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

Summary

In this episode, executive coach Rachel Lockett joins Lenny to unpack the human side of building products and companies. She argues that the quality of our relationships determines the quality of our work and life, and provides actionable tools to improve both.

Lockett identifies the biggest gap for leaders, especially in tech, as knowing when to coach versus when to advise. Many leaders climb the ladder by being the smartest person in the room, but this approach fails at scale. She introduces two core coaching skills: active listening (with three levels, culminating in “global listening” that hears emotions and body language) and asking powerful questions using the GROW model (Goal, Reality, Options, Way forward). A live coaching demo with Lenny on his struggle with “endless work” illustrates the framework in action.

The conversation shifts to preventing burnout by designing your life around your “gifts”—the activities that give you energy. Lockett recommends tracking what energizes and depletes you for two weeks, aiming to spend 80% of your time in your strengths. She shares her own story of transitioning from product management to coaching after a colleague pointed out her true gift was with people, not product strategy.

Finally, Lockett provides frameworks for healthier relationships, whether with co-founders or team members. She emphasizes the importance of “co-founder vows” and regular check-ins, and introduces Marshall Rosenberg’s Nonviolent Communication (NVC) for conflict: Observations, Feelings, Needs, and Requests. She reframes difficult conversations as growth opportunities, stating, “the cave you fear contains the treasure you seek.”

Recommendations

Books

Nonviolent Communication — A book by Marshall Rosenberg that provides the four-step framework (Observations, Feelings, Needs, Requests) for having difficult conversations and resolving conflict with the goal of mutual understanding.
The Fifteen Commitments of Conscious Leadership — A book recommended by Rachel that discusses concepts like taking 100% responsibility and moving out of the dynamics of blame, victimhood, and heroism.
Designing Your Life — A book by Bill Burnett that Rachel loves and recommends for its practical approach to life and career design.

Frameworks

GROW Model — A coaching framework for asking powerful questions, standing for Goal, Reality, Options, and Way forward. Used to help people unlock their own insights and solutions.
Nonviolent Communication (NVC) — Marshall Rosenberg’s four-step framework for conflict and difficult conversations: Observations, Feelings, Needs, and Requests. The goal is mutual understanding, not proving a point.

People

Joseph Campbell — Rachel shares her favorite life motto, a quote from Joseph Campbell: ‘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.‘

Tools

Grain — An AI tool Rachel uses to take notes during coaching sessions, allowing her to stay fully present with clients and provide them with a synthesis and next steps afterwards.

Topic Timeline

00:05:00 — Introduction and Rachel’s Hopes for the Conversation — Rachel Lockett is introduced as an executive coach and former HR leader at Pinterest and Stripe. She shares her hope that listeners will see the human side of business building as fun, impactful, and achievable with simple tools. She wants product and engineering leaders to feel empowered to attune to the people around them.
00:09:02 — The Biggest Leadership Gap: Coaching vs. Advising — Rachel identifies the core struggle for technical leaders: knowing when to coach versus when to advise. Leaders often assume they must have all the answers, but this trains teams to bring them every hard problem. Coaching, by contrast, involves curiosity and helping people solve their own problems, which unlocks team brilliance and motivation. Advising is appropriate for urgent issues or skill gaps.
00:13:25 — Core Coaching Skill 1: Active Listening (Three Levels) — Rachel teaches the first core coaching skill: active listening. She describes three levels: Level 1 (internal, distracted by your own thoughts), Level 2 (focused on the other person’s words), and Level 3 (global listening that hears emotions, tone, and body language). She demonstrates Level 3 listening by coaching Lenny on what it’s like to be a dad, mirroring back both his joy and the challenges he described.
00:18:44 — Core Coaching Skill 2: Powerful Questions (GROW Model) — The second core skill is asking powerful questions using the GROW model: Goal (what does success look like?), Reality (where are you stuck?), Options (what paths could you take?), and Way forward (what will you do next?). These questions help people gain insight and arrive at their own solutions. Rachel emphasizes that coaching is a tool to use when you believe the person has the context to solve their own problem.
00:27:47 — Live Coaching Demo: Lenny’s Struggle with Endless Work — Rachel conducts a live coaching session with Lenny on his challenge of feeling constantly chased by an “Indiana Jones boulder” of work from his growing newsletter and podcast. Using the GROW framework, they explore his goal (25% more free time while maintaining quality), reality (a pattern of saying yes to new projects), options (saying no more, delegating, skipping a newsletter week), and way forward (Lenny commits to skipping a newsletter in two weeks and revisiting his ‘yes/no’ policies).
00:42:47 — Avoiding Burnout by Designing a Life in Your Gifts — Rachel discusses burnout prevention by focusing on your “gifts”—the activities that give you energy. She recommends tracking what energizes and depletes you for two weeks to identify patterns. The goal is to spend 80% of your time in your strengths. She shares her personal story of leaving product management after a colleague pointed out her true gift was as a “people person,” leading her to coaching.
01:00:05 — Building Healthy Co-founder and Team Relationships — The discussion turns to building healthy relationships, starting with co-founders. Rachel highlights that 65% of startups fail due to co-founder conflict. Key strategies include building self-awareness (using tools like the Enneagram), making conscious commitments (“co-founder vows”), and creating regular check-in rhythms to step onto the “balcony” and assess the relationship and business.
01:12:50 — Framework for Difficult Conversations: Nonviolent Communication (NVC) — Rachel introduces Marshall Rosenberg’s Nonviolent Communication (NVC) framework for having difficult conversations. The four steps are: 1) Observations (state facts without judgment), 2) Feelings (express your emotions), 3) Needs (identify universal human needs), and 4) Requests (make a small, doable ask). The goal shifts from convincing the other person they are wrong to creating mutual understanding.
01:32:17 — Creating Clarity and Alignment with a One-Page Operating Plan — Rachel advocates for simplifying company alignment with a one-page operating plan, inspired by Alpine Investors. This plan links Vision/Values, Strategic Intentions/KPIs, Annual Goals, and Quarterly Goals in one view. Coupled with a regular operating rhythm (e.g., quarterly offsites), it creates clarity, connection, and space for leadership teams to work “on the business” instead of just “in the business.”
01:40:00 — How AI is Impacting Coaching and a Final Call to Action — Rachel shares how she uses AI tools like Grain for session notes and ChatGPT for creative brainstorming. She is also experimenting with building an AI coach for clients to access between sessions, trained on their development plans and past conversations. She concludes with a call to action: in an increasingly lonely world, leaders must actively create environments of connection to have more fun and build better businesses.

Episode Info

Podcast: Lenny’s Podcast: Product | Career | Growth
Author: Lenny Rachitsky
Category: Technology Business Entrepreneurship
Published: 2025-11-23T12:03:19Z
Duration: 01:45:19

References

URL PocketCasts: https://pocketcasts.com/podcast/aff3edd0-c8a4-013a-d954-0acc26574db2/episode/fa935c69-a427-4b8d-9e67-08fe7c11d140/
Episode UUID: fa935c69-a427-4b8d-9e67-08fe7c11d140

Podcast Info

Name: Lenny’s Podcast: Product | Career | Growth
Type: episodic
Site: https://www.lennysnewsletter.com/podcast
UUID: aff3edd0-c8a4-013a-d954-0acc26574db2

Transcript

[00:00:00] When clients come to you, what is the biggest gap they have that is keeping them from being

[00:00:04] successful as leaders? Most leaders, especially technical leaders, assume they have to have all

[00:00:09] the answers. People have climbed the ladder because they’ve been dependable, reliable,

[00:00:15] the smartest person in the room. But great leaders know that when you try to advise and have the

[00:00:20] answer all the time, you’re not actually equipping your team to go solve the hard problems. You’re

[00:00:24] training your team to come to you with all the hard problems. Difficult conversations are

[00:00:28] difficult. How do we help people make them less difficult? We operate in tech, like we’re supposed

[00:00:34] to give all of ourselves, all of our time, all of our energy to this endeavor. And it’s purely

[00:00:39] logical. That’s not at all true. It’s completely emotional. Professionals have feelings. People,

[00:00:45] when they want to have a conflict, they come in ready to prove their point. There’s a misguided

[00:00:49] view that the goal is to convince the other person that what they’re doing is wrong.

[00:00:53] Actually, the goal of any conflict is to create mutual understanding. Talk about what you’ve

[00:00:58] learned.

[00:00:58] about helping leaders in tech avoid burnout.

[00:01:01] When people are in their gifts and their strengths, they have more energy. We all have

[00:01:05] more energy when we’re operating from the things we naturally are good at. It’s no one else’s job

[00:01:10] to help you live in your gifts. What I notice in big companies is people are often annoyed or

[00:01:15] frustrated with their management for not making their job more interesting. No, your manager’s

[00:01:19] job is to help you perform in the job you were hired to do. It’s your job to navigate your

[00:01:25] career. The power of this is this makes your life so much better. Honey, let’s try it. So

[00:01:29] I want you to tell me…

[00:01:31] A challenge. Something that you’re struggling with.

[00:01:33] The main thing I struggle with these days is just…

[00:01:36] Today, my guest is Rachel Lockett, an executive coach and former long-time HR leader at Pinterest

[00:01:43] and at Stripe. She works with CEOs and founders and leaders at tech companies on both ways that

[00:01:48] they are, emotional and positive intelligence, resilience, and courage, and what they do,

[00:01:54] setting vision and strategy, prioritizing, and building trusted and accountable teams.

[00:01:58] She’s someone I’ve heard a lot about over the years from

[00:02:00] other podcast guests, and this conversation is powerful. It’s jam-packed with advice and tips

[00:02:06] and frameworks that’ll make you a better leader and also a better person. We even do a couple

[00:02:11] live coaching sessions to demonstrate some of Rachel’s approaches, and as you’ll see,

[00:02:16] I had a number of epiphanies during this conversation. If you enjoy this podcast,

[00:02:20] don’t forget to subscribe and follow it in your favorite podcasting app or YouTube.

[00:02:24] It helps tremendously. And if you become an annual subscriber of my newsletter,

[00:02:28] you get a year free of a ton of…

[00:02:30] 1.3%. It’s a small number, but in the right context, it’s a powerful one.

[00:02:54] Stripe processed just over $1.4 trillion last year. That figure works out to be about

[00:03:00] $1.4 trillion.

[00:03:00] That figure works out to be about $1.4 t r i ll i o n . T ha t f i gu re w or k so u tt o b e ab o u t$ 1.4 trillion.

[00:03:00] 1.3% of global GDP. It’s a lot, but it’s also just 1.3%.

[00:03:07] Stripe handles the massive scale and complexity of many of the world’s fastest-growing enterprises,

[00:03:13] including 78% of the Forbes AI50 and more than half of the Fortune 100.

[00:03:19] There’s a reason I’ve had more leaders from Stripe on this podcast than any other company.

[00:03:23] They know how to build great products that scale and that people love.

[00:03:27] Stripe is also a lot more than just payments.

[00:03:30] They’ve also been able to build great products that scale and that people love.

[00:03:30] They’ve also got a category-leading billing solution and a highly-optimized checkout experience

[00:03:35] built specifically to increase your checkout conversion. Enterprises like Atlassian,

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[00:03:44] with access to more than 125 global payment methods. Join the ranks of industry leaders

[00:03:49] like Salesforce, OpenAI, and Pepsi that are using Stripe to grow faster and grow GDP.

[00:03:56] Learn how Stripe can help your business grow at stripe.com.

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[00:04:53] Slash Lenny.

[00:04:59] Rachel, thank you so much.

[00:05:00] Thank you so much for being here and welcome to the podcast.

[00:05:03] Thank you so much for having me, Lenny. I am honored to be here.

[00:05:06] I’m honored to have you here. I was going to start with a different question,

[00:05:10] but we were chatting ahead of this conversation and I always like to ask guests,

[00:05:13] what do you want people to get out of this conversation? And I loved your answer. So

[00:05:17] I just want you to share this. Let me just ask you, what are you hoping people get out

[00:05:21] of the conversation we’re about to have?

[00:05:23] Genuinely, I hope that your listeners take away that the human side of business building

[00:05:29] is incredibly fun.

[00:05:30] And impactful. And that it’s easy to do. They can do it with simple tools. So I’m hopeful that

[00:05:37] through this conversation, heads of product, heads of engineering, founders, walk away feeling more

[00:05:43] empowered and more motivated to attune to the people around them.

[00:05:47] So what I’m hearing is just if you’re struggling with

[00:05:49] the human side of building a product, building a team, building a company,

[00:05:53] there are answers. You can do it.

[00:05:55] Yes, exactly. It is achievable and it’s actually most natural.

[00:05:59] Leaders want to care about the people they work with. They want to empower those around them. But

[00:06:05] sometimes the busyness of our world gets in the way and the urgency of the litany of things to do

[00:06:12] distracts you from the people in front of you. And actually, if you really understand the talent

[00:06:17] around you and you create an environment where they can be successful, your business will thrive.

[00:06:22] I think the hardest part of this for people is just there’s like the knowing this can be

[00:06:26] helped with. The other is just being vulnerable enough to seek help.

[00:06:29] And to take this on because it’s so hard. Just like, oh, maybe I’m not a great manager.

[00:06:35] That’s I don’t that doesn’t feel good.

[00:06:37] Yeah, that’s true. I mean, it’s vulnerable to seek help. But I think your audience,

[00:06:42] I know, to be incredibly committed to growth. I hear people who come on your podcast and they’ve

[00:06:49] spent decades focused on self-improvement. And I actually want to tell you a story about one of my

[00:06:55] clients who loves your podcast. And I was talking to him last week.

[00:07:00] He’s a client I’ve seen for 10 years. And he’s a person who exemplifies a commitment to personal

[00:07:06] growth. I started working with him when he was a frontline engineering manager at Coinbase.

[00:07:14] And we talked about who he is, what his strengths are, and his bigger picture why.

[00:07:20] And he talked about this dream of creating a global movement one day.

[00:07:26] He was really focused on building community.

[00:07:29] And he thought the path for creating possibility in the world around him was

[00:07:36] creating a strong community around him. And he continually worked on his leadership capacity.

[00:07:43] And over the 10 years, at some point, he created a tattoo on his arm. That’s a sun

[00:07:49] with a redwood grove around it that reminded him of his core strengths and his purpose.

[00:07:56] And today, guess what he’s doing, Lenny?

[00:07:58] You’re killing it.

[00:08:00] He’s not only killing it, but he’s running a community, a global community for Coinbase

[00:08:06] called Base and the Base app. It’s the largest Ethereum L2 in the world. And it’s a community

[00:08:12] of creators and developers. And he’s having a great time. He’s having more fun than ever.

[00:08:20] And so I think for the people who are committed to excellence and impact,

[00:08:25] recognizing that if they lean into their gifts,

[00:08:27] and they get back into their purpose, they can have more fun while having an impact on the world.

[00:08:33] This story reminds me just why I love these sorts of conversations,

[00:08:36] because the sort of stuff we’re going to be talking about, and we’ll get into it right

[00:08:38] after this final preamble, is stuff that’s usually locked away in these very small rooms,

[00:08:44] are only accessible to folks with a bunch of money. This is stuff people pay tens of thousands

[00:08:49] of dollars, hundreds of thousands of dollars for over the course of their career. And I just love

[00:08:52] the idea of sharing all this with everyone to help them all learn from the stuff that you’ve

[00:08:56] learned from all these people you’ve worked with. And I think that’s a really good way to do that.

[00:08:57] And I think that’s a really good way to do that. And I think that’s a really good way to do that.

[00:08:57] So I’m really excited to be digging into stuff. The first thing I want to dive into,

[00:09:02] I actually asked you, when clients come to you, what is the thing, what is the biggest gap they

[00:09:07] have that is keeping them from being successful as leaders? And you told me it’s essentially

[00:09:12] knowing when to coach versus knowing when to just tell people what to do and learning to coach.

[00:09:19] Talk about what you see there, why this is so important, and how you help people develop the

[00:09:23] skill. I think that most leaders, especially technical leaders,

[00:09:27] assume they have to have all the answers. People have climbed the ladder in whatever realm

[00:09:34] they’re in because they’ve been dependable, reliable, the smartest person in the room.

[00:09:40] But when you’re leading a quickly scaling company, you quickly have less context than

[00:09:47] the people you’re around. And the way you were operating before doesn’t work because you don’t

[00:09:51] have the ability to wrap your arms around every problem in a deep way.

[00:09:55] So I’ve seen leaders at every phase, from frontline managers up to running an 8,000-person

[00:10:02] company, struggle with knowing when do I have to have the answer? And when I don’t have the answer,

[00:10:10] what options do I have? But great leaders know that when you try to advise and have the answer

[00:10:16] all the time, you’re not actually equipping your team to go solve the hard problems.

[00:10:20] You’re training your team to come to you with all of the hard problems.

[00:10:24] And you’re not actually equipping your team to go solve the hard problems.

[00:10:25] And coaching is a different way. It’s an alternative path that unlocks brilliance

[00:10:31] in your team and is way more motivating for the people around you. So coaching is actually

[00:10:38] a learnable skill, obviously, because there’s tons of coaches around Silicon Valley.

[00:10:43] But you don’t have to coach in the same way that an executive coaches. You can shift your energy

[00:10:49] into curiosity when someone brings you a hard problem to solve and create space to

[00:10:55] get curious and help them solve their own problem. So obviously, sometimes advising is the right

[00:11:01] path. If there’s an urgent issue, the person coming to you doesn’t have the skill they need,

[00:11:07] that’s a time to advise and help. But leaders over-rotate, assuming the people that they’ve

[00:11:14] hired, who are experts in their domain, need them to solve the problem. So I think it’s useful for

[00:11:21] your listeners to actually know that coaching is an opportunity to help them solve their own problem.

[00:11:25] alternative. And I can help them learn some basic skills around this.

[00:11:31] Okay, I’d love to learn those skills. What this makes me think about is there’s this famous

[00:11:35] Harvard Business Review piece, I don’t know, it’s like 30 years ago, maybe about the monkey

[00:11:39] on the back, you know, this piece. Okay, so, okay, we’ll link to it. It’s this idea that

[00:11:45] as a leader, people always just coming to you trying to give you their monkey that’s sitting

[00:11:49] on their back. And they’re like, hey, this monkey’s causing me all this problem. I don’t

[00:11:52] know what to do about this monkey. Here you go, you take it and feed it.

[00:11:55] And help it figure out what it needs. And the role of a leader is to keep the monkey on the

[00:11:59] back of the person and help them figure out how to solve the problem. Exactly what you’re

[00:12:03] describing. Yeah, that’s a great analogy. I love that. I think leaders make things up when

[00:12:08] they don’t have answers. Sometimes a person comes to you with a problem, and you just want to help.

[00:12:16] But the best way to help is actually doing something that most leaders don’t do well.

[00:12:20] It’s attuning to what is the context? What does this person need?

[00:12:25] What are they blocked on? And ask them those questions so that they can solve their own

[00:12:30] problem. So we’re gonna let’s talk about how to get better at this. But first of all, when you said,

[00:12:34] when is it actually smart to just tell them what to do? You said it’s when they don’t have the

[00:12:38] skills to do it. Is there any other kind of heuristics of like, okay, just tell them what

[00:12:41] to do in these cases? Yeah, it’s an urgent issue. And you actually have an answer that you want to

[00:12:48] drive. So don’t coach and make it a game. Like you want your person on your team,

[00:12:55] to guess what’s in your mind. That’s not a good time to coach. You have something you absolutely

[00:13:00] want them to do. You know, the right answer. You want them to be motivated to go do it.

[00:13:06] Advise them, help them see the path. But most leaders over index on that solution.

[00:13:13] So I want to share maybe Lenny, I can teach you two skills that I think are the basics

[00:13:19] of leader coaching that you can use in your own life tonight with your wife.

[00:13:24] Okay.

[00:13:25] operate with and hopefully your listeners can use them too let’s do it okay so the first skill

[00:13:33] is active listening and lenny you’re probably a good listener because this is what you do for a

[00:13:38] living as you listen to the people who come on your podcast but i don’t know if you’ve seen fight

[00:13:43] club there’s a quote most people aren’t listening they’re just waiting for their turn to talk this

[00:13:50] is rampant in tech and great leaders flip that script and tune in they’re the kinds of leaders

[00:13:56] who walk into a room and they can see the elephants they can name them they can ask the

[00:14:02] hard questions to get people collaborating so there’s actually three levels to listening

[00:14:08] so the first level listening level one is internal let’s say you’re talking to me about a problem

[00:14:14] i’m thinking about the implications of that problem on me i’m completely distracted with

[00:14:19] my own listening and i’m thinking about the implications of that problem on me

[00:14:20] my own inner dialogue that’s level one most people go through their worlds rushed and in level one

[00:14:27] level two listening is focused so you’re talking to me and i can repeat back what you’re saying

[00:14:34] so i am listening to the words you’re describing and that’s typically what happens in a good one-on-one

[00:14:41] we’re problem solving together i’m focused on your words level three listening listening is global

[00:14:48] listening so i’m talking to you and i’m thinking about the implications of that problem on me

[00:14:49] so that’s when i’m hearing beneath the words and hearing what you’re communicating not just what

[00:14:55] you’re saying i see your body language i notice your tone of voice i know the context around what

[00:15:00] you’re talking about and i can reflect back more insight about what’s happening than you’re aware

[00:15:06] of because i’m understanding everything you’re communicating so dropping into level three

[00:15:11] listening is what great leaders do when they’re influencing when they’re selling when they’re

[00:15:16] pitching a vision and definitely when they’re coaching

[00:15:19] so do you want to try it let’s do it okay how about this i’ll demonstrate some level three

[00:15:28] listening i’m gonna ask you a question okay uh-oh you told me earlier you’re a father

[00:15:33] yeah what is it like to be a dad wow what is like to be a dad uh it’s uh amazing it’s like

[00:15:42] the most amazing thing i’ve ever done uh in many ways i love it so much it’s also

[00:15:49] quite challenging at times dealing with setting boundaries and knowing when to just let him do

[00:15:55] the thing he’s really excited about or just saying now and just letting him cry for a while that’s

[00:16:00] something i’ve been dealing with recently but it’s it’s like everything people tell you it is

[00:16:04] and so and basically in every way except uh the joy is so much higher so much higher than you

[00:16:10] hear from other people because people always talk about all the all the downsides all the pain and

[00:16:13] challenges yeah and i see you when you talk about being a father

[00:16:19] initially i saw you really squirm in your chair well this is a big question and you know you

[00:16:25] looked up and down and kind of avoided my eye contact at first because my sense is you love

[00:16:31] being a dad and it’s so challenging it’s so tiring and i’m hearing both of that in your

[00:16:38] answer like the high joy and the discomfort in having to sleep train and having to disappoint

[00:16:46] and navigating challenging behavior

[00:16:49] nailed it that was very nice to hear uh clearly you listened to everything i said and that was a

[00:16:56] really good example of active listening what what does it feel like to be seen that way

[00:17:01] it feels really nice it feels really nice to be to be heard and and it’s not just like you’re

[00:17:06] repeating back my words it’s here’s what i got out of like kind of the level below what you’re

[00:17:11] saying and the gist and the bigger picture yeah there’s some emotional connection when you listen

[00:17:16] actively and that took you know less than a minute to get to the point where you’re like

[00:17:19] okay i’m going to do this for a minute so what i want to invite listeners to understand is that

[00:17:23] active listening doesn’t mean you’re setting up an hour coaching session with every person on your

[00:17:27] team no one has time for that but even in the time you’re already spending just focusing on the

[00:17:34] other person in a way that is novel and really gives them their your full attention so you can

[00:17:39] see their feelings under what they’re saying goes a long way to motivating your team and helping them

[00:17:45] understand what’s actually happening under the surface in this situation

[00:17:49] i think there’s just so much power in just in different words repeating back what they said

[00:17:54] that’s almost implied in what you’re describing like it sounds like so i don’t know like a trick

[00:17:59] they’ll see through but knowing that you’re listening to me and you’re gonna show me i

[00:18:04] keep listening it still feels really nice to just hear back what i said there’s a lot of power in

[00:18:08] that and it’s subtle oh great yeah there’s there’s an element of synthesizing what i’m hearing

[00:18:13] verbally that’s the focus listening part and then mirroring back the emotions that i’m noticing

[00:18:18] the emotions even things that i’m hearing and i’m hearing the emotions that i’m hearing and i’m

[00:18:19] guessing and i can say is that right and you can say no actually i’m not conflicted about the

[00:18:26] challenges of being a dad i just am so joyful and then now i understand where you’re coming

[00:18:31] from and so do you awesome okay so this is a core skill of coaching is active listening yes

[00:18:37] so that’s listening second skill powerful questions so asking powerful questions

[00:18:44] means i’m curious about what’s really going on and there’s not one right answer

[00:18:49] so a powerful question helps you gain insight and it takes you to a new solution set you didn’t

[00:18:56] have before but it’s not me leading the witness i’m not trying to guide you to a specific answer

[00:19:03] that wouldn’t be a powerful question so something that i like to equip leaders with

[00:19:11] is four kinds of questions that you can ask to unlock insight so the first kind is

[00:19:19] i use a grow model so the grow model just is four different categories of kinds of powerful

[00:19:24] questions so the g in grow is goal so what does success look like what’s the outcome that you

[00:19:31] want to have any question that’s around defining the best case scenario the r in the grow model is

[00:19:38] about your current reality where are you stuck what are your current challenges what have you

[00:19:43] tried the o is about your options so let’s expand the

[00:19:49] opportunities that you can understand of the choices you have in front of you

[00:19:53] what are the various paths you could take and the w in the grow model is the way forward what

[00:20:00] are you going to do next so this sounds simple and it is simple if you take the time and space

[00:20:07] to listen carefully and ask any of these questions the people on your team will appreciate the space

[00:20:13] and time to unlock an option that they didn’t think of before and walk away with a

[00:20:19] concrete next step okay so just to reflect back what you’re saying so this is someone comes to

[00:20:25] you with a monkey on their back here’s a problem i’m trying to solve uh this problem this person

[00:20:29] on my team is having is just like not doing something right or this feature isn’t working

[00:20:35] something like that you’re so first of all it’s listen be very uh be very active in your

[00:20:40] listening reflect back what you’re hearing their emotions yeah and then ask them questions around

[00:20:46] what does success look like for this what is the goal what is the goal what is the goal what is the

[00:20:49] goal what does success look like for the thing you’re trying to hear what does success look like

[00:20:52] two is just what’s today’s reality what’s happening today then options here’s options that you think

[00:20:58] exist so this is you asking them what are the options yeah what are your paths forward what

[00:21:02] could you do next what could you do next and then and then you like i you know this is organic so

[00:21:08] it’s not just like one two three four i imagine yeah the next the final step is just okay what’s

[00:21:12] the way forward what do you what do you want to do that’s exactly right and you don’t have to do

[00:21:15] it in this order these are just four kinds of questions so you might come and

[00:21:19] someone’s super clear about their outcome you know that you don’t need to spend any time asking

[00:21:24] them questions about that maybe you just want to really dig in on where are they stuck and once

[00:21:28] they start talking about their reality and where they’re stuck then they realize oh i’m stuck

[00:21:34] because my cross-functional partner is blocking me and i don’t have any relationship with them i

[00:21:38] need to go meet with them actually and just have a breakthrough conversation tell them where i’m

[00:21:42] stuck so sometimes talking this out loud just creating that space for them is going to help

[00:21:47] them tremendously and there’s kind of an implication

[00:21:49] here that the person often knows the answer or can come to the answer and they just need a little bit

[00:21:54] of nudge to get there yeah this is definitely you want to coach when you think the person you’re

[00:22:00] talking to has the right context and can solve their own problem that’s a premise of coaching

[00:22:06] you wouldn’t coach if someone needs your guidance and comes to you and says hey i’m trying to take

[00:22:12] my company public you took your company public can you tell me exactly the steps you took to get

[00:22:16] there not a good time to coach there’s

[00:22:19] like this begs the question what if they just come to a terrible conclusion and you’re just like

[00:22:24] advice on when to actually just like what about this instead yeah okay i think that’s great so

[00:22:32] if you have a really strong negative uh reaction to what they’re sharing of course it’s not it

[00:22:38] doesn’t behoove anyone to hide that i think you get curious hey help me understand how you came

[00:22:43] to that conclusion because here’s my reaction to that so you’re honest but you’re also curious about

[00:22:49] this so coaching in a manager or leader context is not the same as in an executive coaching

[00:22:55] conversation you’re managing this person you’re responsible for their outcomes you’re not setting

[00:23:00] up an hour-long coaching session you’re just using coaching as an additional tool in your

[00:23:05] toolkit from advising and you’re creating more space maybe 15 more space in your one-on-ones

[00:23:11] in your meetings for open-ended questions i love this phrase help me understand one of my managers

[00:23:15] used to be really good at this just like you could tell he’s like help me understand

[00:23:19] this part of your your thinking yeah and the other thing that does when you’re curious and

[00:23:24] you don’t just shut down someone’s idea is you’re helping them think you’re not helping them realize

[00:23:31] they’re going to screw it up unless they come to you for advice you’re helping equip them with

[00:23:36] the right questions to ask and the right skepticism to have and so it’s always useful

[00:23:43] to be in conversation when someone who reports to you has a different worldview than you do

[00:23:49] there’s some reason they came up with this great idea that you think is a terrible idea and

[00:23:53] actually that’s where the learning happens and you may actually be wrong and you may realize okay

[00:23:58] they actually have the better solution i get it now yeah this actually happens to me all the time

[00:24:03] in talent conversations because i have a background in being an hr business partner and i’m working

[00:24:07] with ceos and they’re thinking about building their leadership team and i want everyone to have

[00:24:12] a very rigorous stance on their talent because if you have an a-plus squad you’re going to do great

[00:24:18] things in the world and i’m going to do a lot of things in the world and i’m going to do a lot of

[00:24:19] and sometimes they come up with an idea to performance manage someone who’s clearly not

[00:24:25] working in the role but think oh maybe i’ll wait six months and then we’ll have a conversation

[00:24:29] i have a strong point of view i’m not going to let that slide but i’m going to say help me

[00:24:35] understand why that is a good idea and i’m going to press on that and if they don’t come to an idea

[00:24:42] that i’m aligned with i’m going to share openly my perspective while still empowering them to

[00:24:47] solve their own problem

[00:24:48] to close

[00:24:49] the loop on this piece of advice is there an example you could share to make this super

[00:24:53] concrete for folks well i’m going to give you an example of a client i’m going to call him jeff

[00:24:58] who runs an ai company and he was essentially playing the role of the head of product also

[00:25:05] and he had a growing number of engineers and designers and his customer base was growing

[00:25:12] rapidly and he started to feel completely overwhelmed so he came to me and we started

[00:25:18] coaching together

[00:25:19] and soon he realized that he was the blocker on every decision every business decision every

[00:25:26] product decision and he was resenting it he wanted his team to take more ownership

[00:25:31] but with some coaching he realized he was training his team to come to him with every decision

[00:25:37] because he had always operated that way so he decided to create squads and have small pods of

[00:25:47] engineers product leaders and designers

[00:25:49] focus on subsets of the team, very normal as you have a small startup scaling.

[00:25:56] But he didn’t have an engineering manager and a product leader for every one of them.

[00:26:00] So this was a little bit earlier than he was equipped for because he did it out of necessity.

[00:26:06] And he also realized he needed to create some behavior change for the way he was interacting

[00:26:11] with the tech lead on each project so that they would take more ownership.

[00:26:17] So he really invested in this idea of, I’m going to start to set the system up.

[00:26:25] So we have a product review every two weeks.

[00:26:27] They each have clear KPIs they’re driving to that we co-design.

[00:26:31] And for this next quarter, I’m shifting from the role of deciding on everything to coaching.

[00:26:37] I’m going to really ask good questions in our check-ins.

[00:26:41] I’m going to align to the KPIs, ask how things are going, ask where they’re stuck.

[00:26:46] And I’m going to really ask good questions in our check-ins.

[00:26:47] And I’m going to really ask good questions in our check-ins.

[00:26:47] I just had a session with him last week.

[00:26:50] It’s amazing to see him because he’s so much more energized.

[00:26:54] He said the squads are moving so much faster.

[00:26:57] The teams feel more empowered and motivated.

[00:27:00] And he has time to pick his head up and plan for 2026 and spend his time in his gifts,

[00:27:06] which are product vision and strategy.

[00:27:08] So that’s more of a global example of what results from leaders shifting from the mode

[00:27:17] of solving issues to the mode of solving issues.

[00:27:17] So that’s more of a global example of what results from leaders shifting from the mode of solving issues to the mode of solving issues.

[00:27:47] So that’s more of a global example of what results from leaders shifting from the mode of solving issues to the mode of solving issues.

[00:27:47] that you’re struggling with whoa the main thing i struggle with these days is just uh endless work

[00:27:57] i feel like this newsletter i started this newsletter six seven years ago at this point

[00:28:01] and originally it was like i’m just gonna build this chill newsletter do this on the side just

[00:28:06] kind of chill out for a while and now it’s just like it just grows i couldn’t help but make it

[00:28:12] more awesome and and bigger and have this podcast now and other stuff i got going on so it’s always

[00:28:17] this so i’m in a world now where it’s just this the way i think about it is the indiana jones

[00:28:22] boulder is constantly in my back rearview mirror just coming at me because i need to get a newsletter

[00:28:29] post out get podcast episodes out do all the things associated with that i’m also just in the

[00:28:33] middle of like i have this large slack community at twitter and linkedin so i’m just constantly

[00:28:37] being barraged with like small little asks and things and all these little things that never

[00:28:41] it’s hard to just ignore and say no to so so what i struggle with just uh endless work i joke that

[00:28:47] be careful working for yourself if your boss is a workaholic

[00:28:50] i totally relate to that okay so i’m hearing um noise barrage of of needs and just constant

[00:29:00] requests of you online in your work life there’s always something that you need to be doing

[00:29:07] and you designed it that way yourself so you’re kind of aware of i had this one intention of

[00:29:14] a path to freedom inside of you and i’m like i’m gonna do this i’m gonna do this i’m gonna do this

[00:29:17] i imagine the newsletter is like a fun passion project and you couldn’t help but make it this

[00:29:24] all-consuming full-time job that’s right let me just add it’s like in so many ways the most

[00:29:30] awesome thing i could ever imagine doing also and extremely fulfilling and i couldn’t think of

[00:29:33] anything better i’d rather be doing yeah so i think that’s an important element but still it’s

[00:29:38] indiana jones boulder constantly chasing me yeah i can feel the gratitude and the resonance with

[00:29:46] what you get to do every day

[00:29:47] and yet i hear you questioning why does it have to feel like i’m fighting for my life

[00:29:53] while i’m doing this thing i love that’s one way to put it yeah i mean boulder squishing yeah john

[00:30:00] boulder is coming for you oh man that’s a fight or flight instinct that’s true that’s true okay so

[00:30:06] thank you for being vulnerable enough to share that with your listeners

[00:30:10] and with me i want to ask you

[00:30:14] what would

[00:30:17] dream state look like so let’s say in six months you’re still running this beautiful business that

[00:30:26] you’ve created and you feel differently what is happening what i imagine is the same thing mostly

[00:30:36] just much more free time some more time to experiment and play with other things and

[00:30:43] at the same time the newsletter continues to be awesome and high quality the podcast continues

[00:30:47] to be awesome and high quality so it’s continuing to put out the same high quality stuff

[00:30:51] just more free time less uh the boulders may be smaller yeah okay so what is free time enable for

[00:31:00] you when you think about i hear your deep commitment to quality products yeah and quality

[00:31:06] output but this longing to feel a little bit more playful or flexible with those parts that

[00:31:14] are essential to you

[00:31:17] very practically it’s time to play around with you know ai tools just like explore and just kind of

[00:31:22] tinker versus like okay all the time i have i need to focus on the newsletter make it better for next

[00:31:27] week oh it’s coming out here’s things i gotta do oh it’s podcast gotta prefer that gotta edit this

[00:31:31] thing so it’s just time to tinker and explore and and just like yeah that kind of thing that

[00:31:37] kind of makes sense and what’s important about exploring and tinkering to you because in the

[00:31:43] work i do i need to stay ahead on where things are going i can’t just you know sit around and

[00:31:47] pontificate from a cloud i need to really understand how things work what’s what’s working what’s not

[00:31:52] what’s real what’s not so being on the ground as much as i can with what’s actually going on versus

[00:31:57] just you know putting out content that makes sense your voice is moving really fast you’re

[00:32:01] i kind of hear you feeling behind even in the way you’re describing what you’re doing

[00:32:06] a good active listening what’s interesting to me is when you’re talking about exploring and

[00:32:13] tinkering when you first said it you said it’s in kind of a spacious

[00:32:17] way like it’s fun to explore and tinker you’re deeply naturally curious you find new insights

[00:32:24] but then i also heard you say and it’s a way to stay ahead i have to do it

[00:32:30] in order to feel like i’m informed so what do you make of that difference yeah uh yeah those

[00:32:39] are two two sides of the coin like there’s like another element of i guess let me answer that

[00:32:43] question i think i think those are both true i don’t know yeah because it’s

[00:32:47] actually like the reason i got into this is because it’s so fun and so interesting just like

[00:32:51] here’s what’s happening here’s what the future yeah advice here’s ways to improve in the work

[00:32:56] that you do so there’s still like i still love it it’s just i have less time to do that part

[00:33:01] and more it’s just like the machine of the treadmill of content content content yeah there’s

[00:33:05] also just like spending more like i didn’t mention this but just spending more time with

[00:33:08] my son and my wife you know that would be really great just to have more freedom to go

[00:33:13] go do stuff which we have a lot of that but more that makes sense

[00:33:17] okay so the the goal that i hear is not so dramatically different from today it’s that

[00:33:24] you hold on to this high quality output you have space for exploring and tinkering and for spending

[00:33:30] quality time with the people you love most yes the one way i’m thinking about as you reflect that

[00:33:36] back is like 25 percent more free time while everything else continues to be awesome and the

[00:33:42] challenge i run into is i sometimes get that extra time and then i fill it with more

[00:33:47] projects and opportunities yeah there’s that like inertia of moving fast taking advantage of the

[00:33:53] moment that’s coming yeah yeah so that’s a perfect shift into um what are your current ways of

[00:33:58] operating that get in the way of having that 25 percent of free time it’s just like agreeing to

[00:34:04] more things just like oh look i’m kind of free right now oh okay let’s do this uh let’s do this

[00:34:08] talk here let’s agree to this thing here it’s so it’s just once i feel freedom i’m like okay i

[00:34:15] could do that other thing and so i commit to more stuff

[00:34:17] yeah and how is that commitment to saying yes to things that come at you serving you

[00:34:22] not great well it’s serving you in some ways like what ben you’re doing it for a reason

[00:34:30] what is it what benefit does it have to you well it depends on the thing you know like i

[00:34:35] actually have a rule of never doing a talk or going on other podcasts or going to events really

[00:34:39] because i find i never really get much out of it and it distracts me from the stuff i could be

[00:34:45] doing so i’ve set up a

[00:34:47] lot of policies of just turning down things that uh don’t serve me but uh i still crumble

[00:34:55] so yeah that’s right so that’s your point there’s you know there’s value here and there

[00:34:59] when i take on more work but and then i end up overworked again yeah i’m hearing there’s just a

[00:35:05] pattern it’s like a reflexive pattern of even though you set a rule for yourself to say no to

[00:35:10] certain things and you seem proud of that boundary you naturally break it or you fall into filling it

[00:35:15] with other things that’s right exactly

[00:35:17] okay so you’re stuck in this kind of addiction to doing more and signing up for more which is so

[00:35:23] normal in our world and probably most listeners can relate to that that’s kind of the soup we

[00:35:28] swim in so we have to be conscious of where what inputs we have around us

[00:35:32] so let’s explore your various options that you have in front of you one that you mentioned

[00:35:41] already you tried was to commit like make a list of the things you don’t want to be doing anymore

[00:35:46] like things you want to do and then you’re like okay i’m gonna do this i’m gonna do this i’m gonna

[00:35:47] say no to and really committing to that and sticking to that what are the other kinds of

[00:35:52] things you could do to help you prioritize and create that sacred 25 percent of extra time for

[00:35:59] yourself something i’ve already done which hasn’t kicked in fully yet but that i’m really excited

[00:36:05] about is i reduce the cadence of my newsletter and podcast which in theory should be a massive

[00:36:11] change but the podcast hasn’t the cadence of the podcast hasn’t shifted down yet it’ll have to go

[00:36:17] up in next year the newsletter cadences i basically changed my promise to readers instead of you will

[00:36:23] receive a newsletter every week now it’s two to four times a month depending on what’s going on

[00:36:27] which uh felt huge the problem is i still like every week i’m like oh and i can write about

[00:36:33] this thing oh every week there’s oh there’s nothing happening i gotta put this out so i’m

[00:36:37] almost not taking advantage of that opportunity uh so something i could do is actually not publish

[00:36:43] every week another is just bring on some more help which is

[00:36:47] difficult because i’ve got a lot of good help and there’s only so many things other people can do

[00:36:52] for me that isn’t writing an awesome newsletter and recording conversations like this yeah but

[00:36:57] i’m always thinking about and i should think deeper about where can people take more load

[00:37:02] off my plate yeah i love that insight if you what i’m hearing is do less in certain areas

[00:37:08] and think about your team and really expanding the capacity of your team

[00:37:14] and be rigorous about the things you can hand off

[00:37:17] you may have limiting beliefs around the things you need to do versus the people on your team

[00:37:21] i might i might and then your point i loved which is just um say uh improve my policies of what i

[00:37:27] say no to that don’t serve me yeah what are the things you could be saying yes to if you said no

[00:37:32] to more things just playing around with stuff just space to explore and tinker and just sit around

[00:37:39] and think versus just go go go go go yeah and i hear i just see you feel so light and excited

[00:37:46] in that like you

[00:37:47] almost are giddy when you think about that spaciousness that’d be so nice and i just want

[00:37:52] to name reflect back to you how special that is and how much more creative you could be in your

[00:37:58] work when you have that space and time and your bucket is full with care i feel that i feel that

[00:38:04] yeah so what’s one thing you could do in the next two weeks that would help you get closer

[00:38:11] to the kind of spaciousness you want to create i love that we’re like as we go through this i’m

[00:38:16] like oops

[00:38:17] thinking about this grow framework and i love how you’re executing like i see it in action yeah i’m

[00:38:21] trying to do very simple coaching right now just yeah yeah this is great it’s really easy to follow

[00:38:27] for your list yeah yeah this is great uh okay so what’s one thing i could do in the next couple

[00:38:32] weeks to help you move forward on this i think one is at least skip a week or two of the newsletter

[00:38:39] and just actually stick to that plan so but it’s tough because the next two weeks i got already

[00:38:44] planned i gotta write i gotta write a gift guide that’s my

[00:38:47] okay so the week after i’ll take a break okay cool so two weeks from the recording this i won’t

[00:38:52] publish a newsletter and then i’m gonna revisit my policies on what i say yes and no to i love

[00:38:59] that think about everything you’re saying yes to and what are things you want to say yes to

[00:39:05] that you could treat it with so really consider that um it’s a trade-off every time you say yes

[00:39:11] to something the more resonant you are with the end state and what’s possible for you

[00:39:17] the easier it is to be disciplined in the near term i love just that element of here’s what you

[00:39:22] 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

[00:39:26] to do exactly yes say like a resonant full-bodied yes to the things that are in hell yes yeah hell

[00:39:32] yes with an exclamation exactly okay well thank you lenny for um letting me just demonstrate what

[00:39:39] powerful questions are and the reason i wanted to do that with you is you know you brought an

[00:39:43] example that’s actually pretty big it’s an emotional thing and it’s an emotional thing and it’s an

[00:39:47] emotional thing it’s a cultural norm it’s a way of being that we’ve all learned to to be through

[00:39:54] growing up in and operating in tech especially so even with that kind of topic using a simple

[00:40:02] grow model can be useful but people are coming at your listeners with topics that are very

[00:40:09] complicated technical urgent but the same kinds of questions unlock new opportunity

[00:40:17] when

[00:40:17] it’s about how to build technical infrastructure or how to uh you know influence the executive

[00:40:23] team or how to ship the go-to-market strategy so i just want a name that’s very transferable

[00:40:28] i love that i got great advice in this conversation already how what a great roi for me at least

[00:40:36] what did it feel like to be coached on your own podcast it was it was it was uh unusual i’m just

[00:40:42] like wait i gotta get back to asking you questions that’s okay all right we can flip it we can flip

[00:40:47] it i do want to name that um typically when you’re coached versus told what to do you’re more bought in

[00:40:53] so if i told you you know lenny i’ve heard all kinds of leaders come to me talking about being

[00:40:59] too busy here’s what you should do write a list of all the things you’re doing write the things

[00:41:05] you’re going to delegate you know cut out 25 of the things on your calendar i could have given

[00:41:10] you a laundry list of things that i thought you should do without much context but you’re the

[00:41:14] expert on your own context and actually what resonates with you so i’m going to give you a

[00:41:17] and you’re much more likely to do it if you came up with it i i was going to mention that earlier

[00:41:23] that is so incredibly true like no one wants to like unless you ask for advice very few people

[00:41:28] are like please tell me what to do just tell me i really love you just unsolicited advice

[00:41:33] like it doesn’t go well yeah and great leaders often say do you want advice or do you want some

[00:41:38] space to think about it like can i you know can i help you think it through or would you like me

[00:41:42] to tell you what i would do and both are fine in certain situations so asking for advice is a good

[00:41:47] thing is useful too yeah okay that was uh that’s such an important element of this that we should

[00:41:52] have mentioned and that’s i’m glad you did yeah okay so i’m gonna go back to asking you questions

[00:41:58] right this is a good segue to something i wanted to spend a little time on which is burnout yeah

[00:42:03] we you know what i’m talking about is stuff that often leads to burnout i’m definitely not burnt

[00:42:08] out but you know this is a common problem in tech where people feel depleted and just go too hard

[00:42:16] and then they so much of the time they’re like oh i’m going to do this i’m going to do this i’m

[00:42:17] people i’ve worked with just left tech i had a call you get airbnb he went he’s like a park ranger

[00:42:21] now in the mirror woods and that’s how far so peaceful and so wonderful but i think that’s

[00:42:27] just people go so hard sometimes and then just get burnt out and never want to do anything like

[00:42:32] this again i know that you spent a lot of time on this with founders and you have a really

[00:42:36] helpful approach so just talk about what you’ve learned about helping

[00:42:41] leaders in tech avoid burnout and feel energized and excited about their work for a long time

[00:42:46] yeah

[00:42:47] well first of all i’m glad you brought it up it’s a huge problem i remember when i was coaching top

[00:42:52] talent at straight patrick coulson is really committed to retaining top talent and i created

[00:42:58] a program with my team for the top 50 executives in the tech side of the house and we looked at

[00:43:05] their engagement scores we did coaching circles and it was so sad to see how exhausted that group

[00:43:13] of incredibly creative and committed leaders was in that moment and i think that’s a really good

[00:43:17] moment and it’s so common that people who start with incredible inspiration and incredible capacity

[00:43:25] start to feel like they’ve been pushing and pushing and pushing for years they’re parenting

[00:43:31] they’re leading crazy things are happening to the business and they just can’t muster the same kind

[00:43:38] of motivation they once had and i see this with my clients all the time so i’ve also witnessed

[00:43:47] people who are still inspired and continually energetic and seem to have some secret well

[00:43:56] of you know some diesel battery or i guess i should say a tesla battery that helps them

[00:44:01] through really hard challenges and they’re still having a good time and so my what i make of that

[00:44:08] is that when people are in their gifts and their strengths firmly most of the time

[00:44:15] they have more energy

[00:44:17] we all have more energy when we’re operating from the things we naturally are good at

[00:44:21] and the things we innately love doing so i try to help my leaders see that they can

[00:44:28] they can design their lives so they’re spending 80 of their time in their gifts

[00:44:32] that seems really ambitious because you’re stuck within a context that requires a lot of you

[00:44:38] especially when you’re uh executive at a huge company

[00:44:41] but i also interact with founders who

[00:44:47] started a company with great inspiration an entrepreneurial vision and their job has

[00:44:54] obviously changed every six months once you fundraise once you grow a team and sometimes

[00:44:59] especially technical founders will start solving a technical problem they’re absolutely obsessed

[00:45:04] with they spend three years doing it the product ships and then they’re stuck managing a board and

[00:45:10] team and they don’t even realize they’re doing a completely different job than the one that played

[00:45:15] to their strengths

[00:45:17] so one tool i like to give is for people to actually take two weeks and every night reflect

[00:45:24] on what’s the five what are the five things today that gave me the most energy

[00:45:29] and what are the five things that depleted my energy the most if you do that for two weeks and

[00:45:34] you look at patterns you can tell what are the natural gifts that i’m living in and what are

[00:45:41] the things that i’m stuck doing that are exhausting and they’re just slowly it’s like a slow leak in

[00:45:47] your gas system and you’re like oh my god i’m so tired i’m so tired i’m so tired i’m so tired

[00:45:47] that over time shows up in your daily amount of energy i so believe this advice is so effective

[00:45:54] this is the way i actually approached when i left my job i very actively did this i paid

[00:46:02] attention every day what gave me energy and what sapped my energy and let me just do more of the

[00:46:09] thing that gave me energy and more less of the thing that saps me i want to talk about just like

[00:46:13] you know there’s only so much you can change but i want to talk about that yeah and that and so

[00:46:16] initially i was like oh my god i’m so tired i’m so tired i’m so tired i’m so tired i’m so tired

[00:46:17] maybe i’ll become an advisor and consultant kind of person i actually found that was super

[00:46:21] depleting for me and doing these calls and talking to people because it’s like surface level you

[00:46:26] know here are some things i would do and it was just so unexciting and energizing but writing was

[00:46:31] really energizing which i never expected and i love that and that’s what i did and i just

[00:46:36] followed that pole and it sounds like maybe you need a refresh let me oh interesting you know

[00:46:43] there’s always more attuning you can do to your gifts like you’re in this amazing

[00:46:47] you’ve clearly been successful for a reason you’re in your strengths and you’re paying

[00:46:51] attention to what brings you energy we can always do that more throughout our life i think it’s a

[00:46:56] process of continually kind of tuning in to where your spark is and protecting that spark

[00:47:03] feeding it i love that insight that just blew my mind so very tactically the way you would do this

[00:47:09] is for two weeks every night is the idea look at reflect back on that day and write down five

[00:47:16] things that gave you energy and more energy and more energy and more energy and more energy and

[00:47:17] energy five things that sappy of energy yeah there’s so many different activities you could

[00:47:20] use so that’s one um i like a activity of actually asking five to ten people in your life with a very

[00:47:27] simple email when i walk in the room what shows up what are my strengths what are the gifts if

[00:47:32] you really don’t know them and you haven’t spent a lot of time in this realm that’s also an

[00:47:37] opportunity of actually asking the people who know you best what your core gifts are and when when do

[00:47:43] you have the most inspiration you can also look through your

[00:47:47] calendar and note themes okay over the last month what are all the things i look at on my calendar

[00:47:52] that i’m excited to do what are the things i dread okay why do i dread those things what do those

[00:47:57] things have in common so there’s various ways you can get to kind of what is your zone of genius

[00:48:01] but what my invitation is to take that really seriously it actually takes risk taking it takes

[00:48:10] intention to design your life around your gifts is there any advice for actually doing this

[00:48:16] say

[00:48:17] I love your ideas i think that the people around you need to be on board and know what are your

[00:48:32] gifts so for example when i was an hr business partner my boss bought into this and i explained

[00:48:38] to her hey i started at stripe because i actually know i’m going to be a coach i’m not going to be

[00:48:43] but i love working with leaders so i’m gonna

[00:48:47] you know do all the compensation strategy and all the org design and i’m going to help

[00:48:51] product and engineering leaders but what i have in the back of my mind is i’m honing my coaching

[00:48:55] skills and so when this opportunity to work on top talent um retention came about it was much

[00:49:04] very aligned in in the realm of coaching and lnd background that i had so she put me on that so

[00:49:09] it’s useful to name it to the people around you what are your gifts what are your interests

[00:49:13] what skills are you really excited to hone so that they are going to be able to help you

[00:49:17] in a contract with you to help you and really apply your gifts to the business’s needs so that’s

[00:49:22] one thing when you’re a founder a ceo when when you have the autonomy to consider what are the

[00:49:28] role scopes around me then you can really hire around it so i have some ceos that i work with

[00:49:35] who are incredible visionaries great strategists really good at you know managing the board hiring

[00:49:40] etc terrible at managing their team hate it so they hire a coo and they work in partnership they

[00:49:47] really internally focused they get to be externally focused that works well it’s a

[00:49:51] symbiotic relationship if you’re honest about your strengths and your weaknesses then you can start

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[00:51:00] slash lenny thanks again to persona for sponsoring this episode it’s really nice to know what you

[00:51:06] want to do and understand where your dream life looks like you also have a job you have manager

[00:51:10] you got things to do you got responsibilities so i guess first of all as you have seen people that

[00:51:17] make a change to do the things to spend more time on their gifts to actually not just be like

[00:51:23] like there is uh you have agency to move in a direction that’ll make you happy is kind of an

[00:51:29] implied piece of this yeah i think sometimes people hire a chief of staff to help them and

[00:51:33] compliment them um sometimes people design their team with strengths and gifts that they don’t have

[00:51:39] so it’s really there you can get creative once you really understand oh these things give me a

[00:51:47] but i still need to fill this need for the business what are all the ways i can do it

[00:51:51] and telling your manager i think is a is such a simple and important part of this telling them

[00:51:58] here’s where i want to go here’s the things i want to get better at here’s the things that give

[00:52:01] me energy can we just try to make as much of my role that yeah especially if you’re executing well

[00:52:06] people want to retain you they want to know what’s going to keep you here for the next five years

[00:52:10] and typically they think that move that means moving up the ladder but maybe it doesn’t for

[00:52:14] you i think it does take the courage to do that and i think it does take the courage to do that and

[00:52:17] i think it does take the courage to move horizontally sometimes to get into your

[00:52:21] strengths and that i mean i’ve moved horizontally a number of times and i love what i do i feel like

[00:52:27] i’m in my natural gifts but it took me a few risks and and some uncomfortable jobs that didn’t

[00:52:33] feel like they were worthy of my experience in order to get there what’s like a good percentage

[00:52:39] of your work life that should be in gifts and things that energize you versus okay i actually

[00:52:45] got my witness test

[00:52:47] 80 that’s the goal that’s the aspiration you’re always going to have 20 of things you don’t love

[00:52:51] doing there’s just the logistics of getting into the zone that you need to be in but i really try

[00:52:59] to push people to think aspirationally that if you’re 80 of the time in your gifts how much

[00:53:04] energy you have to give to the world it’s so much more inspiring so i want to tell you why i’m

[00:53:10] passionate about this topic because it actually is how i ended up as an executive coach so uh

[00:53:17] 10 years ago i was working at a small company called remind and i was running the ux research

[00:53:22] team and the ceo asked me to move in to the product manager role for the core product team

[00:53:29] and i was excited for the opportunity i had non-technical background but i thought hey all

[00:53:36] these strategists are up there creating the roadmap i can do that i know exactly what our

[00:53:41] users need so i was excited for this i you know came into the team there was a lot of people that

[00:53:47] i think 12 senior engineers very opinionated um very skeptical of this non-technical pm but we

[00:53:55] worked together and what i did was i listened i learned what do our users need what does this team

[00:54:01] need what’s working and not working and within a month this team was working well together they

[00:54:06] were you know reviewing each other’s code base they were really disagreeing in a healthy way in

[00:54:11] our team meetings they felt more connected to users and i felt like okay this rhythm’s working

[00:54:17] but what i was also doing is i was at home stressing in the middle of the night about

[00:54:22] the new user experience i couldn’t decide which of the designs to go with i was always over

[00:54:29] leveraging our data scientists and i found myself swirling on decisions that didn’t need to have so

[00:54:35] much stress involved and one day i went for a walk with my colleague zach abrams and he was a great

[00:54:43] product manager and he was listening to me

[00:54:47] ask all these questions about how to sell the vision of what this uh what this product would

[00:54:53] look like in the future and he said rachel you’re a zone of genius or your gift is not being a

[00:55:01] product strategist but i’ve watched you over the last few months and you have gotten the team more

[00:55:07] motivated than i ever could and you’ve influenced the entire executive team behind your ideas and

[00:55:13] that’s impressive you’re a people person

[00:55:17] and at first i was offended what you think i don’t have the ability to be a great product leader

[00:55:23] and yet i i sat with what he said and i knew he was right both my parents are therapists i never

[00:55:29] wanted to be a therapist here i am i’m basically a work therapist i love entrepreneurial energy

[00:55:36] i love big vision but i’m a i’m a people person and i left that and i realized i love what my

[00:55:43] coach does i got trained as a coach i went into hr leadership i got trained as a coach i got trained as a coach

[00:55:47] and zach who was a gifted product strategist went on to lead product at coinbase and brex and most

[00:55:54] recently bridge which was acquired by stripe and he’s still my client and we’ve watched our journeys

[00:56:00] over the last decade and we’ve both been honing our gifts and it’s life is more fun when you’re

[00:56:07] in your gifts and you have more inspiration and capacity to offer the world so i just want to share

[00:56:14] that story because

[00:56:15] you’re a person

[00:56:17] it’s helpful to be honest with the people you care about when they seem energized and when

[00:56:24] they seem depleted because sometimes it’s a wake-up call for people to really think about

[00:56:31] what is their spark and to protect it and to feed it i love that story because i think most people

[00:56:38] when they hear this advice and this kind of topic of okay i i’m feeling depleted i’m feeling burnt

[00:56:44] out i feel like most people jump to you okay but i can’t actually do it

[00:56:47] anything about it i have a job i got responsibilities what what i’m getting from this is there’s

[00:56:52] actually the most important step is jump to figure out what you actually should be doing

[00:56:56] what gives you energy what your gifts are it feels like that’s the biggest gap for people

[00:57:00] because once you know that there are ways to do that talk to your manager hey uh here’s something

[00:57:05] like may not be possible today but here’s where i want to be going here’s what i want to be spending

[00:57:09] time on i love your point you made though about you actually have to be doing well for your

[00:57:14] manager to listen to you can’t just be like sucking and then like oh but i want to work on

[00:57:17] strategy yeah well it’s it’s no one else’s job to help you live in your gifts and what i notice in

[00:57:24] big companies is people are often annoyed or frustrated with their management for not making

[00:57:29] their job more interesting it’s like no your manager’s job is to help you perform in the

[00:57:34] job you were hired to do it’s your job to navigate your career so over the arc of your career how do

[00:57:41] you match your gifts with the world’s needs

[00:57:44] and if it’s that if the world right now is your company how do you understand the needs enough so

[00:57:50] that you can apply your strengths to those needs this reminds me there’s a couple guests i’ve had

[00:57:55] on the podcast who did this they’re both founders so it’s you know this is specific to founders but

[00:58:00] rahul vor at superhuman he realized he’s just not uh he’s not like the best uh executor in the

[00:58:06] operations person so he hired a president that took all that off his plate and then uh darmesh

[00:58:12] co-founder of hubspot

[00:58:14] he knew from the beginning he didn’t want to manage people so he made a rule with his co-founder

[00:58:17] i will never have reports yeah and he’s the cto i believe and has zero reports has no one on ones

[00:58:23] yeah and i think that it’s a beautiful thing to recognize that but then to actually address the

[00:58:29] needs of those reports also i think often people know oh i don’t want to have anyone once but just

[00:58:35] not having anyone manage those people is not going to be healthy for your company so you have to both

[00:58:40] take your strength seriously and actively manage around your business so i think that’s a really

[00:58:44] is there any maybe last piece of advice on this topic of helping people get to a place where

[00:58:49] they’re feeling much less depleted and just more energized at work i would start small you don’t

[00:58:54] have to leave your job and redesign your life you can stop going to the optional things that

[00:59:00] are exhausting you can leave space between the things that are depleting that you have to go to

[00:59:07] to go outside and go on a 30-minute walk and re you know refuel your tank start with

[00:59:14] tomorrow what are the three things you’re going to do to like plug up that gas leak and

[00:59:20] re-energize your spark it might even be you love to read and you’re going to start reading 30

[00:59:26] minutes before you go to sleep every night it doesn’t have to be a dramatic life change but

[00:59:31] recognize that only you know what is resonant and what is depleting and it’s your job to take that

[00:59:37] seriously if you want to show up purposeful and impactful in the world i love that advice i’ve

[00:59:42] actually started reading before bed i’ve actually started reading before bed i’ve actually started

[00:59:44] for 30 minutes and that’s been so joyful like a physical book with a little night yeah i agree

[00:59:49] i love i love a physical book i have a kindle i got all the things but a physical book on the

[00:59:54] couch is the best yeah it’s just the nightlight is key because something at nighttime it’s like

[00:59:58] you know like okay so we’ve been talking mostly right so far about kind of individual

[01:00:05] improvement how to figure out what you should be working on just uh helping learning to coach

[01:00:11] things like that i want to kind of take us up a little

[01:00:14] a level above and talk about team skills help people get better at working with other people

[01:00:19] something that you’re uh in many ways known for is helping co-founders build better relationships

[01:00:25] and in my experience is one of the most challenging parts of starting a company is

[01:00:30] the co-founder relationship you a lot of people don’t realize what they’re getting into you’re

[01:00:33] basically getting married to this person in like a very high stress situation and you sometimes

[01:00:37] don’t know much about them exactly and then you not working well together is just a huge issue

[01:00:42] because that all trickles down and then you’re like oh my god i’m not going to be able to do this

[01:00:44] and everyone sees it and and you know when co-founders leave it’s really bad for everyone

[01:00:48] so let me just ask you this what have you found most helpful in helping co-founders

[01:00:53] build great relationships stay happy and productive yeah thanks for asking this i

[01:00:58] love working with co-founders because i think your core values as a person come out when they

[01:01:04] interact with someone else’s core values conflict healthy conflict or otherwise is actually where

[01:01:10] your core values come out so it’s fascinating to watch people

[01:01:14] try to do something incredibly hard in the context of someone else’s vision someone else’s

[01:01:20] strengths and weaknesses and navigate that together so there’s so much energy in the

[01:01:24] co-founder dynamic for me and for co-founders themselves it’s actually something that people

[01:01:29] don’t feel comfortable going to their board about or talking to that many people about

[01:01:33] because it’s a private matter it’s almost like in a marriage you go see a couples therapist

[01:01:38] but you don’t tell all your friends that you can’t stand your partner but it keeps you up at

[01:01:42] night so it’s a really tough thing to do and i think it’s a really important thing to do and i

[01:01:44] think it’s a really tender important relationship and there aren’t enough supports for co-founders

[01:01:48] to navigate it it’s very normal in fact i know you probably know this stat 65 percent of startups

[01:01:54] fail because of co-founder conflict and co-founders are in a moment where they’re trying

[01:02:02] to build the future for their business but also trying to build their own livelihood so there’s

[01:02:08] so much at stake to get along with your co-founder and i think that the core at its core

[01:02:14] what you need in a healthy relationship is one self-awareness what do i bring into this dynamic

[01:02:21] and how am i being experienced by the other person what does this other person bring into

[01:02:27] the dynamic and how am i reacting to that so the first is just collective awareness about what is

[01:02:35] our dynamic i like to use the enneagram for this but there’s all kinds of tools self-awareness

[01:02:40] tools that you can use to give a common language to

[01:02:44] what is my thing and what is your thing a very classic one has to do with roles cto’s tend to

[01:02:51] be skeptics they’re they love facts they seek knowledge they want depth of awareness and

[01:02:58] understanding and they also like to be self-sufficient this is a total generalization

[01:03:03] but i’ve seen this pattern over and over again the ceo is the person who had to sell the vision

[01:03:09] they’re a person who loves big picture vision strategy they often are greeted

[01:03:13] influence and they’re a person who loves big picture vision strategy they’re a person who

[01:03:14] they love to sell ahead of the reality of what the company’s actually built this creates an

[01:03:20] inherent tension between blind optimism and skepticism and it’s a dance that these two

[01:03:26] roles play together so the first part is knowing the dance you’re in so you’re not just stepping on

[01:03:31] each other’s toes blindly the second step is actually being conscious about the commitment

[01:03:38] you’re making to your relationship so in a marriage for example people you know i i

[01:03:44] talk about co-founder vows and recommitments and renewals because in a marriage you get married and

[01:03:50] a lot of times people build a family and then they think oh the relationship will just continue

[01:03:55] because we’re around each other all the time we’re doing this thing together but just like

[01:04:00] couples need a date night co-founders need time and space to connect with each other to come

[01:04:06] together and say how’s this working for you are we still aligned on our vision and our strategy

[01:04:11] how are we working together what

[01:04:14] I doing that’s pissing you off? What are the things that have gone unsaid and that we need

[01:04:18] to talk about? But if you’re just in the hustle and bustle of running and scaling your startup,

[01:04:24] you don’t make time for that conversation. So I think it’s incredibly important for

[01:04:29] co-founders to make space for their relationship, whether that’s a dinner every other week,

[01:04:35] whether that’s going out to lunch regularly, whether that’s just touching base business-wise,

[01:04:41] but having an in-person quarterly check-in. That space is critical for the health of a

[01:04:48] co-founder relationship. On that second piece, the vows idea is such a good idea.

[01:04:52] Is that something you actually recommend? Like, here’s what I vow to do?

[01:04:55] Yeah, here’s what I commit to do. So I have recently, I actually wrote an article with

[01:05:00] First Round, and we created a document to help co-founders think about what to integrate into

[01:05:05] their check-in. So we put out weekly check-in, monthly check-in, and annual. And just

[01:05:11] quickly, we put out a document to help co-founders think about what to integrate into their check-in.

[01:05:11] Questions to sit down and ask each other. Active listening skills will come in handy in those

[01:05:16] conversations. But it’s about taking space out of hustling and running the business to think about

[01:05:24] the business from a kind of rather, I like to say, instead of being on the dance floor,

[01:05:29] you need time on the balcony to look down at what’s happening. How are we doing? Is this

[01:05:35] still working for both of us? And the vows are really about how are we going to be together?

[01:05:40] How are we going to show up? Like, what’s our culture that we’re creating? Even if you don’t

[01:05:44] want to go through a whole culture exercise early on in building your company, you should have some

[01:05:49] sense of how you want to show up for each other. How are we going to make decisions?

[01:05:54] How are we going to deal with conflict? These are things you can go into intentionally and

[01:06:01] design with your co-founder. Awesome. We’re going to link to that post. The first step,

[01:06:06] Enneagram sounds like that’s what you recommend. And this is basically a personality profile.

[01:06:10] That a lot of people love. I really like the Enneagram. I think you can also

[01:06:14] simply tell each other, here are my strengths. Here’s what I see as my weaknesses. And what

[01:06:20] do you think? Give me some feedback. Do you agree? And you can do that with each other without

[01:06:24] any personality assessment. If you want to just be scrappy and have an open, connected conversation

[01:06:30] about the, you can even say, what are the gifts I bring and the weaknesses I have? And how will

[01:06:37] I cover those? How will I lean into my gifts? How will I cover my weaknesses?

[01:06:40] And how will you? And then I think it’s worthwhile having a conversation about

[01:06:45] what are the gaps neither of us cover that we’re likely going to need as we build this business?

[01:06:51] What do you recommend people do when they are just like, our relationship isn’t working grades?

[01:06:56] Like there’s a lot of tension. All this advice we’ve been talking about is like,

[01:06:59] at the beginning, here’s things you can do to set things up for success.

[01:07:03] Understand what you’re good at, what you’re bringing to the table. Consciously commit to,

[01:07:06] here’s what I’m going to do. Here’s what you’re going to do. Have these dinners

[01:07:10] I love this metaphor of going out on the balcony and just reflecting on how it’s going.

[01:07:16] So that’s all really great. What if you’re just ready in it and just like,

[01:07:20] it’s really annoying and I don’t like this person that much or it’s so much tension

[01:07:23] constantly. What are a couple of things they can do this week, next week?

[01:07:26] Co-founders typically come to me either in this early phase where they want to intentionally

[01:07:31] build something great and they want to set it up for success. More often, co-founders come

[01:07:38] when they’re really frustrated with one another.

[01:07:40] They feel the tension is palpable. They can’t stand it anymore, but they’re still really

[01:07:45] deeply committed to the business. So they don’t see an out. And they knew that at some point,

[01:07:52] they really loved this co-founder. So they see a possibility of recovering.

[01:07:57] And that’s why they want to go get a coach. I’m going to give you an example of this PR duo

[01:08:02] running a fierce business, scaling really fast. And at one point when they started,

[01:08:09] you had the vision. You had the vision. You had the vision. You had the vision. You had the vision.

[01:08:10] You had the vision. You had the vision. You had the vision. You had the vision. You had the vision.

[01:08:10] Who was great at selling business. They were both incredible with PR. And the partner was

[01:08:16] incredible operationally. So as the business scaled, one took on a lot more business development

[01:08:22] and the other took on all the internal things, but was exhausted by all this people management

[01:08:27] and all of the elements of kind of running a scaled team that she didn’t expect to have to do.

[01:08:35] And when they came, I think both of them weren’t sure, can we figure this out? Do we want to do

[01:08:40] this? Do we want to just sell this thing? Do we want to keep going? And I think someone said,

[01:08:46] end it or send it, was what one co-founder said to me. They’re coming at this decision point.

[01:08:54] And what I saw them do is, one, they named current state really well. They were both able

[01:09:00] to share. We did use a 360. So they got feedback from their teams and then shared it with one

[01:09:07] another. But they were able to be open and vulnerable. And they were able to share it with

[01:09:10] in what was working and what wasn’t working. Not immediately, but over time. And they realized

[01:09:18] they used to love being partners in this work. But as they began to lead different teams,

[01:09:25] they grew very distant from one another. They were living on opposite sides of the country

[01:09:28] and actually just coming together and realizing what each other was missing and how lonely it is

[01:09:35] to lead this scaling company without each other’s support and how they actually

[01:09:39] needed to be able to do this. And I think that’s what I saw. And I think that’s what I saw.

[01:09:40] And I think that’s what I saw. And I think that’s what I saw. And I think that’s what I saw.

[01:09:40] to their strengths and didn’t have it

[01:09:43] was an important start to their healing. And over our coaching, they turned back towards each other

[01:09:51] and they created more of a rhythm of how they would get together without me involved.

[01:09:57] And they ended coaching after our arc feeling renewed and really recommitted. They made some

[01:10:04] changes on their leadership team to fill their gaps. They also started, I think, meeting once

[01:10:11] a week virtually, and they started a cadence of getting together in person quarterly.

[01:10:17] And I don’t mean to say that just that time means you’re going to heal. Sometimes coming together

[01:10:23] and really grappling. I had one last week where we all came together. We had a great

[01:10:28] full day in-person discussion about how they were making this co-founder duo,

[01:10:33] how they were making decisions. And after that conversation, it was really clear that

[01:10:40] one of the things that we were talking about was how we were making decisions.

[01:10:41] One of the co-founders was unhappy and didn’t appreciate the other one and was not going to

[01:10:47] change and realized he was a big part of the problem and I think is going to leave the

[01:10:51] business. But that’s still success because it’s clarity. You’re not muddling in the dark,

[01:10:58] frustrated, unconscious about the interpersonal dynamics you’re in. You’re making a choice based

[01:11:05] on your strengths and what the business needs and this relationship dynamic that you’re in.

[01:11:11] To either be in it or to lovingly step out of it.

[01:11:16] I love how similar this is to just a marriage. All this stuff here,

[01:11:19] like this is the same sort of thing you do.

[01:11:21] Totally. I mean, a marriage, you’re building a life with a partner.

[01:11:24] So the only difference is a marriage is rooted in sexual attraction and love.

[01:11:29] And that’s not the case always in the co-founder dynamic. But I have worked with couples who are

[01:11:36] also co-founders, but there should be some element of love for your co-founder.

[01:11:41] In fact, I think that when you work closely with colleagues and you really are able to

[01:11:46] see their gifts and enable them, you can’t help but love them.

[01:11:51] That’s a big statement. The other takeaway here is that just get coaching. It feels like that’s

[01:11:57] the solution if things are just not working great. Like there’s only so far you can get just

[01:12:00] talking. It takes an evolved facilitator, like one of the co-founders being able to hold space

[01:12:07] for both their frustration and their empathy.

[01:12:11] So in a dynamic that is challenging, so outside support is useful. Sometimes it’s actually a team

[01:12:19] member. It’s an HR leader. It’s the GC who happens to have great people skills. You don’t always

[01:12:25] need a coach, but you need space to be vulnerable, open, and curious. So if you can create that on

[01:12:31] your own, that’s great. I think it’s definitely possible.

[01:12:35] Outside of the co-founder relationship, do you have any just tactical tips for people to

[01:12:40] improve their interpersonal?

[01:12:41] Interpersonal skills with just team members, anyone they work with, just people that may

[01:12:45] struggle. Like, man, I have a hard time with this person. I just have a hard time with a lot of

[01:12:49] people.

[01:12:50] First of all, people, when they want to have a conflict or they want to engage in something

[01:12:55] that’s not working, they come in armored and ready to prove their point. It’s natural. You’ve

[01:13:01] been thinking about this, perseverating over whether you should mention it. You finally get

[01:13:06] to the point of engaging. And often there’s a misguided

[01:13:11] view that the goal is to convince the other person that what they’re doing is wrong.

[01:13:17] Actually, the goal of any conflict is to create mutual understanding.

[01:13:22] So when I go in to have a conversation with, let’s say, my husband, who’s not doing his share

[01:13:28] of the parenting, my goal is to help him understand what I’m struggling with

[01:13:33] so that he can empathize, see clearly what’s happening, and perhaps meet my

[01:13:41] needs in some way. But it’s not for me to prove to him how

[01:13:47] little he’s doing in the house. Because he might have a totally

[01:13:51] different story about what’s happening. So I’m going to give you a

[01:13:55] framework that I like, that many of my clients use.

[01:13:59] It’s from Marshall Rosenberg’s Nonviolent Communication.

[01:14:03] It’s a book and a framework. So it’s four steps.

[01:14:07] The first step is observations.

[01:14:10] So my job is to note what is happening factually.

[01:14:16] For example, I noticed that in the last three sprint planning meetings,

[01:14:22] you didn’t invite me to those conversations or share with me the roadmap.

[01:14:28] That’s an observation. It’s a fact. I could take a picture of it and no one would argue with it.

[01:14:34] The next step is feelings. So I’m going to express my feelings without blame.

[01:14:39] So I’m going to express my feelings without blame.

[01:14:40] So I felt anxious not knowing what was on the roadmap for the week.

[01:14:45] I felt confused about whether that meeting happened or not because I wasn’t included.

[01:14:51] So this is me sharing my feelings so the other party can empathize and understand what I’m going through

[01:14:55] without being defensive. The third step is needs.

[01:15:01] What are my universal human needs related to this topic?

[01:15:04] We all have needs. This is not requiring anything of the other person,

[01:15:08] just helping them understand my needs.

[01:15:10] So I have a need for clarity. I have a need for collaboration.

[01:15:16] I have a need for connection, whatever that is.

[01:15:20] And lastly, the step is to make a request.

[01:15:24] Now in this model, the request is an olive branch to help the other person meet you and see you.

[01:15:30] It shouldn’t be something that’s impossible to do.

[01:15:32] It should be actually something quite small and easy to achieve

[01:15:35] for the other person to feel successful in connecting to you and understanding you.

[01:15:40] So in this case, I might make a request.

[01:15:44] I’d like to ask you next time you have a sprint planning meeting to include me as optional

[01:15:49] or to send me the roadmap afterwards that you align on.

[01:15:54] Now the other person doesn’t have to meet my request.

[01:15:57] They might make a counterproposal, but the most important thing of this model

[01:16:02] and this conversation is that the other person understands what I’m going through

[01:16:06] and they don’t feel reactive so that we can have a mutual conversation.

[01:16:10] Wow.

[01:16:12] This point about how when you’re trying to convince someone of something,

[01:16:19] when something is going wrong,

[01:16:21] this point that your goal is not to convince them,

[01:16:24] that your goal is to have mutual understanding,

[01:16:26] that just blew my mind.

[01:16:28] It’s a shift.

[01:16:28] And I think it’s going to change my life.

[01:16:31] Wow.

[01:16:32] Lenny, try this with your wife tonight.

[01:16:33] NVC is a powerful tool.

[01:16:36] And actually, it’s very akin to most models.

[01:16:40] And I think it’s going to change my life.

[01:16:40] That are about connection.

[01:16:43] The Stanford Business School course that has a T,

[01:16:45] it’s called Touchy Feely that everybody loves.

[01:16:47] Yeah, we’ve had Carol on the podcast.

[01:16:49] Great.

[01:16:49] Yeah.

[01:16:49] So Carol Robbins created this movement, right?

[01:16:52] There’s Lit.

[01:16:52] A lot of founders go to her model that’s for founders.

[01:16:55] There’s a tech.

[01:16:56] And this is all about, they talk about a net,

[01:16:59] that you can talk about your feelings and your reaction.

[01:17:02] But as soon as you cross the net to blaming someone else

[01:17:05] or making an assumption,

[01:17:07] they’re going to have a defensive response.

[01:17:09] But you can be incredibly bold and brave

[01:17:12] if you stay on your side of the net.

[01:17:14] So this model helps you do that

[01:17:15] because it’s really about sharing your emotions and your needs

[01:17:19] and making a request without blame.

[01:17:21] Yeah.

[01:17:22] So what I was going to say

[01:17:22] as you were going through this framework is it’s all,

[01:17:25] it’s here’s me.

[01:17:26] Here’s what I saw.

[01:17:27] Here’s what I’m feeling.

[01:17:28] Here’s what I need.

[01:17:29] And then here, now that you have that in context,

[01:17:31] here’s something I’m asking for versus you did this

[01:17:34] and you’re feeling this and you thought this.

[01:17:37] Exactly.

[01:17:37] It also acknowledges that professionally,

[01:17:39] professionals have feelings.

[01:17:40] I think that we operate in tech,

[01:17:42] like we’re supposed to give all of ourselves,

[01:17:46] all of our time, all of our energy to this endeavor.

[01:17:48] And it’s purely logical.

[01:17:51] It’s not at all true.

[01:17:52] It’s completely emotional.

[01:17:54] And if we ignore our feelings,

[01:17:57] they will bubble up

[01:17:58] and we will be unconsciously acting from them.

[01:18:01] And there’s kind of this implicit power here

[01:18:03] that if the person cares about you and loves you

[01:18:07] or values your relationship,

[01:18:08] knowing that,

[01:18:09] this makes them feel bad,

[01:18:11] will make them want to change.

[01:18:12] It’s not like you need to tell them,

[01:18:14] change this thing.

[01:18:14] It’s, oh, I didn’t realize this made you upset

[01:18:17] or that you have this need.

[01:18:18] And now that I know that, okay, now I see why this is important to you.

[01:18:21] That’s exactly right.

[01:18:22] And sometimes the other person will hear that

[01:18:26] and have a different story or different perspective, right?

[01:18:29] So they might say, okay, I can honor that request

[01:18:32] or I hear that request and I hear your feelings,

[01:18:36] but let me explain what happened for me.

[01:18:39] And one way you could do that is,

[01:18:41] are you open to hearing that?

[01:18:42] So they’re able to share their side too.

[01:18:46] You don’t have to just agree with the person’s request.

[01:18:48] As long as you’re setting this tone,

[01:18:51] the other person’s more likely to contribute in a way

[01:18:54] that achieves mutual understanding

[01:18:56] because they’re going to share,

[01:18:57] once you’re vulnerable,

[01:18:58] they’re going to share their vulnerability.

[01:19:00] Let me remind folks of the framework.

[01:19:03] I’m going to try using this.

[01:19:04] I wish it was a handy acronym.

[01:19:06] I know.

[01:19:06] Off and error.

[01:19:08] So the framework is share what you’ve observed,

[01:19:11] just the facts of what is happening.

[01:19:12] Just simply, here’s, I saw you didn’t close the fridge fully.

[01:19:17] Your feelings of how that made you feel,

[01:19:20] the needs that your core human need

[01:19:22] that drives that feeling, I imagine.

[01:19:25] And then the request you have of the person.

[01:19:28] Yes.

[01:19:29] And I want to make one note I forgot to say,

[01:19:30] which is feelings are emotions.

[01:19:33] So sometimes people say things like,

[01:19:35] I feel like you’re being a jerk.

[01:19:37] I feel like you’re being a jerk.

[01:19:38] So that’s not a feeling, obviously.

[01:19:41] A feeling is a sensation in your body

[01:19:44] that results in an emotion.

[01:19:45] So naming a feeling is actually not easy

[01:19:48] for technical leaders sometimes.

[01:19:50] I want to make that point

[01:19:52] because emotions are what get you

[01:19:55] to the underlying humanity of connection.

[01:20:00] Emotions are the key to soliciting empathy.

[01:20:05] Are there like phrases that are just examples

[01:20:07] of non-feeling?

[01:20:08] Like using the word you

[01:20:11] in the way you describe a feeling

[01:20:12] probably is not a good sign.

[01:20:14] Exactly.

[01:20:15] If you can say like, I feel like,

[01:20:17] even if you add like, or I feel that,

[01:20:20] you’re probably going to add a fact.

[01:20:21] It should be an emotion word after I feel.

[01:20:24] So don’t say like, don’t say you, don’t say that.

[01:20:27] Yeah, exactly.

[01:20:29] Awesome.

[01:20:29] Sort of along this topic,

[01:20:31] I chatted with a number of clients

[01:20:33] that have worked with you over the years.

[01:20:35] And one of the most common themes that they said,

[01:20:37] you help them,

[01:20:38] is having difficult conversations.

[01:20:41] And I think we covered actually much of this

[01:20:43] in what we just talked about.

[01:20:45] But I’m curious if there’s any other advice you have

[01:20:47] for helping people have difficult conversations.

[01:20:50] Let me read a quote from one of your clients.

[01:20:52] Oh, wow.

[01:20:52] I love this.

[01:20:54] So she said,

[01:20:55] Rachel is exceptional making difficult decisions clear

[01:20:58] and making it feel possible

[01:20:59] to get these decisions actualized.

[01:21:02] Is there anything more there for,

[01:21:04] because difficult conversations are difficult.

[01:21:07] How do we help people?

[01:21:08] Make them less difficult.

[01:21:10] Any tips?

[01:21:11] Yeah.

[01:21:11] Well, first of all,

[01:21:13] difficult conversations makes you want to run away.

[01:21:16] The marketing on conflict is poor.

[01:21:21] So I want to reframe that.

[01:21:23] My belief is when we feel internally ambivalent,

[01:21:27] we have two inner parts at war.

[01:21:29] And there’s something really beautiful

[01:21:31] and important to pay attention to.

[01:21:33] There’s something to learn when we have ambivalence.

[01:21:36] When we are in conflict,

[01:21:38] something important is at stake.

[01:21:42] We care deeply about what we’re building,

[01:21:45] about the person that’s letting us down.

[01:21:47] So the reason it’s hard

[01:21:50] is because there’s such an emotional component to it.

[01:21:54] And there’s something to learn from it.

[01:21:56] So first, I want leaders who are listening to think,

[01:22:01] this is hard because I have something to learn here

[01:22:04] and because it matters.

[01:22:06] So instead of avoiding it and running away,

[01:22:08] I’m going to lean into this moment.

[01:22:11] And I’m going to come out of it,

[01:22:13] not just having solved this dynamic

[01:22:15] and not just having said my piece,

[01:22:18] but having built a skill.

[01:22:22] The reason I focus on interpersonal dynamics

[01:22:25] is because the quality of our relationships

[01:22:28] determines the quality of our life.

[01:22:30] I really believe that.

[01:22:32] And if you cannot have conflict,

[01:22:35] you can’t have healthy relationships.

[01:22:37] We are going to do this.

[01:22:38] We are going to do this.

[01:22:38] I disagree with the people we love or care about

[01:22:40] or are building a business with.

[01:22:43] So first, I just want listeners to reframe

[01:22:45] ambivalence and interpersonal challenge

[01:22:49] to think of them as a growth opportunity.

[01:22:55] Second, there is always something that we’re doing

[01:23:00] to contribute to the conflict,

[01:23:01] even if it feels like the other person’s insane

[01:23:04] and is driving us crazy and we’re the innocent party.

[01:23:08] So entering any conflict conversation

[01:23:12] with humility and curiosity

[01:23:15] about the other person’s experience

[01:23:18] is critical to setting the table

[01:23:20] for a commitment to come out better and stronger.

[01:23:26] So no model, NBC or otherwise,

[01:23:29] can fix a person who’s coming in rigid

[01:23:32] and full of blame.

[01:23:34] I really love the conversation

[01:23:38] about the 15 Commitments to Conscious Leaders.

[01:23:40] I don’t know if you know that book.

[01:23:41] But one of the concepts is about taking 100% responsibility,

[01:23:47] not being in the world of blame,

[01:23:49] being a victim or being a hero.

[01:23:52] And I see many leaders when they’re in a challenging

[01:23:56] interpersonal conflict, being in victimhood,

[01:24:00] being in blame or being in hero,

[01:24:02] I’m just going to do it for them and forget it.

[01:24:05] You know, they’re so, they’re having such a hard time.

[01:24:08] I’m getting this done.

[01:24:09] I’m just going to do it.

[01:24:10] Instead, take responsibility for your part.

[01:24:13] What is my piece in making this dynamic happen?

[01:24:16] And how can I address it?

[01:24:18] That makes me think about Jerry Colonna was on the podcast

[01:24:20] and he has this famous line that I’ve always remembered.

[01:24:24] How are you complicit in the creating the conditions

[01:24:27] that you claim you don’t want?

[01:24:29] Yes, I love that.

[01:24:30] Love that question.

[01:24:31] And there’s so many, like there’s three parts

[01:24:33] to that whole question.

[01:24:34] I won’t get into it.

[01:24:34] But what you’re sharing here is think about that.

[01:24:38] Figure it out.

[01:24:38] Figure out how, because your point is you’re always

[01:24:40] somehow complicit in creating the issue

[01:24:42] you’re complaining about and use that to help

[01:24:44] kind of put down the defense of the person.

[01:24:46] Like, here’s what I’ve contributed to this problem.

[01:24:50] Do you use the nonviolent communication framework?

[01:24:53] And I don’t know, is that just a general way

[01:24:54] of trying to have difficult conversations

[01:24:56] or is there not a framework?

[01:24:58] Yeah, no, I think that’s a great framework

[01:24:59] for when you want to go interact with someone

[01:25:02] around something that’s not working for you.

[01:25:03] Like, I think typically a difficult conversation arises

[01:25:06] because some people, you know,

[01:25:08] feelings are coming up for you

[01:25:09] and you have a need that’s not being met.

[01:25:12] And so that’s the instigator to know,

[01:25:14] okay, I need to talk to this person.

[01:25:15] We need to clear this up.

[01:25:17] For example, I was working with a CEO

[01:25:19] whose co-founder was constantly undercutting his decisions

[01:25:24] and criticizing him.

[01:25:27] And there was something happening

[01:25:28] where they’d gone from being this great dynamic duo,

[01:25:31] fundraised, hired a few leaders,

[01:25:34] and then all of a sudden he was getting

[01:25:37] kind of daggers thrown at him all the time.

[01:25:39] And it was exhausting and frustrating and confusing.

[01:25:42] So that was a time where he used NVC

[01:25:44] to address what is happening here.

[01:25:47] And it turned out that the co-founder

[01:25:49] was really frustrated with how he was spending his time.

[01:25:53] He didn’t want him to be off selling.

[01:25:54] He wanted him to be helping him with product vision.

[01:25:58] And they had a totally different conception

[01:25:59] of how the CEO should be spending his time.

[01:26:02] Awesome.

[01:26:02] Just to remind folks of the NVC framework,

[01:26:04] because this is the thing that’s hard in the moment.

[01:26:06] Like, oh, what should I be saying?

[01:26:08] Observe, feelings, needs, request.

[01:26:11] Yeah, exactly.

[01:26:12] And there’s a nonviolent communication book

[01:26:14] if folks are into the framework and want to check it out.

[01:26:17] People need a little…

[01:26:18] Like, who was it you said,

[01:26:19] when your client’s tattooed,

[01:26:20] there is the vision he had on…

[01:26:22] Okay, let’s just get something…

[01:26:23] Maybe don’t tattoo NVC.

[01:26:24] It doesn’t have a good acronym, you know?

[01:26:26] You could just print it out

[01:26:27] and put it right next to your screen or something.

[01:26:29] All right, all right.

[01:26:30] No tattoos.

[01:26:33] I just want to highlight the first point you made

[01:26:35] in this answer of having difficult conversations.

[01:26:37] And then I have one more question for you.

[01:26:39] Just this point about

[01:26:40] if there’s something you’re afraid of,

[01:26:43] that is a sign you should do that.

[01:26:46] There’s a quote I often think of,

[01:26:48] the cave you fear contains the treasure you seek.

[01:26:52] And it’s almost…

[01:26:53] And the advice there is just

[01:26:54] the thing you’re afraid of is a compass to

[01:26:56] the thing you should do

[01:26:57] because there’s something important there.

[01:26:59] Yeah, it’s like, what’s important here?

[01:27:00] What do I have to learn here?

[01:27:01] Is a question you can ask yourself

[01:27:03] when you’re avoiding something.

[01:27:05] I often see this in talent management situations.

[01:27:09] A CEO has an underperforming COO.

[01:27:13] They’re avoiding a conversation

[01:27:15] because they keep getting let down.

[01:27:16] And actually, they kind of know deep down,

[01:27:19] this is not working out.

[01:27:21] They don’t want to face it.

[01:27:22] It’s too much work.

[01:27:24] They need to just keep plowing forward.

[01:27:27] And when we really take space

[01:27:29] to think about their feelings and needs,

[01:27:33] they realize…

[01:27:33] I ask them,

[01:27:35] would you enthusiastically…

[01:27:35] would you enthusiastically re-hire this person

[01:27:37] for the same role?

[01:27:38] Which is the question we always ask at Stripe.

[01:27:41] And when the answer is no to that,

[01:27:44] no matter how many difficult conversations you have,

[01:27:47] this is not going to work.

[01:27:49] So then you have to take action.

[01:27:51] And even engaging in the hard conversation

[01:27:54] and seeing what happens

[01:27:55] can lead you to the clarity

[01:27:57] that you need to take action

[01:27:59] on talent that’s not working.

[01:28:01] That is a really cool tip.

[01:28:02] I did not know Stripe operated that way.

[01:28:04] We had the CTO,

[01:28:05] of Netflix on the podcast,

[01:28:07] Elizabeth Stone,

[01:28:08] and this is very much how they operate.

[01:28:10] They’re always asking a question like that.

[01:28:13] The way you phrased it was,

[01:28:14] would I enthusiastically re-hire this person

[01:28:17] for the same role?

[01:28:18] Exactly.

[01:28:19] It’s very clarifying because it’s binary.

[01:28:21] People have a physical sense.

[01:28:23] Just like we talked about a full body yes before,

[01:28:26] you have an immediate reaction

[01:28:28] that is honest to that question

[01:28:30] that provides clarity.

[01:28:33] And the answer isn’t…

[01:28:35] If it’s no, it’s not.

[01:28:35] Fire them.

[01:28:36] You need to do something about it.

[01:28:38] It could be talk to them about it,

[01:28:40] put them on a performance plan,

[01:28:41] put them in a different role.

[01:28:42] It doesn’t mean you have to fire them immediately.

[01:28:44] So it’s not necessarily as scary

[01:28:46] as it sounds if you say no.

[01:28:47] Yeah, I think that also it depends

[01:28:49] on the stage of business you’re in.

[01:28:51] So I see a lot of companies

[01:28:52] build a leadership team

[01:28:54] and then a year later,

[01:28:57] the size and stage of their business

[01:28:59] is dramatically different.

[01:29:00] And they start to realize,

[01:29:01] oh, the CFO that was really fine back then

[01:29:04] is now…

[01:29:06] Completely wrong.

[01:29:08] He should be the controller.

[01:29:09] Okay, great.

[01:29:10] So reckon with that.

[01:29:12] Like, recognize that

[01:29:13] in how you’re interacting

[01:29:14] with your current CFO.

[01:29:16] Put out a search.

[01:29:16] Like, there’s many things you can do

[01:29:18] that aren’t firing someone.

[01:29:19] But in quickly scaling businesses,

[01:29:21] it’s natural that the leadership team’s job

[01:29:23] will change

[01:29:24] and that you’ll have to make some evolution

[01:29:27] over time.

[01:29:29] And I guess it’s very important

[01:29:30] to highlight the importance

[01:29:31] of operating this way

[01:29:32] if you’re trying to build

[01:29:33] a really successful company

[01:29:34] is that should be the…

[01:29:35] The bar is if you would not

[01:29:38] enthusiastically rehire this person

[01:29:39] for this role.

[01:29:40] If you’re trying to build something

[01:29:41] that’s never been built before

[01:29:42] and build a company

[01:29:44] that actually works out really well,

[01:29:46] you need to really

[01:29:47] only hire people around

[01:29:48] that are hitting that bar.

[01:29:50] Yeah, my perspective,

[01:29:51] you know, I talked at the beginning

[01:29:53] about how I’m obsessed

[01:29:54] with the human side

[01:29:55] of business building.

[01:29:56] And my belief is that talent

[01:29:59] and the environment

[01:30:00] that you put your talent in

[01:30:01] is everything.

[01:30:03] Yes, building a product

[01:30:05] and a business,

[01:30:05] it’s about building

[01:30:06] something that users need.

[01:30:08] It’s about product market fit

[01:30:09] and then the wave you’re on.

[01:30:11] Timing is important, right?

[01:30:13] You’re going to build

[01:30:13] a different size business

[01:30:15] if you’re in a sector

[01:30:16] that’s not growing

[01:30:17] than right now

[01:30:17] if you’re in the middle of AI.

[01:30:19] True, you’re writing a timing wave

[01:30:21] and you’re solving a core need.

[01:30:24] But everything besides that

[01:30:26] is so human.

[01:30:27] It’s about talent

[01:30:28] and it’s about the environment

[01:30:29] that you put that talent in.

[01:30:32] So you need to create the conditions

[01:30:34] such that your talent

[01:30:35] can thrive.

[01:30:36] Such a simple concept

[01:30:39] that I think people overlook

[01:30:40] is just everything you do

[01:30:42] is going to be the people

[01:30:43] that you have around you

[01:30:45] and the environment

[01:30:45] you create for them to operate.

[01:30:48] I think your point about

[01:30:49] when you’re doing something difficult,

[01:30:50] just to close out this element,

[01:30:52] I love this idea

[01:30:53] that if it feels hard,

[01:30:55] think of it as a learning opportunity.

[01:30:57] I think anyone listening to this

[01:30:58] is like, oh, cool,

[01:30:59] I’m going to learn something.

[01:31:00] I’m going to get better.

[01:31:01] It’s such a easier,

[01:31:02] more motivating way

[01:31:03] of approaching something

[01:31:03] that’s difficult.

[01:31:04] Yeah, and I want to make

[01:31:06] a distinction between that

[01:31:07] and what we talked about earlier,

[01:31:10] which was lean into your strengths.

[01:31:13] Because I don’t believe people

[01:31:15] should suffer through the day

[01:31:16] grinding, doing work that’s depleting.

[01:31:19] That’s not a learning opportunity.

[01:31:22] Interpersonally,

[01:31:23] when you’re avoiding something,

[01:31:25] it’s because you care about something.

[01:31:28] Avoiding your emotions

[01:31:29] is what I want to

[01:31:31] encourage people against.

[01:31:33] We have to feel like

[01:31:34] all the way through,

[01:31:36] be present to our feelings

[01:31:37] and interact with others

[01:31:39] in a way that acknowledges our feelings.

[01:31:42] That’s what I want to encourage.

[01:31:43] Because actually,

[01:31:44] that’s not deadening,

[01:31:45] that’s enlivening.

[01:31:46] And there’s learning there.

[01:31:48] A final area

[01:31:49] I want to spend a little time on

[01:31:50] is something that I’ve heard

[01:31:51] from everybody that you work with,

[01:31:53] which is the way

[01:31:54] that you help them operate.

[01:31:55] So you just talked about

[01:31:56] the importance of the people you hire

[01:31:58] and how the environment

[01:31:59] you create for them.

[01:32:00] And something that you help leaders do

[01:32:03] is create a,

[01:32:04] very specific way of operating

[01:32:06] around a one-page plan

[01:32:07] and how that kind of trickles down

[01:32:08] and just makes everything

[01:32:09] at a company more effective.

[01:32:11] Talk about this one-page plan,

[01:32:12] how you recommend companies operate

[01:32:15] with this.

[01:32:17] Yeah, thanks for asking that question.

[01:32:18] I think typically companies

[01:32:21] have complicated the process

[01:32:25] of aligning their vision,

[01:32:28] their strategy,

[01:32:29] their goals,

[01:32:30] and the way people behave

[01:32:32] with each other, their values.

[01:32:33] So that all of these things

[01:32:35] live in different places,

[01:32:37] are talked about to a different degree,

[01:32:39] resonate to employees differently.

[01:32:41] And if you asked anyone at the company,

[01:32:44] what are your top three priorities

[01:32:45] and how do they relate to the vision?

[01:32:47] It’s not an easy answer.

[01:32:49] So the reason I like

[01:32:50] the one-page plan concept

[01:32:52] is it’s simplifying.

[01:32:55] It’s a way for the leadership team

[01:32:57] to come together and align

[01:32:59] around what are we doing here?

[01:33:01] What is our role in it?

[01:33:02] And how do we do that?

[01:33:03] How do we communicate it

[01:33:04] so that the whole company has clarity

[01:33:07] and knows how the work they’re doing

[01:33:09] ladders up to our big picture vision

[01:33:11] that we’re all committed to?

[01:33:13] So I actually got this idea

[01:33:15] of the one-page plan from Alpine Investors.

[01:33:18] They do a one-page,

[01:33:19] they have something called

[01:33:21] the people-first operating rhythm,

[01:33:23] and they’ve successfully implemented that

[01:33:25] at their portfolio companies.

[01:33:27] And I work in concert with Alpine,

[01:33:29] so I work with some of their portfolio CEOs

[01:33:31] to execute that.

[01:33:33] So it’s not just about a one-page plan.

[01:33:37] It puts your vision and your values

[01:33:39] on the first column,

[01:33:40] your strategic intentions

[01:33:42] and your KPIs on the second column,

[01:33:44] your annual goals on the third,

[01:33:47] and your quarterly goals on the fourth.

[01:33:49] So that no matter what you’re talking about

[01:33:52] in terms of what are we doing for the next year

[01:33:55] or the next quarter,

[01:33:56] how do we prioritize?

[01:33:58] It’s always in tandem with your core KPIs,

[01:34:01] your strategy, and your vision.

[01:34:03] And I love how they instituted that

[01:34:06] with their portfolio,

[01:34:07] and I saw the power of it.

[01:34:08] They’ve collected some data

[01:34:10] that their portfolio companies

[01:34:12] that actually institute

[01:34:13] the people-first operating rhythm

[01:34:15] result in higher returns.

[01:34:17] So they’re very committed to this strategy.

[01:34:19] And after operating with CEOs in their rhythm,

[01:34:22] I took some of those ideas

[01:34:24] and started to help other founders

[01:34:26] and other leaders

[01:34:27] with some of the same concepts in my own way.

[01:34:30] We’re going to hopefully link to a template

[01:34:31] of this one-page plan.

[01:34:33] Yeah, sure.

[01:34:33] We’re happy to share.

[01:34:34] Okay, so let’s do that.

[01:34:35] And then what kind of impact do you see

[01:34:37] from companies starting to operate this way

[01:34:39] to motivate people to do this?

[01:34:41] Yeah, what I see is clarity and alignment.

[01:34:44] And I also see more connection.

[01:34:46] So I want to name that

[01:34:47] it’s not just about having a plan.

[01:34:49] It’s about how you create it,

[01:34:51] how you reflect on it,

[01:34:52] and how you come together around it

[01:34:55] to celebrate wins.

[01:34:56] So in my opinion,

[01:34:58] a very under-attended-to part

[01:35:00] of building a business

[01:35:02] is an operating rhythm.

[01:35:05] When do you come together

[01:35:06] to kick off the year

[01:35:07] and share your strategy and vision again

[01:35:10] and talk about the goals?

[01:35:12] When do you come together

[01:35:13] to reflect on what’s working and not working?

[01:35:15] And how do you do that?

[01:35:16] And in what groups?

[01:35:18] And are you honest

[01:35:19] or are you just kind of doing it

[01:35:21] as a quick exercise

[01:35:22] to move on to what’s pressing?

[01:35:25] So just like I said in co-founder dynamics,

[01:35:27] a key is to step out of the dance floor

[01:35:29] and to get onto the balcony.

[01:35:32] Executive teams leading a complex business

[01:35:35] need time away from being in the business

[01:35:38] to work on the business.

[01:35:41] So around this one-page plan,

[01:35:43] the reason I like a rhythm

[01:35:44] is you can kick off the year with the plan.

[01:35:46] That’s really simple, easy to understand.

[01:35:48] Everyone can have it accessible.

[01:35:50] And every quarter,

[01:35:51] you can get together to reflect

[01:35:53] what worked, what didn’t work.

[01:35:55] I really like the question,

[01:35:57] what’s an inconvenient truth?

[01:36:00] They are the things

[01:36:01] that need to be talked about

[01:36:03] that no one’s talking about

[01:36:04] because you’re too busy.

[01:36:06] That’s the power of combining a simple plan,

[01:36:09] whether it’s one page or not,

[01:36:11] that aligns you from the top to the bottom,

[01:36:14] your vision all the way down

[01:36:15] to your quarterly goals.

[01:36:17] And a time where you stop, pause,

[01:36:21] discuss, reflect,

[01:36:23] have a little spacious energy.

[01:36:25] It’s not unlike what you said

[01:36:27] about your own time.

[01:36:29] You are the executive team.

[01:36:31] You want a little bit of spacious time

[01:36:34] to tinker, reflect, create,

[01:36:38] and come back to the meaningful work

[01:36:40] you’re doing more energized.

[01:36:42] And leadership teams need that too.

[01:36:44] The way Alpine investors,

[01:36:45] Graham Weaver, he was on the podcast.

[01:36:47] I saw that.

[01:36:48] I saw that.

[01:36:49] I love that.

[01:36:50] Okay, final, final question.

[01:36:51] I want to take us to AI Corner

[01:36:52] before we get to a very exciting lightning round.

[01:36:55] I’m going to do kind of a tweaked version.

[01:36:57] Usually ask people just how has AI

[01:36:58] impacted their work in life?

[01:37:00] I guess that is the question here.

[01:37:01] Just how has AI changed,

[01:37:03] I guess, coaching as a, you know, as a coach,

[01:37:05] but also just from a client’s perspective,

[01:37:08] how are people using AI to help them

[01:37:10] in their, I guess, life

[01:37:11] from a coaching perspective?

[01:37:13] Yeah, it’s a great question.

[01:37:15] So as a coach, I use AI in a couple key ways

[01:37:18] that I’m grateful for.

[01:37:19] One, I use Granola,

[01:37:21] which I saw you give away to your listeners.

[01:37:23] One free year of Granola

[01:37:24] if you become an annual subscriber

[01:37:25] of Lenny’s newsletter.

[01:37:26] There you go.

[01:37:27] There you go.

[01:37:28] So I use Granola to take notes

[01:37:31] in our sessions

[01:37:31] so I can be fully present with my clients

[01:37:33] and I can give them a synthesis

[01:37:35] of what happened

[01:37:36] and the next steps they committed to

[01:37:38] after our session.

[01:37:40] I also use it,

[01:37:42] I put them in a folder for every client

[01:37:44] and so I can look at insights

[01:37:45] across our work together.

[01:37:47] What are the deeper things that are happening?

[01:37:49] What are the patterns that are taking place?

[01:37:51] I have these in my head,

[01:37:52] but actually it’s a great tool

[01:37:54] to see over time,

[01:37:55] oh yeah, we talked about that in our first session.

[01:37:58] Let’s bring that back

[01:37:59] because that’s what you’re struggling with now.

[01:38:01] So it helps me create the kind of transformation

[01:38:05] that I want for all my clients.

[01:38:08] Secondly, I just use ChatGPT

[01:38:12] to help me plan my retreats.

[01:38:13] I run a women’s organization

[01:38:15] and we have eight retreats a year

[01:38:17] and it’s a great tool

[01:38:19] to think expansively about new activities

[01:38:22] once I’ve gotten the core objectives down

[01:38:25] and I have a bunch of ideas about what I want to do.

[01:38:28] It gives me new creative ideas.

[01:38:30] So I can put,

[01:38:31] like here’s my objective,

[01:38:32] here’s my goal,

[01:38:33] here’s my audience,

[01:38:34] here’s my last retreat that I ran.

[01:38:37] I kind of want three new ideas for this session.

[01:38:40] So it’ll give me kind of creative energy

[01:38:43] that I otherwise would need to get together

[01:38:45] with other coaches to discuss

[01:38:47] and I do that too.

[01:38:50] Finally, I’m experimenting with AI

[01:38:54] in a way to support my clients between sessions.

[01:38:58] So I’ve gotten some feedback from my clients

[01:39:00] that they would like me to do that.

[01:39:01] They would like more interaction between our sessions

[01:39:04] and they’re always allowed to email me or text me.

[01:39:07] I’m available to them,

[01:39:08] but I think they want to be really respectful of my time.

[01:39:11] And so some people do reach out and ask me questions

[01:39:14] and other people wait for our session.

[01:39:17] So I’m curious about the future of coaching,

[01:39:20] how in between sessions,

[01:39:22] clients can get access to more of an AI support

[01:39:26] where the bot has all of their context.

[01:39:31] So that’s their development plan

[01:39:33] that we create at the beginning.

[01:39:35] So that’s their goals for our work together,

[01:39:37] how they want to grow.

[01:39:38] Some of my core frameworks and my beliefs and my training

[01:39:42] and the granola notes from all of our sessions.

[01:39:46] So that they can access between just some extra spot support.

[01:39:51] They’re going into this conversation.

[01:39:52] How should they approach it?

[01:39:53] They’re anxious about this team meeting.

[01:39:56] How can they make the most of it?

[01:39:58] More tactical support.

[01:40:00] Personal coaching as still critical for what is your vision of your life?

[01:40:07] How do you want to shift your core behavior to align with that vision?

[01:40:10] But that AI can play a real helpful role in between on the tactics.

[01:40:15] That is super cool.

[01:40:16] So that’s something you already do where they have access to this kind of…

[01:40:19] It’s something I’m building right now.

[01:40:21] I don’t have that yet.

[01:40:22] Okay, that is great.

[01:40:23] That is a really good idea.

[01:40:25] It’s not replacing coaching and therapists, let’s say,

[01:40:28] but it’s adding a lot more.

[01:40:30] In between time where you could just talk to us

[01:40:32] based on everything you’ve talked about,

[01:40:33] all the frameworks that you use.

[01:40:35] That is extremely cool.

[01:40:36] All right, there’s a billion-dollar company coming.

[01:40:38] I don’t want to build that.

[01:40:42] It’s not your zone of genius.

[01:40:44] Exactly.

[01:40:47] Rachel, is there anything else that you want to share

[01:40:51] or leave listeners with before we get to our very exciting lightning round?

[01:40:55] What I want to share is that the world is getting more lonely.

[01:41:00] There’s a lot of research on this,

[01:41:01] but it’s also obvious in my coaching sessions

[01:41:04] that people feel more alienated from one another.

[01:41:08] And actually building businesses is an inherently human endeavor.

[01:41:13] So I’m a fan of this AI boom.

[01:41:17] I appreciate that we have more technology at our fingertips than ever before.

[01:41:22] But I want to encourage listeners to think of themselves as leaders

[01:41:28] who bring humans together to self-actualize

[01:41:32] and that they have to actively overcome the default state,

[01:41:38] which is blind, grind, and loneliness.

[01:41:44] So I think this is a call to action for your listeners

[01:41:48] to connect with the people around them,

[01:41:51] lead healthier teams,

[01:41:53] create environments where connection is inevitable,

[01:41:56] and that they will,

[01:41:57] have more fun and build better businesses because of that.

[01:42:02] What a beautiful way to end it.

[01:42:04] With that, we’ve reached our very exciting lightning round.

[01:42:07] I’ve got five questions for you.

[01:42:09] Are you ready?

[01:42:10] I am ready.

[01:42:11] First question.

[01:42:12] What are two or three books that you find yourself recommending most to other people?

[01:42:15] One of them I said before,

[01:42:17] The Fifteen Commitments of Conscious Leaders.

[01:42:20] And I Love Designing Your Life by Bill Burnett.

[01:42:23] I love that book too.

[01:42:25] People don’t talk about that book enough.

[01:42:26] Mm-hmm.

[01:42:28] Next question.

[01:42:29] Favorite recent movie or TV show you’ve really enjoyed?

[01:42:31] Oh, God.

[01:42:32] I just went to K-pop Demon Hunters with my daughter.

[01:42:34] It’s so embarrassing.

[01:42:35] But that’s what we dress as for Halloween,

[01:42:37] like everyone else in the world.

[01:42:38] I have not seen that.

[01:42:39] I hear everyone talking about it.

[01:42:40] I’m going to try to avoid it, I think.

[01:42:42] Next question.

[01:42:43] Favorite product you have recently discovered that you really love?

[01:42:46] Could be an app, could be a gadget, could be clothes.

[01:42:48] I really love Loom.

[01:42:51] I’ve been recording trainings on Loom for some of my clients

[01:42:55] that are, it’s a scaled holding company.

[01:42:57] So I’m able to scale training in a really human, connected way.

[01:43:01] Do you have a favorite life motto that you often come back to

[01:43:04] in work or in life?

[01:43:05] I have a quote that is on my desk.

[01:43:09] And I love it.

[01:43:10] Ready?

[01:43:11] If you can see your path laid out in front of you,

[01:43:14] step by step, it’s not your path.

[01:43:17] Your own path you make with every step you take,

[01:43:21] that’s why it’s your path.

[01:43:23] That’s a Joseph Campbell quote.

[01:43:25] Beautiful.

[01:43:27] Final question.

[01:43:29] You’ve got two kids, you said.

[01:43:31] Do you have any favorite children’s books that you most love reading to them

[01:43:34] that they’ve loved most?

[01:43:35] Oh my gosh.

[01:43:36] So my daughter is really into Roald Dahl.

[01:43:38] I love Roald Dahl because he’s completely irreverent

[01:43:43] and he has a crazy imagination.

[01:43:45] So we’ve been reading Witches, Matilda, all of his books.

[01:43:49] And both my kids love it.

[01:43:52] So they’re five and seven.

[01:43:53] Have you seen the Wes Anderson book?

[01:43:54] Have you seen the Wes Anderson stories of his stories?

[01:43:57] Some of them.

[01:43:58] Yeah, they’re great.

[01:43:59] Yeah.

[01:44:00] They’re so amazing.

[01:44:01] Oh my God.

[01:44:02] And it’s like Roald Dahl is like they,

[01:44:03] I think it’s personifying him like he’s like a character in the story.

[01:44:06] Yeah.

[01:44:07] I mean, he’s a character from what I hear about his life.

[01:44:09] Rachel, this was incredible.

[01:44:11] I feel like we’ve very much accomplished what I set out to do

[01:44:13] is just give people all this advice that they never have access to

[01:44:17] that costs tens of thousands of dollars.

[01:44:20] I think we’re going to help a lot of people improve their lives and their careers.

[01:44:23] Thank you so much for being here.

[01:44:26] Absolutely.

[01:44:27] Thanks for having me.

[01:44:28] I almost forgot to ask you two final questions.

[01:44:30] Where can folks find me if they want to reach out,

[01:44:32] maybe consider working with you?

[01:44:34] And how can listeners be useful to you?

[01:44:36] Yeah.

[01:44:37] Find me at LockettCoaching.com.

[01:44:39] And how can listeners be useful?

[01:44:41] Listeners should turn towards each other,

[01:44:43] build great relationships,

[01:44:45] and send CEOs and co-founders my way if they need coaching.

[01:44:48] Thank you so much for being here.

[01:44:50] Thanks for having me.

[01:44:51] Take care, Lenny.

[01:44:52] Bye, everyone.

[01:44:53] Bye.

[01:44:54] Thank you so much for listening.

[01:44:56] If you found this valuable,

[01:44:57] you can subscribe to the show on Apple Podcasts, Spotify,

[01:45:00] or your favorite podcast app.

[01:45:02] Also, please consider giving us a rating or leaving a review

[01:45:05] as that really helps other listeners find the podcast.

[01:45:08] You can find all past episodes or learn more about the show

[01:45:11] at Lenny’sPodcast.com.

[01:45:14] See you in the next episode.

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