitsky?

  Hell, yes.

• 39:32Speaker 01

  Yeah. Hell, yes. With an exclamation. Exactly. Okay. 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 know, 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, urgent, but the same kinds of questions unlock

• 40:16Speaker 01

  new opportunity when it's about how to build technical infrastructure, or how to, you know, influence the executive team, or how to ship the go to market strategy. So I just want a name that's very transferable.

• 40:29Lenny Rachitsky?

  I love that I got. Great advice in this conversation already. How, what a great ROI for me at least.

• 40:37Speaker 01

  What did it feel like to be coached on your own podcast?

• 40:39Lenny Rachitsky?

  It was, it was unusual. I'm just like, wait, I gotta get back to asking you questions.

• 40:44Speaker 01

  Okay, all right, all right. We can flip, we can flip. I, I do wanna name that typically when you're coached versus told what to do, you're more bought in. So if I told you, you know, 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 gonna delegate. You know, 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.

• 41:21Lenny Rachitsky?

  I, I was gonna mention that earlier. That is so incredibly true. Like, no one wants to. Like, unless you ask for advice, very few people are like, please tell me what to do. Just tell me. I really love you. Just unsolicited advice. Like, it doesn't go well.

• 41:35Speaker 01

  Yeah, and great leaders often say, do you want advice or do you want some space to think about it? Like, can I, you know, can I help you think it through or would you like me to tell you what I would do? And both are fine in certain situations. So asking is useful too.

• 41:48Lenny Rachitsky?

  Yeah, okay. That was a, that's such an important element of this that I, we should have mentioned and that's, I'm glad you did.

• 41:54Speaker 01

  Yeah.

• 41:55Lenny Rachitsky?

  Okay, so I'm gonna go back to asking you questions.

• 41:58Speaker 01

  Right.

• 41:59Lenny Rachitsky?

  This is a good segue to something I wanted to spend a little time on, which is burnout.

• 42:03Speaker 01

  Yeah.

• 42:04Lenny Rachitsky?

  We, you know, what I'm talking about is stuff that often leads to burnout. I'm definitely not burnt out, but you know, this is a, a common problem in tech. Where people feel depleted and just go too hard and then they, so many people I've worked with just left tech. I had a colleague get Airbnb, he went, he's like a park ranger now in the New York Woods. And that's how far.

• 42:24Speaker 01

  Peaceful.

• 42:25Lenny Rachitsky?

  So peaceful and so wonderful, but I think that's just people go so hard sometimes and then just get burnt out and never wanna 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.

• 42:46Speaker 01

  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 Carlson 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. 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.

• 43:30Speaker 01

  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. So I've also witnessed people who are still inspired and continually energetic and seem to have some secret well of, you know, 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 my, what I make of that is that when people are in their gifts and their strengths firmly,

• 44:13Speaker 01

  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. So I try to help my leaders see that they can, 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 an executive at a huge company.

• 44:44Speaker 01

  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. So one tool I like to give is for people to actually take two weeks and every night reflect on what's the five, what are the five things today that gave you the most

• 45:28Speaker 01

  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.

• 45:52Lenny Rachitsky?

  I so believe this advice is so effective. This is the way I actually approached 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 more, less of the thing that saps me. I want to talk about just like, you know, there's only so much you can change, but I want to talk about that.

• 46:15Speaker 01

  Yeah.

• 46:15Lenny Rachitsky?

  And that, and so initially I was like, maybe I'll become an advisor and consultant kind of person. I actually found that was super depleting for me.

• 46:22Speaker 01

  Interesting.

• 46:23Lenny Rachitsky?

  Doing these calls and talking to people, because it's like surface level, you know, here are some things I would do. And it was just so unexciting and energizing, but writing was really energizing, which I never expected.

• 46:34Speaker 01

  And I love that.

• 46:35Lenny Rachitsky?

  And that's what I did, and I just followed that pull.

• 46:37Speaker 01

  And it sounds like maybe you need a refresh, Lenny.

• 46:42Lenny Rachitsky?

  Oh, interesting.

• 46:43Speaker 01

  You know, there's always more attuning you can do to your gifts. Like 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 kind of tuning in to where your spark is and protecting that spark, feeding it.

• 47:04Lenny Rachitsky?

  I love that insight. That just blew my mind. So very tactically, the way you would do this is for two weeks every night is the idea. Look at reflect back on that day and write down five things that gave you energy, five things that stop you of energy.

• 47:19Speaker 01

  Yeah, there's so many different activities you could use. So that's one. I like an activity of actually asking five to 10 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, when do you have the most inspiration?

• 47:46Speaker 01

  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 kind of 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.

• 48:14Lenny Rachitsky?

  Is there any advice for actually doing this? Say someone's just like, yeah, I've got to do this, but you know, most people don't actually do this. Is there like a buddy you can nominate? Just help me do this. Is it like, if you have any EA that can maybe help you with this? Is there anything you've seen?

• 48:28Speaker 01

  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 ahead of HR, but I love working with leaders. So I'm gonna, you know, 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. And so when this opportunity to work on top talent retention came about, it was much very aligned in, in the realm of coaching and L and 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?

• 49:12Speaker 01

  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. When you're a founder or 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, 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

• 49:53Speaker 01

  honest about your strengths and your weaknesses, then you can start to manage around them.

• 49:58Lenny Rachitsky?

  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.

• 50:42Lenny Rachitsky?

  This is why leading platforms like Etsy, LinkedIn, Square and Lyft trust Persona to secure their platform. 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. It's really nice to know what you want to do and understand where 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 in their gifts, to actually not just be like,

• 51:23Lenny Rachitsky?

  like there is, you have agency to move in a direction that'll make you happier.

• 51:28Speaker 01

  Absolutely.

• 51:28Lenny Rachitsky?

  It's kind of an implied piece of this.

• 51:30Speaker 01

  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?

• 51:52Lenny Rachitsky?

  And telling your manager, I think, is such a simple and important part of this. Telling them, 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?

• 52:04Speaker 01

  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. And that, 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.

• 52:37Lenny Rachitsky?

  What's like a good percentage of your work life that should be in gifts? And things that energize you versus, okay, I actually got to do some stupid stuff.

• 52:46Speaker 01

  My fitness test is 80%, that's the goal, 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. 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.

• 53:16Speaker 01

  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 in to 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. I, you know, came into the team. There was, I think, 12 senior engineers, very opinionated, very skeptical of 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?

• 54:01Speaker 01

  What's working and not working? And within a month, this team was working well together. They were, you know, 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's working. But what I was also doing is 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.

• 54:44Speaker 01

  And he was listening to me ask all these questions about how to sell the vision of what this, what this product would look like in the future. 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.

• 55:17Speaker 01

  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. 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.

• 56:02Speaker 01

  And we've both been honing our gifts. And it's, 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 wake-up call for people to really think about what is their spark? And to protect it and to feed it.

• 56:35Lenny Rachitsky?

  I love that story because I think most people when they hear this advice and this kind of topic of, okay, I'm 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, there's actually, 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. Hey, here's something, like, 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 like sucking and then like, oh, but I want to work on strategy.

• 57:18Speaker 01

  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 it's that, 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?

• 57:53Lenny Rachitsky?

  This reminds me, there's a couple of guests I've had on the podcast who did this. They're both founders, so it's, you know, this is specific to founders, but Rahul Vohra at Superhuman, he realized he's just not, he's not like the best executor in the operations person, so he hired a president that took all that office plate. And then Dharmesh, 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.

• 58:23Speaker 01

  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, oh, I don't want to have any one on ones. But just not having anyone manage those people is not going to be healthy for your company. So you have to both take your strengths seriously and actively manage around your weaknesses.

• 58:44Lenny Rachitsky?

  Is there any, maybe the 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?

• 58:52Speaker 01

  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, to go 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 like plug up that gas leak and

• 59:21Speaker 01

  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.

• 59:41Lenny Rachitsky?

  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.

• 59:48Speaker 01

  I agree. I love, I love a physical book. I have a Kindle. I got all the things, but a physical book on the couch is the best.

• 59:55Lenny Rachitsky?

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

• 1:00:38Speaker 01

  Exactly.

• 1:00:39Lenny Rachitsky?

  And then you not working well together is just a huge issue because that all trickles down and everyone sees it. And, and you know, 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?

• 1:00:55Speaker 01

  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,

• 1:01:38Speaker 01

  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. 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. And I think that the core, at its core, what you need in a healthy relationship is one, self-awareness. What do I bring into this dynamic?

• 1:02:21Speaker 01

  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? A very classic one has to do with roles. CTOs tend to be skeptics. They're, 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.

• 1:03:06Speaker 01

  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, 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. The second step is actually being conscious about the commitment you're making to your relationship. So in a marriage, for example, people, you know, I, I, I talk about co-founder vows and recommitments and renewals.

• 1:03:47Speaker 01

  Because in a marriage, you get married and a lot of the times people build a family. And then they think, oh, the relationship will just continue because we're 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? 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.

• 1:04:32Speaker 01

  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.

• 1:04:45Speaker 01

  That space is critical for the health of a co-founder relationship.

• 1:04:49Lenny Rachitsky?

  On that second piece, the vows idea is such a good idea. Is that something you actually recommend? Like, here's what I vow to do?

• 1:04:55Speaker 01

  Yeah, here's what I commit to do. So I have, recently, I actually wrote an article with First Round. And we created a document to help co-founders think about what to integrate into their check-in. So we put out weekly check-in, monthly check-in, and annual, and just questions to sit down and ask each other. Active listening skills will come in handy in those conversations. But it's about taking space out of hustling and running the business to think about the business from a kind of, rather, I, I like to say, instead of being on the dance floor, you need time on the balcony to look down at what's happening. How are we doing? Is this still working for both of us? And the vows are really about, how are we gonna be together?

• 1:05:41Speaker 01

  How are we gonna show up? Like, what's our culture that we're creating? Even if you don't want to go through a whole culture exercise early on in building your company, you should have some sense of how you want to show up for each other. How are we gonna make decisions?

• 1:05:55Speaker 01

  How are we going to deal with conflict? These are things you can go to go into intentionally and design with your co-founder.

• 1:06:03Lenny Rachitsky?

  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.

• 1:06:12Speaker 01

  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 the... 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.

• 1:06:50Lenny Rachitsky?

  What do you recommend people do when they are just like, our relationship isn't working great? Like, there's a lot of tension. All this advice we've been talking about is like, 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 just like, it's really annoying. I don't like this person that much. There's so much tension constantly. What are a couple of things they can do this week, next week?

• 1:07:26Speaker 01

  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 co-founder. 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

• 1:08:05Speaker 01

  fast. And at one point when they started, you had the visionary who was great at selling business. They were both incredible with PR. And the partner was incredible operationally. So as the business scaled, one took on a lot more business development and the other took on all the internal things, but was exhausted by all this people management and all of the elements of kind of running a scaled team that she didn't expect to have to do. And when they came, I think both of them weren't sure, can we figure this out? Do we want to just sell this thing? Do we want to keep going? And I think someone said,

• 1:08:46Speaker 01

  end it or send it, was what one co-founder said to me. You know, 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. 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

• 1:09:28Speaker 01

  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 an important start to their healing. And over our coaching, they turned back towards each other and they created more of a rhythm of how they would get together without me involved. And they 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.

• 1:10:12Speaker 01

  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. And after that conversation, it was really clear that that one of the co-founders was unhappy and 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.

• 1:10:56Speaker 01

  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.

• 1:11:15Lenny Rachitsky?

  I love how similar this is to just a marriage. All this stuff here, like this is the same sort of thing you do.

• 1:11:20Speaker 01

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

• 1:11:51Lenny Rachitsky?

  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. Like, there's only so far you can get just talking.

• 1:12:01Speaker 01

  It it takes an evolved facilitator, like one of the co-founders being able to hold space for both their frustration and their empathy.

• 1:12:12Speaker 01

  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.

• 1:12:35Lenny Rachitsky?

  Outside of the co-founder relationship, do you have any just tactical tips for people to improve their interpersonal 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.

• 1:12:50Speaker 01

  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

• 1:13:35Speaker 01

  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. So I'm going to give you a framework that I like, that many of my clients use. It's from Marshall Rosenberg's Nonviolent Communication. He has a book and a framework. So it's four steps. The first step is observations. So my job is to note what is happening factually.

• 1:14:16Speaker 01

  For example, I noticed that in the last three sprint planning meetings, you didn't show me what you were, 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.

• 1:14:34Speaker 01

  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. 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.

• 1:15:16Speaker 01

  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. Now, the other person doesn't have to meet my request.

• 1:15:57Speaker 01

  They might make a counterproposal, but the most important thing of this model and this conversation is that the other person understands what I'm going through and they don't feel reactive so that we can have a mutual conversation about what's going on.

• 1:16:12Lenny Rachitsky?

  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.

• 1:16:32Speaker 01

  Lenny, try this with your wife tonight. NBC is a powerful tool. And actually, it's very akin to most models that are about connection.

• 1:16:42Speaker 01

  The Stanford Business School course that has a T, it's called Touchy Feely that everybody loves.

• 1:16:47Lenny Rachitsky?

  We've had Carol on the podcast.

• 1:16:49Speaker 01

  Great. Yeah. So Carol Robbins created this movement, right? There's lit, a lot of founders go to her model that's for founders.

• 1:16:55Lenny Rachitsky?

  And tech, yep.

• 1:16:56Speaker 01

  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.

• 1:17:21Lenny Rachitsky?

  Yeah. So what I was going to say as you were going through this framework is it's all, it's here's me, here's what I saw, here's what I'm feeling, here's what I need. And then here, 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.

• 1:17:36Speaker 01

  Exactly. It also acknowledges that professionals have feelings. I think that we operate in tech, like we're supposed to give all of ourselves, all of our time, all of our energy to this endeavor. And it's purely logical. 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.

• 1:18:01Lenny Rachitsky?

  And there's kind of 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. It's, 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.

• 1:18:21Speaker 01

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

• 1:19:00Lenny Rachitsky?

  Let me remind folks of the framework. I'm going to try using this. I wish it was a handy acronym.

• 1:19:06Speaker 01

  I know.

• 1:19:07Lenny Rachitsky?

  Offner. So the framework is share what you've observed, just the facts of what is happening. Just simply, here's, I saw you then close the fridge fully. Your feelings of how that made you feel, the needs that, your core human need that derives that feeling, I imagine. And then the request you have of the person.

• 1:19:28Speaker 01

  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.

• 1:20:05Lenny Rachitsky?

  Are there, there are like phrases that are just examples of non-feelings? Like, like, like, like using the word "you" in the way you describe a feeling probably is not a good, not a good sign.

• 1:20:14Speaker 01

  Exactly. If you can say like, 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.

• 1:20:24Lenny Rachitsky?

  So don't say like, don't say you, don't say that.

• 1:20:27Speaker 01

  Yeah, exactly.

• 1:20:28Lenny Rachitsky?

  Awesome. Sort of along this topic, I, 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 helped 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.

• 1:20:52Speaker 01

  Oh, wow, I love that.

• 1:20:54Lenny Rachitsky?

  So she said, Rachel is exceptional making difficult decisions clear and making it feel possible to get 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?

• 1:21:11Speaker 01

  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.

• 1:21:54Speaker 01

  And there's something to learn from it. So first, I want leaders who are listening to think, this is hard because I have something to learn here and because it matters. So instead of avoiding it and running away, I'm going to lean into this moment. And I'm going to come out of it, not just having solved this dynamic and not just having said my piece, but having built a skill. 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.

• 1:22:37Speaker 01

  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 to think of them as a growth opportunity. Second, there is always something that we're doing to contribute to the conflict, even if it feels like the other person's insane and is driving us crazy and we're the innocent party.

• 1:23:09Speaker 01

  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, NBC or otherwise, can fix a person who's coming in rigid and full of blame. I really love the 15 commitments to conscious leaders. I don't know if you know that book, but one of the concepts is about taking 100% responsibility, not being in the

• 1:23:48Speaker 01

  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 gonna do it for them and forget it. You know, they're so, they're having such a hard time getting this done, I'm just gonna do it. Instead, take responsibility for your part. What is my piece in making this dynamic happen? And how can I address it?

• 1:24:18Lenny Rachitsky?

  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 the, creating the conditions that you claim you don't want?

• 1:24:29Speaker 01

  Yes, I love that. Love that question.

• 1:24:31Lenny Rachitsky?

  And there's so many, like, 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, 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?

• 1:24:58Speaker 01

  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. Like, 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. For example, I was working with a CEO whose co-founder was constantly undercutting his decisions and criticizing him. And there was something happening where they'd gone from being this great, dynamic duo, fundraised, hired a few leaders, and then all of a sudden, he was getting kind of daggers thrown at him all the time. And it was exhausting and frustrating

• 1:25:41Speaker 01

  and confusing. So that was a time where he used NBC to address, what is happening here? And it turned out that the co-founder was really frustrated with how he was spending his time. He didn't want him to be off selling. He wanted him to be helping him with product vision. And they had a totally different conception of how the CEO should be spending his time.

• 1:26:02Lenny Rachitsky?

  Awesome. Just to remind folks of the NBC framework, because this is the thing that's hard in the moment, like, oh, what should I be saying? Observe, Feelings, Needs, Request.

• 1:26:11Speaker 01

  Yeah, exactly. And there's a, there's a nonviolent communication book. If folks are into the framework and want to check it out.

• 1:26:17Lenny Rachitsky?

  People need a little, like, who is it you said, when your client's tattooed, there is the vision he had on? Okay, there's, let's just get some.

• 1:26:23Speaker 01

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

• 1:26:29Lenny Rachitsky?

  All right, all right. 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.

• 1:26:39Speaker 01

  Yeah.

• 1:26:39Lenny Rachitsky?

  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 it's almost, and the advice there is just, the thing you're afraid of is a compass to the thing you should do, because there's something important there.

• 1:26:59Speaker 01

  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. And when we really take space to think about their feelings and needs, they realize, I asked them, would you enthusiastically rehire this person for the same role? Which is the question we always ask at Stripe. And when the answer is no to that,

• 1:27:44Speaker 01

  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.

• 1:28:01Lenny Rachitsky?

  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?

• 1:28:18Speaker 01

  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 an immediate reaction that is honest to that question that provides clarity.

• 1:28:33Lenny Rachitsky?

  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, right? It doesn't mean like you have to fire them immediately. So it's not necessarily as scary as it sounds if you say no.

• 1:28:47Speaker 01

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

• 1:29:28Lenny Rachitsky?

  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, build a company that actually works out really well, you need to really only hire people around that are hitting that bar.

• 1:29:50Speaker 01

  Yeah, my perspective, you know, I talked at the beginning about how I'm obsessed with the human side of business building. And my belief is that talent and the environment that you put your talent in is everything. Yes, building a product 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, right? 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 writing a timing wave and you're solving a core need. But everything besides that is so human. It's about talent and it's about the environment that you put that talent in.

• 1:30:31Speaker 01

  So you need to create the conditions such that your talent can thrive.

• 1:30:36Lenny Rachitsky?

  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.

• 1:30:48Lenny Rachitsky?

  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 an easier, more motivating way of approaching something that's difficult.

• 1:31:05Speaker 01

  Yeah, and I want to just, 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.

• 1:31:48Lenny Rachitsky?

  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 how 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.

• 1:32:17Speaker 01

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

• 1:33:03Speaker 01

  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.

• 1:33:14Speaker 01

  So I actually got this idea of the one-page plan from Alpine Investors. They do a one-page, 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?

• 1:33:58Speaker 01

  It's always in tandem with your core KPIs, your strategy and your vision.

• 1:34:04Speaker 01

  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.

• 1:34:29Lenny Rachitsky?

  We're gonna hopefully link to a template of this one-page plan?

• 1:34:33Speaker 01

  Yeah, sure. Happy to share.

• 1:34:34Lenny Rachitsky?

  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?

• 1:34:41Speaker 01

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

• 1:35:25Speaker 01

  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. I really like the question, what's an inconvenient truth?

• 1:36:00Speaker 01

  Are the things that need to be talked about that no one's talking about because you're too busy. That's the power of combining a simple plan, whether it's one page or not, that aligns you from the top to the bottom, your vision, all the way down to your quarterly goals, and a time where you stop, pause, discuss, reflect, have a little spacious energy. It's not unlike what you said about your own time. You're, 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.

• 1:36:44Lenny Rachitsky?

  By the way, Alpine investor is Graham Weaver. He was on the podcast.

• 1:36:47Speaker 01

  I saw that. I saw that.

• 1:36:49Lenny Rachitsky?

  I love that. Okay, final, final question. I want to take us to AI corner before we get to a very exciting lightning round. I'm going to do kind of a tweet version. Usually 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, you know, as a coach, but also just from a client's perspective? How are people using AI to help them in their, in their, I guess, life from a coaching perspective?

• 1:37:13Speaker 01

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

• 1:37:23Lenny Rachitsky?

  One free year of granola if you become an annual subscriber of Lenny's newsletter.

• 1:37:26Speaker 01

  There you go. So I, I use granola to take notes in our sessions. 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.

• 1:38:08Speaker 01

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

• 1:38:50Speaker 01

  Finally, and I'm experimenting with AI in a way to support my clients between sessions. So I've gotten some feedback from my clients that they would like more interaction between our sessions. And they're always allowed to email me or text me. I'm available to them, but I think they want to be really respectful of my time. And so some people do reach out and ask me questions and other people wait for our session. So I'm curious about the future of coaching. How in between sessions, clients can get access to more of an AI support? Where they, the bot has all of their context, their development plan that we create at the beginning.

• 1:39:34Speaker 01

  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, 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 it, personal coaching as.

• 1:40:03Speaker 01

  Still critical for what is your vision of your life? How do you want to shift your core behavior to align with that vision? But that AI can play a real helpful role in between on the tactics.

• 1:40:15Lenny Rachitsky?

  That is super cool. So that's something you already do where they have access to this kind of

• 1:40:18Speaker 01

  It's something I'm building right now. I don't have that yet.

• 1:40:22Lenny Rachitsky?

  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, all the frameworks that you use. That is extremely cool. All right, there's a billion dollar company coming.

• 1:40:38Speaker 01

  I don't want to build that.

• 1:40:41Lenny Rachitsky?

  It's not your, it's not your zone of genius.

• 1:40:44Speaker 01

  Exactly.

• 1:40:47Lenny Rachitsky?

  Rachel, is there anything else that you want to share or leave listeners with before we get to our very exciting lightning round?

• 1:40:55Speaker 01

  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'm 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

• 1:41:37Speaker 01

  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.

• 1:42:02Lenny Rachitsky?

  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?

• 1:42:10Speaker 01

  I am ready.

• 1:42:11Lenny Rachitsky?

  First question, what are two or three books that you find yourself recommending most to other people?

• 1:42:15Speaker 01

  One of them I said before, The Fifteen Commitments of Conscious Leaders.

• 1:42:21Speaker 01

  And I love Designing Your Life by Bill Burnett.

• 1:42:23Lenny Rachitsky?

  Hmm, I love that book too. People don't talk about that book enough.

• 1:42:26Speaker 01

  Mm hmm.

• 1:42:28Lenny Rachitsky?

  Uh, next question, favorite recent movie or TV show you've really enjoyed?

• 1:42:31Speaker 01

  Oh, God, I just went to K-pop Demon Hunters with my daughter. It's so embarrassing. But that's what we dress as for Halloween, like everyone else in the world.

• 1:42:38Lenny Rachitsky?

  I've not seen that. I hear everyone talking about it. I'm gonna try to avoid it, I think. Next question, favorite product you have recently discovered they really love? Could be an app, could be a gadget, could be clothes.

• 1:42:48Speaker 01

  I really love Loom.

• 1:42:50Lenny Rachitsky?

  Hmm.

• 1:42:51Speaker 01

  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.

• 1:43:01Lenny Rachitsky?

  Do you have a favorite life motto that you often come back to in work or in life?

• 1:43:06Speaker 01

  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.

• 1:43:18Speaker 01

  Your own path you make with every step you take, that's why it's your path. That's a Joseph Campbell quote.

• 1:43:25Lenny Rachitsky?

  Hmm. Beautiful. Final question, you've got two kids, you said. Do you have any favorite children's books? The you most love reading to them that they've loved most?

• 1:43:35Speaker 01

  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.

• 1:43:54Lenny Rachitsky?

  Have you seen the Wes Anderson stories of his stories?

• 1:43:57Speaker 01

  Some of them, yeah, they're great.

• 1:43:59Lenny Rachitsky?

  Yeah, they're so amazing. Oh, my God. And it's like Roald Dahl is like they, I think it's personifying him like he's like a character in the story.

• 1:44:06Speaker 01

  Yeah, I mean, he's a character from what I hear about his life.

• 1:44:09Lenny Rachitsky?

  Rachel, this was incredible. I feel like we've very much accomplished what I set out to do is just give people all this advice that they never have access to that costs tens of thousands of dollars. Uh, I think we're gonna help a lot of people improve their lives and their careers. Uh, thank you so much for being here.

• 1:44:26Speaker 01

  Absolutely. Thanks for having me.

• 1:44:28Lenny Rachitsky?

  Uh, I almost forgot to ask you two final questions. Where can folks find me if they want to reach out, maybe consider working with you? Uh, and how can listeners be useful to you?

• 1:44:36Speaker 01

  Yeah, find me at lockettcoaching.com.

• 1:44:39Speaker 01

  And how can listeners be useful? Listeners should turn towards each other, build great relationships, and send CEOs and co-founders my way if they need coaching.

• 1:44:47Lenny Rachitsky?

  Thank you so much for being here.

• 1:44:50Speaker 01

  Thanks for having me. Take care, Lenny.

• 1:44:52Lenny Rachitsky?

  Bye, everyone.

• 1:44:54Lenny Rachitsky?

  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. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.