YouSaid · the spoken record

Kenneth Berger

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2024-05-19
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2024-05-19
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  1. 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 it's not worth it. They're going to say no anyway, right? So why even bother? And so, 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 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.

    2024-05-19 · Lenny's Podcast · Why not asking for what you want is holding you back | Kenneth Berger (exec coach, first PM at Slack) · IDENTIFIED FROM THE TRANSCRIPT · source

  2. 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, right? 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.

    2024-05-19 · Lenny's Podcast · Why not asking for what you want is holding you back | Kenneth Berger (exec coach, first PM at Slack) · IDENTIFIED FROM THE TRANSCRIPT · source

  3. That's not fully expressed because it doesn't mean I'm going to get what I want or the people are going to sort of 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 be grateful if we said out loud, I'm bored in this meeting. Let's move things along.

    2024-05-19 · Lenny's Podcast · Why not asking for what you want is holding you back | Kenneth Berger (exec coach, first PM at Slack) · IDENTIFIED FROM THE TRANSCRIPT · source

  4. 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. I'm like, yeah, am I really tuning into how annoyed I am or how frustrated I am or how nervous I am 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? 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, right? 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, what is the part of me?

    2024-05-19 · Lenny's Podcast · Why not asking for what you want is holding you back | Kenneth Berger (exec coach, first PM at Slack) · IDENTIFIED FROM THE TRANSCRIPT · source

  5. So, I think sometimes it is about alignment, right? The disagree and commit. So I see that a lot, right? Of like, you know, a founder saying, hey, I'm super respectful 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 actually follow through with that, right? And I understand that might be disappointing or frustrating or what have you, but part of the expectation with this role is that you can roll with disagree and commit sometimes when that's necessary.

    2024-05-19 · Lenny's Podcast · Why not asking for what you want is holding you back | Kenneth Berger (exec coach, first PM at Slack) · IDENTIFIED FROM THE TRANSCRIPT · source

  6. Like, well, that doesn't mean that there aren't consequences for their actions, right? Part of really respecting them is respecting that they

    2024-05-19 · Lenny's Podcast · Why not asking for what you want is holding you back | Kenneth Berger (exec coach, first PM at Slack) · IDENTIFIED FROM THE TRANSCRIPT · source

  7. To me, a lot of the classic examples are around feedback, right? Because I work with a lot of founders who 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 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 the CEO wants them to be delivering. Because it doesn't seem that nice. Like, oh, I think of myself as nice and of being so kind and of people loving me.

    2024-05-19 · Lenny's Podcast · Why not asking for what you want is holding you back | Kenneth Berger (exec coach, first PM at Slack) · IDENTIFIED FROM THE TRANSCRIPT · source

  8. Immediately, right? And so for this, 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 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 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 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% 100% aligned and 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 going to get what we want or that everyone's going to agree.

    2024-05-19 · Lenny's Podcast · Why not asking for what you want is holding you back | Kenneth Berger (exec coach, first PM at Slack) · IDENTIFIED FROM THE TRANSCRIPT · source

  9. 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, 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 to do is to really tune into the parts of them that maybe aren't so fine. Like, gosh, 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 kind of, 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 articulate these sort of, you know, wildly unrealistical. So this is the founder that just wants everyone to agree with him all the time and to obey him.

    2024-05-19 · Lenny's Podcast · Why not asking for what you want is holding you back | Kenneth Berger (exec coach, first PM at Slack) · IDENTIFIED FROM THE TRANSCRIPT · source

  10. 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 key places that people tend to sort of have missteps here are one in this phrase, it's fine. I think of the It's Fine cartoon with the flames, you know, and the dog, I think it is. But I think a lot of us fall into that trap of saying, you know what? I'm fine. Actually, I don't need anything. I'm good.

    2024-05-19 · Lenny's Podcast · Why not asking for what you want is holding you back | Kenneth Berger (exec coach, first PM at Slack) · IDENTIFIED FROM THE TRANSCRIPT · source

  11. It does. And 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 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 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 going to be. But if you're a startup founder, you 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.

    2024-05-19 · Lenny's Podcast · Why not asking for what you want is holding you back | Kenneth Berger (exec coach, first PM at Slack) · IDENTIFIED FROM THE TRANSCRIPT · source

  12. Some people call this a whole body, yes, because sometimes 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.

    2024-05-19 · Lenny's Podcast · Why not asking for what you want is holding you back | Kenneth Berger (exec coach, first PM at Slack) · IDENTIFIED FROM THE TRANSCRIPT · source

  13. 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 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 is a day. 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. So, but let's get to a hell yes. What would it take for us to get there?

    2024-05-19 · Lenny's Podcast · Why not asking for what you want is holding you back | Kenneth Berger (exec coach, first PM at Slack) · IDENTIFIED FROM THE TRANSCRIPT · source

  14. So I have a more expansive definition of no than most people, I think. Because for me, it's not a yes unless it's a hell yes, right? Because you really want enthusiastic consent, right? Not just maybe kind of. I'll try. 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 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 May 1st. And then May 1st comes and surprise, surprise, you know, your milestone is not done, right? Because you didn't sort of go for that hell yes.

    2024-05-19 · Lenny's Podcast · Why not asking for what you want is holding you back | Kenneth Berger (exec coach, first PM at Slack) · IDENTIFIED FROM THE TRANSCRIPT · source

  15. Is really scary because, God, what if I don't get it? What does that mean about me? Am I a failure? Or 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 what you want. Because otherwise it's articulate, ask, accept.

    2024-05-19 · Lenny's Podcast · Why not asking for what you want is holding you back | Kenneth Berger (exec coach, first PM at Slack) · IDENTIFIED FROM THE TRANSCRIPT · source

  16. For specifically for articulating what you want, because that's kind of the first step of the asking for what you want process. It really is as simple as that, right? Of let's start with what you have consciously in terms of what you want. And 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 learning 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 that thinks asking for what we want is scary and articulating a big dream that we might not get

    2024-05-19 · Lenny's Podcast · Why not asking for what you want is holding you back | Kenneth Berger (exec coach, first PM at Slack) · IDENTIFIED FROM THE TRANSCRIPT · source

  17. 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, ah, 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 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 hard. I don't know that I'm going to get it. But damn, it's worth trying, right? Like I want to go for it.

    2024-05-19 · Lenny's Podcast · Why not asking for what you want is holding you back | Kenneth Berger (exec coach, first PM at Slack) · IDENTIFIED FROM THE TRANSCRIPT · source

  18. It implies a better world where that complaint is resolved. And so often that's the tool that I'll take people to first, to say, all right, great. 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 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. What's really behind that? And so I think 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.

    2024-05-19 · Lenny's Podcast · Why not asking for what you want is holding you back | Kenneth Berger (exec coach, first PM at Slack) · IDENTIFIED FROM THE TRANSCRIPT · source

  19. 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 to me? So, you know, one of my favorite techniques here is this concept they call the dream behind the complaint. Because 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?

    2024-05-19 · Lenny's Podcast · Why not asking for what you want is holding you back | Kenneth Berger (exec coach, first PM at Slack) · IDENTIFIED FROM THE TRANSCRIPT · source

  20. 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 for what we want, that can get us really focused on the fears rather than focused on the goals.

    2024-05-19 · Lenny's Podcast · Why not asking for what you want is holding you back | Kenneth Berger (exec coach, first PM at Slack) · IDENTIFIED FROM THE TRANSCRIPT · source

  21. 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? Of okay, normally, you know, when I was at Adobe, it's a big company, you know, they're going to 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 stake 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 than on actually achieving what we do want, right? And that's a really critical distinction, right? Because, you know, if we're running away from our fears.

    2024-05-19 · Lenny's Podcast · Why not asking for what you want is holding you back | Kenneth Berger (exec coach, first PM at Slack) · IDENTIFIED FROM THE TRANSCRIPT · source

  22. There's so many examples. I think we'll eventually get into the story of how he was fired from Slack. But I think for me, 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've 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.

    2024-05-19 · Lenny's Podcast · Why not asking for what you want is holding you back | Kenneth Berger (exec coach, first PM at Slack) · IDENTIFIED FROM THE TRANSCRIPT · source