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

For me, the impact was about making this work sustain. So that we're not burning out or selling out, but actually able to pursue these hard goals that we have and start up.

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

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

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 run. Like, we all ask for what we want. We order our coffee in the morning. And we all think we have integrity. You know, when walks around thinking, I'm lying to myself all the time or lying to others, certainly. And yet, we tend to kind of fool ourselves a little bit, right? You know, when it comes to, are we really pursuing the things that we want in life, right? And I think, to me, the flip side of that is sort of the reason that the stakes around asking for you want are so high. Because, yeah, you know, if you're, we can't guarantee we're going to get one. 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 kind of get the sense of, yeah, I'm honoring what's important to me, I'm honoring the world response, and I'm moving forward to this one. And if we don't do that, well, then we're kind of fooling ourselves that we're actually moving in charge of what we want. There tends to be all these sort of unexpected secondary and tertiary effects that come out of that, right? Stress and frustration and unhappiness because, of course, asking for what we want pursuing what's important to us in life is just one of the most important things of fulfillment, right? Of what's what's, you know, important in sort of achieving our purpose.

For me with clients, I think what I'm often looking for is kind of the sense of being stuck, right? Because everybody's got frustrations, everybody gets nervous at work sometimes. But if we're in the same stuck place week after week after week and our coaching sessions, probably you're trying the same thing and not getting any different results, right? It's sort of that definition of insanity thing. And so, really, I look at that and say, okay, you know, maybe you're asking for what you want. right, maybe, although often people aren't. But even if you are, you're probably not achieving it, right? You're not getting the results you want. So why aren't we not learning from now? Why aren't we not sort of moving forward, getting new data, trying something new, actually treating it as a sort of iterative development discovery process? So I think that stuckness is one thing. And I think the other thing I will force interpersonal stuff, right? 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. If 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, in a original cod point, even if you are, they're boss, right? That's a really disrespectful way to come into the conversation. And yeah, it's obvious source for a lot of issues.

There's so many examples. You know, I think, you know, we'll eventually get into the story of how is fired from Slack. But I think for me, you know, the thing that always came up was just being attached to being right. And I think a lot of us sort of get into this boat. If we enter into a meeting and we're sure from the first moment, I'm right and they're wrong. And I think that especially in product management, right? Like we're supposed to be the holders of this vision for what the product should be. And so it's easy to come in with a lot of conviction and not really a lot of openness to other ideas. And sort of often when I try to introduce people to and I, you know, learned all this stuff the hard way, believe me, is it's fundamentally disrespectful to go into a meeting already deciding that you're right in the other person as well. because you can't know that for sure, right? There's always a new perspective, new data that could come in, and so you want that conversation to really be a back and forth. And if you're coming in with this really ingrained sense of righteousness, you can't do that. There's no way to have that conversation respect.

Right? Because I think part of what can create a lot of sort of conflict and difficulty in these situations is a sense of, this is life for death, right? And that was certainly how it was when I was a founder, right? Okay, normally, you know, when I was a Adobe, it's a big company, and they're going to be fine, either way, no matter what I do, right? I can be easygoing, you know, let someone else have their way in the meeting, but when it was my company, When it was my vision on the line, I didn't feel especially flexible, right? The stakes seemed really, really high, right? This is the success of my idea, my vision, my reputation is on the line. And so I think often when the stakes feel high, we're kind of focused more on the fear of what we don't want to happen than on actually achieving what we do want. Right? And that's a really critical distinction, right? Because, you know, if we're running away from our fears, it doesn't necessarily mean we're getting anywhere meaningful for what our desires are. And so that that sense of high stakes that often we can get, whether it's in interpersonal conflict or being afraid of asking if what we want, that can get us really focused on the fears rather than focused on the goal.

Well, first of all, I'd say you're very far from alone there, right? I mean, I think the people, please are coping strategy is one of the most classic. And it is effective, right, in the short term, right? Like, you can feel safe and calm when other people are generally happy with you. And the cost tends to be long term, right? In terms of am I really pursuing the things that are important to me? So, you know, one of my favorite techniques here is this concept they call the dream behind the complaint. because you're right that like we tend to not be that great always I really dreaming and envisioning and saying this is my dream of what I want out of life right that can sound really scary for people but they're very good at complaining right usually people are very good at saying oh my god there's this thing happening or it's so annoying or this is person that you know really bothers me so much why are they always like this And so the magic of that complaining is that every complaint implies a dream, right? It implies a better world where that complaint is resolved. And so, you know, often, that's the tool that I'll take people to first to say, all right, great. Like, what's complain, right? So you'll so fun and good and releasing to complain and let's look at what that sort of implied world is, you know, behind that complaint, right? What is this vision? And then to really check, right? Okay, let's imagine you get that. That's the world of the future that you get. How does that feel? Is that big enough? Or is it kind of mad, right? Or are we like, oh, Uh, you know, my, my dream is that, you know, I get to speak up a little more in meetings. It's like, well, that's probably, that's probably not 100% of your dream. Like, which really behind that? And so I think it can, it can, that check can help you sort of level up to say, is this really an inspiring dream for me that's going to motivate me more than those fears that might be hiding in the background? And on the flip side, with entitled people, you can also get really unrealistic dreams. Where I make 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 serve to say, I don't know if that's quite by the train, right? And so if your dream is so embarrassing to say aloud, you can't even really own it. Maybe that's not the right dream. And so that that checking whether it actually feels inspiring, but also sort of credible and possible is a good way to sort of find that middle ground where like, yeah, this dream is hard. I don't know if I'm going to get it, but damn, it's worth trying, right? Like, I want to go full.

for, you know, specifically for articulating what you want, because that's kind of the first step of the, you know, asking for what you want process. It really is as simple as that, right? Let's start with, you know, sort of what you have consciously in terms of what you want and, you know, if you have trouble, then we can try looking at complaints and sort of starting to articulate a vision out of that. To me, really, what's interesting about asking for what you want is that on the surface, it's very simple. 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 warning from the response and what it tells us, because the response is usually no. And so really, what tends to be hard there, I mean, it's a straightforward process. It's not rocket science. What's hard there is the resistance, right? The parts of us that are not so excited about that, the things asking for what we want to scary in articulating a big dream that we might not get is really scary. Because what if I don't get it? What does that mean about me and my failure, right? Or, you know, what does it mean if I respect the know? 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 anyone. Because otherwise, it's, yeah, articulate, ask except.

So I have a more expansive definition of no than than most people I think because for me, it's it's not a yes unless it's a hell yes. Right? Because you really want enthusiastic consent, right? Not just a, maybe kind of, I'll try, you know, we'll see, but a, yeah, absolutely. Let's do this, right? And, and I think that often it's so tempting to settle for something less than that, to say. Oh, wow. Okay. We'll give that a try. And that often comes to bite us later on because we've set this thing that's short of a hell yes. And then we realize later on, oh, yeah, they weren't really in, right? They didn't show up to the party, right? Or like, they didn't deliver on time because my CTO said, Yeah, maybe we can deliver by, you know, May 1st, and then May 1st comes and surprise surprise, you know, your milestone is not done, right? Because you didn't, you didn't sort of go for that hell, yes. And so I think part of what I encourage people to do is want to really hear anything short of a hell, yes, as a no, right? And so it's not a bad thing, right? Mostly the world tells us no. It's actually really great data. It helps us figure out, what are we going to try next? What are we going to try next? Try next, try next, try next. because that's what's going to help us warn how to actually get to that hell yes. And part of that asking process is of not settling for it, but actually asking and saying, hey, you know, I'm hearing maybe your lukewarm on May 1st is a day. Like what would be a hell yes day for you? We could say absolutely we can deliver on that, right? And that way we're not making them wrong for saying no. We're saying no, of course you get to say no. Everybody gets to say no whenever they want. So let's get to a hell yes. What would it take for us to get?

Some people call this a whole body, yes. Because sometimes, like, your head is saying yes, but your heart is saying no, right? Or your gut is saying no. And so I think you can really feel in your body when you've got a hell, yes, right? When all of you is fully in and ready to do this.

It does, and it is something universal, but I do think of it as being particularly relevant to my work with startups, because you know, I work primarily with startup founders, because with startups, you know that mostly they fail, right? Like we all know the numbers on that. And so, to me, there's a sort of perspective you have to take if you're going to sort of operate in the startup world, being okay with not knowing that you're going to get the outcome anymore, right? You know, a lot of people we operate in a safer world where we're more clear exactly what the outcomes are going to be. But if you're a startup founder, you're going 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 forward 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'm no 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, right? Because I want it. And that's enough.

So the first step is articulating, right? And we've sort of gone into this a little bit. But to me, I think that the key places that people tend to sort of have missteps here are one in, one in this phrase, it's fine. I think of the, it's fine cartoon with the flames. You know, you know, the dog, I think it is, but I think a lot of us fall into that trap. Saying, you know what, I'm fine. I actually, I don't need, 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 it's like we're not guaranteed anything. So it's nice to be okay with the status quo. But for those folks, often what I'm encouraging to do is to really tune in to the parts of them that maybe aren't so fine. I'd really, you know, I prefer it a little bit if things were this way or yeah, I'm a little bit bothered by this or a little bit nervous about this and so kind of tuning more into those subtle emotions that are pointing them towards sure I'm okay with the status quo, but I kind of I want something more and so helping them articulate that in a clearer way where they can want something without being attached to having to get You know, the other extreme of this is people who, you know, articulate these sort of, you know, wildly unrealistic goals. So this is the founder that just wants everyone to agree with him all the time and to obey him immediately, right? And so for this, for those folks, it really tends to be more about saying it out loud. Because once you say it out loud, it is clearer. Yeah, that's not, 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 is that? 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 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

To me, a lot of the classic examples are around feedback. Right? Because, you know, I work with a lot of founders who, you know, are not the sort of classic control freak, right? They're super nice, right? And their teams love them, and they love their teams. And so, for them, it can be really hard to deliver, to deliver hard feedback, right? To deliver negative feedback, and even more to actually create consequences. Because the thing about accepting other people's nose is that, sure, they can always say, no, everybody gets to say, no, whenever they want. But there are consequences, right? And so the classic thing I see with the nice founders is they're really afraid to actually create consequences when people are not living up to their expectations, right? When they're not aligned with the culture, they're not sort of delivering in the way that the CEO wants them to be delivering. because it doesn't seem that nice. I think of myself as nice and of being so kind and 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 grown-ups enough that they can deal with the consequences of those choices.

of your differing opinion here and I totally validate you and I appreciate you and thank you so much for sharing that but they're not willing to go that extra step and say yeah but this is the call and I need you to sort of to actually fall through with that right and I understand that might be disappointing or frustrating or what have you but part of the expectation with this role is that you know you can roll with disagree and commit sometimes when that's necessary

It always comes back to integrity, right? And a great way to sort of do an integrity check is just look for how I fully express myself, right? And so I think we've talked a little bit about sort of charting your feelings as a piece of that, if like, yeah, am I really tuning into like how annoyed I am or how frustrated I am or how nervous I am, right? Because if I haven't fully 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? Gosh, is there something that I just 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, you know, sort of, you know, 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, right? First of saying, like, probably a lot of people will be grateful if we set out loud. I'm bored in this meeting. Let's move things around.

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, right? And so, if you're more in the people pleasing camp, maybe you're used to not asking at all. You're hoping that people are reading your mind and just magically knowing what you want, right? And if you're sort of more in the control-free camp, right, maybe you're used to ordering people around, is saying, go do this now. And so, you know, for both of those folks, right, it's not about, you know, I think if you ask any of them, right, like, is this working for you? Like they'd say no, right? Of course, it's obvious, like, from an effectiveness standpoint, it's not working well. But they more just haven't embraced that, yeah, you can do it a different way, right? But they only really see one way of doing it. And so part of asking for what you want effectively is really just recognizing the route 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 to have a story that says, this is too risky or, you know, or it's not worth it. They're going to say no anyway, right? So why even bother? And so, you know, these are all, you know, these are all sort of very common things that people go through, but then they end up not actually asking for what they want, and actually expressing who they are and what they stand for in the world. And that has a really serious cost, right? I think that, you know, we sort of tend to tell ourselves the story, oh, this is fine. I'll be fine versus owning, like, I'm going to be living my life, like not not asking for what I want. Like, do I really want to be at my funeral and have people say, oh, can I point it safe? You know, he didn't really go for his dreams, but he was nice. No one was ever mad at him. That's not what we want people to say is our ULGs.

Well, and so, but even implicit in that question, right? Like, there's, to me, to me, that's that question of, oh, how do I do it without there being any risk of ever pissing anyone off, right? That's a piece of the resistance, right there. And so this is a great example of the type of work that we have to do, right? Because, you know, in theory, that's getting easy. Oh, you just try some way and like maybe people are pissed off and maybe they're not, but like, 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 or particular way. And 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'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?

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 this. I want 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 gonna see things differently and that's fine. But it's important to me that you know that, right? And so what do you think? Like are you willing to reconsider this?

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 because especially in the PM world. We're trained to look for data, right? We're not just going to state an opinion. We're going to say, oh, the AB test said this, right? Or like 30% of our users do this or the ROI on this is X, right? And data is great, like we love data for a reason, of course. And I think people forget about exactly what you're highlighting that your relationships matter and that just your opinion, because you believe something, because you want something, often that's enough. Right? Because, guess what? You're in a relationship with these people you work with. Like, they care about you. Like, you have some sort of leverage with them. And I think that often, you know, often people go the other way and say, oh, I've got power. I'm going to try and leverage it. But actually, if you go the other direction in your humble and you say, I know I can't make you do anything. Right? It's not my call to make. But man, like, this is really what I want. I'm just going to put it out there and like, an 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 not fun at all.

And you know, I think there's a balance there as with anything like is ignoring data and going and gut all the time great. Probably not. 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. And I think often the danger is of people saying, oh, I don't have data to back this up. It's just what I think. And I'm not sure people are going to agree with me. So I'm just not going to say it. And so we don't have the data of all those gut opinions of these subject matter experts in the room, right? Even though that gut information to me is just as important as anything you get from, you know, the SQL database or whatever.

To me, complaints are great inspiration. And so, I think the, You know, to me, you know, like I will have radical candor, for example, right? You know, where where where I try to go a step further than radical candor is to not just say, hey, here's my feedback, you know, just want to do to know, but to say, and I want something, right? Like I would like to see an outcome, right? And so I think that to me it's all about the effective framing that 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 fall that thread down and think about how to be effective in that way, we can actually get something really compelling and useful. But it requires actually embracing that part of ourselves that sometimes we're a little bit ashamed of. 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 is important.

Well, I'm a big fan of the internal family system, which is the sort of psychotherapy technique that really talks about parts and the sort of parts of ourselves and the ways in which they don't always agree with each other. And part of why I love this approach is A because we already use this language, right? We say, part of me thinks this, a part of me thinks that. And really when I talk about how to work through resistance, really it's about embracing and validating all of our parks. Because often we're really comfortable with one part of ourselves that we think is, oh, this part is virtuous and good and great. And this part is whiny and bad and not great. And I don't respect that part of me as much. And so really to sort of ask effectively, we generally need to embrace all these parts and really bring in all the information they're bringing in. Because if we ignore the part that's really scared to ask, well, yeah, then we're going to stay stuck versus if we come in and say, hey, buddy, why are you scared? Like you seem terrifying. What's going on? Oh, well, man, like you think your whole professional reputation is staked on this and you're an imposter and they're going to find out and then you'll never work again. Well, of course, you'd be scared. That makes a ton of sense. And by embracing that instead of ignoring that and being ashamed of that, that does 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.

I took one of Stanford's Tea Group weekends, a number 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 mentioned. It was crazy. I mean, it was really wild.

I do. I teach the same thing, and yeah, I think, you know, sort of Carroll's approach and non-violent communication or DBT teaches a similar approach they call dear man to me with DBT. It's a dialectical behavior or 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 kind of 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 and maybe we can trust our eyes right like we know what would a video camera record it right and that's about it And so I think often we get really distracted by all these stories we have about the date of it. 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 the stories like you have mentioned of, you know, I feel like you're an asshole, right? It's like, well, that's a story, that's not a fact.

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

Oh, yeah, they're all tricky for sure. The most tricky, okay. But step three is accept the response. And it might seem so simple, right? But it actually is kind of subtle. And so, you know, one reason is that idea of, you know, sort of the whole body, yes, or the hell, yes, right? Because I think often we rarely want it, 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 know, but not over accepting or under accepting. 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, 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, that's over except, 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-free mode, I think for them, they at the often sort of kind of skip over their response. They say, wow, 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 we really respect people's nose, right? And actually, it can actually be more influential, more motivating, right? If someone says, okay, no, I'm not gonna, I'm not ready to deliver this on time. Be like, okay, well, I'm gonna give the project to another person. Right? Like, I'm taking your know-it-face value and they say, oh, gosh. Well, I didn't realize that was going to be the consequence. Maybe I can get it done by that time. Right? And so that way, you're not forcing them. You're not co-versing them, right? You're just saying, no, you said no, so that you're no one. I accept that.

Acceptance of the response is primarily an emotional regulation issue, right? Because once we get our emotions intact, it's just, is it yes or is it no, right? And if it's no, which it probably is, 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 for to tell me what to try next. And so, really, 99% of the challenge tends to be all the feelings that come off for us when we hear it now, right? Because we hate hearing no. It's so uncomfortable. And so, part of the practice of getting good at asking for what you want is recognizing, you're going to hear no all the time and that's completely normal and fine. And it doesn't need to be something so scary or awful.

I gave a talk about this, you know, sort of right after it happened, but I was fired from Slack three different times, which I feel like has to be some kind of startup record. I don't know, you know, who would be the record-keeping body for this? But, you know, now 10 years on, you know, I have different perspective of course. And so this was, you know, almost exactly 10 years ago, spring of 2014, you know, and I just got in the job as the first PM at Slack, and it was already the hottest thing out there. It was only a couple dozen employees. And I came in excited, but also a little insecure because I just come off kind of my breakup with my co-founder. I just wanted to kind of put my heads down, you know, put my head down and do a good job. I was engaged at the time, so Slack already knew. You know, I was going to be going away in a bachelor or backpacking trip, you know, I'm letting in hunting moon in the fall. And so I kind of came in kind of not even overconfident. If like, I've been a founder, I've worked on iconic products, I know how to do this, I'm a pro, I'm just going to go in and do the work. And so instead of getting really clear on what does success look like here, or what's your culture, or like, you know, what are your expectations of me? I kind of just went in and made my best guess and went for it. And low and behold, turns out like what I came in with that supreme overconfident was not what they wanted at all. They, you know, they'd kind of been in the trenches like reinventing from the game, you know, to to slack, you know, they've been through layoffs really hard times together. So they wanted someone to come in humble and to kind of earn their trust of this kind of core team that had been together for years. And so, I, you know, I just didn't get any of that, right? Like I wasn't, I wasn't sort of hearing that feedback. I wasn't hearing those nose. And I wasn't articulating what I wanted. What I wanted was really very basic. I just wanted to do figure out how to do a good job. And I wanted to have a good relationship with the CEO, right? Because, you know, I was working for him. I mean, you need to have a good relationship with your boss. But the problem was, you know, this sort of, in the first firing anyway was I had not, I had not articulated those goals. And so I shouldn't have been surprised when six weeks into, you know, my tenure at Slack, I came back from my backpack and tripped with my bachelor buddies. And I had an email in my inbox saying, hey, you're fired, right? Like, you know, it seems like it's not working out. Let me know how you want to wrap it up. So as you can imagine, I freaked out, right? I loved this job. I loved this company, so I profusely apologized. I said, you know, I'll do whatever it takes. I'm so sorry, you know, I'm, I'm gonna be committed to turn this around. And so early stage startup turns out firing doesn't always stick. Monday morning, I had my job back. But obviously, things were not the same as they'd been before. Because in the second era, that, but I wanted was sort of better articulated more clear. But all of a sudden, that fear that had been out of the surface, that insecurity was now very, very present every day. Because I was terrified, right? Of like, you know, wasn't going to get fired, right? Was I going to not, you know, make the most of this opportunity? And so, you know, I went fully into people, please, or vote. And so that meant that even though, you know, what I desperately wanted was to have this good relationship was to sort of, you know, be successful, build a great product. I had a year of one-on-ones with CEO. I never, never, ever asked for what I wanted. I never said it out loud, right? Because I was scared. You know, I was scared of what the consequences were. I knew there were 100 PMs, you know, standing behind me, ready to take my job if the CEO is ever, you know, a moment unhappy with me. I said, no, I'm not going to take the risk, right? I'm too scared of what the consequences might be. And so I held all that fear and all those desires, but I just wanted to do a great job. I wanted to be awesome partners and build this amazing industry-changing product. And I never said any of that stuff out loud. I just put my head down and I tried to obey. And so, you know, as you can imagine, right, this didn't work very well, right? Like, I was feeling horrible day-to-day. I was terrified of this guy I was working for. And so, again, I shouldn't have been surprised, but I was when I got fired for the second time, wasn't quite firing, but this time I'd come back from my honeymoon, and I had a phone call on Monday that said, you know, seems like product management's not working out for Slack. You know, we're actually just going to get rid of product. You're going to be user research is going to be fine. And for me, I love you as a research, but that was the beginning of my career. I was not interested in going back to that. And what was fascinating was at that point, I was actually able to articulate what I wanted there and was willing to say it out loud. Because what I wanted was, no, like, what's keeping me in product, right? I've got an idea for how we can run it. So I wrote a proposal. I sent it around to the management team. Turns out, when you actually ask for what you want out loud, you're 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. Right? Everything was fine. Except, of course, it wasn't fine. Because now I was scared, but the stakes seemed really high. Right? And this is where kind of that deep imposter syndrome said in. I was like, am I even any good at this? Like, should I even be in product management? Am I ever going to work in this industry again? Is this going to be my dark secret that I take to the grave that Stuart Butterfield fired me three times, you know? And so you know that what what I think what what I couldn't be with in that moment was was the nose right because I was getting no after no after no after no you know from from Stewart in the rest of the management team saying yeah like what you're doing is not working for us right like your ass or not landing like you're not being effective in the way that you want to be effective and because I wasn't able to hear those nose again because to that emotional regulation standpoint I just I couldn't handle the feelings of like oh like maybe what I'm doing is not good enough So instead of pointing the finger 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 which right. I can't, oh, evidence to the contrary, by the way, is this like product, luminary, visionary, famous person, right? So, you know, 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 work. And so again, because, you know, I was not articulate or what I wanted. I was not asking for it. And I certainly was not listening to the nose. You know, I shouldn't have been surprised when finally the third time it came down. And this time it was serious because we had a chart. So it turns out once you hire HR, the flowerings are final. And so I only made it to a year at Slack, and it was a year of just utter torture, because I spent that year being fully out of integrity with myself, right? Never saying what I really wanted, how I really felt, because it didn't feel safe. I was too scared. I kept it all inside. And it took me six months or a year, even after that, to really feel safe and okay again, right? It was a serious decompression time. My wife and I had a baby during that time, you know, I was on zero sleep. It was a rough rough period. But, you know, the irony is is that, like, when I actually came out of that experience, like the reality of it was extremely simple, right? I had an articulated road I wanted. I had an ask for what I wanted. I had not listened to the nose that in response to my non-ask, right? And so, of course, I was unhappy with yourself, 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, right? Even when we don't know exactly what the outcome's gonna be. And so that's really the story of how I became a coach, right? Of seeing exactly how much I've screwed up at Slack and seeing how much I've suffered and how much a lot of people suffer in these similar circumstances. And all you have to do to turn it around is ask for what you want. So this is why I'm so passionate about this stuff because it sounds so, it can sound so fluffy to say, oh, you know, focus on integrity, you know, honor your desires. No, like it's real life stuff of like a year of suffering, a pain of fear, right? Like, I don't want, I don't want other people to be going through that. And that's why I'm so passionate about this stuff.

Totally. One, and to me, the first one is about articulation as well, because I think that if in the beginning at articulated that, yeah, I'm confident, but I actually, I want to do a really good job, right? And I want to have good relationships. So let me, let me think about intentionally, how do I create those outcomes? But because I hadn't articulated, that's what I wanted. It didn't even occur to me. Oh, yeah, I need to do some intentional relationship building, figure out some metrics for success. Because in an early stage startup, there wasn't a ton of sort of process or structure in place. So if I used 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.

Well, I mean, obviously, broadly, I would have asked for what I wanted, right? And what I wanted was I wanted to do the best work of our life, right? I wanted to have a deep professional partner in the CEO and the rest of the product and management team. And yeah, I wanted to produce great work that people love, right? And that was part of why I was attracted to the culture and the mission and the company. And so this is what's tricky, right? Is of course, that's what I would have done. Now, do I know what the outcome would have been? No. I might have been fired even sooner, right? Like they might have said, no, you know, like this is not working out, like let's just, let's just be done here. And so that's what's tricky about this. Is it really isn't about the outcome, right? Of course asking for what you want makes you moral 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 and 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 like, yeah, I'm disappointed. I wish it had worked out, but it did.

To me, it really is about the relationship with the CEO or with the founders because that sort of the root of a lot of the issues that come out of that scenario. Because it's not always you, like in my story, I think it was primarily about me. But I also work with a lot of founders who are going through a really tough thing. My clue to people who report to a founder is to say, imagine if you're confused about how your founder is behaving, imagine that they're terrified all the time, right? And see if that makes their behavior more clear. Because it is scary to be a founder, right? Everything's on your shoulders. I think a lot of people do feel that sense of high stakes all the time. And so, you know, I think being real about that, I've like, what is the state that the person or the people you're working for are in and sort of working within that versus sort of pretending that it's something else or wishing that it were something else is sort of the path to having a healthy relationship. Because if you don't have a healthy relationship with the person you're working for, you're not going to get anything done. You're not going to succeed in any meaningful way.

I think it's a hard thing to generalize about, but to me it really is about understanding expectations. What do you, I guess this is a predictable coming for 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 sort of human subtleties and things they're good at or not so good at. And so being very, very clear about expectations and figuring out collaboratively a way to work together that's effective. To me is, you know, there's no guarantees, of course, but it gives you a sort of more sure path to having a productive relationship. And it's actually something that I recommend to a lot of founders for, you know, maybe their first, you know, 10 or 15 or 20 employees of just have like a relationship design conversation with each of them when they're first hired. because I think a lot of us come in naive the way I did assuming, oh yeah, I'm just going to come in and kind of do my thing. The way I've always done it is going to be fine versus coming in and saying, I actually don't know how I'm going to operate at this company, right? I have range like anyone has range and I don't know what this company needs and who else is here and sort of what 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 yeah, what is the best way to work together, given who we have now and what we want, what we need?

I do want to mention something that I hear a lot from founders when I talk about the piece of working through resistance. because I think a lot of them say, oh, you know, you want me to let go of fear and focus on what I want? Well, I mean, I've been running from fear in my whole career. Like, that's how I'm so hard working. And how I'm so smart is I'm always afraid I'm not good enough. Like, is, you know, am I going to be able to do this job without fear, pounding me every step of the way? And I just, and I just remember the first time I heard this, it broke my heart. And now I've heard it. you know dozens of times I'd say so I mean it really is I think it's a belief that sits deep in the hearts of a lot of us high achieving silicon valley tech types of you know my fear of not being good enough is what drives me to be great and I just want to come out here and say there's other ways to motivate right you can motivate based on joy based on vision based on you know your you know inspiration in this vision of what you want And 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.

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

For me, I'm not a big believer in discipline. You know, that I think, you know, some folks come to coaching looking for, you know, sort of a drill sergeant and say, all right, shout at me and tell me to do better. And I said, yeah, no, that's not, that's not how I operate because it's not the discipline doesn't work, right? But it's like people pleasing. It's a short term, it's a short term coping strategy. Like discipline will get you in the gym for a week. But it's not going to get you in the gym for a year, right? The people who are in the gym for a year are doing it because they want to, right? There's actually something that's motivating for them in that. That's not just, oh, I hate this, but I'm going to go anyway. And so, you know, I try to be really clear with people about that that I'm not going to be the drill sergeant because it's unsustainable. 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 for 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 am a broken record, admittedly.

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 and LinkedIn.

Well, I already mentioned radical candor. I think that is for sure a modern classic. And I think that that whole idea of sort of challenging directly, but caring personally is very much aligned with what I'm talking about, right? Because, you know, you need the relationships and you need to actually speak your true. So I love, you know, Kim Scott's writing on that stuff.

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

I also love the 15 commitments of conscious leadership. So I pretty sure other guests have mentioned that as well. But to me, part of why I like that is that I think a lot of personal development books are not very directive. They say, oh, you know, just dig deeply and find your truth. And while there is value to that, of course, I think sometimes it's nice to have some direction. If yeah, here's 15 things that like generally your life's going to be better if you do that. 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.

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

I also love, I mean, actually, you know, speaking of that. I mean, it's almost two on the nose, but there is this movie living from a couple of years ago that this British actor who is this sort of, you know, he is this sort of, you know, tough, old sort of, you know, staggy 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 month of my life? And he builds this playground for children. And that's actually his legacy. Sorry, actually spoiler alert. Whoops.

uh... well you know it's it's funny i i used to be a big wine fishing auto and i think as as with many of us i am discovering i feel better with less alcohol in my life and so one of the things i've been picking up is uh... whoong tea i've got a little cup of Taiwanese when shung bau jong in front of me and um... i feel like it's like all the nursery that i put into wine of like regions and veritals 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. So yeah, I've been totally going down a nerdy tea rabbit hole, and I recommend it. Taiwanese Mountain Teas, especially.

There's lots of, there's lots of great stores online. You can check out T from tywan.com. That's a good one.

So this is actually part of why I started writing this book is because my friends were probably annoyed with me, you know, telling them, have you asked for what you wanted, right? Ask for what you want. Because yeah, it's the best advice I have.

Ooh, all right. Well, you know, I think for me, you know, when are you, you are already an industry-womenary with, you know, thousands of followers. I am interested in sort of sharing more of these ideas. So if you 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. I just am so passionate about it and yeah, I'd love if you'd come and join me in that journey bring questions and ideas and I'd love to talk about this stuff because I I just find it endlessly interesting, but you're working on a book along these lines at some point that will come out right that That's right, that's right. So yes, so I'm working on it in book form, but part of what I've been doing is I realize I want to work on it in community, right? Speaking of asking role 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 about making a difference for my clients. And so I realize, yeah, if I really want to make a difference with people, I need to psychoproduct. I need to get out in the world and test out these ideas and see what lands with people and what's effective for them and what works. hear the stories and sort of really get into it. So that's kind of why I've been putting myself more out there.

So you can find me on LinkedIn. I'm Kenneth Berger, BERG ER. So please follow me there. Subscribe to the ask for what you want newsletter. And yeah, you can check out my website, kberger.com, KBERG ER.