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

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

Kenneth Berger
You're hired. How do you know that this is something you need to be working on? If you're more in the people pleasing camp, maybe you're used to not asking at all. You're hoping that people are reading your mind. And if you're sort of more in the control freak camp, maybe you're used to ordering people around and saying, go do this now.

Lenny Rachitsky
How do you know what you want? Complaints are great inspiration. Every complaint implies a dream. Let me envision a better future. Let me think about what's an effective way to actually move towards that.

Kenneth Berger
See what it's like to not be sort of living in fear all the time.

Lenny Rachitsky
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 ten 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, dont forget to subscribe and follow it on your favorite podcasting app or YouTube.

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Kenneth, thank you so much for being here. Welcome to the podcast. Yay. Thanks for having me. I love that.

Kenneth Berger
Yay. We should, that should be a tradition that everyone goes with. I love that. So we originally met when I was doing a post on being a first product manager at a company. You were famously the first PM at Slack, and then you ended up transitioning into executive coaching, which is what you do now.

Lenny Rachitsky
What we're going to be talking about today is something that you described to me as your personal magnum opus. The output of ten 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?

Kenneth Berger
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, when it comes to are we really pursuing the things that we want in life?

Right? And I think to me the flip side of that is sort of the reason that the stakes around asking for what you want are so high. Because, yeah, we can't guarantee we're going to get what we want, but if we're asking for it regularly, if we're listening to the response, we're respecting the no's we get from the world, then we can 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 what's important in sort of achieving our purpose. 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. For me with clients, I think what I'm often looking for is the sense of being stuck because everybody's got frustrations, everybody gets nervous at work sometimes, but if we're in the same stuck place week after week after week in our coaching sessions, probably you're trying the same thing and not getting any different results.

It's that definition of insanity thing, really. I look at that and say, okay, maybe you're asking for what you want, maybe. Although often people aren't. But even if you are, you're probably not achieving it. You're not getting the results that you want.

So why are we not learning from that? Why are we not moving forward, getting new data, trying something new, actually treating it as a iterative development discovery process. So I think that stuckness is one thing, and I think the other thing I look for is interpersonal conflict, because I think that 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 of like, you know what? You better do what I say.

I'm your boss, you're my report. You better obey or agree or whatever it is. And of course, the danger of that is interpersonal conflict, even if you are their boss. Right. That's a really disrespectful way to come into the conversation.

And yeah, it's an obvious source for a lot of issues. Before we get into how to learn to do this better and more of why this is so important, is there an example from your career where you did this really badly or you didn't ask what you want? There's so many examples. I think we'll eventually get into the story of how it 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 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.

There's no way to have that conversation. Respectfully, 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 candidates about to tell me. You said one is you feel you're stuck in your career, something, you're just not making progress.

Lenny Rachitsky
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? There are more. I think those are great things to look for. I think it's also good to look for kind of a sense of things being high stakes, right.

Kenneth Berger
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 when I was at Adobe, it's a big company. They're going to be fine either way, no matter what I do, right. I can be easygoing, let someone else have their way in the meeting.

But when it was my company, when it was my vision on the line, I didn't feel especially flexible. The stakes seemed really, really high. 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.

That's a really critical distinction, because if we're running away from our fears, it doesn't necessarily mean we're getting anywhere meaningful for what our desires are. And so that sense of high stakes that often we can get, whether it's in interpersonal conflict or being afraid of asking for what we want want, that can get us really focused on the fears rather than focused on the goals. There's a question I was going to say for later, but it's something that's very top of mind for me, is knowing what you want. Like, how do you know what you want? There's basically knowing what you want and then asking for what you want.

Lenny Rachitsky
And I often, I'm like, I try to. I'm like, I like equanimity in my life. And so I often don't ask for what I want or kind of push down maybe what I want or I don't think about what I want. I just want other people to be happy. And I'm curious what people can do and what I can do to get better at knowing, here's what I actually want.

Here's what would make me happy and fulfilled. What are some skills there I could work on? And other people can work on. Well, first of all, I'd say you're very far from alone there, right? I mean, I think the people pleaser coping strategy is one of the sort of most classic, and it is effective.

Kenneth Berger
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 in terms of, am I really pursuing the things that are important to me?

So one of my favorite techniques here is this concept they call the dream behind the complaint, because you're right that 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. That can sound really scary for people, but we're very good at complaining. 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 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 often that's the tool that I'll take people to first to say, all right, great, let's complain, right? Feels so fun and good and releasing to complaints.

And let's look at what that sort of implied world is behind that complaint. What is this vision? And then to really check, 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 we like, oh, my dream is that 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 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. And they sort of say, I don't know if that's quite my dream. Right? And so if your dream is so embarrassing to say out loud, you can't even really own it, maybe that's not the right dream.

And so that checking whether it actually feels 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. 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?

Lenny Rachitsky
Is it you dream about what would make you happiest? Is it like, complain and see what's at the root of it? Is it just imagine a world where you're really happy and see what emerges. Specifically for articulating what you want, because that's kind of the first step of the asking for what you want process. It really is as simple as that.

Kenneth Berger
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 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. The steps I outline are articulate what you want, ask for what you want intentionally, and accept the response and then try again. Because it's an iterative process, 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 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, yeah, articulate, ask, accept. Okay, you're getting into where we're going to go before we get there. Final question.

Lenny Rachitsky
This idea of dealing with no, I think this is the other big blocker for people is like, it's so scary to ask for, like, something I really want or ask for something bigger that is really important to you. What is it that you advise there of just kind of getting over that sphere of just like, asking for what you want. 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.

Kenneth Berger
Because you really want enthusiastic consent, right? Not just maybe, kinda. 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, I think maybe we can deliver by May 1. And then May 1 comes, and surprise, surprise, your milestone is not done because you didn't go for that hell yes.

I think part of what I encourage people to do is one to really hear anything short of a hell yes as a no. It's not a bad thing. 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, I'm hearing maybe your lukewarm on May 1 is a date.

What would be a hell yes day for you, where you could say, absolutely, we can deliver on that. 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. But let's get to a hell yes.

What would it take for us to get there? That's a really helpful framework and phrase to use, is just what would it take to get to hell yes. Not just what would it take to get to you feeling comfortable with this? Or what would it take for you to just agree to this? It's more a hell yes.

Lenny Rachitsky
And your point there is hell yes is when they actually fully agree. Yeah. Oftentimes people kind of like, yeah, yeah, yeah. And then they don't actually follow through. Some people call this a whole body yes.

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

Lenny Rachitsky
And this applies to, you're giving examples here of just like getting like aligning a deadline. I imagine the same skill applies to everything you in life, like relationship questions and friends and family and work. It does, you know, it is something universal. But I do think of it as being particularly relevant to my work with startups because I work primarily with startup founders because with startups you know that mostly they fail. Right?

Kenneth Berger
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 right. A lot of people, we operate in a safer world where we're more clear exactly what the outcomes are going to be. But if you're a startup founder, you've got to be okay with I'm just going to go for this and I know I probably won't get it, but it's so meaningful to me, I'm going to go for it anyway. And so to me that's not just about the big picture of running a startup, it's about really anything you might want in life because that's such a useful perspective to say, I know I'm not going to get it, I know I'm not guaranteed to get it, I'm not going to be attached to that.

I know people aren't obligated to tell me yes, but im going to go for it anyway because I want it and thats enough. So lets 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 lets just walk through them. So the first step is articulating what you want and weve sort of gone into this a little bit. But to me I think that the key places that people tend to sort of have missteps here or one in this phrase, it's fine.

I think of the it's fine cartoon with the flames, you know, the dog. I think it is, but I think a lot of us fall into that trap saying, you know what, I'm fine, actually, I don't need, I don't need anything, I'm good. And again, this is tempting, right? Because it's so nice to have this idea that I'm fine, I don't need anything. And in a certain way thats a nice attitude because were not guaranteed anything.

So its nice to be okay with the status quo, but for those folks often what Im encouraging to do is to really tune into the parts of them that maybe arent so fine. Like gosh, id really, id prefer it a little bit if things were this way or yeah, im a little bit bothered by this or im a little bit nervous about this. And so kind of tuning more into those subtle emotions that are pointing them towards. Sure, im okay with the status quo, but I want something more. And so helping them articulate that in a clearer way where they can want something without being attached to having to get it.

The other extreme of this is people who articulate these sort of wildly unrealistic goals. So this is the founder that just wants everyone to agree with him all the time and to obey him immediately. And so for those folks, it really tends to be more about saying it out loud because once you say it out loud it is clearer. Yeah, that's not like, I'm not, that's not really what it's about. And so for those folks, I tend to ask them to go deeper, to say, yeah, I know you're not a control freak, right?

You don't want 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% aligned in everything. But it doesn't mean there's a certain feeling that I have when I go into work, even though I don't know that we're going to get what we want or that everyone's going to agree. Do you have any examples from your time you could share? If someone articulating what they want and figuring out how they articulate how to articulate what they want, just to make it even more real to me, a. Lot of the classic examples are around feedback because I work with a lot of founders who are not the classic control freaks.

They're super nice and their teams love them and they love their teams. For them, it can be really hard to deliver hard feedback, to 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. 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, when they're not aligned with the culture, or they're not delivering in the way that 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 being so kind and people loving me and it's like, well, that doesn't mean that there aren't consequences for their actions.

Right. Part of really respecting them is respecting that they can make the choices they want and they're grown ups enough that they can deal with the consequences of those choices. Can you even get more concrete there? Is it like we need to hit this date or there's going to be big problems, or is it like, I need you to hire this large of a team? I don't know.

Lenny Rachitsky
Like what, what is it that they, they're not articulating that they later realize, oh, here's what I need to articulate. So I think sometimes it is about alignment the disagree and commit. So I see that a lot of founders 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 actually follow through with that. And I understand that might be disappointing or frustrating or what have you.

Kenneth Berger
Part of the expectation with this role is that you can roll with, disagree and commit sometimes when that's necessary. That's an awesome example. I fully get that and I could see how many people are not how scary that is to a lot of people. One is just like coming to terms with, this is what I actually want to be doing, but I just don't feel like I can because it's going to, I think, upset people. Yeah.

Lenny Rachitsky
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 happy, be happier, or things would probably run better. That's a really, that's a really cool example of how to do that because that's easy. Just like, oh, yeah, if we like, actually can make a decision in this meeting, that'd be really cool.

Maybe we should try to do that and ask for that. Is there any other tips and approaches to helping you figure out what you want? It always comes back to integrity. And a great way to do an integrity check is to just look for have I fully expressed myself? And so I think we've talked a little bit about sort of charting your feelings as a piece of that.

Kenneth Berger
Of 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 express those in whatever way is appropriate, then probably I'm not fully in integrity. And I think saying what you have to say is a piece of that too, right? 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 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 that's not fully expressed? Because it doesn't mean I'm going to get what I want or the people are going to give me all my dreams immediately. But it feels so much better to have it out.

That sort of suffering, 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 versus saying, probably a lot of people would be grateful if we said out loud, I'm bored in this meeting. Let's move things along. 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 compliance for SoC two, ISO 27,001, HIPAA, and more.

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That's v dash tv slash Lenny. Okay, this is a great segue to 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?

Kenneth Berger
So for asking what you want, I think the really important tweak here is asking intentionally. Right. Because I think a lot of us are kind of stuck on a certain track that's comfortable for us when we ask. And so if you're more in the people pleasing camp, maybe you're used to not asking at all. You're hoping that people are reading your mind and just magically knowing what you want.

And if you're sort of more in the control freak camp, maybe you're used to ordering people around and saying, go do this now. And so for both of those folks, it's not about, I think if you ask any of them, is this working for you? They'd say no. Right. Of course, it's obvious from an effectiveness standpoint, it's not working well, but they more just haven't embraced that.

Yeah, you can do it a different way. Right. That they only really see one way of doing it. And so part of asking for what you want effectively is really just recognizing the rut that you get stuck in and sort of working through all those narratives that make us resist asking in a different way. Right.

Because often the people who don't want to ask have a story that says, this is too risky or it's not worth it. They're going to say no anyway, so why even bother? And so these are all sort of very common things that people go through, but then they end up not actually asking for what they want and actually expressing who they are and what they stand for in the world. And that has a really serious cost. I think, that we tend to tell ourselves the story, oh, this is fine, I'll be fine, versus owning, I'm going to be living my life not asking for what I want.

Do I really want to be at my funeral and have people say, oh, Kenneth played it safe. He didn't really go for his dreams, but he was nice. No one was ever mad at him. That's not what we want people to say is our eulogies. No, that's good motivation.

Lenny Rachitsky
Say, in this example you gave of, I need us to make a decision. I know I'm trying to keep everyone happy, but we need to make a decision. Do you have advice for maybe phrases of how to approach? You talked about making intentional. How do you actually go about doing that?

Is it like the way you communicate it? Is it something else? How do you actually do this without pissing people off and also just, like, risking too much? Well, and so, but even implicit in that question, right? Like there's to me that question of, oh, how do I do it without there being any risk of ever pissing anyone off.

Kenneth Berger
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 in theory asking is easy. Oh, you just try some way and maybe people are pissed off and maybe they're not, but probably it's going to be fine and you'll have the chance to try again and iterate and learn from it.

But often we get stuck. So we don't get to go through those levels of iteration because we want to make sure we're going to get the outcome we want. We say, oh, well, I'm not willing to ever piss anyone off ever. And so I'm just going to be stuck at this step because like, I haven't figured out what's going to guarantee me. And of course there's no guarantee.

We can never guarantee that people are going to feel a particular way. And so part of asking for what you want effectively is actually bringing some compassion for yourself. God, of course we all want to be sure that the way we ask is going to be effective and no one's going to be mad at us and we're going to get all of our dreams come true. But yeah, 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? Such a good point about what you identified and the way I think about it and the way I think a lot of people I think about is just like how I do this without causing anyone any pain or risking anything going wrong. To your point, part of it. So you talk a lot about founders.

Lenny Rachitsky
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 power, quote unquote. Is there anything that you suggest these folks do differently or think about this differently, or is it kind of the same thing in the end, everyone has power in some way? How would you think about this if you're just like, say, a product manager, individual contributor?

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

Like, are you willing to reconsider this? That's such a great approach. It's like, very not scary to say that. It also, I think highlights something I wanted to touch on is I think people have a lot more influence and power than they think they do. Say a PM on a team disagrees with a plan for a product, like, people actually care about your opinion and you could actually change things by just telling them, I don't think.

Lenny Rachitsky
I think this is a bad idea and you often don't. Is that what you find, that people have a lot more influence than they think they do? Anything along those lines that comes up, you're actually. You're giving me deep goosebumps because this is. I think this is a really underappreciated thing in terms of asking for what we want.

Kenneth Berger
Because especially in the PM world, we're trained to look for data. We're not just going to state an opinion. We're going to say, oh, the A B test said this, or 30% of our users do this, or the ROI on this is X and data is great. We love data for a reason, of course. And I think people forget about exactly what you're highlighting, that your relationships matter and that just your opinion because you believe something or because you want something, often that's enough.

Because guess what? You're in a relationship with these people you work with, they care about, you, have some leverage with them. And I think that often people go the other way and say, oh, I've got power, I'm going to try and leverage it. But actually, if you go the other direction and you're humble and you say, I know I can't make you do anything, it's not my call to make, but, man, this is really what I want. I'm just going to put it out there and ask that.

I think it feels really vulnerable and uncomfortable to not lean on data as a sort of way of saying, no, no, I'm right. So you should believe what I believe, but just say, actually, I don't know that I'm right. This is just what I think and I hope that's enough on its own. Do you find that that's actually a crutch? A lot of times to people not saying anything is they don't have that data, they don't have evidence.

Lenny Rachitsky
And they just, like, I shouldn't say anything because I don't. Someone asks for why I don't have a great answer. I just, I just think this is what it should be. Totally. Well, and, you know, I think there's a balance there as with anything like is ignoring data and going in gut all the time great?

Kenneth Berger
Probably not, right? We use data for a reason, but I think there are all these sort of, all these moments when we are making a gut decision and having all the data there means having the opinion set out loud. And I think often the danger is of people saying, oh, I don't have data. To back this up is just what I think. And I'm not sure people are going to agree with me, so I'm just not going to say it.

We don't have the data of all those gut opinions of these subject matter experts in the room, even though that gut information to me is just as important as anything we could get from the SQL database or whatever. Before we move on to step three, you talked about the opposite of asking for what you want. This was just, step two is just complaining and being angry later. I knew this project was going to fail. I knew this was a terrible deadline.

Lenny Rachitsky
I knew this design was not great. Anything more you want to say along those lines of just like, if you're not asking for what you want, complaining is often a sign that you should be doing that more. To me, complaints are great inspiration. And so I think the, you know, to me, you know, like, I love radical candor, for example, right? You know, where 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.

Kenneth Berger
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 going to be an effective way to do it, but it can be great inspiration to say, gosh, that complaining means I'm frustrated. What am I frustrated about?

Let me envision that better future. Let me think about what's an effective way to actually move towards that? What's an effective way to communicate that desire? That's actually likely to get me towards a yes. And so when we actually embrace that sort of frustration, annoying, complaining, thing and follow that thread down and think about how to be effective.

That way we can actually get something really compelling and useful, but it requires actually embracing that part of ourselves that sometimes we're a little bit ashamed of. Like, oh, I kind of like that whiny part of myself. Like, I'm just going to push that one down versus actually taking what it has to say as important data. That's a really good point. I think that's actually another blocker for a lot of people, is just, I don't want to be a complaining person.

Lenny Rachitsky
I just want to be like, let's do this. I'm in. Let's go. Let's. I don't want to be seen as a squeaky wheel.

Is there anything you say there about as a resistance point for people? Well, I'm a big fan of internal family systems, which is this sort of psychotherapy technique that really talks about parts and the sort of parts of ourselves and the ways in which they don't always agree with each other. And part of why I love this approach is a, because we already use this language. 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.

Kenneth Berger
And I don't respect that part of me as much. And so really, to sort of ask effectively, we generally need to embrace all these parts and really bring in all the information they're bringing in. Because if we ignore the part that's really scared to ask, well, yeah, then we're going to stay stuck versus if we come in and say, hey, buddy, why are you scared? Like, you seem terrified. What's going on?

Oh, well, man, you think your whole professional reputation is staked on this and you're an imposter and they're going to find out and then you'll never work again. Well, of course you'd be scared. That makes a ton of sense. And by embracing that instead of ignoring that and being ashamed of that, that is often how we soften those fears and say, yeah, I know that's scary, but we also know that's not really true. Right?

Like, you're not an imposter, right? You're an experienced professional man, there's so. Many threads we can't fully hear. This whole line of internal family systems. Right.

Lenny Rachitsky
That's a. That's its own podcast episode, potentially, and then imposter syndrome. We've touched a bunch on different podcast episodes, but I'll avoid going in that direction. Something you reminded me of is, uh, we just had Carol Robin on the podcast who taught this class, touchy feely, at Stanford, for a long time, which is all about helping people learn how to deal with other people, which we never learned in life. It's like a class, how to learn to work with other people.

Kenneth Berger
I took one of Stanford's tea group weekends, summer of 2020, I think, a month after George Floyd was murdered and was facilitated by a black woman. And it was one of the most profound, transformative weekends of my life. I mean, because tea groups already, people rave about them, but having it at that point in history, with those people in the room, a lot of tears. I imagine it was crazy. I mean, it was really wild.

Lenny Rachitsky
I feel like every single person that has gone through, I think it's called leaders in tech because of the broader umbrella term. And Carol talked about it. Everyone that has gone through it 100% has told me that it's a transformative life experience for them. And so. And you had a.

You had a bonus transformational piece. So, anyway, if people want to check out that episode, I will link to it in the show notes. But the reason I brought it up is Carol shared this framework for how to actually give feedback in a way where people can receive it that I'll just highlight here. I have it here. And it's somewhat related to nonviolent communication, which is what you touched on.

And she told me, actually, she taught this way before nonviolent communication came out with their whole philosophy. And it's basically when you want to give someone feedback, the template is when you do a behavior, I feel a feeling, and she's big on, say, actual feeling word, not like I feel like, or I feel that blah, blah, blah. And step three is, I'm telling you this because. And then what, you want them to change. Do you find that sort of approach helpful?

Kenneth Berger
I do. I teach the same thing. And, yeah, I think, you know, sort of Carol's approach and nonviolent communication. DBT teaches a similar approach they call dear man to me. What's DBT?

It's a dialectical behavioral therapy. It's related to CBT. Um, so there's. There's kind of rough consensus, you know, 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 think that, you know, what can we know factually? Well, we can know our thoughts. We can know our feelings, because no one else can know that better than us. And maybe we can trust our eyes. Right?

Like, you know, what would a video camera have recorded? Right? And that's about it. And so I think often we get really distracted by all these stories we have about the data. But when we bring it back to that fundamental core of, this is what I think, this is what I feel.

This is what I've observed in the world. It tends to make the ask a lot clearer versus these stories, like you mentioned, of. I feel like you're an asshole. It's like, well, that's a story. That's not a fact.

Lenny Rachitsky
Yeah, I feel that is not the right way to say I feel. What do you actually feel? Yeah. Okay, so let's move to step three. We've been going on this whole tangent of therapy and stuff, which is amazing, but let's make sure we cover all three steps.

So step one, again, was articulate what you want. Step two is ask for what you want. What's step three? So, to me, step three is actually the trickiest for most people so far. They're all tricky to me.

Kenneth Berger
Oh, yeah. They're all. They're all tricky. For sure. The most tricky.

Lenny Rachitsky
Okay. But step three is accept the response. And it might seem so simple, right? But it actually is kind of subtle. And so one reason is that idea of sort of the whole body yes or the hell yes.

Kenneth Berger
Right? Because I think often we really want a yes. And so we're very, very biased to look for a yes versus accepting no. That was a no. Right.

If someone kind of made this face, like that's a no, it doesn't matter what comes out of their mouth, right. And so the challenge of accepting the response is often that of, you know, of hearing the no, but not over accepting or under accepting 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 going to happen for me again. Right.

And that's because they get so scared. Right. But actually, no. Like, that's over accepted. 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 in a different time. And on the flip side, right. In that sort of more control freak mode.

I think for them, they'll, they'll often sort of kind of skip over the response, say, well, you know, they said no, but they don't know what they're talking about, or they're my direct report, so they have to do what I say. And so these are all kind of, you know, these are all kind of fundamentally disrespectful ways to operate in this relationship. And when we're talking about asking for what we want, we're talking about influence. So you need to have good relationships. You can't be influential with bad relationship.

And so really accepting the response is about, yes, I'm going to be genuine about what I want, but I'm also going to genuinely care about you and have deep respect for your sort of ability to consent or not consent to whatever the ask is. Because I think the counterintuitive thing is that often when we really respect people's nose, it can actually be more influential, more motivating. If someone says, okay, no, I'm not ready to deliver this on time, be like, okay, well, I'm going to give the project to another person. I'm taking your know, 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, you're not coercing them. Right.

You're just saying no. You said no so that your no is no. And I accept that. So 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.

Lenny Rachitsky
Part of it is there's this, like, not yet component. We had Mehika Kapoor on the podcast. She was a PM at Figma, and she had this really great approach to being, to building new things within companies. Is just like, everything to her is not yet a no, is it? Not yet.

And the way you phrased it is it could just be the way you asked. It could be like, maybe they'll agree if you can figure out a better way to pitch the thing. Is there anything more you can add there about just this idea of it's not no forever? Acceptance of the response is primarily an emotional regulation issue, right. Because once we get our emotions intact, it's just, is it yes or is it no?

Kenneth Berger
Right. And if it's no, which it probably is, because most of the time the world tells us no, then the question is all right, what can I learn from this? What am I going to try next? And so when we're able to emotionally regulate, it's all very cut and dry, right? It's like, okay, here's data to tell me what to try next.

And so, really, 99% of the challenge tends to be all the feelings that come up for us when we hear no. Right? Because we hate hearing no. It's so uncomfortable. And so part of the practice of getting good at asking for what we want is recognizing you're going to hear no all the time.

And that's completely normal and fine. It doesn't need to be something so scary or awful. Easier said than done in real life. Is there an example of either a client of 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 your own career.

I gave a talk about this sort of right after it happened, but I was fired from Slack three different times, which I feel like has to be some kind of startup record. I don't know know who would be the record keeping body for this. But now, ten years on, I have different perspective, of course. And so this was almost exactly ten years ago, spring of 2014, and I just got in the job as the first pm at Slack, and it was already the hottest thing out there. It was only a couple dozen employees, and I came in excited, but also a little insecure because I just come off kind of my breakup with my co founder.

I just wanted to kind of put my heads down. Put my head down and do a good job. I was engaged at the time, so Slack already knew I was going to be going away on a bachelor backpacking trip, wedding and honeymoon in the fall. And so I kind of came in kind of naive and overconfident of, like, I've been a founder, I've worked on iconic products. I know how to do this.

I'm a pro. I'm just going to go in and do the work. And so instead of getting really clear on what does success look like here, or what's your culture, or, like, what are your expectations of me, I just went in and made my best guess and went for it. And lo and behold, turns out what I came in with, that supreme overconfidence, was not what they wanted at all. They had kind of been in the trenches, reinventing from the game to slack.

They've been through layoffs, really hard times together. They wanted someone to come in humble and to earn their trust of this core team that had been together for years. And so I just didn't get any of that. I wasn't 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 because I was working for him and you need to have a good relationship with your boss. But the problem was in the first firing anyway, was I had not articulated those goals. And so I shouldn't have been surprised when six weeks into 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, it seems like it's not working out. Let me know how you want to wrap it up. So as you can imagine, I freaked out, right? I loved this job. I love this company.

So I profusely apologized. I said, I'll do whatever it takes. I'm so sorry. Know I'm going to be committed to turn this around. And so, early stage startup, turns out firing doesn't always stick.

Monday morning, I had my job back, but obviously things were not the same as they'd been before. Because in the second era that what I wanted was sort of better 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, was I going to get fired? Was I going to not make the most of this opportunity? And so I went fully into people pleaser mode.

And so that meant that even though what I desperately wanted was to have this good relationship was to sort of be successful, build a great product, I had a year of one on ones for the CEO. I never, never ever asked for what I wanted. I never said it out loud, right? Because I was scared. I was scared of what the consequences were.

I knew there were 100 pm's standing behind me ready to take my job if the CEO is ever a moment unhappy with me. I said, no, I'm not going to take the risk. I'm too scared of what the consequences might be. I held all that fear and all those desires. I just want to do a great job.

I want us to be awesome partners and build this amazing industry changing product. I never said any of that stuff out loud. I just put my head down and I tried to obey. And so as you can imagine, this didnt work very well. I was feeling horrible day to day.

I was terrified of this guy I was working for. Again, I shouldnt have been surprised, but I was. When I got fired for the second time, it wasnt quite firing, but this time id come back from my honeymoon and I had a phone call on Monday that said, seems like product management is not working out for Slack. Were actually just going to get rid of production. You're going to be user research.

It's going to be fine for me. I love user research. But that was the beginning of my career. I was not interested in going back to that. 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, let's keep me in product.

I've got an idea for how we can run it. 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 much more likely to get it. And so within a week, this new plan had traction with the management team and I had my old job back again.

Everything was fine. Except of course it wasn't fine because now I was scared. But the stakes seemed really high. And this is where that deep imposter syndrome set in. I was like, am I even any good at this?

Should I even be in product management? And am I ever going to work in this industry again? Is this going to be my dark secret that I take to the grave that Stuart Butterfield fired me three times?

And so I think what I couldn't be with in that moment was the nos because I was getting no after, no after, no after, no from Stuart and the rest of the management team saying, yeah, what you're doing is not working for us. Your ass are not landing. You're not being effective in the way that you want to be effective because I wasn't able to hear those no's again 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 to the contrary.

By the way, is this like product luminary, visionary, famous person, right? So clearly not based 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 I was not articulating what I wanted, I was not asking for it. And I certainly was not listening to the noS.

I shouldn't have been surprised when finally, the third time it came down and this time it was serious because we had HR. So it turns out once you hire HR, the firings are final. And so I only made it to a year at slack. And it was a year of just utter torture because I spent that year being fully out of integrity with myself, right? Never saying what I really wanted, how I really felt, because it didnt 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 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 no's 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. Stuart 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, even when we don't know exactly what the outcome is going to be. And so that's really the story of how I became a coach, 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 can sound so fluffy to say, oh, focus on integrity, 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. Wow, what a story, and I love that. It's kind of a microcosm of everything we've talked about.

Lenny Rachitsky
You've kind of did all the things that you teach people to avoid. Exactly. And I think what's interesting is you kind of went through these three phases. Interestingly, at the beginning, your first phase was you were not hearing the nose, but it was rooted in this confidence that your founder, you're awesome. They're so lucky to have you.

I know what I'm doing. Get out of my way. And then the third phase, also, the issue there was you weren't hearing the nose, but it was more from fear of being fired again. And so it's interesting that there's these different reasons. You're not hearing what people are actually saying totally.

Kenneth Berger
Well. And to me, the first one is about articulation as well, because I think that if in the beginning it articulated that, yeah, I'm confident, but actually I want to do a really good job and I want to have good relationships. So let me think about intentionally, how do I create those outcomes? But because I hadn't articulated that's what I wanted, it didn't even occur to me, like, oh, yeah, I need to do some intentional relationship building, figure out some metrics for success. Because it was an early stage startup, 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, oh, yeah, maybe I need to look at this more closely. I imagine you've gone through this exercise many times, but say you were to do it again, what would you do differently, and what do you think would have happened? Do you think you would have stayed there for many, many years, been had a product that's slack at this point, just imagining that reality, what would you have done differently? And then what would you have imagined have turned out?

Well, I mean, obviously, broadly, I would have asked for what I wanted, right. And what I wanted was I wanted to do the best work of our life. Right. I wanted to have a deep professional partner and the CEO and the rest of the product and management team. And yeah, I wanted to produce great work that people loved.

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 what I would have done. Now do I know what the outcome would have been?

No, I might have been fired even sooner, right? Like they might have said no, like, this is not working out. Like, let's just be done here. And so that's what's tricky about this is it really isn't about the outcome, right? Of course asking for what you want makes you more likely to get the outcome you want, but you don't do it, you know, for guarantee of a certain outcome because no one can promise you that, right?

You do it so you can stay in integrity with yourself and not suffer through all this. Because at least 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 get another job at another startup, right?

It's not the end of the world. And I think that the mistake we make is pretending that it is, right, of saying, you know, going into fight or flight and saying this is like a severe existential threat to who I am and sort of my safety in the world versus being like, yeah, I'm disappointed. I wish it had worked out, but it didn't. 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.

Lenny Rachitsky
It's to feel like you did, which you could have, and to feel integrity with yourself that you did what you needed to do and you didn't. You're not going to regret something down the road. Indeed. I want to take a quick tangent down the being the first PM route real quick. There's a lot of people that think about being the first PM at a startup join as the first PM.

I imagine you work with people asking for advice along these lines. It's classically a very challenging role. Many people don't laugh. Many people follow your trajectory 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, at least not suffer? To me it really is about the relationship with the CEO or with the founders because that's sort of the root of a lot of the issues that come out of that scenario because it's not always you like in my story, I think it was primarily about me, but I also work with a lot of founders who are going through really tough things. My clue to people who report to a founder is to say, imagine if you're confused about how your founder is behaving. Imagine that they're terrified all the time and see if that makes their behavior more clear. Because it is scary to be a founder.

Kenneth Berger
Everything's on your shoulders. And I think a lot of people do feel that sense of high stakes all the time. And so I think being real about that, what is the state that the, the person or the people you're working for are in and sort of working within that versus sort of pretending that it's something else or wishing that it were something else is sort of the path to having a healthy relationship. Because if you don't have a healthy relationship with the person you're working for, you're not going to get anything done. You're not going to succeed in any meaningful way.

Lenny Rachitsky
I love that framework of how to think about why a founder is behaving in a certain way. Just maybe a last following thread. There is just what should people look for to help them understand if the founder and them are a good fit, if they're going to have a good time working with that founder? Is 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 in this company as the first PM or not.

Kenneth Berger
I think it's a hard thing to generalize about, but to me it really is about understanding expectations, right. Of like, what do you. I mean, I guess this is a predictable coming from me, but what do you really want? Right? Because I think that often 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 or 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 there's no guarantees, of course, but it gives you a sort of more sure path to having a productive relationship. It's actually something that I recommend to a lot of founders for maybe their first ten or 15 or 20 employees of just have a relationship design conversation with each of them when they're first hired. Because I think a lot of us come in naive the way I did, assuming, oh, yeah, I'm just going to come in and do my thing the way I've always done it is going to be fine, versus coming in and saying, I actually don't know how I'm going to operate at this company. I have range, like anyone has range. And I don't know what this company needs and who else is here, and sort of what my role and what my place is going to be within these other people.

And so by really understanding that intentionally and not from a place of performance management, you're already doing this poorly, you're in big trouble. But a. Yeah. What is the best way to work together, given who we have now and what we want and what we need? Let's figure it out.

Lenny Rachitsky
Coming back to our core topic, is there anything that we didn't cover, anything that I should have asked you about? The skill, the art of asking for what you want, anything else you want to leave listeners with? I do want to mention something that I hear a lot from founders when I talk about the piece of working through resistance, because I think a lot of them say, oh, you want me to let go of fear and focus on what I want? Well, I've been running from fear my whole career. That's how I'm so hardworking and how I'm so smart is I'm always afraid I'm not good enough.

Kenneth Berger
Like, am I going to be able to do this job without fear hounding me every step of the way? And I just, and I just remember the first time I heard this. It broke my heart. And now I've heard it 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 my fear of not being good enough is what drives me to be great. And I just want to come out here and say, there's other ways to motivate. Right? You can motivate based on joy, based on vision, based on your inspiration in this vision of what you want. And I think a lot of folks I talk to are skeptical, understandably, because they've operated a different way their whole life.

And all I can really say is, try it. Try following an inspiring vision that's really meaningful to you and just see what it's like to not be sort of living in fear all the time, because it is. It's a big difference, and it's really meaningful. It matters a lot. So is the idea there, is the fear there that if they ask for what they want, they'll get what they want, and they let go of kind of the drive to prove themselves.

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

Kenneth Berger
I'm sitting in my office in a desk chair. Zoom call. There's no real danger here. And so fear is not particularly functional. And so when they start realizing that, the practice becomes, oh, yeah, I'm feeling afraid, but I'm reminding myself there's not a tiger in the room.

Like, if I really want to sort of get things done, achieve my goals, I need to focus on vision, on what I want to achieve in the world, not on avoiding all these fears. So that's the short of it. Amazing. It reminds me, we have a chat. I had a chat with Matt Mushari, and we spent a bunch of time on dealing with fear and overcoming fear.

Lenny Rachitsky
So folks want to dig deeper there. They could check out that episode. Okay, just maybe one more question before we get to our very exciting lightning round. I want to take us to contrarian corner. Classic contrarian corner.

I'm curious if there's anything that you have a contrarian opinion about, something that you believe that most other people don't. For me, I'm not a big believer in discipline, that I think some folks come to coaching looking for sort of a drill sergeant to say, all right, shout at me and tell me to do better. And I sort of say, yeah, no, that's not how I operate, because it's not that discipline doesn't work, but it's like people pleasing. It's a short term. It's a short term coping strategy.

Kenneth Berger
Like, discipline will get you in the gym for a week, but it's not going to get you in the gym for a year. Right. The people who are in the gym for a year are doing it because they want to. Right. There's actually something that's motivating for them in that that's not just, oh, I hate this, but I'm going to go anyway.

And so I try to be really clear with people about that, that I'm not going to be the drill sergeant because it's unsustainable. Right. Like someone shouting at you, like, is not going to, you know, get you sort of moving towards what you want in life over multiple years. Right. It's a days or weeks or even hours thing.

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

No, but just thank you for letting me share this stuff. It really is my life's work, and I'm very passionate about it, and I hope it's helpful for people. And I'm going to be writing more about it on LinkedIn. Okay, amazing. We'll point people there with that.

Lenny Rachitsky
We've reached our very exciting lightning round. Are you ready? I'm ready. Let's do it. First question.

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

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

Lenny Rachitsky
Sorry for the interruption. Yeah, you have. I mean, you've. I mean, I mentioned before, but I actually took Johnny Miller's nervous system mastery course I just wrapped up. So you've had lots of great personal professional development thinkers on the pod.

Kenneth Berger
So thank you for introducing me to them. I'm so happy to hear that we'll link to that episode as well. I love that. What a circle. Circle of life we've got here.

Lenny Rachitsky
Guests following, other guests taking their courses, joining the podcast. What a happy world. Yeah, indeed. Okay, any other books before we move on? I also love the 15 commitments of conscious leadership, so I'm pretty sure other guests have mentioned that as well.

Kenneth Berger
But to me, part of why I like that is that I think a lot of personal development books are not very directive. They say, oh, you know, just dig deeply and find your truth. And while there is value to that, of course, I think sometimes it's nice to have some direction of, yeah, here's 15 things that, like, generally, your life's gonna be better if you do them. And so 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.

Lenny Rachitsky
Do you have a favorite recent movie or tv show you've really enjoyed? I'm a recent tennis fanatic, so was one of the things I picked up during the pandemic. So I really enjoyed Netflix's breakpoint because it's a documentary on the best tennis players in the world. And it is just. I just find it so, I don't know, it's just beautiful seeing how everyone is kind of the same because all these people, they all know all the strokes perfectly.

Kenneth Berger
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. When they have a narrative that says, oh, I'm behind the other person's better, I'm not going to be able to do this. Are they believing that, or are they working through that resistance and saying, that's just a story I have.

I actually don't know what's going to happen, but I'm going to try to win. I love that you see coaching opportunities in everything, even entertainment. I also love. I mean, actually, 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, this british actor who's this sort of, you know, he's this sort of, you know, tough old sort of, you know, stodgy government office manager, and he gets diagnosed with cancer, and he has this real transformation where he thinks about, God.

I've just been sitting in office filing papers my whole life. What do I actually want to do with the last months of my life? And he builds this playground for children, and that's actually his legacy. Sorry, actually, spoiler alert. Whoops.

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

Do you have a favorite product you recently discovered that you really love? Well, you know, it's funny. I used to be a big wine aficionado, and I think, as with many of us, I am discovering I feel better with less alcohol in my life. And so one of the things I've been picking up is oolong tea. I've got a little cup of taiwanese wenchang baojong in front of me and I feel like it's like all the nerdery that I put into wine of like regions and varietals and history and processing.

Kenneth Berger
But it's actually good for me. It's like full of antioxidants and makes me more focused and I can drink it during the day. And so, yeah, I've been totally going down a nerdy tea rabbit hole and I recommend it. Taiwanese mountain teas especially. I gotta give me some of that.

Lenny Rachitsky
That's actually, I always have tea here when I'm doing these podcasts. I'm a less sophisticated tea drinker. I just go with Earl Grey, but like a really nice Earl Grey. And so I'm gonna have to buy some of this. Do you have a place and a brand you recommend most?

Kenneth Berger
There's lots of great stores online. You can check out tfromtaiwan.com. That's a good one. They're gonna get a bunch of traffic. They're like, what the hell just happened?

Lenny Rachitsky
Tfromtaiwan.com. Amazing. Do you have a favorite life motto that you often come back to find useful? Share with work. Share with friends or family in work, your own life.

Kenneth Berger
I mean, I'm pretty sure you can guess, Wendy. I wonder what it might be. I wonder what it might be. So this is actually part of why I started writing this book, is because my friends were probably annoyed with me telling them, have you asked for what you wanted? Right?

Ask for what you want. Because, yeah, it's the best advice I have, is to ask for what you want. It all just comes back to that final question we've been talking a lot about asking for what you want. Kenneth Berger, what do you want? All right, well, I think for me, Lenny, you are already an industry luminary with thousands of followers.

I'm interested in sharing more of these ideas. If you all would come follow me on LinkedIn, subscribe to my newsletter. I'm going to be exploring these ideas and sharing more of this stuff because I just am so passionate about it. And yeah, I'd love if you'd come and join me in that journey, bring questions and ideas, and I'd love to talk about this stuff because I just find it endlessly interesting. But you're working on a book along these lines.

Lenny Rachitsky
At some point that will come out, right? That's right. That's right. So, yeah, so I'm working on it in book form, but part of what I've been doing is I realize I want to work on it in community. Right.

Kenneth Berger
Speaking of asking what you want. Right. I mean, for me, it's not just about my vision and my framing, but like, I'm a coach, right? Like, I'm not just about big ideas. I'm about making a difference for my clients.

And so I realized, yeah, if I really want to make a difference with people, I need a product. I need to get out in the world and test out these ideas and see what lands with people and what's effective for them and what works and hear the stories and sort of really get into it. So that's kind of why I've been putting myself more out there. Amazing. So kind of along those lines, two last questions.

Lenny Rachitsky
Where can folks actually find you online and follow the stuff that you're writing? And how can listeners be useful to you? So you can find me on LinkedIn. I'm Kenneth Berger. B E r g e R.

Kenneth Berger
So please follow me there. Subscribe to the Ask for what you want newsletter, and yeah, you can check out my website, kburger.com. Kberger kburger.com dot. Kenneth, you're amazing. Thank you so much for sharing so much wisdom with us.

Lenny Rachitsky
I think we've helped a lot of people. Thank you for being here. Thank you. Bye, everyone. Thank you so much for listening.

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

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1. Introduction

2. Understanding Personal Barriers

3. Tactical Advice

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