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

The cost of staying silent

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

The need to be right

Kenneth Berger: 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.

Lenny Rachitsky: What we’re going to be talking about today is your personal magnum opus, the output of 10 plus years as a founder and operator and seven plus years as a coach.

The high-pressure trap

Kenneth Berger: 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.

Speaker 3 (00:00:30): You’re hired.

How to know what you want

Lenny Rachitsky: How do you know that this is something you need to be working on?

The dreams behind complaints

Kenneth Berger: 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?

Being specific about what you want

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

The fear of hearing no

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 10 years in tech before transitioning into coaching. His core focus with leaders is to help them learn how to ask for what they want. This sounds really simple, but as you’ll hear in our chat, this one skill is at the core of so many of the struggles that people have in their career and in their life.

Kenneth shares a ton of very tactical advice to help you figure out what it is you want, how to overcome the resistance that comes with asking for what you want, how to actually ask for what you want effectively, why the most important step is hearing the response that you get when you ask for what you want and all of the things that will change in your life if you get better at this one skill.

Kenneth also shares the story of him being fired three times from Slack, which is hilarious. With that, I bring you Kenneth Berger after a short word from our sponsors. And if you enjoy this podcast, don’t forget to subscribe and follow it in your favorite podcasting app or YouTube. It’s the best way to avoid missing feature episodes and it helps the podcast tremendously.

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Kenneth, thank you so much for being here. Welcome to the podcast.

Kenneth Berger: Yay. thanks for having me.

A three-step process: express, ask, accept

Lenny Rachitsky: I love that, yay. 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. What we’re going to be talking about today is something that you described to me as, quote, your personal magnum opus, the output of 10 plus years as a founder and operator, and seven plus years as a coach to startup leaders.

And the core idea is simply asking for what you want, which sounds really simple. So let me just start broadly just why have you found that this skill, this one idea is so core to so many of the challenges that people run into in work and in life?

From control to true desire

Kenneth Berger: If I had to answer in one word, it would be integrity. I think that it’s one of these funny things where everyone thinks they already know how to ask for what they want. 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 fool ourselves a little bit. When it comes to are we really pursuing the things that we want in life? 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 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 expecting the nose 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 fooling ourselves that we’re actually moving towards of what we want.” There tends to be all these unexpected secondary and tertiary effects that come out of that 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, of what’s important in achieving our purpose.

Techniques to identify your desires

Lenny Rachitsky: What are just some challenges that people have in their life and career that are just rooted in doing this badly? Not asking for what you want, not knowing what you want.

Kenneth Berger: For me with clients, I think what I’m often looking for are just kind of this sense of being stuck because everybody has 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.

So 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 sort of iterative development discovery process?

So I think that stuckness is one thing. And I think the other thing I look for is interpersonal conflict, right? Because I think that one mode of not asking for what you want well is holding back and not really saying it out loud. I think another really common mode is coming with a lot of entitlement of, “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, that’s a really disrespectful way to come into the conversation and it’s an obvious source for a lot of issues.

Making intentional requests

Lenny Rachitsky: 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?

The cost of unspoken needs

Kenneth Berger: There’s so many examples. I think we will eventually get into the story of how I 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 get into this boat. 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, 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.

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. 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.

Asking when you lack power

Lenny Rachitsky: I think you may have already answered this question, but I think it’s really important is how do you know that this is something you need to be working on? How do you know like, “I really need to pay attention to what Kenneth is about to tell me?” You said one is you feel you’re stuck in your career, something you’re just not making progress, and this could be the answer. Or you said there’s interpersonal conflict and you’re just having a lot of conflict with people. Are those the two answers? Are there more?

Relationships trump data

Kenneth Berger: I think those are great things to look for. I think it’s also good to look for a sense of things being high stakes, because I think part of what can create a lot of conflict and difficulty in these situations is a sense of this is life or death. And that was certainly how it was when I was a founder 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 easy going. 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. And 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, that can get us really focused on the fears rather than focused on the goals.

Complaints signal unspoken needs

Lenny Rachitsky: There’s a question I was going to save for later, but it’s something that’s very top of mind for me is knowing what you want. How do you know what you want? There’s basically knowing what you want and then asking for what you want. I like equanimity in my life, and so I often don’t ask for what I want or push down maybe what I want, or I don’t think about what I want. I just want other people to be happy.

I’m curious what people can do and what I can do to get better at knowing here’s what 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?

Embracing all parts of yourself

Kenneth Berger: Well, first of all, I’d say you’re very far from alone there. 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 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 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?”

So the magic of that complaining is that every complaint implies a dream. 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 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?”

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 a hundred percent 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, “Ah, I don’t know if that’s quite my dream.” 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 find that middle ground where, “Yeah, this dream is hard. I don’t know that I’m going to get it, but, damn, it’s worth trying. I want to go for it.”

Lenny Rachitsky: I love that for someone that wants to try this on their own and help themselves get better at this without you being there, what is it that you do? Is it you dream about what would make you happiest? Is it 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.

The transformative T-Group experience

Kenneth Berger: Specifically for articulating what you want because that’s the first step of the asking for what you want process. It really is as simple as that 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 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 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. 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.

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? What does that mean? How am I going to feel?

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.

Lenny Rachitsky: Okay. You’re getting into where we’re going to go. Before we get there. Final question. This idea of dealing with, no, I think this is the other big blocker for people is like, “Oh, that’s so scary to ask for something I really want or ask for something big that is really important to you.” What is it that you advise there of just getting over this fear of just asking for what you want?

Step three: accepting the response

Kenneth Berger: 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. Because you really want enthusiastic consent. Not just, “Maybe, kinda. I’ll try. We’ll see. But yeah, absolutely, let’s do this.” 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 short of a hell yes. And then we realized later on, “Oh yeah, they weren’t really in.”

They didn’t show up to the party or they didn’t deliver on time because my CTO said, “Yeah, I think maybe we can deliver by May 1st.” And then May 1st comes and surprise, surprise, your milestone is not done because you didn’t go for that hell yes. And so I think part of what I encourage people to do is, one, to really hear anything short of a hell yes as a no. So it’s not a bad thing. Mostly the world tells us 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 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 you’re lukewarm on May 1st as 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, “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?”

Lenny Rachitsky: 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? What would it take for you to just agree to this? It’s more a hell yes. And your point there is hell yes is when they actually fully agree. Oftentimes people kind of like, “Yeah, yeah, yeah, yeah.” And then they don’t actually follow through.

Getting fired from Slack three times

Kenneth Berger: Some people call this a whole body yes because sometimes your head is saying yes, but your heart is saying no 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 getting like aligning a deadline. I imagine the same skill applies to everything in relationship questions and friends and family and work.

What I would do differently

Kenneth Berger: It does. And 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. We all know the numbers on that. And so to me, there’s a perspective you have to take if you’re going to operate in the startup world of being okay with not knowing that you’re going to get the outcome you want. A lot of people, we operate in a safer world where we’re more clear exactly what the outcomes are going to be, but if you’re a startup founder, you’ve got to be okay with, “I’m just going to go for this, and I know I probably won’t get it. But it’s so meaningful to me, I’m going to go for it anyway.”

And so to me, that’s not just about the big picture of running a startup, it’s about really anything you might want in life, because that’s such a useful perspective to say, “I know I’m not going to get it. I know I’m not guaranteed to get it. I’m not going to be attached to that. I know people aren’t obligated to tell me yes, but I’m going to go forward anyway because I want it and that’s enough.”

Advice for first-time PMs

Lenny Rachitsky: So let’s actually get into the skill of learning how to actually ask for what you want more effectively. You already described three steps, so maybe just describe them again and let’s just walk through them.

Kenneth Berger: The first step is articulating what you want. And we’ve gone into this a little bit, but to me, I think that the key places that people tend to have missteps here, or one in this phrase, it’s fine. I think of the “it’s fine” cartoon with the flames 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. I actually, I don’t need anything. I’m good.”

And again, this is tempting, right? Because it’s so nice to have this idea that I’m fine, I don’t need anything. And in a certain way, that’s a nice attitude because yeah, 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 that do is to really tune into the parts of them that maybe aren’t so fine like, “Gosh, I’d prefer it a little bit if things were this way or yeah, I’m a little bit bothered by this, or I’m a little bit nervous about this.”

And so kind of tuning more into those subtle emotions that are pointing them towards, “Sure, I’m okay with the status quo, but I 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.

So for those folks, it really tends to be more about saying it out loud. Once you say it out loud, it is clearer. 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. 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 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 we’re just ready to go for it and we’ve got each other’s backs.”

That doesn’t mean we agree with each other all the time or that we’re a hundred percent 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 is going to agree.

Designing relationship conversations

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

Fear isn’t the only motivator

Kenneth Berger: To me a lot of the classic examples are around feedback. Because I work with a lot of founders who are not the sort of classic control freaks. They’re super nice and their teams love them and they love their teams. So 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 no is that, “Sure, they can always say no. Everybody gets to say no whenever they want, but there are consequences.” 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 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 of being so kind and of people loving me.” And it’s like, “Well, that doesn’t mean that there aren’t consequences for their actions.”

Part of really respecting them is respecting that they can make the choices they want and they’re grownups enough that they can deal with the consequences of those choices.”

The counterintuitive corner

Lenny Rachitsky: Can you even get more concrete there? Is it we need to hit this date, or are there going to be big problems? Or is it like, “I need you to hire this large of a team?” I don’t know. What is it that they’re not articulating that they later realize, “Oh, here’s what I need to articulate.”

Kenneth Berger: 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. 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. I understand that might be disappointing or frustrating or what have you, but part of the expectation for this role is that you can roll with disagree and commit sometimes when that’s necessary.”

Lightning Q&A round

Lenny Rachitsky: That’s an awesome example. I fully get that and I could see how scary that is to a lot of people. One is just 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.” 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 this changed, I’d be happier.” Or things would probably run better. That’s a really cool example of how to think do that because easy, just like, “Oh yeah, if we 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?

My top recommendations

Kenneth Berger: It always comes back to integrity. And a great way to do an integrity check is to just look have I fully expressed myself? And so I think we’ve talked a little bit about charting your feelings as a piece of that 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 expressed those in whatever way is appropriate, then probably I’m not fully in integrity.

I think saying what you have to say is a piece of that too. “Gosh, is there something that I keep thinking about and I’m just like three or four days, I’m just like, man, I really want to say this to this person.” At this point, you’re probably out of integrity because there’s something deep in you that really needs to say this, right? And so to me, articulating what you want is really about mindfulness is about checking for all these things.

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 that 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.”

Lenny Rachitsky:

Okay. This is a great segue too. 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?

Sharing and community

Kenneth Berger: So for asking what you want, I think the really important tweak here is asking intentionally because I think a lot of us are 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 more in the control-free 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. Of course, it’s obvious from an effectiveness standpoint, it’s not working well, but they more just haven’t embraced that you can do it a different way that they only really see one way of doing it.

So part of asking for what you want effectively is really just recognizing the rut that you get stuck in and working through all those narratives that make us resist asking it a different way. 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?”

So these are all very common things that people go through, but then they end up not actually asking for what they want. Now, actually expressing who they are and what they stand for in the world. And that has a really serious cost. 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 at our eulogies.

The final question

Lenny Rachitsky: No. That’s good motivation. Okay. So say in this example you gave of like, “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 the way you communicate it? Is it something else? How do you actually do this without pissing people off and also just risking too much?

Kenneth Berger: Even implicit in that question, to me that’s that question of, “Oh, how do I do it without being any risk of ever pissing anyone off?” 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 work 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 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 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.

So part of asking for what you want effectively is actually bringing some compassion for yourself. Of course, we all want to be sure that the way we ask is going to be effective and no one is going to be mad at us and we’re going to get all of our dreams come true. But we don’t get that. I wish we did. That would be nice. But is that worth not pursuing your dreams in life?

Lenny Rachitsky: Such a good point about what you identified and the way… I think a lot of people that think about it, it’s just like, “I’d always do this without causing anyone any pain or risking anything going wrong.” I think that’s, to your point, part of it. So you talk a lot about founders. You work with a lot of founders, a lot of listeners here are not founders, they’re product managers, ICs on teams, other functions that don’t have “power”. Is there anything that you suggest these folks do differently or think about this differently or is it kind of the same thing? In the end everyone has power in some way. How would you think about this if you’re just, 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 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. 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. So what do you think? Are you willing to reconsider this?”

Lenny Rachitsky: That’s such a great approach. It’s 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. People actually care about your opinion and you could actually change things. But just telling them, “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?

Kenneth Berger: You’re giving me deep goosebumps because I think this is a really underappreciated thing in terms of asking for what we want because especially in the PM world, we’re trained to look for data. We’re not just going to state an opinion. We’re going to say, “Oh, the AB 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. You have some sort of 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.”

Lenny Rachitsky: Do you find that that’s actually a crutch a lot of times to people not saying anything is they don’t have that data? They don’t have evidence and they just, “I shouldn’t say anything. If someone asks for why I don’t have a great answer, I just think this is what should be.”

Kenneth Berger: Totally. And I think there’s a balance there as with anything. Is ignoring data and going in gut all the time, great? Probably not, right? We use data for a reason, but I think there are all these moments when we are making a gut decision and having all the data there means having the opinion set out loud. I think often the dangers of people saying, “Oh, I don’t have data to back this up. It’s just what I think. And I’m not sure people are going to agree with me, so I’m just not going to say it.”

So 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.

Lenny Rachitsky: 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 like, “I knew this project was going to fail. I knew this was a terrible deadline. I knew this design was not great.” Anything more you want to say along those lines of just like, “If you’re not asking for what you want, complaining is often a sign that you should be doing that more”?

Kenneth Berger: To me, complaints are great inspiration. To me, I love radical candor, for example, where I try to go a step further than radical candor is to not just say, “Hey, here’s my feedback. Just wanted you to know.” But to say, “And I want something. I would like to see an outcome.” And so I think that to me it’s all about the effective framing that 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 don’t like that whiny part of myself. I’m just going to push that one down versus actually taking what it has to say as important data.”

Lenny Rachitsky: That’s a really good point. I think that’s actually another blocker for a lot of people is just, “I don’t want to be a complaining person. I just want to be like, let’s do this. I’m in, let’s go. I don’t want to be seen as a squeaky wheel.” Is there anything you say there about as a resistance point for people?

Kenneth Berger: 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. 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, and I don’t respect that part of me as much.” 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, then we’re going to stay stuck.

Versus if we come in and say, “Hey, buddy, why are you scared? You seem terrified. What’s going on? Oh, well man, you think your whole professional reputation has 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, “I know that’s scary, but we also know that’s not really true. You’re not an imposter, right? You’re an experienced professional.”

Lenny Rachitsky: Man, there’s so many threads we can’t follow here. This whole line of internal family systems, right?

Kenneth Berger: Mm-hmm.

Lenny Rachitsky: That’s its own podcast episode potentially. And then imposter syndrome, we’ve touched a bunch of different podcast episodes, but I’ll avoid going in that direction. Something you reminded me of is we just had Carole 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 T-Group Weekends, summer of 2020, I think a month after George Floyd was murdered and was facilitated by a black woman. And it was one of the most profound transformative weekends of my life. Because T-groups already people rave about them. But having it at that point in history with those people in the room, oof.

Lenny Rachitsky: A lot of tears, I imagine.

Kenneth Berger: 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 is the broader umbrella term. And Carole talked about it. Everyone that has gone through it, 100% have told me that it’s a transformative life experience for them. And you had a bonus transformational piece. So anyway, if people want to check out that episode, I will include it in the show notes. But the reason I brought it up is Carole 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 like say actual feeling word not like, “I feel like, or I feel that,” blah, blah, blah. And step three is, “I’m telling you this because…” and then what you want them to change. Do you find that sort of approach helpful?

Kenneth Berger: I do. I teach the same thing. I think sort of Carole’s approach and nonviolent communication, DBT teaches a similar approach. They call dear man.

Lenny Rachitsky: To me, what’s DBT?

Kenneth Berger: It’s a dialectical behavioral therapy. It’s related to CBT. So there’s kind of rough consensus in the sort of personal development world of how to ask. And really what they have in common is around staying really factual because I think that 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. Maybe we can trust our eyes. What would a video camera have recorded? And that’s about it.

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? No. 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?

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

Lenny Rachitsky: So far, they’re all tricky to me.

Kenneth Berger: Oh yeah, they’re all tricky, for sure.

Lenny Rachitsky: The most tricky.

Kenneth Berger: But step three is accept the response. And it might seem so simple, 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. 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.” If someone made this face, that’s a no. It doesn’t matter what comes out of their mouth. And so the challenge of accepting the response is often that of hearing the no, but not over accepting or under accepting it.

Because I think sometimes 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. My dream is dead and nothing is ever going to happen for me again.” And that’s because they get so scared. But actually no, that’s over accepting. The no is just from this person right now in the way that you asked, 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, in that sort of more control freak mode, I think for them they’ll often skip over the response say, “Well, 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. So these are all fundamentally disrespectful ways to operate in this relationship. When we’re talking about asking for what we want, we’re talking about influence. So you need to have good relationships. You can’t be influential with a bad relationship.

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 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 no’s, it can actually be more influential, more motivating. If someone says, “Okay. 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 no at face value. And they say, “Oh gosh, well, I didn’t realize that was going to be the consequence. Maybe I can get it done by that time.” And so that way you’re not forcing them and you’re not coercing them, right? You’re just saying, “No, you said no? So that your no is no, and I accept that.”

Lenny Rachitsky: So it feels like part of the skill here is preparing, is knowing. Some people just say no and that’s okay. That’s part of the experience. Part of it is if there’s this not yet component… We had Mihika Kapoor on the podcast. She has a PM at Figma and she had this really great approach to building new things within companies is just like everything to her is not yet and no is a not yet. And the way you phrased it is it could just be the way you asked. It could be, 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?

Kenneth Berger: Acceptance of the response is primarily an emotional regulation issue because once we get our emotions intact, it’s just, is it yes or is it no? And if it’s no, which it probably is, 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. 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, and it doesn’t need to be something so scary or awful.

Lenny Rachitsky: 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, or your own career.

Kenneth Berger: 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 who would be the record-keeping body for this. But now 10 years on, I have different perspective, of course. And so this was almost exactly 10 years ago, spring of 2014 and I just gotten the job as the first PM at Slack. It was already the hottest thing out there. It was only a couple dozen employees.

I came in excited, but also a little insecure because I had just come off my breakup with my co-founder. I just wanted to put my head down and do a good job. I was engaged at the time, so Slack already knew I was going to be going away on a bachelor or backpacking trip. I have a wedding and honeymoon in the fall. And so I came in naive and overconfident of, “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.”

So instead of getting really clear on what does success look like here or what’s your culture or 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’d kind of been in the trenches reinventing from the game to Slack. They’d been through layoffs, really hard times together. So they wanted someone to come in humble and to earn their trust of this kind of core team that had been together for years.

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. 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. 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. I loved this job, I love this company, so I profusely apologized. I said, “I’ll do whatever it takes. I’m so sorry. 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, 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 of 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 be successful, build a great product. I had a year of one-on-ones with the CEO.

I never, never ever asked for what I wanted. I never said it out loud because I was scared. I was scared of what the consequences were. I knew there were a hundred PMs 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.” And so I held all that fear and all those desires of, “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 didn’t work very well. I was feeling horrible day to day. I was terrified of this guy I was working for. And so again, I shouldn’t have been surprised, but I was, when I got fired for the second time. It wasn’t quite firing. But this time I’d 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. We’re actually just going to get rid of product. You’re going to be user research. It’s going to be fine.”

And for me, 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.” So I wrote a proposal, I sent it around to the management team. Turns out, when you actually ask for what you want out loud, you’re much more likely to get it.

And so within a week, this new plan had traction with the management team 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 sit in. I was like, “Am I even any good at this? Should I even be in product management? Am I ever going to work in this industry again? Is this going to be my dark secret that I take to the grave that Stewart Butterfield fired me three times?”

I think what I couldn’t be with in that moment was the no’s, because I was getting no after no after no after no from Stewart and the rest of the management team saying, “What you’re doing is not working for us, right? Your ask are not landing. You’re not being effective in the way that you want to be effective.” And because I wasn’t able to hear those no’s again, because to that emotional regulation standpoint, I couldn’t handle the feelings of like, “Ugh, 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, he’s not such a great manager. He’s not so good at product. I’m the one who was on the ground with the users. I know what’s right.” Against all evidence to the contrary, by the way, is this product luminary, visionary, famous person.

So clearly not based on any facts, but it was an emotional issue of 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 no’s. 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. Never saying what I really wanted, how I really felt because it didn’t feel safe. I was too scared. I kept it all inside. And it took me six months or a year even after that to really feel safe and okay again. It was a serious decompression time.

My wife and I had a baby during that time. I was on zero sleep. It was a rough, rough period. But the irony is that when I actually came out of that experience, the reality of it was extremely simple. I hadn’t articulated what I wanted. I hadn’t asked for what I wanted. I had not listened to the no’s in response to my non-ask.

And so of course I was unhappy with the result. Why would I have expected anything different? I wasn’t the victim. Stewart wasn’t the villain. It was just ineffective asking. And so to me, especially because I was already on that path towards coaching, that lesson hit really hard in terms of how do we make this work more sustainable?

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. 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 your desires. No, it’s real life stuff of a year of suffering, of pain, of fear.” I don’t want other people to be going through that and that’s why I’m so passionate about this stuff.

Lenny Rachitsky: Wow, what a story. I love that it’s kind of a microcosm of everything we’ve talked about. You’ve did all the things that you teach people to avoid.

Kenneth Berger: Exactly.

Lenny Rachitsky: And I think what’s interesting is you went through these three phases. Interestingly, at the beginning, your first phase was you were not hearing the no’s, but it was rooted in this confidence that you’re a founder, you’re awesome. They’re so lucky to have you. I know what I’m doing, get out of my way. And then the third phase, you also, the issue there was you weren’t hearing the no’s, 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.

Kenneth Berger: Totally. 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.”

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, “Ooh, yeah, maybe I need to look at this more closely.”

Lenny Rachitsky: 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’ve happened? Do you think you would’ve stayed there for many, many years, had a product at Slack at this point? Just imagining that reality, what would you have done differently? And then what would you have imagined have turned out?

Kenneth Berger: Well, I mean obviously broadly, I would’ve asked for what I wanted and what I wanted was I wanted to do the best work of our life. I wanted to have a deep professional partner in the CEO and the rest of the product and management team. And I wanted to produce great work that people loved. 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 is of course, that’s what I would’ve done. Now, do I know what the outcome would’ve been?

No, I might’ve been fired even sooner. They might’ve said, “No, this is not working out. Let’s just be done here.” So that’s what’s tricky about this is it really isn’t about the outcome. Of course, asking for what you want makes you more likely to get the outcome you want, but you don’t do it for guarantee of a certain outcome because no one can promise you that. You do it so you can stay in integrity with yourself and not suffer through all this. Because at least then I would’ve said, “You know what? It didn’t work out. At least I’m not sitting here suffering. I can get another job at another startup. It’s not the end of the world.”

And I think that the mistake we make is pretending that it is of saying, going into fight or flight and saying, “This is a severe existential threat to who I am and my safety in the world,” versus being like, “I’m disappointed. I wish it had worked out, but it didn’t.”

Lenny Rachitsky: That’s a really profound point that this practice isn’t necessarily to just have everything work out beautifully and to get the things you’re looking for. It’s to feel like you did, which you could have and to feel integrity with yourself that you did what you needed to do and you’re not going to regret something down the road.

Kenneth Berger: Indeed.

Lenny Rachitsky: I’m going to take a quick tangent down the being the first PM route real quick. There’s a lot of people that think about being the first PM at a startup join as the first PM. I imagine you work with people asking for advice along these lines. It’s classically a very challenging role. Many people don’t last. Many people follow your trajectory where it’s like, “Oh, shit. What have I done?” Any advice for people that are a first PM at a company or startup or thinking about that role?” What can you tell them to help them be successful or at least not suffer?

Kenneth Berger: To me, it really is about the relationship with the CEO or with the founders because that’s the root of a lot of the issues that come out of that scenario because it’s not always you. 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. Everything is 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 of what is the state that the person or the people you’re working for are in and sort of working within that versus sort of pretending that it’s something else or wishing that it were something else is 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. I guess this is a predictable coming from me, “But what do you really want? 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 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 more sure path to having a productive relationship.

It’s actually something that I recommend to a lot of founders for maybe their first 10 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. It’s 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 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?

Kenneth Berger: 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 mean, I’ve been running from fear my whole career. That’s how I’m so hard-working and I’m so smart is I’m always afraid I’m not good enough.”

Am I going to be able to do this job without fear hounding me every step of the way? 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. You can motivate based on joy, based on vision, based on your inspiration in this vision of what you want. I think a lot of folks I talk to are skeptical understandably because 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 living in fear all the time because it is a big difference and it’s really meaningful. It matters a lot.

Lenny Rachitsky: So is the fear there that if they ask for what they want, they’ll get what they want and they let go of this drive to prove themselves? And is that the fear? How is it that they move away from that need to prove themselves?

Kenneth Berger: Well, I mean that’s a longer story. I would say 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’d 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.” I’m sitting in my office in a desk chair on a 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. If I really want to 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.

Lenny Rachitsky: Amazing. It reminds me, we have a chat… I had a chat with Matt Mochari, and we spent a bunch of time on dealing with fear and overcoming fear. So folks want to dig deeper there. They could check out that episode. 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.

Kenneth Berger: For me, I’m not a big believer in discipline that I think some folks come to coaching looking for a drill sergeant and say, “All right. Shout at me and tell me to do better.” And I start to say, “That’s not how I operate.” Because it’s not the discipline doesn’t work, but it’s like people-pleasing. It’s a short-term coping strategy. Discipline will get you in the gym for a week, but it’s not going to get you in the gym for a year. The people who are in the gym for a year are doing it because they want to.

There’s actually something that’s motivating for them in that. It’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. Someone shouting at you is not going to get you moving towards what you want in life over multiple years. It’s days or weeks or even hours thing. And so I really look for a higher bar to say, “Let’s look for true long-term sustainable motivation,” which means relying on vision, pursuing what you want.

Lenny Rachitsky: 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.

Kenneth Berger: I am a broken record admittedly.

Lenny Rachitsky: Amazing. Kenneth, is there anything else you wanted to share or leave listeners with before we get to our very exciting lightning round?

Kenneth Berger: 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. I’m going to be writing more about it on LinkedIn.

Lenny Rachitsky: Okay, amazing. We’ll point people there. With that, we’ve reached our very exciting lightning round. Are you ready?

Kenneth Berger: I’m ready. Let’s do it.

Lenny Rachitsky: First question, what are two or three books that you’ve recommended most to other people?

Kenneth Berger: Well, I already mentioned Radical Candor. I think that is for sure a modern classic and I think that whole idea of challenging directly, but caring personally is very much aligned with what I’m talking about, right? Because you need the relationships and you need to actually speak your truth. So I love Kim Scott’s writing on that stuff.

Lenny Rachitsky: We had a Kim Scott on the podcast. Folks want to dig deeper there. We’ll link to that episode. I’ll let you keep going. Sorry for the interruption.

Kenneth Berger: Yeah. I mean I mentioned before, but I actually took Jonny Miller’s Nervous System Mastery course. I just wrapped up. So you’ve had lots of great personal professional development thinkers on the podcast, so thank you for introducing me to them.

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

Kenneth Berger: Yeah, indeed.

Lenny Rachitsky: Okay. Any other books before we move on?

Kenneth Berger: I also love the 15 Commitments of Conscious Leadership, so I’m pretty sure other guests have mentioned that as well. But to me, part of why I like that is that I think a lot of personal development books are not very directive. They say, “Oh, 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, “Here’s 15 things that generally your life’s going to 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. Try this stuff. It works.

Lenny Rachitsky: Do you have a favorite recent movie or TV show you’ve really enjoyed?

Kenneth Berger: I’m a recent tennis fanatic, so it was one of the things I picked up during the pandemic, so I really enjoyed Netflix’s Breakpoint because it’s a documentary on the best tennis players in the world. I just find it so… I don’t know. It is just beautiful seeing how everyone is the same because all these people, they all know all the strokes perfectly. They’re technically perfect in pretty much every way. And so it really is mental.

For those folks, it is about working through resistance as well. When they have a that says, “Oh, I’m behind. The other person is 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.”

Lenny Rachitsky: I love that you see coaching opportunities in everything even entertainment.

Kenneth Berger: I mean actually speaking 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 is this sort of tough, old sort of stodgy government office manager, and he gets diagnosed with cancer. And he has this real transformation where he thinks about, “God, I’ve just been sitting in an office filing papers my whole life. What do I actually want to do with the last months of my life?” And he builds this playground for children, and that’s actually his legacy. Sorry, actually, spoiler alert. Whoops, should’ve.

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 just for anyone listening right now, just to give you a heads up.

Kenneth Berger: Awesome.

Lenny Rachitsky: How fun is that going to be? Okay, next question. Do you have a favorite product you’ve recently discovered that you really love?

Kenneth Berger: Well, 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 [foreign language 01:09:51] in front of me, and I feel like it’s all the nerdery that I put into wine of regions, and varietals, and history and processing, but it’s actually good for me. It’s like full of antioxidants and makes me more focused and I can drink it during the day. I’ve been totally going down a nerdy tea rabbit hole, and I recommend it. Taiwanese mountain teas especially.

Lenny Rachitsky: I got to give me some of that. 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 a really nice Earl Grey, and so I’m going to have to buy some of this. Do you have a place in a brand you recommend most?

Kenneth Berger: There’s lots of great stores online. You can check out teafromtaiwan.com. That’s a good one.

Lenny Rachitsky: They’re going to get a bunch of traffic. They’re like, “What the hell just happened?” Teafromtaiwan.com amazing. Do you have a favorite life motto that you often come back to, find useful, share with friends or family and work around life?

Kenneth Berger: I mean, I’m pretty sure you can guess, Lenny.

Lenny Rachitsky: I wonder what it might be. I wonder what it might be.

Kenneth Berger: 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? Ask for what you want.” Because yeah, it’s best advice I have is to ask for what you want.

Lenny Rachitsky: 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?

Kenneth Berger: Ooh. All right. Well, I think for me, Lenny, you are already an industry luminary with thousands of followers. I am interested in sharing more of these ideas. So if y’all would come follow me on LinkedIn and subscribe to my newsletter, I’m going to be exploring these ideas and sharing more of this stuff because I just am so passionate about it. 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.

Lenny Rachitsky: But you’re working on a book along these lines at some point that will come out, right?

Kenneth Berger: That’s right, that’s right. I am 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. Speaking of asking for what you want, I mean, for me, it’s not just about my vision and my framing, but I’m a coach. I’m not just about big ideas. I’m about making a difference for my clients. And so I realize, if I really want to make a difference with people, I need… It’s like a product, I need to get out in the world and test out these ideas and see what lands with people and what’s effective for them and what works, and hear the stories and really get into it. So that’s kind of why I’ve been putting myself more out there.

Lenny Rachitsky: Amazing. So along those lines, two last questions. Where can folks actually find you online and follow the stuff that you’re writing and how can listeners be useful to you?

Kenneth Berger: So you can find me on LinkedIn. I’m Kenneth Berger, B-E-R-G-E-R. So please follow me there. Subscribe to the Ask for What You Want newsletter. And you can check out my website, kberger.com, K-B-E-R-G-E-R.

Lenny Rachitsky: Kberger.com. Kenneth, you’re amazing. Thank you so much for sharing so much wisdom with us. I think we’ve helped a lot of people. Thank you for being here.

Kenneth Berger: Thank you.

Lenny Rachitsky: Bye, everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcast, Spotify or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcasts.com. See you in the next episode.

Glossary

English	中文
CBT	认知行为疗法（CBT）
Coaching	Coaching（教练辅导，保留原文）
control freak	控制狂
DBT	辩证行为疗法（DBT）
DEAR MAN	DEAR MAN
disagree and commit	求同存异、全力执行
dream behind the complaint	抱怨背后的梦想
entitlement	理所当然感
fight or flight	战斗或逃跑
hell yes	”太好了”（热情的、全身心的同意）
imposter syndrome	冒名顶替综合征
integrity	一致性
Internal Family Systems	Internal Family Systems（内部家庭系统）
lukewarm	冷淡
mindfulness	正念
Nonviolent Communication	非暴力沟通
people pleaser	讨好型人格
PM	产品经理（首任 PM = 首任产品经理）
radical candor	radical candor（彻底坦诚）
relationship design conversation	关系设计对话
resistance	阻力
T-Group	T-Group
touchy-feely	touchy-feely
whole body yes	全身心的同意

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Reformatted by reformat_english.py