Lenny's Podcast: Product | Career | Growth - Why not asking for what you want is holding you back | Kenneth Berger (exec coach, first PM at Slack)

Episode Date: May 19, 2024

Kenneth Berger coaches startup leaders on how to prevent burnout, advocate for their desired lifestyle, and make a meaningful impact on the world. He’s spent more than 20 years in the tech industry, is a former founder backed by top investors, and was the first product manager at Slack. Kenneth’s core mission is to help startup leaders change the world by learning to ask for what they want, living with integrity, and building genuine relationships even with the people they find most challenging. Currently he is writing a book, Ask for What You Want, in which he aims to share his actionable strategies for creating change in the world. In our conversation, we explore:• Why asking for what you want is so impactful• Three steps to effectively ask for what you want• Challenges that arise when people struggle to ask for what they want• Why hearing “no” is a normal part of the process• The “dream behind the complaint” technique for uncovering desires• Kenneth’s experience of being fired three times from Slack• How embracing fear and discomfort is key to getting what you want• Why discipline is overrated—Brought to you by:• Sidebar—Accelerate your career by surrounding yourself with extraordinary peers• Webflow—The web experience platform• Vanta—Automate compliance. Simplify security—Find the transcript at: https://www.lennysnewsletter.com/p/ask-for-what-you-want-kenneth-berger—Where to find Kenneth Berger:• X: https://twitter.com/kberger• Threads: https://www.threads.net/@kberger• LinkedIn: https://www.linkedin.com/in/kberger/• Website: https://kberger.com/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Kenneth’s background(04:31) The importance of asking for what you want(06:36) Challenges that arise when people struggle to ask for what they want(08:09) A personal example of failing to ask for what you want(09:17) Signs this is a skill you need to work on(10:49) How to get better at knowing what you want(15:28) Why hearing “no” is a normal part of the process(17:29) Getting a “yes” vs. a “hell yes”(19:20) Step 1: Articulate what you want(24:07) Doing an integrity check(26:56) Step 2: Ask for what you want intentionally(30:45) Understanding your influence(34:48) Using complaints as inspiration(36:24) Internal family systems(38:00) Giving feedback(41:24) Step 3: Accept the response(45:22) Kenneth’s experience of being fired three times from Slack(57:30) Advice on being the first PM at a company or startup(01:04:58) Contrarian corner: anti-discipline(01:05:52) Lightning round—Referenced:• Joining as the first product manager: https://www.lennysnewsletter.com/p/joining-as-the-first-product-manager• Internal Family Systems: https://ifs-institute.com/• How to build deeper, more robust relationships | Carole Robin (Stanford GSB professor, “Touchy Feely”): https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin• Leaders in Tech: https://leadersintech.org/• The Three Realities Framework | The 15% Rule | Feedback Guidelines: https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin• T-group weekends at Stanford: https://www.gsb.stanford.edu/experience/learning/leadership/interpersonal-dynamics/facilitation-training-program/intro-tgroup• DBT skill DEAR MAN: https://www.therapistaid.com/therapy-worksheet/dbt-dear-man• Dialectical behavior therapy (DBT): https://my.clevelandclinic.org/health/treatments/22838-dialectical-behavior-therapy-dbt• Vision, conviction, and hype: How to build 0 to 1 inside a company | Mihika Kapoor (Product at Figma): https://www.lennysnewsletter.com/p/vision-conviction-hype-mihika-kapoor• Stewart Butterfield on LinkedIn: https://www.linkedin.com/in/butterfield/• How to fire people with grace, work through fear, and nurture innovation | Matt Mochary (CEO coach): https://www.lennysnewsletter.com/p/how-to-fire-people-with-grace-work• Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Kick-Ass-Without-Humanity/dp/1250103509• Radical Candor: From theory to practice with author Kim Scott: https://www.lennysnewsletter.com/p/radical-candor-from-theory-to-practice• Jonny Miller’s Nervous System Mastery course: https://nsmastery.com/lenny• Managing nerves, anxiety, and burnout | Jonny Miller (Nervous System Mastery): https://www.lennysnewsletter.com/p/managing-nerves-anxiety-and-burnout• The 15 Commitments of Conscious Leadership: A New Paradigm for Sustainable Success: https://www.amazon.com/15-Commitments-Conscious-Leadership-Sustainable-ebook/dp/B00R3MHWUE• Break Point on Netflix: https://www.netflix.com/title/81569920• Living on Netflix: https://www.netflix.com/title/81582076• Wimbledon tennis: https://www.wimbledon.com• Wenshan Baozhong tea: https://redblossomtea.com/products/wenshan-baozhong?variant=31629962820• Tea From Taiwan: https://www.teafromtaiwan.com/—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [e-mail].—Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

You were famously the first PM at Slack, and then you ended up transitioning into executive coaching. For me, the impact was about making this work sustain. So that we're not burning out or selling out, but actually able to pursue these hard goals that we have in startups. What we're going to be talking about today is your personal magnum opus, the output of 10 plus years as a founder and operator in 7 plus years as a coach. The core idea is ask for what you want. Turns out when you actually ask for what you want out loud, you're much more likely to get it. You're hired. How do you know that this is something you need to be working on?

If you're more in the people-pleasing camp, maybe you're used to not asking at all. You're hoping that people are reading your mind. And if you're sort of more in the control-free camp, maybe you're used to ordering people around and saying, go do this now. How do you know what you want? Complaints are great inspiration. Every complaint implies a dream. Let me envision that better future. Let me think about what's an effective way to actually move towards that.

See what it's like to not be sort of living in fear all the time. Today, my guest is Kenneth Berger. Kenneth coaches startup leaders to help them avoid burnout and live the life that they want. He was the first product manager at Slack and spent over 10 years in tech before transitioning into coaching. His core focus with leaders is to help them learn how to ask for what they want. This sounds really simple, but as you'll hear in our chat, this one skill is at the core of so many of the struggles that people have in their career and in their life. Kenneth shares a ton of very tactical advice to help you figure out what it is you want, how to overcome the resistance that comes with asking for what you want,

how to actually ask for what you want effectively, why the most important step is hearing the response that you get when you ask for what you want, and all of the things that will change in your life if you get better at this one skill. Kenneth also shares the story of him being fired three times from Slack, which is hilarious. With that, I bring you Kenneth Burger after a short word from our sports, And if you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. It's the best way to avoid missing future episodes, and it helps the podcast tremendously. Let me tell you about a product called Sidebar.

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leaders are matched with peer groups, to lean on for unbiased opinions, diverse perspectives, and raw feedback. Guided by world-class programming and facilitation, sidebar enables you to get focused, tactical feedback at every step of your own. your career journey. If you're a listener of this podcast, you're already committed to growth. Sidebar is the missing piece to catalyze your career. Ninety-three percent of members say Sidebar helped them achieve a significant positive change in their career. Why spent a decade finding your people when you can meet them at Sidebar today? Join thousands of top senior leaders who have taken the first step to career growth from companies like Microsoft, Amazon,

and Meta by visiting Sidebar.com slash Lenny. That's sidebar.com slash Lenny. This episode is brought to you by Webflow. We're all friends here, so let's be real for a second. We all know that your website shouldn't be a static asset. It should be a dynamic part of your strategy that drives conversions. That's business 101. But here's a number for you.

54% of leaders say web updates take too long. That's over half of you listening right now. That's where Webflow comes in. Their visual first platform allows you to build, launch, and optimize web pages fast. That means you can set ambitious business goals and your site can rise to the challenge. Learn how teams like Dropbox, IDEO, and Orange Theory, trust Webflow to achieve their most ambitious goals today at webflow.com. Kenneth, thank you so much for being here. Welcome to the podcast. Yay. Thanks for having me.

I love that. Yay. That should be a tradition that everyone. I love that. So we originally met when I was doing a post on being a first product manager at a company. You were famously the first PM at Slack. And then you ended up transitioning into executive coaching, which is what you do now. What we're going to be talking about today is something that you described to me as, quote, your personal magnum opus, the output of 10 plus years as a founder and operator

and seven plus years as a coach to startup leaders. And the core idea is simply asking for what you want, which sounds really simple. So let me just start broadly. Just why have you found that this skill, this one idea, is so core to so many of the challenges that people run into in work and in life? You know, if I had to answer in one word, it would be integrity, right? And I think that it's one of these funny things where, you know, everyone thinks they already know asked for what they want. Like, we all ask for what we want. We order our coffee in the morning,

and we all think we have integrity. No one walks around thinking, I'm lying to myself all the time, or lying to others, certainly. And yet, we tend to kind of fool ourselves a little bit, right? You know, when it comes to, are we really pursuing the things that we want in life? Right. And I think, to me, the flip side of that is sort of the reason that the stakes around asking for you want are so high. Because, yeah, you know, if you're, we can't guarantee we're going to get what we want. But if we're asking for it regularly, if we're listening to the response, we're respecting the nose we get from the world, then we can kind of get the sense of, yeah, I'm honoring what's important to me, I'm honoring the world's response, and I'm moving forward to a response.

And if we don't do that, well, then we're kind of fooling ourselves that we're actually moving towards what we want. There tends to be all these sort of unexpected secondary and tertiary effects that come out of that, right, of stress and frustration and unhappiness. because, of course, asking for what we want, pursuing what's important to us in life is just one of the most important things of fulfillment, right? Of what's, what's important in sort of achieving our purpose. But it's just some challenges that people have in their life and career that are just rooted in this, doing this badly, not asking for what you want, not knowing what you want. For me, with clients, I think what I'm often looking for is kind of the sense of being stuck, right? because everybody's got frustrations, everybody gets nervous at work sometimes.

But if we're in the same stuck place week after week after week in our coaching sessions, probably you're trying the same thing and not getting any different results, right? It's sort of that definition of insanity thing. And so really, I look at that and say, okay, you know, maybe you're asking for what you want, right? Maybe, although often people aren't. But even if you are, you're probably not achieving it, right? You're not getting the results that you want. So why are we not learning from that?

Why are we not sort of moving forward, getting new data, trying something new, actually treating it as a sort of iterative development discovery process? So I think that stuckness is one thing. And I think the other thing I look for is interpersonal conflict, right? Because I think that, you know, one mode of not asking for what you want well is kind of holding back and not really saying it out loud. And I think another really common mode is coming with a lot of entitlement. Like, you know what?

You better do what I say. I'm your boss. you're my report, you better obey or agree or whatever it is. And of course, the danger of that is interpersonal conflict. Even if you are their boss, right, that's a really disrespectful way to come into the conversation. And yeah, it's an obvious source for a lot of issues. Before we get into how to learn to do this better and more of why this is so important, is there an example from your career where you did this really badly or you didn't ask what you want. There's so many examples. I think we'll eventually get into the story of how I was fired from Slack.

But I think for me, you know, the thing that always came up was just being attached to being right. And I think a lot of us sort of get into this boat. If we enter into a meeting and we're sure from the first moment, I'm right and they're wrong. And I think that especially in product management, right, like we're supposed to be the holders of this vision for what the product should be. And so it's easy to come in with a lot of conviction and not really a lot of openness to other ideas. And sort of often what I try to introduce people to and I learned all this stuff the hard way, believe me, is it's fundamentally disrespectful to go into a meeting already deciding that you're right and the other person is wrong. Because you can't know that for sure, right? There's always a new perspective, new data that could come in. And so you want that conversation to really be a back and forth.

And if you're coming in with this really ingrained sense of righteousness, you can't do that. There's no way to have that conversation, respect. I think you may have already answered this question, but I think it's really important is how do you know that this is something you need to be working on? How do you know, like, I really need to pay attention to what Ken, it's about to tell me. You said one is you feel you're stuck in your career, something you're just not making progress and this could be the answer. Or you said there's interpersonal conflict and you're just having a lot of conflict people.

Are those the two answers? There are more. I think those are great things to look for. I think it's also good to look for kind of a sense of things being high stakes. right? Because I think part of what can create a lot of sort of conflict and difficulty in these situations is a sense of this is life or death, right? And that was certainly how it was when I was a founder, right? Okay, normally, you know, when I was at Adobe, it's a big company, you know, they're going to be fine other way no matter what I do, right? I can be easygoing, you know, let someone else have their way

in the meeting. But when it was my company, right? When it was my vision on the line, I didn't feel especially flexible, right? The stakes seemed really, really high, right? This is the success of my of my vision, my reputation is on the line. And so I think often when the stakes feel high, we're kind of focused more on the fear of what we don't want to happen than on actually achieving what we do want. And that's a really critical distinction, right? Because if we're running away from our fears, it doesn't necessarily mean we're getting anywhere meaningful for what our desires are. And so that sense of high stakes that often we can get, whether it's in interpersonal conflict or being afraid of asking you for what we want.

that can get us really focused on the fears rather than focused on the course. There's a question I was going to say for later, but it's something that's very top of mind for me is knowing what you want. Like, how do you know what you want? There's basically knowing what you want and then asking for what you want. And I often, I'm like, I try to, I'm like, I like, I like, I like equanimity in my life. And so I often don't ask for what I want or kind of push down maybe what I want or I don't think about what I want. I just want other people to be happy. And I'm curious what people can do and what I can do to get better at knowing. Here's what I actually want.

Here's what would make me happy and fulfilled. What are some skills there I could work on and other people can work on? Well, first of all, I'd say you're very far from alone there, right? I mean, I think the people pleaser coping strategy is one of the sort of most classic. And it is effective, right? In the short term, right? Like, oh, you can feel safe and calm when other people are generally happy with you. and the cost tends to be long-term, right, in terms of, am I really pursuing the things that are important?

So, you know, one of my favorite techniques here is this concept they call the dream behind the complaint. Because, you know, you're right, that like we tend to not be that great always at really dreaming and envisioning and saying, this is my dream of what I want out of life, right? That can sound really scary for people, but we're very good at complaining, right? Usually people are very good at saying, oh, my God, there's this thing happening at work. it's so annoying or there's this person that, you know, really bothers me so much. Why are they always like this? And so the magic of that complaining is that every complaint implies a dream, right? It implies a better world where that complaint is resolved. And so, you know, often that's the tool that I'll take people to first to say, all right, great, like, let's complain, right? It feels so fun and good

and releasing to complain. And let's look at what that sort of implied world is, you know, behind that complaint, right? What is this vision? And then to really check, right? Okay, let's imagine you get that. That's the world of the future that you get. How does that feel? Is that big enough? Or is it kind of meh, right?

Are you like, oh, you know, my dream is that, you know, I get to speak up a little more in meetings. It's like, well, that's probably not 100% of your dream. Like, what's really behind that? And so I think it can, it can, that check can help you sort of level up to say, is this really an inspiring dream for me that's going to motivate me more than those fears that might be hiding the background. And on the flip side, with entitled people,

you can also get really unrealistic dreams, where I might say, okay, so it sounds like what I'm hearing is that your dream is that everyone obeys you and automatically agrees with you no matter what. And they sort of say, I don't know if that's quite my dream, right? And so if your dream is so embarrassing

to say out loud, you can't even really own it, maybe that's not the right dream. And so that checking, whether it actually feels inspired, but also sort of credible and possible is a good way to sort of find that middle ground. We're like, yeah, this dream is hard. I don't know if I'm going to get it. But damn, it's worth trying, right?

Like, I want to go for. I love that. For someone that wants to try this on their own and help themselves get better at this without you being there, what is it that you do? Is it you dream about what would make you happiest? Is it like complain and see what's at the root of it? Is it just imagine a world where you're really happy and see what emerges? specifically for articulating what you want, because that's kind of the first step of the,

you know, asking for what you want process. It really is as simple as that, right? Of let's start with, you know, sort of what's what you have consciously in terms of what you want. And, you know, if you have trouble, then we can try looking at complaints and sort of starting to articulate a vision out of that. But to me, really, what's interesting about asking for what you want is that on the surface, it's very simple, right? I mean, the steps I outline are articulate what you want, ask for what you want intentionally, and accept the response, right? And then try again, right? Because it's an iterative process, right? We're warning from the response and what it tells us, because the response is usually no. And so really what tends to be hard there, I mean,

that's a straightforward process. It's not rocket science. What's hard there is the resistance, right? The parts of us that are not so excited about that. The thing's asking for what we want is scary and articulating a big dream that we might not get is really scary because, God, if I don't get it? What does that mean about me? Am I a failure? Or, you know, what does it mean if I respect the no? What if I ask for my big dream and someone tells me I'm not going to get it? Like, what does that mean? How am I going to feel? And so working through all that resistance is really a lot of what tends to be tricky about asking for it because otherwise it's, yeah, articulate, accept. Okay. You're getting into where we're going to go. Before we get their final question,

this idea of dealing with no. I think this is the other big locker for people is like, it's so scary to ask for like something I really want or or ask for something big that is really important to you. What is it that you advise there of just kind of getting over that the sphere of just like asking for what you want? So I have a more expansive definition of no than than most people I think because for me it's it's not a yes unless it's a hell yes, right? Because you really want enthusiastic consent, right? Not just a maybe kind of, I'll try. You know, we'll see. But yeah, absolutely, let's do this, right? And I think that often it's so tempting to settle for something less than that, to say, oh, well, okay, we'll give that a try. And that often comes to bite us later on,

because we accept this thing that's short of a hell yes. And then we realized later on, oh, yeah, they weren't really in, right? They didn't show up to the party, right? Or like, they didn't deliver on time because my CTO said, yeah, maybe, I think maybe we can deliver by, you know, May 1st. And then May first comes and surprise, surprise, your milestone is not done, right? Because you didn't, you didn't sort of go for that hell yes. And so I think part of what I encourage people to do is one to really hear anything short of a hell yes as a no. And so it's not a bad thing, right? Mostly the world tells us no. It's actually really great data. It helps us figure out what are we going to try next. What are we going to try next, try next, try next. Because that's what's going to help us learn how to actually get to that hell yes.

And part of that asking process is of not settling for it, but actually asking and saying, hey, you know, I'm hearing maybe you're lukewarm on May 1st as a date. Like, what would be a hell yes day for you? We could say, absolutely, we can deliver on that. Right. And that way, we're not making them wrong for saying no. We're saying, no, of course, you get to say no. Everybody gets to say no whenever they want.

So, but let's get to a hell yes. What would it take for us to get there? That's a really helpful framework and phrase to use is just what would it take to get to hell yes, not just what would it take to get to you feeling comfortable with this, or what would it take for you to just agree to this? It's more a hell yes. And your point there is hell yes is when they actually fully agree. Yeah, oftentimes people kind of like, yeah, yeah, yeah, yeah, and then they don't actually follow through. Some people call this a whole body yes, because sometimes like your head is saying yes, but your heart is saying no, right? Or your gut is saying no.

And so I think you can really feel in your body when you've got a hell yes, right? when all of you is fully in and ready to do this. And this applies to, you're giving examples here of just like getting, like a line and deadline. I imagine the same skill applies to everything you in like, like relationship questions and friends and family and work. It does.

And I, and, you know, it is something universal, but I do think of it as being particularly relevant to my work with startups, because you know, I work primarily with startup founders. Because with startups, you know that most,

mostly they fail, right? Like, we all know the numbers on that. And so to me, there's a sort of perspective you have to take if you're going to sort of operate in the startup world of being okay with not knowing that you're going to get the outcome anymore, right? You know, a lot of people we operate in a safer world where we're more clear exactly what the outcomes are going to be. But if you're a startup founder, you've got to be okay with, I'm just going to go for

this. And I know I probably won't get it. But it's so meaningful to me, I'm going to go for it anyway. And so to me, that's not just about the big picture of running a startup. It's about really anything you might want in life because that's such a useful perspective to say, I know I'm not going to get it. I know I'm not guaranteed to get it. I'm not going to be attached to that.

I know people aren't obligated to tell me yes. But I'm going to go for it anyway, right? Because I want it. And that's enough. So let's actually get into the skill of learning how to actually say, ask for what you want more effectively. You already described three steps. So maybe just describe them again and let's just walk through them.

So the first step is articulating way more, right? And we've sort of gone into this a little bit. But to me, I think that the key places that people tend to sort of have missteps here are one in, one in this phrase, it's fine. I think of the it's fine cartoon with the flames, you know, the dog, I think it is. But I think a lot of us fall into that trap saying, you know what, I'm fine. I actually, I don't need anything. I'm good. and again, this is tempting, right?

Because it's so nice to have this idea that I'm fine, I don't need anything. And in a certain way, that's a nice attitude, because we're not guaranteed anything. So it's nice to be okay with the status quo. But for those folks, often what I'm encouraging to do is to really tune into the parts of them that maybe aren't so fine. I'd really, you know, I prefer it a little bit if things were this way. Or, yeah, I'm a little bit bothered by this or I'm a little bit nervous about this. And so kind of tuning more into those subtle emotions that are pointing them towards, sure, I'm okay with the status quo, but I want something more.

And so helping them articulate that in a clearer way where they can want something without being attached to having to get it. You know, the other extreme of this is people who, you know, articulate these sort of, you know, wildly unrealistic. So this is the founder that just wants everyone to agree with him all the time and to obey him immediately, right? And so for those folks, it really tends to be more about saying it out loud. Because once you say it out loud, it is clearer. Yeah, that's not, like, I'm not, that's not really what it's about. And so for those folks, I tend to ask them to go deeper to say, yeah, I know you're not a control freak, right? You don't want, you know, everyone to think exactly what you think. What's it really about? What does that get you? And so often it goes from being this kind of more kind of objective external goal to being a more kind of social emotion. goal of, you know what, I just want to have a team that feels really aligned around me.

And we're just ready to go for it and we've got each other's backs. And that doesn't mean we agree with each other all the time or that we're 100% aligned and everything. But it doesn't mean there's a certain feeling that I have when I go into work, even though I don't know that we're going to get what we want or that everyone's going to agree. Do you have any examples from your time you could share if someone articulating what they want and figuring out how they articulate, how to articulate what they want,

just to make it even more real. To me, a lot of the classic examples are around feedback, right? Because, you know, I work with a lot of founders who, you know, are not the sort of classic control freaks, right?

They're super nice, right? And their teams love them, and they love their teams. And so for them, it can be really hard to deliver, to deliver hard feedback, right? To deliver negative feedback, and even more to actually create consequences.

Because the thing about accepting other people's nose, is that, sure, they can always say no. Everybody gets to say no whenever they want, but there are consequences, right? And so the classic thing I see with the nice founders is they're really afraid to actually create consequences when people are not living up to their expectations, right? When they're not aligned with the culture, they're not sort of delivering in the way that, you know, the CEO wants them to be delivering.

Because it doesn't seem that nice. They're like, oh, I think of myself is nice and of being so kind and of people loving me. And it's like, well, that doesn't mean that there aren't consequences for their actions, right? Part of really respecting them is respecting that they can make the choices they want and they're grownups enough that they can deal with the consequences of those choices. Can you even get more concrete there? Is it like, we need to hit this date or there's going to be big problems? Or is it like, I need you to hire this large of a team?

I don't know. Like what is it that they're not articulating that they later realize, oh, here's what I need to articulate? So I think sometimes it is about alignment, right? the disagree and commit. So I see that a lot, right, of like, you know, founder saying, hey, you know, I'm super respectful of, you know, of your differing opinion here, and I totally validate you and I appreciate you. And thank you so much for sharing that. But they're not willing to go that extra step and say, yeah, but this is the call. And I need you to sort of to actually follow through

with that. Right. And I understand that might be disappointing or frustrating or what have you. But part of the expectation of this role is that, you know, you can roll with disagree and commit sometimes when that's necessary. That's an awesome example. I fully get that, and I could see how many people are not, how scary that is to a lot of people. One is just like coming to terms with, this is what I actually want to be doing,

but I just don't feel like I can because it's going to, I think, upset people. Yeah. Okay. So what else can you suggest people do to help identify what it is they want and articulate what they want? So you talked about pay attention to just like, oh, this would be better. If like, if this changed, I would be happier. Or things would probably run better.

that's a really cool example of how to think, do that because that's easy. Just like, oh, yeah, if we like actually can make a decision in this meeting, that would be really cool. Maybe we should try to do that and ask for that. Is there any other tips and approaches to helping you figure out what you want? It always comes back to integrity, right? And a great way to sort of do an integrity check is just look for how I fully express myself, right? And so I think we've talked a little bit about sort of charting your feelings as a piece of that.

I'm like, yeah, am I really tuning into like how annoyed I am or how frustrated I am or how nervous I am, right? Because if I haven't fully own those feelings and express those in whatever way is appropriate, then probably I'm not fully in integrity. And I think saying what you have to say is a piece of that too, right? Gosh, is there something that I just, I keep thinking about and I'm just like, you know, three or four days, I'm just like, man, I really want to say this to this person. At this point, you're probably out of integrity because there's something deep in you that really needs to say this, right? And so it's, to me, articulating what you want is really about mindfulness, because it's about checking for all these things. Like, yeah, like, what is the part of me that's not fully expressed? Because it doesn't mean I'm going to get what I want or the people are going to,

you know, sort of, you know, give me all my dreams immediately. But it feels so much better to have it out, right? That sort of suffering, you know, that fear. usually comes from holding it in and saying, oh, having these stories of, I'm not allowed to say that. It's not appropriate to express that I'm bored in this meeting, right? Versus saying, like, probably a lot of people would be grateful if we said out loud. I'm bored in this meeting. Let's move things along.

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I need to change this. This needs to change. I'm just scared to say this, to bring it up, to change the way people are operating to ask for what I want. What advice can you share for people to actually do this?

So for asking what you want, I think the really important tweak here is asking intentionally, right? Because I think a lot of us are kind of stuck on a certain track that's comfortable for us when we ask. And so if you're more in the people pleasing camp, maybe you're used to not asking at all. You're hoping that people are reading your mind and just magically knowing what you want. And if you're sort of more in the control-free camp, right, maybe you're used to ordering people around and saying, go do this now. And so, you know, for both of those folks, right, it's not about, you know, I think if you ask any of them, right, like, is this working for you?

Like they'd say no, right? Of course, it's obvious from an effectiveness standpoint. It's not working well. But they more just haven't embraced that, yeah, you can do it a different way, right? That they only really see one way of doing it. And so part of asking for what you want effectively is really just recognizing the rut that you get stuck in and sort of working through all those narratives that make us resist asking in a different way, right? Because often the people who don't want to ask have a story that says, this is too risky or, you know, or it's not worth it. They're going to say no anyway, right? So why even bother? And so, you know, these are all, you know, these are all sort of very common things that people go through, but then they end up not actually asking for what they want, now actually expressing who they are

and what they stand for in the world. And that has a really serious cost, right? I think that, you know, we sort of tend to tell ourselves the story, oh, this is fine, I'll be fine, versus owning, like, I'm going to, I'm going to be living my life, like not asking for what I want. Like, do I really want to be at my funeral and have people say, oh, Kenneth played it safe? You know, he didn't really go for his dreams, but he was nice. No one was ever mad at him. That's not what we want people to say is our eulogies. No.

That's good motivation. Okay, so saying this example you gave of like, I just need, I need us to make a decision. I know I'm trying to keep everyone happy, but we need to make a decision. do you have advice for maybe phrases of how to approach? You talked about making intentional. How do you actually go about doing that? Is it like the way you communicated it? Is it something else?

How do you actually do this without pissing people off and also just like risking too much? Well, and so, but even implicit in that question, right, like there's, to me, to me, that question of, oh, how do I do it without there being any risk of ever pissing anyone off? right, that's a piece of the resistance right there. And so this is a great example of the type of work that we have to do, right? Because, you know, in theory, asking is easy. Oh, you just try some way and like maybe people are pissed off and maybe they're not. But like, probably is going to be fine and you'll have the chance to try again and iterate and learn from it. But often we get stuck so we don't get to go through those levels of iteration because we want to make sure we're going to get the outcome we want. We say, oh, well, I'm not willing to ever piss anyone off ever. And so I I'm just going to be stuck at this step because, like, I haven't figured out what's going to guarantee me. And of course, there's no guarantee. We can never guarantee that people are going to feel a particular way.

And so part of asking for what you want effectively is actually bringing some compassion for yourself. God, like, of course we all want to be sure that the way we ask is going to be effective. And no one's going to be mad at us and we're going to get all of our dreams come true. But yeah, now we don't get that, right? Like, I wish we did. That would be nice. but is that worth not pursuing your dreams in life? Such a good point about what you identified and how the way I think about it and the way I think a lot of people I think about is just like, I don't always do this without causing anyone any pain or risking anything going wrong.

I mean, that's to your point, part of it. So you talk a lot about founders. You work with a lot of founders. A lot of listeners here are not founders. They're product managers. I see he's on teams, other functions that don't have, you know, power, quote, unquote. is there anything that you suggest these folks do differently or think about this differently, or is it kind of the same thing? In the end, everyone has power in some way. How do you,

how do you would you think about this if you're just like, say, a product manager, individual contributor? I think one of the most important balances in terms of the asking step is both asking clearly, but asking with great humility. And this actually works whether you're in a position of power or not. Because I think a lot of folks will go so far to the end of humility, they say, well, I'm not going to go, I'm not going to say this out loud at all. But in fact, if you're willing to say, you know, like, I really disagree with this product decision and like I, I would really prefer that we make this different decision. And I know it's not my call and I'm just one opinion and a lot of people are going to see things differently. And that's fine. But it's

important to me that you know that. Right. And so what do you think? Like, are you willing to reconsider this? That's such a great approach. It's like very not scary to say that. It also, I think, highlight something I wanted to touch on is I think people have a lot more influence and power than they think they do. Say a PM on a team disagrees with a plan for a product. Like, people actually care about your opinion and you could actually change things by just telling them, I don't think, I think this is a bad idea. And you often don't. Is that what you find that people have a lot more influence than they think they do? Anything along those lines that comes up. You're actually, you're giving me deep goosebumps because this is, I,

I think this is a really underappreciated thing in terms of asking for what you want, because especially in the PM world, we're trained to look for data, right? We're not just going to state an opinion. We're going to say, oh, the AB test said this, right? Or like 30% of our users do this, or the ROI on this is X, right? And data is great. Like, we love data for a reason, of course. And I think people forget about exactly what you're highlighting, that your relationships matter

and that just your opinion because you believe something. or because you want something, often that's enough, right? Because guess what? You're in a relationship with these people you work with. Like, they care about you. Like, you have some sort of leverage with them. And I think that often, you know, often people go the other way and say, oh, I've got power. I'm going to try and leverage it. But actually, if you go the other direction and you're humble and you say, I know I can't make you do anything, right? It's not my call to make. But man, like, this is really what I want. I'm just going to put it out there and like, and ask that I think it feels really vulnerable and uncomfortable to not lean on data as a sort of way of saying, no, no, I'm right.

So you should believe what I believe, but just say, actually, I don't know that I'm right. This is just what I think. And I hope that's enough on its own. Do you find that that's actually a crutch a lot of times to people not saying anything is they don't have that data, they don't have evidence? And they just, I shouldn't say anything because I don't, if someone asks for why I don't have a great answer, I just, I just think this is what it should be. Totally. Well, and, you know, I think there's a balance there as with anything. Like, is ignoring data and going in gut all the time, great? Probably not, right? We use data for a reason. But I think there are all these, you know, sort of all these moments when we are making a gut

decision, right? And having all the data there means having the opinion set out loud. And I think often the dangers of people saying, oh, I don't have data to back this up. It's just what I think. And I'm not sure people are going to agree with me. So I'm just not going to say it. And so we don't have the data of all those gut opinions of the subject matter experts in the room, right? Even though that gut information to me is just as important as anything you could get from, you know, the SQL database or whatever. Before we move on to step three, you already, you talked about the kind of the opposite of asking for what you want, that was just step two, is just complaining and being angry later.

Like, I knew this project was going to fail. I knew this was a terrible deadline. I knew this design was not great. Anything more you want to say along those lines are just like, if you're not asking for if you want, complaining is often a sign that you're, you should be doing that more. To me, complaints are great inspiration. And so I think the, you know, to me, you know, like I love radical candor, for example, right? You know, where, where I try to go a step further than radical candor is to not just say,

hey, here's my feedback, you know, just wanted you to know, but to say, and I want something, right? Like, I would like to see an outcome, right? And so I think that to me it's all about the effective framing that, you know, the complaint is probably not going to be an effective way to do it, but it can be great inspiration to say, gosh, that complaining means I'm frustrated. What am I frustrated about? Let me envision that better future. Let me think about what's an effective way to actually move towards that. What's an effective way to communicate, you know, that desire? Like, that's actually likely to get me towards a yes. And so when we actually embrace that sort of, you know, frustration, annoying, complaining thing, and follow that thread down and think about how to be effective that way, we can actually get something really compelling and useful. But it requires actually embracing that part of ourselves that sometimes we're a little bit ashamed of up. I don't like

that whiny part of myself. Like, I'm just going to push that one down versus actually taking what it has to say as important data. That's a really good point. I think that's actually another blocker for a lot of people is just I don't want to be a complaining person. I just want to be like, let's do this. I'm in, let's go. Let's I don't want to be seen as a squeaky wheel. Is there anything you say there about as a resistance point for people? Well, I'm a big fan

of internal family systems, which is this sort of psychotherapy technique that really talks about parts and the sort of parts of ourselves and the ways in which they don't always agree with each other. And part of why I love this approach is A, because we already use this language, right? We say, part of me

thinks this, a part of me thinks that. And really, when I talk about how to work through resistance. Really, it's about embracing and validating all of our parts. Because often we're really comfortable with one part of ourselves that we think is, oh, this part is virtuous and good and great. And this part is whiny and bad and not great. And I don't respect that part of me as much. And so really to sort of ask effectively, we generally need to embrace all these parts and really bring in all the information they're bringing in. Because if we ignore the part that's really scared to ask, well, yeah, then we're going to stay stuck.

Versus if we come in and say, hey, buddy, like, why are you scared? Like, you seem terrified. What's going on? Oh, well, man, like, you think your whole professional reputation is staked on this, and you're an imposter, and they're going to find out, and then you'll never work again. Well, of course you'd be scared. That makes a ton of sense.

And by embracing that instead of ignoring that and being ashamed of that, that is often how we soften those fears and say, yeah, like, I know that's scary, but we also know that's not really true, right? Like, you're not an imposter, right? You're an experienced profession. Man, there's so many threads. We can't follow here this whole line of. What internal family systems, right?

That's its own podcast episode potentially, and then Imposter Syndrome. We've touched a bunch of different podcast episodes, but I'll avoid going in that direction. Something you reminded me of is we just had Carol Robin on the podcast who taught this class touchy-feely at Stanford for a long time, which is all about helping people learn how to deal with other people, which we never learn in life. It's like a class how to learn to work with other people. I took one of Stanford's T-group weekends, summer of 2020, I think a month after George Floyd was murdered and was facilitated by a black woman. And it was one of the most profound transformative weekends of my life. I mean, because T-groups already people rave about them, but having it at that point in history with those people in the room, oof.

A lot of tears, I imagine. It was, it was crazy. I mean, it was really wild. I feel like every single person that has gone through. I think it's called Leaders in Tech, because of the broader umbrella term. And Carol talked about it. Everyone that has gone through it 100%

and it's told me that it's a transformative life experience for them. And you had a bonus transformational piece. So anyway, if people want to check out that episode, I will link to it in the show notes. But the reason I brought it up is Carol shared this framework for how to actually give feedback in a way where people can receive it that I'll just highlight here. I have it here.

And it's somewhat related. to nonviolent communication, which is what you touched on. And she told me, actually, she taught this way before nonviolent communication came out with their whole velocity. And it's basically, when you want to give someone feedback, the template is when you do a behavior, I feel a feeling. And she's big on like, say actual feeling word, not like I feel like or I feel that, blah, blah, blah.

And step three is, I'm telling you this because and then what you want them to change. Do you find that sort of approach helpful? I do. I teach the same thing. And yeah, I think, you know, sort of Carol's approach and nonviolent communication, DBT teaches a similar approach. They call dear man. To me, what's DBT? It's a dialectical behavioral therapy.

It's related to CBT. So there's kind of rough consensus, you know, in the sort of personal development world of how to ask. and really what they have in common is around kind of staying really factual. Because, you know, I think that, you know, what can we know factually? Well, we can know our thoughts. We can know our feelings because no one else can know that better than us. And maybe we can trust our eyes, right? Like, you know, what would a video camera have recorded?

Right. And that's about it. And so I think often we get really distracted by all these stories we have about the data. But when we bring it back to that fundamental core of this is what I think, this is what I feel, this is what I've observed in the world, it tends to make the ask a lot clearer versus these stories like you mentioned of, you know, I feel like you're an asshole, right?

It's like, well, that's a story. That's not a fact. Yeah, I feel that is not the way to say I feel. What do you actually feel? Yeah. Okay, so let's move to step three. We've been going on this whole tangent of therapy and stuff, which is amazing.

But let's make sure we cover all three steps. So step one, again, was articulate what you want. step two is ask for what you want what's step three so to me step three is actually the trickiest for most people um so far they're all tricky to me oh yeah they're all they're all tricky for sure the most tricky okay but step three is accept the response and it might seem so simple right but it actually is kind of subtle and so you know one one reason is that idea of you know sort of the whole body yes or the hell yes, right? Because I think often we really want a yes. And so we're very, very biased to look for a yes versus accepting, no, that was a no, right? If someone kind of made this face,

like, that's a no. It doesn't matter what comes out of their mouth. Right. And so the challenge of accepting the response is often that of, you know, of hearing the no, but not over-accepting or under-accepting. Because I think sometimes what people who are really afraid to ask will is they say, oh, well, that was a no, so it's no forever, and I should never ask again, and my dream is dead, and nothing's ever going to happen for me again, right? And that's because they get so scared, right? But actually, no, like, that's over-accepting, right? The no is just from this person, right, in the way that you asked, right? Which doesn't necessarily mean anything about the next time you ask to a different person in a different way in a different time.

And on the flip side, right, in that sort of more control-free mode, I think for them, they'll often sort of kind of skip over. over the response, say, well, you know, they said no, but they don't know what they're talking about. Or they're my direct report. So, you know, they have to do what I say. And so these are all, these are all kind of, you know, these are all kind of fundamentally disrespectful ways to operate in this relationship. And when we're talking about asking for what we want, we're talking about influence. So you need to have good relationships. You can't be influential with bad relationship. And so really accepting the response is about, yes, I'm going to be genuine about what I want,

but I'm also going to genuinely care about you and have deep respect for your, your sort of ability to consent or not consent to whatever the ask is. Because I think the counterintuitive thing is that often when we really respect people's nose, right, it can actually be more influential, more motivating, right? If someone says, okay, no, I'm not going to, I'm not ready to deliver this on time. Be like, okay, well, I'm going to give the project to another person. Right? Like, I'm taking your no at face value and they say, oh, gosh, well, I didn't realize that

was going to be the consequence. Maybe I can get it done by that time, right? And so that way, you're not forcing them. You're not coercing them, right? You're just saying, no, you said no. So your no is no, and I accept that. So it feels like part of the skill here is preparing, is like knowing. Some people will just say no, and that's okay.

Like you're, that's part of the experience. Part of it is if there's this like not yet components. We had Mahika Kapoor on the podcast. She has a PM at Figman. she had this really great approach to building new things within companies is just like everything to her is not yet. I know is it not yet. And the way you phrased it is it could just be the way you asked.

It could be like maybe they'll agree if you can figure out a better way to pitch the thing. Is there anything more you can add there about just this idea of it's not no forever? Acceptance of the response is primarily an emotional regulation issue, right? Because once we get our emotions intact, it's just, is it yes or is it? is it no, right? And if it's no, which it probably is, because most of the time the world tells us no, then the question is, all right, what can I learn from this? What am I going to try next? And so when we're able to emotionally regulate, it's all very cut and dry, right? It's like, okay, here's data to tell me what to try next. And so really 99% of the challenge tends to be

all the feelings that come up for us when we hear a note, right? Because we hate hearing no. It's so uncomfortable. And so part of the practice of getting good at asking for what you want is recognizing you're going to hear no all the time and that's completely normal and fine. It doesn't need to be something so scary or awful. Easier said than done in real life. Is there an example of either a client of years? I know you can't actually share specific details,

but I'm just curious if there's an example that comes up of someone dealing with this and getting better at it, either or your own career. I gave a talk about this sort of right after it happened, but I was fired from Slack three different times, which I feel like has to be some kind of startup record. I don't know, you know, who would be the record-keeping body for this. But, you know, now 10 years on, you know, I have different perspective, of course. And so this was, you know, almost exactly 10 years ago, spring of 2014, you know, and I just got in the job as the first PM at Slack. And it was already the hottest thing out there. It was only a couple dozen employees. And I came in excited, but also a little insecure because I just come off kind of my breakup with my co-founder. I just wanted to kind of put my heads down, you know, put my head down and do a good job. I was engaged at the time. So Slack already knew. I was going to be going away

on a bachelor or backpacking trip I had wedding and honeymoon in the fall and so I kind of came in kind of naive and overconfident of like I've been a founder I've worked on iconic products I know how to do this

I'm a pro I'm just going to go in and do the work and so instead of getting really clear on what does success look like here or what's your culture or like you know

what are your expectations of me I kind of just went in and made my best guess and went for it and lo and behold turns out like what I came in with that supreme overconfidence was not what they wanted at all. They, you know, they'd kind of been in the trenches like reinventing from the game, you know, to swag. You know, they've been through layoffs, really hard times together. So they wanted someone to come

in humble and to kind of earn their trust of this kind of core team that had been together for years. And so I, you know, I just didn't get any of that, right? Like I wasn't, I wasn't sort of hearing that feedback. I wasn't hearing those nose. And I wasn't articulating what I wanted. And what I wanted was really very basic. I just wanted to figure out how to do a good job. And I wanted to have a good relationship with the CEO, right? Because, you know, I was working for him and you need to have a good relationship with your boss. But the problem was, you know, in this sort of, in the first firing anyway, was I had not, I had not articulated those goals. And so I shouldn't have been surprised when six weeks into, you know, my tenure at Slack, I came back from my backpacking trip with my batch.

or buddies, and I had an email in my inbox saying, hey, you're fired, right? Like, you know, it seems like it's not working out. Let me know how you want to wrap it up. So, as you can imagine, I freaked out, right? I loved this job. I love this company. So I profusely apologized. I said, you know, I'll do whatever it takes. I'm so sorry. You know, I'm going to be committed to turn this around. And so early stage startup, turns out firing doesn't always stick. Monday morning, I had my job back. but obviously things were not the same as they'd been before because in the second era that what I wanted was sort of better, better articulated more clear. But all of a sudden that fear that had been

under the surface, that insecurity was now very, very present every day because I was terrified, right, of like, you know, was I going to get fired, right? Was I not, you know, make the most of this opportunity? And so, you know, I went fully into people pleaser mode. And so that meant that even though, you know, what I desperately wanted was to have this good relationship, was to sort of, you know, be successful, build a great product. I had a year of one-on-ones for the CEO. I never, never, ever asked for what I wanted. I never said it out loud, right? Because I was scared. You know, I was scared of what the consequences were. I knew there were 100 PMs, you know, standing behind me, ready to take my job. If the CEO is ever, you know, a moment unhappy with me. I said, no, I'm not going to take the risk, right? I'm too scared of what the consequences might be. And so I held all that fear and all those desires. I just want to do a great job.

I want us to be awesome partners and build this amazing industry-changing product. And I never said any of that stuff out loud. I just put my head down. I tried to obey. And so, you know, as you can imagine, right, this didn't work very well, right? Like I was feeling horrible day-to-day. I was terrified of this guy I was working for. And so, again, I shouldn't have been surprised, but I was when I got fired for the second time.

wasn't quite firing, but this time I'd come back from my honeymoon, and I had a phone call on Monday that said, you know, seems like product management's not working out for Slack. You know, we're actually just going to get rid of product. You're going to be user research. It's going to be fine. And for me, you know, I love user research, but that was the beginning of my career. I was not interested in going back to that. And what was fascinating was at that point, I was actually able to articulate what I wanted there and was willing to say it out, wow. Because what I wanted was, no, like, let's keep me in product, right? I've got an idea for how we can run it. So I wrote up a proposal. I sent it around to the management team. Turns out when you actually ask for what you want out loud, you're much more likely to get it. And so within a week, this new plan had traction with the management team. And, you know, I had my old job back again, right? Everything was fine, except, of course, wasn't fine. Because now I was scared, but the stake seemed really high, right? And this is where kind of that deep imposter syndrome sit in. I was like, am I even any good at this?

Like, should I even be in product management? Am I ever going to work in this industry again? Is this going to be my dark secret that I take to the grave that Stuart Butterfield fired me three times, you know? And so, you know, that, what I think what I couldn't be with in that moment was, was the no's, right? Because I was getting no after no after no after no, you know, from, from Stewart and the rest of the management team saying, yeah, like,

what you're doing is not working for us, right? Like, your ass are not landing. Like, you're not being effective in the way that you want to be effective. And because I wasn't able to hear those nose, again, to that emotional regulation standpoint, I just, I couldn't handle the feelings of like, oh, like maybe what I'm doing is not good enough. So instead of pointing the finger of myself, I pointed the finger at him. I said, you know what? Actually, this guy's, he's not such a great manager. He's not so good at product. You know, I'm the one who's on the ground with the users. I know what's right. Against all evidence to the contrary, by the way, is this product, luminary, visionary, famous person, right? So, you know, clearly not based on any facts,

but it was an emotional issue, right? I couldn't deal with the reality of what I was doing was not working. And so again, because, you know, I was not articulating what I wanted. I was not asking for it, and I certainly was not listening to the nose, you know, I shouldn't have been surprised when finally the third time it came down and this time it was serious because we had HR. So it turns out once you hire HR, the fly rings are final. And so I only made it to a year at Slack. And it was a year of just utter torture because I spent that year being fully out of integrity with myself, right? Never saying what I really wanted, how I really felt because it didn't feel safe. I was too scared. I kept it all inside. And it took me six months or a year, even after

that to really feel safe and okay again, right? It was a serious decompression time. My wife and I had a baby during that time. You know, I was on zero sleep. It was a rough, rough period. But, you know, the irony is, is that, like, when I actually came out of that experience, like, the reality of it was extremely simple, right? I hadn't articulated what I wanted. I hadn't asked for what I wanted. I had not listened to the nose in response to my non-ask, right? And so, of course, I was unhappy with the result, right? Like, why would I have expected anything different? I wasn't the victim, Stewart wasn't the villain, right? Like, we were, it was just ineffective asking. And so, to me, especially because I was already on that path towards coaching, that lesson hit really hard,

right, in terms of, like, how do we make this work more sustainable? Right? We stay in integrity with ourselves, even when it's hard, even when it's scary, right? Even when we don't know exactly what the outcome is going to be. And so that's really the story of how I became a coach, right, of seeing exactly how much I'd screwed up at Slack and seeing how much I had suffered and how much a lot of people suffer in these similar circumstances. And all you have to do to turn it around is ask for what you want. So this is why I'm so passionate about this stuff, because it sounds so, it can sound so fluffy to say, oh, you know, focus on integrity, you know, honor, your desires. But no, like, it's real life stuff of like a year of suffering, a pain, of fear,

Right. Like, I don't want, I don't want other people to be going through that. And that's why I'm so passionate about this stuff. Wow. What a story. And I love that it's kind of a microcosm of everything we've talked about. You've kind of did all the things that you teach people to avoid. Exactly. And I think what's interesting is you kind of went through these three phases. Interestingly at the beginning, your first phase was you were not hearing the nose, but it was rooted in this confidence that your founder, you're awesome. They're so lucky to have you. I know what I'm doing. Get out. way. And then the third phase, you also, the issue there was you weren't hearing the nose, but it was more from fear of being fired again. And so it's interesting that there's these different reasons you're not hearing what people are actually saying. Totally. One, and to me, the first one is about articulation as well, because I think that if in the beginning it articulated that, yeah, I'm confident, but I actually, I want to do a really good job, right? And I want to have

good relationships. So let me, let me think about intentionally how do I create those outcomes, right? But because I hadn't articulated, that's what I wanted, right? Like, it didn't even occur to me like, oh, yeah, I need to like do some intentional relationship building, you know, figure out some metrics for success. Because it's an early stage startup, right? Like, there wasn't a ton of sort of process or structure in place, suffice to say. And so if I wanted that, I needed to create it myself. But because I hadn't articulated that any of that was important to me, I just flew by the seat of my pants. And it took failing to get have some data to say, oh, yeah, maybe I need to look at this more closely.

I imagine you've gone through this exercise many times, but say you were to do it again, what would you do differently? And what do you think would have happened? Do you think you would have stayed there for many, many years, been had a product that slack at this point, just imagining that reality, what would you have done differently? And then what would you have imagined have turned out? Well, I mean, obviously broadly, I would have asked for what I wanted, right? And what I wanted was I wanted to do the best work of our life, right? I wanted to have a deep professional partner in the CEO and the rest of the product and management team. And yeah, I wanted to produce great work that people love. Right. And that was part of why I was attracted

to the culture and the mission and the company. And so this is what's tricky, right? Of course, that's what I would have done. Now, do I know what the outcome would have been? No. I might have been fired even sooner, right? Like, they might have said, no, you know, like, this is not working out. Like, let's just, let's just be done here. And so that's what's tricky about this is it really isn't about the outcome, right? Of course, asking for what you want makes you more likely to get the outcome you want, but you don't do it, you know, for guarantee of a certain outcome because no one can promise you that, right? You do it so you can stay in integrity with yourself and not suffer through all this, because at least that I would have said,

you know what, like it didn't work out, you know, at least I'm not sitting here suffering. I can get another job at another startup, right? It's not the end of the world. And I think that mistake we make is pretending that it is, right? Of saying, you know, going into fight or flight and saying this is like a severe existential threat to who I am and sort of my safety in the world versus being like, yeah, I'm disappointed. I wish it had worked out, but it did. And that's a really profound point that you don't, this, this practice isn't necessarily to just have everything work out beautifully and to get the things you're looking for. It's to feel like you did, which you could have, and to feel integrity with yourself

that you did what you needed to do and you're not going to regret something down the road. Indeed. I want to take a quick tangent down the being the first PM route real quick. There's a lot of people that think about being the first PM at a startup, join as the first PM. I imagine you work with people asking for advice along these lines. It's classically a very challenging role.

Many people don't last. Many people follow your trajectory where it's like, Oh, shit. What have I done? Any advice for people that are first PM at a company or startup or thinking about that role? What can you tell them to help them be successful or at least not suffer? To me, it really is about the relationship with the CEO or with the founders because that's sort of the root of a lot of the issues that come out of that scenario. because it's not always you. Like in my story, I think it was primarily about me. But I also work with a lot of founders who are going through a really tough things. My clue to people who report to a founder is to say, imagine if you're confused about how your founder is behaving, imagine that they're terrified all the time, right?

And see if that makes their behavior more clear. Because it is scary to be a founder, right? Everything's on your shoulders. I think a lot of people do feel that sense of high stakes all the time. And so, you know, I think being real about that, if like what is the state that the person or the people you're working for are in and sort of working within that versus sort of pretending that it's something else or wishing that it were something else is sort of the path to having a healthy relationship.

Because if you don't have a healthy relationship with the person you're working for, you're not going to get anything done. You're not going to succeed in any meaningful way. I love that framework of how to think about why a founder is behaving in a certain way. just maybe a last following thread there is just what what should people look for to help them understand if the founder and them are a good fit if they're going to have a good time working with that founder is anything just like questions they might ask or ways of operating that are useful to understand like okay I think I'll be okay with this

founder in this in this company as the first PM or not I think it's a hard thing to generalize about but to me it really is about understanding expectations right if like what do you you know I mean I guess this is a predictable coming for me, but what do you really want? Right? Because I think that often, you know, the founders put together a job description, but then they're faced with a real human being who has real sort of human subtleties and things they're good at are not so good at. And so being very, very clear about expectations and of figuring out collaboratively a way to work together that's effective to me is, you know, the close, there's no guarantees, of course, but it gives you

a sort of more sure path to having a productive relationship. And it's actually something that I recommend to a lot of founders for maybe their first, you know, 10 or 15 or 20 employees of just have like a relationship design conversation with each of them when they're first hired. Because I think a lot of us come in naive the way I did, assuming, oh, yeah, I'm just going to come in and kind of do my thing the way I've always done it is going to be fine versus coming in and saying, I actually don't know how I'm going to operate at this company, right? I have range like anyone has range, and I don't know what this company needs and who else is here and sort of what my role and what my place is going to be within these other people. And so by really

understanding that intentionally and not from a place of performance management, you're already doing this poorly, you're in big trouble, but a, yeah, what is the best way to work together, given who we have now and what we want, what we need? Let's figure it out. Coming back to our core topic, is there anything that we didn't cover, anything that I should have asked you about the skill, the art of asking for what you want. Anything else you want to leave listeners with? I do want to mention something that I hear a lot from founders when I talk about the piece of working through resistance. Because I think a lot of them say, oh, you know, you want me to let go of fear and focus on what I want. Well, I mean, I've been running from fear my whole

career. Like, that's how I'm so hardworking and how I'm so smart is I'm always afraid I'm not good enough. Like, is, you know, am I going to be able to do this job without fear hounding me every step of the way? And I just, and I just remember the first time I heard this, it broke my heart. And now I've heard it, you know, dozens of times, I'd say. So, I mean, it really is, I think it's a belief that sits deep in the hearts of a lot of us high achieving Silicon Valley tech types of, you know, my fear of not being good enough is what drives me to be great. And I just want to come out here and say, there's other ways to motivate, right? You can motivate based on joy, based on vision, based on, you know, your, you know, inspiration in this vision of what

you want. And, you know, I think a lot of folks I talk to are skeptical, understandably, because they've, they've operated a different way their whole life. And all I can really say is try it, right? Try following an inspiring vision that's really meaningful to you and just see what it's like to not be sort of living in fear all the time because it is, it's a big difference. And it's really meaningful. It matters a lot. So is the idea there is the fear there that if they ask for what they want, they'll get what they want and they let go of kind of this drive to prove themselves. And is that the fear?

Like, how is it that they move away from that need to prove themselves? Well, I mean, that's a longer story. I would say, you know, sort of, you know, managing our own fear as a sort of lifelong practice. I'm not going to claim I'm anywhere near done with it. But I guess I just say that I think part of the big shift I see in personal development for people I work with is from saying, oh, no, my fear is good. I need it. It's keeping me safe to saying, you know, fear is for when there's a tiger chasing you and there's no tiger chasing me. I'm sitting in my office in a desk chair on a Zoom call, right?

like there's no real danger here. And so fear is not particularly functional. And so when they start realizing that, the practice becomes, oh yeah, I'm feeling afraid, but I'm reminding myself, there's not a tiger in the room. Like if I really want to sort of get things done, achieve my goals, I need to focus on vision on what I want to achieve in the world, not on avoiding all these fears. So that's the short of it. Amazing. It reminds me we have a chat, I had a chat with Matt Mashari, and we spent a bunch of time on dealing with fear and overcoming fear. So folks want to dig deeper there. They could check out that episode.

Okay, just maybe one more question before we get to our very exciting lightning round. I want to take us to Contrarian Corner. Classic contrarian Corner. I'm curious if there's anything that you have a contrarian opinion about, something that you believe that most other people don't. For me, I'm not a big believer in discipline. you know, that I think, you know, some folks come to coaching looking for, you know, sort of a drill sergeant to say, all right, shout at me and tell me to do better. And I sort of say, yeah, no, that's not how I operate.

Because it's not the discipline doesn't work, right, but it's like people pleasing. It's a short-term, it's a short-term coping strategy. Like discipline will get you in the gym for a week, but it's not going to get you in the gym for a year, right? The people who are in the gym for a year are doing it because they want to, right? there's actually something that's motivating for them in that, that's not just, oh, I hate this, but I'm going to go anyway. And so, you know, I try to be really clear with people about that, that I'm not going to be the drill sergeant because it's unsustainable, right? Like someone shouting at you, like is not going to, you know, get you sort of moving towards what you want in life over multiple years, right? It's a days or weeks or even hours thing. And so I really look for a higher bar to say,

yeah, like let's look for true long-term sustainable motivation, which means relying on vision, pursuing what you want. I love that it all ties back to knowing what you want, asking what you want, and then dealing with the answers that you get. I am a broken record, admittedly. Amazing. Kenneth, is there anything else you wanted to share or leave listeners with before we get to a very exciting lightning room?

No, but just thank you for letting me share this stuff. It really is my life's work, and I'm very passionate about it. and I hope it's helpful for people. And I'm going to be writing more about it on LinkedIn. Okay, amazing. We'll point people there. With that, we've reached our very exciting lightning round. Are you ready?

I'm ready. Let's do it. First question. What are two or three books that you've recommended most to other people? Well, I already mentioned radical candor. I think that is for sure a modern classic. And I think that that whole idea of sort of challenging directly, but caring personally is very much aligned with what I'm talking about.

right, because you know, you need the relationships and you need to actually speak your truth. So I love, you know, Kim Scott's writing on that stuff. We had a Kim Scott on the podcast. If folks want to dig deeper there. We'll link to that episode. I'll let you keep going. Sorry for the interruption. Yeah.

You have, I mean, I mentioned before, but I actually took Johnny Miller's nervous system mastery course. I just wrapped up. So you've had lots of great personal, professional development thinkers on the pod. So thank you for introducing you to them. I'm so happy to hear that. We'll link to that episode as well. I love that.

What a circle of life we've got here. Guests following other guests, taking their courses, joining the podcast. What a happy world. Yeah, indeed. Okay, any other books before we move on? I also love the 15 commitments of conscious leadership. So I'm pretty sure other guests have mentioned that as well. But to me, part of why I like that is that I think a lot of personal development books

are not very directive. They say, oh, you know, just dig deeply and find your truth. And while there is value to that, of course, I think sometimes it's nice to have some direction of, yeah, here's 15 things that like generally your life's going to be better if you do them. And so I, to me, it's a nice balance of embracing the really deep stuff of how to live a good life and be effective in the world and be really directive. Like, yeah, try this stuff. It works. Do you have a favorite recent movie or TV show you've really enjoyed? I'm a, I'm a recent tenet. I'm a recent ten fanatic. So it was one of the things I picked up during the pandemic. So I really enjoyed Netflix's breakpoint because it's a documentary on the best tennis players in the world. And it is just,

I just find it so, I don't know, it's just beautiful seeing how everyone is kind of the same, because all these people, they all know all the strokes perfectly. Like they're technically perfect in pretty much every way. And so it really is mental, right? For those folks, it is about working through resistance as well, right? When they have a narrative that says, oh, I'm behind, the other person's better, you know, I'm not going to be able to do this, right? Are they believing that? Or are they working through that resistance and saying, you know, that's just a story I have?

I actually don't know what's going to happen, but I'm going to try to win. I love it. You see coaching opportunities in everything, even entertainment. I also love, I mean, actually, you know, speaking of that, I mean, it's almost too on the nose, but there's this movie Living from a couple years ago, this British actor who's this sort of, you know, he's this sort of, you know, tough, old sort of, you know, stodgy government office manager,

and he gets diagnosed with cancer. And he has this real transformation where he thinks about, God, I've just been sitting in an office filing papers my whole life. What do I actually want to do with the last months of my life? And he builds this playground for children, and that's actually his legacy. Sorry, actually. Spoiler alert.

Whoops, Shunif. You mentioned tennis and you mentioned British people. I will actually be at Wimbledon this year in London with my dad in July, and we're going to host a meetup there while I'm there. Just for anyone listening right now, just to give you a heads up. Awesome. How fun is that going to be? Okay, next question.

Do you have a favorite product you recently discovered that you really love? Well, you know, it's funny. I used to be a big wine aficionado, and I think as with many of us, I am discovering I feel better with less alcohol in my life. And so one of the things I've been picking up is uh, uh, uh, uh, uh, uh, uh, uh, uh, uh, uh, uh, uh, cup of Taiwanese Wencheng Bao Zhang in front of me. And, um, I feel like it's like all the nerdery that I put into wine of like regions and varietals and history and processing, but it's actually good for me. It's like full of antioxidants and makes me more focused and I can drink it during the day. And so yeah, I've been totally going down

a nerdy tea rabbit hole. And I recommend it. Taiwanese mountain teas, especially. I got to give me some of that. That's actually, I always have tea here when I'm doing these podcasts. I'm a less sophisticated tea drinker. I just go with Earl Grey, but like a really nice Earl Grey. And so I'm going to have to buy some of this. Do you have a place in a brand you recommend most? There's lots of, there's lots of great stores online. You can check out tea from Taiwan.com. That's a good one. They're going to get a bunch of traffic. They're like, what the hell just happened?

T from Taiwan.com. Amazing. Do you have a favorite life motto that you often come back to, find useful, share with work, share with friends or family and work or in life? I mean, I'm pretty sure you can get us, sweaty. I wonder what it might be. I wonder what it might be. So this is actually part of why I started writing this book is because my friends were

be annoyed with me, you know, telling them, have you asked for what you wanted, right? Ask for what you want. Because, yeah, it's the best advice I have is to ask for what you want. It all just comes back to that. Final question. We've been talking a lot about asking for what you want. Kenneth Berger, what do you want? Ooh, all right.

Well, you know, I think for me, you know, Lenny, you are already, you know, industry luminary with, you know, thousands of followers. I am, I'm interested in, and sort of sharing more of these ideas. So if y'all would come follow me on LinkedIn and subscribe to my newsletter, I'm going to be exploring these ideas and sharing more of this stuff because I just am so passionate about it. And yeah, I'd love if you'd come and join me in that journey, bring questions and ideas. And I'd love to talk about this stuff because I, I just find it endlessly interesting. But you're working on a book along these lines at some point that will come out. That's right. That's right. So, yeah, so I'm working on it in book form, but part of what I've been doing is I realize I want to work on it in community, right?

Speaking of asking of what you want, right? I mean, for me, it's not just about my vision and my framing, but like I'm a coach, right? Like, I'm not just about big ideas. I'm about making a difference from my clients. And so I realize, yeah, if I really want to make a difference with people, I need, it's like a product. I need to get out in the world and test out these ideas and see what lands with people and what's effective for them and what works. hear the stories and sort of really get into it. So that's kind of why I've been putting myself more out there. Amazing. So kind of along those lines, two last questions, where can folks actually find you online and follow the stuff that you're writing? And how can listeners be useful to you? So you can find me on LinkedIn.

I'm Kenneth Berger, B-E-R-G-E-R. So please follow me there. Subscribe to the Ask for What You Want newsletter. And yeah, you can check out my website, K-Burger.com, K-B-E-R-G-E-R. K-B-B-B-B-R. Kenneth, you're amazing. Thank you so much for sharing so much wisdom with us. I think we've helped a lot of people. Thank you for being here. Thank you. Bye, everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at Lenny's Podcast.com. See you in the next episode. Thank you.