Unorthodox PM wisdom: Automating user insights, unselling job candidates, logging every decision, more | Kevin Yien (Stripe, Square, Mutiny)

Transcript from https://podmenti.com/t/5362d0c4b4940d1d

The PM job can become a little too internal, influencing my stakeholders and getting alignment and all these things. But if you can't sell or support your own product, I don't trust you to build the product. You think every PM should keep a decision log?
We all talk about product sense. To me, it's just a fancy way of saying you can make good decisions with insufficient data. PMs need as many reps as possible in making decisions, documenting the rationale behind those decisions, and then crucially seeing the outcome of them. We have a lot of interesting approaches to hiring, including this idea of a unsell email. When you get to offer stage.
I send an email and I say all the terrible things that are probably going to reinforce their fears. If you can tell them that up front and they can read that whole email and still be equally excited to join, you find yourself in A plus hire. I'm curious if you found any interesting uses of AI in your work. We are not even beneath
The dust on the surface when it comes to what's gonna change.

Today my guest is Kevin Yen. Kevin leads product for merchant experiences at Stripe.
Before that, he built the restaurant business and the ecosystem teams at square.
And most recently was head of product and design at Mutiny.
He also makes ice cream and as you'll hear in their conversation was a pretty competitive eater for some part of his life.
In our conversation, Kevin shares a ton of unique and insightful perspectives on how to be a successful product manager.
including how to get into product management, how to improve your relationship with your engineers and designers, bunch of advice on hiring, why you should keep a decision log,
How to automate your customer research.
plus a ton of really powerful stories around failure and AI and career.
This episode is for anyone looking to become a better leader.
thinker and builder of products.
If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube.
It's the best way to avoid missing future episodes, and it helps the podcast tremendously.
With that, I bring you Kevin Yen.


Kevin, thank you so much for being here and welcome to the podcast.
Thanks, Lenny. I am humbled to be here.
I've been a big fan of yours from afar. I've been following you on Twitter for a long time. You have a very distinct profile photo that I feel like you may be not a
Haven't changed for a long time. How long have you had this
This project.
Probably twenty
eleven or twenty twelve. The story behind that is
I was inspired actually by Chris Dixon's avatar at the time.
And I wanted something really similar to it.
But I couldn't figure out how to. Luckily I was dating a designer at the time.
Uh and so
She made me that sort of custom pick.
That has been my profile since then. And she's now my wife.
Oh my God. I uh funny enough, I had a startup idea once where it's like a
profile picture as a service business where there's like these three tiers where it's like one is automated.
One is someone illustrates and one is like a professional photo as like it feels like everyone profile photos are so important.
Yeah, but I never I never follow through. Probably not a good business anyway.
Yeah, but a good idea. Good tool. Good idea. Thank you. Thank you for being making me feel better. I've been
Looking forward to this conversation for a long time. As I said, I've been a big fan of yours for a long time.
Something that I've noticed about you is you have a lot of really unique perspectives on a lot of different things and in particular product management.
How to be successful as a PM, how to get into product management, things like that.
So I thought it'd be fun to start there, talking through some of these things that I've heard you talk about.
And then get into some very tactical stuff that you found to be useful.
In
Your product management.
Career.
The first thing that I've heard you
Talk about is that
You
Discourage people.
From going straight into product management, if they want to become product managers, you encourage them to start somewhere else first.
Why is that? Where do you want where do you think people should start? Talk about this insight that you've had.
Yeah, so
Follow me on the detour to science world temporarily. If we if we all remember sort of like high school science classes, there was like this concept of potential and kinetic energy.
And
There's so many different definitions for like product management, but the one that I have come to myself that I really like.
Is
When you are building a product, you have this team, right? Engineers, designers.
So much potential.
And the purpose of
Product management, not the person, but the practice.
It's to convert that potential.
into
As much
realized value for someone as possible, right? Minimum loss.
And
When you're just getting started with a new product.
The people that should be doing that are the people who are building it.
Right.
That's an engine, that's a designer, that's a salesperson.
Or a support person.
They're the front line of the smallest loop possible.
To get something going.
And
It's through those practices that I think
you're able to get the most exposure.
To what it takes to build a good product.
And then from there, that's your foundation, right? That's the unique perspective that you bring.
And allows you then to actually take on a quote unquote role.
A product manager in a good, unique insightful way.
So that's sort of like the foundation and there's a lot more to unpack behind that comparison, but
That's where it comes from.
I love that.
Uh I'd love to unpack it further.
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I'm excited to chat with Christina Gilbert, the founder of One Schema, one of our longtime podcast sponsors.
Hi Christina.
Yes, thank you for having me on, Lenny.
What is the latest with one schema? I know you now work with some of my favorite companies like Ramp, Vanta, Scale, and Watershed.
I heard that you just launched a new product to help product teams import CSVs from especially tricky systems like ERPs.
Yes, so we just launched one schema file feeds, which allows you to build an integration with any system in 15 minutes as long as you can export a CSV to an SFTP builder.
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Every PM has their definition of what is product management.
Yeah. And I have one that I'm trying to find exactly what I what I wrote, but
Essentially it's to marshal the resources of your team.
to solve customer problems and drive business impact.
Most efficiently, something like that. And I feel like it's very aligned with your perspective, but I really love this
view if it's like unlocking the potential energy of the team, not just
marshalling the resources of a team, but it's there and your job is to maximize their
Ever and this is why
When people say like I hate product managers, I don't want any product managers on my team with we don't need product managers here.
I feel like
That's often because you've had a bad PM.
Good PMs make you
Better.
Life better.
allow you to do the work you want to do. And they take all the stuff you don't want to do. Make sure the stuff you're doing is
Is worthwhile.
Is there anything more you wanna add along those lines?
To elaborate on that, I think
The broader point is that
Truly, not every team needs a product manager.
But
The activities, the outcome that one would drive.
Needs to get done no matter what.
And in some cases, this is why the prototypical companies that everyone references when they say
They never had product managers. Look at how successful they are.
They're all building for themselves.
Stripe.
Twilio.
Uh Figma, like
Designers for designers, engineers for engineers. When you are the customer, why the heck do you need someone else?
To help do the things that let you make decisions.
On what to build.
But
If you are
Not the customer.
If you're working in a particularly complex space.
If there's something that you as the person that could build the product feel
You don't have?
That's when you can essentially delegate
That responsibility.
To someone else to say, Hey.
Let me do the things I'm really good at.
And you do something that I need to get my job done.
So
It's that sort of relationship that I think is often missing in the discourse.
And I think it would
alleviate a lot of the
We
Don't want PMs. PMs are useless.
Or PMs are the best thing since I spread, which they are not.
Uh it's just
And manifestation of that problem.
Yeah, just to to build on that, we're going on a tangent, but I think that's really interesting.
I think there's another element of that.
Like Snap actually is another example where they waited I think till they had two hundred people before they hired their first PM.
And it to me that's an example of other people were doing the PM job. As you said, there's like PM activity, someone's doing them.
Lining people, prioritizing, making sure
Things are clear, making sure people aren't surprised, all these things PMs do.
Like someone's doing that.
And my feeling is like, Okay, your designers may love doing that. Great.
Let'em do it. If your engineers that have a lot of product sense.
May want to do that great.
But there's some point that you either's like, forget, I just wanna code, I wanna build, I don't wanna be sitting around in meetings all day.
Or they just aren't as good as it's things are scaling.
And so
It's kind of like if your engineers, designers want to do it and are good at it.
Great. You don't need PMs for a long time.
Oftentimes they're not good at it or they don't want to be sitting and doing all these PM things.
Yep.
Precisely.
Okay, so going back to uh the question of your advice is don't go straight into product management if you want to become a great PM.
Where do you think people
should start if they can. What are some options you recommend?
The best way to think about this in my opinion is
Who were the people that you would be sort of
Taking the PM responsibilities from
And then
Do those jobs.
And so for me the sort of foundational three are gonna be like engineer, designer, or
Salesperson.
And it doesn't have to be I think sales
Also gets
Not a bad rep, but a misrepresented.
Reputation.
In tech.
Where
All they care about is quota, it's just about numbers, et cetera.
In reality, the best salespeople are the best listeners, the best
Best.
People at understanding
the problem that the customer is having and then translating that into what you can do for them.
And so if you get really good at
Having those calls.
Getting told no a lot.
And being able to translate that.
I mean
Why would you not want to start there and then eventually move into something like product? So that's like the foundational three for me.
So your advice is essentially if you want to be a PM, start as an in as a designer or an engine or a salesperson.
Uh I was an engineer, so this is exactly the path I went on.
I think there's a
Uh like an element of
You start there and then you realize you're never gonna be as amazing as the other people at that role. And you're like, Okay, maybe I should explore this other thing because I was like, I'm never gonna be an amazing engineer. I'm like, Good enough.
Like.
I'm pretty good at this other stuff. Let's explore that.
The the one thing that I might tack on there, because this could lead to a a negative perception is
Well, I'm never gonna be a world class engineer, world class designer, or et cetera.
And so let me settle
for being a PM, that could be the conclusion you arrive at.
But I think a better way of framing it is
I'm okay at those things. I'm potentially world class at this other thing.
Let me see what it feels like to double down on this area. And
I think that's just a good brand.
Okay, so let's talk about another insight and piece of advice that you have is
That
You think that
Great PMs need to be great writers.
And I think a lot of people don't necessarily think this. I think people may probably think um
If I'm okay writer, I can probably be a really successful PM. Talk about why you think it's so important to be a really great writer to be a really great PM.
It's actually shocking for me to hear that this isn't
commonplace sort of acceptance.
Fine.
The
The place that this comes from for me is
Writing is clarity at scale.
And
A key component to a PM job is creating clarity.
Both internally and externally.
But it's it's both sides of that that I think often get lost. A lot of times
The PM job can become a little
Too internal.
And it's about
influencing my stakeholders and getting alignment and all these things.
Don't get me wrong, all that's very important.
You should write your PRDs, they should be super crisp, they should articulate things really well.
Might.
I'm not saying that every PM needs to be a marketer or a world class copywriter.
But you should be able to write really compelling messaging.
in the voice of the person that you're trying to serve.
And
I'm working backwards from the belief that
If you can't sell or support your own product, I don't trust you to build the product.
And so that's where I think writing is the foundational component there.
There's like a few quotes I say often on this podcast just'cause they always come to mind. One is
By Joe Diddyon.
Who said that I don't know what I think until I've written it down.
And that's what I find with writing, where I need to like actually write it down for me to like really understand what the heck I'm thinking to really crystallize it.
Yeah. And I think.
Writing is
It's both a mechanism.
for translating what you're trying to think.
into that thought.
Into like what you're actually trying to do.
But then it needs additional revs to be properly consumed.
By everyone else. And
That's I think the really hard part though.
a lot of folks don't do the extra mile effort.
to take out.
And this connects to your earlier point of a job of PM is to unlock this potential energy of your team of the various resources you have and
Obviously having
Everyone aligned.
behind a very
Like this is what we were doing and everyone understanding it.
And it being very clear is really powerful there.
Uh okay, so this begs the question, how does one become a great writer?
What helped you become a better writer do you consider like how do you feel about your
Ability to write at this point.
And you guys becoming better.
I'll I'll start with
Like a slightly cheeky comment, which is I think some of this is changing with
the advent of large language models and the ability to actually just like mimic someone else's tone.
But
I I take inspiration from the camp of Anthony Bourdain.
And
He has uh I'm gonna butcher the exact quote, but it's something like
If you want to know how to make good food.
You have to eat a lot of food.
And you have to be willing.
to have a bad meal every now and again.
And so for me, like good writing comes from consuming as much good writing as possible.
And
Sometimes you'll read something and say that was actually absolute trash.
But that's okay. You have to be willing to take on some of that stuff.
But the more you index towards
Developing your own taste for what you think is good.
By consuming others, then you can shift into
Producing your own and then comparing them.
and riffing it off other people. So I think that's sort of the cycle that I've gone through.
I have a friend who's a very good writer and a poet and
helped me develop my writing early on, Vanessa, and she said exactly the same thing.
Just to g become a better writer.
Read beautiful writing.
And it just kind of it infuses you or your brain.
Uh in your experience, is there anything you
Read anything you found really effective, anything that you think influenced the way you write or think.
That people can check out.
I explicitly do not mean
Read a bunch of other
PM artifacts. Like you're not gonna become a better writer by reading PRDs.
Or you know, whatever it is.
Uh or support articles. It needs to be
Writing that compels. Like that's the
the theme I would go back to because that's what you're trying to do at the end of the day.
And when I say compels, I mean
it pushes you to action. Cause if you read something and you're like
Oh, that's interesting.
That's not enough.
Right, you need to be able to give someone something that then allows them to do something differently.
And so
The things for me.
that have been best. Obviously there's like all the Paul Graham essays, I think his writing is very succinct, very clear.
That's not novel.
I
I learned a lot by finding specific voices back in the day on Twitter.
And it wasn't always what they were
Posting on Twitter?
But if they wrote an essay or a post.
That would be their crispest thinking.
And so you can use these like broadcast channels to find where they're
Gold Nuggets are?
But then spend time with those instead and don't worry about all the additional noise that comes with it.
Paul Graham actually mentioned him, he has a great piece on how to become a good writer that we'll link to.
Where this basically his advice is right the way you talk.
Just like keep it really simple and really regular and sub link to that.
Is there anything else along these lines of writing that you'd recommend for folks that are like, okay, I need to become a great writer. How do I do this?
Actually along the lines of
Right how you talk.
Uh there's this concept of
Cadence.
that I think is really important.
When it comes to internal writing.
And it's
There's probably like some very good article about this, but it's the idea that
If you only write
in a monotonous cadence, either all really short sentences or all really long sentences.
Then
your brain just tunes out eventually. And so you have to interrupt the pattern.
Intentionally.
And so you go short, long, long, short, whatever it is.
But there's a few very specific things that you can do.
That
allow someone to just roll through.
uh you know, a post or something.
When you write that way.
Along those lines there's a book that I just found to make sure I had the right title called Several Short Sentences About Writing.
that is uh really helpful along these lines.
And the whole book is like very short sentences.
And it teaches you to write very short sentences because once you're good at that, you can get better writing longer sentences.
And so we'll link to that too. It's like a really
Good book.
Uh that I have like two copies around my house that I kinda poke at sometimes.
Nice, I'll have the part two.
Yeah.
Okay. Uh another area that you have a really clever insight into is
how the PM role fits with engineering design.
We've talked about this a little bit, but you have a really clever way of just thinking about how these roles interact and who's responsible for what.
Talk about that.
So
This
This description came from
Writing PRDs at Square.
And I think there was a lot of
confusion from my team specifically when I joined them. For what it's worth, it was uh new product line, three engineers, three designers.
There was nothing but a slide deck. Three engineers and three designers?
the best ratio ever. This is a whole other thing.
Uh.
Ever most people I would say.
Under invest in design, point blank.
And
When you get to a certain scale, maybe things change, but like truly
I don't think most
Teams have experienced
What it feels like.
to have a really high design ratio and what that actually does.
to
the quality of the work.
And like the quality of the thinking. So
Shout out to designers. Uh
We need more.
Is the the short version.
And I would rather hire an incremental designer than PM almost any day of the week.
So
I've never experienced this ratio. Incredible.
Yes, I was very lucky. Uh shout out to Bruce Bell, who was my manager at the time, who was an ex designer at the time GM.
And
Like.
declared sort of that starting ratio.
So
Anyways, with that set up.
Okay.
They all had sort of like an opinion. They had seen PRDs in the past. They weren't quite sure what the purpose of it actually was because they had designs already.
They had something to start from.
And
When I came in and talked to everyone and
figured out where we needed to be in a year's time. I was like, okay.
Here's how I think it. Let me know if you agree.
And this is a whole other concept, which is
the best way to get feedback from people is not by asking what they think, but to put something concrete in front of them.
And then have them react to it, right? It's a two and fork.
And so my description is
PM should be doing everything in their power to draw the perimeter.
Of the space, of the problem space.
And it's within that.
Engine design, everyone else that you're working with.
They can go as crazy as they want, push up against the bounds and it fill the box to its maximum capacity.
But you've now applied the constraints that allow you to actually have productive conversations.
On the other end of the spectrum, though.
I think there's a lot of folks who think, Oh, PMs are just
Strategy
High in the clouds, all they do is, you know, kick things off.
You need to be
obsessed about the final deliverable.
and whether or not value is actually getting to the customer.
And I have like a really trite example of this, if you want to go down it.
But please.
The the key point I want to make is
I think it is.
Tempting.
When we think about
Engineering, product and design.
to draw these really clear swim lanes and say you do X, I do Y.
Don't tread on you know, my area.
Five.
You need these murky overlaps in order to build something really good.
And so
Even if
The engineers are gonna build a better product than you and the designers are gonna design something better than you.
You need to come with a strong opinion and you need to do the legwork.
To get their trust.
So they actually care about your opinion in the first place.
Okay.
Time for mini story.
Uh so square we're building a point of sale for restaurants and
If you've ever seen one of these in a restaurant, there's this sort of
grid of tiles that they tap.
to enter your order when you're sitting down for dinner.
And we were developing one.
And there's
This concept of a
Like a menu group.
So it's a little box, you tap on it.
And then it pops the screen in, so you go to the next level of like the hierarchy.
So example would be you have a wine button.
You tap it.
And you see your reds, whites, et cetera.
If you think about the people that we were trying to serve, there's
the restaurants that were coming from a really old legacy system.
And if you've seen a bartender tap on one of these, I mean it is
muscle memory to the max. They're not even looking at the thing and just punching in the order.
Blindfolded.
It's
Rapid fast.
On the other hand,
You have
people who are entering the workforce for the first time. They've never used the point of sale.
And so we have to serve
Both of these equally well. How do you deal with that level of speed?
But also
ease of use that anyone can learn it for the first time.
And so there was this interaction that we really cared about, which was
When you tap on a menu group.
What's the animation?
To pop you.
into that next level. This seems like such a small thing.
But it made the difference in how easy it was to adopt for a lot of the restaurants.
And so
A designering myself spent
Like literally an entire week.
Just fine tuning how many milliseconds it would take.
To pop.
In and out.
So that I thought right. And we actually brought in
Servers and bartenders to play with the prototypes we had on iPads.
And be like, here's an order, pop it in.
And we would see where they would sort of like
Flinch or hesitate?
because the animation was too slow and they thought I can't tap it yet.
Or something related to that. And so
It's easy, I think, for a PM to say
That's not my responsibility. I define the requirements.
Yeah.
Have a menu group.
That goes to the next level.
Designer engineer figure it out.
No way.
Like that's fully on you and you better be involved with those details.
I love this. And there's there's two directions I wanna go.
So there's the drawing the perimeter and then there's this paying attention to the final deliverable.
Keeping the barley high.
Which I love and I totally agree with both.
Uh, in terms of this animation.
People hearing this.
But our PMs are gonna be like How do you how do you have time to spend a week?
on an animation.
For one little product. I have so much to do. I gotta hit some goals, drive some numbers, I have people waiting for me.
Uh maybe because Square is like this
once you deploy it's harder to change and it's like a big
Deal.
To ship.
But
I'm curious if you have any advice or things you've learned about how to create space for that sort of thing to create a
Time to spend a week.
on this animation, or is it just was it just like obvious to everyone, we need to spend as much time as we can?
Top down, everyone knew.
I definitely don't think it was obvious to everyone.
And I can
I can definitely say that because you know, we were given a pretty strict deadline that we needed to launch by.
And
I pushed it out.
Three times.
Mm-hmm.
And that's not because of this one animation, but it's because of a series of decisions where we said
This is what we believe we need to ship.
And this matters much more.
than hitting some artificial external GA date.
And
There's this other aspect that I think
PMs like to
Feel good about how busy they are and like
I'm involved in so many processes and I have to talk to this person, talk to that person.
All that might be true.
But I think there needs to be
A
Calibration.
Well at least
Like a spring cleaning of
What's everything I'm doing and
How much do these things actually matter?
to getting value to a customer.
'Cause as a company gets bigger, as teams get more complex
it's very easy and natural to spend more time on things that
Error
Internally focused and not externally focused.
And I think we just all have to have like hyper sensitive antenna to that.
So that we don't fall prey to
Well
The way that my job is described is to do these things, but
Really? It's
The outcome again of
Put something in a customer's hands, it solves a problem and it's amazing.
Reminds me of your uh now colleague Jeff Weinstein's
Uh
Advice he got from
One of the Callsons.
Where they came to him and they're like
You're world class at doing the second and third most important things.
And you're not focusing on
the most important thing because it's so hard and that's something you need to work on.
Totally.
I will say so one on that.
Uh the CEO at Mutiny, Charlie, she always repeated to me nonstop.
Keep the main thing the main thing.
And would just say it ad nauseum.
And I'm really glad that she did.
The one
excuse I don't want to give folks.
Is
As you
Progress in your career.
You have to
walk and chew gum at the same time.
You can't say.
Oh, I'm only focused on this thing over here. So
Other folks handle that.
Like you do have to figure out how to do a little bit more at the same time.
Pine.
Priorization does.
Play a factor.
There's a framework Shreyas uh suggested that I really like the L and O framework. I forget exactly what the L and O stands for, but
Leverage
Something, something, and we'll link to it in the show notes that gives you some advice on how to
prioritize your time based on the stuff.
Totally.
Okay, so so I guess in the case of pushing back to create space, this was just you as a product leader recognizing this is really important to get right.
I will
Convince people we need to
Make more time for that.
I don't want to make it seem like
It was me against
Everyone'cause that was definitely not the case.
I think the the starting engineers and designers on that team
really cared about the quality of what they built too.
That's a a pretty structural sort of DNA for a team as well.
If you don't start with that.
And
As a comparison, you have a team that
is that really prides themselves on
Shipping
fast and meeting deadlines really prescriptively.
You might end up in a different world or
your role as a PM might be a little bit more challenging if you want to push on this stuff?
So I do think you have to
take into account like what is the DNA of the team.
And then can you exploit that, which I was able to do.
Or
Do you actually have some change management to put into effect if you believe that it's worthwhile?
Mm-hmm.
Let's go back to the perimeter drawing the perimeter concept.
To make that a little more real for people.
So advice here is the role of a PM kinda your main part of your main job.
Uh uh especially when it comes to engineers and designers to draw the perimeter.
For the team, can you make that a little more real? What's an example of that maybe from something you worked on? What does that look like?
Totally. The the best word to describe the perimeter is just constraints.
At the end of the day
You should be adding as many constraints as reasonable.
In order to
To let engineers and designers
come up with the most creative solutions.
for whatever you're trying to do. And so again, if we just like stay focused on this point of sale example.
One constraint would be
Who the hell are we serving?
Are we trying to go after sit down restaurants that are serving five different courses and have a two hundred item wine list?
Or are we trying to serve?
The taco truck.
Those will lead to very different spaces.
And if you leave
Both on the table.
the lack of that constraint makes designing a good solution.
That much harder.
Uh.
There are instances where you actually can't apply that many constraints.
But I bet that if you push on enough different axes
You eventually scop it down to a point.
Where
It feels really good for the team. And
It's just about how do you remove decisions, right?

This I think is like a maybe a trite phrase, but
The best decision is no decision. Like if you don't even have to think about the decision.
the team is that much more effective.
So to give people a few, maybe even pointers of I need to create more constraints maybe for my team to help them
go crazy but within this box that we all agree on.
So you mentioned there's make sure the user is clear of who you're designing for.
There anything else just like thinking about maybe the PRD someone's trying to write to help create this?
Constrain, what other maybe bullet points sections would you imagine or do you find
Useful to add.
So beyond
Customer segment slash like what their specific role is.
I think another one would be uh we can loosely call it jobs to be done, even though I know that's becoming an increasingly loaded term.
But
What's the thing they're trying to do?
And how many different pathways are you willing to entertain around it?
That's another one that I would think about.
Uh.
Depending on what you're building, there's
Availability. So do you care about
Desktop web, mobile web, native mobile, et cetera.
And maybe another one to think through just as an example.
Would be
This is probably getting closer to what a lot of
people think about in terms of principles.
But
What are the things that you want to be
known for.
When you ship a product.
And one example there might be speed.
And so if you say speed is more important.
Then
Consistency of data.
That's a huge trade off.
And constraint that you can give the team. Oh my God, if an engineer hears, I don't need
real time consistency of data.
I can do so much cool stuff.
And easily accomplish that speed thing.
And so that's just like a a very technical example, maybe.
Awesome. Okay. I'm glad I followed up on that.
There's a couple more things you mentioned that I want to
Come back to you real quick.
Uh the first is this tuning fork idea. I completely agree.
this point you made that the best way to get feedback from your team is
to take a first pass at it. And here's like a rough quick draft.
Uh
I find with design especially if you design something
Ugly.
Uh and designers are often like, Let me make that better. I can't stand this thing.
Uh is there any other anything else you want to add there just like
This idea that
Yeah, tuning fork as a feedback strategy.
Okay, there' there there's two areas we can go deeper on here.
One is in how you get the feedback.
So
This is definitely uh a squareism. I think it was probably adopted from Amazon.
Which is around
The silent read.
Of documents.
When
You are all so busy.
And someone's like, I wrote a doc. You send it into the Slack, you know, ecosystem and everyone goes
Please give feedback.
You have so much going on, like you'll you'll be lucky to maybe get a response. Maybe there's one or two people that chime in.
And so
Even though we hate meetings.
And we love asynchronous.
There is a lot of value to saying
I need
Twenty minutes of focus time.
to interrogate something that I've done.
And
We're not gonna talk.
I'm literally gonna
Force us into a room or zoom.
You're gonna read this doc. I'm gonna watch you comment on it in real time.
I'm gonna respond to your comments in real time.
And at the end of this thing, I'm gonna have enough really good input.
That I can do a huge rub on this thing.
And get to the next phase.
I love that. So it's basically instead of
Hey, I I'm sending you this doc to go review, give me feedback. It's
Uh, I'm gonna schedule a meeting and the meeting is for you to spend time reviewing this doc and giving me feedback, and then maybe we could talk about it.
Yep.
Yeah, yeah.
A lot of people are gonna hate
hearing that'cause like Oh my God, I have so many meetings already. Why do I want another meeting that isn't even a meeting?
But that's the best kind then.
Because it's
actual work getting done.
Right.
And maybe you carve out two minutes at the end for one really immediate discussion topic or something.
But I don't
Think
We give enough space.
In any type of meeting.
For people to actually think.
And when you are just staring at a doc, you know, with your camera off and the only expectation is to engage with that thing.
Thoughts are a little bit more.
Better and crisper.
And I think with this idea, like if someone says I want a meeting where you just sit and review this doc, you could always say
Let me just review it asynchronously. I'll give you feedback, I promise. Give me give me twenty four hours.
Right. It's not like they have to come to this meeting.
Although I would urge you to make them come to the meeting. Okay. Say more there.
Because you find that that's a lot more effective.
I think there there's two sneaky things hiding behind that. One is the yeah, I'll get to this in the next twenty four hours.
Maybe they don't.
Like I maybe you'd really trust that person and they're the exception.
But
Beyond that, there is something else.
to the real time interaction that can happen.
when you're commenting and responding on a doc at the same time. I think this is the part that often gets lost, which is
The the latency
Between
A comment or question and a quick follow up from the author.
Just
pushes that cycle speed.
Really long.
in a way that doesn't need to be. And so when people are trying to find like how do you move faster, like this actually is
One of those
Very good examples.
Uh moving slower to the faster.
Uh reminds me of Claire Vaux, I think it was her
Phrase of uh
moving one clock speed faster and just like that's of the way you speed up a company's
try to move one clock speed faster, which in this case is just like
reduce the time between feedback.
And iteration.
I love it.
Okay.
I wanna shift to talking about some a few very tactical
Things that you've found really helpful in your
PM career and something you recommend?
To other product teams.
The first is uh something you call the decis decision log.
Uh you
think every PM should keep a decision log. Talk about what that is and why that's powerful.
I will say there's sort of
Two different decision logs we could talk about. We'll focus on the former though.
The latter is just
As you're making decisions within your job, you should
document those, you know, within a PRD.
Make sure everyone knows.
It's just a silly, very small thing, but I think every PM should do it.
The
other decision log though that I think is quite critical.
Is
If we
Zoom out for a second.
Every
Person.
has something that they can do.
to slightly increment.
in their craft.
And you know.
Sprinters have certain exercises that they do. I there's something beautiful about
Pianists and piano scales.
where it doesn't matter if you are just learning the piano or you are a
thirty year veteran.
Like
You're still doing your scales.
And it's because it lays the foundation for everything else that you need to do.
And so
We all talk about product sense. It's this like super mystical thing that no one knows how to get better at.
To me, it's just a fancy way of saying
You can make good decisions with insufficient data.
And
The core of that.
is decisions.
And so
PMs need as many reps as possible.
In making decisions.
documenting the rationale behind those decisions.
And then
Crucially.
Seeing the outcome of them.
And so
The natural follow up would be
Well, I only have to make X decisions in my job. How the hell do I make more of them?
Look around you.
There's other teams that are making decisions. What would you do if you were in that position with the information you have? Great. Write it down, say why.
There's other companies.
That are doing crazy things.
What are they doing? What would you do if you were responsible for the roadmap? Write it down.
A year later, see what they've shipped.
Like you can just do this for anyone. It's free.
And
No one
Takes the time to do it. But that's how I think you get better.
And actually making decisions. It's just
Doing more of them.
Hearing you describe this, it feels like obviously th yes, we
Why aren't we doing this? Like how else can we get better?
If we're not reflecting back on the decisions we've made.
And
Realizing hey, I was I made a bunch of bad decisions, but I'm s always so confident my decisions still.
Maybe shouldn't be.
So
I guess first of all, do you actually do this? How often do you do this? And
Is there an example of
you learning something from your own decision lock.
Many.
Uh and many of them
Because it was a wrong decision.
But yes, I do keep a decision log. Uh I have a separate sort of practice where it's just a daily log.
Which is everyone wants like the perfect note taking system. To me, the best note taking system is inspired by uh what is it called?
Like
Big ass text file B A T F. There's a funny blog post from like two thousand one on it.
But it's just
You write everything that happens to you in a day in a bolded list.
And it's all on one big note.
And that way you can, you know, command F it, do whatever you want.
The way that I keep track of it is I do a little like hashtag decision and then
Write things down just as I think about them.
And then I'll have a reminder to sort of comb back through on some cadence.
And so uh
I'll first use a positive example, which is a funny one. So if we rewind
to I don't even know what year, but Shopify had
Uh just launched.
Shop app.
their consumer application for
What started as uh tracking your order.
When you bought something from a Shopify customer?
And then it's evolved into a full blown like Amazon competitor, right? You can actually like find merchants and buy things through it.
When they first launched it though.
Uh I was like Oh my God.
This is so brilliant.
Like they have completely
Hijacked.
This specific loop for consumer buying behavior.
via this very unassuming thing, which is package tracking.
And so like that morning I was like, You know what, whatever, I'm gonna
quickly draw a diagram of this flywheel that I think Amazon owns today.
I'm gonna show how Shopify is like slowly
planting their little seed to take over this.
And how Shop App fits into it.
I tweeted out and then I don't know, that day there must have been like
Sixty Shopify employees that followed me or was like
What the hell is this guy talking about?
And so
Funny enough, fast forward, I've talked to some of the folks that worked on it and they're like, Yeah.
Nailed it.
Here's what we were thinking, here's why, you know, it's no longer secret sauce.
But
That was a really interesting example of both
Doing a decision log.
Putting my rationale down on paper, in this case broadcasting it out.
But then having that be a mechanism for it making its way back to me to actually better understand.
Why did they make the decision versus what I thought.
Because the reasons were a little bit different.
Uh but
The outcome was the same.
So that's like one interesting example.
It's an amazing story.
You doing this explains why you've been so successful. I can see how this all connects now.
I think for a lot of people
they want they would want to build this habit. Like clearly there's a lot of value here, but they just
don't because you know, they got a lot of other things going on.
Or that's just like, you know, it's like this new thing they have to start doing.
Is there anything that helped you
adopt this practice of this daily log.
slash decision log that you think might be helpful to folks to motivate them to
Give this a shot.
This is probably just
general
advice on building any habit, which is
Start small and
Just
Force yourself to do it.
And uh there's like that old saying around
How do you start running?
As a hobby.
You don't do it by saying, I'm gonna run a mile every day.
You do it by putting your sneakers.
at the foot of your bed.
Take your shoes off inside then you put it at the front door, like you have your shorts ready to go.
You're like, I commit.
To putting on my shorts.
And if I decide after getting dressed to go run
That I still don't want to go run?
Okay, fine.
But like you build up to that thing. And I think decision logs are the lightest weight thing possible.
And so you can start super easy by saying, You know what?
Every Sunday morning.
I'm gonna scroll through Twitter, I'm gonna check out hacker news, whatever it is.
I'm gonna see something interesting.
And I'm gonna make a bet. I'm gonna
Place my decision on this thing.
Write it down and then set a counter invite.
in you know X weeks, X months.

Plays out.
And that's all it is, right?
Ten minutes once a week.
Super easy. And then over time you can crank it up.
And then eventually you're just like constantly writing these decisions down.
And then it's like
feeding its way back into you, it becomes second nature.
And you're touching on something that uh
There's been a
little bit of talk on his podcast and newsletter post about this idea of to get better product.
sense and product taste and also just like
Decision making this case.
One of the best strategies is to simulate other
people's decisions and simulate what they're thinking through and predict what they're gonna do.
Which is what you're describing here.
Totally.
I
I do want to apply a pretty severe caveat here though, which is
A decision log is not a replacement.
for building products. Like it's a
Additional.
complimentary thing that you could be doing on your own.
But if you think that you can just, you know, sit back in your chair
look out at the market, make a bunch of calls and be like, look at how smart I'm getting without actually being hands on with
Like building a product.
You're not actually gonna get any better.
So I just want to interject that.
Amazing caveat, very important. Don't just sit and read Hacker News and think you're gonna become an amazing
Founder or product leader.
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If someone wants to try this idea of a daily log, what do you what is it exactly, say decision log or daily log? Is there like is it just
Things that happen today and then hashtag
Here's a decision I made, or here's a decision I think Shopify will make in the future. Is that the format?
Yeah, it depends on how far you want to go down productivity and note taking uh sort of rabbit holes, but
Well let's start basic. This is not what I do, but I think it's the easiest place to start.
Spin up a Google Doc or an Ocean page.
Just call it daily log.
And then
bullet point out like the date of today.
And then as you're going through your day, you have a meeting, just type in the meeting name. If there's a takeaway, put it under there.
If there's a decision you can make
Do hashtag decision and in this case say
Shopify launch shop app.
I think this is their way to take over, yeah, like
The fulfillment
to
Buying behavior loop.
The reason for that
Is XYZ.
follow up on this in six months and then set your calendar invite.
Awesome. So as motivation for listeners to try this sort of thing.
Just look at the success Kevin has had as in in his career and how insightful
he has been so far and will continue to be, and this is how these happen. This is how your mind learns to
see things in a really unique, interesting way. So I know I I know you're
modest and aren't gonna take any credit, but I'm just saying this is how you
This is how you get better is trying stuff like this.
Footnote.
Correlation versus causation. It's all put out there.
Could be all genes, could be completely unrelated to anything you've done your entire life.
Uh I think it's like me being very lucky. I'll I'll put that out there.
Uh okay, so something I wanted to touch on with this decision log idea and it's a segue to talking about hiring.
Yeah, I think
Interviewing is also a really good opportunity to try some like this.

They think they know what they're looking for. They think they've made all these decisions. They think they have these amazing interview questions that are gonna signal
help them see really good signal. But you never actually go back and see, was I right?
Should we have hired that person? Did this person work out?
Was that question asked them at all in form?
was all at all a a leading indicator of anything.
And I feel like this is a really good method for
Improving your interviewing.
abilities is like
Here's the questions asked.
Here's what I think and then a year later look back.
Well then I'll go. I think
Some of the best companies actually do have a practice around this.
Where
Yeah, they had a six, twelve, eighteen month check in on new hires.
And they then compare
Yeah, they're sort of
Performance against level higher that.
And then review against the scorecards.
Uh
It's like a pretty laborious process. So
you know, startups aren't probably gonna do it in the same amount of rigor.
But
Yeah.
Shows you.
So much about the holes in your interviewing process.
Uh, so I I definitely close one of that one.
I love that. Oh my God. That puts all this pressure on your score.
Which is great.
So let's actually segue talking about hiring. There's a couple more tactics that I've seen you be really good at. So one is just hiring in general. You have a lot of interesting approaches to hiring, including this idea of a
Unsell email where you try to convince someone not to join your company?
Talk about that and why you think that's effective, and then anything else along the lines of hiring you learn.
I'll say the idea of the on sale email came from a
Place of failure.
Which is
Uh at Square I had sort of
shifted into a position where I had to hire a lot of people really quickly.
And
Through that as a you know, if you're the new hiring manager, you're like, All right, great.
The goal I've been told
The goal is to hire fast.
Okay, you give me a metric, you're gonna go after it. So you do your best
to get as many people in the door as possible.
And
When you're talking to your recruiting partner
They're incentivized to increase pass through rates, offer to close rates, all these other things and stuff they're like.
Yeah, and this person's really good. And you listen, you're like, Yeah, they are pretty good, aren't they? Even though there's a sneaking suspicion.
Then maybe they're not the right bit.
But you move forward anyways.
So fast forward.
There's a few folks I bring on
And within
Six months.
They come to me and they're like, This is not at all.
what I thought I was gonna do. This is not the environment I thought I was gonna walk into. You didn't warn me about this, that, and the other.
I feel terrible.
How do I prevent this?
And the reason it's bad is not just because they feel surprised, but because then
Either one, they decide to leave.
Two, they're not performing because it's not the right role or environment for them.
Or three, you know, maybe the company is still good.
But that rule isn't
And so they immediately try to do like internal mobility or something to another team.
Which then leaves you with the same hole.
So
All of those bad outcomes.
So I'm like, how do I prevent this? Well
How do I I just gotta front load.
all the gnarly stuff they're gonna find out in their first six months.
And so
The practice I started developing is you go through the whole interview process and during that period
You're collecting all these little concerns.
Fears, anxieties that
They're not explicitly saying, but they're definitely hinting at.
And you gotta be pretty
Honest with yourself about which ones are real.
But then when you get to offer stage.
I send an email with no more than eight bullet points.
And I say
all the terrible things that are probably going to reinforce their fears.
And I I'm pretty tantid about
This is what it's like here.
Uh maybe one example would be
Hey, I'm
Apparent.
And
I'm worried about work life balance.
Maybe they don't say that explicitly in the interview process.
But you get a feeling for it. And I I get that as a parent too, right?
So
If I'm at a startup.
I'll be really clear and I'll say, you know what?
We are a series A startup.
We are
pushing really hard at product market fit.
The expectation here.
Is gonna be
That you're online.
At ten.
that you can occasionally hop on a meeting on a Saturday or Sunday.
And if you can tell them that
Up front.
And they can read that whole email and still be equally excited to join.
You found yourself any plus higher.
But if they would be that and they're like
I don't know anymore.
It's way better to say great.
This is not a good fit.
Let's go our separate ways.
Then have them leave after six months.
And when I first instituted this
I lost
thirty percent of candidates at offer stage. Oh wow. Which drove my recruiting partners insane because they look terrible.
Their manager's like, What the hell are you doing? You're losing everyone at the very end. And so they ask
Can you either not send this thing?
Or
Can you send it at the very beginning?
And my answer's no,'cause I don't know what they're afraid of yet.
I have to
go through the whole process to actually understand.
the thing that's going to potentially make them say no.
And that's really crucial, I think.
But once you hear it again, this is like such an obviously good idea.
Uh
Clearly not an easy thing to do.
In this case where
recruiters were upset. Is it just get buy in from folks above, like okay, we all
This sucks for them, but
At a macro level, this is good for the business. And they're like, All right, let's keep doing it.
At Square at least when I first started doing it. Luckily I had a very good relationship with them. So
That's a that's a good starting point.
Uh
This is maybe gonna come across a little bit.
Flippant, but
They can't stop you from sending an email.
Technically.
So I'm just gonna send the email.
And if someone really wants to come
And say
This is bad for business, whatever it is.
Like I have
very strong reasons for why that's not the case.
And now I've done it so many times at least that I can point
To very clear proof points.
Uh on why this is the right path.
And in theory, the incentives would be a line where the recruiter
success matters is based on like did they actually have a good time? Did they stay? Did they um have good impact? But totally since they're not, obviously their incentives aren't right.
I I think some companies have shifted on that where uh
Recruiters and and sort of salespeople are
compensated sometimes in similar ways on terms of like quota and whatnot.
And so they'll hold the recruiter accountable to
Yeah, six, twelve
Post offer tenure.
before they say, Oh yeah, you successfully landed.
This role.
Um so you can tweak the incentive structure a little bit, but not everyone does that.
Okay, so the advice here is uh
to end up with better people that end up being successful and happy.
put together, like keep track of the things that will probably
Be painful for them at the company.
And then
craft an email that shares up front.
Here's what may be a problem.
If you join and I just want to be very upfront about it. Is there I think you actually sent a share template of one of these emails in one of your blog posts?
Yep, that's right. I have like
A fairly real one.
You're right.
Is there anything else?
hiring wise, I know there's probably infinite things that you've done, but is there anything else that you think maybe worth sharing of things you've
learn to be more successful at hiring awesome people.
One final note I'll make on Unsell email is
It's not as if you just send the email and then they either say yes or no. Like
Most of the time they will say
Thank you.
I am cool with six of these.
This one freaks me out. Can we talk more?
Definitely.
And I think this is where
Hiring managers have an incredible responsibility.
that sometimes isn't taken as seriously as it should.
Which is when you are working with someone to get them
To join or to offer.
You need to bend.
to do whatever it takes for them.
And so if they're like, Hey, the only time I can talk is tonight at eleven o'clock after my kids go to bed.
No problem. Here's my phone number. Let's hop on. I will walk you through whatever you want to talk about.
And that sort of has to be
The place you get to?
for like really strong hires. So that's just like one other thing I'll say.
The meta point around that.
Is
You need to be
really investing in the candidates. This probably does change at a certain scale, like
You know, if your quote unquote organization is hiring
A hundred engineers or whatever, like you have process around it, you have pipelines, it's a machine at that point.
But
I do think the direct hiring managers
Have a responsibility.
To be really involved in every individual.
'Cause there's no one who's like
directly hiring a hundred people, it's always within a number that I think
You can take on.
Okay, so this is the final tactic that I heard you're amazing at, which is automating user research.
On the surface, that sounds amazing. I'm gonna automate my user research. It's gonna be amazing. So great.
Talk about why you find this really powerful and important. And then how do you actually do this? How do you automate user research? How have you done this on your teams?
Let's start from why this even matters.
I think a lot of folks going back to
What is the point of product management? I think there's a a similar overlap with UXR, like user experience research.
And people will say, Well
If they're doing research.
W what do I need to do? I should just be consuming what they're producing.
To hell with that.
Like
I no PM should settle for looking through bent glass, in my opinion.
Because whether it's a research report
Whether it's something a salesperson is telling you
Whether it's market research.
Don't care.
It's been processed.
By someone.
And PMs need direct exposure to raw material.
End of story.
And so that's where I think like you just need to constantly be talking to or interacting with whoever is is your customer.
That's like the foundation.
So okay, if we all agree on that.
Then the question is
Well, I don't have time.
It's so hard.
How do I find them?
my customer success manager says I can't talk to the client
If you are in a situation
where the product manager is literally not allowed to talk to a customer.
There is something structurally wrong.
And that needs to be fixed first. So I'm gonna ignore
That one for now, just'cause that's a whole other sort of rabbit hole.
But
You need to fix that in order to even get close to the next thing.
So okay now.
The excuse is gonna be, Well I don't have time.
I don't wanna run a program. I don't wanna have to, you know
query and look up and send out emails every week.
There's so many good resources out there right now.
And I think that there are I'll I'll speak mainly from like a B to B sense.
I think B to C slightly different story. I don't have as much experience there.
B to B.
The the two things I will say.
One is there's this thing called userinterviews.com. Shout out to them.
They're pretty much user testing, but
Like explicitly focused on P to P.
And you can put in super clear criteria on the type of people you want to talk to.
They do the heavy lifting and sourcing it.
And then you just review and say yes, yes, no, no.
And you can have a stay stream of the exact ICP you want to go after. Um ICP is ideal customer profile.
That you want to go after.
Just coming to you automatically.
Amazing.
The next one though.
Uh
It depends on whether or not you have this tooling in place, but
The broader theme behind this next category is
Your sales team is a research team.
And if you don't view them that way, you are missing out on half the value.
And so there's tools like
Gong, which do you call recordings?
And you can set up filters and alerts.
For specific terms, phrases, competitors, whatever you want.
I don't care what PM you are in a team, like you can find the terms that are associated with what you care about the most.
Those then get pushed automatically.
to
A slack channel or otherwise.
And then you can set up
workflows, either via Zappi or something else, to say
Who was the customer, pull their email.
Put that into a sequence.
Drop in my cow and leave.
And you just have interviews showing up.
automatically on your calendar.
I will say I cannot take credit for this.
Shout out to Beth Hills, uh, who was a PM that I hired in Mutiny.
She is the
Queen of automating customer research.
And like
built an a amazing system around this.
So the way it works is you set a term for like uh I don't know, uh
P O S point of Sale
Something in
Kong.
And if somebody says that or has an issue there.
Talk about again how that
Schedules a meeting with you potentially.
Yes. So
Yeah.
Gong has an integration with Slack.
You set up this alert, it posts to Slack the excerpt of the transcript where it was mentioned.
Along with the user or customer name. So in this case it'll be
You know.
Lenny's burger shop.
Uh Lenny's Burg Lenny at Lennysburgershop dot com.
And then you can set up a zap year to take every new Slack post from that.
And then send
Uh using I don't know.
Customer IO.
An email.
to that person using that field.
And then in that template of the email drop in your Calendly specifically for user research.
Wow.
That is genius.
Uh I love that.
It there's another similar tactic that Teresa Torres shared on the podcast, one of the earlier episodes, where you have a little pop up on your home page.
Asking people, hey do you wanna
You wanna talk? We'd love to hear feedback on our product.
Click here if you wanna uh
Give us some feedback and then that schedules account only on the PMs.
Totally.
So you mentioned gong.
Customer IO, there's like some tools here. Is there anything else he thinks that Zapier, obviously?
Uh, is there anything else you find useful to help automate this sort of stuff?
If I take a step back from the automation side.
Uh or maybe like
Straddle it.
Depending on the type of business you're in.
There's
Ideally people talking about you.
Somewhere.
Right. It's either happening on Reddit.
Or Twitter.
Or on some forum or your support forum.
Th there is a
community. There's a destination somewhere. And if there isn't then
I don't know, that's too bad. Maybe you don't have product market that.
Okay.
If you can take advantage of that, you can usually set up something.
And if it's not
A gong or a zapir.
Maybe it needs to be just like a custom script that you write or you sit down with an engineer to say, like
How do we set up alerting around this thing?
So that I know when things are happening.
And I think you can't use
The effort required to do that as an excuse.
to not be talking to your customers more frequently.
Because again if we go back to
A product manager should be trying to like convert this potential into kinetic energy.
part of that understanding and part of knowing the constraints you can apply.
It's just living in that world.
As much as possible.
Uh like the best comparison I can give is
There is a world of difference between
Reading a report.
About a lime cook.
And then standing.
with a line cook.
You will just pick up on so many ancillary aspects of what their life is like.
that cannot possibly be communicated.
in like a report.
And you owe it to yourself as a PM to be exposed to those things.
All the time.
In my experience, every time I talk to
A customer.
I'm always reminded why have I not been doing this more? Like
How can I not be doing this? It's absurd that I haven't done this. Like every time you actually do it. But until you
Do that. You're like, No, no, I g I g I know what they want.
I'm reading all the
Customer service channel issues I'm reading there.
Email I was like I get it.
Until you actually talk to them, you're like, Oh wow, I had no idea.
And I love that your advice is like
The the tactics you're sharing aren't
Here's how you get a bunch of feedback.
From your users, it's like here's how you actually get to talk to the right users. It's like in the end of the funnel, it's your talking.
To a potential customer. It's not just reading a cool
Some feedback that they shared.
That's right.
And
I think.
Just like the the last point on this one is
When you join a new team
Or start a new role.
Every PM is like
budding with energy to do this. Like of course I'm gonna talk to my users.
But then you reach a point where you go
No, I know them.
Inside and out.
I don't need to talk to them anymore.
I can write a PRD in my sleep and I'm so busy
Doing both, you know.
product improvements, maintenance, annual planning, something else.
I
I can use my intuition.
From the hundred interviews I've already done.
I don't need to do one more interview.
And that is a very tempting lie to tell yourself.
Because the world is changing, their lives are changing.
And you need to constantly be exposed.
to those little micro changes in their lives in order to build the product that they'll eventually need.
The best explanation of
heard of this is actually from your new boss, Patrick Halson, boss's boss's boss. I don't know how far away you are from
Um
Where he talks about user research and where it fits in and the way he described it as
Instead of
Doing user research, talking to customers, informing what to build.
It's talking to user talking to customers informs your mental model of what the customer needs.
And then that informs what to build.
Hero percent.
Yeah.
Beautiful way to think about it.
Okay. So I'm gonna take us to a couple of recurring themes on this podcast, a couple of corners.
Of this mm room that we have.
Uh first of all I want to go to AI Corner.
So let's walk over there. Hello, AI corner.
I'm curious if you've
Found any interesting
Uses of AI.
In your work or in your life.
There's
Pleny in work. I don't know if any of them are interesting or novel. I feel like everyone's just like figuring it out in real time together. So
I'll should take us in a slightly different direction and this may be
Isn't directly useful.
To product managers.
But I think it's a really
Good story.
So
When
Mid journey V one.
was released, if we can remember that far back.
Mm-hmm.
It was at least
I got bid access on a Saturday.
And
For what's worth like I have three daughters, one of them's uh seven years old.
And so her and I were awake.
We were waiting for those two to wake up and I was like oh like
I have this cool new thing, do you want to play with me? And she goes
Course.
So we log in, we create an account.
And
I type in the first prompt.
Image gets generated.
It's like a rainbow or something.
And then I ask her, Do you want to try it?
goes of course. So she types in, you know, unicorn prancing in a field.
And it generates this.
Hideous.
looking like demented unicorn with two rear ends.
And like a demon flying over it.
And I'm appalled at first, thinking that she's gonna feel really bad about
What she
Got uh shown.
But instead I look over.
And
She's in awe.
She is amazed and then she turns to me and she goes
Did I draw that?
Like
Yeah.
I I guess you did.
And the thing that I got hung up on was that she used the word draw.
She didn't say.
Oh it didn't. Like.
I enter a prompt and the LLM produced this thing or like whatever weird terminology that all of us use.
It's like
Did I draw that?
And
I don't know when it clicked for me.
But at some point in time after that
I was like
The concept of these image generation models
Is the same as a crayon.
to her.
Like there is no difference in her mind.
And that is an insane change.
That I can't even comprehend.
And so
For me, that's just been I think uh
An experience that I go back to when I think about
People asking what do you think AI is gonna do and what's the next thing and is it chat or is it something else?
Like
I cannot comprehend.
What a child who grew up with a crayon of an LM.
Is gonna think.
is a good product in twenty years.
I need to start crying.
But
God damn it, like I have no freaking clue.
And so I think I have a cheat code actually as a parent because I get to see
How they evolve and use these tools in real time.
But
Yeah.
All I can say is uh
We are not even like beneath
The dust on the surface.
When it comes to
What's gonna change?
Wow, that is an amazing story. Give me tingles.
It makes me think a little bit about how like we used to code in
Binary and then like
Assembly and now it's
You know, Java and then I don't know.
All the languages, Python.
And now it's like it's like
Co like
A I L Ms generating code and it's the same thing for drawing potentially. These to be
Sticks in a
Cave and now and then became crayons and pens and
uh iPads and all that stuff, and now it's again LMs.
So that's pretty bonkers.
Amazing story. Thanks for sharing that. Uh useful to PMs and non PMs alike.
Okay, I'm gonna take you to another recurring corner.
Slash uh segment of the podcast fail corner.
Yeah.
I'm curious if there's a story of failure.
That
you can share of something that
Didn't go the way you wanted and
Still had it.
Positive impact in your
Life or career.
Well there's
Countless stories.

I'll I'll choose the one that I think
I've had to reference the most with people and w
has been to date.
The most difficult one.
to to really talk about it. I'm I'm on the other end of it and so now it's very easy.
But it took several years to get there.
So
Context.
Uh
Yeah, I meander my way to PM.
I land my first official by title.
PM job at a startup.
I made it. I I've arrived. I'm officially a product manager.
And
We go up, we go down, all the things happen.
Fast forward, the company is really struggling.
And so
We go through a series of rolling layoffs.
And I'm round four or something.
And
At that point in time, my wife was nine months pregnant.
With our first child.
And so
I am freaking out.
There is the peripheral side that I'm worried about.
But then there's also my identity.
that has been completely crushed.
Because
In the moment all I could think was
I thought I was a product manager.
This is evidence.
I am not.
And
I can't
I couldn't get past that.
And so
For what's worth, uh this is the
One
post I have on my website that
I I actually feel like
really, really proud of. It's called Finding Swagger. I can talk about why it's titled that way.
But
It's the thing that
I really wrote more for myself.
Because
It's a good reminder to me every time I fall into this mentality again.
Because
That may have been the first time.
That I really
had the feelings of
I'm not worth it or
I'm not meant to be this person.
But it's recurred you know several times since then over the past decade.
And
When I read back through
my mentality of how I got to the other end of it.
Yeah.
helps even myself.
Sure.
Get back on the horse. So okay.
I get laid off.
I'm distraught.
I have no purpose, I'm nothing.
And it was through a lot of reflection, a lot of conversation with friends.
And my wife.
Where
You eventually need
To convince yourself.
That
There is a difference between you not being good at something and
Mm.
business or company not needing that thing.
At a particular moment in time.
Or
You being very good at something.
But not in the way that a company needs.
And so
I think once I was able to get to that.
Square for me was the immediate subsequent.
role that I took on.
And I went into that thing.
Just
Full steam ahead. I'm gonna prove myself.
Like I know I'm good. There's a thing I'm good.
And I'm going to prove the hell out of that. Mainly to myself, but ideally to other people too.
And
I think
Yeah, you shouldn't do things for other people for validation, but
The
Initial success.
I got to see and like launching a product, gaining the trust of my peers.
uh having something that restaurants were texting me about saying
I can start my restaurant because of this.
I didn't go down during rush hour because of this, like
That gave me the validation to say, Okay, I am
Competent.
at this thing called product management.
And then from there you can continue to build and continue to grow.
But I think right now like
The market's weird.
The market's wonky. There's a lot of really good talent.
That is just getting
Head over sideways.
And
I have a lot of friends that are having the same
mental conversations.
Around
Oh.
I guess I'm just not worth it. I guess I wasn't cut out actually.
to do this job, do this role.
Be of this purpose.
In some cases maybe that's true and you can sort of have a a career transition or a pivot in your life, but
I think it's worthwhile to reflect on
What are the things that were in your control that you can now change moving forward?
And then what are the things that we're
Truly out of your control.
That you can now apply
to find a better fit.
And that's one of the
Big things that I've been able to I think
come around to and it it's really hard because
Early on, I think it's very tempting.
You
Associate a lot of different things with your identity or like
I'm a startup guy. I'm a PM. I'm a you know
fast whatever th I'm like a fast thinker.
And
When an event happens that
Pokes at that part of your identity.
The rest of it crumbles.
And so
Long story short.
Yeah.
I think it's really important.
For folks
To
Use these moments where it feels bad and feels like a failure.
To re evaluate.
What parts are actually part of your identity?
And which parts are in your control to change in whatever you do next.
Wow, what an important and great story.
There's a l as you mentioned, a lot of people are dealing with
Finding it hard to find a new gig.
And a bunch of layoffs. And I think this is gonna help a lot of people. The two categories you shared I think are especially powerful. So
The advice here is just
Separate.
This company
Just doesn't need
Someone with my skills right now.
From I am not good at these skills.
Can you just s share those two kind of things that might be true that you may not be recognizing about why you may maybe laid you off again?
Totally. So one is the business just doesn't have a need for you, you know, they got ahead of their skis and
That's their fault.
And
They probably admit that, but that's not up to you.
The second one though is
My skills and the way that company operates.
are not compatible.
And this one I think is really, really important because I've seen so many times.
Where there's been a PM engineer designer, like w whatever role.

Cannot make it work.
At Company A.
And then you
See them five years later.
Just killing it.
In company B. And you're like
Did they change as a person?
Did they get super good at what they were bad at before?
Like
Maybe a little bit, but honestly it was just a change in environment.
And when you find the right environment in the right role.
You just flourish.
And I think this is actually sorry, we'll go back to hiring for just a moment.
Uh or at least management.
This is why
Performance conversations can always
Feel so difficult.
Because
It seems like you're telling someone you are bad.
And as the recipient you're like I am bad
And no one wants to hear that.
But
The reality is
You are not bad.
It is that
maybe the way that your environment is working, like the machine that you exist as a part of.
Is not the kind that you thrive in.
And so it's
Within your control

I'm going to change.
How I work to fit that environment.
Or
I'm gonna find a different environment.
That actually fits the way I work much better.
And that's empowering.
I think that also applies a lot to interviewing. A lot of times you interview, don't get the job.
Any
Exactly feel like oh I'm just not good enough.
But really that company's way of working just may not gel with the way you operate. Like Uber.
operates very differently from Airbnb, operates very differently from Google.
And so it's not that necessarily something you're doing wrong. It's they just don't think you're fit.
And this connects to something I just had another guest on the podcast. He was um
Brain science.
Dude.
And he talks about how every company has this kind of habitat.
Like what habitat are you creating for your comp for your employees?
to enable them to think differently to or to be shut down and not feel like they can be creative or try big things or not.
And um
Basically the way just kind of to leverage that metaphor.
Like you may be a palm tree and you're trying to
uh join Antarctica and it's not you're not gonna it's not gonna go well.
Totally.
You gotta find Pump Springs or
Or some hard place.
Kevin, this has been amazing. Okay. So before we get to our very exciting lightning round, is there anything else that you think is important or valuable to share, leave listeners with, and if not,
Absolutely.
I think we'll probably
find ourselves on interesting detours to the Lightning Round, so let's roll in.
Kevin, with that we reached our very exciting lightning round. Are you ready?
Oh yeah, let's do it.
Let's do it.
Question one, what are two or three books that you've recommended most to other people?
I'll start by saying the type of book by volume that I read and get the most joy from are
Autobiographies and memoirs.
Uh.
It is just like
No.
Ultimate cheat code.
to spend time with people that you respect, are interested by, or want to learn from.
Oh.
Like could you imagine what it would take in real life
To sit down with
Albert Einstein.
Mm.
Fifty hours.
And just have him talk to you about his life. Like impossible.
But you can read.
And pretty much get the same thing.
So anyways.
Strong requirement or a strong suggestion, go read like autobiographies and memoirs of people that you respect.
Uh mostly for like their their mental model and way to approach thinking, less about, you know, specific things.
But
The one book
That I read without fail.
Every year.
Uh, has a very misleading title. It's called The Courage to Be Disliked.
I think it's been mentioned previously on the podcast. Yeah but
It uh it covers it's like a very Socratic method style, so it's about a philosopher and a young person.
And it tries to teach you the ways of Elyrian psychology, which is sort of like counter to Jungian theory.
The
The reason I really like it.
Is because it makes me uncomfortable.
So
The whole premise, in my opinion, behind
The book and and they're in psychology is
Focus on
What you control.
Like that's the one line.
Don't worry about
Everything else. Don't worry about what other people think. Don't worry about what other people do.
You cannot control those. You focus on yourself.
and you focus on the actions you can take.
And like be the person that you think will attract other people.
That you want to be around.
And
There's some like really pointed notes in there that I'm like, ah I don't
Fully agree with that one, but it always
Pushes me.
To question something.
About what I believe. And so
Uh in every like
physical copy of a book I have, I like write the date that I
Started reading it again.
And you know, the front inside cover of this book.
I think it's been
Seven or eight years at this point.
Um that read it.
Every single year.
Well
It's like a decision log in another context almost.
Yeah, a little bit.
I was saying the the other book I was gonna mention.
Uh is the paper menagerie.
This actually shout out to Sean Rose.
Or I've never met him.
But I really appreciate Sean. He was one of the early, if not first PMs of Slack.
Yeah, he used to be really sort of um
loud on Twitter in a very good way. And I think I learned a ton from stuff that he would post. But one of the things that he posted was this book.
And
It is just the most
Beautiful collection.
Of essays that span like
Sci fi and fantasy.
And so like if you're into that kind of stuff, if you like exhalation.
Then like
Paperminage array is even better.
Oh shit.
Guess I gotta add this book to my list. I do love Exhalation.
There you go.
Oh man, this job is tough. I get to learn all these amazing books and then I gotta
Read them, but I don't want
Mm.
Hard. Speaking of more time, uh next question. Do you have any favorite recent movies or T V shows?
That you really enjoyed.
There's less time for either these days. Uh
I will say
Not novel.
The bear holds a very special place in my heart right now, both because I worked in restaurants and I got to build for them. And so if I've
Seeing the details that they do.
Uh actually gives me a lot of anxiety, but I I really appreciate the craft they put into it.
The other show actually. This is I think this is the first time.
Physical one hundred.
So this is a Netflix show.
It's a Korean show.
About yeah, a hundred different
bodybuilders, athletes, what have you on who has like the
Oftalum physique or whatever.
I don't really care about that part. The two things I love about the show
Are one
It's
R
Ridiculous.
What people
are capable of, like you see what they can physically do and you're like, Oh my God.
That's amazing what they can put their minds to.
The other part though, and this is maybe a trend of
Korean shows that I've noticed is
The
Amount of respect they have.
In this competition.
Is
Or none.
Like you have this guy who is
Uh.
historically famous was the top champion in judo or something.
And you have all these other athletes that are
Fifteen, twenty years younger.
And they're like
Bowing and like just humble to compete against the guy.
I kinda wish that more American shows had like
that level of respect as opposed to just like trying to find the most conflict.
There's something that I really like about that.
That's beautiful. I've
started that show but I haven't continued it, so I'm gonna revisit it.
Cool. Do you have a favorite product that you've recently discovered that you really like?
We got a really old two thousand two Jeep to work on with my daughters.
Uh just like
A true junker.
And
As a result of that
uh, you know, we're repairing it, we're taking off the rust, replacing parts, and so there's these little magnetic trays.
That you can hold
Screws and nails and whatnot, so they don't go flying and rolling around everywhere.
It's
Stupidly useful.
When you're working on a car?
And the girls love it because they can use it for other things like collecting hair clips or whatever. So magnetic trays, shout out.
Uh and then selfishly I will say
Uh my buddy Arjun Mahanti has an app called Circuit.
If you search the app store for circuit like C I R C U I T.
Hit timer?
It's
Such a delightful little app that lets you track like
Tabata sets or whatever else to just get like a little lookout in.
Super cool. The man magnetic tray is not boring at all. That is extremely cool and it has a really cool story too.
Do you have favorite life motto?
They often come back to you and
Find useful, share with friends and family, and work your own life.
I think we've actually maybe touched on both of these. Um I'll cheat and I'll pull one from maybe each parent so that
In case they see this, they don't feel like I'm favoring one of them.
Mm.
So my mom's side.
I think something that she would always repeat to me growing up is
Everything happens for a reason.
And
I hated that growing up because she only said it when something bad would happen.
Yeah.
Something that happens because
Everything happens for a reason. And I'm like, No, it doesn't. Life just sucks.
And
To no surprise at this point in the conversation.
I've now grown to really, really appreciate that piece of advice.
Because
What it's actually trying to communicate is
When something happens.
Good or bad, frankly.
Don't dwell on it.
That's the past.
Focus on what you want to do.
And then just move towards that.
And then in most cases
you'll be able to look back in one, five, ten years.
And connect the dots in a way.
Where the story makes sense in your mind.
And so
Just having that shift in perspective.
I think it's helped me a lot to not overreact to
Anything that happens.
Anyway.
Um
So
That's one side.
And then on my dad's side.
So
The funny
Origins of this
Unsurprising to anyone with Asian parents.
I'm a
Spunky little seven year old. I come home with my math test one day. I got ninety seven percent. That's pretty good.
I go show it to my dad with
Beaming eyes and pride.
sort of stares down his nose at it, looks at me.
Where's my other three percent?
Yeah.
Okay.
Just like
Distraught.
And
I sulk away, I'm very sad, I study hard.
I do the next math test.
I get a hundred percent.
Yes.
All right.
Dad's approval, here we come.
I come flying back.
I put the test in his hands, he stares down his nose at it.
Looks at me.
With another three percent.
I'm so confused. I'm like, I got a hundred.
out of a hundred, I have no clue what you're talking about.
He just looks me dead in the eye.
And goes.
Who said a hundred is the most you can get?
At that age.
I literally had no clue he was talking about.
And
She had to reframe it for me in the moment around like, Well, was there extra credit?
Who set like can you just write your own problems to challenge yourself more?
Could you have given yourself another test?
And maybe the teacher won't give you credit.
But y you give yourself credit.
For doing additional work.
I think I carry that theme forward.
Where
There's this weird transition we all go through from childhood to adulthood.
Where we no longer receive homework.
We're responsible for defining the work that we do.
And
When you do that.
If all you do is
the minimum of what's to find the hundred percent.
of what your job requires.
You'll never grow.
And so it it's up to you to actually find what is the additional three percent. There's always
Three more percent.
So that's my dad's lesson.
Kevin, you're blowing my mind. There's so many great stories. You're just full of them.
Uh and I feel like this lesson also applies really well to product.
And building product and founding.
Companies. Just
Pushing pushing further than people expect and
Making it a lot um more delightful than
The minimum bar.
Final question. Speaking of things that maybe people don't expect.
and may not understand is possible.
Uh looking at you, nobody would have guessed that you're a competitive eater at some point in your life.
As a final question.
What the well tell us about this part of your life. What did you eat? How does this work?
Uh, how far did you get in this path?
It's probably misleading to say that I was like a true competitive beater. Like I wasn't on the circuit with uh
I always forget his name, but um Johnny Chestnut.
Oh yeah, chestnut.
Back in the day, that's like the OG competitor on the hot dogs were good, I guess. Right. Uh for me it was more eating challenges.
And so whenever I would travel, I would find like the local eating challenge, whether it was time based, volume based, something else, and just like
Try to see what I could push my body to do.
Uh I was blessed with a great metabolism, so I never really had to worry too much about anything else.
And the the origin, like the first moment of this was when I was
Fourteen.
My sister was going to college in Minnesota.
And there's this
Steakhouse up there called Manny's.
Uh, which is where like the Vikings frontline goes up to after every game.
And they have this ridiculous
Ninety seven ounce water house. I don't know how many pounds that is, but it's too much meat.
For a human to consume.
Oops.
Uh ninety seven ounces, yeah.
And so
I sit down.
I order it thinking this is gonna be great. They put it in front of me, it's a monster.
And
Forty you have to eat in under an hour.
And so forty five minutes into it.
Uh I'm uh
halfway through and about to die.
And
The the catch is if you finish it in under an hour.
You get it for free.
And so my dad
Again, leans in.
And goes, You can't afford
Not to finish this.
And so message receive, sir.
Hunker down, I plowed the other half in fifteen minutes.
Mm-hmm.
I then slept for I think three days afterwards.
But
After that I was like Oh my God.
If I could do that, what else could I do? And so
On a carried for I don't know, nearly a decade of
trying to do these interesting challenges.
Wow. I don't know how that's physically possible, but clearly you did it.
Kevin, this has been
wonderful. I think there's so many lessons here for people in so many ways, life and work and
Parenting.
Two final questions. Where can folks find you online if they wanna follow?
you and learn more from you over time and how can listeners be useful to you?
I'm on Twitter.
Uh Kevin Yen.
Uh
Technically I ha I'm on LinkedIn. I don't post it very often.
I probably should. I hear it's very good.
Um
But
That's where you can find me. I also have my my website. I don't write that often and
I don't have an RSS speed, which has always been on my backlog and I'm always too lazy to do.
But one day I will add it.
Uh.
One quick note I want to make.
On websites.
So
On one hand?
I'd love
all the different website builders that exist.
It's amazing what we've
sort of enabled anyone to be able to do.
There is something
Really special.
About having your corner of the internet.
that you built sort of hand by hand, line by line.
And so like my website is like

It's a GitHub. It's hosted on GitHub pages.
But it's just raw.
HTML CSS from nothing fancy.
And I get so much joy every year.
Just doing like a slight tweaker cleaning of it.
And so I really do recommend that
For anyone with the curiosity and the desire
to buy your domain, even if you're never gonna write anything on it, you're never gonna share it out. Just
Own a little piece of the internet.
It feels good.
I love that. I didn't know that about your website and I could see ya I could see it now as I go there, like it's dot HTML.
Which you don't see as much anymore.
Exactly. Um
And then
Yeah, I can listeners be useful to you.
This is gonna sound trite and it has nothing to do with
Product necessarily.
Just
Be kind.
Like make for a nicer world.
Right.
Say thank you a little bit more often, hold the door open a little more often, wave if you cut someone off in a car.
Uh.
I think there is
A temptation and incentive structure.
To create
Conflict intention.
And in most cases
the world will just benefit from a little bit more kindness.
What an incredibly beautiful way it ended, Kevin. This was so much fun. I'm so glad we did this.
Thank you so much for coming on.
Thank you for having me.
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