How to unlock your product leadership skills | Ken Norton, Ex-Google

[00:00] Part of what I think is pretty exciting [00:03] about product management is [00:06] You are a leader from day one. [00:08] in product management. [00:10] Right. And, and, you know, [00:12] There's leadership all over the place, but that's sort of your job. You're a leader. You don't have... [00:16] any formal authority. [00:18] But you're a leader. You're expected to lead. [00:22] Over his 14-year career at Google, Ken Norton led product teams that build Google Docs, Google Calendar, Google Maps, [00:29] and even did a stint at Google Ventures. [00:31] The products that he's helped craft are now used by over 3 billion people. [00:36] Today, Ken is a full-time executive coach specializing at working with product leaders. And in our conversation, we cover the creative versus reactive mindset, [00:45] why the art of product management is much more important than the science of product management, how to get over imposter syndrome, the most common PM blind spots, how to find a coach, and how to know if a coach is right for you, [00:57] and so much more. [00:59] I hope that you enjoy this episode with Ken Norton. [01:03] If you're setting up your analytics stack, but you're not using Amplitude, what are you doing? Amplitude is the number one most popular analytics solution in the world, used by both big companies like Shopify, Instacart, and Atlassian, and also most tech startups. Amplitude has everything you need, including a powerful and fully self-service analytics product, experimentation platform, and even an integrated customer data platform to help you understand your users like never before.

[01:33] your team's self-service product data to understand your users, drive conversions, and increase engagement, growth, and revenue. Ditch your vanity metrics, trust your data, work smarter, and grow your business. Try Amplitude for free. Just visit Amplitude.com to get started. [01:52] Have you heard of Lenny's Job Board? Well, if you're hiring or open to a new gig, have I got the site for you. Lenny'sjobs.com If you're a hiring manager, sign up and get access to hundreds of hand-curated people who are open to new opportunities. Thousands of people apply, and I personally review and accept just 10% of them to be part of this collective. You won't find a better place to hire product managers and growth people. And if you're someone who's looking around for something new, join the collective. [02:22] It's free, you can be anonymous and hide yourself from any company. You can also leave anytime and you'll only hear from companies that you want to hear from. [02:31] check out Lenny's jobs.com. [02:33] to learn more. [02:34] you [02:38] Welcome to the podcast, Ken. I am so honored to have you here. You're such a legend of product managers and product management circles. [02:46] Your writing has had so much influence on so many people, including myself. [02:51] And if nothing else, you've led to many donuts being purchased by tech companies over the years. So thanks for being here. [02:59] Well, thank you, and thanks for having me. [03:01] feelings mutual obviously big fan of your work and all the things you've done for the community and

[03:06] and this podcast, which has been fantastic. [03:09] humbled and excited to be here. And yes, I do think that I'm at least maybe partially responsible for the [03:15] at least a lot of consumption of donuts over these years. [03:19] Are you tired of people asking you about donuts? [03:22] I'll never get tired of it. [03:24] Back when... [03:26] When well back when we met with people in person, you know, people would bring me donuts and and never got tired of it. And nor did any of the people that I worked with who got to eat those donuts get tired of it. So no, no, I'll never get tired of donuts. [03:38] Someone on Twitter asked what's [03:40] What's like a digital equivalent of bringing the donuts now that we're kind of in a remote world? Do you have any... [03:45] advice on that. [03:48] That's a great question. I don't, [03:50] I'm not even sure if the physical... [03:52] equivalent of donuts is donuts. I mean, when I came up with that, I think it was really to [03:58] to be a metaphor around [04:02] Being sort of a servant leader, bringing, you know, whatever needs to be done, sort of filling the white space, filling the gaps, whatever sort of needed to happen. So it's not doesn't always have to be donuts. [04:13] Um, [04:13] I did put that question out to some of the readers of my newsletter a while ago, maybe early in the pandemic and got a lot of really interesting ideas and [04:21] Um, [04:21] Maybe that was at a place where people had a little bit more patience for it. [04:25] happy hours over Zoom and stuff like that. Maybe that patience has worn out. The idea that I loved the most was actual donuts. There was a PM who... [04:33] got DoorDash codes, [04:36] and found the best local donut place for each of the people on the team and basically sent them a code and said, "Click here and order the donuts to come to your house whenever you want them."

[04:45] Maybe at least partially the digital equivalent of the donuts might be actual donuts. Decentralized donuts. [04:51] Decentralized donuts on the blockchain. [04:55] Let's not go there. I don't know what that is. So I was perusing your career path ahead of this chat. He had this pretty wild career. [05:04] You were an engineer initially and then you were CTO. [05:07] at a part of NBC, then you're a founder. [05:11] And then you spent 14 years at Google working on products that folks may have heard of, like Google Docs and Google Calendar and Google Maps. [05:19] and you've also done a bunch of writing, [05:22] and then more recently you've become a full-time executive coach focusing on product people [05:26] I have so many questions I'd love to ask about your career and learnings along the way. [05:30] and the writing but um it actually left to spend most of our time talking about the coaching [05:34] and things that you've learned through that experience. [05:37] And so I have a couple questions just off the bat. [05:40] What does an executive coach actually do? Like, what kinds of things are you helping people with? What does a session look like? [05:46] And then two, just how did you decide you wanted to be a coach full time after leaving Google? [05:50] Yeah, that's a great question. And, and, [05:52] I think coaching... [05:55] does mean a lot of different things and maybe sort of depends on who you talk to it is it is a little bit of a [06:00] kind of who you are, your style, your approach. Some people [06:05] are calling themselves coaches doing more mentoring more advice other people are maybe more like me more peer coaching [06:12] You know, to me, I see [06:14] executive coaching as a partnership or like creative partnership.

[06:18] And it's all about helping [06:20] my client reach [06:23] their goals, their potential, whatever that. [06:25] whatever that means to them. Right. So [06:28] important thing about coaching is the definition of success does belong to the client i don't have an agenda [06:33] I don't have a... [06:34] set of things I'm trying to share, teach, learn. It really is fundamentally up to them, which means every client is completely different. They have different sense of where they want to go. [06:44] different barriers that might be standing in their way. [06:48] I my coaching practice, I coach the whole person. So there is no restriction on what we might talk on, what we might work on together. It's not limited to products, not even limited to work or even leadership. [06:59] It's wherever they want to go, whatever, you know, change transformation means to them. [07:05] Um, [07:07] As coaches, we bring a bunch of tools to the conversation. I, you know. [07:10] The most important ones, honestly, are probably listening and [07:14] curiosity, intuition, open-mindedness, really there to sort of help [07:20] challenge them to see things in different ways, help them tap into their imagination, [07:25] figure out when there might be underlying beliefs. [07:28] help them connect dots that need to be connected, help them disconnect things that feel connected. There's a lot of sort of exploration to it. [07:35] um [07:36] It's very jazz-like. I've... [07:38] My love of jazz has been shared before, but there is a sort of improvisation to it. And what coaching is really powerful is you may not necessarily know where you're going when you start. [07:47] And you sort of follow wherever there is

[07:50] meaning and change for that individual, wherever it is they want to go. [07:54] Um, [07:55] And the question around like what brought me into it, [07:58] was actually kind of interesting and [08:01] As I honestly working with my own executive coach started to figure out what it is that mattered to me and what I liked, what my values were, what my purpose was. [08:09] started to unpack that [08:11] I love... [08:13] deeply connecting with people. And I love helping people change and grow. [08:18] And the moments when I had the opportunity to do that, [08:22] as a manager, as a product leader, were the most fulfilling parts of my career. And so I started to unpack that and figure out [08:28] What would it look like if that was what I did? [08:31] And the other part of the journey was [08:34] For several years at Google, I worked at GV, Google Ventures, Google's venture capital arm. [08:39] And I had the opportunity to work with [08:41] with founders and product leaders in the portfolio. [08:45] And I started to sort of simultaneously recognize the [08:48] the shortcomings of giving advice. [08:51] Because it seemed like, you know, well, I can meet with these folks. I could tell them what I did. [08:55] I can tell them what Google did and that'll sort of answer all their questions. [08:59] And you start to realize advice is not super... [09:02] Not as powerful as you might think it is. Like it's a. [09:05] It's a little bit like, [09:07] cotton candy [09:08] doesn't have a lot of nutrition. You get a nice sugar high, you feel great. Both sides feel happy. But then sort of a couple of weeks later, a couple of months later, nothing's really changed. [09:16] And, [09:17] And that's because it doesn't often... [09:19] confront the real problem.

[09:21] it often isn't relevant, like what worked for us at Google. [09:25] may not have worked anywhere else. [09:28] It may not even have worked at Google for all I know. I feel like there were years at Google where [09:33] All we were doing was making things worse by showing up and we should have all gone, sat on a beach somewhere and life, the company would have grown even faster. So who knows? [09:41] And so it was sort of these kind of twin pillars of [09:46] So wanting to figure out where I could do what I like the most. [09:50] And then also recognizing that [09:52] Where growth comes from is less around advice and sort of telling people what to do and more about sort of helping them figure out [09:59] their own path, their own way. [10:01] And then that ultimately sort of brought me into, hey, I want to do this full time. And that's what I've been doing ever since. [10:08] When do you find people come to you to get advice and coaching? What kind of like what kind of clients do you find you end up working with? [10:15] That's a great question. Generally speaking, I work with [10:19] senior product leaders, however you want to define that. Typically, these are chief product officers, VPs of product at startups. [10:27] largely director level and above at big, bigger tech companies. [10:32] Some [10:33] CEOs, other C-level execs in there. I think really anyone that sort of considers themselves in a product leadership role. [10:40] Often they come to me because they're at a [10:42] there's a career milestone. [10:44] Or a crossroads. [10:46] Um... [10:47] And it could be that they've now find themselves in the position of being a CPO for the first time. Maybe there's a new industry change or they've,

[10:56] gone from a big company to a startup and [10:59] sort of have this sense of, you know, what got me here isn't going to get me there. And that's oftentimes when they reach out for coaching. [11:06] Um. [11:07] And I think my clients are also very introspective and, and, [11:13] surrounded by great [11:15] mentors and advisors and have all sorts of [11:19] people in their life who can help them, but are realizing that a lot of the work is going to be internal work that's going to get them to the next level. And so this sort of transformation is going to be just as much [11:30] what I need to do as who I am. And that's often when people come to me. [11:34] You said that a lot of coaching is the way you coach is about the whole person. [11:39] And I'm curious, I don't know if there's an answer to this, but [11:42] When people come to get help and coaching, [11:45] How much of their [11:46] blocks, I guess. [11:49] are like rooted in, you know, their... [11:52] Regular... [11:53] life and versus like skills, technical skills and [11:56] and more like the PME product leadership side, if that makes sense. Yeah, I think, well, hmm. [12:03] Let me maybe try to illustrate this with an example from my life right now. And if you'll indulge me, I'm going to go a little bit afield here, but I promise it'll come. Let's do it. [12:14] So we are teaching... [12:18] our [redacted address]. So he just got his driver's permit. [12:22] Um, [12:23] Do you remember when you learned how to drive winning? I do. Yep. Yeah. Yeah. So it's scary. I don't know if you know how your parents might have felt. Nope. I know how it is on the other side of it. It's a whole new journey.

[12:37] And look, he you know, he's a smart kid. He's he's you know, he's going to do great. [12:42] But it helped me [12:44] actually think back to when I learned how to drive and actually [12:47] What I think is maybe a little bit more important here is before you learn to drive. [12:51] And so if you think about it as when you're a kid, [12:54] You just cars just go places like you get strapped in and you just wait and you get impatient and then eventually you go somewhere and you're not even. [13:03] consciously aware of the concept of driving. [13:07] just cars just happen and you're sort of, you know, not even aware of it. [13:10] Um, [13:11] As you get a little bit older, you start to become curious. You start to figure out [13:15] oh, you know, that wheel has something to do with it. You turn the wheel, maybe you start to understand there's pedals. [13:21] But it all just seems really simple, right? Just like you get in the car and you drive it and you go somewhere. [13:27] Maybe as you get older, [13:29] You end up maybe even being a little bit of a smart aleck about how easy it looks. When you start talking to your parents about like, it doesn't look hard, I can do this. [13:37] Now, [13:39] Suddenly you're behind the wheel of the car. This is what my son is doing. [13:44] And [13:45] wow, is it different than you thought it was going to be? Is it way more complicated than [13:51] Um, you have to remember to check your mirrors. You got to, [13:55] Look before you turn. You didn't even know what that sign meant. You didn't know what those stripes meant. It is just overloading. [14:01] with complication. [14:03] and [14:04] your sort of internal... [14:07] mindset for confronting this challenge.

[14:11] is not going to suit you, right? The way you used to sort of approach the world. [14:14] Um, [14:15] And maybe put it in like product leadership. [14:18] product terms. [14:19] Everyone around you has got some real pithy advice about the things you're forgetting to do. It's sort of like, hey, you forgot. Don't forget to check your mirror. [14:26] Um, [14:27] Everyone's got a framework. [14:28] Right? That's why... [14:30] you know, [14:31] Ah, do you know about the 10 and 2 framework? [14:33] Wait, what's the 10 and 2 for me? Oh, you just put your left hand on the 10, your right hand on the 2 o'clock. [14:38] That's the only thing you're missing. Here's a great... [14:41] Medium post about that. [14:43] And then you're like, that's not the problem. This is this is a problem is I might I have not adapted to the complexity of the world around me. Right. [14:52] And so there is this sense that [14:54] What is interesting about driving is the world hasn't gotten any more complex. Driving has always been driving, but now your place in the world has shifted such that [15:02] the internal meaning making and self-complexity that is required [15:07] requires a complete reboot of the internal operating system in order to allow you to thrive there. [15:13] And so, [15:14] When you talk about this kind of question of [15:18] How much of this is skills? How much of this is [15:21] tactics how much of this is learning versus how much is internal growth the answer is it's both [15:26] But the shift that is required is [15:28] very much around how you're [15:31] inner self. [15:33] can make meaning and respond to the demands of the world around you so that you can succeed and thrive in this sort of this mindset shift that happens.

[15:41] You know, the skills matter, but by this point, you're sort of beyond the place where you've learned the skills. [15:47] There's mastering the skills, but there is the sense of, [15:50] you know, what developmental psychologists call [15:53] you know, sort of self-complexity, the ability to sort of respond and adapt to that. [15:57] And so I think we go through a lot of those shifts in our career. Right. The driving example is simple. [16:02] um actually probably too simple because the world is actually getting more complex for those of us that work in product i mean every day something changes it [16:09] forces us to [16:11] to respond and adapt. So there aren't even rules of the road. [16:15] in product. [16:16] But I think this is sort of what we're talking about, this question of, [16:20] the internal operating system I've developed and my ability to [16:24] to restructure it such that I can succeed given the demands that have been placed upon me. [16:31] What an amazing analogy. Totally hits home. [16:35] in a good and bad way. [16:37] This is a it's a really good segue to something I wanted to chat about, something that we we talked about before the recording. [16:43] which is what you're finding to be one of the bigger unlocks for your clients. And it's also a concept that you've been spending a lot of time refining. [16:50] and your finding is helping people [16:52] shift and specifically around shift their leadership mindset. [16:57] and so i'd love to just hear you talk through your thinking there yeah it it does sort of lead into this and [17:03] you know, maybe another... [17:06] analogy that might [17:08] that might work for [17:09] your listeners, if you think about

[17:12] you know, product management, [17:14] your career arc [17:16] and sort of where you are challenged from a mindset perspective. [17:20] In some ways, it does feel like the [17:23] the early part of your career [17:25] you're learning to play a video game. [17:27] Right. There's a [17:28] Hopefully there's a tutorial, like your first job is, you know, sort of learning the ropes and be teaching you. You maybe have managers that are, [17:35] You know, giving you simple little missions that you can succeed at. And if you fail, the consequences aren't bad. And you sort of like it does feel like a little bit and I've talked to, you know, I felt this way, but talked to a lot of people or in their career, it does feel like you're trying to learn the rules of the game. [17:47] trying to figure out the physics and [17:50] You want to run up the score and [17:52] you get better at playing the game you know you fail but you start to develop some confidence that [17:57] when you fail, you'll learn from it, you'll get better. [17:59] You get really good at the game, right? You get promoted, you get rewarded, you unlock new levels, teach other people how to play the game, start to feel really awesome. [18:08] about yourself. [18:09] um [18:10] But then... [18:11] suddenly you're put in a place where you realize that the rules of the game aren't so black and white there's a [18:18] Maybe there's a long delay now between when you get to see what you did and the score of it. Things start to behave in unexpected ways. [18:26] um the physics start to get weird you're on a level where you're floating i don't know what the right metaphor is here but [18:32] you start to recognize that there's been this huge change. [18:36] And, [18:37] The most frightening part about it is you look around and everyone is looking at you like you're the designer of the game.

[18:43] And you thought you were playing. And that's often what it feels like when you when you move into a leadership role. [18:48] And, you know, to come back to this sort of sense of like, what got me here is not going to get me there. [18:53] and and sometimes you know i work with a lot of leaders and sometimes that's come with like a pretty significant cost right this this this juxtaposition you know maybe your happiness your health your marriage there's [19:04] there's been this sort of existential crisis of [19:07] I don't know if I love this anymore. Maybe it leads to burnout. [19:10] Maybe it's not even that dire. It's just a sense of like, well, I'm looking around and I need to [19:14] be something i need to unlock something else to continue on this on this path. [19:20] And and there is a sense of sort of stuckness that comes from that. [19:26] And. [19:27] What I've come to realize is this is a [19:29] the precipice of it. I think this is a pretty fundamental concept. [19:32] in [19:33] in leadership. [19:35] And I'm not the, you know, I'm not the originator of this. So this has come up again and again and again. [19:40] It's not new. It's going to sound familiar. It's not even it's like the [19:45] The flood myth. [19:46] from Gilgamesh showing up and, you know, all this sort of oral histories of the world, right? It's not new. [19:51] Um, [19:52] Conscious Leadership Group. [19:54] organization that I'm a big fan of. They call it above the line versus below the line. [20:00] Brene Brown calls it daring versus armored leadership. [20:04] Sage versus warrior. [20:07] even in the world of sports, there's like [20:09] playing to win versus playing not to lose is sort of this concept that's come up again and again.

[20:14] And Leadership Circle calls it creative versus reactive. And that's the term I'm going to use. I like that. [20:19] And here's the distinction. [20:22] Very simple. [20:24] Are you responding correctly? [20:25] to the world from a place of fear. [20:28] where you see problems and threats. [20:30] You want to be right. You want to be liked. Your defensive is sort of in inward direction. [20:35] approach. [20:36] or [20:38] Are you... [20:39] responding to the world from a place of openness, [20:42] possibility, curiosity, passion, growth, purpose, right? [20:47] Very simple concept. [20:49] Pretty much everyone understands what I mean. [20:52] Right? Makes sense. [20:55] Everyone also then immediately says, [20:58] We have a couple different things. [21:00] That sounds amazing. [21:01] I'd rather I'd rather have that. [21:03] We're here in moments when I felt that. [21:06] But that's usually followed up by a couple of questions. [21:09] I don't, [21:10] Know if that works. [21:12] It doesn't sound very effective. [21:14] Is it possible? You know, is it is it is it possible? [21:17] And then how do you do that? [21:20] And. [21:23] the effective part is is as actually a question we can answer which is yes it is it is more effective [21:28] Um, [21:29] who's uh bob anderson bill adams are two management scientists um who've who've written extensively done a whole bunch of research and [21:37] Um, [21:38] They have looked at every possible dimension you can imagine of success, both leadership

[21:44] capability they've looked at you know revenue brand you know profitability everything and it's shown yes [21:51] this creative form of leadership is in every possible way [21:55] positively correlated with success. [21:57] and reactive leadership is is negatively correlated so yes it works [22:02] Um, [22:03] Yet, [22:05] According to their research, some 70, 75 percent of leaders are primarily operating reactively. [22:12] So most leaders. [22:14] are operating from a place of [22:17] Fear. [22:18] reacting, seeing problems and threats. [22:21] and [22:22] That's because that other question of how do you do it is such a hard one. [22:25] to answer. [22:26] And it's not an easy thing that you can kind of flip a switch of. And it sort of goes back to [22:31] this notion of like redesigning that internal operating system. [22:35] or how you confront the world [22:38] How you? [22:39] what underlying belief systems and assumptions you have that are causing you to operate from that place. Can I ask you a quick question? [22:45] Just to clarify the two sides. [22:47] what's kind of a sign that you're in the reactive side of things? I think one thing you said is, [22:53] you're worrying a lot about how people think about you and make sure that they like user anything else that's like [22:58] going to tell a listener like, oh, maybe I'm falling into this trap. [23:03] Yeah, the... [23:04] You've nailed it, which is that [23:06] Fear. [23:07] Like operating from a place of anxiety, right? [23:11] There are different ways. [23:13] ways depending on our mindsets, our approaches. I like the word postures because it seems to

[23:19] to click. [23:20] different sort of ways that we retreat into this, [23:23] Reactive mode. [23:24] Um, [23:25] Fear, anxiety is the way, right? It's sort of like, that's how you know. You're just like, oh, I'm bullying. I'm below the line. I'm just like, I'm seeing problems. I'm seeing threats. [23:34] Um, [23:35] our brains are hardwired to do that, right? So it's not like, [23:39] That's wrong. [23:40] These are brains that that learn to do that. [23:44] you know, I don't know, on the tundra, like being chased by wild animals, right? So this is our normal way of being. [23:54] There might be different [23:56] desires and needs that force you [23:59] to operate that way. [24:01] We think of there's really sort of three of these postures and [24:06] Anybody is probably more than one of them. So this is not pathologizing. This isn't putting you in a box, but one, probably one of these will resonate more than the others. [24:15] wanting to... [24:16] to be approved, wanting to be loved, wanting other people to like you. [24:20] This was me in my early part of my career. [24:23] Same. [24:24] Yeah. So this is, you know, you kind of like heart type, right? It's sort of what's sometimes called move toward other people. [24:30] Um, [24:30] A lot of that came from my environment, right? I was coming up with product management. No one necessarily knew what the job even was. And I had no authority. And most people could just ignore me if they wanted to. [24:40] And so I sort of had to meet other people's expectations, please them, want to be accepted by them. [24:46] seek their approval. [24:47] And it was [24:49] sort of this, what we call a complying system,

[24:51] approach. [24:52] and [24:53] Here, this is why this is so vexing is it actually worked really well. Right. It was pretty effective. Other people liked working with me. I listened to them and I sort of considered everyone's needs and. [25:04] and made sure everyone felt heard. [25:07] But there came a point where I started, like, I gave away so much power that, [25:12] you know, it was it was hurting me when it comes to purpose and execution and decisiveness. [25:17] And so, again, these aren't these aren't bad. There's usually underlying tendencies that are very good. It just starts to have a cost as you as you become more senior. [25:25] It's like the gears start to kind of grind to a halt a little bit. [25:29] Um, [25:30] Another way is a more of a, [25:33] needing to be right sort of head type. [25:36] protecting one's own ideas. [25:39] Sometimes called a move away from type distance, arrogance, criticism, sort of retreating into your own ideas and head. [25:48] And then the other is [25:50] you know, we'll, [25:51] will not be a surprise is the more controlling, [25:54] My way or the highway, autocratic, will, move against, wanting to win, wanting to be number one, wanting to excel, wanting dominance, wanting control. This would be another tendency. [26:06] Um, [26:07] Often one of those [26:09] feels natural to you and another one feels [26:12] just so incredibly distasteful that you can't imagine. [26:16] possibly operating that way. [26:18] And this goes into sort of the underlying beliefs part.

[26:22] You'd asked, you know, if you had told me early in my career when you saw me, [26:27] being passive and people pleasing like that. [26:30] You just got to stop caring what other people think, Ken. [26:34] You got to start being, you know, you got to be more. [26:37] Pushy. [26:39] Um, people did say that to me. That was pretty common, probably in my, my performance reviews, pretty common. You know, even people worked for me were like, you need to push back. [26:48] My only archetype for doing that was the autocratic controlling type. [26:53] I was like, I don't want to be like that. [26:55] That guy's a jerk. [26:58] He's that's a that's a fascist. I don't want to be a fascist. I do care about other people. [27:02] And so many of our [27:04] our examples and archetypes are these sort of equally ineffective reactive ways of being and so no wonder i didn't want to be like that because that's also not very effective either [27:13] Yeah. [27:14] But there was a sense for me of redefining [27:18] you know, this is where coaching is powerful is this, [27:21] What are the underlying assumptions and beliefs that you have? [27:25] that are causing you [27:27] to fall back on [27:29] some of these fundamental [27:30] ways of operating. [27:32] and not let go of them, right? Because the answer for me wasn't, [27:35] Stop caring about other people. [27:38] I wasn't going to do that. That's a value of mine. It's part of who I am. [27:41] But take the [27:43] caring about other people, the empathy, the connection and direct it in a more [27:47] creative way where you're operating now from a place of purpose and vision and not reacting and protecting and defending and wanting to be

[27:54] Yeah, light. [27:55] For me, the key to that was [27:58] letting go of [28:00] needing to be liked. [28:02] in redefining [28:04] it as [28:06] as. [28:07] admiration that takes place over time. So rather than [28:11] I want to leave this room with everyone liking me. [28:14] I started to realize I want to be the type of leader where, [28:18] A decade later, people say, [28:20] I would work with that guy again in a heartbeat. [28:23] And that was part of the unlock for me. Again, I care about other people. That's a natural sort of gift that underlines it, but it's a redefinition of, [28:31] how that serves me. [28:33] If that makes sense. [28:34] Say someone's in that first bucket, and I was definitely in that first bucket, and I still want people to like me. I still probably have flaws there. [28:44] But say RPM and you're like, oh, man, that's exactly how I am acting right now. [28:49] It sounds like, is the core of it just like a mindset shift going from [28:53] I need people to like me to what you just talked about of like, OK, I'm going to shift to [28:57] I just want them to respect me over time. And is that kind of the core of it? I know it's probably not that easy, but how should someone... [29:03] behave if they're in that bucket right now. [29:05] Yeah, it's not it sounds easy. Right. And this is part of what is hard about this is it always sounds easy when you describe it having gone through the journey. Right. Sort of like, you know. [29:14] You know, talk to somebody on the summit of Mount Everest and they'll be like, yeah, you know, I just climbed this mountain. That's how I got here. And you're like, OK, wait, that's not that easy. [29:22] And again, it is very individualized.

[29:25] I think there's an appreciation [29:28] that [29:30] You have to understand what is... [29:32] What is holding you back? [29:34] and [29:35] this is a lot of the work that i'll do with my clients is what is the sort of underlying expectations [29:41] What are these underlying beliefs? [29:43] Um, [29:44] I... [29:45] believed that my style was incompatible with being a leader. [29:50] Right. I would have said I can't be a CEO because, you know, I'm not tough enough. Right. I'm not [29:57] I'm not strong enough. I'm not commanding enough. I can't command a room. [30:02] And it's like, okay, what [30:03] What is the... [30:05] underlying belief I'm making about what leadership is there. [30:09] There's an archetype that I have in my mind that is incompatible with this this way. [30:14] And so there's a need to confront that. OK, what makes you believe the only type of leader is the leader that can that orders people around? [30:22] Maybe that's all I've ever seen. [30:23] Um, maybe I don't believe it's possible to be any other type of leader. [30:28] Um, [30:29] Maybe there's an inner critic that is like convincing me that that's not who I am. [30:33] as a part of it is a sort of redefinition of what does leadership mean for you, for you authentically? What would it be like in my case? [30:41] to lead with purpose and be decisive and lead with vision. [30:44] and to have other people felt like they're being brought along and listened to and participated and create safe spaces for other people to [30:51] Like that was the sort of question there. [30:53] And it took people challenging my point of view, working with a coach, asking me questions,

[30:59] forcing me to see places I'd made connections that the connections don't really need to be made [31:04] Um, [31:05] There's a lot of instruments and tools we work with in coaching. There's 360 degree [31:09] assessments that are very helpful here that will start to help you understand, hey, here are places where you're operating reactively, here are places where you're operating really create creatively. [31:18] Um, because by the way, most people are, [31:20] you know, [31:21] partially somewhere in that journey. It's a developmental process. [31:25] and to start to be able to get the [31:28] The feedback. [31:30] The dopamine hit of seeing... [31:32] when I do it this way, it actually it's more effective and it doesn't cost me as much and I'm happier and I'm enjoying it. I'm seeing that it's working. [31:40] is oftentimes a big part of this because there is this disbelief that it won't work. [31:45] The number of times when I'm with a client and coaching and say, well, what if you what if you did do that? [31:51] And they go, it just won't work. [31:53] you realize that there is this sort of [31:55] This this wiring in there that needs to be. This is what I talk about this sort of operating system. It needs to be rejiggered. [32:01] to start to make sense of what if it did. [32:03] And how might you know? [32:05] The point you just made about how... [32:09] you can realize that you can be successful in a lot of different ways [32:12] And you don't have to be this one archetype of a leader. Really resonates with my experience. I actually had an executive coach for a few months. [32:20] And that was probably the biggest unlock for me. [32:22] We did the strength exercise. [32:24] which a lot of people do, [32:26] And the main thing that she helped me see is like, [32:29] You can do all the things.

[32:30] that you want to do through the lens of the strengths that you have and not have to force yourself to be good at these other things because there's many ways to accomplish the same outcomes. [32:40] That's exactly right. And then [32:43] Once you start to understand that, you start to develop a better way of finding the right place, the right environment, the right role. [32:52] Um, [32:52] you know, when we talk [32:54] began the conversation and you asked me what brought me into executive coaching [32:58] I would feel these [32:59] these sort of I would I would describe it as flying too close to the sun in my career, right? Where [33:04] I would I would have a team. I'd be managing a small team. I would love it. I would enjoy it. And then suddenly my team would grow. I'd become more senior than I felt comfortable being. And then I felt like I wasn't getting to do the quote unquote real work anymore. [33:17] And then I would. [33:18] We did... [33:19] just completely disheveled and dissatisfied. And then I'd go, [33:22] try to go find a smaller team or even stop being a manager. [33:26] And and it was a very meandering, reactive path. It was like I was eventually every so often I was catching a wave and I knew what it felt like to be on the wave, but I didn't know what the characteristics of the wave were. [33:37] And then through coaching, I was like, [33:39] I love connecting with other people. I like helping people grow. I like helping challenge people. I like helping, right? [33:46] And then and then it was like, what are those parts? What if I unpack those? Oh, that's why I loved managing that team of five, because I got to do a lot of it. [33:54] That's why I hated managing a team of 35 because there's no time for it. [33:58] And then you start to say, okay, what if rather than

[34:00] you know, [34:01] just randomly meandering through my career, I actually elevated [34:06] needing to connect wanting to be helpful you know and then you're like what would it be like if i went into the helping professions right it's [34:13] It's just a reframing of [34:15] you know, [34:16] move [34:17] through your career in a way that seems externally to fit some definition of success and to start to define that internally. [34:25] right and that is the very definition of the reactive versus creative mindset reactive [34:29] allowing the world to set the expectations and try to meet them. [34:35] versus tap into what your real... [34:37] true sense of purpose and vision is. [34:40] and then use that to [34:42] Navigate the world. [34:43] It's interesting that so much of this is just mindset. It's not like learning a new skill as a leader or product manager. It's like, [34:49] just seeing yourself in the world differently and all of a sudden you kind of unlock [34:53] your career is that is that what you find [34:56] Absolutely. And that's why [34:59] you know, I think so much of the focus on the skills, uh, [35:03] the frameworks, you know, it can be limited as you as you develop these. [35:08] these capabilities because it's inner work, right? We're talking, where we're talking about is this is, this is all me. [35:13] Um, [35:14] Now that's empowering. [35:16] There's empowerment to be able to say, [35:20] you know, I want to change something and it doesn't involve a whole bunch of other people convincing and persuading them. [35:25] you know, getting into an executive, it's all me, but it also in some ways makes it harder because,

[35:31] Because it is all you. And this is, you know, in coaching, [35:35] It's all about you. It's all about that. Who am I? [35:38] What matters to me? [35:40] what underlying belief systems [35:43] inner voices or [35:45] or challenging me in ways that I want to be challenged. What is my unique? Um, often, I mean, I love the word authenticity. It's like, you were just talking about like, [35:52] What is my authentic way to lead? [35:55] And then how do I center that? [35:57] rather than trying to fit into someone else's definition of [36:00] what leadership might be. And you may recognize, I can't be that authentic way of leadership. [36:06] leader at this place or in this place type of company. [36:10] But I know [36:11] how to find it and I'm going to go find it. [36:13] Do you have any more examples of either someone kind of uncovering this about themselves? [36:19] or another mindset shift that you can make in one of these other buckets, similar to kind of the idea of I'll think about people liking me over the long term versus immediately. [36:30] yeah you know it it really does vary you you start to pick up on that shift when it [36:36] It's less of. [36:38] Um, [36:39] How [36:40] you know the the goals being defined externally and more more of the goals being defined internally right so [36:46] You'll have a conversation with somebody who's new to coaching and you'll say, what do you want? [36:51] And they'll be like, well, I want to get promoted to VP. [36:55] Okay. [36:56] Why? [36:58] Because I want to because I want to be a VP. Right. It's like, well, what's important about being VP? Well, because eventually the answer is, well, because it's there. Right. And that's the thing that I'm supposed to do.

[37:09] And then you start to notice the shift and it starts to become more of, [37:13] you know, [37:13] Well, because really what I love is, you know, what's important to me is creativity. [37:18] And, you know, when I when I want I want more creativity in my life, I want more. [37:24] you know [37:26] ability to challenge other people. Right. And so you start to kind of dissent this a little more from in than from out. And that's where that shift is in. [37:34] The journey is different for it. [37:36] for everyone um [37:39] And I think ultimately this is part of why, quite frankly, coaching may not be right for everyone. Right. It may be. [37:45] If we go back to that video game analogy, [37:48] you're looking for someone to just [37:50] teach you the tutorial so you can learn how to play the video game and there's you know [37:54] this jackass like me sitting next to you and saying, [37:57] what's important to you about playing this video game you're gonna be like just how can you tell me how to hold the controller can you stop [38:03] So it's not always right. It's a place where [38:06] I think oftentimes people recognize that [38:09] And they've gotten all the advice, all the frameworks, all the rules, all the tricks, all the tips. They've learned that. They've mastered it. They've tweaked it. They've optimized it. They've recognized the shortcomings. They've customized it. [38:20] And [38:21] the emergence that's required for them to get to the next level is just going to come just as much from inside them as it is from outside, if not more. [38:29] And that's that's when that ship is made. And that's called mentorship, right? I think for people that are just looking for actual concrete advice on how to do a thing. [38:37] Is that right? [38:38] versus coaching. I think so. And, you know, this is where the words are squishy because I, there are a lot of people who are mentoring who are also stepping into a coach role occasionally.

[38:47] You know, there are plenty of [38:49] you know managers who are great at coaching you know as necessary so it sort of skills run the [38:57] How much are you looking for... [38:59] So I'm going to tell you the right way. [39:02] versus how much do you believe that there even is no right way? It's ultimately going to have to be your way. [39:08] And that's a different place, a different point in your career, different levels of journey. It's part of why I tend to work with probably more senior... [39:15] Executives. [39:16] um because they don't they're not looking to me to tell them how to do the job they've already learned how to do the job it's just something deeper that's going to need to break through from that this episode is brought to you by unit what did gusto uber shopify and angel list all have in common they've all decided to build banking into their product according to angelist head of product banking makes every single feature more interesting with it our platform functions as financial [39:46] big messy stack. Embedding banking into your product not only adds differentiation, but also helps you acquire, retain and monetize your customers. UNIT is the market leader in banking as a service, combining multiple bank partners with a developer-friendly API to empower companies of all sizes to launch accounts, cards, payments, and lending in just a few weeks. UNIT is trusted by a leading brand such as AngelList, HighBeam, Invoice2Go, and Roofstock. [40:14] To hear more about how Unit enables companies like yours to build banking, visit unit.co/lenny to request a demo or to try their free sandbox.

[40:24] That's unit.co slash Lenny. [40:27] For someone that wants to do this sort of work, but [40:30] can't find a coach, can't afford a coach, [40:33] Is there something people can do on their own that you'd recommend to help them kind of shift their mindset and do a lot of these things that you've been describing? [40:42] Yeah, it's a great question. I think [40:44] here's the secret about [40:48] the coaching industry, [40:50] Anyone can call themselves a coach. Like there's no, it's, it's very democratized. It's great. Like there's no. [40:56] gatekeepers and barriers and there's no like 500 licenses you have to go through [41:01] and there are [41:03] tons of great coaches who [41:06] are at various different price levels, at different levels of accessibility. [41:10] And so, you know, I would if you say I can't afford a coach, I might sort of challenge that a little bit and say, you know, have you looked? [41:18] Um, the other thing is that you don't need a coach who's done the job before. [41:23] And... [41:24] And that's another, I mean, obviously I've done the job before, so I'm sort of undermining part of my own selling point here, but, [41:29] Um, [41:30] coaches are trained to coach people on any topic so when i go through coach training i can i can coach you on anything people can coach you on anything and sometimes even there might be power in having a coach that's never done the product management job because there won't be any [41:42] any sort of [41:43] Um, [41:44] cheating of like starting to kind of move into a more of advisor role or maybe as the [41:48] coach either [41:50] There may be no, well, you tell me what I should do. And the person will be like, I don't know. I've never done this job. Let's go back to what you want.

[41:55] So there could be some benefit from that. And again, you don't have to have done that. [42:00] So I would say coaching is is incredibly powerful. I wish I'd had a coach much, much earlier in my career. [42:06] And so, you know, the answer, maybe coaching is more accessible than you thought. [42:11] Um, [42:12] If not, I think [42:13] you know, the [42:16] The things that we're talking about here are [42:19] internal understanding of what matters to you [42:23] your sense of purpose. [42:24] this sort of inner curiosity. [42:27] Um, and, and that can be harnessed at any age. So just sort of wondering about yourself at any point in your career, like wondering what's important to you. [42:34] you know i love doing values work like what are your values like okay now what do you really are your values right like that's something you can do yourself that's something you can kind of question you can read about you can start to understand [42:45] Um, [42:46] Mentors can be great, especially mentors who are [42:49] less about trying to tell you the right way and get you to follow directly their path, but are more their sort of [42:54] applying some curiosity, asking questions, challenging you in certain ways. [42:59] being a way that you can bounce ideas off of [43:02] Um, [43:03] Great managers, I think, especially the best product [43:06] leaders, [43:08] understand how to put the coach hat on and when it's appropriate to put the coach hat on. [43:13] and are explicit about that or sort of like, okay, let me [43:16] Let me take off my manager hat now and put the coach hat on. [43:19] you know what do you what do you really want to do let me like what's important to you what's your career [43:24] And so I think you can get coaching for every work.

[43:26] Um, there's a lot of self coaching you can do. Um, there's a lot of, this is honestly, one of the benefits for me having gone through tons of training and coaching is like starting to coach myself, like being like feeling an emotion and asking myself coach questions. [43:39] really powerful. That's something you can learn. You can do when you've had a coach, you can do it when you don't have a coach. [43:44] You can explore it. So, [43:46] I think this is really all about really being curious [43:49] and wanting to understand who you really are. [43:51] at the core and what's important to you and what matters. And that's something that can be done, you know, with or without a coach. Are there any resources that you love for either the values work [44:01] or kind of learning these questions to ask yourself. We can put them in the show notes if nothing comes to mind immediately, but [44:05] Is there something you recommend people check out? [44:08] Um, [44:09] Yeah, there's some great books. [44:11] Maybe I'll use this opportunity to throw out a couple of suggestions. I guess we can link them in the show notes. [44:17] Um, [44:18] Brene Brown's Dare to Lead. It's a good book. And she actually even has a whole section in there around values, sort of confronting your values. I like her approach. There's some free resources on her website. [44:28] Um, [44:29] I love... [44:31] conscious leadership groups work here. The 15 Commitments of Conscious Leadership book is fantastic. There's a [44:39] And you don't even need to [44:40] to buy the book. There's a ton of stuff on their website, Jim Detmer. [44:44] um, Diana Chapman and, um, [44:47] Kaylee Warner-Klemp are the authors of that book. [44:51] And that's all about a lot of the stuff we've been talking about. And they're the ones that have the sort of above the line versus below the line that fits into the sort of creative versus reactive approach.

[45:01] standpoint. [45:03] Um, [45:04] Those are all fantastic. [45:06] If you want to go deeper into more of the. [45:09] the management science behind it, if you're like me and really curious about [45:13] the psychology and the management science. Bob Anderson and Bill Adams' book, Mastering Leadership, [45:20] creates the sort of, um, [45:22] the entire sort of system, integrated system around [45:26] creative versus reactive. [45:28] And sort of as a teaser, [45:31] They identify five levels of leadership of which reactive is the second, creative is the third. [45:37] So beyond that, you get into Integral and Unitive. So if you're looking to unlock the advanced stages beyond Creative, [45:46] There's a lot of great stuff in there. And that's where all the research comes in as well. [45:50] Um, [45:51] from an adult development standpoint, [45:53] Robert Keegan is sort of the godfather of the adult stage development work and the sort of meaning making that underlines a lot of this. [46:02] He has a great book called Immunity to Change, if you're curious about that. [46:06] Awesome. We will link to all those in the [46:08] description of this podcast so folks don't have to google around i have a couple more coaching questions [46:14] before we move on to a few other topics. [46:17] Um... [46:18] One is just what are you finding are the most common blind spots for product people in general? Like how are how are people shooting themselves in the foot most? [46:28] Oh, that's a great question. [46:30] You know, I think...

[46:34] probably the number one [46:37] category, I'm not sure it's a necessary problem, but maybe category of problems is [46:42] you know and this is i think great lesson for people earlier in their career [46:46] is [46:48] How much... [46:50] All of the challenges that senior executives are dealing with come down to people. [46:55] versus product. So it's fun to think about designing products, optimizing, doing [47:02] user discovery and you know what testing what but it's like you sit down with an executive and it's all about people right that's the hard part it's about persuading people getting groups of people don't want to work together [47:15] trying to figure out how to deal with difficult personalities, figuring out how to [47:19] set a vision and articulate a vision and create an environment where people can collaborate and play [47:24] Um, [47:25] And so I think there's [47:27] you know, the sort of category of blind spot often is, [47:31] people being confronted with that. [47:33] without having been intentional about thinking of it as a skill or an area that they needed to work on, needed to improve. [47:41] Um, [47:41] And... [47:42] Part of what I think is pretty exciting... [47:45] about product [47:47] Product management is. [47:50] You are a leader from day one. [47:52] in product management. [47:54] Right. And, and, you know, [47:56] There's leadership all over the place, but that's sort of your job. You're a leader. You don't have... [48:00] any formal authority. [48:02] But you're a leader. You're expected to lead.

[48:05] And guess what? The hardest part about being a leader is when when you don't get to just rely on the formal authority. So you're getting to practice all the hard parts about leadership from day one. [48:14] Um, [48:15] Because you're nobody's boss, right? [48:17] And you get to... [48:19] to [48:20] you know, sharpen those skills, develop those intuitions, get better and better at that so that when you do someday, if this is right for you, become someone else's boss. [48:29] You've already been able to lean into that. [48:31] And so [48:32] the people side of this is... [48:34] is [48:35] He's such an incredible... [48:38] aspect of what product management is. [48:40] And what I find, you know, and this may be a sort of a category of blind spots is people realizing that. [48:46] when they're put in a position where they're expected to, [48:49] to have impact and realizing that, [48:53] They haven't developed the skills. They haven't developed the capability to actually be able to [48:59] to manage and work through all these people. [49:01] How do you actually get better at that or develop those skills? I know it's maybe too big a question, but what can people do to... [49:08] realize like now that they know this is maybe a big blind spot what should they do [49:13] yeah i just think of recognizing it's part of the job it's important and and you know this is maybe i came up at a certain time where [49:20] is often dismissed as soft skills, right? It's just like, you know, soft skills are helpful, but like they're not actually something you want to work on. [49:28] something you train, not something you [49:31] And, you know, [49:33] This is just as important, right? This is the equal, you know, I wrote a piece recently about

[49:38] the art versus the science the art is communication collaboration the more sort of fuzzy softer skills people stuff [49:45] And it's an elevation of that being just as important, if not more important over time, as all the sort of skills, techniques, tactics, you know. [49:54] managing a backlog, all that kind of stuff that you have to do. [49:57] And, [49:58] you should invest in that the same way you invest in those other skills so if you [50:02] You go off to a training place. [50:05] Um... [50:06] to learn a technique for doing, you know, [50:11] I don't know, some sort of technical... [50:13] dashboard analysis. [50:16] Um, why don't you go to training to learn how to have difficult conversations? [50:21] Um, cause there's some great training about there about having difficult conversations. [50:25] or do some training about storytelling. [50:28] These are all really, really important factors that start to come into play. [50:33] And, [50:34] What I would recommend is just appreciating that these are going to really, really matter and practicing and valuing them and not thinking of them as something that either will matter later or a distraction or not really. [50:45] part of the job. [50:47] I think the reason people don't do that work is because it's so hard. [50:51] It's difficult conversations are difficult. [50:54] And we talked about this with Shreyos, but just like... [50:58] It's like a rule of thumb. The thing that is hard is probably the thing you should be doing. [51:02] It's like a compass pointing you to the thing you should do. Absolutely. And that is, you know, we are all about doing hard stuff, product managers. That's what we're all about, right? And so, you know, when something seems...

[51:14] hard and it seems squishy and it seems like it's difficult to put a three-step rule around or [51:20] chances are it's really going to matter. And it kind of goes back to this, [51:25] this mindset shift, right? [51:27] That means that [51:28] this an opportunity for you to, [51:31] you know, to readjust your inner energy [51:34] complexity management system to adapt to that area of complexity that you're now seeing. [51:40] because this stuff really feels squishy right [51:43] And so that's even more of a reason why you want to get your hands around it and grab onto it and value it and learn and grow from it. [51:50] Speaking of difficult and squishy, [51:52] I'm guessing that one of the biggest challenges that people you work with face and one of those recurring themes is imposter syndrome, people having imposter syndrome. [52:01] something definitely I went through and it comes up a lot on this podcast. [52:04] What do you really advise your clients to do when they're feeling imposter syndrome? [52:11] Yeah, it's a great... [52:12] question. Um, [52:15] I always get corrected to say imposter phenomenon by people in the psychology community because I guess it's not a dysfunction. I don't. So I've learned to to use their terms, but. [52:25] Um, [52:25] Yeah, everyone... [52:27] I think just about everyone experiences at some point. Research shows that that definitely is borne out. [52:33] Um, [52:35] You know, it's it's really a moments when you're doubting your abilities or you feel like a fraud, you feel like you don't belong. [52:40] it's funny as I'm [52:43] interrogating my own inner

[52:46] emotional state right now. I'm feeling a little bit because you're asking, I'm like, [52:50] There's a part of me right now, it's just like, you're not a trained psychologist. What are you? [52:53] When I said that whole thing, well, it's technically a phenomenon. [52:57] There was a voice that was like, what are you talking about? You don't know what you're talking about. We'll put a disclaimer on this. On the episode. Yeah, I'm not a psychologist. [53:04] So, look, we all feel it. And, you know, there's a part of me right now is like, I'm going to say the wrong thing and embarrass myself. [53:09] I think your point around squishy, exactly right. Like product managers, product leaders, maybe more so because the role is so cross-functional. [53:17] and ill-defined and there's always going to be an edge of [53:20] the job that you aren't as qualified as whoever you're interacting with. It's sort of the nature of it. Like we're never going to be as good an engineer, as good a designer, as good, you know, so there's all these sort of opportunities for that. [53:29] And I find... [53:31] Certainly from client work that [53:33] There is a little bit of a softening and solidarity just knowing that. [53:36] And I just like, oh, you have that too? I have that. Yeah, there's some value to that. [53:41] Um, [53:42] I do think, though, it's probably worth... [53:46] I think it's important to pause here and say that there is the risk of [53:52] dismissing or even maybe weaponizing [53:55] imposter phenomenon against [53:58] particular population, particularly women, [54:01] people of color [54:03] of all genders, women of color, especially right. [54:06] who are facing real problems. [54:08] external feedback and doubt about their abilities, right? The environment is reinforcing and sort of the source of a lot of this stuff, microaggressions, bias, real regressions.

[54:18] And so I think we always have to be careful in the helping professions to not [54:22] dismiss it as a problem that just shifts the obligation to the person. So it's like, oh, that's just your imposter syndrome. Deal with it. [54:31] Well, it's really easy to overlook all these sort of systemic issues that are leading to that imposter syndrome. [54:35] So leaders I work with, I think we have a special obligation. [54:39] both to sort of confront our own [54:42] inner inner dynamic but also to recognize what our role is in the environment the broader environment um that might be contributing to some of this stuff and if you're a leader you're [54:50] you know, you have a special obligation to [54:52] dismantle those, not [54:55] when you're meeting with your people, be like, ah, it's just your imposter syndrome. You can work through it, hire a coach, but to recognize, okay, wait, what signals are you getting? What, what issues are contributing to this? What's our role in, [55:05] needing to change that. [55:07] Um, [55:08] So I think that's worth it. [55:10] worth pointing out. [55:11] There's [55:13] There's, oh, and by the way, there's a great article in Harvard Business Review from a couple of years ago. [55:19] I think it was title was literally stop telling women they have imposter syndrome. And the two authors of that were. [55:25] Ruchika Tulsian and Jodianne Beery. [55:28] But if you're curious, you want to go into more depth on that. [55:31] As coaches, there's all sorts of ways we're trained to work with this. [55:35] oftentimes as an inner critic and inner voice, we all have voices, saboteurs. They're often trying to help us. They have good intentions, but they're, [55:44] They're sort of developed to try to protect us in certain ways. [55:48] So gaining awareness of those, right? Just sort of like, oh, that is an inner critic. That's what it's trying to do.

[55:54] there's a self-distancing that's valuable to that and sort of really kind of [55:58] I like to think of it a little bit as you got a border, you got inter-border directors. [56:02] And [56:03] There's some, you know, noisy, chatty, [56:05] voices that every so often sort of sit in the chairman's chairperson's seat. [56:09] and start taking over and if you start to recognize wait no i'm the chairperson [56:14] I don't want to hear from you right now. We'll hear from you later. It starts to create some power and you start to notice when it's happening. [56:19] Um, [56:21] you know, [56:22] We will bypass inner critic sometimes as a classic coaching technique. It's like, okay, I'm sounding like that's your... [56:30] you know critically saying that what if we just ask it to maybe step aside let's keep talking here [56:34] You can befriend it. There's a lot of [56:37] practices and works. It's actually trying to understand what its motivations are. If you think of it as a board, you know, [56:43] Give this board member a new job, put it on a new committee, reassign it. [56:48] Um, [56:49] There's oftentimes underlying belief systems. You know, we talked before about my impression of what a real leader was and sort of who they had to be. [56:57] And so, hey, when all those [56:59] Second guessing of me not being a real leader, me not being qualified came from some of those underlying assumptions that that was the only type of leader that was effective was somebody that was like slamming their fist down on the table. [57:09] Okay, so what if we redefine that? [57:13] Right? [57:14] I'm too kind to be a leader. I'm not dominating and commanding enough. [57:18] When you hear a client say that as a coach, you recognize there's a connection being made here. [57:23] between what effective leadership is and isn't. Let's interrogate that connection. Is that connection actually true?

[57:29] Um, [57:30] you know, the [57:32] The [57:34] you know, again, sort of get back to this question of, [57:38] you're often responding to other styles, approaches you've seen, you're comparing yourself to others, right? So this is the reactive mindset of, [57:45] I'm always comparing myself to that person, that way, that being. [57:49] and seeing myself as lesser than. And so the inner work of sort of starting to see who I really am truly inside and less comparing myself to others. [57:56] But yeah, imposter phenomenon syndrome, whatever you want to call it, very, very [58:01] Very common and very... [58:03] very popular i suppose other than i say popular it's like popular like a play [58:08] Another inner critic tactic I've heard that I kind of used for a bit that was helpful is to give your inner critic a name. [58:15] Like Jim. [58:16] And you'd be like, Jim, not right now. I don't need you right now. [58:19] Yeah, that kind of helps. [58:21] Yeah, there is a whole school of... [58:23] coaching that that I've worked with that it's called parts work or internal family systems it comes from a [58:31] psychologist named Richard Schwartz who determined this. And it can be really, really powerful. Like I'll work with my clients. We will... [58:37] We will give them names. We will imagine what they look like. They will interview these parts. [58:42] Have you seen the Pixar movie Inside Out? This notion that like, hey, all these different parts show up in different ways. [58:49] And I'm going to put myself, you know, the real me, the real self, [58:53] into the chairperson's seat. [58:56] And when I hear these voices, I'm going to appreciate it. [58:58] them for what they are and who they are.

[59:00] They're not me. They're parts of me. [59:02] And there's something really powerful in that, right? There's a sense of like, [59:06] Because otherwise they're all me. So I just hear this voice telling me I'm an idiot and I'm a clown and I'm not qualified to be in this room. [59:14] and then when you can start to go oh yeah there there it is that's [59:18] You know, that's Larry the loser. [59:20] Right. [59:21] big, you know, angry, irritating judge who's, of course, well, yeah, you know, Larry always shows up every time I do something new. [59:29] Because Larry doesn't want me to challenge myself. So of course Larry's going to pipe in. I've heard from Larry. [59:34] I'm going to ask Larry to step aside. Let's go. [59:36] Yeah. [59:37] It can be very powerful. [59:39] I love that. One last question about coaching for folks that want to find a coach. [59:45] Do you have any advice of just like how to find a coach? And then what questions can you, what are like a couple of questions you can ask to evaluate if they're a good fit for you? Yeah, great question. So. [59:54] I think like any helping profession, you know, like finding a therapist or really anyone who you're going to have a. [1:00:00] a deep and sort of lasting... [1:00:02] relationship with the sort of trust and authenticity is really important. And I think we all, all us coaches recognize, and we feel this as well with clients, is it either has to be a fit or not. [1:00:14] And sometimes it's hard to put your finger on it. Sometimes you just... [1:00:17] You meet with someone and you're like, yeah, it clicks. It feels right. Sometimes you're like, yeah, it doesn't. And that's okay. [1:00:23] And so all coaches worth their salt will offer a free session to, to, to try to understand that, engage that. And,

[1:00:30] And I always tell [1:00:32] everyone in that session. [1:00:34] you know if if you don't decide to work with me or i just we don't need a reason right it's fine it's just not a fit [1:00:40] And that's OK. You don't need to come up with a bullet point reasons to let me down. Just it's part of how it goes. [1:00:46] Um, [1:00:47] you might prefer certain... [1:00:50] People of certain genders, certain backgrounds, you may feel more comfortable with, less comfortable with. Maybe you want an old guy like me. Maybe you don't want an old guy like me. [1:00:57] And it's fine. It sort of has to feel right. [1:01:00] I would ask them to talk to you about [1:01:04] what coaching is to them. [1:01:06] Because, again, it might combine some of these more mentory things. It might be more tactical. [1:01:11] Some coaches are more sort of structured and we're going to, [1:01:15] Week one, we're going to do this. Week two, we're going to do this. Week others are more [1:01:18] Sure, pure coaches like me were, you know, look, you know, within the first five minutes, I'm going to ask you what I want to talk about today. [1:01:24] because you're breaking the agenda. [1:01:25] So figure that out, figure out what works for you. [1:01:28] And then I think... [1:01:30] There's a lot of great places to go, actually, specifically like where to go. The International Coaching Federation is our governing body. So those of us that are credentialed coaches, you'll find there. Again, you don't have to be credentialed, but that'll be a great place to find people who are. There are some matchmaking services, BetterUp, Torch are some of the more accessible ones. There's one called Prismatico. It's a little bit more higher end for more senior execs. Scale just put out a list of top coaches who work with product managers and product leaders, [1:02:00] glue that link.

[1:02:01] Lenny, I think you're involved. [1:02:04] Yeah, congrats on winning one of their categories for best coach of which category was that? [1:02:10] product leaders. So this is just a setup for you to say that. Thank you. But there's tons of great coaches and different styles, different stages of careers. [1:02:20] And I think all those folks have have work work with or have worked with product product folks. And so [1:02:25] You know, again... [1:02:27] just talk to a few right reach out to a few ask them if you're looking for more names ask people who you admire [1:02:34] whose leadership styles you like and want to emulate who they recommend. [1:02:39] Because oftentimes there's certain [1:02:41] you know they have a better understanding of hey this is the type of coach that may want to work with more of the emotional work or this is the type of coach who actually maybe has a more compatible vision of what you're looking for because look there's i'm a [1:02:52] All coaches are different. Like I'm a, you can tell I'm a touchy feely, like heart kind of coach. There are coaches who are, sometimes people want to coach. You're just like, [1:03:00] You know, you grab that brass ring. We're going to pound the table. I'm going to try to push. I'm going to challenge you. I'm going to beat you up. I'm going to be more like a drill sergeant. That's a different style of coach that works with other people. That may be more what you're looking for. So I would just talk to a bunch, do some free sessions, get an opportunity to explore it. [1:03:17] I coach people in the free session. So it's not just like we're talking. I'm going to, we're going to talk about something to coach you. You're going to get a sense of what this looks like. [1:03:24] and then come away and just [1:03:26] Ask yourself, what are your goals and where was there a fit? [1:03:28] And if there's not, just keep looking.

[1:03:32] Amazing. That was very tactically helpful. And I really appreciate all those resources. And we'll definitely link to all that in the description. I have just a couple questions I wanted to ask you outside of coaching around some of your posts that you've written before we get to our exciting lightning round. [1:03:45] One is around this idea of 10x versus 10%. So you wrote this post about the importance of thinking 10x versus 10%. And truthfully, I actually had a post started, 10x versus 10%. And I was like, oh, this is going to be great. And then I googled, oh, shit, Ken's already written about us. So I'm glad that you have written about it and written about it so well. [1:04:07] Great minds think alike, as they say. Now I don't have to write it. [1:04:11] And I'd love to just hear your kind of general take on what this idea is and how to think about 10x versus 10% bets. [1:04:19] Yeah. And again, this is I'm a great synthesizer of ideas. It wasn't my idea. This is a lot of, you know, came from from some thinking at Google and some push. And I think it's really the sense that we think too small sometimes. You'll see that as a theme for some of the other things I've written, too. And there there needs to be a push. Right. If you really want to have huge breakthrough innovation, like you need to be able to try, you need to be able to fail. You need to be able to shoot for the moon. Right. It's where this 10x comes from. [1:04:47] And, [1:04:48] A lot of it is mindset, but a lot of it is also cultural, right? Sort of creating environments where [1:04:52] And I had the great privilege of working [1:04:55] at Google for 14 years and I felt like this was definitely an environment that I got to play in [1:05:00] of being willing to take big swings that might fail. This doesn't mean that the company, we could all be out of business tomorrow, but it's

[1:05:06] It's like if you have a choice between trying something that could have a massive breakthrough, a massive change. [1:05:13] and and playing small ball or you're going to get a bunch of 10 improvements you are [1:05:18] over time, if you're willing to try, if you're willing to fail, if you're willing to push yourself, if you're willing to think bigger, if you're willing to create environments where great ideas come from places that are unexpected, you'll achieve massive, massive breakthrough. And you can find the piece on my website because I use examples from history, but it is a little bit of being brave and trying big things. If you look at all the great technology, the huge breakthrough innovations that we've had, the coronavirus vaccine, right? Like just [1:05:44] this man, do you, there is no small ball in that, right? There was, that was a big, [1:05:49] big swing that there was no guarantee of success, but we were willing to try it. And we were willing to fail knowing that, [1:05:56] failure was probably the more likely outcome. [1:05:59] in the chance that we would achieve something that would really have that level of breakthrough. [1:06:04] And so I think it is what I always sort of challenge people [1:06:07] leaders to do is create the environment where people can step in [1:06:12] and bring those types of ideas. [1:06:16] and not play it safe or not be like, "Ah, boy, that seems like a big one. If we bring that to the CEO, [1:06:21] There's no way they'll take a chance. So let's [1:06:24] Let's ramp down our expectations. Let's bring this little idea in that is a little bit more guaranteed to work. [1:06:28] And so it is the obligation of leaders to create that environment for people to be able to innovate. [1:06:33] Because the ideas are out there, right? There's not

[1:06:36] I used the example of Kodak. [1:06:39] Um, [1:06:40] Kodak invented the digital camera, right? It wasn't like, oh, Kodak, people at Kodak were dumb. They didn't know digital was coming. No, they literally invented the digital camera. There just wasn't an environment created where [1:06:50] the people who had that idea, who saw that potential, who saw that possibility could step up to the plate. [1:06:55] and try. [1:06:56] Give an ear. [1:06:57] rules of thumb of like how many of you are [1:07:00] ideas slash resources should go into these big ideas versus incremental 10% bets? Or is the general advice just like people aren't thinking big enough often enough, so you should always think a little bit bigger than you naturally will? [1:07:12] I think it depends. I mean, it depends on the company. Like if you're, [1:07:14] If you work in R&D, you know, in labs, maybe all, maybe everything is in that category and you. [1:07:20] you build a profile, you know, portfolio, right? I mean, this is, [1:07:23] you know, if you're a venture capital seed investor, if you're working at [1:07:27] a research lab. It's like you're building a huge portfolio of these bets and you're just assuming that, you know, maybe 99 of them will fail, but one will succeed and it'll make it all worthwhile. [1:07:37] You know, most of us aren't in those environments. We're in places where we're [1:07:41] We have real customers buying our products, wanting our products, using our products. And we're like, let's bet the entire company on 50 things that may not work out, may not be right for you. [1:07:48] So I think it is a little bit of a approach. [1:07:51] Um, [1:07:51] at the, [1:07:52] I think it needs to be thought of it. [1:07:54] in a sort of a fractal way though, right? Because [1:07:57] maybe at the company level, [1:07:59] They're sort of thinking, [1:08:00] you know, Google once upon a time had a 70, 2010 thing, where it was like 70% is our core business

[1:08:07] So time was search and ads, 20% as sort of adjacent business, and then 10% on crazy bets that may not be anything. [1:08:14] But I think [1:08:15] That's at the company level, at the individual level, at your team level, you might [1:08:19] you might have your own way of thinking right here. It's like, OK, we've got [1:08:22] I've got 12 engineers on the team. [1:08:24] You know, we're working on any time a bunch of stuff that we know we have to do. This is a bunch of stuff that we hope is like 10%. [1:08:30] And then we're going to create some space for it. [1:08:32] for some innovation, right? [1:08:34] Maybe it's just like one engineer every sprint or it's like, [1:08:38] you know a couple times a year we yeah you create that type of space in your own little air bubble that isn't necessarily [1:08:44] at the sort of portfolio level. [1:08:46] um to try things that may that may not work but if they do [1:08:51] the payoff will be so substantial that it'll make the whole thing worthwhile. Awesome. Very helpful. [1:08:57] Next question is around, I think your most popular post that you've ever written and maybe the thing that [1:09:03] kind of put you on the radar of writing [1:09:05] is around how to hire a product manager. [1:09:08] And maybe this is where you mentioned donuts the first time. Is that right? Or no? [1:09:13] I don't, you know, it's funny. I think that was later. Okay. [1:09:15] Uh, cause I, yeah, I think that was a talk that came back. Okay, cool. Yeah. That was definitely the big one for me. [1:09:21] So here's the question, just to keep it simple. What's one... [1:09:24] piece of advice that you would give people [1:09:27] trying to hire a product manager? What's the thing that you think is most maybe missed or useful? [1:09:34] Um, [1:09:35] Yeah, I think...

[1:09:37] the intangibles, right? There's [1:09:40] When I wrote that, [1:09:42] So basically I wrote that as originally as an email that it was a copy pasta kind of thing for me where people kept coming to me and being like, hey, I think we're going to try to. [1:09:51] hire a product manager or a company can you send over a sample job description [1:09:55] And I'd be like, yeah, you know, before we write the job description, let's talk about what the job is. I'm not sure we all mean the same thing. And so then I wrote that it was in 2005. So this goes back. [1:10:04] to try to define like what the role actually is. [1:10:08] And [1:10:09] And I actually feel like maybe the pendulum swifted. [1:10:12] way too far now where it's like the interview process is so structured. [1:10:17] that you know everyone's doing all these mock they know exactly what questions they're going to get and [1:10:22] It's SAT prep, right? Everyone's like ready. [1:10:25] But we've missed out with can they do the job? [1:10:28] Is this like they can pass the interview, but can they do the job? And so [1:10:31] I think you have to be careful. This is particularly the case if you [1:10:34] or a smaller company, right? You don't have a huge apparatus of like Google and Meta where you've got [1:10:39] sort of interviewing, you know, monoliths. [1:10:42] of [1:10:43] of getting sort of persuaded into, [1:10:46] Maybe this goes back a little bit to the science and the art. [1:10:50] you know, they passed all the sort of technical questions. They do all this, they do all that, they do all that. But then, [1:10:55] You neglect to find out. [1:10:57] Can this person show up? [1:10:59] And, [1:11:00] work with these engineers, these designers? Can they inspire them? Is it somebody that they want to follow or do they have the right mindset for [1:11:07] what this job entails. And we even have agreement on,

[1:11:10] what their job is going to be, right? The number of people you see [1:11:15] you know, earlier in their career be like, well, I thought I was hiring for this, but turns out it's not even product management. [1:11:19] where it's like i thought i was gonna do this but all they want me to do is build fee it's like how how did that not come out in the interview process it's like well i know how it didn't come out because [1:11:27] They answered a whole bunch of structured questions around, you know, they did a programming exercise and they did a presentation and nobody stopped to ask. [1:11:33] Um, so I think that's really the big thing from, um, [1:11:36] from an interviewer perspective and i think same thing goes for the candidates perspective right [1:11:40] you are interviewing a potential client. [1:11:43] employer. You're interviewing a [1:11:45] Boss, you're interviewing coworkers. [1:11:48] Um, [1:11:48] What do you want? What do you care about? What is the type of place you want? You want to be in? What do you not want to be in? How are you? [1:11:55] evaluating that. [1:11:56] How are you asking those questions? Yeah. You know, salary matters, title, all that kind of stuff matters, but like, [1:12:01] You know, you're interviewing a place to plop yourself into. [1:12:05] How are you approaching that to make sure you're making the right decision? [1:12:09] Well, with that, we've reached our very exciting lightning round where I'm going to ask you a few questions and whatever comes to mind. [1:12:19] Just give me an answer. And that's it. Very simple. Does that sound good? [1:12:24] Yeah, inner critic is raging right now. Oh, no. Real time imposter syndrome. Here we go. Yes. Okay, so question one, what are what are two or three books that you recommend most to other people? [1:12:37] Uh, well, 15 commitments of conscious leadership. [1:12:40] Definitely on that book.

[1:12:41] Um, [1:12:42] And it's just sort of ad books I've never... [1:12:45] recommended before, Product Innovator's Dilemma. It's probably my number one favorite book for product managers and product leaders. Amazing. [1:12:52] What's a recent movie or TV show that you've liked? [1:12:57] and loved? [1:12:59] I love Ms. Marvel. [1:13:01] And and I just my whole family were really enjoying it. I love all the MCU stuff. We just eat it up. And Ms. Marvel has been amazing. [1:13:09] Um, and then, uh, watch watching Barry, which is crazy. Sort of like nothing else I think ever on TV. [1:13:16] And then of the last year, probably severance. [1:13:19] It's my favorite. [1:13:21] favorite program of the last, I'd say, last year. Wow. Yeah, that is a trippy show. I've watched it all. We might be severed people. We don't even know. [1:13:28] You won't even know. [1:13:31] Okay, what is a favorite interview question that you like to ask folks when you interview them? [1:13:37] Um, [1:13:40] Well, actually, let me flip it because I just talked about interviewing as the as a interview. Maybe I'll ask a favorite question for people who are being interviewed to ask the employer. Is that fair or is that like turn the tables too much? I love it. Yes. [1:13:53] I didn't... [1:13:54] I think a great question is, [1:13:56] Actually, maybe I have a couple. I think one question that I love is, [1:13:59] How does the company define a product team? [1:14:02] because it answers so much, right? It says so much about culture, collaboration, decision-making, the role of product management. It's sort of like if there's one question you could figure out, what is this culture like?

[1:14:14] It would be asking that. [1:14:16] I think another great question for candidates is, [1:14:19] to ask them to pick an example of something they've shipped recently and just talk about how it came to be. How did a bill become a law? [1:14:26] Was it [1:14:28] you know, [1:14:28] somebody in sales yelled and you know it got added to the backlog and we did was this the next thing is it [1:14:35] you know, a group of people together understanding [1:14:39] customer user needs through discovery and sort of ideating and trying some things and testing it. You know, it says a lot about what it would be like to work there, particularly when it comes to [1:14:50] empowerment and product culture. [1:14:52] So these are probably two good questions. Those are really good questions. I'm going to steal them. [1:14:56] Final question. Who else in the industry do you respect as a thought leader? I imagine this list is very long, but what comes to mind? Well, this list is all of my fellow podcast guests on your podcast, Lenny, which is speaking of imposter phenomenon. You're just an incredible group of all the folks that I love and admire. [1:15:15] Um, [1:15:16] I think, though, because maybe I'll sort of answer it a little bit outside of product because I would worry that I would leave out too many great names. [1:15:24] Um, [1:15:25] in the realms of sort of leadership. [1:15:29] Amy Edmondson is somebody I really admire. She's she's done a lot of the work on psychological safety. [1:15:37] And I really, really value her work, her contributions. [1:15:43] Um,

[1:15:45] There's a [1:15:47] There's a guy named Tom Garrity who has a newsletter about psychological safety. I think he's collaborated with Amy before, and it's one of the best – [1:15:55] One of the best, not the best newsletter I received, Lenny. [1:15:58] Maybe the second best. [1:16:00] um about psychological safety for those of us that are wanting to create environments where people can really thrive and do their best [1:16:07] Um, [1:16:08] you know, I, [1:16:09] In in the coaching profession, I mean, it's sort of the the [1:16:13] coaching profession emerges from [1:16:16] the humanist psychology traditions or the client first work of, you know, Carl Rogers, Abraham Maslow are, are sort of intellectual heroes of mine. And so, yeah, [1:16:26] Um. [1:16:27] you know, they're both dead. I don't know if we're supposed to talk about living people here, but definitely as I think about in my profession. [1:16:33] Yeah, they did. They really set the stage and sort of created the environment that coaching could could even exist. So I will include them. Amazing. Ken, this was such a special episode, unlike any other. [1:16:45] podcast that I've had so far. I can't wait for people to listen to it. [1:16:49] Before I let you go, where can folks find you online if they want to reach out, learn more? And then how can listeners be helpful to you? [1:16:56] Yeah. Bring the donuts dot com. [1:17:00] is my home on the World Wide Web. [1:17:03] All my writing is there. You can get in contact with me there. I have a newsletter that I sort of semi-occasionally send out, but you can find all the stuff that I've ever written and get in contact with me there. And the how to help be helpful question is a really interesting.

[1:17:17] Really easy one to answer. [1:17:19] But that brings me a lot of joy, which is just keep being awesome product folks. [1:17:24] the [1:17:25] You're so much my tribe. There's such a, you're so close to my heart, all the work that you do. [1:17:31] everything you bring into the world. [1:17:34] amazing products that we get to use that I'm sure you're working on right now that we haven't even seen yet that you can't wait to share with us. [1:17:41] And [1:17:41] the cultures and, and, [1:17:43] teams that you make better through your very existence so i would say [1:17:46] You can be helpful to me if I just keep doing what you're doing. What an awesome answer. Thank you for being here, Ken. Thanks for having me, Lenny. [1:17:53] That was awesome. Thank you for listening. If you enjoyed the chat, don't forget to subscribe to the podcast. And even better, leave a review, which helps a lot. You can also learn more. [1:18:03] at Lenny's Podcast. [1:18:04] dot com. [1:18:06] I'll see you in the next episode.