Why not asking for what you want is holding you back | Kenneth Berger (exec coach, first PM @Slack)

1. 0:00 – 4:31

   Kenneth’s background

   1. LRLenny Rachitsky0:00

      You were famously the first PM at Slack and then you ended up transitioning into executive coaching.

   2. KBKenneth Berger0:05

      For me, the impact was about making this work sustainment so that we're not burning out or selling out, but actually able to pursue these hard goals that we have in startups.

   3. LRLenny Rachitsky0:14

      What we're gonna be talking about today is your personal magnum opus, the output of 10 plus years as a founder and operator and seven plus years as a coach. The core idea is...

   4. KBKenneth Berger0:24

      Ask for what you want. Turns out when you actually ask for what you want out loud, you're (laughs) much more likely to get it.

   5. LRLenny Rachitsky0:30

      You're hired. How do you know that this is something you need to be working on?

   6. KBKenneth Berger0:34

      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 freak camp, maybe you're used to ordering people around and saying, "Go do this now."

   7. LRLenny Rachitsky0:44

      How do you know what you want?

   8. KBKenneth Berger0:46

      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.

   9. LRLenny Rachitsky0:59

      (instrumental music) 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 Berger after a short word from our sponsors. 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 our product called Sidebar. The best way to level up your career is to surround yourself with extraordinary peers. This gives you more than a leg up, it gives you a leap forward. This worked really well for me in my career and this is the Sidebar ethos. When you have a trusted group of peers, you can discuss challenges you're having, get career advice, and just gut check how you're thinking about your work, your career, and your life. This was a big trajectory changer for me, but it's hard to build this trusted group of peers. Sidebar is a private, highly vetted leadership program where senior 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 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. 93% of members say Sidebar helped them achieve a significant positive change in their career. Why spend 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/lenny. That's sidebar.com/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 Orangetheory trust Webflow to achieve their most ambitious goals today at webflow.com. Kenneth, thank you so much for being here. Welcome to the podcast.

   10. KBKenneth Berger4:23

       Yay! Thanks for having me.

   11. LRLenny Rachitsky4:25

       (laughs) I love that. Yay! We should, that should be a tradition that everyone (laughs) goes with... I love that.

2. 4:31 – 6:36

   The importance of asking for what you want

   1. LRLenny Rachitsky4:31

      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 gonna 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?

   2. KBKenneth Berger5:19

      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 how to ask 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, is sort of the reason that the stakes around asking for what you want are so high because yeah, you know, if you're... We can't guarantee we're gonna get what we want, but if we're asking for it regularly, if we're listening to the response, we're respecting the nos 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 towards what I want. 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, of what's, what's, you know, important in sort of achieving our purpose.

3. 6:36 – 8:09

   Challenges that arise when people struggle to ask for what they want

   1. KBKenneth Berger6:37

   2. LRLenny Rachitsky6:37

      What are 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?

   3. KBKenneth Berger6:47

      For me with clients, I think, what I'm often looking for are, is kind of this 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, right? 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, uh, 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, 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 on my report. You, you better, 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, it's a obvious source for a lot of issues.

4. 8:09 – 9:17

   A personal example of failing to ask for what you want

   1. KBKenneth Berger8:09

   2. LRLenny Rachitsky8:09

      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, where you didn't ask for what you want?

   3. KBKenneth Berger8:19

      There's so many examples, you know, I, I think, you know, we'll, we'll eventually get into the, the story of how I was fired from Slack, but, um, I think for me, you know, the, 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 of 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've, you know, 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, right? 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, right? There's no, there's no way to have that conversation respectfully.

5. 9:17 – 10:49

   Signs this is a skill you need to work on

   1. KBKenneth Berger9:17

   2. LRLenny Rachitsky9:17

      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 Kenneth'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 with people. Are those the two answers? Are there more?

   3. KBKenneth Berger9:38

      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 founder, right? Of, okay, normally, you know, when I was at Adobe, it's a big company, you know, they're gonna be fine either 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 idea, 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-

   4. LRLenny Rachitsky10:25

      Mm-hmm.

   5. KBKenneth Berger10:25

      ... than on actually achieving what we do want, right? And that's a really critical distinction, right? Because, you know, if we're, if we're running away from our fears, it doesn't necessarily mean we're getting anywhere meaningful for, for what our desires are. And so that, that sense of high stakes that often we can get, whether it's in interpersonal conflict or being afraid of asking for what we want, that can get us really focused on the fears rather than focused on the goals.

   6. LRLenny Rachitsky10:48

      There's

6. 10:49 – 15:28

   How to get better at knowing what you want

   1. LRLenny Rachitsky10:49

      a question I was gonna save 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?

   2. KBKenneth Berger10:57

      Mm-hmm.

   3. LRLenny Rachitsky10:57

      There's basically knowing what you want and then asking for what you want.

   4. KBKenneth Berger11:00

      (laughs)

   5. LRLenny Rachitsky11:00

      And I often... I'm like, I try to... I'm like, I, 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? (laughs)

   6. KBKenneth Berger11:27

      Well, first of all, I'd say you're, 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, 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 to me? So, you know, one of my favorite techniques here is, is this concept they call the, the dream behind the complaint, because you, 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, are we like, 'Oh, uh, you know, my, my dream is that, you know, I get to speak up a little more in meetings.'" It's like, well, that's probably, 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 in 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."

   7. LRLenny Rachitsky13:25

      (laughs)

   8. KBKenneth Berger13:26

      And they sort of say, "Uh, I don't know if that's quite my dream (laughs) ," 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, that checking whether it actually feels inspiring but also sort of credible and possible is a good way to sort of find that middle ground, where like, "Yeah, this dream is, is hard. I don't know if I'm gonna get it, but damn, it's worth trying," right? "Like, I want to go for it."

   9. LRLenny Rachitsky13:54

      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?

   10. KBKenneth Berger14:10

       For, you know, specifically for articulating what you want, 'cause that's kind of the first step of, 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? 'Cause it's an iterative process, right? We're learning from the response and what it tells us, 'cause the response is usually no. And so really what tends to be hard there, I mean that's a straightforward process. It's, you know, not rocket science. What's hard there is the resistance, right? The parts of us that are not so excited about that, that thinks asking for what we want is scary and articulating a big dream that we might not get is, is really scary, 'cause god, what if I don't get it? What does that mean about me? Am I a failure, right? Or, you know, what does it mean if I respect the no? Like, what if I ask for my big dream and someone tells me I'm not gonna get it? Like, what does that mean? How am I gonna feel? And so working through all that resistance is really a lot of what tends to be tricky about asking for what you want. Because otherwise it's, yeah, articulate, ask, accept.

7. 15:28 – 17:29

   Why hearing “no” is a normal part of the process

   1. KBKenneth Berger15:28

   2. LRLenny Rachitsky15:28

      Okay. Uh, you're, you're getting into where we're gonna go. Before we get there, final question. This idea of dealing with no. I think this is the other big blocker for people is like, "Oh, 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, this fear of just like asking for what you want?

   3. KBKenneth Berger15:49

      So I, I, I have a more expansive definition of no tha- 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. Kinda. I'll try. You know, we'll see," but a, "Yeah. Absolutely. Let's do this," right? And, 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, to bite us later on because we accept this thing that's short of a hell yes. And then we realize 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, by, you know, May 1st,'" and then May 1st comes and surprise, surprise, you know, your milestone is not done, right? Because you didn't, you didn't sort of go for that, 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, right? 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 gonna try next? What are we gonna try next, try next, try next? 'Cause that's what's gonna 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, what would be a hell yes day for you? Where you 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." Um, so, but let's get to a hell yes. What would it take for us to get there?

8. 17:29 – 19:20

   Getting a “yes” vs. a “hell yes”

   1. KBKenneth Berger17:29

   2. LRLenny Rachitsky17:29

      That's a really helpful framework and, and phrase to use, is just what would it take to get to hell yes. Not just what would it get- 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.

   3. KBKenneth Berger17:45

      Yeah.

   4. LRLenny Rachitsky17:45

      Oftentimes people kind of like, "Yeah, yeah, yeah, yeah," and then they don't actually follow through.

   5. KBKenneth Berger17:49

      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?

   6. LRLenny Rachitsky18:02

      Mm-hmm.

   7. KBKenneth Berger18:02

      When all of you is fully in and ready to do this.

   8. LRLenny Rachitsky18:06

      And this applies to... You're giving examples here of just like getting h- like aligning a deadline-I imagine this same skill applies to everything you in life, like relationship questions and friends and family and work.

   9. KBKenneth Berger18:19

      It does. And I, and, you know, it is something universal but I, I do think of it as being particularly relevant to my work with startups 'cause, you know, I work primarily with startup founders because with startups, you know that mostly they fail, right? 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 gonna sort of operate in the startup world of being okay with not knowing that you're gonna get the outcome that you want, right? You know, a lot of people, we operate in a safer world where we're more clear exactly what the outcomes are gonna be, but if you're a startup founder, you gotta be okay with, "I'm just gonna go for this and I know I probably won't get it, but it's so meaningful to me, I'm gonna 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 gonna get it. I know I'm not guaranteed to get it. I'm not gonna be attached to that. I know people aren't obligated to tell me yes but I'm gonna go for it anyway, right? Because I want it and that's enough."

9. 19:20 – 24:07

   Step 1: Articulate what you want

   1. KBKenneth Berger19:20

   2. LRLenny Rachitsky19:20

      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.

   3. KBKenneth Berger19:31

      So, the first step is articulating what you want, right? And we've sort of gone into this a little bit, but to me, I think the, the key places that people tend to sort of, uh, have missteps here are one in, one in this phrase, "It's fine." I think of the, it's Fine cartoon with the flames-

   4. LRLenny Rachitsky19:47

      Mm-hmm. (laughs)

   5. KBKenneth Berger19:48

      ... you know? Um, a- a- and you know, and the, and the dog, I think it is, but-

   6. LRLenny Rachitsky19:51

      Mm-hmm.

   7. KBKenneth Berger19:51

      ... I think a lot of us fall into that trap of saying, "You know what? I, I'm fine. I actually, I don't need, I don't need anything. I'm good." And again, this is tempting, right? 'Cause 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 it's, yeah, like, 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 them to do is to really tune in to the parts of them that maybe aren't so fine. They're like, "Gosh, I, I'd really, you know, I'd, I'd 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 kinda, 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, uh, uh, ar- articulate these sort of, you know, wildly unrealistic goals. 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 this, for those folks, it really tends to be more about saying it out loud 'cause 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? Like, 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, emotional goal of, "You know what? I just want to have a team that feels really aligned around me and like, 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 respe- 100% aligned in everything. But it does mean there's a certain feeling that I have when I go into work, even though I don't know that we're gonna get what we want or that everyone's going to agree.

   8. LRLenny Rachitsky21:47

      Do you have any examples from your time you could share of someone articulating what they want and figuring out how they articulate, how to articulate what they want just to make it even more real?

   9. KBKenneth Berger21:58

      To me, a lot of the classic examples are around feedback, right? Because, you know, I, I, 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 del- deliver negative feedback and even more to actually create consequences because the thing about accepting other people's nos 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, you know, aligned with the culture or they're not sort of delivering the way that, you know, the, the, the CEO wants them to be delivering because it doesn't seem that nice. They're like, "Oh, I think of myself as nice and, and of, and of being so kind and of people loving me." And it's like, well, that, 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, those choices.

   10. LRLenny Rachitsky23:05

       Can you even get more concrete there? Is it like, "We need to hit this date or there's gonna be big problems." Or is it like, "I need you to hire this large of a team." I don't know. Like, what, what is it that they, they're not articulating that they later realize, "Oh, here's what I need to articulate"?

   11. KBKenneth Berger23:19

       So I think sometimes, it is about alignment, right? The disagree and commit. So I see-

   12. LRLenny Rachitsky23:24

       Mm-hmm.

   13. KBKenneth Berger23:24

       ... that a lot, right? Of like, you know, a 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, 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.

   14. LRLenny Rachitsky23:52

       That's an awesome example. I fully get that and I could see how many people are not... Or, uh, 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 'cause it's gonna, I think, upset people.

10. 24:07 – 26:56

    Doing an integrity check

    1. LRLenny Rachitsky24:07

    2. KBKenneth Berger24:07

       Yeah.

    3. LRLenny Rachitsky24:07

       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- I'd h- be happier or things would probably run better. That's a really c- that's a really cool example of how to think, do that 'cause that's easy just like, oh yeah, if we, like, actually could make a decision in this meeting, that'd be really cool.

    4. KBKenneth Berger24:33

       (laughs)

    5. LRLenny Rachitsky24:33

       Maybe we should try to do that and ask for that. Uh, is there any other tips and uh, approaches to helping you figure out what you want?

    6. KBKenneth Berger24:40

       It always comes back to integrity, right? And a great way to sort of do an integrity check is just look for, have I fully expressed myself, right? And so I think we've talked a little bit about sort of charting your feelings as a piece of that of like, yeah, am- 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 owned those feelings and expressed 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? Of, 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 wanna say this to this person, right? At this point you're probably out of integrity 'cause 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 'cause it is about checking for all these things like, yeah, like what is- what is the part of me that's not fully expressed because it doesn't mean I'm gonna get what I want or that people are gonna, you know, sort of, you know, gi- give me all my dreams immediately, but it feels so much better to have it out, right? That- 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."

    7. LRLenny Rachitsky26:02

       (instrumental music) This episode is brought to you by Vanta. When it comes to ensuring your company has top-notch security practices, things get complicated fast. Now you can assess risk, secure the trust of your customers and automate complaints for SOC 2, ISO 27001, HIPAA and more with a single platform, Vanta. Vanta's market leading trust management platform helps you continuously monitor compliance alongside reporting and tracking risks. Plus, you can save hours by completing security questionnaires with Vanta AI. Join thousands of global companies that use Vanta to automate evidence collection, unify risk management and streamline security reviews. Get $1,000 off Vanta when you go to vanta.com/lenny. That's V-A-N-T-A.com/lenny.

11. 26:56 – 30:45

    Step 2: Ask for what you want intentionally

    1. LRLenny Rachitsky26:56

       Okay, this is a great segue too. Okay, now I have a sense 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?

    2. KBKenneth Berger27:12

       So for- 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, right? 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- and- and just magically knowing what you want, right? And if you're sort of more in the control freak 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 e- any of them, right? Like, is this working for you? Like they'd say no, right? Of course, it's obvious, like 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 gonna 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, not 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- we sort of tend to tell ourselves the story, "Oh, this is fine. I'll be fine." Uh, versus owning like, "I'm gonna- I'm gonna be living my life like not- 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.'" (laughs) Right? Like that's- that's not what we want people to say at our eulogies.

    3. LRLenny Rachitsky29:01

       No. (laughs) That's, uh, 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, um, advice for maybe phrases of how to approach? You talked about making it intentional. How do you actually go about doing that? Is it like the way you've communicated it? Is it something else? How do you actually do this without pissing people off and also just like risking too much?

    4. KBKenneth Berger29:31

       Well, and so- so, so th- that even implicit in that question, right? Like there's to- to me- to me that's that- 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 it's gonna 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 gonna get the outcome we want. We say, "Oh, well I'm not willing to ever piss anyone off ever and so I'm just gonna be stuck at this step because like I haven't figured out what's gonna guarantee me." And of course there's no guarantee. We can never guarantee that people are gonna feel a particular way-And so part of, 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 gonna be effective, and no one's gonna be mad at us, and we're gonna get all of our dreams come true. But yeah, no, 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?

12. 30:45 – 34:48

    Understanding your influence

    1. LRLenny Rachitsky30:45

       Such a good point, uh, about what you identified and how the way I, I think about it and the way I think a lot of people I think about is just like, how do I su- do this without causing anyone any, any pain or risking anything going wrong? But that's, to your point, part of it. (laughs) 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, ICs on teams, other functions that don't have, you know, "power." 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?

    2. KBKenneth Berger31:23

       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 gonna go. I'm not gonna 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 gonna 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?"

    3. LRLenny Rachitsky32:00

       That's such a great approach. It's like very not scary to say that. It, it also, I think highlights something I wanted to touch on is, I think people have a lot more s- influence and power than they think they do. Say a PM on a team disagrees with a, a plan for a product. Like, people actually care about your opinion.

    4. KBKenneth Berger32:23

       Yeah.

    5. LRLenny Rachitsky32:23

       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?

    6. KBKenneth Berger32:34

       You're actually, you're giving me deep goosebumps because this is... I, I, I think this is, this is a really underappreciated thing in terms of asking for what we want because especially in the PM world, we're trained to look for data, right? We're not just gonna state an opinion. We're gonna 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, uh, 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, 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 gonna 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 and I'm just gonna 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."

    7. LRLenny Rachitsky33:50

       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, like, "I shouldn't say anything 'cause 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."

    8. KBKenneth Berger34:03

       Totally. Well, and, and, you know, I think there's a balance there as with anything, like is, is ignoring data and going in gut all the time great? Probably not, right? (laughs) We, we, we use data for a reason. Um, 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 said out loud, and I think often the dangers of, of, is- 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 gonna agree with me, so I'm just not gonna say it." And so we don't have the data of all those gut opinions of these subject matter experts in the room, right? Even though that gut information to me is just as important as anything we could get from, you know, the SQL database or whatever.

13. 34:48 – 36:24

    Using complaints as inspiration

    1. KBKenneth Berger34:48

    2. LRLenny Rachitsky34:48

       Before we move on to step three, you already, you talked about the, kind of the opposite of asking for what you want, which was just step two, is just complaining and being angry later.

    3. KBKenneth Berger34:55

       (laughs)

    4. LRLenny Rachitsky34:55

       Like, "I knew this project was gonna fail. I knew this was a terrible deadline. I knew this design was not great." Anything more you wanna say ag- along those lines of just like, if you're not asking for what you want, you sh- complaining is often a sign that you're, you should be doing that more?

    5. KBKenneth Berger35:11

       To me, complaints are great inspiration. Um, and so I think the, you know, to, to me, you know, like I love radical candor for example, right? You know, where, 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, and so I think that to me it's all about the effective framing that, you know, the, the complaint is probably not gonna 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 in 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, right? Like, "Oh, like I don't like that whiny part of myself, like I'm just gonna push that one down," versus actually taking what it has to say as important data.

14. 36:24 – 38:00

    Internal family systems

    1. LRLenny Rachitsky36:24

       That's a really good, uh, point. I think that's actually another blocker for a lot of people is just, "I don't wanna be a complaining person."

    2. KBKenneth Berger36:31

       Mm-hmm.

    3. LRLenny Rachitsky36:31

       "I just wanna be like, let's do this. I'm in. Let's go. Let's da. I don't wanna be seen as a squeaky wheel." Is there anything you say there about, as a resistance point for people?

    4. KBKenneth Berger36:40

       Well, I- I- I'm, I'm a big fan of, uh, internal family systems, which is the sort of psychotherapy technique that really talks about parts and, 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, 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 gonna 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, and they're gonna 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

15. 38:00 – 41:24

    Giving feedback

    1. KBKenneth Berger38:00

       an experienced professional."

    2. LRLenny Rachitsky38:01

       Man, there's so many threads we can follow here. This whole line of what internal family systems, right?

    3. KBKenneth Berger38:06

       Mm-hmm.

    4. LRLenny Rachitsky38:06

       That's a, that's its own podcast episode potentially and then imposter syndrome. We've touched a, a bunch of different podcast episodes, but I'll avoid going in that direction. Something you reminded me of is, uh, we just had Carol Robins 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.

    5. KBKenneth Berger38:29

       I took one of Stanford's, uh, 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, 'cause it, uh, 'cause T Group's already people rave about them, but having it at that point in history-

    6. LRLenny Rachitsky38:50

       Mm-hmm.

    7. KBKenneth Berger38:50

       ... with those people in the room, oof. (laughs)

    8. LRLenny Rachitsky38:53

       A lot of tears, I imagine.

    9. KBKenneth Berger38:54

       It was, it was, it was crazy. I mean, it was really wild.

    10. LRLenny Rachitsky38:58

        I feel like every single person that has gone through, I think it's called Leaders in Tech is the broader umbrella term, and Carol talked about it. Everyone that has gone through it, 100% have told me that it's a transformative life experience for them.

    11. KBKenneth Berger39:10

        Yeah.

    12. LRLenny Rachitsky39:10

        And so, and you had a, you had a bonus transformational piece. So anyway, if people wanna check out that episode, uh, we'll include 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-

    13. KBKenneth Berger39:23

        Mm-hmm.

    14. LRLenny Rachitsky39:23

        ... where people can receive it that I'll just highlight here. I have it here, and it's, it's somewhat related to nonviolent communication, which is what you touched on, and she told me actually she, uh, taught this way before nonviolent communication came out with their whole philosophy. And it's basically when you wanna give someone feedback, the fr- 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, uh, do you find that sort of approach helpful?

    15. KBKenneth Berger40:01

        I do. I, I teach the same thing and yeah, I think, you know, sort of-

    16. LRLenny Rachitsky40:04

        Great.

    17. KBKenneth Berger40:04

        ... Carol's approach and, and nonviolent communication.

    18. LRLenny Rachitsky40:07

        Great.

    19. KBKenneth Berger40:07

        Uh, DBT teaches a, a similar approach they call DEAR MAN. Um, to, to me-

    20. LRLenny Rachitsky40:13

        What's, what's DBT?

    21. KBKenneth Berger40:14

        Uh, it's, uh, dialectical behavioral therapy. It's, it's related to CBT.

    22. LRLenny Rachitsky40:18

        Mm-hmm.

    23. KBKenneth Berger40:18

        Um, so there's, there's kind of rough consensus, you know, in, in the sort of personal development world of how to, how to ask and really what they have in common is around kind of staying really factual because, you know, I, I think that, you know, what can we know factually? Well, we can know our thoughts. We can know our feelings 'cause 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 had mentioned of, you know, "I feel like you're an asshole." Right? (laughs) It's like, "Well, that's a story. That's not a fact."

    24. LRLenny Rachitsky41:07

        Yeah. That, I feel that is not the right way to say, "I feel."

    25. KBKenneth Berger41:11

        (laughs)

    26. LRLenny Rachitsky41:11

        What do you actually feel? Yeah. Okay, so let's move to step three. I've been, we've been going on this whole tangent of therapy and stuff, which was amazing, but let's make sure we cover all three steps. So step one again was articulate what you want.

16. 41:24 – 45:22

    Step 3: Accept the response

    1. LRLenny Rachitsky41:24

       Step two is ask for what you want. What's step three?

    2. KBKenneth Berger41:28

       So to me step three is actually the trickiest for most people.

    3. LRLenny Rachitsky41:31

       Mm.

    4. KBKenneth Berger41:32

       Um, and so st-

    5. LRLenny Rachitsky41:33

       So far they're all tricky to me.

    6. KBKenneth Berger41:34

       Oh yeah, they're all, they're all tricky for sure.

    7. LRLenny Rachitsky41:36

       The most tricky, okay.

    8. KBKenneth Berger41:38

       But step three is accept the response.

    9. LRLenny Rachitsky41:41

       Mm-hmm.

    10. KBKenneth Berger41:41

        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, 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, mm, like that's a no, it doesn't matter what comes out of their mouth, right? (laughs) And so the, the challenge of accepting the response is often that of, you know, of hearing the no but not over accepting or under accepting it because I think sometimes what, what people who are really afraid to ask will do 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 gonna 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 now, 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, and a different time. And on the flip side, right, in that sort of more control freak mode, I think for them, they'll, they, they'll often sort of kind of skip over the response, saying, "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 a bad relationship. And so, really accepting the response is about, yes, I'm gonna be genuine about what I want, but I'm also gonna genuinely care about you and have deep respect for your, y- your sort of, you know, 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 nos, right, it actually... It can actually be more influential, mo- more motivating, right? If someone says, "Okay. No. I'm, I'm not gonna... I'm not ready to deliver this on time," be like, "Okay. Well, I'm gonna 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. Hmm. Maybe I can get it done by that time." Right? And so, that way, you're not forcing them and you're not coercing them, right? You're just saying, "No, you said no. So, that your no is no, and I accept that."

    11. LRLenny Rachitsky44:01

        So, s- it feels like part of the skill here is preparing... is, like, knowing some people just say no, and that's okay. Like, you're... That's part of the experience. Uh, part of it is, it... There's this, like, not yet component. Uh, we had, uh, Mihika Kapur on the podcast. She was a PM at Figma-

    12. KBKenneth Berger44:16

        Yeah.

    13. LRLenny Rachitsky44:16

        ... and she had this really, uh, great approach to being... to building new things within companies is just like, everything to her is not yet, and no is a not yet. And the way you phrased it is it could just be the way you ask. 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, uh, it's not no forever?

    14. KBKenneth Berger44:36

        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 no, right? And if it's no, which it probably is, 'cause most of the time the world tells us no, then the question is, all right, what can I learn from this? What am I gonna 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 for, 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 no, right? 'Cause 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 gonna hear no all the time, and that's completely normal and fine. It doesn't need to be something so scary or

17. 45:22 – 57:30

    Kenneth’s experience of being fired three times from Slack

    1. KBKenneth Berger45:22

       awful.

    2. LRLenny Rachitsky45:22

       Easier said than, than done in real life. Is there an example of either a client of yours... 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, or your own career?

    3. KBKenneth Berger45:38

       I gave a talk about this, you know, 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'd just gotten 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 'cause I had 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. You know, I was gonna be going away on a bachelor backpacking trip, you know. I had a 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 gonna 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, to Slack. You know, they'd 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 nos, 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 bachelor buddies, and I had an email in my inbox saying, "Hey, you're fired." Right? Like, you know, "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 loved this company. So I profusely apologized. I said, you know, "I'll do whatever it takes. I'm so sorry." Um, you know, "I'm, I'm, I'm gonna 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 kind of 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 gonna get fired, right? Was I gonna 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 be sort of, you know, be successful, build a great product, I had a year of one-on-ones with the CEO. I never, never, ever asked for what I wanted. I never said it out loud, right? 'Cause 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 was ever, you know, a moment unhappy with me. I said, "No, I'm not gonna 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 of like, "I just wanna 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 and I tried to obey. And so, you know, as, 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 gonna get rid of product. You're gonna be user research, it's gonna 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 loud, 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 a proposal, I sent it around to the management team. Turns out, when you actually ask for what you want out loud, you're (laughs) much more likely to get it. Um, 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 stakes seemed really high, right? And this is where kind of that deep imposter syndrome set in. I was like, "Am I even any good at this? Like should I even be in product management? Am, am I ever gonna work in this industry again? Is this gonna be my dark secret that I take to the grave, that Stewart Butterfield fired me three times?" You know? And, and so, you know, that, what, what, I think what, what I couldn't be with in that moment was, was the nos, right? 'Cause 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 asks 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 nos, again 'cause to that emotional regulation standpoint, I just, I couldn't handle the feelings of like, "Ugh," like, "Maybe what I'm doing is not good enough." So instead of pointing the finger at 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 (laughs) to the contrary, by the way, is this like product luminary, visionary, famous person, right? So, you know, clearly not, not based on, on any facts but it was an emotional issue, right? Of like, 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 nos, 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 (laughs) turns out once you hire HR, the firings are final. Um, 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 nos that, 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's gonna 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, honor your desires." But no, like it's real life stuff of like a year of suffering, of 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.

    4. LRLenny Rachitsky54:08

       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.

    5. KBKenneth Berger54:17

       (laughs)

    6. LRLenny Rachitsky54:18

       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 nos, but it was rooted in this confidence that, "You're a founder, you're awesome. They're so lucky to have you. I know what I'm doing. Get out of my way." And then the s- the third phase you also, the issue there was you weren't hearing the nos 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 w- what people are actually saying.

    7. KBKenneth Berger54:46

       Totally. One, and to me the first one is about articulation as well. Because I think that if, if in the beginning it articulated that, "Yeah, I'm confident, but I actually, I wanna do a really good job, right? And I wanna 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. This is an early stage startup, right? Like it, 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 some data to say, "Ooh, yeah, maybe I need to look at this more closely."

    8. LRLenny Rachitsky55:31

       I imagine you've gone through this exercise bef- uh, 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've s- stayed there for many, many years, been head of product at Slack at this point? Just imagining that reality, what would you have done differently and then what would you've imagined have turned out?

    9. KBKenneth Berger55:49

       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? Is of course that's wha- what I would have done. Now, do I know what the outcome would have been? No.

    10. LRLenny Rachitsky56:16

        Mm-hmm.

    11. KBKenneth Berger56:16

        I might have been fired even sooner, right?

    12. LRLenny Rachitsky56:18

        (laughs)

    13. KBKenneth Berger56:18

        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, t- for guarantee of a certain outcome, 'cause no one can promise you that, right? You do it so you can stay in integrity with yourself and not suffer through all this, 'cause at least then 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 go 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'd worked out, but it didn't."

    14. LRLenny Rachitsky57:07

        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 what you could have and to feel integrity with yourself, that you did what you needed to do and you didn't, you're not gonna regret s- something down the road.

    15. KBKenneth Berger57:29

        Indeed.

18. 57:30 – 1:04:58

    Advice on being the first PM at a company or startup

    1. KBKenneth Berger57:31

    2. LRLenny Rachitsky57:31

       I'm gonna 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 little, people asking for advice along these lines. It's classically a very challenging role. Many people don't last. Many people follow your trajectory-

    3. KBKenneth Berger57:48

       Indeed.

    4. LRLenny Rachitsky57:48

       ... where it's like, "Oh shit. What have I done?" Any advice for people that are a first PM at a company or startup, or thinking about that role? How, what can you tell them to help them be successful or at least, uh, at least not, not suffer?

    5. KBKenneth Berger58:05

       To me, it really is about the relationship with the CEO or with the founders, because that's sort of the, the, 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 thing. It's like my, my, my clue to people who report to a founder is to say, "Imagine if you're con- 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 and 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, of like what is the state that the peop- perpen- 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 gonna get anything done. You're not a cons- gonna, you're not gonna succeed in any meaningful way.

    6. LRLenny Rachitsky59:10

       I love that framework of how to think about why a founder is behaving in a certain way.

    7. KBKenneth Berger59:15

       (laughs)

    8. LRLenny Rachitsky59:15

       Just maybe a last following thread there is just what, what should people look for to th- to help them understand if the founder and them are a good fit, if they're gonna have a good time working with that founder? Is there 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 and, and this, and this company as the first PM or not"?

    9. KBKenneth Berger59:34

       I think it's a hard thing to generalize about, but to, to me it really is about understanding expectations, right? of like what do you... You know what I mean? I, I guess this is, you know, uh, predictable coming from 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 and 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, the close... There's no guarantees of course, but it's, it gives you a, a sort of more sure path to having a productive relationship and it's actually something that I, I recommend to a lot of founders for, you know, 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 gonna come in and kinda do my thing the way I've always done it and it's gonna be fine versus coming in and saying, "I actually don't know how I'm gonna 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, what my role and what my place is gonna 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 and what we need? Let's figure it out."

    10. LRLenny Rachitsky1:01:01

        Coming back to our core topic. Is there anything that we didn't cover? Anything that I should've asked you about the skill, the art of asking for what you want? Anything else you wanna leave listeners with?

    11. KBKenneth Berger1:01:12

        I, I do wanna 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, of, 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 gonna be able to do this job without fear hounding me every step of the way?" And I just, and I, 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 wanna come out here and say, there is 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, 'cause 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, um, and it's really meaningful. It matters a lot.

    12. LRLenny Rachitsky1:02:35

        So is the idea there, is the fear there that if they ask for what they want, they'll get what they want, and there's, they let go of kind of this drive to prove themselves and... Is, is that the fear? Like, how is it that they move away from that, uh, need to prove themselves and ???

    13. KBKenneth Berger1:02:51

        Well, I mean, that's, that, that's a longer story.

    14. LRLenny Rachitsky1:02:54

        (laughs)

    15. KBKenneth Berger1:02:54

        I would say, you know, sort of, uh, you know, managing our own fear is a sort of lifelong practice. I'm not gonna claim I'm anywhere near done with it. But, but I guess I'd just say that I think part of, 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? (laughs) 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, that's the short of it.

    16. LRLenny Rachitsky1:03:49

        Amazing. We, uh, it reminds me, we have a cha- I had a chat with Matt Machari and we spent a bunch of time on dealing with fear and overcoming fear, so if folks wanna dig deeper there, they can 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.

    17. KBKenneth Berger1:04:05

        Mm.

    18. LRLenny Rachitsky1:04:06

        (laughs) 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.

    19. KBKenneth Berger1:04:16

        For, for me, I'm, I'm not a big believer in discipline. Um, you know, that I think, you know, some folks come to coaching looking for, you know, sort of a drill sergeant, say, "All right, shout at me and tell me to do better." And I sort of say, "Yeah, uh, no, that's not, that's not how I operate." Because it's not that discipline doesn't work, right? But it's like people pleasing, it's a short term, um, it's a short term coping strategy. Like discipline will get you in the gym for a week, but it's not gonna 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 gonna go anyway." And so, you know, I, I try to be really clear

19. 1:04:58 – 1:05:52

    Contrarian corner: anti-discipline

    1. KBKenneth Berger1:04:58

       with people about that, that I'm not gonna 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, let's look for true long-term sustainable motivation, which means relying on vision, pursuing what you want."

    2. LRLenny Rachitsky1:05:25

       I love that it all ties back to knowing what you want, asking for what you want, and then dealing with the answers that you get.

    3. KBKenneth Berger1:05:30

       I, I am a broken record, admittedly.

    4. LRLenny Rachitsky1:05:32

       (laughs) Amazing. Uh, Kenneth, is there anything else you wanted to share or leave listeners with before we get to our very exciting lightning round?

    5. KBKenneth Berger1:05:40

       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 gonna be writing more about it on LinkedIn.

    6. LRLenny Rachitsky1:05:51

       Okay, amazing. We'll point

20. 1:05:52 – 1:10:16

    Lightning round

    1. LRLenny Rachitsky1:05:52

       people there. With that, we've reached our very exciting lightning round. Are you ready?

    2. KBKenneth Berger1:05:57

       I'm ready. Let's do it.

    3. LRLenny Rachitsky1:05:58

       First question. What are two or three books that you've recommended most to other people?

    4. KBKenneth Berger1:06:03

       Well, I already mentioned Radical Candor. I think that is for sure a modern classic. Um, 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, I love, you know, Kim Scott's writing on that stuff.

    5. LRLenny Rachitsky1:06:25

       We had Kim Scott on the podcast. If folks wanna dig deeper there, we'll link to that episode. I'll let you keep going. Sorry for the interruption.

    6. KBKenneth Berger1:06:31

       Yeah. You have, I mean, you have, I, I mean I, I mentioned before, but I, I actually took, um, uh, 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 me to them.

    7. LRLenny Rachitsky1:06:47

       I'm so happy to hear that. We'll link to that episode as well. Uh, I love that. What a circle, circle of life we've got here. Guests following other guests, taking their courses, joining the podcast. What a happy world.

    8. KBKenneth Berger1:06:58

       Yeah. Indeed.

    9. LRLenny Rachitsky1:07:00

       Uh, okay. Any other books before we move on?

    10. KBKenneth Berger1:07:02

        I, I also love the, uh, 15 Commitments of Conscious Leadership. Um, so I, I, 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, 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 gonna be better if you do them. And so I, 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.

    11. LRLenny Rachitsky1:07:38

        Do you have a favorite recent movie or TV show you've really enjoyed? Hmm.

    12. KBKenneth Berger1:07:42

        I, I'm, I'm a, I'm a recent tennis fanatic, so it was one of the things I picked up during the pandemic, so I really enjoyed Netflix's Breakpoint, 'cause it's a documentary on the best tennis players in the world. And it is just, I, I just find it so, I don't know, I, it's, it's, 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, I'm not gonna be able to do this." Right? Are, are they believing that or are they working through that resistance and saying, "You know, that's just a story out. I actually don't know what's gonna happen, but I'm gonna try to win."

    13. LRLenny Rachitsky1:08:29

        I love that you see coaching opportunities in every- everything, even, even, uh, entertainment.

    14. KBKenneth Berger1:08:34

        I also love, I mean, actually, you know, speaking of, of that, I mean, it's almost too on the nose, but there's this movie Living from a couple of years ago, um, that this British actor who's this sort of, you know, he's, he's, 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, he builds this playground for children and that's actually his, his legacy. Sorry, actually, spoiler alert, whoops ? ? .

    15. LRLenny Rachitsky1:09:10

        (laughs) Uh, you mentioned tennis and you mentioned British people. Uh, I will actually be at Wimbledon this year in London...

    16. KBKenneth Berger1:09:18

        Ooh, nice.

    17. LRLenny Rachitsky1:09:18

        ... with my dad in July and we're gonna host a meetup there while I'm there, just for anyone listening right now, just to give you a heads-up.

    18. KBKenneth Berger1:09:26

        Awesome.

    19. LRLenny Rachitsky1:09:27

        How fun is that gonna be? Okay, next question. Do you have a favorite product you recently discovered that you really love?

    20. KBKenneth Berger1:09:33

        Uh, well, you know, it's, it's funny. I, I used to be a big wine aficionado and I think as, 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, oolong tea. I've got a little cup of Taiwanese Wénshēng Bǎojiǔng 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, I recommend it. Taiwanese mountain teas especially.

Episode duration: 1:13:35