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

Transcript from https://podmenti.com/t/db3ed990ced64af1

You were famously the first PM at Slack, and then you ended up transitioning into executive coaching. For me, the impact was about making this work sustainable. So that we're not burning out or selling out, but actually able to pursue these hard goals that we have in startups. What we're gonna be talking about today is
Your personal magnum opus, the output of ten plus years as a founder and operator, and seven plus years as a coach. The core idea is ask for what you want. Turns out when you actually ask for what you want out loud, you're much more likely to get it.
You're hired.
Sh
How do you know that this is something you need to be working on? If you're more in the people pleasing camp, maybe you're used to not asking at all. You're hoping that people are reading your mind. And if you're sort of more in the control 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 dream. Let me envision a better future. Let me think
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.

Today my guest is Kenneth Berger.
Kenneth coaches startup leaders to help them avoid burnout and live the life that they want.
He was the first product manager at Slack.
And spent over 10 years in tech before transitioning into coaching. His core focus with leaders is to help them learn how to ask for what they want.
This sounds really simple.
But as you'll hear in our chat.
This one skill is at the core of so many of the struggles that people have in their career and in their life.
Kenneth shares a ton of very tactical advice to help you figure out what it is you want.
How to overcome the resistance that comes with asking for what you want, how to actually ask for what you want effectively, why the most important step is hearing the response that you get.
When you ask for what you want.
And all of the things that will change in your life if you get better at this one skill.
Kenneth also shares the story of him being fired three times from Slack, which is hilarious. With that, I bring you Kenneth Berger, after a short word from our sponsors, and if you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. It's the best way to avoid missing future episodes, and it helps the podcast tremendously.
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Come.

Kenneth, thank you so much for being here. Welcome to the podcast.
Hey, thanks for having me.
I love that.
We should that should be a tradition that everyone goes with.
I love that.
So we originally met
when w I was doing a post on being a first product manager
at a company you were famously
The first PM it's Slack.
And then you ended up
transitioning into executive coaching, which is what you do now.

Something that you describe to me as quote
Your personal magnum opus, the output of ten plus years
As a founder and operator and seven plus years as a coach to startup leaders.
And the core idea is
Simply asking
For what you want.
Which sounds really simple.
So let me just start broadly.
Just w why have you found that this
Skill.
so core to so many of the challenges that people run into in work and in life.
You know, if I had to answer in one word, it would be integrity.
Right, and
I think that
It's one of these funny things where, you know, everyone thinks they already know how to ask for what they want. Like we all ask for what we want. We order our coffee in the morning.
And we all think we have integrity. No one walks around thinking I'm lying to myself all the time.
Or wind other, certainly. And yet
We tend to kind of fool ourselves a little bit, right?
You know, when it comes to are we really pursuing the things that we want in life?
Right.
And I think
To me, the flip side of that.
is is sort of the reason that the stakes around asking for what you want are so high.
Because
Yeah, you know, if you're we can't guarantee we're gonna get what we want.
But if we're asking for it regularly, if we're listening to the response, we're respecting the no's we get from the world.
Then we can kinda 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 whatever.
And if we don't do that.
Well then
We're kinda fooling ourselves that we're actually moving towards what we want. There tends to be all these
sort of unexpected secondary and tertiary effects that come out of that.
Right.
Uh
stress and frustration and unhappiness, because of course asking for what we want, pursuing
What's important to us in life is
Just one of the most important things of fulfillment, right? Of
of what's what's you know important in sort of achieving our purpose.
What are it just some
Challenges that
people have in their life and career that are just rooted in this
Doing this badly, not asking for what you want, not knowing what you want.
For me with clients, I think what I'm often looking for are
It's 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
In her coaching sessions.
Right.
Probably you're trying the same thing and not getting any different results, right? It's sort of that definition of insanity thing.
And so
really I look at that and say, Okay, you know, maybe you're asking for all you want.
Right, maybe. Although often people aren't.
But even if you are, you're probably not achieving it, right? You're not getting the results that you want. So why are we not learning from that? Why are we not
Sort of
uh moving forward, getting new data, trying something new, actually treating it as a sort of iterative development discovery process.
So I think that stuckness is one thing and I think the other thing I hold for is interpersonal.
Right, because
I think that
You know, one one mode of not asking for what you want well is kind of holding back.
And not really saying it out loud.
And I think another really common mode
is coming with a lot of entitlement of like, you know what, you better do what I say. I'm your boss, you're my report.
You you better you better obey or agree or whatever it is.
And of course the danger of that is interpersonal conflict. Even if you are their boss, right? That's a really disrespectful way.
To come into the conversation.
And
Yeah.
It's it's uh obvious source for a lot of issues.
Before we get into how to
learn to do this better and
More of why this is so important.
Is there an example from your career where you did this really badly or you
Didn't ask what you want. There's so many examples.
You know, I I think, you know, we'll we'll we'll eventually get into the the story of how it was fired from Slack, but um
I think
For me, you know, the the thing that always came up was just being attached to being right. And I think a lot of us
sort of get into this boat. 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've you know learned all this stuff the hard way, believe me.
is it's fundamentally disrespectful to go into a meeting
already deciding that you're right and the other person is wrong.
Right, because you can't know that for sure.
Right.
There's always a new perspective, new data that could come in.
And so you want that conversation to really be a back and forth.
And if you're coming in with this really ingrained sense of righteousness, you can't do that. There's no there's no way to have that conversation respectfully.
Think you may have already answered this question, but I think it's really important is how do you know that this is something you need to be working on?
How do you know like I really need to pay attention to what Kenneth's about to tell me? You said one is
you feel you're stuck in your career, something you're just not making progress.
And this could be the answer.
Or you said
There's interpersonal conflict and you're just having a lot of conflict people.
I think those are great things to look for. I think it's also good to look for
Kind of a sense of things being high stakes.
Right. Because I think part of what can
create a lot of sort of conflict and difficulty in these situations is a sense of this is life or death.
Right. And that was certainly how it was when I was a founder.
Right of
Okay, normally, you know, when I was at Adobe, it's a big company, you know, they're gonna be fine either way, no matter what I do, right? I can be easy going, you know, let someone else have their way in the meeting.
But when it was my company
Right? When it was my vision on the line.
I didn't feel especially flexible.
Right. The stake seemed really, really high, right? This is the success of
My idea, 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 if we're running away from our fears, it doesn't necessarily mean we're getting anywhere meaningful for for what our desires are.
And so
That
that sense of high stakes that often we can get, whether it's in interpersonal conflict or being afraid of asking for what we want.
That can get us really focused on the fears rather than focused on

There's a question I was gonna say for later, but it's something that's very top of mind for me.
Is
Knowing
what you want. Like how do you know what you want?
There's basically knowing what you want and then asking for what you want. And I often
I'm like I try to I'm like I I like equanimity in my life and so I often
Don't
ask for what I want or kind of push down maybe what I want, or I don't think about what I want. I just want other people to be happy.
And I'm curious what
people can do and what I can do.
to get better at knowing here's what I actually want, here's what would make me happy.
And fulfilled.
What are some skills there?
I could work on and other people can work on. Well, first of all, I'd say you're you're very far from alone there, right? I mean, I think the people pleaser coping strategy is one of the sort of
Most classic.
And and it is effective, right, in the short term, right? Like oh, you can feel safe and calm when other people are generally happy with you.
And the cause tends to be long term.
Right.
In terms of
Am I really pursuing the things that are important?
So
You know, one of my favorite techniques here is is this concept they call the the dream behind the complaint.
Because
Yeah, you're right. That like we tend to not be that great always at really dreaming and envisioning and saying, This is my dream of what I want out of life, right? That can sound really scary for people.
But we're very good at complaining.
Right. Usually
People are very good at saying, Oh my God, there's this thing happening at work. It's so annoying or there's this person that
You know, really bothers me so much. Why are they always like this?
And so the magic of that complaining is that
Every complaint implies a dream.
Right, it implies a better world.
Where that complaint is resolved.
And so
You know, often that's the tool that I'll take people to first to say, All right, great, like let's complain, right? Feels so fun and good and
Releasing to complain.
And let's look at what that
sort of implied world is you know behind that comp
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 kinda meh, right? Are you are we like, oh
Uh
You know, I 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 a hundred percent of your dream. Like, what's really behind that?
And so I think it can
it can that check can help you sort of level up to say, is this really
an inspiring dream for me that's gonna motivate me more than those fears that might be hiding in the background.
And on the flip side, with entitled people, you can also get
Really unrealistic dreams.
Where
I might say, Okay.
So it sounds like what I'm hearing is that your dream is that everyone obeys you and automatically agrees with you no matter what.
And they sort of say
I don't know if that's quite my dream, right?
And so
If your dream is so embarrassing to say out loud, you can't even really own it.
Maybe that's not the right
Dream and so that that checking whether it actually feels
Inspiring
But also sort of credible and possible.
is a good way to sort of find that middle ground where like, yeah, this dream is is hard. I don't know that I'm gonna get it.
But
Damn it's worth trying.
Right. Like I wanna go for it.
I love that.
For someone that wants to try this on their own and help themselves get better at
This
Without you being there.
What is it that you do? Is it you dream about what
would make you happiest. Is it like complain and see what's at the root of it? Is it
Just imagine a world where you're really happy and see what emerges.
For you know, specifically for articulating what you want,'cause that's kind of the first step of of the, you know, asking for what you want process.
It really is as simple as that, right? Of
Let's start with
you know, sort of what's what you have consciously in terms of what you want and you know, if you have trouble then
We can try looking at complaints and sort of starting to articulate a vision out of that.
But
To me, really what's interesting about asking for what you want is that on the surface, it's very simple, right? I mean, the steps I outline are.
Articulate what you want.
Ask for what you want intentionally.
And accept the response.
And then
Try again, right?'Cause it's an iterative process, right? 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 you know not rocket science.
What's hard there is the resistance.
Right, the parts of us that are not so excited.
The things
Asking for what we want is scary and articulating a big dream that we might not get.
Is is really scary. Because God, what if I don't get it? What does that mean about me? Am I a failure?
Right, or
You know, what does it mean if I respect the no? Like what if I ask for my big dream and someone tells me I'm not gonna get it?
Like what does that mean? How am I gonna feel?
And so
working through all that resistance is really a lot of what tends to be tricky about asking for
Yeah.
Articulate, ask, accept.
Okay. Uh you're you're getting into where we're gonna go.
Before we get there, final question, this idea of
Dealing with no.
I think this is the other big
Locker for people is like oh it's so scary to ask.
For like something I really want.
Or
Or ask for something big.
That is really important to you.
What is it that
Are you advise there of just kinda getting over that
This fear of just like asking for what you want. So I I I have a more expansive definition of no th 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 uh
Maybe kinda, I'll try.
You know, we'll see.
But uh
Yeah, absolutely. Let's do this.
Right.
And
And I think that
Often it's so tempting to settle for something less than that.
To say
Oh well, okay, we'll give that a try.
And that often comes to to bite us later on.
Because we accept this thing that's short of a hell yes.
And
Then we realized later on, oh yeah, they weren't really in, right? They didn't show up to the party, right?
Or like
They didn't deliver on time because my CTO said
Yeah, maybe I think maybe we can deliver by by you know May first.
And then May first comes and surprise, surprise, you know.
Your milestone is not done.
Right, because you didn't
You didn't sort of go for that that hell, yes. And so
I think part of what I encourage people to do
is one to really hear anything short of a hell yes as a no, right? And so it's not a bad thing, right? Mostly the world tells us no.
It's actually really great data. It helps us figure out what are we gonna try next? What are we gonna try next, try next, try next.
'Cause that's what's gonna help us learn how to actually get.
Hell yes.
And part of
That asking process
is of not settling for it, but actually asking and saying
Hey, you know, I'm hearing maybe you're lukewarm on May first is a date.
Like
What would what would be a hell yes day for you where you could say, absolutely we can deliver on
Right.
And that way we're not making them wrong for saying no. We're saying no, of course, you get to say no. Everybody gets to say no whenever they want.
Um
So but let's get to a hell yes. What would it take for us to get there?
That's a really helpful framework and and phrase to use is just what would it take to get to hell, yes.
Not just what would it get.
take to get to you feeling comfortable with this.
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.
Yeah, oftentimes people kind of like, Yeah, yeah, yeah, yeah, and then they don't actually follow through.
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 and ready to do this.
And this applies to you're giving examples here of just like getting h like a line and deadline.
I imagine the same skill applies to every
Than you in light.
Like relationship questions and
Friends and family and work.
It does. And I and you know, it is something universal, but I I do think of it as being particularly relevant to my work with startups,'cause you know, I work primarily with startup founders.
Because
With startups, you know
But mostly they fail.
Right.
Right, like we all know the numbers on that.
And so
To me, there's a sort of perspective you have to take if you're gonna sort of operate in the startup world.
Of being okay with not knowing that you're gonna get the outcome.
Right.
You know, a lot of people we operate in a safer world where we're more clear exactly what the outcomes are gonna be.
But if you're a startup founder, you've got to be okay with, I'm just gonna go for this and I know I probably won't get it.
But it's so meaningful to me, I'm gonna go for it anyway.
And so to me
That's not just about
the big picture of running a startup. It's about really anything you might want in life because that's such a useful perspective to say.
I know I'm not gonna get it. I know I'm not guaranteed to get it. I'm not gonna be attached to that. I know people aren't
Obligated to tell me yes.
But
I'm gonna go for it anyway.
Right.
Because I want it and that's enough.
So let's actually get into the skill of learning how to actually see.
Ask for what you want more effectively.
You already
describe three steps. So maybe just describe them again and let's just walk through them.
So
The first step is articulating what you want.
Ryan, we've sort of gone into this a little bit, but
To me I think the the key places that people tend to sort of uh
I've missed steps here or
One in
One in this phrase it's fine. I think of the it's fine cartoon with the flames.
You know.
Um the the dog, I think it is. But I think a lot of us fall into that trap saying, You know what, I
I'm fine. I I actually I don't need
I don't need anything, I'm good.
And again
This is tempting, right?'Cause it's so nice to have this
idea that I'm fine, I don't need anything.
And in a certain way that's a nice attitude because yeah, like we're not guaranteed anything, so it's nice to be okay with the status quo.
But
For those folks, often what I'm encouraging to do is to really tune into the parts of them that maybe aren't so fine. Like, gosh, I
I'd really, you know, I'd I'd prefer it a little bit if things were this way. Or yeah, I'm a little bit bothered by this, or I'm a little bit nervous about this. And so
kind of tuning more into
Those subtle emotions that are pointing them towards, sure, I'm okay with the status.
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.
uh uh articulate these sort of you know wildly unrealistical. So this is the founder that just wants
Everyone to agree with him all the time and to obey him.
Immediately.
Right. And so for this for those folks, it really tends to be more about saying it out loud. Cause once you say it out loud.
It is clearer. Yeah, that's not
Like I'm not
That's not really what it's about.
And so for those folks, I tend to ask them to go deeper to say
Yeah, I know you're not a control freak, right? You don't want, you know, everyone to think exactly what you think. What's it really about?
What does that get?
And so
Often it goes from being this kind of
More
kind of objective external goal to being a more kind of social emotional goal of
You know what? I just want to have a team that feels really aligned around me and like we're just ready to go for it and we've
Got each other's backs.
And that doesn't mean we agree with each other all the time or that we're a hundred per sp
hundred percent aligned and everything.
But it does mean there's a certain feeling that I have when I go into work.
Even though I don't know that we're gonna get what we want.
Or that everyone's going.
Do you have any examples?
From your time you could share if someone
articulating what they want and figuring out how they articulate
How to articulate what they want just to make it even more real.
To me a lot of the classic examples are around feedback.
Right.
Yeah.
I I I work with a lot of founders who, you know, are not the sort of classic control freaks, right? They're super nice, right? And their teams love them and they love their teams.
And so
For them it can be really hard to deliver
to deliver hard feedback, right? To 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, you know, aligned with the culture or they're not sort of delivering in the way that
you know, the the the CEO wants them to be delivering.
Because it doesn't seem that nice. Like, Oh, I think of myself as nice and and of and of being so kind and of people loving me and
It's like well
that that doesn't mean that there aren't consequences for their actions, right? Part of
really respecting them is respecting that
They can make the choices they want and they're grown ups enough that they can deal with the consequences.
Those choices.
Can you even get more concrete there? Is it like we need to hit this date or
There's gonna be big problems.
Or is it like I need you to
hire the slar of a team. I don't know, like what
What is it that they they're not articulating that they later realize, Oh, here's what I need to articulate?
So I think sometimes it is about alignment, right? The disagree and commit.
So I see that a lot, right? Of like
You know, founder saying, Hey
You know, I'm super respectful of, you know.
of your differing opinion here. And I totally validate you and I appreciate you. And thank you so much for sharing that.
But they're not willing to go that extra step and say
Yeah, but this is the call and I need you to sort of
to to actually follow through with that.
Right.
And I understand that might be disappointing or frustrating or what have you, but
Part of the expectation of this role is that
You know, you can roll with disagree and commit sometimes when that's necessary.
That's an awesome example. I fully
get that and I could see how many people are not are uh how scary that is to a lot of people.
One is just like coming to terms with this is what I actually want to be doing, but I just don't feel like I can'cause it's gonna
I think upset people.
Yeah. Okay. So
What else can you suggest people do to help identify what it is they want and articulate
What they want. So you talked about pay attention to just like oh this would be better.
If like if this changed, I would be I'd h be happier.
Or things have probably run better.
That's a really
That's a really cool.
example of how to think do that,'cause that's easy. Just like, Oh yeah.
If we like
Actually can
Make a decision.
In this meeting, that'd be really cool.
Maybe I should try to do that and ask for that.
Uh is there any other tips and uh approaches to helping you figure out what you
It always comes back to integrity.
Right, and a great way to sort of do an integrity check.
It's just look for
How do I ful myself?
Right.
And so I think
We've talked a little bit about sort of
charting your feelings as a piece of that. Of like, yeah, how am I really tuning into
Like how annoyed I am, or how frustrated I am, or how nervous I am.
Right, because
If I haven't fully owned those feelings and expressed those in whatever way is appropriate, then
probably I'm not fully in integrity.
And I think saying what you have to say is a piece of that too, right?
Gosh, is there something that I just
I keep thinking about and I'm just like, you know.
three or four days I'm just like man
I really want to say this to this person.
Right. At this point you're probably out of integrity'cause there's something deep in you that really
needs to say this, right?
And so
It's to me, articulating what you want is really about mindfulness,'cause it'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 gonna get what I want or that people are gonna, you know, sort of you know, g give me all my dreams immediately.
But
It feels so much better to have it out.
Right.
That that sort of suffering
You know, that fear usually comes from holding it in and saying, Oh, having these stories of I'm not allowed to say that. It's not appropriate to express that
I'm bored in this meeting.
Right.
versus saying like probably a lot of people will be grateful if we said out loud, I'm bored in this meeting.
Let's m throw.
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Okay. This is a great segue too.
Okay, now I have a sense I need to
Change this. This needs to change. I'm just scared.
Two
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?
So for for asking what you want, I think
The really important tweak here is asking intentionally.
Right, because I think a lot of us are kind of stuck on a certain track that's comfortable for us when we ask.
Right. And so
If you're more in the people pleasing camp, maybe you're used to
Not asking at all. You're hoping that people are reading your mind.
And and and just magically knowing what you want.
Right.
And if you're sort of more in the control free camp.
Right. Maybe you're used to ordering people around and saying, Go do this now.
And so
You know, for both of those folks, right, it's not about
You know, I think if you ask any of them, right, like is this working for you?
Like they'd say no, right? Of course it's obvious like from an effectiveness standpoint it's not working well.
But they more just haven't embraced that
Yeah, you can do it a different way, right? That they only really see one way of doing it. So
part of asking for what you want effectively is really just recognizing
the rut that you get stuck in and sort of working through
all those narratives that make us resist asking in a different way.
Right, because
Often the people who don't want to ask have a story that says
This is too risky.
Or
You know, or it's not worth it. They're gonna say no anyway.
Right, so why even bother?
And so
You know, these are all you know, these are all sort of very common things that people go through.
But
then they end up not actually asking for what they want, not actually expressing who they are and what they stand for in the world.
And that has a really serious cost, right? I think that
You know, we we sort of tend to tell ourselves the story, Oh, this is fine, I'll be fine.
uh versus owning
Like I'm gonna I'm gonna be living my life like not
Not asking for what I want. Like, do I really want to be at my funeral and have people say, Oh, Kenneth played it safe? You know, he didn't really go for his dreams, but he was nice. No one was ever mad at him.
Right. Like that's that's not what we want people to say is our Euegis.
No.
That's uh
That's good motivation.
Okay, so say in this example you gave of like I just need
I need us to make a decision.
I know I'm trying to keep everyone happy, but we need to make a decision.
Div um
advice for maybe phrases of how to approach
You talked about making intentional.
How do you actually go about doing that? Is it like the way you communicate it? Is it
Something else. How do you actually
do this without pissing people off and also just like
Risking.
Too much.
Well and so so
But but even implicit in that question, right?
Like
There's
To to me to me that's that that question of oh, how do I do it without there being any risk of ever pissing anyone off?
Right.
That's a piece of the resistance right there. And so this is a great example.
of the type of work that we have to do.
Right, because
You know, in theory
Tasking is easy. Oh, you just try some way and like maybe people are pissed off and maybe they're not, but like
Probably is gonna be fine and you'll have the chance to try again and iterate and learn from it.
But often we get stuck, so we don't get to go through
those levels of iteration because
We want to make sure we're gonna get the outcome we want.
We say oh
Well, I'm not willing to ever piss anyone off.
Ever.
And so
I'm just gonna be stuck at this step.
Because
Like I haven't figured out what's gonna guarantee me. And of course there's no guarantee. We can never guarantee that people are gonna feel a particular way.
And so part of
Part of asking for what you want effectively is actually
Bringing some compassion for yourself.
Of course we all want.
To be sure.
That
the way we ask is gonna be effective and no one's gonna be mad at us and we're gonna get all of our dreams come true.
But yeah, no, we don't get that, right? Like I wish we did. That would be nice.
But
Is that worth?
Not pursuing your dreams in life.
Such a good point.
Uh about what you identified and how the way I
I think about in the way I think a lot of people I think about is just like
We should do this without
Causing anyone any.
Any pain or risking anything going wrong. I mean that's
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 I see on teams.
other functions that don't have, you know, power, quote unquote.
Is there anything that you suggest these folks do differently or think about this differently, or is it kind of the same thing in the end everyone has
Power in some way.
How do you
How do you would you think about this if you're just like say a product manager, individual contributor?
I think one of the most important balances in terms of the asking step is
Both
Asking clearly.
But asking with great humility. And this actually works whether you're in a position of power or not.
Because I think a lot of folks will go so far to the end of humility they say, Well, I'm not gonna go
I'm not gonna say this out loud at all.
But in fact, if you're willing to say, you know
Like I really disagree with this product decision and like I I would really prefer that we make this different decision.
And I know it's not my call and I'm just one opinion and a lot of people are gonna see things differently and that's fine.
But it's important to me that you know that.
Right.
And so what do you think? Like are you willing to reconsider this?
That's such a
Great.
approach. It's like very not scary to say that.
Yeah.
It also I think highlights something I wanted to touch on is
I think people have a lot more s influence and power.
than they think they do.
Say a PM on a team disagrees with a
A plan for a product.
Like
People actually care about
Your opinion.
And you could actually change things by just telling them I don't think I think this is a bad idea.
And you often don't.
Is that what you find that people have a lot more influence than they
Think they do. Anything along those lines that comes up.
You're actually you're giving me deep goosebumps because this is
I I I think this is this is a really underappreciated thing in terms of
asking for what you want because especially in the PM world
We're trained to look for data, right? We're not just gonna state an opinion. We're gonna say, Oh, the A B test said this, right? Or like
thirty percent of our users do this, or the ROI on this is X.
Right.
And data is great. Like we love data for a reason, of course.
And
I think people forget about exactly what you're highlighting that
Your relationships matter and that
Just your opinion because you believe something.
Uh because you want something.
Often that's enough.
Right. Because
Guess what? You're in a relationship with these people you work with. Like they care about you. Like you have
You have some
sort of leverage with them.
And I think that
Often
You know, often people go the other way and say, Oh, I've got power, I'm gonna try and leverage it. But actually if you go the other direction
And you're humble and you say, I know I can't make you do anything, right? It's not my call to make.
But man, like
This is really what I want. I'm just gonna put it out there and like and ask.
that I think it feels really vulnerable and uncomfortable to not
lean on data as a sort of way of saying, No, no, I'm right. So you should believe what I believe, but just say
Actually I don't know that I'm right.
This is just what I think.
And I hope that's enough on its own.
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 I shouldn't say anything'cause I don't ask for
Why I don't have a great answer. I just
I just think this is what it should be.
Totally. Well and and you know, I think
There's a balance there as with anything. Like is is ignoring data and going in gut all the time great.
Probably not, right? We we we use data for a reason.
Um
But
I think there are all these, you know.
sort of all these moments when we are making a gut decision, right? And
having all the data there means
having the opinion said out loud, and I think often
the dangers of of is of people saying, Oh, I don't have data to back this up. It's just what I think.
And I'm not sure people are gonna agree with me. So I'm just not gonna say it.
And so we don't have the data of all those gut opinions of these subject matter experts in the room.
Right.
Even though that gut information to me is just as important as anything we could get from, you know.
The SQL database or whatever.
Before we move on to step three, you already you talked about the kind of 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 gonna fail. I knew this was a terrible deadline, I knew this design was
Not great.
Anything more you wanna
say along those lines of just like
If you're not asking for what you want, you should
complaining is often a sign that you're you should be doing that more.
To me, complaints are great inspiration. Um, and so
I think the
You know.
To 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 wanted you to know.
But just say
And
I want something, right? Like I would like to see an outcome.
Right.
And
And so
I think that
To me it's all about the effective framing that
You know, the
The complaint is probably not gonna be an effective way to do it, but it can be great inspiration to say, gosh, that complaining means I'm frustrated.
What am I frustrated about? Let me envision that better future. Let me think about what's an effective way to actually move towards that.
What an effective way to communicate
you know, that desire, like that's actually likely to get me towards a yes.
And so
When we actually embrace
That sort of
You know.
frustration, annoying, complaining thing, and follow that thread down and think about how to be effective that way.
We can actually get something really compelling and useful.
But it requires actually
embracing that part of ourselves that sometimes we're a little bit ashamed of, right? Oh
I kinda like that whiny part of myself.
Like I'm just gonna push that one down.
versus actually taking
What it has to say is important.
That's a really good uh
Point. I think that's actually another blocker for a lot of people is just I don't want to be a complaining person.
Mm-hmm. I just wanna be like, let's do this, I'm in, let's go, let's uh I don't wanna
Be seen as a squeaky wheel. Is there anything you say there about
As a resistance.
Point for people.
Well, I I'm I'm a big fan of uh internal family systems, which is this sort of psychotherapy
Technique that
really talks about parts and and the sort of parts of ourselves and the ways in which they don't always agree with each other.
And part of why I love this approach is A, because we already use this language, right? We say
Part of me thinks this, a part of me thinks that.
And really when I talk about how to work through resistance.
Really it's about
embracing and validating all of our parts. Because often
we're really comfortable with one part of ourselves that we think is oh this part is virtuous and good.
And great.
And this part is whiny and bad and not great and I don't respect that part of me as much.
And so
really to
sort of ask effectively, we generally need to embrace all these parts and really bring in
all the information they're bringing in because if we ignore the part that's really scared to ask.
Well yeah, then we're gonna stay stuck.
versus if we come in and say
Hey buddy, like why are you scared?
Like you seem terrified. What's going on? Oh
Well, man, like you think your whole professional reputation is staked on this and
You're an imposter and and they're gonna find out and then you'll never work again.
Well, of course you'd be scared. That makes a ton of sense.
And by
embracing that instead of ignoring that and being ashamed of that.
That is often how we soften those fears and say, Yeah, like I know that's scary, but we also know that's not really true, right? Like you're not an imposter, right? You're
An experienced professional.
Man, there's so many threads we can't fully here this whole
Line of what it internal family systems, right? That's a
That's its own podcast episode potentially, and then imposter syndrome. We've touched a a bunch of different podcast episodes, but I'll
Avoid going in that direction.
Reminded me of is uh we just had Carol
Robin on the podcast who
taught this class to Chiefly at Stanford for a long time, which is all about helping people learn how to deal with other people, which we never learn in life. It's like a class
How to learn to work with other people.
I took one of Stanford's uh tea group weekends.
Summer of twenty twenty.
I think a month after George Floyd was murdered.
And was facilitated by a black woman.
And
It was one of the most profound
transformative weekends of my life.
I mean
'Cause it uh'cause T groups already people rave about them, but having it at that point
In history with those people in the room.
Oof.
A lot of tears, I imagine. It was it was it was crazy.
I mean.
It was really wild.
I feel like every single person that has gone through
I think it's called leaders in tech is the broader umbrella term.
And Carol talked about it. Everyone that was gone through it.
O hundred percent it told me that it's a transformative
life experience for them. And so and you had a you had a
Bonus transformational piece.
So anyway, if people want to check out that episode.
Uh I will link to it in the show notes.
But the reason I brought it up is
Carol shared this framework for how to actually give feedback.
In a way where people can receive it, that I'll just highlight here. I have it here.
And it's it's somewhat related to nonviolent communication, which is what you
touched on and she told me actually she
uh taught this way before nonviolent communication came out with
Their whole philosophy.
And it's basically
When you wanna give someone feedback.
The f the template is
When you do
A behavior.
I feel
A feeling and she's big on like say actual feeling word, not like I feel like or I feel that.
Blah blah blah.
And
Step three is I'm telling you this because
And then what you want them to change.
Do you uh do you find that
sort of approach.
Helpful.
I do. I I teach the same thing and yeah, I think you know sort of
Carol's approach and and nonviolent communication.
Uh DBT teaches a a similar approach, they call Deer Man.
Um
To me, it's T B T.
Uh it's a dialectical behavioral therapy. It's it's related to CBT.
Um
So there's there's kind of rough consensus, you know, in in the sort of personal development world of
How to
how to ask. And really what they have in common is around
Kind of staying really factual.
Because you know, I I think that
You know, what can we know factually? Well, we can know our thoughts, we can know our feelings,'cause no one else can know that better than us.
And
Maybe we can trust our eyes, right? Like, you know, what would a video camera have recorded?
Right, and that's about it.
And so I think often we get really distracted by all these stories.
We have about
the data, but when we bring it back to that fundamental core of
This is what I think, this is what I feel.
This is what I've observed in the world.
It tends to make the ask a lot clearer versus
these stories like you 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.
Yeah, that I feel that is not the right way to say I feel.
What do you actually feel?
Yeah.
Okay, so let's move to step three. I've been we've been going on this whole tangent of therapy and stuff, which is amazing. But
Let's make sure we cover all three steps. So step one again was
Articulate what you want.
Step two is ask for what you want. What's step three?
So to me, step three is actually the trickiest for most people. Um
And so far they're all tricky to me.
Oh yeah, they're all they're all tricky for sure. The most tricky, okay.
But step three is accept the response.
Mm-hmm.
And it might seem so simple, right?
But
It actually is kind of subtle, and so
Yeah, one
One reason is that idea of
You know, sort of the the whole body yes or the hell yes, right.
Because I think often we really want a yes.
And so we're very, very biased to look for a yes.
versus accepting no, that was a no, right?
If someone kinda made this space,
Like that's a no. It doesn't matter what comes out of their mouth.
Right.
And so
The the challenge of accepting the response
Is
Often that of
Yeah, if hearing the no.
But not
Over accepting or under accepting?
Because I think
Sometimes what what people who are really afraid to ask will do is they say, Oh, well, that was a no, so it's no forever, and I should never ask again and my dream is dead and nothing's ever gonna happen for me again.
Right.
And that's because they get so scared, right? But actually no, like that's over acceptance.
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, right, in that sort of more
Control freak.
mode. I think for them.
They'll they they'll often sort of
kind of skip over the response. Say, Well, you know, they said no, but they don't know what they're talking about. Or they're my direct report. So
You know, they have to do what I say.
And so
These are all these are all kind of
You know, these are all kind of fundamentally disrespectful ways to operate in this relationship. And when we're talking about asking for what we want.
We're talking about influence. So you need to have good relationships. You can't be influential with bad relationships.
And so
really accepting the response is about
Yes, I'm gonna be genuine about what I want.
But I'm also gonna genuinely care about you.
And have deep respect for your
Ya your sort of you know ability to consent or not consent to whatever the ask is.
Because I think the counterintuitive thing is that often when we really respect people's nose
Right.
It actually
it can actually be more influential, mo mo more motivating, right? If someone says, Okay, no, I'm I'm not gonna I'm not ready to
deliver it this on time. Be like, okay, well I'm gonna give the project to another person.
Right.
Like I'm taking your no at face value and they say, Oh
Gosh, well I didn't realize that was gonna be the consequence. Hmm. Maybe I can get it done by that time.
Right.
And so that way you're not forcing them, you're not coercing them, right? You're just saying, No, you said no, so that your no is no and I accept that.
So it's it feels like part of the skill here is preparing is like knowing. Some people just say no, and that's okay.
Like you're
That's part of the experience.
Uh part of it is it there's this like not yet component. Uh we had uh
Mihika Kapoor on the podcast. She has a Pyramid Fig man. She had this really
a great approach to being
to building new things within companies is just like
Everything to her is not yet. I know is that not yet.
And the way you phrased it is it could just be the way you asked.
It could be like maybe they'll agree if you can figure out a better way to pitch the thing. Is there anything more you can add there about just this idea of
Uh it's not no forever.
Acceptance of the response is
Primarily an emotional regulation.
Issue.
Right.
Because
Once we get our emotions intact, it's just is it yes or is it no?
Right. And if it's no, which it probably is,'cause most of the time the world tells us no.
Then
The question is, all right, what can I learn from this? What am I 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 ninety nine percent of the challenge tends to be
All the feelings that come up for us when we hear no.
Right,'cause we hate hearing no.
It's so uncomfortable.
And so
part of the practice of getting good at asking for what we want.
is recognizing you're gonna hear no all the time and that's completely normal and fine.
It doesn't need to be something
So scary off.
Easier said than than done in real life.
Is there an example?
of either a client of yours. I know you can't actually share specific details, but I'm just curious if there's an example that comes
Up of someone.
Dealing with this and getting better at it, either or or your own.
Coder.
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 ten years on, you know, I have different perspective.
course and
So this was, you know, almost exactly ten years ago, spring of twenty fourteen.
You know, and I just gotten the job as the first PM at Slack and it was
Already the hottest thing out there. It was only a couple dozen employees.
And I came in excited, but also a little insecure, because I had just come off kind of my breakup with my co founder.
I just wanted to kinda put my head down, you know, put my head down and do a good job.
I was engaged at the time, so Slack already knew.
You know, I was gonna be going away on a bachelor backpacking trip, you know, I have wedding and honeymoon.
Nefowl.
And so I kinda came in
kind of naive and overconfident of like I've been a founder, I've worked on iconic products, I know how to do this, I'm a pro.
I'm just gonna go in and do the work.
And so
Instead of
getting really clear on what does success look like here, or what's your culture, or like
You know, what are your expectations of me?
I kinda just went in and made my best guess and went for it.
And lo and behold, turns out like what I came in with that supreme overconfidence was not what they wanted at all.
they you know, they had 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 kinda 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 no's.
And I wasn't articulating what I wanted. And what I wanted was really very basic.
I just want 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 and you need to have a good relationship with your boss.
But the problem was, you know, in this sort of in the first firing anyway.
Was I had not
I had not articulated those goals.
And so
I shouldn't have been surprised when six weeks into, you know, my tenure at Slack I came back from my backpacking trip with my bachelor.
Bodies.
And I had an email in my inbox saying, Hey, you're fired.
Right. Like
Yeah, it seems like it's not working out. Let me know how you want to wrap it up.
So as you can imagine, I freaked out, right? I loved this job. I love this company. So I profusely apologized. I said, you know, I'll do whatever it takes. I'm so sorry. Um, you know, I'm I'm I'm gonna be committed to turn this around.
And so early stage startup turns out firing doesn't always stick.
Monday morning I had my job back.
But
Obviously things were not the same as they'd been before because in the second era
Hm.
that what I wanted was sort of better.
Better articulated, more clear.
But all of a sudden that fear that had been under the surface, that insecurity, was now very, very present every day. Because I was terrified, right?
Like, you know, was I gonna get fired, right? Was I gonna not, you know, make the most of this opportunity.
And so
You know, I went fully to people pleaser mode.
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 for the 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 a hundred 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 gonna take the risk, right? I'm too scared of
What the consequences might be.
And so I held all that fear and all those desires of like I just want to do a great job. I want us to be awesome partners and build this amazing industry changing product.
And I never said any of that stuff out loud. I just put my head down and I tried to obey.
And so
You know, as as you can imagine
Right. This didn't work very well, right? Like I was feeling horrible day to day. I was terrified of this guy I was working for.
And so again, I shouldn't have been surprised, but I was when I got fired for the second time.
Wasn't quite firing, but this time I'd come back from my honeymoon.
And I had a phone call on Monday that said, You know
Seems like product management's not working out for Slack. You know, we're actually just gonna get rid of product.
You're gonna be user research, it's gonna be fine.
And
For me, you know, I love user research, but that was the beginning of my career. I was not interested in going back to that.
And what was fascinating was at that point
I was actually able to articulate what I wanted there.
And was willing to say it out loud.
Because what I wanted was no, like what's keep me in product, right? I've got an idea for how we can run it. So
I wrote a
Powerful.
I send 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.
Um and so within a week this
New plan, attraction with the management team.
And
You know, I had my old job back again.
Right, everything was fine.
Except of course.
Wasn't fine.
Because now I was scared, but the stakes seemed really high, right? And this is where kind of that
deep imposter syndrome set in. I was like, am I even any good at this? Like should I even be in product management?
Am I ever gonna work in this industry again? Is this gonna be my dark secret that I take to the grave?
That Stuart Butterfield fired me three times.
You know?
And
And so
You know that.
What
I think what what I couldn't be with in that moment was was the no's, right? Cause I was getting no after no after no after no.
You know, from
from Stuart and the rest of the management team.
Saying, Yeah, like what you're doing is not working for us, right? Like your ass are not landing, like you're not being effective in the way that you want to be effective.
And
Because I wasn't able to hear those no's again'cause it 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 what's right.
Against
Oh, evidence to the contrary, by the way, is this like product luminary visionary
famous person, right?
So, you know, clearly not not based on on any facts, but it was an emotional issue, right? Of like I couldn't deal with the reality of
What I was doing.
Was not working.
And so again.
Because you know, I was not articulating what I wanted, I was not asking for it, and I certainly was not listening to the 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 HR.
So it turns out once you hire HR
The firings are final.
Um
And so I only made it to a year at Slack and it was a year of just utter torture because I spent that year
being fulfilly with myself.
Right.
Never saying what I really wanted, how I really felt.
Because he didn't feel safe. I was too scared.
I kept it all inside.
And it took me
six months or a year even after that to really feel
Safe and okay again, right? It was a serious decompression time.
My wife and I had a baby during that time.
You know, I was on zero sleep.
It was a rough
Rough period.
But
You know, the irony is is that like when I actually came out of that experience
Like the reality of it was extremely simple, right?
I hadn't articulated what I wanted, I hadn't asked for what I wanted, I had not listened to the nose that
In response to my non ask.
Right.
And so of course I was unhappy with the result.
Right? Like why would I have expected anything different? I wasn't the victim, Stuart wasn't the villain.
Right.
Like we were it was just ineffective asking.
And so
To me
Especially because I was already on that path towards coaching.
That lesson hit really hard.
Right, in terms of
Like, how do we make this work more sustainable?
Right, we stay in integrity with ourselves, even when it's hard, even when it's scary.
Right, even when we don't know exactly what the outcome is 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 have suffered and how much a lot of people suffer in these similar circumstances.
And
All you have to do to turn it around is ask for what you want. So
This is why I'm so passionate about this stuff because
It sounds so
It can sound so fluffy to say, Oh, you know, focus on integrity, you know.
Honor honor your desires.
No, like it's real life stuff of like a year
of suffering, of pain, of fear, right? Like
I don't want
I don't want other people to be going through that. And that's why I'm so passionate.
about this stuff.
Wow.
What a story.
And I love that it's kind of a microcosm of everything we've talked about. You've kind of did all the things that you teach people to avoid.
Yeah.

Exactly.
And I think what's interesting is you kind of went through these three phases. Interestingly at the beginning, your first phase was you were not hearing the nose.
But it was rooted in this confidence that you're a founder, you're awesome. They're so lucky to have you. I know what I'm doing. Get out of my way.
And then the s the third phase you also the issue there was you weren't hearing the nose, but it was more from
Fear of being fired again.
And so it's interesting that there's these different reasons you're not
Hearing
what people are actually saying.
Totally. Well, and and to me the first one is about articulation as well, because I think that
If if in the beginning it articulated that
Yeah, I'm confident, but I actually I wanna do a really good job, right? And I wanna have good relationships. So let me
Let me think about intentionally
How do I create those outcomes?
Right, but because I hadn't articulated that's what I wanted.
Right, like it didn't even occur to me like oh yeah, I need to like do some intentional relationship building.
you know, figure out some metrics for success. Cause an early stage startup, right? Like
It w 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.
I imagine you've gone through this exercise bef many times, but say you were to do it again, what would you
Do differently and
What do you think would have happened? Do you think you would have s stayed there for many, many years, been had a product that's slack at this point?
Just imagining that reality, what would you have done differently and then what would you have imagined have
Turned out.
Well, I mean, obviously broadly, I would have asked for what I wanted, right? And what I wanted was I wanted to do the best work of our life, right? I wanted to have a
deep professional partner and the CEO and the rest of the product and management team.
And yeah, I wanted to produce great work that people 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 what I would have done.
Now
Do I know what the outcome would have been?
No, I might have been fired even sooner.
Right. But they might have said no, you know, like this is not working out. Like let's just
Let's just be done.
And so
That's what's tricky about this is it really isn't about the outcome.
Right. Of course asking for what you want makes you more likely to get the outcome you want.
But
You don't do it
you know, for guarantee of a certain amount.
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. Cause at least then I would have said
You know what? Like it didn't work out.
You know.
At least I'm not sitting here suffering, I can get another job and another startup.
Right? It's not the end of the world.
And I think that
mistake we make is pretending that it is, right? Of saying, you know, going into fight or flight and saying this is like a
severe existential
threat to who I am and sort of my safety in the world versus being like yeah.
I'm disappointed. I wish it had worked out, but it didn't.
That's a really profound point.
that
You don't this this practice isn't necessarily to just have everything work out beautifully.
And to get the things you're looking for. It's
to feel like you did, which you could have
And to feel integrity with yourself that you did.
What you needed to do and
You didn't you're not gonna regret.

Something down the road.
Indeed.
I wanna 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 Piano startup.
Join us the first PM.
I imagine you work with a
People asking for advice along these lines.
It's classically a very challenging role. Many people don't laugh. Many people follow your trajectory where it's like, Oh shit, what have I done?
Any advice for people that
or a first PM at a company or startup.
Or thinking about that role.
How to
What can you tell them to
Help them.
be successful or at least
Uh
At least not not suffer.
To me, it really is about the relationship with the CEO or with the founders because
That sort of the
the the root of a lot of the issues that come out of that scenario.
Because it's not always you. Like in my story, I think it was primarily about me.
But I also work with a lot of founders who are going through really tough things. Like my
My my clue to
people who report to a founder is to say
Imagine if you're can if you're confused about
how your founder is behaving, imagine that they're terrified all the time.
Right. And see if that makes their behavior more clear.
Because it is scary to be a founder, right? Everything's on your shoulders. And I think a lot of people do feel that
sense of high stakes all the time.
And so
You know, I think
being real about that of like what is the state that the peop the person or the people you're working for are in.
And sort of working within that versus sort of
pretending that it's something else or wishing that it were something else.
is sort of the path to having a healthy relationship. Because if you don't have a healthy relationship
with the person you're working for, you're not gonna get anything.
You're not a ca you're not gonna succeed in any
Meaningful way.
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
What should people look for to d to help them understand if the founder and them are a good fit?
if they're gonna have a good time working with that founder. Is there anything just like questions they might ask or
Ways of operating that are useful to understand, like, okay, I think I'll be okay with this founder in in this
In this company has the first PM or not.
I think it's a hard thing to generalize about, but
To to me it really is about understanding expectations, right? Of like what do you you know, I mean, I I guess this is, you know.
A predictable coming for me, but what do you really want?
Right.
Because I think that often
you know, the founders put together a job description, but then they're faced with a real human being who has real
sort of human subtleties and things they're good at or not so good at. And so
being very, very clear about expectations and I've
figuring out collaboratively a way to work together that's effective.
To me is
You know, the close the close there's no guarantees, of course, but it's it gives you a a sort of more sure path to having a productive relationship. And
It's actually something that I I recommend to a lot of founders.
for you know, maybe their first, you know, ten or fifteen or twenty employees of
Just have like a relationship design conversation with each of them when they're first hire.
Because
I think a lot of us
come in naive the way I did, assuming, Oh yeah, I'm just gonna come in and kinda do my thing the way I've always done it, it's gonna be fine.
versus coming in and saying
I actually don't know.
how I'm gonna operate at this company, right? I have range like anyone has range, and I don't know what this company needs and
Who else is here and sort of
What what my role and what my place is gonna be within these other people.
And so by
Really
understanding that intentionally and not
From a place of
Performance management, you're already doing this poorly, you're in big trouble.
But a yeah, what is the best way to work together given who we have now and what we want and what we need.
Let's figure it out.
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.
I'm asking for what you want. Anything else you want to leave listeners with?
I 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 of of fear and focus on what I want?
Well
I mean, I've been running from fear my whole career. Like that's how I'm so hard working and how I'm so smart is
I'm always afraid I'm not good enough.
Like
Is you know, am I gonna be able to do this job without fear hounding me every step of the way?
And I just
And I I just remember the first time I heard this, it broke my heart. And now I've heard it
You know.
Dozens of times, I'd say.
So I mean it really is I think it's a belief that sits deep in the hearts of a lot of
Uh
high achieving Silicon Valley tech types of
You know, my fear of not being good enough is what drives me to be great.
And I just wanna come out here and say
There's other ways to motivate.
Right.
You can motivate based on joy, based on vision, based on
You know, you're
you know, inspiration in this vision of what you want.
And you know, I think a lot of folks I talk to are skeptical, understandably,'cause they've they've operated a different way their whole life. And
All I can really say is try it.
Right. Try following
An inspiring vision that's really meaningful to you.
And just see what it's like to not be sort of living in fear all the time because it is
It's a big difference. And um and it's really meaningful. It matters a lot.
So is the idea there, is the fear there that if they ask for what they want, they'll get what they want and there's
they let go of kind of this drive to prove themselves and
Is is that the fear?
Like how was it that they
Move away from that.
Uh
need to prove themselves in.
Well, I mean that's that that's a longer story, I would say you know.
sort of uh, you know, managing our own fear is a sort of lifelong practice. I'm not gonna claim I'm anywhere near done with it.
But but I guess I 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, 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, achieve my goals, I need to focus on vision, on
What I want to achieve in the world.
Not on avoiding all these fears.
So
That's that's the short of it.
Amazing. We uh it reminds me we have a chat I had a chat with Nat Mashari.
And we spent a bunch of time on dealing with fear and overcoming fear.
So folks wanna dig deeper there.
They can check out that episode.
Okay.
Just maybe one more question before we get to our very exciting lightning round.
I wanna take us to Contrarian corner.
Classic contrarian corner.
Curious if there's anything that you have uh
contrary an opinion about something that you believe
That most other people don't.
For for me, I'm I'm not a big believer in discipline.
Um
You know that I think
You know, some folks come to coaching looking for
you know, sort of a drill sergeant to say, All right, shout at me and tell me to do better.
And I sort of say, Yeah no, that's not
That's not how I operate because
It's not that discipline doesn't work, right? But it's like people pleasing. It's a short term
Um it's a short term coping strategy.
Like discipline will get you in the gym for a week.
But it's not gonna get you in the gym for a year.
Right. The people who are in the gym for a year are doing it because they want to.
Right, there's actually something that's motivating for them in that. That's not just
Oh, I hate this, but I'm gonna go anyway.
And so
You know, I I try to be really clear with people about that, that I'm not
gonna be the drill sergeant because it's unsustainable, right? Like someone shouting at you
Like is not going to
You know

what you want in life over multiple years, right? It's a days or weeks.
Or even ours thing.
And so I really look for a higher bar to say
Yeah, like let's
Let's look for true long term sustainable motivation.
Which means relying on vision, pursuing what you want.
I love that it all ties back to knowing what you want, asking for what you want, and then
Dealing with
The answers that you get.
I I am a broken record, admittedly.
Amazing.
Uh, Kenneth, is there anything else you wanted to share or leave listeners with before we get to our very exciting lightning round?
No, but
Just
Thank you for letting me share this stuff. It really is.
My life's work and I'm very passionate about it and I hope it's helpful for people on
I'm gonna be writing more about it.
Unwedding.
Okay, amazing. We'll point people there.
With that we've reached our very exciting lightning round. Are you ready?
I'm ready, let's do it.
First question, what are two or three books that you've recommended most to other people?
Well, I already mentioned radical candor. I think that is for sure a modern classic.
Um and I think that
That whole idea of
sort of challenging directly, but caring personally is very much aligned with
What I'm talking about, right? Because
You know, you need the relationships and you need to actually speak your truth.
So
I I love, you know.
Kim Scott's writing on that stuff.
We had a Kim Scott on the podcast, if folks wanna dig deeper there, we'll link to that episode.
I'll let you keep going.
Sorry for the interruption.
Yeah, you have I mean you've s I I mean I I mentioned before, but I I actually took um uh Johnny Miller's nervous system mastery course. I just wrapped up.
So
You've had lots of great personal professional development thinkers on the pod, so
Thank you for introducing you to.
I'm so happy to hear that. We'll link to that episode as well. Uh I love that. What a circle circle of life we've got here.
Guests following other guests taking their courses, joining the podcast.
What a happy world.
Yeah.
Indeed.
Uh okay, any other books?
Before we move on.
I I also love the uh fifteen commitments of conscious leadership.
Um, so I I I'm pretty sure other guests have mentioned that as well, but
To me part of why I like that is that I think a lot of
personal development books are are not very directive. They say, Oh, you know, you just
Dig deeply and find your truth.
And while there is value to that, of course.
I think sometimes it's nice to have some direction of yeah, here's fifteen things that like generally your life's gonna be better if you do them.
And so I I to me it's a nice balance of
embracing
the really deep stuff of how to live a good life and be effective in the world.
And be really directive. Like, yeah, try this stuff. It works.
Do you have a favorite recent movie or TV show you've really enjoyed?
Mm-hmm.
I'm a recent tennis fanatic, so
was one of the things I picked up during the pandemic. So
I really enjoyed Netflix's break point.
'Cause it's a documentary on the best tennis players in the world and
It is just
I I just find it so
I don't know, I it's it's it's just beautiful seeing how everyone is kind of the same because all these people
They all know all the strokes perfectly. Like they're technically perfect in pretty much every way.
And so it really is mental.
Right, for those folks
It is about working through resistance as well, right? When they have a narrative that says
Oh I'm behind.
The other person's better.
You know, I'm I'm not gonna be able to do this.
Right.
Are are they believing that?
Or are they working through that resistance and saying, You know, that's just a story. Yeah.
I actually don't know what's gonna happen.
But I'm gonna try to win.
I love that you see coaching opportunities in every
Everything even even
Uh entertainment.
I also love I mean actually, you know, speaking of
I mean it's almost two on the nose, but
There's this movie Living from a couple of years ago, um the this British actor who's this sort of
You know he's he's he's this sort of you know.
tough old sort of, you know, stodgy government office manager.
And he gets diagnosed with cancer.
And he has this real transformation where he thinks about, God, I've just been sitting in office filing papers.
My whole life.
What do I actually want to do with the last months of my life?
And
He he builds this playground for children and that's actually his
His legacy.
Sorry, actually spoiler alert. Whoops, shouldn't have
Uh you mentioned tennis and you mentioned British people.
Uh I will actually be at Wimbledon this year in London.
With my dad in the
July and we're gonna host a meetup there while I'm there. Just for anyone listening right now, just to give you a heads up.

How fun is that gonna be?
Okay, next question. Do you have a favorite product you've recently discovered that you really love?
Uh, well, you know, it's it's funny. I I used to be a big wine aficionado and I think as as with many of us, I am
Discovering I feel better with less alcohol in my life.
And so one of the things I've been picking up is uh oolong tea. I've got a little
Cup of
Taiwanese, Wenshang, Bao Zhang.
in front of me and um
I feel like it's like all the nurdery that I put into wine of like
regions and varietals and history and processing
But it's actually good for me.
It's like full of antioxidants and makes me more focused and I can drink it during the day and
So yeah, I've been totally going down a nerdy tea rabbit hole.
And I I recommend it.
Taiwanese mountain tees, especially.
I gotta give me some of that. That's actually I always have tea here when I'm doing these podcasts. I got Emma
Less sophisticated tea drinker, I just go with Earl Grey, but like a really nice Earl Grey.
And so I'm gonna have to
buy some of this. Uh, do you have a place in a brand you recommend most?
There's lots of there's lots of great stores online. Uh you can check out TeefromTaiwan.com. That's a good one.
They're gonna get a bunch of traffic. They're like, What the hell just happened? He from Taiwan dot com.
Amazing.
Do you have a favorite life motto that you often come back to, find useful?
Share with work.
Share with friends or family.
And work currently.
I mean I'm pretty sure you can guess what he I wonder what it might be. I wonder what it might be.
So this is actually part of why I I 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.
Um
Because yeah, it's it's the best advice I have.
is to ask for what you want.
It all just comes back to that.
Final question.
We've been talking a lot about asking for what you want.
Kenneth.
Burger, what do you want?
Ooh.
All right. Um
Well, you know, I think
For me, you know, Wenny, you're you are already uh you know
industry womanary with, you know, thousands of followers.
I am
I I'm interested in in sort of sharing more of these ideas. So if you y'all would come follow me on LinkedIn and
Subscribe to my newsletter. I'm
gonna be exploring these ideas and sharing more of this stuff'cause
I just I'm so passionate about it and um 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'cause 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's right. That's right. So yeah. So I I'm I'm 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 what you want, right? I mean
For me, it's not just about
my vision and my framing, but
Like I'm a coach, right? Like I'm not just about big ideas, I'm about making a difference for my clients.
And so I realized, yeah, if I really want to make a difference with people, I need psychic 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 and sort of really get into it. So
That's that's kinda why I've been putting myself more out there.
Amazing. So kind of 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?
Um so you can find me on LinkedIn. I'm Kenneth Berger, B E R G E R. Um, so please follow me there, subscribe to the
Ask for what you want newsletter.
And um
Yeah, you can check out my website, k burger.com, K B E R G E R
K Burger dot 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. Thank you.
Hi, everyone.
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