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

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

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.

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

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

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

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.

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

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

The main thing I struggle with these days is just today. My guest is Rachel Lockett, an executive coach and former longtime HR leader at Pinterest and at Stripe. She works with CEOs and founders and leaders at tech companies on both ways that they are emotional and positive, intelligence, resilience and courage. And what they do, setting vision and strategy, prioritizing and building trusted and accountable teams. She's someone I've heard a lot about over the years from other podcast guests, and this conversation is powerful. It's jam packed with advice and tips and frameworks that'll make you a better leader and also a better person. We even do a couple live coaching sessions to demonstrate some of Rachel's approaches. And as you'll see, I had a number of epiphanies during this conversation. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. It helps tremendously. And if you become an annual subscriber of my newsletter, you get a year free of a ton of incredible products including Dev and Lovable, Replit, Bolt in It and Linear, Superhuman, Descript, whisperflow, Gamma Perplexity, Warp, Granola, Magic Patterns, Raycast, Chapier, D Mobin, and Stripe Atlas. Head on over to Lenny'snewsletter.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. 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 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. 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@swepe.com My podcast guests and I love talking about craft and taste and agency and product market fit. You know what we don't love talking about Sock two. That's where Vanta comes in. Vanta helps companies of all sizes get compliant fast and stay that way with industry leading AI automation and continuous monitoring. Whether you're a startup tackling your first SoC2 or ISO 27001 or an enterprise managing vendor risk, Vanta's trust management platform makes it quicker, easier and more scalable. Vanta also helps you complete security questionnaires up to five times faster so that you can win bigger deals sooner. The result? According to a recent IDC study, Vanta customers slashed over $500,000 a year and are three times more productive Establishing trust isn't optional. Vanta makes it automatic. Get $1,000 off@vanta.com Lenny. Rachel, thank you so much for being here and welcome to the podcast.

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

I'm honored to have you here. I was going to start with a different question, but we were chatting ahead of this conversation and I always like to ask guests, what do you want people to get out of this conversation? And I loved your answer. So I just want you to share this. Let me just ask you, what are you hoping people get out of the conversation we're about to have?

Genuinely, I hope that your listeners take away that the human side of business building is incredibly fun and impactful and that it. 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.

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.

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.

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.

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 the 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. And he talked about this dream of creating a global movement one day. He was really focused on building community and he thought the path for creating possibility in the world around him was creating a strong community around him. And he continually worked on his leadership capacity. And over the 10 years, at some point he created a tattoo on his arm that's a sun with a redwood grove around it that reminded him of his core strengths and his purpose. And today, guess what he's doing, Lenny?

Killing it.

He's not only killing it, he's running a community, a global community for Coinbase called Base and the Base app.

Oh, wow.

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

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

I think that most leaders, especially technical leaders, assume they have to have all the answers. People have climbed the ladder in whatever realm they're in because they've been dependable, reliable, the smartest person in the room. But when you're leading a quickly scaling company, you quickly have less context than the people you're around. And the way you were operating before doesn't work because you don't have the ability to wrap your Arms around every problem in a deep way. So I've seen leaders at every phase, from frontline managers up to running an 8,000 person company struggle with knowing when do I have to have the answer and when I don't have the answer, what options do I have? But great leaders know that when you try to advise and have the answer all the time, you're not actually equipping your team to go solve the hard problems. You're training your team to come to you with all of the hard problems. And coaching is a different way. It's an alternative path that unlocks brilliance in your team and is way more motivating for the people around you. So coaching is actually a learnable skill, obviously, because there's tons of coaches around Silicon Valley. But you don't have to coach in the same way that an executive coaches. You can shift your energy into curiosity when someone brings you a hard problem to solve and create space to get curious and help them solve their own problem. So obviously sometimes advising is the right path. If there's an urgent issue, the person coming to you doesn't have the skill they need. That's a time to advise and help. But leaders over rotate assuming the people that they've hired who are experts in their domain need them to solve the problem. So I think it's useful for your listeners to actually know that coaching's an alternative. And I can help them learn some basic skills around this.

Okay, I'd love to learn those skills. What this makes me think about is there's this famous Harvard Business Review piece. I don't know, it's like 30 years ago maybe about the monkey on the back. You know this piece?

Say more?

I think so. Okay, we'll link to it. It's this idea that as a leader, people always just coming to you, trying to give you their monkey that's sitting on their back and they're like, hey, this monkey's causing me all this problem. I don't know what to do. But this monkey, here you go, you take it and feed it and help it figure out what it needs. And the role of a leader is to keep the monkey on the back of the person and help them figure out how to solve the problem. Exactly what you're describing.

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 those questions so that they can solve their own problem.

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?

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

Let's do it.

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 you're talking to me about a problem. I'm thinking about the implications of that problem on me. I'm completely distracted with my own inner dialogue. That's level one. Most people go through their world rushed and in level one, Level two, listening is focused. So you're talking to me, and I can repeat back what you're saying. So I am listening to the words you're describing. And that's typically what happens in a good one on one. We're problem solving together. I'm focused on your words. Level three, 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 of voice. I know the context around what you're talking about, and I can reflect back more insight about what's happening than you're aware of because I'm understanding everything you're communicating. So dropping into level three listening is what great leaders do when they're influencing, when they're selling, when they're pitching a vision, and definitely when they're coaching. So do you want to try it?

Let's do it.

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

Okay.

Oh, you told me earlier you're a father.

Yeah.

What is it like to be a dad?

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

Nailed it. That was very nice to hear. Clearly, you listened to everything I said, and that was a really good example of active listening.

What does it feel like to be seen that way?

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

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.

And there's. I think there's just so much power in just in different words, repeating back what they said 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 going to 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 the subtle.

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

The emotions.

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.

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

Yes. So that's listening. Second skill, powerful questions. So asking powerful questions means I'm curious about what's really going on, and there's not one right answer. So a powerful question helps you gain insight, and it takes you to a new solution set you didn't have before. But it's not me leading the witness. I'm not trying to guide you to a specific answer. That wouldn't be a powerful question. So something that I like to equip leaders with is four kinds of questions that you can ask to unlock insight. So the first kind is. Is I use a grow model. So the grow model just is four different categories of kinds of powerful questions. So the G in grow is goal. So what does success look like? What's the outcome that you want to have? Any question that's around defining the best case scenario. The R in the grow model is about your current reality. Where are you stuck? What are your current challenges? What have you tried? The O is about your options. So let's Expand the opportunities that you can understand of the choices you have in front of you. What are the various paths you could take? And the W in the grow model is the way forward. What are you going to do next? So this sounds simple and it is simple. If you take the time and space to listen carefully and ask any of these questions, the people on your team will appreciate the space and time to unlock an option that they didn't think of before and walk away with a concrete next step.

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, listen. Be very, be very active in your listening. Reflect back what you're hearing, their emotions.

Yeah.

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?

Yeah. What are your paths forward? What could you do next?

What could you do next? And then, and then you like I, you know, this is organic. So it's not just like 1, 2, 3, 4, I imagine. But the next, the final step is just, okay, what's the way forward? What do you, what do you want to do?

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.

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.

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

There's kind of like this begs the question, what if they just come to a terrible conclusion and you're just like advice on when to actually just like, what about this instead?

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 in your meetings for open ended questions.

I love this phrase, help me understand. One of my managers used to be really good at this. Just like you could tell, he's like, help me understand this part of your thinking.

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.

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

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 squad, you're going to do great things in the world and sometimes they come up with an idea to performance manage. Someone who's clearly not working in the role but think, oh, maybe I'll wait six months and then we'll have a conversation. I have a strong point of view, I'm not going to let that slide. But I'm going to say help me understand why that is a good idea and I'm going to press on that. And if they don't come to an idea that I'm aligned with, I'm going to share openly my perspective while still empowering them to solve their own problem.

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

Well, I'm going to give you an example of a client. I'm going to call him Jeff, who runs an AI company and he was essentially playing the role of the head of product also. And he had a growing number of engineers and designers and his customer base was growing rapidly and he started to feel completely overwhelmed. So he came to me and we started coaching together. And soon he realized that he was the blocker on every decision, every business decision, every product decision. And he was resenting it. He wanted his team to take more ownership. But with some coaching he realized he was training his team to come to him with every decision because he had always operated that way. So he decided to create squads and have small pods of engineers, product leaders and designers focus on subsets of the team. Very normal as you have a small startup scaling. But he didn't have an engineering manager and a product leader for every one of them. 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 the tech lead on each project so that they would take more ownership. So he 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 and to coaching. I'm going to really ask good questions in our check ins. I'm going to align to the KPIs, ask how things are going, ask where they're stuck. And I just had a session with him last week. It's amazing to see him because he's so much more energized. He said the squads are moving so much faster. The teams feel more empowered and motivated and he has time to pick his head up and plan for 2026 and spend his time and 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.

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. Everyone around you gets better.

Honey, let's try it. So I want you to tell me a, a challenge. It could be a personal challenge, a professional challenge. Just bottom line, something that you're struggling with.

Whoa. The main thing I struggle with these days is just endless work. I feel like this newsletter. I started this newsletter six, seven years ago at this point and originally it was like I'm just going to build this chill newsletter, do this on the side, just kind of chill out for a while and now it's just like, it just grows. I couldn't help but make it more awesome and bigger and have this podcast now and other stuff I got going on. So it's always this. 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. 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 just endless work. I joke that be careful working for yourself if your boss is a workaholic.

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

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.

Yeah.

So I think that's an important element. Absolutely. It's this Indiana Jones boulder constantly chasing me.

Yeah. I can feel the gratitude and the resonance with. 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?

That's one way to put it. Yeah.

I mean, Boulder squishing, Indiana Jones Boulder is coming for you.

Oh, man.

That's a fight or flight instinct we all have.

That's true.

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

What would.

Dream state look like? So let's say in six months, you're still running this beautiful business that you've created and you feel differently. What is happening.

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. The boulders may be smaller.

Yeah. Okay, so what does free time enable for you? When you think about, I hear your deep commitment to quality products.

Yeah.

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

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 got to do this podcast. Got to prep for that. Got to 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 that makes sense. And what's important about exploring and tinkering to you?

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 that makes sense.

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

Active listening.

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

Yeah, yeah. Those are two. Two sides of the coin. 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, because 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, here'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.

Yeah.

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 to have more freedom to go. Go do stuff, which we have a lot of that, but more.

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

Yes. 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.

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

Yeah, yeah.

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

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. 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.

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

Not great?

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

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, that's smart.

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

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.

That's right. Exactly. 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 where. What inputs we have around us. 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?

Something about ready, done, which hasn't kicked in fully yet, but that I'm really excited about as I reduce 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, and I can write about this thing. Oh, every week. Oh, there's nothing 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. 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.

Yeah.

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

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.

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.

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

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

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.

That'd be so nice.

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.

I feel that. I feel that.

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?

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 it in action. Yeah.

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

This is great.

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

Yeah. Yeah, this is great. Okay, so what's the one thing I could do in the next couple of weeks to help you move forward on this? I think one is at least skip a week or two of the newsletter and just actually stick to that plan. So. But it's tough because the next two weeks I got already planned. I got to write. I gotta write a gift guide. That's my. Okay. So the week after I'll take a break. Okay, cool. So two weeks from recording this, I won't publish a newsletter. And then I'm gonna revisit my policies on what I say yes and no to.

I love that. Think about everything you're saying yes to and what are things you want to say yes to that you could treat it with. So really consider that it's a trade off. Every time you say yes to something, the more resonant you are with the end state and what's possible for you, the easier it is to be disciplined in the near term.

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.

Exactly. Yes. Say like a resonant, full bodied yes to the things that are in your mind. 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 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.

I love that. I got great advice in this conversation already. How. What a great roi. For me, at least.

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

It was unusual. I'm just like, wait, I got to get back to asking you questions. That's where I.

We can flip it. We can flip it. I do want to name that. Typically when you're coached versus told what to do, you're more bought in. So if I told you, 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 going to 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.

I, I was Going to 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 that doesn't go well.

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.

Yeah. Okay. That was. That's such an important element, this. That we should have mentioned. And that's. I'm glad you did.

Yeah.

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

Right.

This could segue to something I wanted to spend a little time on, which is burnout. Yeah, 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 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 call. You get Airbnb. He went. He's like a park ranger now. Muir Woods. And that's how far. So peaceful and so wonderful. But I think that's just. People go so hard sometimes and then just get burnt out and never want to do anything like this again. I know that you 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.

Yeah. Well, first of all, I'm glad you brought it up. It's a huge problem. I remember when I was coaching top talent at Stripe, Patrick Collison is really committed to retaining top talent. And I created a program with my team for the top 50 executives in the tech side of the house. And we looked at their engagement scores. We did coaching circles, and it was so sad to see how exhausted that group of incredibly creative and committed leaders was in that moment. And it's so common that people who start with incredible inspiration and incredible capacity start to feel like they've been pushing and pushing and pushing for years. They're parenting, they're leading. Crazy things are happening to the business, and they just can't muster the same kind of motivation they once had. And I see this with my clients all the time. 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, 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 executive at a huge company. But I also interact with founders who started a company with great inspiration, an entrepreneurial vision, and their job has obviously changed every six months. Once you fundraise, once you grow a team, and sometimes especially technical founders will start solving a technical problem they're absolutely obsessed with. They spend three years doing it, the product ships, and then they're stuck managing a board and a team, and they don't even realize they're doing a completely different job than the one that played to their strength. 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 me the most energy, and what are the five things that depleted my energy the most? If you do that for two weeks and you look at patterns, you can tell what are the natural gifts that I'm living in, and what are the things that I'm stuck doing that are exhausting, and they're just slowly. It's like a slow leak in your gas tank that over time shows up in your daily amount of energy.

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.

Yeah.

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, doing these calls and talking to people, because it's like, surface level, you know, here's some things I would do. And it was just so unexciting and energizing. But writing was really energizing, which I never expected. And I love that. And that's what I did. And I just followed that pole.

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

Maybe. Oh, interesting.

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.

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 SAP you have energy.

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. And 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? 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.

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 you do this? Is it like, if you have any ea, they can maybe help you with this? Anything you've seen?

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 going to, 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 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? 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, 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 on. They get to be externally focused. That works well. It's a symbiotic relationship. If you're honest about your strengths and your weaknesses, then you can start to manage around them.

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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 that 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?

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.

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 that means moving up the ladder, but maybe it doesn't for you. I think it does take the courage to move. 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?

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 a gift.

So 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. 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 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? What's working and not working. And within a month, this team was working well together. They were reviewing each other's code base, they were really disagreeing in a healthy way. In our team meetings, they felt more connected to users. And I felt like, okay, this rhythm'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 and he was listening to me ask all these questions about how to sell the vision of what this product would look like in the future. And he said, rachel, your zone of genius or your gift is not being a product strategist. But I've watched you over the last few months and you have gotten the team more motivated than I ever could. And you've influenced the entire executive team behind your ideas and that's impressive. You're a people person. And at first I was offended. What you think I don't have the ability to be a great product leader. And yet I sat with what he said and I knew he was right. Both my parents are therapists. I never wanted to be a therapist. Here I am. I'm basically a work therapist. I love entrepreneurial energy, I love big vision, but I'm a hu. 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 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.

I love that story because I think most people, when they hear this advice and this kind of topic of okay, I, I'm feeling depleted and 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, 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 I 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.

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?

This reminds me, there's a couple 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 Vora 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 off his 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 yeah. And he's the cto, I believe, and has zero reports as no one on ones.

Yeah. And I think that it's a beautiful thing to recognize that, but then to actually address the needs of those reports. Also, I think often people know, ugh, I don't want to have anyone wants. But just not having anyone manage those people is not going to be healthy for your company. So you have to both take your strength seriously and actively manage around your weaknesses.

Is there any maybe last piece of advice on this topic of helping people get to a place where they're feeling much less depleted and just more energized at work?

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 re, you know, refuel your tank. Start with tomorrow. What are the three things you're going to do to like plug up that gas leak and re energize your spark? It might even be you love to read and you're going to start reading 30 minutes before you go to sleep every night. It doesn't have to be a dramatic life change, but recognize that only you know what is resonant and what is depleting and it's your job to take that seriously if you want to show up purposeful and impactful in the world.

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.

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

Yeah, it's just the nightlight is key because at nighttime it's like you need a light book. 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, help 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.

Exactly.

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?

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 couple's therapist, but you don't tell all your friends that you can't stand your partner, but it keeps you up at night. So it's a really tender, important relationship and there aren't enough supports for co founders to navigate it. It's very normal. 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 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 love facts, they seek knowledge, they want depth of awareness and understanding and they also like to be self sufficient. This is a total generalization, but I've seen this pattern over and over again. The CEO is the person who had to sell the vision. They're a person who loves big picture vision strategy they often are great at influencing others. They love to sell ahead of the 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 talk about co founder vows and recommitments and renewals because in a marriage you get married and a lot of times people build a family and then they think, oh, the relationship will just continue 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. Whether that's a dinner every other week, whether that's going out to lunch regularly, whether that's just touching base business wise. But having an in person quarterly check in that space is critical for the health of a co founder relationship.

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

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

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.

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?

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, it's 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 is it, how it's going. So that's all really great. What if you're just ready in it and just like it's really annoying? I don't like this person that much or so much tension constantly. What. What are a couple of things they can do this week, next week?

Co founders typically come to me either in this early phase where they're 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 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. 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 end it or send it was what one co founder said to me. They're coming at this, 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 a360 so they got feedback from their teams and then shared it with one another. But they were able to be open and vulnerable in what was working and what wasn't working. Not immediately, but over time. And they realized they used to love being partners in this work. But as they began to lead different teams, they grew very distant from one another. They were living on opposite sides of the country and actually just coming together and realizing what each other was missing and how lonely it is to lead this scaling company without each other's support and how they actually needed the counterbalance to their strengths and didn't have it was an important start to their healing. And over our coaching, they turned back towards each other and they created more of a rhythm of how they would get together without me involved. And they ended coaching after our arc feeling renewed and really recommitted. They made some changes on their leadership team to fill their gaps. They also started, I think meeting once a week virtually and they started a cadence of getting together in person quarterly. And I don't mean to say that just that time means you're going to heal sometimes coming together and really grappling. I had one last week where we all came together. We had a great full day in person discussion about how they were making this co founder duo, how they were making decisions. And after that conversation, it was really clear that one of the co founders was unhappy and didn't appreciate the other one and was not going to change and realized he was a big part of the problem. And I think is going to leave the business. But that's still success because it's clarity. You're not muddling in the dark, frustrated, unconscious about the interpersonal dynamics you're in. You're making a choice based on your strengths and what the business needs and this relationship dynamic that you're in to either be in it or to lovingly step out of it.

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

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

That's a big statement. The other takeaway here is that just get coaching. It feels like that's the solution if things are just not working great. Like there's only so far you can get just talking.

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

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.

First of all, people, when they want to have a conflict or they want to engage in something that's not working, they come in armored and ready to prove their point. It's natural you've been thinking about this perseverating over whether you should mention it. You finally get to the point of engaging and often there's a misguided view that the goal is to convince the other person that what they're doing is wrong. Actually, the goal of any conflict is to create mutual understanding. So when I go in to have a conversation with let's say my husband, who's not doing his share of the parenting. My goal is to help him understand what I'm struggling with so that he can empathize, see clearly what's happening, and perhaps meet my needs in some way. But it's not for me to prove to him how little he's doing in the house because he might have a totally different story about what's happening. 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. 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. 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. This is me sharing my feelings so the other party can empathize and understand what I'm going through without being defensive. The third step is needs. What are my universal human needs related to this topic? We all have needs. This is not requiring anything of the other person, just helping them understand my needs that are not met. So I have a need for clarity. I have a need for collaboration. I have a need for connection, whatever that is. And lastly, the step is to make a request. Now, in this model, the request is an olive branch to help the other person meet you and see you. It shouldn't be something that's impossible to do. It should be actually something quite small and easy to achieve for the other person to feel successful in connecting to you and understanding you. So in this case, 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. They might make a counter proposal. But the most important thing of this model and this conversation is that the other person understands what I'm going through and they don't feel reactive so that we can have a mutual conversation about what's going on.

Wow. This Point about how when you're trying to. 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.

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

We've got Carol on the podcast.

Great. Yeah. So Carol Robbins created this movement. Right. There's lit. A lot of founders go to her model. That's for founders and tech. 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.

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.

Exactly. It also acknowledges that professionals have feelings. I think that we operate in tech like we're supposed to give all of ourselves, all of our time, all of our energy to this endeavor. And it's purely logical. That's not at all true. It's completely emotional. And if we ignore our feelings, they will bubble up and we will be unconsciously acting from them.

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.

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.

Let me remind folks of the framework. I'm going to try using this. I wish it was a handy acronym, oftener. So the framework is share what you've observed, just the facts of what is happening. Just simply here's. I say you didn't close the fridge fully. Your feelings of how that made you feel, the needs that. Your core human need that drives that feeling, I imagine. And then the request you have of the person.

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. To soliciting empathy.

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.

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.

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

Yeah, exactly.

Awesome. Sort of along 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 help them with is having difficult conversations. And I think we covered actually much of this in what we just talked about. But I'm curious if there's any other advice you have for helping people have difficult conversations. Let me read a quote from one of your clients.

Oh wow. I love.

So she said, uh, Rachel is exceptional at making difficult decisions clear and making it feel possible to get these decisions actualized. Is there anything more there for Cause difficult conversations are difficult. How do we help people make them less difficult? Any tips?

Yeah, well, first of all, difficult conversations makes you want to run away. The marketing on Conflict is poor. I want to reframe that. My belief is when we feel internally ambivalent, we have two inner parts at war, and there's something really beautiful and important to pay attention to. There's something to learn. When we have ambivalence, when we are in conflict, something important is at stake. We care deeply about what we're building, about the person that's letting us down. So the reason it's hard is because there's such an emotional component to it and there's something to learn from it. So first, I want leaders who are listening to think this is hard because I have something to learn here and because it matters. So instead of avoiding it and running away, I'm going to lean into this moment and I'm going to come out of it not just having solved this dynamic and not just having said my piece, but having built a skill. The reason I focus on interpersonal dynamics is because the quality of our relationships determines the quality of our life. I really believe that. And if you cannot have conflict, you can't have healthy relationships. We are going to disagree with the people we love or care about or are building a business with. So first, I just want listeners to reframe ambivalence and interpersonal challenge, 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. 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 world of blame, being a victim, or being a hero. And I see many leaders when they're in a challenging interpersonal conflict, being in victimhood, being in blame, or being in hero. I'm just going to do it for them and forget it. You know, they're so. They're having such a hard time getting this done. I'm just going to do it instead. Take responsibility for your part. What is my piece in making this dynamic happen and how can I address it?

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.

Yes, I love that. Love that question.

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?

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

Awesome. Just remind folks of the NVC framework, because this is the thing that's hard in the moment. Like, oh, where should I be saying, observe feelings? Needs request.

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

People need a little, like, who is it? You said when your client's tattooed, they're his. The vision. Okay, there's. Let's just get some.

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.

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.

Yeah.

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.

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 CEO. 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 asked at Stripe. And when the answer is no to that, no matter how many difficult conversations you have, this is not going to work. So then you have to take action. And even engaging in the hard conversation and seeing what happens can lead you to the clarity that you need to take action on talent. That's not working.

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?

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

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.

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.

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

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 in a business is about building something that users need. It's about product, market fit. And then the wave you're on timing is important. Right. You're going to build a different size business if you're in a sector that's not growing then right now, if you're in the middle of AI, True, you're writing a timing wave and you're solving a core need. But everything besides that is so human. It's about talent and it's about the environment that you put that talent in. So you need to create the conditions such that your talent can thrive.

Such a simple concept that I think people overlook is just everything you do is going to be the people that you have around you and the environment you create for them to operate. I think your point about when you're doing something difficult just to close out this element. I love this idea that if it feels hard, think of it as a learning opportunity. I think anyone listening to this like, oh cool, I'm going to learn something, I'm going to get better. It's such a easier, more motivating way of approaching something that's difficult.

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.

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.

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

We're going to hopefully link to a template of this one page plan.

Yeah, sure.

Happy to share. 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?

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 in what groups? And are you honest or are you just kind of doing it as a quick exercise to move on to what's pressing? So just like I said in co Founder Dynamics, a key is to step out of the dance floor and to get onto the balcony. Executive teams leading a complex business need time away from being in the business to work on the business. 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? Air the things that need to be talked about that no one's talking about because you're too busy. That's the power of combining a simple plan, whether it's one page or not, that aligns you from the top to the bottom, your vision, all the way down to your quarterly goals. And a time where you stop, pause, discuss, reflection, have a little spacious energy. It's not unlike what you said about your own time. You are the executive team. You want a little bit of spacious time to tinker, reflect, create, and come back to the meaningful work you're doing. More energized. And leadership teams need that too.

The way Alpine investors, Graham Weaver, he was on the podcast.

I saw that. I saw that.

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 tweak 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?

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.

One free year of granola. Become an annual subscriber of Lenny's newsletter. Lenny's newsletter.

There you go. So I use granola to take notes in our session so I can be fully present with my clients and I can give them a synthesis of what happened and the next steps they committed to. After our session, 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. 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, 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. So that's their goals for our work together. How they want to grow some of my core frameworks and my beliefs and my training and the granola notes from all of our sessions so that they can access between just some extra spot support. They're going into this conversation, how should they approach it? They're anxious about this team meeting. How can they make the most of it? More tactical support. I see personal coaching as still critical for what is your vision of your life? How do you want to shift your core behavior to align with that vision? But that AI can play a real helpful role in between on the tactics.

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

It's something I'm building right now, so my clients don't have that yet.

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.

I don't want to build that.

It's not your zone of genius.

Exactly.

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

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 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.

What a beautiful way to end it. With that, we've reached our very exciting lightning round. I've got five questions for you. Are you ready?

I am ready.

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

One of them I said before the 15 commitments of conscious Leaders. And I love Designing youg Life by Bill Burnett.

Mm. I love that book, too. People don't talk about that book enough. Next question. Favorite recent movie or TV show you really enjoyed?

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.

I have not seen that. I hear everyone talking about it. I'm going to 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.

I really love Loom. 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.

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

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

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

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.

Have you seen the Wes Anderson stories of his stories?

Some of them, yeah. They're great.

Yeah, they're so amazing. Oh, my God. And it's like we're all dolls. I think it's personify him like he's like a character in the story.

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

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. I think we're going to help a lot of people improve their lives and their careers. Thank you so much for being here.

Absolutely. Thanks for having me.

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 and how can listeners be useful to you?

Yeah, find me@lockettcoaching.com and how can listeners be useful? Listeners should turn towards each other, build great relationships, and send CEOs and co founders my way if they need coaching.

Thank you so much for being here.

Thanks for having me. Take care, Lenny.

Bye everyone. 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@lennyspodcast.com See you in the next episode.