How to build a team that can “take a punch”: A playbook for building resilient, high-performing teams | Hilary Gridley (Head of Core Product, Whoop)

Transcript from https://podmenti.com/t/ee2d8d0008dbf785

Product leadership is
The type of role where if you are not in control of the voices in your head, they will eat you alive. You spend a lot of time thinking about how to help your team learn to take a punch. If they come to me and they're upset, I try to focus them less around how you litigate another person's impression of you and more on what is the action that you can take. To counterprogram the narrative that you are
Afraid that this other person has of you. What are you going to do next to demonstrate that you are the person that you know yourself to be? Do you have specific tactics that you teach your team to deal with hardship? I would really love it if more people were like, screw it, I'm gonna do something that's probably gonna fail. It's important and it's worth doing, and I'm gonna do it well. Is there something you've learned about when your leader tells you to do something you disagree with?
The game is all about influencing the CEO, influencing the people around them. You come up thinking like you're the protagonist, but in the story of work, you are probably not the protagonist. You're not special.
Today my guest is Hillary Gridley. Hillary is head of core product at Woop.
Previously she was a senior director of product at Big Health.
And a senior product marketing manager at Dropbox.
Even more importantly, she wrote what is now the sixth most popular post of all time in my newsletter, how to become a super manager with AI.
She's also the first ever crossover guest between this podcast and our sister podcast, How I AI with Claire Vaux.
And not just that, her episode with Claire is on track to be the most popular episode of the podcast. So all that to say, Hillary is incredible and I'm so excited to continue learning from her.
This conversation is packed with advice that will make you a better product leader, builder.
And also just a better human. If you know it's good for you, you don't want to miss this episode.
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With that.
I bring you Hillary.
Gridley.
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Hillary, thank you so much for being here and welcome to the podcast. Thank you, Lenny. I'm so excited to be here.
I talked to a bunch of people that are work with you about what we should talk about and what you're amazing at.
Uh, first of all, every one of them loves working with you so much. One one of them's like I joined Woop just to work with Hillary and to report to her.
And
Of that a theme, there's kind of this theme that emerged that I think is a good kind of overarching theme for our conversation.
And it's something that you spent a lot of time thinking about.
And it's
How to help your team and how to help
People within your company, learn to take a punch.
Essentially how to help them deal with hard stuff and do hard stuff and build
Or things.
So I guess just broadly, does that ring a bell? Does that resonate?
Yeah, absolutely.
It's uh it's something I care a lot about. I've been
I think pretty lucky in my career. I've been very drawn to working on
Hard
Product problems.
Uh
regulated areas.
Ah, really hard business models.
Uh things with pretty high emotional stakes for the users of the products.
Um
You're really likely to run into a lot of setbacks along the way.
And I think this is really relevant today because I look out and I I talk to a lot of people and
I hear
Fear and I hear uncertainty.
And I think it comes from a few places. I think um
Obviously I'm really excited about
AI and how it's transforming the way we work.
And I think a lot of people are, but I think a lot of people are scared too.
And they're embracing these tools, they're learning these tools.
But a lot of them have a question in the back of their mind, like what does this mean for the future of my job?
And in many cases, what does this mean for for my identity, right? Like I think it it makes people question
Um
Even just how we
Provide value as humans in society.
And I also think, you know, the people, especially young people today, haven't even necessarily been in a career environment where there wasn't always kind of a threat of layoffs or things like that.
And I think that's taken a real psychic toll on a lot of people.
And so I think all managers now really need to be able to lead their teams through uncertainty, through fear, through hard things.
Um, and I love the concept of taking a punch. I've got a a couple other tools that I I like to use.
Um, but I think it it can teach people how to
thrive in these environments. And it's really important to me because
I would love if more people took on hard things. I think there's so many really hard, challenging problems out there to solve.
And the more people are kind of fearful about the future of their careers or the future of work.
I think the more they gravitate toward things that
they feel like they're likely to succeed at.
And I think
That's
Wonderful. We need that too.
Uh, but I would really love it if if more people were like
Screw it. I'm gonna do something that's probably gonna fail. And uh
It's important and it's worth doing and I'm gonna do it well.
There's so many m kind of N diagrams of why this skill is so important, especially today.
One is it feels like the easy stuff is is done. Like the stuff left to build is hard. Like
It feels like hardware, deep tech is where things are heading. Also just like
machine learning, AI skills, just like stuff that's really hard. And then the other is just AI is
just changing so much. It's just such a stressful time and hard time for a lot of people.
Let's actually walk through some of the things that you have
learned about how to help people get good at these things, about how to learn how to help people learn to take a punch.
Uh AKA do hard things, deal with struggle.
The first is you actually actively teach them. Like you have specific tactics that you teach your team.
Two
Deal with hardship and to
Take a punch. So what are some of those things? What are some of the things that you teach your team and help them develop the skill?
Uh, so at its core, when I say take a punch, what I mean is you're going to run into situations where
Something has gone wrong. Uh maybe you have misstepped, maybe you are just hearing someone speak critically about your work, whatever it might it might be.
you're gonna feel like you have taken a punch. Like it's a very
physical feeling.
And I think as managers you spend a lot of time
Teaching your team
how to be successful, right? You you want to prepare them.
To maximize the chances of a good outcome, but if you don't also prepare them for what happens when that outcome isn't as good.
uh you're gonna run into some problems.
And so
When I think about how to take a punch.
What I say to my team is
If they come to me.
And they're upset because something has happened, uh, maybe they
said something in a meeting that wasn't received well.
Or
Again, they're hearing somebody else talk about them in some way, whatever it is.
I try to focus them
less around whatever happened and how you litigate
another person's impression of you based on something that has already happened.
And more on what is the action that you can take next.
To counterprogram.
The narrative that you are afraid that this other person has of you.
And
I think the counter program piece is really important because
Whenever we feel our ego's injured, I think it's very natural for all of us to say, like, well, that's not fair. I want to correct the record.
When you do that, I I think more than often, more often than not, you come off as as just looking defensive.
And you kind of start obsessing over things that you don't actually have control over.
Uh, which is what another person thinks of you. And you don't even necessarily have that information.
And so I always ask myself in these moments what is one thing that I can do.
Small.
That will demonstrate
The opposite.
Of what I'm afraid this person thinks of me.
And so I'll give you an example of this. Um
I was in a meeting a while ago and we were talking about different things that we wanted to start tracking in the WOOP journal.
And our
Chief Technology Officer suggested ketamine tracking.
And
I thought she was making a joke and I laughed.
And she looked at me very seriously and was like
This isn't funny healer. Like this is a serious issue for a lot of people.
Uh and it's it's an emerging
Uh
Problem in some cases.
And I think we should take it seriously. I think there's a lot of value we could provide here.
А вас completely humiliated, uh humiliated because
I actually
take this stuff really seriously. Like I take addiction really seriously.
I have a ton of empathy for for people who struggle with it.
And
I also think of myself as somebody who embraces
new ideas and wants to be on the forefront.
And uh wouldn't ever laugh off something that kind of seems like a fringe issue.
That's I think becoming actually more and more
Uh um
Big part of what's happening today.
And so
I realized that in that moment I was having that reaction
Because of the
The feeling that it gave me about
Who I am as a person.
And I became so worried that this other person had the wrong impression of me.
And I wanted to follow up with her after and and say, like, let me explain myself. Like, let me explain why I didn't mean that or whatever it is.
But I just as I said I think
I think usually that you're fighting a losing battle when you're trying to do that. And it draws attention to the thing that you kinda did.
poorly. Uh and you don't really want to draw more attention to it, right? You want to move on, take action, move forward.
And so I thought about well what
What am I afraid that she thinks of me?
I'm afraid that she thinks that maybe I don't take
Uh some of these health issues seriously.
I'm afraid she thinks that maybe I'm somebody who uh
kind of like laughs off.
Emerging trends.
Um and so
I thought about
What's something that I could do to demonstrate the opposite of that?
And I did some research very, very quickly on um
you know, what are some like emerging public health concerns that people really aren't talking about? That would be interesting to track.
And I found some interesting research about sports betting and especially young people in sports betting. And it's sort of becoming this thing that a lot of public health experts are very worried about.
And
So I very quickly just sent her a a note that said
Wanted to build on this idea you had today.
Um
I really liked that idea, by the way.
I you know, I saw this this article or saw this research about this other emerging thing, sports betting, and I think it'd be really e interesting for us to start tracking that.
Because we could maybe draw some correlations between
People stress. We have stress monitoring whoop, we can track our stress.
Uh, we could draw interesting correlations between betting behaviors and stress levels.
Um, and so that's all I did. It took me
Five, ten minutes total.
Um, but I think it it's a great example of sho sort of showing this idea of like
counter program that narrative, don't don't fight about the narrative.
And so when I teach this to my team
I'm always doing the same thing. They come to me
Uh, they seem kind of agitated about something, and I say to them, like
It seems like this is really bothering you. What
What's going on in your head? What are you afraid of? What are you worried about?
And often it will emerge, you know, I'm worried that this other person thinks I'm bad at my job.
I'm worried that this person thinks I'm an idiot, whatever it is.
And I challenge that. I think this is really important for managers too to kind of challenge this negative thinking when you see it happen and not just sort of validate it and allow them to go down these negative spirals.
I challenge it and I say
First of all, I don't
I don't think there's evidence for that. Is there evidence for that?
And you know, even if there is
It doesn't really matter.
What's what's something that you could do to show them that's not true? Because you know it's not true.
Um and I think
Giving people that that power to focus on the next step they can take and the action that they can take.
That helps them
feel more secure in their identity and who they are because their action demonstrates that.
Um, it just gets them out of that negative thinking and it gets them through that.
Trough of
Despair that comes after you you feel like you took a punch.
So the idea here is when you're afraid somebody that matters in your career thinks ill of you of of something that you did, of you're not good at something, or you think something
that they're not happy about
Like this is a version of getting punched, basically, is you just feeling like someone

And so the tactic here is how to change their mind almost about you and give you something tangible to do.
Exactly.
Okay. And so the question to ask, and I wrote this down as you were talking is
And this is what you ask of your reports. What is the one thing that you can do that demonstrates the opposite of what you think this person thinks about you?
Exactly.
If it's i i this comes up all the time, like
There will be narratives that emerge. Some are good, some are bad.
Um about you and your career.
And I think especially when people get to a place where
They're putting themselves out there more, right? They're talking uh in more presentations, they're talking in more meetings.
It's very natural for them to become
Concerned with the perception of themselves.
And it is scary because it it feels like something, as I said, you don't have control over.
And so exactly if if it's in if instead of focusing people around what do these people think of me
You focus them around well, what are you going to do next to demonstrate?
That you are the person that you know yourself to be.
Uh, I think that can just be incredibly effec effective. It
giving people more of a sense of agency.
I guess talk about the balance of
I'm just gonna
Prove everyone.
wrong against what they think versus here's who I am and I know this is me.
And it this person is mistaken and instead of debating them.
I'm gonna show them who I am. Just like not over stressing about everyone thinking things about you in different ways.
There is s some value, I think, in having a little bit of a chip on your shoulder. I think that that's definitely been you see that people who are really successful.
They do have a little bit of like I'm gonna prove them wrong.
And so I don't want to say that like you shouldn't think about it at all or you shouldn't care. Like of course it's natural to care and of course it's fine to care.
But I do wanna just sort of help
Help my team build this habit of
Doing the things that
you know to be right and and having conviction in that and
You know, being open to learning along the way and and sort of calibrating as you go.
Um
But not not becoming overly concerned with
your fears of what other people are going to think of you because I think
Especially for
otherwise really thoughtful
You know, really kind of
The peop people who are kinda hard on themselves.
I think that that just holds them back from
being the person that they can be.
So a key part of this is this is gonna help you stop just spiraling on
Thinking about what they think about you and gives you something to do that will change that.
And then the other key point here is don't try to convince them otherwise. You're not gonna go to your manager like
Oh, I'm I really l think ketamine.
There are being
addiction is really important and I'm
I didn't mean to say it this way and that kind of thing. I you know, I'm not interested in litigating the things that happened already when we can move forward. And I'm certainly not interested in litigating
What another person thinks about a thing that happened.
Uh I just I feel like I've spent so much time talking to people in meetings, whatever it is.
Where it's just this kind of like
ruminating on something that has already happened.
you know, it's very like anxious thinking pattern, I think. Um and people can just get stuck in it.
Uh
And so
Yeah, let'em
Let let them do it.
Like I often think about
Uh it's like when you get bad feedback, right?
Uh or critical feedback.
And you kind of naturally have this reaction of, Oh well
No, that's not fair'cause they don't understand.
I actually have numbers I have to deliver on or like
I only had ten minutes to do this. So like of course it wasn't perfect. Like you you naturally come up with these reasons.
Why?
Uh you're actually
Not.
Wrong?
Any
And that's fine. Like it's I don't want to say like you should feel bad for doing that. Like let yourself have the pity party. Let yourself feel those things.
But then but then you gotta move on as quickly as possible because those feelings
They actually do tend to spiral and get worse, um if you're not
actively working against them.
Oftentimes these sorts of lessons come from
the person experiencing this themselves. Is this something that you dealt with when you're starting your career or even now and
Oh absolutely. Um
Hundred percent.
And I think it is more than just my career, but
just my like general mental health in my life.
A lot of where this comes from is uh
A a concept in
Cognitive behavioral therapy called behavioral activation.
And in my former job, I was working for a company called Big Health, and I was we make uh digital therapeutics.
So those are
mobile apps that have been clinically validated to treat.
behavioral conditions like
Insomnia, depression, anxiety.
And I was working on a new depression therapeutic and so went very deep on this.
Um, and was working with
A really wonderful clinical team full of clinical psychologists who helped me understand.
The techniques that therapists use.
uh when they are working with people who have depression.
And so much of depression is characterized by
uh these negative thinking patterns and this like this feeling that
I feel bad.
And
I just need to wait until I feel better and then I'll start doing the things.
That
are good for me, right? I don't feel like
Uh
responding to this text. So I'm just not gonna do it, but I'll respond when I feel better.
I don't feel like working out, so I'm not gonna do it, but
I'll do it when I feel better.
And the truth is I
Yeah.
That doesn't go away on its own, especially if you have depression. Um
And it's something that
Again, you you the idea of behavioral activation is
Uh you have to identify these actions that you can take.
That will reverse that negative spiral.
I will
Improve your mood.
And so the the sort of like misconception is
I'll feel better and then I'll act.
And the thing that therapists try to teach people, when they're working with them in therapy, is
I will act and then I will feel better.
But acting is hard.
If you are in the throes of depression.
And so easier said than done.
And a lot of the work is in how you I help people identify specific actions that they can take.
that will reliably lift their mood.
And I I mean I have a list of myself. I've had a a list on my phone of my behavioral activations, and it's things that
I know I can do.
If I start feeling like the walls are closing out around me, if I if I like feel myself kind of getting sucked into
uh like very low mood or negative thinking or whatever it is.
And you can you can see how effective that is at just getting you out of there versus the instinct to just sort of like go and lie in bed and feel bad for yourself.
Um, which I I understand very well.
And so that
Understanding that concept, which is at you know, at its core a therapeutic concept used in cognitive behavioral therapy.
Um
But it kind of it kind of changed how I see the entire world.
Um and I how I see
Especially as a manager.
The ways that people on my team
Think and behave.
Uh, and how easy it is to get stuck in some of these like
downward spirals that you really need to actively push back on.
And as a manager, I want to help them do that. I want to help them a see that like see the ways they are.
In some ways, sabotaging th themselves, getting in their own ways.
Um
With
Whatever is going on in their head.
Uh and then I want to help them
Counter program it in themselves.
And also, you know, as I said, counter program the things that you are worried about out there as well.
So interesting. So the core of this technique is
What's a s an action and you said this it could be very small. Very small that you can take
That
In this case shows someone else you're not they're not you're not who they think you are. Like
You're worried they think think about you in a certain way and you want to take an action that
Helps them see you're not that.
So that yes, that's the taking the punch concept. The behavioral activation could be anything, right? It can be it can be picking up a
piece of laundry off of the chair and putting it away.
And that's just sort of enough to get you out of the downward thing you're in.
So behavioral activation just conceptually is
Uh
You know, how are you taking action?
to reverse the the downward feeling the negative feeling that you're feeling.
And then the take a punch concept is kind of that applied
In the context of
I'm in a working environment.
I am very conscious of how I'm being perceived by other people.
That's causing me a great deal of stress, I think, especially for product people.
Who are um
you know, so much of their self identity is wrapped up in
Having the answers.
Being competent, getting things done.
Um and so many of them have been
People who've been really good at that for most of their careers, which is how they got into these jobs in the first place.
I think that can be an e extremely stressful thing for them.
that in many cases can be uh like the driver of burnout and the driver of like
I I can't really handle the stress of this job anymore.
Um and so I think of the the take a punch concept is is more just applied to that sort of specific problem of
I'm struggling at work and I'm struggling largely because of my perceptions of other people.
Uh, and I wanna feel more agency in that situation.
This is so cool. Okay. On the
Idea of
the specific take a punch concept. What kind of
impact have you seen this have on
people's mood and careers. Is this like how big a deal is this specific tactic?
Well, I think it's a big deal, like
On two levels. One, it's a big deal because it can help you in a crisis or a minor crisis.
But I actually think it's a bigger deal because
I see so many people who don't
uh put themselves out there because they're afraid of how it's gonna go.
And so I think of the like classic example of um
I'm often trying to encourage people to like speak up in meetings more.
uh to
Practice the skill of how you move a conversation forward.
In a way that contributes value.
Uh, both because doing so I think is is important because nobody wants to be in bad meetings.
But also because it will help with your career, right? Like this is how you kinda get on people's radar as somebody who's like, Oh, that person's got
Great ideas. Think about things the right way, whatever it is.
I think it's just it's one of these things that I
Talk to people about it.
And the you know, they they are
interested in coming to the meeting and hearing about
Uh these big decisions are getting made.
But they just kinda wanna sit there and observe.
And I'm like, first of all, like every additional person in a meeting has a cost because every additional person
In a meeting makes the people in that meeting less candid.
than they would have been if there were fewer people in that meeting.
And so one key piece of a meeting is like
You usually have a problem you're trying to solve.
Uh collectively as a group.
And it's really hard to do that if people are being overly cautious about what they're saying.
because there's like too many people in there. So
Uh when I tell people this, I'm like
You know, it's really important that you earn your place in this meeting.
Uh and let's work on like how to do that.
And the core piece of that is like you've got to say stuff that's valuable.
And people always come up with all these excuses for why they can't do it.
And
One thing I've learned is that
I think people are really good at coming up with very rational sounding reasons to not do things that just make them uncomfortable.
Uh, but in their head, they're like, Oh no, you know, like
I'm I'm too junior, like nobody wants to hear what I have to say, or everyone was already thinking it, or
Uh, you know, I you know, I like to process things internally and by the time I say them, the conversation's moved on, whatever it is.
Um
And so so much of like that skill, it's like a communication skill at its core, it's just how to express yourself verbally.
Uh but so much of the the blocker of that is I think fear.
Uh fear of saying the wrong thing.
Fear of looking stupid, fear of just
The uh the discomfort of everyone in a room turning and looking at you.
Right, as you're kind of like trying to formulate a half baked thought.
And so if you can help people be less afraid of that.
That's like ninety percent of the challenge of actually improving some of these skills.
Um, and so I think
When you give people the skills taking a punch
You are helping them feel less afraid of getting the punch in the first place.
Um and that's why I think it's so important.
That's profound.
The second order effect of the skill.
There's something you mentioned when we were chatting earlier that um stuck with me with this idea that too many PMs and too many people are playing on easy mode and not trying hard things.
Uh oh. Okay, let's do it. Say more.
Mm.
Oh I think this is my hot take. Like
You know, you hear people talking about craft and taste and product management and it's all very wonderful.
Um
And I I'm like totally on board. Like I love it. I'm I'm a sucker for that kind of thing.
But I'm like
Well if if
If you are like really in it just for pure love of the game, like you just love product management.
Like why are you building products for people exactly like you?
Who have all your exact same problems.
At a company that
sells to other companies that
Doesn't
worry about pricing. Like there's no real bear. I mean, there's I don't wanna I don't want to act like I think this is easy to be clear. Um
But in the like the grand scheme of things, like
I wish that
the people who have this pure love of product management and have this pure love of building things.
that you would see more of that applied to
Building for low income people, building for you know social services, things like that.
That really really need
That kind of work.
Uh, and I think there's a yeah a level of prestige obviously associated with working
Uh in certain companies and
you know, you get less of that in in other industries, and so people naturally gravitate toward that.
Uh and I you know, I totally get it. I totally get it. And you get paid better like
No no real judgment for me.
Uh
I just
I wish I saw more, but I wish you would see more people. And I'll say this, I know there's a lot of you out there, I know there's a ton of people out there.
Doing really, really important work in really really hard spaces.
Uh, and I see you and I I appreciate it. And
Shout out to you.
Awesome. Okay. I'm glad you shared that. Thank you.
I think this will resonate with a lot of people.
I wanna move on to another trait slash habit slash skill that you
are good at and help people learn.
Which is being very transparent.
in what's happening within the organization, within your thinking. You almost help people think the way you think and see the way you think so that they can operate at a higher level. Just talk about that, what that looks like and why that's important.
It's interesting. I think another thing I hear a lot of people complain about in
organizations is like the
Why do ten people have to sign off on this email before I send it?
Kind of problem?
And I think the answer to that is like
Because those ten people
All have
Different information.
Different context.
And
In many cases, completely different like working models for how
the CEO of the company and other strategic leaders in the company think.
And
It makes things super inefficient.
I think people will often say like oh it's a process problem. It's it's not a process problem, it's not an approval process problem.
It's a I think it's a transparency and it's communication problem.
Like downward communication, outward communication.
And what I mean by that is um
When I think about like
artifact based communication. So reading a strategy document, for example. Everyone at the company reads strategy document.
Great. Everyone is working from the same idea of what the strategy is.
But then things change, right? Like especially if you're working in a really dynamic space.
uh new competitive threats em emerge, new opportunities emerge all the time.
This is especially true now with AI. Obviously everyone is lighting their strategies on fire and trying to figure out
the best way to to sort of
transform their organization.
And so if you're
Your the the way that you understand what's going on at the company
Is from reading a document that was written six months ago.
you're gonna be working from outdated information and you're not gonna be able to
Like think and respond to new things that happen.
And so
What is what much more helpful than understanding what your CEO thinks is I think understanding how your CEO thinks.
Um, and that goes for
all sorts of levels of the company. I want to understand how all the strategic leaders of my company think.
And I want my team to understand how I think.
And when I feel confident that people on my team
understand how I think. Like I don't need to read their emails. I don't need to approve things.
The times where I feel like I need to do that is because
I'm working with people where I'm like I don't
I don't have confidence that these people understand how I think, or I don't have confidence that they understand
How this
Uh this email or whatever it is is going to be received.
by this important person.
Um
And
So
I try to teach that to my team.
And the way that it is a a few ways.
Uh first I'm in meetings with
people like important people of the company.
Um, so I'm constantly hearing the things that they're saying and paying attention to
Sort of a note behind the note. Why do I think they're saying this? What do I what insight do they have that they're bringing to this conversation that might not be obvious?
Um
And I try to make an effort every week.
I don't
Always do it when I try.
To send my team just a quick
Rundown and slack of
Here are the most important conversations or the most interesting conversations I had this week.
Here's what that person said verbatim.
Again. I I write a lot of notes, so I've I've got it.
Um, if you've got a transcriber, maybe that that'll help you.
Here's here's what I interpret that as.
Here's why I think they say that. Here's where I think that's coming from.
And here's what I'm going to do differently as a result.
And these aren't long. And sometimes if I don't have time, I'll just like in a teen meeting, I'll literally just go through my notes from the week and sort of voice over stuff and editorialize it as I go.
Um
And over time I think my my team has like a pretty good sense of
what people are saying and and
How to think about
uh the thinking behind it.
And how this person thinks, how this person thinks, and how I think.
And I think when you get
an entire organization working that way where everyone's working from the same models of like
How what the CEO thinks matters.
uh what level of like risk tolerance
the company has things like that.
Then you can actually start to move much, much faster and communication becomes much, much, much less painful.
So the
tactic here is to help your team s kind of build a mental model.
of everyone in the company that matters.
So that
It's like the way you put it almost is when they're emailing them or asking for something they w they already know how they're gonna respond.
Is there is there an example you could share of something like this of just like something a person at Woop
of how they think. I don't know, maybe you could keep it anonymous just to make this little real of the kind of mental model
You might want to build around someone.
So our CEO Will is uh
Somebody who obsesses over pixels.
In a way that
Um
is is you know challenging to get things through design review.
But
I think result in a
Product that is
A thousand times better than it would be if
Uh he were accepting of
You know, small
Uh excuses here and there for oh well this you know
We had to cut scope here. We couldn't quite do what they wanted here. Like he sets a high bar and he holds it.
Um and he doesn't compromise.
And
I think this can sometimes get misconstrued.
And I think a lot of people might think that.
He just wants like maximal scope on everything.
Um
And I think that is a misunderstanding of what he cares about.
Uh, we often get feedback from him that's like
You know, this doesn't this doesn't feel like the future.
And everything that we're building needs to feel like the future.
A lot of people hear that and they're kind of like, Oh gosh, like
w you know, we're never gonna get this thing done on time. Like we can't make
Any sort of sacrifices to scope or anything like that.
But when I hear that, like what I hear is more that
With we have this AI coach in the product, we have all this amazing data in the product. Uh you know, we're tracking every single one of your heartbeats and we're pulling out all this other data.
And
We have every like every screen is a moment to show that to people in a way that feels like something that has never existed before.
And there are small ways to do that, right? It's like how you pull in if you're explaining a concept like uh VO2 max, which is the you know a measure of your cardiovascular health.
You can explain that to people with static content.
Or you can explain that to people by bringing their data.
Into
You know, the the method of explanation that you're using, you can make it really conversational because you're using this AI coach. You can make it feel more like.
You're talking to a person.
And a person who, by the way, has
all the data about you, which doesn't exist today. Like your doctor doesn't have that, your coach doesn't have that.
And that's not like oh gosh, we've got to blow up the scope on this thing and make it a hundred X as big.
But it's finding these like little touches to say, like, wow, that was really magical. That was really thoughtful.
And this this feels like the future. This feels like
I'm very conscious of the fact that
This product
knows so much about me and is able to sort of sort out the the um signal from the noise on that.
In these really small and elegant ways.
And so
For something like that, like I would get that feedback in design review, or I'd hear that in a design review, and maybe one of my PMs would be in that design review.
Um, and so I bring that to the team. And I hear things like that in a few different design reviews.
So I bring those back to the team. I'm like, I've noticed that recently we are consistently getting this type of feedback.
Uh, here's why I think it's really important to will.
Uh because I think he's really focused on building you know the the health company of the future.
And
I don't want you all to think that this just means
Like we have to just throw AI at everything and we have to just throw like maximum scope at everything.
I think the key is understanding like
On the matrix of
Uh cost.
And effort.
For uh impact. Like what are those
High impact, but low cost ways.
That we can just find and sprinkle through the experience.
Um and and really try to make that magical.
Uh so I'm connecting the dots for my team, right? I'm saying you weren't in all these meetings, but I saw it.
Here's what I heard.
Here's my interpretation of what I heard, um, and here's how I'm thinking about how this other person thinks about it.
And so as a result, like
Here are some things that I think we can do in
Across our product going forward.
Essentially these are
Principles or values or tenants per person of what matters to them. Exactly. So for Nick it's
This needs to feel like we're living in the future. It can't just be like another
uh heartbeat tracking app.
This is so cool.
And there's so many ch trickle down benefit.
To this.
One is people feel like
they're aware of what's happening. That's one of the most common, I think
piece of feedback people have at big companies like I don't know what's happening and so there's so much visibility to all the secretive stuff happening in the meetings like I don't know.
what people are deciding my fates and all these discussions. So I think just even knowing that you're sharing all this is so powerful.
Well and on that note, like
When I approach these conversations, I always try to think of them as um
Even if I don't agree with the feedback, if I don't agree with the decision, like
What is the insight that I'm missing?
Like how am I wrong about this?
in ways like what would be true for this other person to be right?
And I'll go through that thought exercise and I might not
get to the other side and agree with it. I might still
You know, think I'm right or whatever.
But oftentimes
It forcing myself to think that way.
forces me to think about how this other person thinks it. And I if I do that enough, I will be like, Oh, this makes sense. I think this makes sense if.
I think this makes sense if and oh maybe this other thing is true.
And I think when I s when I hear the people, the people who are like, I don't know what's going on with this company, like
I think they do the opposite. Like I think they look for reasons to disagree.
And they look for holes to poke.
In
Well, this decision doesn't make any sense because I came up with something that might be wrong about it.
And I think that's another thing, by the way, in terms of just sort of like
Helping your team have the emotional maturity to exist and thrive in an organization.
Is is helping them think that way, like helping them understand.
You have a point of view. Your point of view is important. Um
But on some level like
You do kind of have to have respect for these other points of view.
And have the humility to think that like maybe they they're on to something that you're not on to.
And it's amazing how much you can like learn and into it.
without having to have all the facts just by doing that. If you're like
Well, this person's behavior makes sense in a situation where X, Y, and Z is happening.
Oftentimes you will find that X, Y, and Z is happening.
I'm glad you went there. I wanted to actually follow this thread, which is kind of a different direction, but I think a lot of people are
Always struggling with this as a leader.
when your leader disagreed uh does says something that you completely disagree with.
But you still need to represent that as like
Here's the thing we're doing. But you don't wanna be like, Oh, just because Nick said so, you know,'cause you lose power as a leader.
Do you have any just is there like something you've learned about how to do that well when your leader
Tells you to do something you disagree with.
And you still need it.
Get your team to do it.
First I I do try to go through like
the
The what if I'm wrong exercise.
Uh, I think a lot of people just sort of like expect that if you ask somebody of as a
open ended question like why are we doing this?
You're gonna get
a straightforward answer. And oftentimes the answer is not straightforward for various reasons. Like maybe there's confidentiality reasons.
Uh, maybe there's just like
You know, s the somebody is acting on a hunch.
But that hunch is informed by
Years or decades of reps of developing judgment. And like they're probably really on to something. And it's not just like this kind of arbitrary gut feeling.
But whatever it is, like
I really try to get to the bottom of
Let me let me really make sure that I have done my best to understand this person's point of view.
Um, and I have some sort of tools for doing that, which I can also talk about.
But if I've done that and I still disagree.
I'm like
relatively candid about that.
But can't it in a way where like it's still respectful. Like I think
what you want to avoid is a situation where as a manager you're like
Uh this you know, I have no control, this sucks.
This decision is so stupid, but like
That's a job, so we have to do it. Like
Obviously that's not gonna
you know, set your team up for success or make anybody happy about it. But you do you do hear that. You do see that happening.
And so I think what I try to do in those situations is separate out like
my opinion from it, from the like, well, what is the insight that makes it make sense to this person?
And explain their rationale, even if I'm comfortable saying like
You know, I don't necessarily think
Like this isn't how I would do it, or uh
I don't even really agree with how they're thinking about it.
But from their point of view, from their perspective.
uh their professional experience, whatever it is.
I could see how this makes sense.
And like
They might be right.
I don't think they're right, but they might be.
Let's find out. Like we're not gonna find out.
If we are all squabbling about
whether this is a good idea the whole time. Like the only way we're gonna find out.
is if we give it the best shot that we have and try to do it.
And if we're wrong, like that happens sometimes and we try again.
I like that this comes back to your mental model orientation of here's their mental model, here's what their experience has been like, here's how they see the world, the trends.
And then this is why they think.
The way they think.
And so instead of
Encouraging.
your team or yourself even to be like, No, no, you're wrong here. It's more
Okay, here's their data set.
Let's try this and this will inform that data set and maybe change their mind.
Yeah,'cause I think in product, like I like to joke there's no right answers, right? You're just it there's only wrong answers and you're just trying to
Execute well on like the least wrong answer that's available to you.
Uh and so I think it is like
You know, the sort of
Reasonable people can disagree about this of it all.
Uh
You know, like this is what I think and this is how I approach it.
I think this is what they think.
And I think this is why they would approach it this way.
And again, like
The only chance we have of succeeding.
Is not
being torn apart on that.
And so
At the end of the day, like if it's not a like a
obviously terrible answer, and sometimes even if it is an obviously terrible answer.
You're still more likely to succeed if you just sort of like
sort of reorient yourself around a world where it's not a terrible answer and then just try to will that into existence. You said that you have some tools to help you understand someone's point of view. I can't help but ask more about that.
I
Talk about what I like to call the magic questions.
But the thing about magic questions is they're not actually questions, they're statements.
And they end with do you agree or is that right?
And so
I have found this as like the most helpful way for kind of trying to understand a person's uh mental model.
Is to
Just like put
And see when they say no to and what they say yes to.
And then if you can get them to explain great. And if they're good communicators, they often can.
Um, but if they're not, like you don't have to let that stop you.
And so
I mean, I I'll I'll do this even just as an example, uh, in a non leadership context with
If I'm working with like legal teams or compliance teams or things like that.
They're often working from a a literal set of rules, right? There are laws, there are regulations.
Um, and you are trying to understand like
What
I you know, if we were to take this path, would that be okay? Would that not be okay?
And sometimes that's that's not
Straightforward.
Um sometimes like
it there's regulatory areas that are um
You know, up to interpretation.
And so when I first started working in like a regulated space.
I would find this kind of frustrating and confusing because I would say
Can you just like can you just like give me the the rule so I can understand what's right and what's left of it?
And they'd be like, Oh, well, it depends, defense, defense.
And so I learned that if I kind of flip that and approach that like
Well, you know, what if we did X, Y, and Z? Like what if this is what it looked like? What if this is what the copy said.
Would that be okay?
No?
Yes.
If no, why?
If yes, why?
And so I'm sort of teasing out the mental model rather than asking them to explain it to me.
And this is what I tell my team all the time to do this to me. Like
When they come to me and they say, Well, what do you think I should do?
Or um, you know, what could I have done differently?
I'll say like
Rephrase that as
Tell me what you think you could have done differently.
And then ask me if I agree.
And when I do this
I think it ha it has a few benefits. One
it helps them kind of calibrate their judgment over time. So they're they're actually forcing themselves to make this assertion.
And then they're kind of calibrating how
close that was to like how I would think about it.
Um, which will get you much faster, much further than just asking open ended questions and getting the answer.
And then the second part of it is um
don't become reliant on me for answering these questions. I think that's kind of a trap that a lot of managers fall into.
Is you
People come to you with questions, you want to help them, you answer the question, and then you find that they come to you with all their questions and you're kind of like
Yeah, you gotta solve some of these on your own.
So again, I think like the magic questions to me, is that right?
Do you agree?
And any time you find yourself like
Tempted to ask an open ended question.
To somebody whose brain you're trying to understand.
stop yourself and say, like let me just say that let me say as a statement what I think.
And then try to calibrate based on their reaction.
And like I think that's the fastest way to understand how another person thinks.
There it makes me think about a lot of people.
Like it sound it could come across as it's like a weird manipulative way of asking someone stuff. But it turns out that
Like, we're not good at really knowing what we think or know a lot of times. And you need someone almost to interview you in a really
effective way to get out all this knowledge.
And this is just a really simple way of getting that idea.
Uh, when I talk about this, I g I get that reaction a lot where people are like, Well, doesn't it feel coercive?
And I'm like, Well, you gotta go in pure of heart. Like you've gotta go in open to being wrong and even expecting to be wrong.
And you have to make that clear to them, right? Like if you're coming in and you're like
Here's what I think. Like you agree, you you agree like
Of course you're on baby, that's what you want.
me you might get the answer, you want you might get a yes. If your goal to get to yes
That's not what I'm that's not what I'm talking about.
If your goal is to understand
And you are coming from like a help me understand how I'm wrong, help me understand what I'm getting wrong here.
Um and approach it with that sort of like curiosity and humility.
Um, and make sure that you're like caring yourself and presenting yourself to this person in a way that that that shows that, that you're not coming in like hostile or forceful or something.
Um yeah,'cause it it there are absolutely circumstances where you're doing that and you're gonna get bad intel because
You're making the person uncomfortable, so they're gonna lie to you.
But that's like a
I think a whole set of interpersonal skills that we probably don't have time to talk about today.
I wanted to come back to you said this uh f interesting insight about your CO that he wanted to build something that
uh was felt like the future uh
I just wanted to share there's a story that has always stuck with me at Airbnb.
there is a a big launch coming up and there's a designer
Sitting at late in the office trying to re
Update the website to include this new product. It was a launch of Airbnb neighborhoods like
I don't know, ten years ago.
And he's and she was just like, Hey Joe and this is Joe Gebd was walking around the office and she's like, Hey Joe, what do you think I should
Uh, what do you want the website to be? What do you want it to look like? What should we
Try to
And it was gonna launch in two days. He's like
Build something the internet has never seen before.
And now this makes me like it's interesting because when I th always think about that story and tell that story, it's like this is a crazy ask.
And now
As you
share an approach for how to handle something like that. It really changes my perspective.
Okay, what's Joe's
world view. Why why is that the way he saw?
the world and why we needed to build a site like that.
Which I I could start thinking about, but that's a really interesting way to just like handle things that sound absurd.
And out of nowhere.
I agree so much. I uh
Proud former English major, and so I'm a huge proponent of
reading fiction and and reading in general and um
I I feel like that's where so much of this comes from for me. It's just like a curiosity for like in in what world does this make sense for this person?
Uh
And it's so easy to look at another person's behaviors and another person's actions and what they say and just be like
That doesn't make any sense.
And I just I find that
I don't know, like your relationships become so much richer.
Even just in a work context, like when you approach it with that.
Like what what is the world of this person where the thing that they're saying makes sense?
And I like I feel like in my life
Honestly, like a lot of my frustration has come from being frustrated with other people.
And so this is something that I I've had to learn over time because
When I come home from work and I'm just like oh this person said this and it didn't make any sense and this person's totally out to lunch and leadership doesn't know what's going on, like
All I was doing was making myself miserable.
Uh and actually worse than that, I was making myself miserable and I was making myself pretty useless to the company.
And so
I would get frustrated because I was like
You know, now nobody appreciates my perfect, unique, beautiful insight.
Um, and all these other people have no unique, beautiful, perfect, concise just wrong opinions.
And so I feel like that's been like a big area of growth for me, honestly, is
uh like learning to approach people that way. It's not just like
Oh, this is a nice thing to do, but I think it it like genuinely makes me a happier person.
Uh
And yeah, I think I think a lot of it comes from reading fiction.
Hm. I love that we're just unpacking the onion of the power of this very specific habit of just
Helping you.
learn the mental model of the people and around you. And I don't think this is just making me sound like a crazy person. No, there's so much power to this. Like it's a it's as you talk, I'm like wow, there's so much value here. Cause not only is it
You talk about how this is the source of a lot of burnout for a lot of people.
Where they're just so frustrated. The CO or the chief product officer designer is just like, uh, I hate this. Where are they just asking all these ridiculous things, keeping the bar way too high? It's just nothing's ever good enough.
But not only does it help you
feel better about their ask.
because you can understand where they're coming from.
It also helps to be more effective in helping them change their mind potentially.
And see a different perspective.
Because now you see the
data that informs their perspective and you could help
Adjust that or
Or kinda poke at it, like, hey, are you sure this is true? Are you sure like
I don't know.
your competitor and this is how they see it. Maybe it's not. Let's let's look into that a little deeper.
Yeah, it's really interesting. I uh
I and my last company, when I started reporting to the CEO
Um they
found various for me to work with.
And one of them was the former chief product officer at
Coinbase who's gone to Fountain Bridge, which is
She cut apart by stripe for a ton of money.
And
One thing that he said to me that really stuck with me is
When you're reporting to the CEO and like if as a chief product officer
The big mistake that people make is they think that the game is all about getting what is inside their head.
And like influencing
The CEO influencing the people around them.
To make it so.
And if you go into the role trying to do that, you're gonna fail.
Because actually like what your job is to do
Із тон.
what the CEO's vision is.
And
Like what they care about again, sort of how they think about things.
Um and figure out how to operationalize that.
In a way that results in the best possible
manifestation of it in the form of product.
And
That was just such a like radically different way from what I ever thought my job was.
Uh, again to go back to sort of the fish fiction example, like
You know, you kind of you kinda come up thinking like you're the protagonist, and you can be the protagonist in your life. You can be the protagonist in the story of your family.
But in the in the story of your
work like of a company.
Uh
Like
You are probably not the protagonist.
And
As much as it
You know, it can feel kind of weird to say that.
I
I genuinely think like
some of the best advice I've got in my life in terms of things that have just not only transformed how I see the world and how I act in it.
But just like my own sense of
Happiness?
It's like you're not special.
And it's like
I used to spend so much time and energy just being like
Oh like
People aren't people don't see it my way, and I have to convince them.
And when you're in an organization, like it's a it's an ecosystem, right? Like it's a it's an organization full of people who are all trying to work together to get a thing done.
And if every single one of those people is operating from their own like
protagonist viewpoint of
This is how I actually see the world. This is what I think we're here to do.
And I need to convince everyone around me at all times, like it becomes extremely inefficient, it becomes extremely painful.
Because just
Everyone's just fighting all the time.
And so in some ways, like it it feels like you're kind of uh like if it sounds almost defeatist. Like I'm always worried about the sounding, like I'm just like, yeah, just do whatever the boss says.
Um
And that's not how I feel at all. Like I think it's incredibly important to bring your skills and your talents and your perspective.
to the job you have, um, and and really the your taste and your craft and all of these things.
Um, but I do think this idea of like
Understanding how to build a shared mental model of everyone together.
That definitionally cannot be defined by your own narrow perspective.
Um
Actually just makes work a lot better for everybody.
So then
A lot of people, like you said, I love that you went there. It's just like if you're
'Cause it could sound like okay, your job is just to execute what the CO tells you.
There's no value to your
insights and perspectives and you're just get out of the way. You're just this
Get everyone to do the thing this year wants.
Where do you I guess in your experience or just advice on
Where's the fulfillment for you then as a CPO or example or a director of product?
Where
You know.
It's not that fun just to be there executing a CO's vision and not have any input.
When I think like
There's there's so many decisions all the way down.
And there's so many like
micro places where you can you can zig where others would have zagged.
And I think I personally like a lot of where my fulfillment comes from is from feeling like
If somebody else were in this job, it would be done differently.
And like something about the product is different because I was the one who worked on it because I was in the job.
And that that comes from like my unique perspective.
My unique point of view the
experiences I've had in the past, like my various influences.
Um
And I think it's trying to like
figure out the right level for it.
So that you're not you're you're not pushing against an immovable force.
Um
You know, it's al it's almost like if you're playing Jenga and you're sort of trying to feel around to find like
Okay, well where are the pieces that can move?
And when you know
how somebody else thinks, A, like you can find that
There are immovable forces. Those are not the battles worth fighting.
But there are also areas where maybe they don't know as much.
And there's also areas where maybe like
They're actually kinda scared because they don't know as much.
And maybe that's an area where you have an interesting point of view.
And so you can step into that role and be tremendously
valuable and and have been tremendously influential.
But you can only do that if you have a good like
uh frame for kind of what your what the what the model is and where are the things where it's like
Okay, we are operating on a person's insight here that is
It is use itself extremely unique and extremely valuable, and it is the reason this company even exists in the first place.
But that I mean there's
millions of decisions have to get made, you know what I mean?
Uh, and there's millions of different places that that you can
You can put yourself.
Um, and so I think it's just like kind of constantly feeling out for like
were the places that I'm really spiky.
Were the things that I think I do really well.
Uh where are the gaps?
And again, you can only you can only find those if you're engaging in really good faith.
And engaging earnestly in in like
Really understanding how other people think.
There's two really interesting thoughts that I have as you're talking that I think will even further crystallize what you're saying. One is that
You're just saying this is the way the world works. It makes me think about Jeffrey Pfeffer. He was a guest on this podcast. He teaches this class at Stanford Business School about
How to how to gain power in the world. It's like
And the rules of power.
And uh
He talks about, you know, it's like it and it's like all these ways to
to influence and win and achieve and gain status and all these things. And he's like, you know, this part doesn't this doesn't sound fun and
And great, but I talk about here's the way the world works and is not the way you wish it would would be.
And what you're describing is
The way a company works is the CO is in charge, there. And your job is to, you know, they're the boss.
And
The sooner you understand there
Vision trumps your vision.
The easier everything gets.
Like you're not there to tell the CO here's what we should be building, right? Their job is
It's
own the vision of the business and the company.
Yeah, I think that's true.
And if you don't if you disagree with it, like you probably shouldn't be working at that company.
Yeah.
The other pieces th it's just the vision. Like here's the vision of the future of where we are heading.
If we win, here's what will be true and the world will look like.
But there's so much more.
that you need to figure out that is
To achieve that vision. And that's basically the role of this of the CPO and director of product, all those sorts of people. Everyone at the company how you said it there was so is so right on because it is like
The vision is is
In many ways, I mean in some ways it's execution based, but in in many ways it's
A vision of what the world is going to look like.
In five years, in ten years.
And so
In in some ways I would say like your your job is
If you can understand that and you can understand
Here's what this person thinks the world is gonna look like.
Uh
Assuming all that is true.
What are the things that I can do to maximize the chances of that?
And like becoming the actual future.
And then also what does that mean for a product? Like what does that mean for
Uh
If if
It has to be true that
Like, you know, take Woop for example, if
Uh if there's a vision of the future where
You have all of your health data in one place.
And were able to
Detect health
Issues before you even know you have them.
And we're able to do really hyper personalized coaching, uh, to help you understand like
how your behaviors today are impacting
how healthy are gonna be in in decades.
Uh, what does that mean for what WOP needs to be today?
And what does that mean for
How it needs to evolve in the next couple years.
In order to both make that a reality, but also like
win in that world.
Um and I do think that's exactly where the like the people in the rank and file can be.
Tremendously influential.
It's that level of like
I'm gonna fight with you about how the world's gonna work in five years where I think you're you're just fighting a losing battle.
And if you don't like the vision, you could leave, right? It's like
Or change try to change it. Like those are two options. And I think your to your point about pushing back, because you asked about this, like
I again I I I never want it to sound like I'm just like defeat us, like just accept it. Like
I'm a very opinionated person.
Uh like I go to the mat for things that I think are true.
And so I've I
You know, I teach my team like
You have to be really good at forming arguments.
And that can be that can show up in different ways. Like some people are really good at doing that with data.
Some people are really good at doing that with, you know, sort of the quol and the quant and moving it together. Um
But you have to be able to advocate for what you think is true in the most compelling way possible.
And
You have an obligation to do it.
And if you have done it and you've done it well.
And it didn't work.
That's when it's time to say, Well, maybe there's something here that
You know, that I wasn't seeing previously.
Um and that's where I think the you know it's
It's time to have some humility around it.
But this, you know, there's it's a it's a journey. You don't you don't start from like, well, I got I got nothing to say here.
Um, so I think it's you know, knowing where you are on that journey is important too.
This reminds me there's a PM leader at Airbnb who
Ended up leading a new initiative.
And they ended up doing a bunch of stupid stuff. And he's like
I just I'm realizing that it's me that needs to be pushing back on stuff now that I'm in charge of this product team.
Uh I'm the person that needs to
convince the CO this is a bad idea. And i I I I'm just realizing that after
Doing a bunch of stuff that was stupid.
And you do like you will see that idea that you do have an obligation to try to convince them that it's a bad idea.
And you're gonna be right sometimes and you're not gonna be right.
Every time?
And I think that like that's why it's so hard to talk about these things in absolutes, because like
Sometimes you're right and sometimes you're not right.
And it is important to get really good at knowing the difference and knowing uh where you go from there.
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I want to move on to another skill you really get up, but first of all, something I noted that I wanted to touch on real quick. You mentioned that Woop now does VO2 max, and that's not a promotion for Woo, but that's so cool. That's like a huge
thing to track that this is like the thing that Peter T and all these guys are always saying this is the thing you want to track.
to understand your health and progress as your VOT Max. It's like your blood oxygen level. I don't know exactly what it is. But uh
But that's cool, then you woo once you do that.
There's so much cool stuff we're doing right now. I'm like
I don't know if I want to get into it all right now, but I can. We'll get back to it. We'll get back to it. Okay, cool.
Yeah. Um okay, so another
habit slash skill that you are really good at that I've heard from folks.
is and you've mentioned this a couple of times, is just building
habits, helping your team build good habits.
And
coming back to the CBT stuff, just like behavior loops and things like that.
Talk about just what that is, why that's important, what you help your team learn there.
Yeah, I'm kind of obsessed with
habit formation and reward loops and
behavior change and all these things. And um
When I think about
trying to change behavior on your team or just trying to like
Encourage your team to do more of the behaviors that you believe are associated with success.
I think a lot of people
Think about it like more of like an education model where it's like
You know, you teach the thing, you assess the thing, and then you there's like some accountability around the thing.
And um I think if you if you think about it more in the
Context of
behavioral psychology, it actually works a lot better.
And so I'll give you an example. Um
I've
Like many leaders have been trying to uh
Think about how to drive.
AI adoption, AI upskilling on my team.
And what that can look like.
And uh when I talk to people about this outside of the company, I'm always surprised because they're like, Well how you know.
How do you measure it and how do you enforce it and
Uh.
I don't
I don't really think about any of that stuff. Like
I'm thinking about like how am I creating habits around using this?
And
For me, there's a couple things there. So it's uh consistency.
Um
How are you getting someone doing something every single day?
And to do that, like it has to start small. It has to start super easy. You have to give them things that take
No more than a minute or two to do.
Um, and I actually I have like um
Thirty days of GPT, I call it.
Of like a list of thirty things to do one every single day.
That I don't know anyone who has gone through this and like not come out the other side feeling a hundred times more confident in their skills and actually using it every day as a habit.
Um, because it's built like as a habit formation tool and not an education tool.
Um, this is using a specific GPT built or building their own GPT or what's the habit there? Uh the habit is using chat GPT or Claude or any of the GPT. All the tools to get their work done. Um in just sort of like a kind of generic get work done way.
Um
And so
I have this little tool. If you sign up for my newsletter, I'll send it to you.
Uh what's the Usletter while you as you mentioned that?
Thanks for asking. It is hills.substack.com. H I L S dot substack.com.
Sweet.
But basically it's one little thing you can do every single day.
And
The key with this is again consistency. So you need to get people doing this thing every day.
Uh reducing friction.
I think a mistake a lot of people make when they start thinking about how to drive adoption is they're like, Oh, we have to show people how to do their work with these tools.
But I'm like
Well, work is hard.
And
If you are on a deadline for something, you've got to get something done.
The last thing that you ever want is more friction associated with getting it done. Like it is so annoying.
when you're trying to get a thing done and like
your tools are being changed on you and you don't know how the thing works and like
You know, the hotkeys are all different or whatever.
Um and so I actually think like using it in uh like
situations that have nothing to do with your work.
Um
Are way easier because you're removing all of that friction of like, oh wait, I gotta go think about all right, what's a project that I'm working on?
Oh, I put this into Chat GPT and I like didn't really get a good answer. And now I'm frustrated because this thing's taking longer than I need it to take or whatever.
Um
And so
You know, I start with things that are just like fun simple use cases.
Uh like, you know, it might be
We're coming up with
times to take a vacation or places to go on vacation. Or it might be like
Uploading your calendar into ChatGBT and asking it for
Ideas for
talking points for the meetings or like things where the person doesn't have to think.
Because it's all just spelled out.
And things where like there's no
There's no like external work pressure.
that you have to apply this to that's gonna make it like an unpleasant experience.
So consistency, reduce friction, and then most importantly, designing reward loops.
And this is something that
When I'm talking to people about designing for behavior change.
The number one thing I always tell them is you are not thinking enough about
The reward loop.
And the reward loop needs to be powerful, it needs to be immediate, and it needs to be emotional.
So that when this person does the thing that you want them to do
They feel like a million bucks.
And so when I think about any kind of habit I'm trying to to build on my team
That's something that I'm I'm always thinking about is like
How can I make sure that when a person does this
They feel really great.
And part of why I like custom GPTs as a tool for helping people learn to use LLMs. And I talk about this on the podcast I did with Claire on how I AI.
Is because it
If you put in the prompt, you as the person building the custom GPT.
You write the prompt, you put it in.
You design it such that somebody can
Upload a specific
Uh document.
And then they can get a specific output, like feedback on that document.
Um or you know, maybe something more fun than feedback.
Uh an improved written version of that document?
They get the like the joy of like ooh this helped me, this was cool.
without any of the like despair of oh I'm not very good at prompting and this didn't really work and I'm frustrated.
And so I'm just I just always think about that in general, like if I'm trying to build any kind of hat on my team.
It's less about like the accountability of like how I'm enforcing this.
And more about like how I make it so rewarding for people to do it that that they they do it naturally.
I'm gonna I wrote down notes as you were talking. So kind of the four parts of habits. And I wanna I'm gonna ask you for an example to help people see how this actually works in real life. But
Basically to help
People build an actual habit, the three steps are consistent, the three things you want to focus on consistency, friction, and reward loop.
And within a reward loop.
You want it to be powerful, immediate, and emotional.
What
Is an example of this. Yeah, I can give some actually examples of like
how we do this in product, if that would be interesting. Absolutely. Um, because I think there's something Woop is really good at.
So
I think one of the most interesting kind of anti reward loops
On Whoop is around alcohol.
Um, Whoop has this recovery.
system. Uh you get a recovery score every morning.

how recovered you are and how ready you are to take on the day.
And
If you drink and you're on woop
You will very quickly learn.
that if you d any time you drink you get a red recovery.
And
It's so interesting because
It's not like people who were drinking.
weren't getting hangovers before or like they weren't like
They they knew that it was disrupting their sleep. Like none of this is news for people.
But there's something about seeing that like red score.
That just feels like
It just feels bad. It has like this really profound emotional impact on people.
And when you see the green score, it it feels great. It's like oh I'm like
I'm doing something well. Like I'm taking care of myself. I'm a healthy person.
And you I hear this when I talk to members all the time and I hear people say
Uh it I've been, you know, I've had problems with rent drinking for years, and it wasn't until I got on Whoop that I was really able to get a handle on my drinking.
And I'm always again kind of like amazed by this because I'm like
You had all the information you needed before.
But there's something about the like you wake up and you get that red score.
That's just like
It it manages to override like whatever was driving people to do it in the first place.
And then I think continuing to like have that data where you can look back at your data and see, Oh, that was the red day. That was the day that I I did this thing.
Um
And it's something that we've actually been trying to uh
You know, find ways to do this in a longer term way.
Because when you have these short reward loops, it it's easier where it's like I did a thing and then I immediately either got a reward.
Green recovery.
Or got an anti reward, red recovery, and that is changing my behavior as a result.
And we have this new feature health span that uh we just launched with our new hardware.
And basically what it's trying to do is help you have this reward loop between your
behaviours and activities that you're doing today.
And what that means for
How healthy you're going to be in.
you know, twenty, thirty, forty years.
And so we have something similar where we have this uh we call it the amoeba.
Um, it has your Whoop age in it. It's like it has
colours and sort of kinda moves around.
And that changes based on how your behaviors and your activities change every single day.
And the colors change when you're doing better and when you're doing worse. Uh, and you can kind of see it all broken down.
How you sleep.
Your VO two max.
The consistency of your sleep.
uh how much time you're spending in different heart rate zones, how much time you're spending strength training, things like that.
Um, and we found that again, it's just this incredibly powerful reward loop.
Because we're taking something that
historically has been really, really hard, which is like
When I make healthy changes today, not only do I not see the results of those for decades, but
the the short term reward loop of those af often feels pretty bad because change is hard and it feels bad before it feels good.
And trying to like build that reward loop.
That is is more rewarding for people to see.
those numbers change and to see those colors change.
Um, so that they're actually able to make those changes and see that progress and feel really good about it.
I love that you're using all these uh habit building
tactics that folks have been using historically to get you to check your Instagram likes and your
Facebook posts, uh, for actual good.
For helping people live longer and happier.
Uh that makes me very happy.
Is there an example of doing this sort of thing with your team of helping them build and you talk about AI, like learning to use CloudShat GPT?
I think I mean really I I think a lot of it is just shouting people out, right? Like
When uh
When somebody is doing
The like
Using AI to solve a problem that they wouldn't have used AI before, like
Give them a shout out in the team meeting, let them demo that. Like again, make them feel like a million bucks for doing the thing.
And people respond to that, like people will see.
mean maybe it's because I work at Whoop and we're all obsessed with reward loops, so we're all like
Or here's your reward. No, exactly. But no, like like people see that and people respond to it. Um
I think you know, another example is like something that
I think about a lot and is relevant to our conversation about um just like
How you
Build teams that can do hard things.
Is
Ah, how you encourage people to take care of themselves outside of work.
And
It's something that like I'm always trying to model for my team and make it really visible the ways that I'm doing this.
Um, and sort of like having my hobbies and my other various things.
And as a result, I also try to reward like have these reward loops when I see people on my team doing the same thing.
Because I think people bosses often
inadvertently create reward loops for like, oh this person, you know, they had to stay until two o'clock to get it done, but they got it done.
And when you create those reward loops, that's the behavior that people
Start mimicking.
And so I you know, I I try to do the opposite. Like I try to
Uh
find ways that I I really am impressed with my team and the ways that they take care of themselves outside of work because I I think that makes them
better at their jobs, frankly, and just happier humans.
And so like there's a PM on my team, Emily, who uh teaches at
handlebar she's a fitness instructor in her spare time.
And so whenever we have like a long meeting
I'll be like, Oh, Emily, why don't you like lead stretches uh to get like the energy level in the room up? Just like you know nothing serious just for a minute.
Um, before we start the meeting. And it's kind of fun. Everyone has a laugh about it. Like Emily's doing her thing, and I'll be like,
You know, everyone everyone come check out Emily at uh Handelbar in Charles Town this Saturday at ten AM.
And by the way, like you all out there in the
Podcast world should
Should do that if you're in the Boston area. She's great.
Uh shout out to Emily.
But it's things like that. Like it's just it's just finding these small ways to like
'Cause people are already laughing, people are already smiling, we're doing this silly thing.
Everyone's in a good mood and I'm like boom perfect time to give someone a shout out.
And make them feel like a million bucks for doing something that in many cases they might think like, Oh, am I allowed to have this other job outside work? Like, is this okay?
And so yeah, you gotta you gotta like proactively build those reward loops.
I love the uh reward loop of Emily getting the shout out right now. This is so meta.
She's gonna have a full class coming up in Boston.
Is there anything else along those lines? Because I thought was really interesting.
Also, people like, you know, I know managers already kinda do this just like, you know, promoting, but so I think the core lesson here is like
Focus on things you want to encourage more.
Less so.
Hey, they worked the weekend, they got it done. So awesome. Thank you for doing that.
Uh you know, you're saying that's almost an anti pattern'cause you don't necessarily want that as a habit.
So it's more like shift your reward.
Announcements to things you actually
intentionally want to create a Yeah, just just be really, really thoughtful about it. Okay, so let's come back to the taking care of yourself because this is something else that came up. Almost everyone mentioned this. So you're doing a good job with this of finding time to take care of yourself and modeling that for other people.
Uh specifically, a lot of people commented on how you create
You create space for creativity.
And I think to a lot of people
Lot of PM specially, it's just like I have no time for anything. I just have meetings back to back all day.
I barely have time to go to the bathroom or eat.
And uh
I'm curious to hear just how you do this. How do you create space in your day for creative work and deep work and
Thinking outside of the meeting.
Yeah, it's funny. I'm glad to hear people think I'm gonna do this because I'm like
I'm terrible at like organizing events. Like my team's always like, Oh, we should do like a fun event. And I'm like, Yeah, that's a great idea. And then
I I don't organize it. So I I like to think I do this in other ways. Uh and I do think one of them is just like
In
modelling how to carve out space for things. And a couple things. I think there's the creativity
Which for me is like probably more outside of work.
And for me, it's creativity, but again, it's like a big part of me as a manager. What I think I can help people with is
Back to the point of behavioral activation, like
Understanding what the things are
That a person needs to be happy to be their best self to be a high functioning person.
And that is the
depends on their values. It depends on a lot of things about them. So
You know, for Emily it's fitness, it's teaching, it's these things.
Uh for me it's having like my uh my crafts that I do, my illustration, my writing, my reading, all of these sorts of things.
Um
I think that that's the first step is just as a leader, like understanding what those are for people on your team.
And then as I said
modeling it. Like I
I try to always
Tell people.
Like
Here here's how I'm doing these things. Like I talk about them so it's really normalized because I think
I mean a lot of PMs are like, Oh my gosh, I'm so busy, I have no time and maybe meetings all day, but like
That's a little bit self inflicted, I think. Like you at some point, like you have to be the one responsible for getting yourself out of the weeds.
Um
And it's hard to do, but it it is it's doable.
Um
And so I think just like showing people that it's possible, like showing people that you you can do these things. And I I talk about them and I bring them to lessons. I have like a a book club that I sometimes require at work and then I
Saying maybe I don't need to require this anymore.
Um
But like like ways to just make it really visible, make people make sure people know that I'm doing it.
And then ask them about it. And
You know, if I in my one on ones when I'm checking in with people, I'm asking them like
What what do you do for joy? Like are you doing something every single day that's bringing you joy in your life?
And if they say no, I'm like, that's a problem. Like, how what are we gonna do about that?
And like what o do we even know what those things are?
'Cause I think a lot of people don't.
And
Like a lot of people it's great. Like they're like, Oh, I need to be getting X number of hours of exercise, X hours of sleep.
Uh like I know I need to eat lunch right at twelve or else I turn into a pumpkin.
Um, and if if it's somebody who like knows what all those things are and you're just there to kind of help them carve out time.
That's one thing, but I think in a lot of times like people don't even know. And then and then you kind of behavioral activation them where you're like, all right, well.
Why don't you try some things and get back to me and like let me know what what seemed to work, what seemed to make a difference.
But I do think so much of it is like a permission structure.
Because people feel the pressure to be like, Oh, I'm so busy, I'm so busy, I'm meetings all day. I can't
I can't decline these meetings. I can't not do these things.
And so in many ways I think just modeling it gives them the permission structure to
To start to take back her life.
I could see why people love working for you.
being asked in your one on one. Are you have you done anything today that brings you joy? And if you haven't, that's a problem.
Wow. It's important, you know? It's like that's what life's all about. Like why are we here if it's just to toil and be miserable?
And also like you know, they will be better people at work and they will do better work. I think that's like tell them correct me if I'm wrong, but it feels like that's an element of this.
Well and it you know, it's so funny'cause so much of this stuff it's like obvious when you apply it to an athletic.
Context?
Uh, and obviously it will be you know I not talked about the like recovery score. Um this concept of like athletes need to recover.
is very obvious. Like no one, I think, would argue with that.
Uh, if you're just pushing yourself at a hundred percent of your physical capacity all the time, like
Not only are you gonna burn out, but like you're literally going to suffer performance decline.
Um
And
You know, in the same way like
I think in the atletic world there's so much more just
Acceptance of
Uh
L I didn't even want to say limits, but just like
You have to take the time to do the things you need to be your best, and that's not just
running into the wall all day.
Um, and I think we forget that at work, but I think I mean the analog is a hundred percent there.
I also think about this with um
In terms of being able to have
creative breakthroughs of any kind.
It's just so important to have active rest. It's so important to have heads down time. Like this stuff is all very well documented. We know it all.
Um, but we just come up with excuses to like
not give it to ourselves. I think it's it's kind of self sabotage at a certain point.
I definitely come up with excuses not to do that and work all the time. So I could use this advice myself. Here's the thing here's the thing. Like the reason I'm so regimented about this is because like
If I'm not
I will fall apart. Like
There's this quote I can't remember where I s where I saw this, but I love it. It's like
You know, I have exercised the demons from my head.
But they are outside and they are doing push ups.
Like
The threat of the demons coming back is always there.
And so like I take this stuff really seriously because I know like
I if I'm not if if I let myself start to slide into like
I'm not doing the things I need to do to take care of myself. Like
I'm gonna have a bad time. The walls are start are going to start closing in around me.
And I'm not I'm not like shy about that. And so
To me, there's no
Point in
torturing myself and like
Just working so so so hard and having no room for joy and having no room for creativity.
Even just from a practical standpoint, like it's not
I'm not I'm just not gonna succeed.
So
This comes back to your point about I d I think it was called behavioral activation of like doing the thing.
Instead of waiting for you to feel a certain feeling, do the thing that
Will make you feel that way.
Yeah.
Okay. Uh
as maybe a final area, but I have a few more questions after this. So maybe not the final area is AI. Uh
I um
Uh happy that we waited this long to get deep into AI. We're not gonna spend a lot of time here. You wrote a whole guest post about this, you did how I AI to talk through some of this stuff.
But I when we were talking earlier you said that
You think people still are completely under
Valuing the
power AI could have on their ability to learn.
And improve themselves. And I know you spent a lot of time on this with
All these GPTs you've built.
Just talk about the sense of
How much you think people still underappreciate how much
power there is in AI and helping them become better.
Yeah, I think we are not being nearly creative enough when it comes to how to think about learning with AI.
And I think
You know, you hear people
Worry about
Entry level jobs.
And when you think about an entry level job
It is
Sort of uh
Inefficient by design.
Because you have like take an analyst, sort of a classic entry level role.
They're they're doing grunt work. They're doing really tedious work.
Um but they're getting a lot of reps in.
Because
That's exactly how you learn the judgment.
to do higher level jobs well.
And I hear this in creative fields too. I hear this like from every I certainly feel this way. Like the work that I did in the beginning of my career.
Uh
It was it
It didn't feel like it was all that.
Um
Important in terms of the impact it was having.
Uh, but it did feel like it was transformative in terms of my own judgment and my own taste.
And how I think about like
Just making like very quick judgment calls now. I just wouldn't have been able to do that.
If I didn't spend years
learning like
You know, I used I used to
do social media, like the skill of having to
condense something that I want to say.
into like
A hundred twenty characters or whatever it used to be on old Twitter.
Two forty?
Oh I can't remember. I forget actually. Isn't that crazy?
Like I forget what the original was. I think it was one forty. Okay, one forty three. It was it was short. And you got if you had to get a link in there, like good luck to you.
But oh my gosh, the my ability to just like
look at a something written today and just
cut it that text in half third, like whatever it needs to fill the space.
Like I can I can do that in my sleep because I got all these reps very early in my career.
And so
I think people see the way that
Uh
You know, there's a threat of companies not wanting to hire as much entry level talent.
Because um
You know, it's like, Oh, this is the kind of work that AI can do.
And so the fear that I hear, at least, is um
Where if you're not getting those reps early in your career.
Like maybe it's not contributing that so much value to the company at that moment.
But it's it's how you learn to be great later on. And so there's a fear that
in five, ten years, like we're just not gonna have that.
But
class of people
who have learned to do the jobs well and who have built judgment in that way.
But what I think that misses
Is it assumes that
You know, you go and you do this analyst job for two years and at the end of it
You have a person who
Uh
make models really well, knows how to do a few things really well.
But like why does that have to take two years?
And why does
That
model of like you
You grind over this thing, you wait for feedback.
eventually you get that feedback. Maybe that feedback's good, maybe it's not.
Um
You go back, you try again. Like it it actually is really inefficient when you think about it.
And the sort of learning applications around AI that I get really excited about are
How do you shrink that loop?
So
In my podcast with Claire.
I showed her how like I build these GPTs that kind of think like me.
And the purpose of that is so that my team can get
Feck that is
At least
eighty percent close to the feedback that I would be giving them.
But instead of having to wait until I get to their message or until our one on one.
They can get that on demand as many times as they want.
You know, forever.
And I think there's a lot of things like this of like
Ways that
Things that
Require other people just naturally slow things down, require getting feedback from other people just naturally slow things down. We can build AI tools that like.
You know, the at in my view there's no reason why
the amount of reps that you get at whatever task you're doing, like you can be a
You can be a film editor just like
Sitting there pouring over the film.
uh deciding like what to edit, what to cut, what to, you know, put into the trailer or whatever it is you're making.
That's an incredibly tedious job that takes forever.
And
I think there's no reason we can't like make that way more efficient with AI.
In way is that
Make the learning like
More fun.
Um
And so I just yeah, I think that that's sort of my hot take is
Uh yes.
It is like there is this threat of a lot of these jobs that are things that seem like you can just automate them away that might happen.
But like we absolutely still need to be investing in people's skills.
I just don't think we need to be investing in them.
historically in the way that we always have, and I think in the future we'll find that those ways actually seem
seem quite inefficient compared to what what's possible today.
It's such a powerful point. And we're already seeing this. I imagine you've seen these studies. I think it's in Nigeria.
uh where they give students AI tutors and they just like zoom
to the next they they they accelerate so quickly in there.
progression of just like reading and math, I think.
Like we're already seeing.
And and it's harder to measure in PM and product and all these things, but like in school, it's a lot easier to measure and we're already seeing results there.
Yeah, hundred percent.
And to make this very real for people, you have this specific GPT, I think it's called Socrates or what is it? Aristotle. Okay, oh no, we're gonna edit that out. Aristotle, Aristotle. Uh where it gives you scenarios in a product scenario like
I remember
Like give an example just to give people a sense of what this can do.
Yeah, so this came from I was talking earlier about learning how to make a really strong logical argument.
Uh, or just like a a strong argument for your point of view in general.
And the sort of fundamental skill for that, in my view, is logical thinking, logical reasoning.
And when I think about like the best way we have to test that today
Uh at least like the
best is maybe not the right word, but the standard way we have to test that.
the LSAT, like this the test that you take to get into law school
That is what that
Tests.
And it sort of gives you these different scenarios.
And we'll try to say like
You know, if
A is true.
Then which of the following
is true is not true, like sort of testing some of these different like logical relationships.
And
So what I did was I made a GPT that
I basically told it like create LSAT style questions.
Uh to to test logical reasoning.
But put them in the scenarios of things that a PM would encounter.
And I have like a version of this that's very specific to Whoop.
And working in consumer health.
But you could do it for anything, or you can just do generic, you know, however you want to do it.
And it's actually like it's kinda fun because it f it gives you the scenario and it's like
Um
You know, you're
The sales team is telling you that
Uh we need to invest in feature A.
And the uh
I don't know, the engineering team is telling you that we only have time to do feature B.
And uh the metrics are telling you that
Um, you know.
People who
get this feature retained better. Like it just sort of gives you these little things and it's like
Follow that logic.
Which is the
Which is the logically best path from this?
And it gives you a little multiple choice answer. You select one and then explains why you're right and wrong.
And so I think that's just like another example of
You know, you can't you can't create those like hyper personalized learnings where I can make one that is like literally so specific to you and your life.
Um, but is like testing and and sort of like training you on this like
broader skill set.
And I think you can you know, you can make things more fun that way.
uh even in just like the school context in terms of doing that in a way that's just relevant to a person's interests relevant to the things they care about.
Um, I think there's a ton of real interesting potential there too.
So we're gonna link to this GPT that you're talking about that and people can try it out. And once you see it, you're like, holy shit, I I should just be doing this the whole time. Cause you just get so many reps as a
as a
product builder. Uh And that's you know, we we were talking about a similar one uh with
Like understanding engineering benchmarks. I don't have an engineering background, so
This was really hard for me, like when I was moving into product is just getting an instinct for
What types of things tend to be easier or harder for engineering teams?
Um
And so
We can have one similar that's saying
Uh
You know, like
Here's the scope that's being proposed.
If you had to T shirt size this, like
Which one would you choose and why?
And you can say, Oh, you know, this town's small or whatever and it'll say, Oh, actually like
These types of integrations tend to be complex for these reasons, so it's probably gonna end up being more like a large.
And it you know, it doesn't have enough context to like really
Like
inform you in the way that
Uh
you know, your your tech stack at your company is, although I guess you could build it and give it that information and then it would.
That would be cool. You should do that.
But again, it's like you do that like as a PM
You might get a chance to do that.
I don't know, a couple times a week.
Maybe?
Maybe less often than that.
And when you have this little tool, you can do it.
Infinity times. You can do it, you know, you can spend an afternoon doing it. And so again, like
Both the speed of those loops and the like
the number of those loops that you're able to get.
is just like radically different with AI compared to just like
when they come up in the course of your job.
I I think this is extremely cool. Uh we're gonna link to it. People should definitely play with this.
Okay.
I'm gonna take us to two corners, recurring segments of the podcast, and then I wanna talk about Woop.
uh before we get to our very exciting lightning round. So this is a new segment I'm trying out. I'm gonna call it Pivot Pivotal Corner.
And here's the question.
What's the most pivotal moment in your career?
I mean I think it was at my at my former company.
Um
I big health when I
Uh my former boss left the company and I started recording into the CEO.
And again, I think it was my first time just having like up close
Uh
Like working with a CEO so closely.
And it just like
Definitely trial by fire.
Uh but it
It made me understand so many things that seemed
Like they didn't make sense to me before when I was just like in the rank and file of like a big tech company earlier in my career.
You get in the room and you talk to these people and you're like
Oh, this like this actually makes sense. Like I understand why this person has come to these conclusions.
Um and some of it's like understanding the pressure they're under. Some of it's understanding again like the w the way they view the world.
Um, but I think that was, you know, to get to our our earlier point around like the humility of understanding that like maybe this person is right about something that I don't see.
And maybe I can start by
If I start by giving them the benefit of the doubt, it is not only like
A a a nice thing to do.
But it is also like
It will get me
It will help me understand why they're doing the things that they are.
And I think I would have been so much less frustrated earlier in my career.
If I understood that, instead of just being like
Oh, this doesn't make any sense from where I'm sitting, so therefore it must not make any sense.
It's so cool that this connects back to your habit of
Doing this.
having seen it and being like, Oh, I see, this is why
Yeah, I guess I'm maybe I'm wrong. Maybe I could be wrong.
Well that's I mean, that's what it is. Like I feel like I've had so many of those times where like
I don't know, when I was growing up I was just so like
I felt so confident in like how I felt about everything.
And then you get and you get out there and you're just like
Oh, I was I was missing some things and after a while you're kinda like
Okay, maybe I should maybe I should approach these situations a little differently, with the with the possibility that maybe I'm missing something.
So I actually asked your boss Calvin, who's which is an awesome name, by the way, Kelvin, uh
about this moment. When I asked him what to ask you and he brought this up actually, and here's the way he described it.
She may describe it as being thrown into the deep end or baptism by fire.
But the reality is that she had the core skills and this was simply an opportunity for her to let those shine even more.
She w she was an incredible first principles thinker, quick to tune the framing of problems as she learned more context. It's a great example of luck is what happens when preparation meets opportunity.
Thanks, Galva.
That's really.
Uh he also said I wonder if she remembers how terrified she was now because she absolutely knocked it out of the park.
And
I felt it felt like it was an inflection point that grew her confidence significantly.
Oh, I was terrified.
Uh yeah.
Big time terrified. And then I mean this is also like
What what I was saying about uh why it's so important to like be regimented about
having these things outside of work that allow you to continue to thrive even in the face of just like
Utter feelings of failure of like
I am not doing a good job. This is not going well. I don't know what I'm doing.
Um
You know, a was that time. Kelvin actually gave me some great advice that was uh
But this is maybe kind of scary advice, but
When I ask him.
Uh what his advice for me at the time was and he said
Product leadership.
is a the type of role
Where if you are not in control of the voices in your head, they will eat you alive.
And
You know, I I think it's right. Like I s as I said, it is so often this like
Feeling like there is not a clear right answer.
And not even necessarily a good answer.
And everyone is looking to you for clarity.
And everyone is looking to you to make the right decisions.
And
Everyone sees the errors, or at least like everyone can spot
The flaws in whatever decision you make or whatever recommendation you make.
And
You know, you
As I said, like
Every path forward has flaws that can be poked in it.
And so
understanding that like the existence of
potential ways to be criticized about something.
До
Does not warrant criticism in a way that
Like can I think often result in a lot of n negative self talk for people. So
Yeah, I mean it it had a tremendous impact on me.
It's interesting how so much of these habits and skills you've built seem to like it's clear where they come from.
From all these experiences that you had.
Well, and back to the point of like when you when you start talking to people and you start trying to build this mental model of how they think, like
That's exactly what you learn, right? Is
Well, I can see how
this person kind of, you know, worked at this company at this time, and I can see how this person
Had this kind of
relationship with this other person and like
All of these things shape the way that we approach problems and the way that we try to
You don't just move through the world.
And it is like it it it is understanding those types of things that allow you to understand how a person thinks.
I wonder if you could ask JetGPT to build or Claude to build these mental models. Like here's their LinkedIn, here's their bio, here's a few things. What's how do they see the world?
I will admit that I have
tried this.
Yeah.
And
I think it I think I think it's a great idea. I think it does help. I have not gotten to a point where I'm like
comfortable sharing it with other people.
Uh nor have I
told anyone that I have tried to do this for them, but I've certainly done it for myself.
Uh and
Yeah, I think it would be helpful.'Cause'cause you could say things like you could upload a you know, doc or whatever and be like
What are the three questions that
This person's gonna ask me about it.
Uh, and then you could be prepared for the questions that that person's gonna ask you and
That's great.
Uh, in this hypothetical example, what do you what do you what context do you share with with this model to help it be good? Great question. Uh hypothetically, uh you know, I told you that I take all these notes on
Here's what
This person said, and here's how I interpret it.
And LLMs are really good at pattern matching and sort of spotting the like
You could you could feed all of those in and just say
you know, come up with the the like ten criteria that this person is most likely to use to uh assess uh
possible recommendation or path forward.
Um, or give me like
The top ten ways that this person is
uh like likely to
pick apart an argument or object to something and
it you're gonna get a good answer.
More reason to
Build this habit of taking notes and sharing with your team.
On the other hand, this might also be a good use case for granola or something like that where you
Have all these meeting notes and you could just feed it. Here's all the things Hillary said. And oh, what is she what is she probably gonna say about this?
Wow.
So cool. Okay.
Next corner, I'm gonna take us to fail corner.
And in Fail Corner, the idea here is
People come on this podcast, they share all these wins and success. Everything's up and to the right and amazing.
But in reality, things don't always go that smoothly.
So the question is just is there a story you could share of failure in your career?
where things didn't go the way you hoped. And
What you learned from that experience.
Um, I mean I think the one that probably
uh looms largest in my mind is
I'm you know, I mentioned this uh depression therapeutic that
Uh I spent about a year working on and
Uh, ultimately the company ended up acquiring a different depression therapeutic. Um, and we kind of ended up like
merging the two of them.
And
a lot of the stuff that we had initially built that I would have really loved about this product we were working on.
didn't really ever end up seeing the light of day beyond the kind of
testing that we had done around it.
And it was heartbreaking because like
I still
I wish this product existed. Like I look at it and I'm like, This was a great product and we put
So much heart and soul into it.
And I think the like the lesson that I learned from that is
Um
I think there's there's always a shot clock, right? When you're working, especially on a zero to one product.
I think it can be very easy to feel like you have the luxury of time of just like
You know, we gotta we like we gotta take the time to figure this out and get it right. And that's what's most important.
Um
But
The the sort of build versus buy question is always live and it's always fair.
And
Whether you want to admit it if you're the one working on it, and you probably don't, I I didn't want to admit this. Um
There is a point at which like it it makes more sense for the company. Like if it is taking too long to develop something.
And there is a a solution out there that works, like
It is the right decision.
to acquire that.
And
I mean I've s I worked at Dropbox for a while, I saw this happen all the time where we would
Acquire products that
other teams internally have been working on and it's just like it's kinda heartbreaking when it happens.
But I think there's like an urgency that that has installed in me.
That I think is actually really good and healthy.
Um, especially again like
working in this era where there is kind of this AI arms race and everyone's trying to move really quickly.
Of like
Yeah, there's there's always a shot clock.
And you might not be aware of it, but it's there.
Uh, and you gotta you gotta build your heart out and you gotta ship and you gotta get things out because
Uh at any time, like that clock might run out.
Speaking of shot clock, not necessarily, but uh I want to spend a little time on Woop. The you guys just launched something uh that's
feels like a really big deal. I'm excited. That's the reason I got it. There's all these really cool new features.
Uh
I think you call it Whoop five point oh.
What should people know? What's the newest coolest thing that's happening with Woo?
Yeah, I'm really excited you got it. I know I know you tried it before and That's right, that's right. People who have tried Whoop in the past maybe felt like it was
Like very focused on like
elite athletes. And that is why we've got the company.
And I think what we've what we've done with our new experience is
Uh we've really built something that can
Help everyone be healthier and and live better.
Um
I think we're
I would say we're no longer for just for elite athletes. Like we're really now like a a health and performance companion for
Anybody who wants to feel their best.
Um
For the first time in our company's mission or
History. We've updated our mission.
So we're now saying that woof exists to unlock human performance and health span.
Um, and Hillspan I think is and I mentioned earlier the speech I'm really excited about.
Because I do think it's it is kind of the
most powerful version of like a
Longevity type feature I have seen.
Because it is so focused on your behaviors and your habits today.
And we built it to be super, super actionable.
So rather than just like giving you a score that you're kind of like okay, that's nice.
If you start sleeping even like twenty minutes more, thirty minutes more tonight.
Like you're gonna see how that changes your pace of aging. You're going to see how that changes your age.
Um
And I think that as I I mentioned earlier, I think is really rewarding.
We've also have a lot of personalized coaching for our AI in terms of actions that you can take.
to improve your woo page.
Uh to improve your sleep, to feel better.
Um, and it's all part of our broader aim to make health more actionable and accessible.
I think one thing I'm really excited about is we have a bunch of new uh women's health
features so we have uh hormonal insights.
with uh improved menstrual cycle tracking.
Uh I'm actually pregnant.
And I didn't know that. Well, I have a big announcement. Wow, congratulations, Hillary. That's so exciting.
Uh but I actually I
Part of how I found out I was pregnant was in seeing my
Yeah. What would just be remarkable and the way that we have this the cycle tracking now.
You can see the way that
Your different um
you know, your HR V arrest and heart rate, things like that.
That's your heart rate var variability in your resting heart rate.
fluctuates throughout different times of your cycle and and
Even in like the times leading up to that, like I had a not straightforward pregnancy journey.
And having these tools to like really understand what was going on in my body was tremendously helpful and and tremendously like
empowering for me and and honestly really has changed my life. So
I'm really excited about that. We have a lot of great new uh heart health features. We have a heart health screener uh with blood pressure insights and ECG that's really cool.
Um
We got a lot of s a lot of great stuff cooking, so
Even if you tried Web in the past and thought it wasn't for you, um
I think the the new experience is a real upgrade, and it's it's something that I'm deeply proud of having worked on.
Um, and really excited to have out in the world.
I am generally very excited about this. Like you could do uh you said blood pressure and VO2 Max. It's and and I know the battery is even longer, too. There's just like so much. We got a fourteen day battery life. I didn't say we have these beautiful new leather bands. Oh wow. Uh fourteen day batteries life is is insane. Like I'm going on vacation.
Tomorrow.
And I'm like, I don't even need to bring a charger. Like this is fantastic. Oh man. Like this sounds like a whoop ad, but I'm like very excited about this. But I'll say one more thing, which is we also have um
We've opened a wait list for advanced labs.
And so pretty soon you're gonna be able to have like comprehensive
Lab work.
Uh in the in the app.
And I think
You know, we talk about the the future of health of having like control of all of your health data in one place.
And then being able to like
Not just sort of
find the signal in it and and sort of understand like
you know, how your sleep is impacting your metabolic health or things like that.
But again, get really actionable coaching on actions that you can take to to feel better and be your healthiest. Um and yeah, just pushing pushing the limits of all the data that that we're pulling into blue people system. So really excited about that too.
I'm hoping the whoop can actually take my blood and labs. Is that is that where this is going?'Cause that'd be so convenient.
Okay. That'd be like it'd be weird, but also awesome. I don't have to go anywhere.
To do that.
Uh Hillary, we covered so much ground. Okay, before we get to our very exciting lightning round, is there anything else that you wanted to touch on? Anything else that we haven't covered that you think or or last nugget you wanted to leave listeners with?
I don't think so. I feel like we covered everything. We did. We covered so much. Uh in the best way possible. With that, we've reached our very exciting lightning round. Uh are you ready?
I'm ready.
What are two or three books that you find yourself recommending most to other people?
Oh, but it you can.
Call something a lightning round and then ask me about books. That's like we could we could go for a whole other podcast where I'm gonna go.
Yeah.
Exactly.
Okay, I'm gonna go you know what I'm gonna say? I'm like
Uh, I'm gonna go full fiction on this. I'm gonna say if you're gonna read a book like
You d don't bother reading a business book. Like
I even the business books I love the most that like shaped how I think. I'm like I kinda got the gist of them part way through.
But
Fiction, I'm like
Everybody should read East to Eden by John Steinbeck, and everybody should read The Sun Also Rises by Ernest Hemingway.
Uh
Uh it was just like my comfort book.
I think I like what I love about fiction is it just
It teaches you how to sit inside tension, right?
I think
So much of working in product is as I said, like you're in this fog and you just have to provide clarity and you have to be really good at like
providing structure to ambiguous things and finding the way forward and like
To succeed at the job, you have to be able to do that.
But I also think to succeed as a human in the job.
You have to be able to sit in the mess and sit in the ambiguity.
Um
John Keith, the poet, talks about this concept of negative capability.
Which is the ability to remain in uncertainties, mysteries, doubts without any irritable reaching after
Fact and reason.
And I love that.
That sounds like a perfect quote for L PMs to Exactly. And it's like it's uh you got you gotta be built right again, fiction. I love dualities. There's a lot of dualities in fiction, a lot of like warring forces within a people that is like
You know.
Can be so driving for people, but can also be the source of so much anguish.
Um
I think it's it is important to
live in both in the I'm gonna break down this problem.
When I structure it, I'm gonna get out.
But also like
I'm going to sit here and I'm going to accept that there is no right answer and there is no perfect answer.
And I I
That's life.
So
You know, you don't learn that from
To the extent that you learned that from a book at all, which
Maybe you don't.
Uh but I think you can I think you can learn it in fiction.
I don't know how you feel about this book. I think you'll be proud of me. I'm reading Anna Karenana right now.
I was I literally uh that's the book that I'm bringing on vacation with me tomorrow. Wow You never you've never read it?
I've never read it. Cool.
Me neither.
Okay. We'll exchange some notes. It's very long I'm relaxing'cause I'm reading on the Kindle like
Only twelve percent. Okay. Now now I really have to read. I was like kind of wavering. I was like, is this really what I'm gonna want to read when I'm like sitting by the pool, but no, I've come in. You gotta do it. Another guest recommended it and I saw it on some lists recently, and then like oh I should read that.
Why.
Next question. Do you have a favorite recent movie or TV show that you've really enjoyed?
Um
I've been watching the rehearsal with Nathan Fielder. Have you seen the show?
I saw the first season. I've been a huge fan of Nathan Fielder for so long. I don't know if you saw his previous thing that he did. I forget what it's called. Okay. He's so hilarious and such a genius.
Nathan for you. Oh my God.
Uh I haven't seen the new season though.
It the man is a freaky genius. Like
I I just when I thought that I had like a good sense of all the human emotions that exist
out there.
Like I watch the show and I feel things that I'm like
I have no I feel like 10 different things and I'm like I have no words to any of the things that I'm feeling right now. Uh it's it's weird. It's weird stuff, but I'm enjoying it. I gotta watch it.
Do you have a favorite product you've recently discovered that you really enjoyed other than the whoop?
I love my zwift.
Swift it's like a a
program that you can hook up a smart trainer to, like for an indoor cycling situation.
uh and you kind of bike around like you're in Mario Kart and you're sort of in these virtual worlds biking with other people.
Uh it's I think for very serious cyclists. I am not a very serious cyclist. For me, it's been amazing as somebody who.
Actually really like struggles to find time to exercise.
Um I like that they have speak of reward loops. They have one of the most amazing reward loops, which is
You're biking along and you you get into this like
Um track.
And a ghost of your previous self breaks out from you and starts racing alongside you.
at like your personal best for that track.
And you have to beat your personal self, or you have to beat this ghost version of yourself.
And like nothing has ever motivated me more in my life.
Than like past Hillary.
being like I'm coming for you and I'm like
I don't get that competitive with other people, but like past Hillary comes for me and I'm like uh this I can't let happen. So I I think it's a great product. I'm thinking about how to use that tech that uh m um I don't know.
mo mode for other use cases like the ghost version of something to motivate you. I've been I've been in so many product meetings where I'm like, can we make like a like a ghost version of yourself? Yeah, okay. Like shut up about the ghost
Uh huh.
Okay.
Amazing.
Okay, two more questions. Do you have a life motto that you often come back to find useful in work or in life?
I've I'll say one that's been top of mind me recently.
Uh, because I was talking about the highbrow fiction, I also will have to go low brow.
I saw this uh clip of Beavis and Butthead online recently.
Where they were watching a music video for Cree by Radiohead.
And it starts off really slow and one of them I think maybe
But is like
Oh, this sucks. And then the chorus comes and it starts getting like
All hyped and they're like
They're like, Oh, this rocks, this rocks.
And there I'm not going to do my decent but head and pressure.
So then it gets back to the slow part and
Uh, they're like, Oh, wait, this stuff's again And then Butthead is like
Why don't they just play the cool part the entire time?
And Divis is like
Because if they didn't have the part of the song that sucked.
The cool part wouldn't be as cool.
And I was like, that is so profound.
Like that is
That is what life is all about. It's just like
If it didn't have the parts that sucked.
The cool parts wouldn't be as cool.
And we're always chasing the cool parts. We want it all to be the cool parts, but it can't.
So thank you, Beavis and Bad. Thank you, Beavis and Bad.
Okay, final question. I love that you talk about fiction books because this is where my question was gonna go. What's a fiction?
book that most impacted your product.
building approach or career.
Or the way you think about product.
Can I give a poem?
Absolutely. Even better. Poem, extra credit.
There's a poem by Derek Walcott.
Uh about it's called Sea Grapes.
And it's about
Odysseus.
And he talks about
Uh
Odysseus being driven by the ancient war.
between obsession and responsibility.
And
I read that line when I was like eighteen years old and it has always stuck with me.
Um and I you know, I I sort of mentioned earlier I think about these like dualities that that drive us.
And um
I think
Yeah.
As a as a product person
I always feel like I'm like living between these two, like the obsession and the responsibility. Like I just I wanna like
I wanna go so deep on this and I wanna I wanna spend like as much time as I possibly can.
Just like
Sorting every little piece out.
But like we o we
We live in a society.
Uh we exist in a business.
Uh I am trying to create value for shareholders.
And trying to like bring these two things together.
I feel like A has been like a you know, the kind of defining struggle of my career, I think of many people's careers is like
How you have something that you feel like you can really obsess over and have that flow over.
Um
Or have that flow when you're working on.
But then like
It's gotta it's gotta kind of like work in this broader system as well.
Uh and I think that that's sort of been like the
the thing that I think of as the guiding post for like what I want to do with my career and with my life.
Um so I think it's
Gotta be Derek Wilk.
What a beautiful way to end it.
Hillary, two final questions. Where can folks find you online if they want to reach out, maybe follow up on stuff that you talked about? And how can listeners be useful to you?
Great. Thank you. Um, so as I mentioned, I have a newsletter. It's hills.substack.com. That's H I L S.
dot substack dot com.
Um, I'm also teaching a Maven class on being a super manager.
Uh, with AI. So if you were listening to all this and you were like, Oh, Hillary, that sounds so great, but like
I don't have time for any of that.
How do you have time for all that? Like
Honestly
hyper leveraging myself with AI has has been a big part of how I find time to do any of this stuff.
Um
And so I share a bunch about how I do that, how I use AI as a manager, um, building on a lot of the the stuff that I shared on Claire's podcast as well.
Uh how I AI.
Um, so you can find me on Maven there. We've got a couple of cohorts coming up.
And then uh yeah, I encourage everyone to to try out Woop.
You can get a free month on me.
At join dot com uh join dot woop dot com slash Hillary.
That's Hillary with one L.
And you can
You can post at me or tweet at me.
On
X.
And let me know what you think of it and I would love everyone's feedback'cause we're really excited about it.
As you were talking, I looked up your course just for make sure people can find it. So you go to Maven.com, you just search for Hillary Gridley and you'll find it.
And it's you can also I realize that if you Google super manager, you will find me. So that is my new claim to fame. Oh my God. That's so great.
Uh four point nine stars. Holy moly. There we go.
Okay, Hillary, thank you so much. This was incredible. Covered everything I was hoping to. This was everything I wanted it to be. Thank you so much for being here.
Thank you. Thank you for having me. This was so fun.
Still fun.
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