Lenny's Podcast: Product | Growth | Career: How to ask the right questions, project confidence, and win over skeptics | Paige Costello (Asana, Intercom, Intuit)

You're often the youngest person in the room.

What have you learned about how to garner trust

and win over skeptics?

The thing I would say is bring the insight.

Know thy customer, know thy market,

know thy competitors, know thy numbers, know thy product.

I'm curious what you find most holds back new PMs.

Your brain is so accustomed to having a scarcity mindset

as opposed to creating alternative options

or seeing a different path.

Effectively, there's this notion

of how might the opposite be true.

And the moment I challenged myself

and said, how might the opposite be true,

my shoulders dropped.

I felt more relaxed.

I was like, oh yeah, I can do both.

It'll be fine.

Welcome to Lenny's podcast

where I interview world-class product leaders

and growth experts to learn from their hard-won experiences

building and growing today's most successful products.

Today, my guest is Paige Castello.

Paige is a product lead at Asana,

overseeing teams responsible

for the core product experience of Asana.

Before Asana, she was director of product at Intercom.

And prior to that,

she was a group product manager at Intuit

where she spent five and a half years.

In our wide-ranging conversation,

we dig into strategies for building trust

with people who are more experienced than you

or older than you.

We talk about coaching product managers,

including why, leading by example,

is often the most effective strategy.

We talk about Asana's product development process

and how it's evolved over the years

as the company's scaled,

plus some of Paige's product and career missteps

and what she's learned from those moments.

To prep for this interview,

I got input from some of Paige's colleagues

and former colleagues,

and everyone I talked to loved Paige.

You'll soon see why.

Enjoy this episode with Paige Castello

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Paige, welcome to the podcast.

Thanks, Lennie, great to be here.

So you don't know this, and I didn't tell you this,

but I asked a bunch of people that you worked with

and maybe currently work with for question suggestions

of things to ask you.

So this is gonna be really fun.

Wonderful, now I wanna know who you talked to,

but we'll find out.

I'll tell you right now, a big thank you

to Jackie Bavaro, Yasmin, who's on your team,

and Montgomery, and Steve Moran, who's currently at Asana.

And so thank you to all of those folks

for giving me a bunch of great question suggestions.

Looking forward to it.

Maybe just to settle a context.

Can you just talk about, at Asana,

what do you work with, what does your team,

what do you work on, and what is your team

responsible for broadly?

Yeah, absolutely.

So I lead the product organization that's responsible

for our desktop web and mobile apps at Asana.

And the teams are composed of all the people

in San Francisco and New York,

who are focused on creating clarity for individuals,

teams, and organizations.

And effectively, our goal is to help teams

work together more efficiently

and drive the outcomes they're going for.

So you can think about the feature sets

if you're an Asana user, like goals, portfolios,

projects, tasks, reporting, all of that.

But really, we wanna help people answer the question at work,

who's doing what by when and why.

So that notion of clarity of purpose,

clarity of plan, progress, and responsibility

are often so painful in people's work lives.

And when there's certainty there and clarity there,

people can be much more efficient in getting the work done.

So that's where my focus is.

Every day, I'm a product leader for that group.

Cool, so basically like the core,

like when people think of Asana,

it's all of that stuff is what it sounds like.

Yeah, there's another group that's focused on

our process management,

that a lot of the core work and project management core

is in my group.

And then we have a growth and enterprise scale team.

And you've been at Asana for about four years now.

Yes, four years this summer.

Cool, so something I'm always curious about,

about companies that are at this scale is just,

they have evolution they've gone through

in terms of how they develop product.

And so I'm curious, just in the time you've been there,

how has the product development process at Asana changed?

And maybe even simpler, like what are the bigger,

some of the bigger changes that have been made

to the way product is built at Asana over the years?

I would talk a little bit about how we set strategy

and our planning process and how that's changed in this time,

as well as how we actually ship product

has changed in this time.

On the planning front,

we have really changed what altitudes we're planning at,

the time horizon we're planning at.

Some of the inputs have gotten a lot more precise

and opinionated.

So for example, we have always had pillar plans

and team plans, but maybe we didn't have

an intermediary layer of like an area perspective.

Well, what's an area perspective?

Well, as your organization grows,

we've had to reorganize to create more agency

and accountability close to teams

that are focused on specific target customers and problems.

So if you think about the way Asana's organized,

we've got our R&D, the pillar structure,

the areas within them, and then the working teams.

It might actually help if you even describe

like what is a pillar or what is an area?

Yeah, absolutely.

So when I said I'm responsible for that

like core product pillar, that's one pillar,

but then there's also the adoption

and enterprise scale pillar.

And the workflow pillar.

And then within each of those, there are subgroups.

And we call those areas.

And each of those areas has a very specific target customer

and problem space they're solving for.

We've often also dialed up the clarity

of the metric that level.

So while we have an R&D set of metrics,

we have pillar metrics, we have area metrics,

and then at the team level, there's often like one or two

that they're really driving forward.

And so you can think of it as a nested structure

around our product strategy,

as well as how we measure success.

And when I joined, we didn't have areas.

We were organized around projects and around locations.

And then we worked to make sure

that the thinking was more durable and problem-focused

so that our roadmaps were not about features,

but were instead about what was most meaningful

to tackle for our business growth.

And so that's a big thing

that has changed the altitude of planning and how that nests.

Another thing that has changed is the time horizon.

So before we planned annually, primarily,

and now we plan every six months,

but for a rolling 12 months.

And so we have higher confidence in the immediate half,

lower confidence in the following half,

but we just plan every 12 months every six months

because it gives our business more confidence

in what's coming and a better opportunity

to align our go-to-market and product planning.

Amazing.

So I just actually was talking to one of the heads of product

at Shopify and they went through a similar transition

where they used to plan yearly

and now they plan for the next six months.

So it's interesting that I'm hearing this more and more.

And you're saying that every six months

you revisit the plan for the next year.

So it's kind of like an interesting hybrid of those two.

Yeah, absolutely.

I think the more you try to do things

in a joined up way where you have a single target customer

with sales and marketing,

and you want to make sure that the impact

of your releases hit their mark,

the more it's important to reflect on it frequently

and to be able to pivot quickly because our strategy,

even when we think we have a two year vision,

something will change.

And then we say, wow,

we made so much faster progress on this than we thought.

And we actually believe that there's a new opportunity

or new technology that we should be leveraging.

Let's go bigger on that.

And so it reduces the feeling of churn and thrash.

It makes us all more principled

and it helps us just make sure

we're making the best use of our teams.

And I like that it also admits

you're not gonna actually have a yearly plan

like everyone plans for a year and then halfway through,

they're like, no, let's start rethinking everything again.

So like that you're upfront about that.

Yeah.

Okay. And then within the plan,

do you have quarterly plans and sprints?

Is there anything more fine grained

with like a detailed roadmap, just while we're on topic?

Not really.

I mean, teams know approximately

when are they expecting to do the work,

but if you ask too much for a particular quarter,

a particular week or date,

you'll make strange choices about scope.

And so really we align on what success looks like

and the teams do their best job to ship

as quickly as possible, as iteratively as possible,

and we really encourage prototyping.

So we added into our product process a notion

that we might pivot or cut from stuff

that we put on our roadmap

because it felt like once it was on the roadmap,

it had to be done and that's just not smart.

Got it.

So essentially there's a six month roughly detailed plan

of what each team is gonna work on.

Yeah.

Got it. Interesting.

Maybe just a couple more things

just to make them super concrete for folks

that might be listening.

What's an example of an area?

Like what's an actual team that would be an area?

And then the other question I have just while

I'm saying questions is are there some metrics

you could share of just like what some of these teams

might be gold on just as examples

if I think about metrics?

The area that came to mind when you asked about

one of our areas is something called coordinate

and their job is effectively making sure

that the slice of a sauna that helps teams work together

is working effectively.

And so that's projects and tasks

and the data that you might put into tasks

and all of the back and forth that is required

when people use a sauna for their core working team.

Some of the metrics that they care about

are like org paying weekly active users

as well as really thinking about like healthy project use.

So we make sure that we understand like

what does good look like and what is a dynamic

that we want to be creating in terms of people

getting real value from using the product.

And we build that into our metrics to have as a guardrail

to ensure that we're not driving one metric

at the expense of people really getting

what they need out of a sauna.

Just a couple more questions along these lines.

I'm a nerd sniped about process.

I think you use a process called the double diamond process

at a sauna.

Okay, cool.

I've seen images of this in various places

but I don't know of any company that's actually

using it as like the process.

Can you just describe what the double diamond process is

and how you use it?

So you might be familiar with kind of lean startup concepts

and double diamond as it relates to going broad

and then going narrow.

And so you go broad when you ask like,

what customer should I solve for?

And then you pick one.

And then that's the narrowing.

And then you go broad and you say,

what are the problems this customer has?

And you narrow and you say, this is the problem they have.

And then you go broad and you say,

what solution should we do to this?

And then you go narrow and you say,

this is the solution that we should start with.

That process of going broad and going narrow

and going broad and going narrow forces people

to get out of their opinion driven lands.

Because so often we really want,

we need to be curious quantitatively

and qualitatively about what we're doing and why

and be more systematic and rigorous about getting there.

And it doesn't take long, but it just breaks the frame.

And so the double diamond process at Asana effectively,

each of our typical reviews or artifacts

sit at different inflection points on the double diamond.

So we actually ask people to do a kickoff

where they collect different information

at different scale depending on the size of the problem

and the ambiguity they're solving.

Some people have already done enough customer selection

and research that they're starting

with what are the possible solutions to this problem?

And then they're bringing the spec

and that's the narrowing alongside designs, et cetera.

But it's really mapping our artifacts against this notion

to make sure that the product thinking

has that quality of decision-making.

And the way you described it

is it was very customer target oriented.

Is that the actual framework?

Is it around who to build this for and then what to build?

Or is it more, it is, okay, you're not gonna do that?

It is, yeah.

It's really important

because then you also know what success looks like.

Because if you pick your success metrics

as using a feature, that's it.

You're teaching to the test,

it's not actually driving the outcome.

So while our planning process is around effectively

defining the category and how we win

and making sure that customers receive certain benefits

from using work management,

the through line to the individual project

that a team might be leading

is they need to know who they're solving for

and what it means to have that problem solved.

And so it always starts with enough customer insight

such that we can creatively do what they're trying to do.

Really inventing on behalf of customers.

Can you maybe repeat if there's like terms

for each of those phases?

And then- Yeah, absolutely.

And then is there like an example

of a feature or product that went through this

that you could share?

If nothing comes to mind, that's okay.

The inflection points are the kickoff,

which is that going broad.

And then customer and direction selection.

So this is both the target as well as

of the 10,000 foot views

of how you might pursue solving this problem.

Which path are you broadly gonna take?

And then going broad within that path

on different concepts.

And then there's a design concept review,

then the product spec,

then the full experience review

or design crit of the end-to-end experience and launch.

And so that launch review is often just,

hey, here's the thing,

here's what we said here at the fast follow.

Most of the time, by that time,

it's already been dog-fitting internally for some time.

It's more of a formal,

do we have the right metrics in place?

Are we ready to shift?

Awesome.

Did these reviews happen in person on Zoom or asynchronous?

It depends.

So it depends on the complexity of the work.

And it depends how much we wanna talk about it.

A lot of our crits happen in person on the design side.

A lot of spec reviews are more asynchronous.

And then we'll say,

depending on the number of questions people have,

we call a meeting.

Otherwise, we do mostly async,

but it's a mix.

It really depends on the complexity

and ambiguity of the solution

and how much people have questions

about asynchronously beforehand.

I'm gonna take a tangent with my questions here

and talk about work from home policy at Asana.

This is something that I've been wondering more and more

about how it's changing

because it feels like there's been a shift back

to the office.

So what is the current policy at Asana

and what's changed maybe over the past couple of years?

Well, we were fully remote during the pandemic

and then we came back to the office

in an office-centric hybrid format.

So we're in the office Monday, Tuesday, Thursday,

and then work from home mostly on Wednesdays and Fridays.

And that dynamic has been designed from the start.

We wanted to make sure that we took advantage

of what's great about working together as teams.

And so it's been the standard.

So I would say what's unique about maybe Asana

is we knew we would do that from the very beginning

instead of hemming and hawing

about would we be a remote workplace or not

and what would that mean

and how would we come together

and how would we budget for it?

We're like, nope, this is gonna be an office-centric hybrid

because we wanted to create spaces for people

to work together and move quickly.

It's been interesting watching people get back

into the swing of things.

It was not, even though we knew,

it didn't mean that on day one,

people were great at being in the office.

People were taking stand-ups, sitting down,

whereas before you would walk through our office

and you could hear people at stand-up

because there were stand-up chants

and people would be out on the floor.

Now people are more likely to do their stand-up in a room

and we're trying to, you know,

the next level of standing up during stand-up.

But it's kind of,

I'm sure it's a shared experience for other people

who are working in offices

to get used to using the whiteboards again,

to get used to like standing up during your meetings.

It's bizarre that we could lose a muscle that we had

that was so innate so quickly.

And I think even in the last month, I would say,

and it's in June of 2023,

there's more vibrancy in the office,

more conversation, more casual.

Someone eating alone at the cafeteria

and someone sitting down next to them.

So it didn't happen overnight.

I've been seeing a lot of tweets of founders

just being like, work from home has failed.

It's time to go back at the office.

And I'm curious if that ends up rolling

into more and more companies

or if it's just like, you know, a few founders here and there.

I think it's a real thing for mental health.

I do think that having social casual relationships

as well as more opportunities to talk strategy

with people you're not forced into a meeting room with

has been super beneficial.

I can say that just today I was having lunch

and sat down with my head of data science

and we had an impromptu chat

about how we review our experiments

and how to evaluate whether we had ROI on learning,

not just the metrics.

And it was one of those things

where if we had to schedule it, it might not have happened.

And if it did happen,

it would have been a couple of weeks from now.

It feels like just coming into the office once or twice

or sorry, being at home once or twice a week

is not that different from how things used to be

where there was a day of no meetings

and a lot of people stayed from home.

So it feels like it's almost reverting back to that.

And people are better at it than they used to be.

So I would say our remote days are more impactful

and then the days we're together

where we're getting into the swing of things.

Yeah, I feel like as a PM,

the only day I was productive

and like getting real deep work done was the no meeting

Wednesday, it was at Airbnb.

I would encourage you to know your chronotype

and to lock that time

where you have the most headspace to do that work.

For me, it's warnings.

Say morning chronotype, what is that?

I'm a morning person and so I try to make sure

that I don't have any meetings before 10,

sometimes before 11,

and that's when I do my hardest task for the day.

I also just thought about stand-ups while I was at Airbnb

and not only how much energy they brought,

but almost too much energy sometimes

where there's like another team doing a stand-up

and they're just like laughing and clapping

and we're just like, trying to work over here.

I feel like we need more of that again.

Totally, yeah, yeah.

Okay, so moving in a slightly different direction,

something I heard about you

is that you're often the youngest person in the room

and you often lead people

with decades more experience than you.

And I wanna ask, what have you learned

about how to garner trust and win over skeptics,

especially when they're maybe more experienced or older

and especially in other functions,

I don't know, execs or designers, engineers,

what have you figured out there?

The thing I would say is bring the insight.

Know thy customer, know thy market,

know thy competitors, know thy numbers, know thy product.

If you can be the person in the room

who has watched customers use the product

and has a point of view about why one tool

is significantly better or worse in a given dimension

and you can do that with confidence and clarity

and you don't need to know

the other person's functional domain

and you don't need the expertise

and what their expert's at,

you can bring insight that makes people curious

and trust you and just immediately believe

that there's an opportunity

that you're not advocating for that just is true.

But I think that's a really tricky and unique thing

is not to pretend like you have more experience than you do

but to be willing to ask great questions

and then be curious enough

that you're bringing insight to every meeting

that people may or may not have

but you're always willing to share.

That's such a good answer

because there's not a trick to it,

it's just do the work, spend the time

to become the person that has answers that people value

and obviously they will respect you,

value your opinion, wanna hear from you.

Yeah, yeah, our former board member Ann Raimondi

and now our head of business

wrote an article on first round

that was really great about kind of the trust equation

and it really resonated with me

and I don't know if you've heard about it

but she said that trust is equal to credibility

plus reliability plus authenticity

divided by or over perception of self-interest.

And I think when you're met by someone

who doesn't know you, doesn't know your work,

your job is to create credibility

and that's where I said like bringing the insight

is where you can really tip the scales here.

Reliability, this is all about your say-do ratio,

authenticity and just, you know,

being vulnerable, being yourself

and then making sure that people know

that you're not in it for some other outcome or cause,

that perception of self-interest really can change

whether people, like how much they trust you.

In terms of knowing the insight and knowing that customer,

putting in the time, I imagine is a big element of that.

Is there anything, is that how you do that?

Or is there anything else along those lines

that just like here's how I get really good at this?

When you take a new role,

become best friends with a researcher

and spend time with watching customers

use the product firsthand

because what they may be report on

or are trying to do a study about

might be very different from what you observe

but you really just need that front row seat with customers.

And so asking for how do I actually set up time

with customers, how do I compensate them?

How do I like read the tickets, whatever.

It's amazing how little you have to do

to quickly catch up to understanding

who the organization is solving for well and poorly

and like how people really use your product

versus how your teams use your product,

especially in organizations

where there are heavy dog-fitting cultures.

It's really risky to become less sensitive to the needs

and behaviors of customers

because people think they are their customer

and it also becomes very navel-gazy.

So I think the more you get out and break up

how people are having conversations

about what we should do and why

and what we shouldn't do and why

and it's not about your opinion,

it's about asking questions and then bringing insight

that can really change the nature of the conversation

and build trust.

I love that.

In terms of confidence,

you talked about the importance of communicating

these things confidently.

Is there anything you've learned about

how to be more confident?

A manager, part of it is like having the answer

but is there anything there

that you maybe coach your PMs around

or other folks have just like,

here's how you communicate confidence?

It's a great question.

I think being brave and courageous in little moments

just kind of what you have to do.

You have to show up and say it

before you're ready to say it

and ask for forgiveness and be vulnerable.

And I think when you're vulnerable,

people actually trust you more

than if you come with all of this armor

and say, I know this

and this is how we're gonna do it.

And so real confidence is often conveyed

by being willing to ask the question

or to say, I don't know what you mean by that.

Can you say that again?

It's also just how you communicate,

looking people in the eye,

your body position, your body language,

so much of this I think people forget about

because it's really easy to be in a meeting

and looking at your computer

and going through Slack messages.

And so one of the best things you can do

is if you're in a meeting, be in that meeting.

Continually scan the faces of everyone in the room,

see if someone has a question,

pause at the beginning and welcome people

and chit chat while people land

and then close asking questions.

Like, did I get all of that?

Is there anything you would have expected to cover

that we missed?

It's really about being open

and that conveys confidence more than being assertive

and advocating 100% of the time.

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From my chats with folks that you work with,

it's really clear that you put a lot of time

and energy into mentoring and coaching PMs on your team

and I think probably broadly at Asana.

And one thing specifically that came up

is that you're very big on leading and teaching by example,

not just here's how you do this thing.

And so if that's true, I'm curious where that came from

for you and why you think that ends up being

a lot more successful than like in a meeting

you should do XYZ versus like doing it

and then letting them see.

I think the main thing is repetition.

We're all students of repetition.

If you see something done a few times,

you're more likely to remember it and internalize it.

And so it's also something that, a way that I learn

and so I think that's probably part of it.

But I remember hearing about a framework called

the three E's, experience, exposure and education.

And I think it was helpful for me to hear that

as like a way of growing your career

or being more purposeful about your growth

because I think when people are earlier in their careers,

they tend to think education, education, education.

And then they started to think experience, experience,

like how do I get the experience of being a manager?

I need to like read about it and be a manager.

It's very linear.

And exposure was such an important one where I thought

like, okay, so you're not in the driver's seat,

but you're in the car and you hear what's happening

and you're evaluating how this is like what the impact is.

And this goes back to being really present

and analytical and being a learner

because if you can be a learner,

not just in an educational experience context,

but in an exposure context,

you can really grow so much more quickly

and in so many more directions

and you will get from just what does your day entail

from what work is directly required of you.

Is there an example of that happening either to you

or you saw a manager leader do this

and you're like, oh, I get it now

or you doing that and it helped?

So I'll give two examples.

One is like the way I run my meetings

are the kind of meetings I want to be a part of.

So I try to make sure that I start with a clear agenda

and I move quickly, but give time for conversation

and it's not fully just sharing information,

but debating where appropriate.

I think knowing how to like manage the conversation

and courteously pausing people who are going on too long

or like taking the group in a different direction

than was intended.

And just think about the experience of everyone there

and create the experience that you hope

that they're creating in the rooms

that you're not a part of.

An example that I have in terms of experience

is like sometimes the experience is you doing the thing

and getting that experience firsthand.

Other times you need an education,

you need a mentor, you need a coach

who will tell you what they're saying or give you advice.

I was in a really high stakes product review it into it

and at the end of it, everyone else had left

and like the leader of the business unit

as she was leaving the room said always ask

or always answer the question that they should have asked.

And always answer the question they should have asked.

And I was pretty surprised by that advice

because it was very profound in the moment

because I think when you're a student

and you are accustomed, if you're an achiever,

you like to get A's,

you're probably going to hear a question and answer it.

You're like one to one, one to one, one to one.

But what I learned from that was that there's actually

another altitude, another point of strategy

when you're in a meeting or in a conversation

to make sure that you're covering

the more important point, the bigger picture,

the alternative that the person asking the question

maybe didn't see or consider.

And so I think the mix of experience, exposure

and education really helps you make sure

that you're consciously moving forward

on each of those fronts or finding people

who can help you there.

I love that piece of advice and it makes me want to ask,

are there other pieces of advice

that have been really impactful to you

or are there common pieces of advice you give to your team

that just like as a recurring theme of advice

that maybe people even make fun of?

Like, oh, Paige is always saying this.

There are a few ways to think about advice

and my advice often like meets a mark

when it's for a particular person

at a particular time in their career.

And so I would say advice I love giving to people

who are early in their career is don't self-select

because I think it's really easy to say,

I don't have the experience or I'm not XYZ enough

and not apply.

And so I really push people not to self-select

and I try to remind myself where that's appropriate

to do the same thing.

Other advice I often give is just think big, ship small.

Think big, ship small, like what's the smallest thing

you can do to do that thing?

But that's not because we're trying to ship all the time

and in small chunks, start thinking in small ways

because it's really easy to get a little too incremental,

a little too wrapped around the axle

around optimizing a metric and miss the bigger picture.

And so think big, ship small is another piece

of product advice I give.

And the last piece of advice that I would say

that I like is more of a way of thinking.

So this is a little abstract,

but when employees join us on it,

they get a book called The 15 Commitments

of a Conscious Leader.

It's led by the Conscious Leadership Group.

They also get two-day training on some like language

and tools for how to effectively work with other people.

And it's a really, like for me at least,

it was transformational because I learned

some vocabulary and methods that I could share

with my peers.

And one of the things that you learn

is to be above or below the line

and something that is this concept of where are you?

Are you above the line?

Are you below the line?

If you're above the line, you're committed to learning.

You're open and curious.

Things are funny here, more playful.

If you're below the line, you're committed to winning.

You're committed to being right.

Things are more black and white.

And all of us have days where we're having a conversation

and we're really like in that below the line space

where it's like, no, it just is this way.

There's no two ways around it.

And that concept of understanding your personal headspace

and then being mindful of how you're operating

when you're in that place really was great advice for me.

And also recognizing where other people were

when it related to decisions we were making or context.

It also helped me think about rejecting false trade-offs

and challenging like effectively there's this notion

of how might the opposite be true.

And that's a piece of advice that I give myself

like this morning.

I think it was yesterday actually.

I was like, how am I going to do tomorrow?

Like tomorrow I have to deliver the clarity pillar brief

to the area leads and make sure they understand

our stack ranked metrics and they need to know exactly

what our strategic priorities are and why

and they need nudges and they need to be able to translate

our voice of business and usability lists into those plans.

And I need to establish a perspective

and make sure this is all written down

and they really understand it.

And I have a great conversation with them

where I get open questions

and they feel like they can really challenge my thinking.

I also am having a podcast with Lenny in the afternoon.

Ah, right?

And at first it was like, I can't, this is just too much.

Like I should like try to move or cancel one of these.

And then I asked myself, how might the opposite be true?

And I was like, I can do both.

Like it was just enough to pop the balloon

because sometimes your brain is so accustomed

to having a scarcity mindset as opposed to

like creating alternative options

or seeing a different path.

And the moment I challenged myself

and said, how might the opposite be true?

My shoulders dropped, I felt more relaxed.

I was like, oh yeah, I can do both.

It'll be fine.

Well, I have a great conversation.

I'm ready to show up and be curious

and like really engage with you on the topics

that you've found interesting and we'll just do that.

And so how might the opposite be true

has been a really helpful piece of advice

or line of questioning that I use with myself

to make sure that I'm not taking myself away?

Wow, what a fruitful question that ended up being.

That was amazing.

How does clarity pillars strategy go?

Are people into it?

Is it working?

Yeah, I'm pumped.

It's a really interesting time to be a product leader.

Especially with all of the tech transform,

like truly the technological transformation on LLMs

is astonishing, the pace of development,

the ability of our teams to just ship quickly

and ship really intelligent things.

Like we're not in an operational figure at Outland.

We're not in a place where we're trying to decide

how to do a better job and get it out to customers.

We really have lots of interesting paths forward

and are trying to make sure that we're on the cutting edge

while really looking at like what does it mean

to serve the companies and organizations

that we want to serve with new ways of serving them.

And so it was a really fun conversation

and I also had to be honest with people and say,

this is a 70% cut, 30% of this is missing or incorrect.

And that's why I'm coming to you early.

And so I think it went really well

and it's the start of our 12 month

rolling planning conversation.

Let me pull on this AI thread

because it's clearly top of mind for a lot of people.

How do you think about splitting up investment

in AI exploration within the product team?

Are you like, hey team,

everyone should be thinking about AI as part of their product

or is it, here's a team or they're gonna think about AI

and LLM integrations and everyone else,

keep doing what you're doing.

We've had an ML team for quite some time

making sure that we have like test prioritization models

and like notification prioritization models

and are making our product less work for people to use.

But when it came to the massive leap forward

in LLMs recently, we staffed a team

to really prototype quickly and discover what was possible

and just apply hypotheses outside of the typical norms

of how we work.

So they kind of went straight to prototyping

instead of going through that double diamond

I was explaining earlier.

What that meant was that we were really quickly able to say,

wow, there's just so much better than we imagined

and would never have prioritized it

because we thought it would take so much longer.

And then in other cases, that sounded good in theory.

And so skipping a lot of that

to just really try it on for a size has been key.

And then what we're doing is giving the teams

with the most expertise in the customer problems.

For example, status and progress reporting,

the keys to that car and saying like,

here's the starter, here's the hypothesis,

here's how far we got with it.

It's dogfooding, what do you want to do?

And so we're able to like nudge people

without wasting time and build the skills locally

within the teams that then move those experiences forward.

I want to come back to the coaching topic

at a few questions there that I moved off of,

but I feel like that's a rich, rich area of exploration.

You mentioned Intuit, you worked at Intuit.

Intuit is kind of famous

for having a really good APM program

and really good training for product managers.

What did you take away from that experience

that you bring with you to coaching

or even I think there's an APM program at Asana too?

Intuit had excellent training programs,

the APM program and their manager training.

So on the PM front,

the biggest thing that they taught

was around customer centricity.

And it really started with the founding of the company,

like if for anyone who works at Intuit

or has worked at Intuit,

they know that there's the story about Scott Cook

watching his wife balancing her checkbook

at the kitchen table and staring at it

saying, he's got to be a better way, a software.

So it's very typical for the product training at Intuit

to be all about like,

how do you spend and like,

how do you actually watch customers using your product

or just doing the things they do,

collecting the artifacts, knowing the workarounds

and using that experience to build opportunities

for surprise and insight

that then you can capitalize and create products around.

They also are very specific

about how they define a durable advantage

and think about overall like the product process

from a place of customer insight

through to like the market landscape.

So the PM program there was absolutely super thoughtful,

especially for taking someone who has never PMed

into being a super skilled PM.

They also have a wonderful manager training program.

And I think the biggest thing that I took away

from their manager training

was really on the feedback side.

So delivering feedback is something

that I think everyone benefits from,

but for managers, it's so much more critical

because if you don't do it and you don't say what you mean

and you don't do it in a way that it can be internalized

and acted upon, you really don't set up your teammates,

your teams for growth or success in their careers.

And so their program for helping you think about like,

okay, I'm gonna convey this feedback

as situation behavior impact.

Like the situation is like on Tuesday

in that meeting at three o'clock behavior,

you interrupted me while I was saying this thing.

Impact made me feel like you weren't listening to me

or made me feel like your voice was more important than mine

or impact, blah, blah, blah.

It doesn't matter what the impact is

because the way you've set it up

is it's a subjective observation.

It's not what the camera recorded.

It's what you experienced

and therefore it is true and valuable feedback.

And it gets the conversation started

such that you can then talk about next steps.

And that format and framing really helped me understand

that delivering feedback isn't about being right

or about getting the right information to the other person.

It's about sharing the impact

of different decisions that they're making.

So especially if you have to give feedback

about God forbid what someone wears to the office

or how do you tell their work is

or how they're communicating or their body language,

having enough support where you can be really clear

about what you're intending in the spirit behind that,

but that it's formalized enough

that people can really engage with it

has been enormously helpful and I still use it today.

It's interesting how some of the most impactful training

is like such soft skills.

So basic.

And basic, yeah, just like how to give someone some feedback

but it's like not like how to prioritize,

how to do a meeting or give a presentation.

It's like, here's how you get feedback to someone.

Yep.

So you've worked with a lot of early product managers.

I'm curious what you find most holds back new PMs

in being successful in their career.

And even on the flip side, what most helps new PMs

be successful in terms of skills or behaviors, habits,

things like that.

I would say this illusion that you have to be all knowing

and super confident sets you up to be in a place of advocacy

instead of inquiry.

And so PMs who are newer in their careers

or who are like in a different space

than they're accustomed to working

really wanna be pro really fast.

And what pro means is trying to cut that straight path

and that can reduce information and conversation

that makes you smarter.

And so some of the challenges that some PMs face

are feeling like they need to be the expert,

they need to be the smartest person in the room

or God forbid they think they're the smartest person

in the room.

And then what happens is they're really doing that customer

or product discovery or a spec in a little dark room.

And then they show up and they say, this is it,

this is right and I know it's right

and let's do this as quickly as possible.

And everyone else says, wait, what?

Like, I don't know, I have a question or they don't

and they still have a question, which is even worse.

So I would say something that really holds PMs back

is not being collaborative from a place

of like true curiosity, like performative collaboration

where they like nod in a room or wanna do a review

but ultimately they don't really want

the questions or the feedback.

And I think trying to make sure that you can be

in a place of curiosity and openness

because that will make your experience more successful

is really important.

Other people aren't always gonna be right

but if you're present for it,

you can ask clarifying questions,

you can ask the question behind the question,

you can hear the feedback and then say,

was that something that I must do, that I should do

or that I should consider?

You can actually develop a conversation

that will move your relationship forward.

And so I would say that's something

that I think holds PMs back.

PMs tend to be so ambitious and career-centric.

And there are so many good things about that.

But I would say like, don't let the sound

of your wheels drive you crazy.

If you're present in your job

and you actually have fun with it and solve the problems,

people will come out of the woodwork,

say you're great and tell your boss you should be promoted.

You don't need to ask for a promotion.

Your outcomes should speak for themselves.

And yes, you should have sponsors

and people who advocate for you.

But a lot of that just comes from that like raw connection

to the work and to your team.

Everyone I talked to about you was like, oh my God,

I love Paige and I could see why.

But I wanna ask you a question.

I imagine you've made some mistakes

either with a product or your career.

I'd love to hear a story of something that went wrong

and what you learned from that experience.

And this might be the last question

depending on where you take it.

I would say that all of the advice I've given so far

is directly related to things I've learned the hard way.

So like, especially as an IC moving into a management role,

you aren't supposed to have all the answers.

You need to ask better questions.

You need to be thoughtful about like direction and agency.

And so I would say one of the missteps here

is like knowing how to give guidance or direction

in a way that doesn't feel like micro management

because what you're trying to do is to teach

a repeatable pattern instead of giving a precise instruction

that can be used once and then disposed of.

So I think that's a pretty common manager pass issue

but I think the faster you learn it and observe it

and use techniques to manage it, the better.

So for example, I would go to my meetings

with a stack of post-its and I would write

what I wish I was saying on post-its

and see if someone else would say it first.

And then if by the end of the meeting,

I had decided that I still had a post-it or two

that was worthwhile, I would say them.

But you've got to police yourself

because no one else will do it

because no matter how accessible you think you are,

other people know that you're the boss.

They're not gonna necessarily speak over you

or challenge you directly.

Another challenge I had is I'm a very optimistic person

and I like to look on the bright side, I'm very positive.

And I think depending on the culture you're working with

or depending on your team,

sometimes they need to hear what's really bad

and they need you to be really real

and they need you to tell them like it is.

And something I realized was that I had an experience

where I didn't realize that people didn't think

I was being authentic because they thought something was bad

and I wasn't talking about it,

but it wasn't because I didn't think it was bad

or didn't see it, it was just because my nature was to say,

well, I'm not gonna talk about bad things

because we're doing the things we need to do.

Like as long as the plan is good,

I wasn't really highlighting all the problems I saw

or really pushing on those head on with my team.

And so they felt like they didn't know what I was saying

or if we were saying the same things.

That was really an interesting experience.

Yeah, there are just so many.

Yeah.

With that second lesson,

is there something you've changed

in the way you lead and operate

where you now found a way to communicate

here's what's wrong in a way

that's still maybe optimistic and productive?

I try to be more real with myself and others.

I try to show up and say, hey, this is incomplete.

Like for example, even the thing I did this morning,

the clarity brief, I said, this is 70% finish.

The 30% that I don't believe is there yet

are these three things.

I don't feel confident in this piece of it.

And hopefully we'll have more clarity by next week.

So that's an example of just being as real

with the small things as with the big things

so that people can balance their perspective

of you and your work and the organization,

the environment you're creating.

I'm curious how you think about your career going forward.

How far out do you think where you wanna be

and how do you kind of plan out the future of Paige's career?

I try to be really intentional

about staying as much as leaving a role.

And when I think about my career as a whole,

I try to think about like skills or experiences I wanna have

as opposed to roles or companies or specific problems.

So something that I think about is like effectively,

I evaluate whether I'm in a healthy role

and then a good setup by asking myself about my learning curve.

Like is the steepness of my learning curve

doing me a favor here?

Because sometimes you might love the organization,

love the problem and feel like you're just not learning

or learning fast enough or being challenged.

And that's something that I think is really important.

So like thinking about the learning curve,

thinking about whether the environment

is positively impacting your ability

to grow your career and make an impact.

And so environmentally, you might have like not enough staffing

or tooling or have someone in the management team

who is toxic or have a peer who is blah, blah, blah, blah.

That stuff matters.

And I think people don't talk about it

or take it seriously enough

that your environment should include people

who are advocating for you

and it should just be a place where you feel

you've got the right ingredients

to set you up to do the good work.

And then the third piece is really around just the problem.

The problem your product is solving.

Is it fun? Is it interesting?

I often like to think about like passions are made not found

because I think people kind of,

we do this with nine-year-olds who say,

what do you want to be when you grow up?

They look cross-eyed and they say,

an astronaut, just getting a vet.

I don't know.

And there's this moment of like panic.

And I would say that being comfortable,

saying like, go try different things

and see if the problem is interesting to you.

And if the problem is fun or interesting to you,

it doesn't mean it has to be sexy.

It doesn't mean the company needs to have a brand name.

It just has to be something that you're curious about

so that you do a better job at your job.

So I would say learning curve environment and problem

are things that I use to assess like,

am I still on the right path

or should I consider an alternative?

But when I think about my own career,

I really think about skills and experiences

as opposed to roles.

So I would say that that's more my frame of reference

because otherwise I think I'm living in the future

and not enough trying to make the most of out

out of the career I'm living right now.

Well, with that, we've reached our very exciting

lightning round.

I've got six questions for you.

Are you ready?

Yeah, let's do it.

What are two or three books

they've recommended most to other people?

My go-to book recommendation for other PMs

is inspired by Marty Kagan.

I think it's classic.

The other books that I have enjoyed and recommended

are The Blind Assassin by Margaret Atwood

and The Alchemist by Paula Quello.

What is a favorite recent movie or TV show?

Ooh, I'm very much enjoying the diplomat right now.

And then TV show or movie, let's see.

I just watched the Fire of Love documentary

which is about a couple who study volcanoes

and that was a great change of pace.

I saw the trailer for that.

I think I got to watch that.

And I finished the diplomat.

It's awesome.

It ends really well.

I'm not, don't, don't spoil it.

But it's just good.

I'm just saying it's good.

That's not gonna spoil it.

Okay.

Okay, next question.

What's a favorite interview question

that you like to ask candidates?

The good news is I can tell you this

and still keep asking it.

Because the answer has always come up differently.

So I like to ask, tell me about a time something went wrong.

What was it?

What did you do about it?

Yeah, yeah.

And effectively the question gets that

when the product failed,

when something about the team didn't work,

just things that go wrong

because that's what happens when you're doing this work

and evaluating people's mindset

and the way they talk about it

and the way they relate to evaluating the situation.

I think it's a great question.

Really tells you a lot about how people think

and how they perceive themselves

when things are not working well.

What is a favorite product

that you've recently discovered that you love?

I've been playing a lot with Po.com lately.

Yeah, just an opportunity to learn more

about capabilities in a firsthand way.

It's been fun to create little bots.

I'm playing with making a page bot.

I can't say that the page bot could have had

this conversation yet,

but maybe next year at this time

you can have a conversation with the other me.

That's what the page bot would say

if this was the page bot talking right now.

I would say though,

but the advice bits and bobs I gave you earlier

are absolutely things that I've been thinking about feeding.

But I think the page bot would probably say ship it.

Po, it's the Quora Founders LLM chat bot.

Yeah, and so you can try the different models.

So you can do four and you play five

and Claude and a few others.

Yeah.

There's also a Lennybot.com for folks

that haven't seen this.

Somebody built, actually there's a whole post

on my newsletter of how it was built.

And you get a Lennybot.com

and it is trained on all of my newsletter posts.

And I think not yet podcasts,

but someday it'll have podcasts.

By the way, if someone's listening to this,

we're looking for someone to maintain this bot

and evolve it.

So if you're really into the stuff

and have done this sort of thing,

please DM me on Twitter.

And I'm looking for someone to take over

Lennybot.com, make it more awesome.

Moving on, enough about me.

Next question.

What is something relatively minor

that you've changed in your product development process

that has had a big impact

on your team's ability to execute?

One of the biggest ones is just being,

once again, being real about how many reviews

and approvals it takes for something to get done

and who's actually responsible

for reviewing and approving work.

So we got really aggressive about functionally

who is in charge and at what level

before a given review and pushed to say,

like to actually have limits

on the number of people per meeting

on the number of subtask reviews

for a given body of work.

And what this did is it created a lot more agency

and pace within given working teams.

And so what we did was we said,

we actually don't care.

We don't want a daisy chain of approvals.

We just want one person with whom the buck can stop with them

and they can be responsible for how the work moves forward

such that like the knowledge is known

and we could have connected dots more effectively

than we do or did.

So that's kind of the logic there

and it's really changed the pace and quality of our work.

I love that.

Is there any more you could share on the number?

Like what is the maximum?

Is there anything that other people maybe can take back?

Yeah, so no more than three reviews

on a given piece of work

where people are blocking one approver.

And if a meeting has more than 10 people on it,

we ask the person hosting the meeting

to kick out the other people and write better decision notes.

And the three reviews is three meetings

looking at the product as it's coming together basically.

The three reviews are three people

who are assigned a task to look at something,

but only one person is blocking

whether it moves to the next stage.

Got it, informed people, stakeholders, decision makers.

Okay, great.

Final question, you were going to Asana.

What is your favorite Asana pro tip?

I use Asana to run all my meetings and assign pre-reads.

So I use the multi-assign feature in sub-task all the time

where I make a task with a due date

that says read the sing by this date.

And then I assign it to a team

or a set of individuals like that really quickly.

And then when I'm in the meeting,

I take notes live in a task

and then highlight parts of those notes

and convert them into sub-task

so that none of the action items get lost.

Wow, you need to make a video or a blog post about this.

Not only is it using Asana to build Asana,

it's using Asana to run teams within Asana.

Yeah, it definitely does that.

But it's not all the way down.

People know who's responsible for what by when.

Amazing, Paige, you are awesome.

Thank you so much for doing this.

Two final questions, working folks find you online

if they want to reach out and learn more.

And how can listeners be useful to you?

You can find me on LinkedIn and Twitter,

Paige Costello, and on Twitter at page now.

Listeners, well, I'd love to hear how you think

AI is gonna shape the future of software

for knowledge workers.

But in particular, if you and your team use Asana,

I'd love to know where you'd like to see AI

playing a bigger role to drive efficiency

and alignment for your team.

So as you know, we offer a ton of goal management,

work management pieces that help teams and orgs

do their work together.

And I'd love to hear from you

about where you see the opportunity.

Awesome, Paige, again, thank you so much for being here.

My pleasure.

Thanks for having me.

Bye, everyone.

Thank you so much for listening.

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Machine-generated transcript that may contain inaccuracies.