Lenny's Podcast: Product | Growth | Career: Building a long and meaningful career | Nikhyl Singhal (Meta, Google)

When I was a kid and I was growing up in the Midwest, entertainment was like going to the

dog tracks. The way that they motivated the dogs was they had these like fake rabbits.

These tails would go around faster than the dogs, which would then motivate the dogs to go

around in circles. And what was interesting is the moment that the dogs, if they accidentally

touched the rabbit, they would never run again. Because there was like, well, what's next?

I've achieved what I was looking for. And so I think this happens a ton is like your listeners

are spending time focused on like, well, one day I will be X. I will be that vice president. I will

have more money. I will have built something. I will have started a company. But they don't think

about what happens next. What's the second thing? What's your career next look like? How do you

ensure that you are always going to have something important and motivating to do with your career?

Otherwise, you'll keep working because you don't know anything else to do, but you'll be

sadder, or you'll find ways to create war when peace is needed.

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 Nikel Singhal. Nikel has worked on and led large teams on

four different influential consumer products, including Facebook, credit karma,

Google Hangouts, and Google Photos. Currently, he leads product teams for the Facebook app at Meta,

overseeing groups, stories, messaging, and the feed. Before that, he served as Chief Product

Officer at Credit Karma and held various leadership roles at Google. Nikel has also

co-founded three different startups, and as you'll hear in this episode, is extremely passionate

about coaching and mentoring, sharing his knowledge through his newsletter and podcast called the

Skip. In our conversation, we cover all aspects of the PM career and what it takes to be successful

at every stage of the journey, including the dangers of thinking too short-term, the importance of

avoiding what he calls ex-growth companies, why you're probably not getting promoted, what to

focus on if you're a new manager, the rise of the senior IC path, also why top leaders often have

huge development areas they don't know about and how to catch them, and also why people who make it

to the top often run into serious mental health challenges. As I say at the end of this episode,

this might be my new favorite episode, and I'm really excited to bring it to you.

With that, I bring you Nikel Singhal after a short word from our sponsors.

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Nicole, welcome to the podcast. Thank you, Lenny. I appreciate it. I'm happy to be here.

So I have a very simple question to start. How many product managers have you been

a mentor to if you had to put a number on it? Good question. I just haven't thought about it

from that perspective. I would say hundreds is probably the way to sort of answer the question.

And a little bit has to do with whether or how we define being a mentor. I know that was supposed

to be a simple question and I'm going to give you a complicated answer. But I think that I started

out just helping people, you know, 10, 15 years ago trying to help them through their careers. I

find the whole area really interesting. And then what happened? It was just hard to scale because

people were always like, hey, can you find time? So now what I do is I tend to help and coach

hundreds of folks through transitions. So if they're in a moment where they're trying to decide

between another job, if they're trying to decide to leave, if they're having a sort of an alert

at work, I call them 911 calls. I take a few 911 calls every week and from a relatively large

group of people. And so I find those are the most substantive times to help people as when

they're in moments of dilemma or forks in the road. And that's why the number is more closer to

hundreds. Okay, follow up question. How many of those people you've mentored have been on this

podcast? Probably half dozen to kind of close to a dozen at this point. Yeah, easily half dozen.

Amazing. Okay. Is there any names you want to name or should we keep it anonymous?

Yeah, we'll keep it anonymous because I want people to feel like and always call me and not

feel like that. I don't tend to share the names of the most people. Okay. I know the one person

that's self identified was Annie Pearl from Calendly who is a big advocate of the stuff that

you do. So Annie is someone I learned from and help talk with. And she's also part of a community

that I also built on the side where we pulled a bunch of CPOs together and they've been building

community. I'm a big fan of community and learning and that's she's part of that as well.

Awesome. I definitely want to talk about that, but maybe just set a little context for our

conversation. I feel like you're in the very high percentiles of people that have seen a variety

of careers in product management, both good careers, bad careers, junior people, senior people.

And so I want to focus most of our time on talking about just the PM career path and what

you've learned about what is important to have a successful thriving, happy PM career. Does that

sound good? Perfect. Okay. So I'm thinking we break up the chat into like early career,

mid-career and late career. And so within the early career section, you've talked about how

people often make a mistake in their early career, specifically being very short-term focused in

deciding where they're going to go. And that's a very dangerous way of thinking about it. So I'd

love to hear just your take on exactly what does that mean and then why is that actually a bad idea?

Yeah, I tend to be long-term focused in most of my counsel. And maybe

to give you an example, what a short-term focused career kind of framework looks like is,

I really dislike my boss. I feel like this company doesn't have it anymore. There's just too hard to

ship things. Those are all maybe true statements, but they probably exist in many of the jobs that

one would consider if they were to move from one to another. Lateral moves are, by definition,

not forward moves. So what I try to tell people to think about is work backwards from your end

state. Almost think of career as a product. So if you're building a good product, you think about,

well, here's what a great product would look like, and then you break it into version one,

version two, version three. Well, in some ways, the reason I called my newsletter, my podcast, The

Skip, is because I always think about what's not the next job, but the one after it. Maybe think

about not your boss's job, but your boss's boss's job, and what do I need to think about to get

there. And in many ways, you may think, well, okay, if I need to found a company one day,

and that's my job after next, then you want to look at maybe your current job and then maybe the

next job in service of that. And that may lead you to saying, hey, maybe I need to grid it out,

and maybe I should stay, and maybe I should learn how to deal with some of this ambiguity.

That's why I want people to be a bit more longer-term and not so short-term focused.

What are some other examples of that short-term thinking you talked about? My manager sucks,

things are moving really slowly. What are other examples where people may be like,

oh, okay, I see, this is actually short-term. Let me think longer-term.

I'd say the biggest one in workplace is focusing career and promotion together. And I think that

there's a perhaps a light connection between promotion and career addition. But I feel like

too many people are, at the moment we talk about career, they're like, let me talk to you. I want

to have a career talk with you. And I said, sure, why don't we find some time? We sit down together

and they're like, well, what do you think you need to do to get to career, to promotion?

And then I said, well, promotion is our system at this company to see you moving forward.

And it's pretty clear in terms of levels and what you're doing and what the process is and who

makes the decision. And that's pretty short-term because you can ask, hey, it's two years away,

how do I make it 18 months? It's a classic. But in reality, if you're looking career,

you're thinking about the sort of long-term arc and as I said, maybe the job after next.

And then you need to look at the promotion in service because how many people have you and

I talked to who said, well, then as soon as I get promoted, I'm going to leave.

So then I'm like, well, okay, then what's the promotion in service of? And you get into that

conversation, which tends to be a very long-term approach.

This makes me think about this interesting two-sided challenge with thinking about your

future career and where you want to go. On the one hand, it's valuable to think about

like getting more logos in your resume and working at Netflix and Meta and Airbnb and Ubra

there's power and value to that. On the other hand, you just keep doing that. And then what is

your life turning into? You're just chasing more fancy logos and feeling better about better brands

in your resume and stuff. This might be too big a question, but just like how do you advice people

to think about how important it is to get some of these companies in your resume and build that

side of it versus just doing things you actually enjoy and having a filling life and doing things

that are meaningful to you? Yeah, I mean, I think collecting labels does feel shallow to most builders

because if you're a product person, you probably got into the business because you like building

stuff. And frankly, not just product people want to do that. A lot of technical people want to just

build stuff. And then the question is, is the things that you're working on in service of

building? And then when you ask people, where are you happy as they always say, well, when I was

able to build this thing. And oftentimes they don't care whether it worked or not, which is kind of

ironic. So for me, when I see people chasing logos, I think about it as well. I'm actually

really a big fan of a diverse set of experiences that I think learning about

pre-product market fit, then seeing smoke turn into fire and witnessing and maybe shepherding that

and then taking fire and turning it into something great and being an experience set where you can

see the movie in these different frames makes you just a better builder. And so you can't really go

wrong if you're looking at those experiences and you're looking at inside the building problems and

outside the building problems, those are maybe consumer problems and distance to business problems.

The more diverse career you have, the better builder you are and that usually comes up being

satisfied. But the idea of just doing that because you think it's going to make your chances better

for the next job, maybe scares me and it feels very much in service of some future dream that is

not build oriented. And I think that can be leading to sadness. I love that advice. And I say this

often actually on this podcast, the power of diversity of experiences for so many reasons.

Maybe just to close this loop, would you agree there is a lot of value in having

one of these fangish companies on your resume? Like a lot of opportunity gets unlocked if you

work at one of these companies that people are like, oh, wow, okay, this person's interesting

or not. Or maybe overthink that.

Generically, the answer is yes. I think it's especially important for executives. I think

that many executives are hired because they are to bring expertise of the next phase of organization

to this company. So we're growing. We want to go after the next phase. We want someone who's

has expertise. The magma or fang companies, however you want to describe them,

they really have challenges and expertise at how to build things at scale. How to manage

millions or billions of users and customers. So the advantage is to be successful at that

is an endorsement. Having said that, those specific companies experiences can be substituted for other

later stage companies. But if you're coming in as an executive to bring someone to the next level

and you've never experienced it, it's a very difficult thing to get that executive experience

and to be like a C level for that cut growth company. The point of thing is no longer accurate

because Facebook is not meta. So magma is the term that you prefer. I'd prefer that. I think it

unfortunately kicks out Netflix. But it also doesn't pay homage to Adobe and Salesforce and a

number of other great companies. Fang doesn't. Okay. I like this. Okay. Let's try to make magma,

magma the new thing. Magma. Make that the title of this episode. Just joking. So the next area I

want to touch on is you wrote this kind of like hot take on something you call ex growth companies

and how it's not good to be at an ex growth company currently. So can you just talk about what is an

ex growth company and then why is that not a good place to be as a product manager for probably

any kind of role? I have a pretty strong opinion on this that I think that for 10 years we created

the hyper go blitz scaling type phenomenon. And there was a lot of good reasons for that,

some of which were just distribution platforms just got so good. You could take out Facebook ads,

you could grow with Google and you could grow in 18 months that maybe took previous companies 10

years. So I think that the idea was that all of these companies could instantly grow when they

found product market fit and that birthed all these unicorns. And then suddenly 18 months ago,

it almost like the music stopped, 0% interest rate went away and it became a lot, lot harder to

find growth through just fueling it with capital. And I think that the sudden change meant that

not only capital was harder to raise, but companies started to focus on their core products.

You've talked about it on this podcast, just how many their layoffs and restructuring and

managers moving to ICs and all of that work is happening. Well, the one funny pocket was there's

these large number of growth companies who have raised substantive dollars. So they're not going

to run out of capital in 2022 or 2023. What's going to happen is they actually have quite

long periods of time. So you don't see them raising new rounds, you don't see them laying off.

But in some ways, they're still hiring or they're still seeking the next product. The sad truth is

that many of their contemporary companies that went public are worth 10% or less than what they

were worth back then. And these companies are privately held and so they're sort of sleeping

in the shadows. And my fear is from a career point of view, so many tech professionals are in

these organizations or joining these organizations with the expectation that they'll make money on

their equity, that they'll continue to do fine. And my sense is we're going to see, even in the

second half of this year, lots of boards pulling back, taking their capital back, companies essentially

saying, hey, we're capitalized, like we're a scaled ocean liner, and now we need to go find

product market fit. But doing that with 300 people and expectations of hitting a multi-billion dollar

valuation just isn't going to happen. And so that's the reason why I'm like, danger, this is not the

company to join, this is the company to leave, find another phase times a wasting. And I worry

very much that people aren't getting the message. I know you probably don't want to name any names

of companies, but what are some signs that maybe you're at one of these companies?

I think that the moment that you are reframing the core product, trying to find that product market

implies that this company's valuation needs to be a pre-product market fit valuation.

So the two questions you ask yourself the day after we listen to this podcast is, hey, are we

scaling a product? We have customers that love us and we have a tremendous sucking sound, or are we

trying to find that customer sucking sound? And if the answer is we're still trying to find it, and

then you're like, is your valuation hundreds of millions or tens of millions? And if the answer

is hundreds or more, and you're still trying to find that sucking sound, you're an ex-growth company.

As a founder listening to this, I bet you're like, damn, we don't want people leaving. This isn't

the kind of message we want to hear. On the other hand, as an employee at a company like that,

is your advice just generally recognize it and then you should probably leave as soon as possible

because things are not going to work out for you? As an employee, I think you have almost no recourse

because you almost have to start over in terms of it's a new four-year investment.

I think that as a founder, you can recap your company. You can reset your stock price, you

could re-issue. You can make those hard decisions and you can maybe return some of the money to the

board and still continue, or you can pull the plug and restart the company that maybe you really

wanted to. But I think the founders in a better position, but they also have a lot more to lose

and far more constraints. But employees, if you listen to this and come to this conclusion,

a lot of times the listeners here have for more of their compensation is an equity.

And we just concluded that most of their equity may not be worth anything.

In which case, are you willing to take a half pay cut or work for 20% of what you can get in the

market? My question is, that seems to be quite concerning. The opportunity cost is just too

rich. An important variable in this framework slash piece of advice is product market fit.

This might be too big of a question, but just what tells you that something might not have

product market fit when you're at a company like this? What are signs to you and smoke signals

up like they may not have product market fit? For me, it's always around this pull,

sort of how much work do you have to do to basically generate pull?

So right now with open AI, for example, we're seeing ridiculous pull, but we may not be seeing,

for example, massive revenue or profitability. So that's the reason why I tend to feel like you

can kind of tell by how hard it is to acquire your users. When companies are putting very little in

marketing and there are people coming into the door or they're such an easy sale, you've got it.

And I think that this sucking pull kind of concept feels like the most appropriate way to

define it as opposed to the sort of unit economics of acquisition and time to pay back. There are

lots of mathy ways to do it, but early on you can tell how hard are you working to bring people in

the door. Is there any reason to consider staying at a company like this? There are counter

examples. I think the counterpoint is this is the biggest role that you feel like you could get

and you have an appetite to sort of learn at the, like I'm on the executive team,

I'm not going to get that somewhere else. That experience is career additive. I want that moment.

Great. Sometimes I see loyalty commit. This was my baby. I feel a commitment to the team,

the team that I've made, et cetera. I actually respect that. I think that you have to put bounds

on that. I think that you should have that conversation, but the learning position, the

loyalty tend to be the primary reasons to maybe delay the decision, but fear of finding another

job is a bad reason, but is it often common reason as well? Now that we've given many listeners an

existential crisis, let me move on to another question within the early career phase and then

I'm going to move on to mid-career. And I guess the question is just, is there any other piece of

advice, wisdom for early PMs? Maybe the question is what do you think they should most get right

in their early career? There's probably two answers that I would share. One is they want to build

something that they, as much as possible, are world-class in. So if you think about the different

types of product ambiguities that exist in industry, you can be a great crafter.

You could be incredibly strong at market ambiguity. You could understand how to navigate

markets and create something new that doesn't exist. You can be great at organizational ambiguity.

I know how to take complex teams that have complex goals and solve them inside the building

problem. You can be a domain expert. I'm an ML expert. I'm a really strong hardware PM.

You could be a team expert. I just really thrive in managing managers and I just know

how to get the balance right. So being a product manager means you're confronted with maybe all

five or maybe more of these. I want to know that you pick up one of these as early as possible.

So maybe you become an expert in domain. Maybe you become a great crafter. Maybe you really think

through how to manage growth. Growth is another one that I would add to the list. But picking a

lane is kind of goal number one. And then maybe goal number two is having a story to tell

to that next employer and that next next. What I worry about is sometimes when I'm in an interview

and you and I have probably done hundreds and you're talking to someone and then they talk about

those early jobs and they just sort of said they were there. This happened and it's very hard to

connect. Like tell me exactly what you learned and what you did. I want to know that story.

Just like Amazon talks about building the press release before they start creating a product.

Think about the story. Think about the skill. Then solve your day to day, your week to week,

your month to month, your performance review. That's my biggest advice I see.

I love that advice and it connects to your earlier piece of advice. Just try to get a variety of

experiences because that'll help you figure out which of these things is maybe best suited for

what you're interested in, what you enjoy doing. Yeah, absolutely. Awesome. So let's transition to

mid-career. Let's talk about promotions. You mentioned getting promoted earlier. We

chatted a bit about that. There's probably no one ever that didn't want to get promoted. It's

a common topic in people's career. But a lot of times people don't understand why they're not

getting promoted. They're not sure people are looking for to get promoted. You've promoted a

lot of people. You've gone through a lot of promotions. What would be your advice to give

people who are trying to get promoted and just haven't been promoted? What would you suggest

people in that position generally do? Yeah, it's a great question. I think that we want to understand

why and oftentimes asking your manager won't reveal the answer. So let me start with that.

I think that the answer of what you do is correlated with what's the real reason.

And I think that there may be, I'll suggest four common things I've seen that really hold people

back. And then depending on your environment, you have to decide how many of these apply.

So I think the number one is that you just don't have advocacy. You need someone to see the magic

in you to be promoted. And there is many of your listeners who have that magic,

but maybe have a manager or a promotion team. It doesn't always have to be the manager itself

who doesn't see said magic. And in that case, if you have the magic, you're in a bad setting and

you just need to change. That could be a shift within the project. It could find a manager who

sees it. It could be leaving the company. I think the second that's very common now,

Lenny, and I think it's coming up a ton, is the next rule doesn't exist.

So this is not as present in hyper growth because the next rule always did exist.

There was always growth. There was always hiring. There were always hiring people above you,

below you, et cetera. Now, I think there's lots of examples of people who are really qualified

and working at the next level, but the job doesn't exist. And so you can't really

create that job and ask them to be working at that next job if their position is mostly the

previous one. And that, again, I feel like it's not that satisfying because it means you're still

being held back, but it's radically different than if you're unqualified. These two are more,

the system is not in a position to advocate. The third is when you are being impatient.

And I think the hardest ones that I think I've worked with is the highest performers

have succeeded because they have set their goals to be more aggressive than what was

essentially average achievable. By default, we expect you to be two years in this role.

They're like, great, I'll see you in a year. And then they get frustrated when they can't

do that. And leadership takes longer to absorb. It's more soft skills. It's more subtle. It's

oftentimes it's based on impact, which is a lot of times lagging. And that tends to be frustrating.

And so if listeners are like, I know I'm used to being promoted annually, and now I'm a leader,

and I'm not moving as quickly, it's time for me to go. I'm like, well, maybe that's working as

intended. And so impatience is number three. And then the fourth one, I think is about 50%

of the cases where it's really there is a development area, but it isn't quite connected

to the individual. The listener has a development area. It's substantive. The manager is poor at

identifying it, perhaps even doesn't see it. But the promotion committee does. The individual

refuses to hear it, which is a very common one. Or they hear it, and they just don't want to change

it. And they don't do it because they're arrogant. They do it because it's like,

this is who I am. You want me to be X and I'm Y, and that's what a Y is, and I don't want to be X.

This is the hardest one, because this is where coaching and development and self-awareness come

in. Amazing. And this super resonates. So just to summarize, the four reasons you may not be

getting promoted. One is there's no advocate that sees your magic and understands that you're awesome.

Two is there's no actual role that's available. And so there's nothing to get promoted to. And

that's so true right now. They're like, everyone's laying people off. They're getting rid of manager

layers. I totally see that all over the place. Three is you're probably just not being patient for

you actually have some work to do, and you shouldn't be promoted. Maybe to follow the

thread on that first one, if someone doesn't see your magic. I see a lot of people just complaining

that I'm doing so well, I'm so great, and nobody understands it. No one gives me credit. No one

really appreciates me. I don't know if there's an answer to this, but is there a way to help

people see that no, you're actually not doing great versus you are, and people just don't see it?

Like what's a sign maybe? Maybe you're not as great as you think you might be.

The cheap answer is you have to get real feedback, not formal feedback. I think that the more

scaled a company is, the more they have these systems in place, which provide formal feedback.

But honestly, we've run experiments where we said, let's ignore the formal feedback. Let's

have a real conversation with my peers on how our teams are doing. The signal that comes out

are dramatically different than the formal feedback. What you're looking for when you feel

like you're in this situation where you're not being seen, and it might be because there's a

real issue, what you really want to dial into is, let me get the ground truth as to what people

are thinking. You have to have very strong listener skills, where we all have been in

the discussion where you're giving feedback to someone, and the next thing that they tell you

is they justify how you're wrong. You've missed this. Let me tell you about exactly why that

was a situation that you're using. You have to be great at pulling feedback, listening to it.

You have to triangulate it from people that don't see you all the time, that do see you all the

time, your peers. But you have to create an environment of safety where people feel like

there is no worry about retaliation or concern, et cetera. The more comfortable people are about

giving feedback to you, and the more you have the skills to pull it, and you don't trust formal,

or you don't trust manager, the better shot you have of truly understanding what that real

issue is and solving it. This reminds me of Jules Walter, who was on the podcast. He gave a bunch

of advice. I don't know if you saw that. I've had to accept feedback and get people to give you

feedback, and one of its pieces of advice is ask people for real feedback, and no matter how much

you're melting inside hearing it, just be like, thank you so much for that. Because then people

feel like, all right, he's listening. I think Jules is a great, probably one of the world's best

people in pulling feedback in my experience. I think that the one that even ones up it is when

I talk to Jules, Jules will look for feedback, then he'll repeat it back to me better than even

I presented it. Then I'd say, well, let me now feel safer to even provide, because anyone who's

explaining it to a place that they all not only internalize it, but they can articulate,

clearly understand and value it. That's the really powerful way is what you're saying is,

I just interrupt far too often. In some ways, it's almost to a point that it's annoying. Is

that a fair assessment? That's actually not the words I use, but that's what really gets people

comfortable in sharing with you what's really going on. Amazing. I think we're discovering

some of these people that have worked with you that have been on the podcast slowly,

maybe all around this topic. I didn't expect to go here, but in terms of other tips for getting

good feedback, is there anything else that just comes top of mind of how to get better feedback

from people? Because it's hard to do. Most people talk about getting feedback and then don't, or

they just don't know how. One is just you said, repeat back exactly what they told you and be

like, very appreciative. Is there anything else? I'd share out feedback. It's a little easier

when you are a manager, but for example, most managers that are listening have a staff discussion.

Maybe it's awkward, but maybe you have a stand up and you are giving notes to people. As a

manager, someone will come to me and they'll give me a piece of feedback. The next Monday,

when I have my staff meeting, I'll make a comment about something and I'll say, well,

a lot of this came because I got this great piece of feedback and I'll name the person.

I'm like, it really helped me see this challenge. Now, that feedback could be about me or that

this project or about the team and it might be positive. It might be constructive.

People hear that and they're like, wow, I get recognized for giving this guy feedback?

Sign me up. You're always trying to find a way to break down that barrier.

I love that tip. You talked about managers and how often managers are not great and managers,

maybe they don't identify development areas, maybe they're bad in other areas.

Maybe just a question here of why are managers often not great and then two, if you're a new

manager, I think a lot of listeners are maybe transitioning to management or about to transition.

What's your advice for being successful as a new manager?

I'll start by saying that in 100 years when the archaeologists look back and they see tech in

sort of early years of tech in the first 30, 34 years, they'll say that the biggest surprise was

how much we thought it was okay to not train managers. The military probably didn't make

that mistake for very long before they corrected it and most immature industries

really train managers. But boy, if you're a good coder, you are ready to manage.

That's the way the industry works. If you can talk, you are ready to product manage.

If you can product manage and ship something out the door, you should definitely tell people what

to do. I think that there's such a loose coupling between the skills to be successful at building

things and teaching people how to build. It's the difference between if you can make a good car,

you must know how to make the factory that makes the car. I don't think that's true at all.

I think that this is a massive epidemic that I think is just there's the thousand challenges that

stem from this, whether it's challenges around bias, challenges around enabling coaching and

teaching and solving development areas. My hope is that one day as an industry, we find ways to

improve and fix it. But podcasts like yours are actually quite meaningful steps. I would say that

your podcast might be more meaningful than most L&D departments and most organizations today.

That's powerful because you're having a tremendous amount of impact and I think that's

learning is essentially a lifelong opportunity. I think that is the type of resources that just

didn't exist a decade ago. I think to answer your question around what are the common pitfalls,

like if you're a first-time manager or listening or maybe someone who's considering it,

I think there are probably two quick things that I would say that you have to get

really thoughtful about as you enter into this journey. One is your challenge is going to be

to share the steering wheel with the person or the set of people you are managing. I think that

there's this three modes that people have in their head. They're like, oh, management is divide

and conquering. You go there, I go there, we meet up. Or they'll say it's like riding a bike

or teaching to ride a bike, I should say. Someone starts out on the bicycle, I hold your hand,

I let go, and then I hope that you fly. And I think it's more like the sidecar on the motorcycle

where a person's on the driving the motorcycle and I'm on the sidecar and whether I like it or

not, I'm attached. But I have this relatively specific role of giving counsel. And I think

that that model of how do you share the steering wheel, not just say, you got it or I got it or

I got it for a while and then I hand it to you, is the key question. And then I think that the

second miss that people tend to have is they tend to, because they have power, by the way,

organizational power, not because they've earned that power, they start managing whatever they

define that to be. And what I find is that you're more like the vampire knocking on the door of

someone you have to be invited in. You just can't walk through the threshold. And I think that no

matter how senior the person that is the manager, you have to earn the right to be the person's

manager. So maybe to be specific, if I start managing someone, the thing I'd like to understand

is like, hey, well, what can I help you with? And they can invite me in. Oftentimes, the answer is,

I don't need you. I actually wasn't excited about you as a manager. I don't need another layer between

you and the CEO. Get out. And I'm like, that's cool. Because anything I say after that is just

going to be annoying. And it's going to backfire. Now, one day, they will need help. And I will be in

the sidecar waiting to say, perhaps I can assist. And then when you finally get to that moment where

you're invited in, you pick an area or two. And then you really partner with that person on that

area. I can give examples on that. But I generally think that it's this invitation picking specific

and then making sure we're sharing the responsibility is the key kind of set of notes that I would

share with you. What's your take on the IC path, senior IC path? Something a lot of companies

talk about. I know Metta is big on this right now. Do you layering managers and things like that?

I find a lot of times there's a lot of talk about it. And there's not really a real career

opportunity there. I guess what's your just take on that as a real option for most people

trying to basically avoid the manager out and staying in IC PM long term?

Yeah, I think that it's a little bit more acute now because of the backlash that we talked about

between growth where management was perceived. So in this case, management was perceived as

a way to drive expansion. And so if you're in charge of expansion, you're managing the people

that are doing the build. And now we're doing a lot fewer things. And so I think that's what's

mandated this sort of growth in the IC track for lack of a better term. I think it is one of the

best things to happen to our industry. Because what's happened is in the last 10 years, and you

can tell I'm particularly hard on our managers here, they've basically been promising ICs that

early promoted into management. They didn't get taught. And now they're sort of average managers

and promising ICs. But now the story that they tell and what they've built is not awesome.

And if I'm looking to hire, if I'm in a growth company and I'm the next hottest thing and I'm

looking to hire someone and someone walks into the interview and said, look, I've managed two people

before. And then I was like in the charge of this thing, but they really did those details. And then

by the way, before that, I was like early in trying to get this thing out the door, and then they

picked me to be manager. I'm like, okay, that's an interesting set of experiences. I'm looking for

me in my company to build something. The next person walks in, it's like, I've been in IC for

that whole time. And during that time, I went from learning something to demonstrating it to

really being able to take it forward. And I got one of these ambiguities, master. I'm an expert

in domain. I'm an expert in managing organizations. I'm like, I don't need a team ambiguous expert.

That's not my hard part. My hard part is actually cracking the code on this complex market or this

very complicated organization where we have two teams that have different goals. You're the type

of person that I want. So I think, Lenny, to your question, I think the IC track is one of the best

things going to happen in people's career. But to your point, those tracks from a promotion,

and from an industry, how we perceive it, are hard to, they're not in cement yet. They're tender.

You wait six months, you wait, you know, nine months, they'll become very, very strong and solid.

And I think then we'll be able to lean very hard into them as a real promising track for builders.

So that's kind of your sense is this is going to become more and more real

as these layoffs have happened and kind of pullbacks on growth have happened.

Yeah. I mean, if you think about it, it's the reality in engineering and design. So in engineering,

you can be the sort of VP of engineering or CTO. And in a design, a lot of designers become design

managers, a lot of them stay as crafters. And then for whatever reason, in product managers,

maybe because there were managers in our title, we just all became managers. Like,

where about the product? What about the other side? So I actually think it's a bug

that has existed for a long time that actually we're going to correct permanently now.

I wonder if part of it for PMs is once you become a manager, this happened to me,

I didn't want to be an IC anymore is like that. I'm done with that. I really enjoy this management

layer. And I imagine with engineers, maybe they enjoy the coding. Like when I was an engineer,

I was like, that's really, I don't want to just sit around a manager. I just want to code. So I

wonder if there's any part of that. But a lot of your listeners like to build. And actually,

when they talk to their managers, they're like, I don't know if that job is awesome. It's like,

you spend all your time writing docs and telling your bosses, boss, like what, to justify resources

and headcount. Like, I just want to build stuff. I don't want to, you don't build stuff. So it's,

I think there might be some of that. I think that it's not perfect, but I think hopefully Builder

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Coming back to the manager life and how many managers are not great, and also just

how to get better as a manager, what have you found actually is effective in helping

new managers become better? I think I may have come across kind of hard on managers.

And I think I kind of said, hey, your manager, and your manager's manager isn't really doing

much teaching. Find the right podcast, good luck. And I think that that's a pretty

soulless answer. So maybe the way I describe it is, well, I think learning is changing,

and there's the self-service tools that are getting better, and then there's the structure

teaching, which I think is weak. And then there's community, which I think whether it's within

your company or outside of company, I think is the answer that we'll see more and more.

I think community as a way of creating safety, having authentic conversations, feeling that

you're not alone, that others are going through the same thing, and then sharing best practices

is so powerful. And what social software has done is it has really empowered community.

And now the tools are awesome. How many great communities have Slack channels or Discord channels

or Zoom calls? And we do a lot of that in the CPO community that I created. And whether you're a

new manager or whether you belong to a diverse group, whether you are new to a company, I think

that all of your listeners should be part of an active community where they can be very authentic

and very safe. And sometimes it's hard to do that with your coworkers.

And so you need to find another community. And fortunately, those communities are not the

easiest to find today. But I believe that the notion of community as a powerful

propellant for learning is the critical ingredient. And hopefully many people

are creating these communities so that new managers can find the right services.

Can you actually talk about this community that you've built? And this could be a good

time to talk about it. It's called a skip. Is that right?

Yeah. And it's funny. It's all kind of fun products. They were always a reaction to something.

They weren't really intentional. I, as you open the podcast, did really enjoy teaching and coaching.

I learned just as much from coaching others as they learned, I think. And yet I couldn't really

scale. And so I had this summer where I had just come off of being ahead of product. And I had

more and more of my people I was talking to were also ahead of products.

And what would happen is I would have these conversations and they would ask me a question.

I would say, well, that's the same conversation I answered on Tuesday.

And you know, what you realize is it's a very lonely job. Being lonely at the top is not just

an adage. They don't, and it's really, everyone's so busy now. It's like, how do you have time to

connect and everything's so single player? You don't really have community. And so I thought,

well, what if I took like the half a dozen people I talked to this month and I just said,

hey, all of you are all interested in talking through how to navigate this crazy world of

year one, year two, chief product officer. I think you would really gain. I know all of you.

And I think you can be safe with one another. Why don't we spend some time together? So we

did a WhatsApp channel and we brought a Zoom call. And this was during the pandemic. So you

really couldn't meet up. And, you know, we started talking. We started talking every month.

And people were so empowered by the fact that the problem they were hitting

was not just them. It was, you know, my crazy CEO is telling me this. And the next person is like,

oh, yeah, let me tell you what my person said. And then they would say, oh, my gosh, that sounds

worse than my situation. But then we would sit down and say, hey, the third person said, I actually

kind of had this and now I figured out a way out. And here's what I did. And you're like, wow,

that's amazing. I'm going to try it the next day they come back. They're like, it works. And we

started to connect and we built this trust. And community building is interesting and powerful

work. And so six went to 12 and then 12 went to 15. And now we have 28 members. And a lot of folks

are interested in these types of communities. But I'm so worried about scaling it because it's

the enemy of trust and authenticity. And so for all of you that are building communities, it's a

tree balancing act. But I do think that the goal is to find ways to take all of these sort of like

minded folks that are in these same situations and connect them together. And late stage chief

product officer happened to be one of the ones that had some of the most substantial

importance to me because of all the coaching I did for that group.

If someone's listening and they're like, oh, I need to join this thing, how do they find out

about it? How do they potentially apply and try to join? Well, we have enough members now. There's

a LinkedIn area called the Skip CPO community. And you should contact any of the members that you

know and ask them to join. And my request and my requirement is that they are number one product

leaders in their organization and a company that's not early, but that's mid to late.

And the reason being is those sets of problems tend to be the most similar. To be honest, I think

this is not the only community that I want to be part of and help create. But this one happens to

be the preexisting one. I think there are lots of powerful communities that can be created. But

this particular one is very much focused on the Skip CPOs. Awesome. I'll mention the community

around my newsletter just so folks are looking for a community to join. I try not to promote these

sorts of things, but it's a good time as well. If you're a paid subscriber to my newsletter,

there's a Slack community you get access to. There's about 12, 13,000 people in there. There's

meetups happening all over the world every month. And it's amazing. Very proud of it. People are

getting a lot of value of it. And it's basically open to any level of product manager or other

function they're in there to. So it's a very different sort of experience. But

we'll link to that also in the show notes if you uncheck that.

And I think that that would be my put because so many of the managers will say,

hey, I'm an IC. Here's a great one. I am not being told I have the next job. I just was told to

become an IC and I was a manager. I feel like my learning opportunities are stuck, but this is a

bad time to look for a job. They should be in your community. They would learn more

from that community than they will learn from managing one random person that they were attached

to managing in some project that may or may not see the light of day. Yet that's how our society

is programmed. Our industry is like, no, no, go manage that person because that's going to make

you closer to the top. Forget learning. And I'm like, well, learning isn't happening. Learning

is happening in your community. Learning is happening in our communities in general. That's

why I'm pushing so hard on this. And this is a good segue to talking about the third bucket,

which is kind of later career, CPOs. That's the segue in my mind there. Something that I've heard

you talk about is that a lot of really senior leaders have real development areas, but they're

hiding behind these superpowers that they have. Plus, people don't like to give real feedback

to senior people. And so I'd love to hear just what you're seeing there and how maybe people

can work with that through that and what we can learn about that issue that you've noticed.

This came from my notes as I was talking to a therapist on this. They talked about the

shadows of superpowers. And I thought it was an incredibly powerful phrase that everyone

focuses on your superpowers, but no one ever thinks about what shadows they create.

And shadows of superpowers to me is the story of a lot of executives. There's an adage that's

thrown around, which is what gets you there isn't what got you here. And it's sort of the tools

that have made you successful today. You need to almost rebuild or relearn to get to the next phase.

And I think both of these sort of speak to the same point that oftentimes people have a great

superpower. They go into a performance review. A person says, you know, you're getting some

feedback from your peers that you struggle in collaboration. And, you know, the manager even

sometimes is puzzled, but the individual will say, are you kidding me? My last five performance

reviews told me that I was one of the best collaborators in the company. How in the world

is that possible? And then what you realize is that, well, you're collaborating as long as

people agreed with your point of view. Now, as a leader, we're asking you to be opinionated.

And because you just think you're an amazing collaborator using the exact same tool set.

And it turns out that when you're dealing with senior people that may not even be in your

function, they may not be product, they may not be tech, they recoil. But you're moving so fast

because it's your superpower, you would never think that this needs to be rebuilt. And sometimes

it could be more extreme. You know, great collaborators sometimes are very reticent to

present their own opinions because they're so good at assimilating others or people that are

amazing at growth struggle to be innovative. People that are world-class storytellers struggle

to get in the details. People that are very taste maker-ish. They are always the first

to have point of view. They don't necessarily introduce change particularly often.

You know, you're strong politically, but your decisions are unprincipled. You're a structured

thinker, but blue sky innovations are very tough. You're an amazing listener, but you're very weak

to be decisive, right? So I can go on forever. And what I would say to you is sometimes even in a

30-minute conversation, walking into the room, just knowing what I know about the person,

I can unlock their development area faster than anyone ever before simply because my secret is,

I'll bet you because of this person's world-class here, these are the three things they're going

to hit and they don't even realize it because it's their identity. This is what got me here.

If you make me work on that, you will make me change my superpower. And I'm like,

that's why you're stuck. That's why your career is plateauing. And then they get sad

and then they take a long time to process and then the work actually begins and then they

solve and they go. And almost everyone, once they have the name in the face, they are able to solve,

but the face in the name is hard when it's sitting in the shadow of superpowers.

Wow. That is an incredibly important point. For someone to recognize this, do you find that

they need someone like you that's like a coach, mentor, person to come in and be like, here's

what I see? Or is there a way, I guess, as someone that's a peer or an employee to help them recognize

this without them shutting down and being like, no, shut up. No, you don't need a coach. What you do

need is to listen to contradictory feedback. So what was the premise here is you're being told

that something that you hold as your strength is actually in your way or a development area.

Do not dismiss that, recognize most likely you're doing it correctly. You just have gotten to the

next level. So what I'm hoping the listener does is it goes back through all the feedback that they

may even have and then looks at all the discard stuff. What's on the discard pile? Things that

were discarded are anomalies because they're artifacts of my strength and often your managers

are the ones that do the discarding. That was just a weird, that person and they were just into it,

you know, they have it out for you. They got reword and they were upset. I'm like, no, no, no, no, no,

perception is reality. Talk to me about that one. That might be it. That's what I'm looking for.

Fascinating. This makes me think about companies that have the same issue.

Companies' strengths, like say, Meta, for example, move fast and break things and then,

oh, that ends up being the biggest Achilles heel. Uber, similar, Airbnb has similar challenges

like that. Absolutely. This exact thing applies to relationships. This applies to companies.

This applies to a lot and I'm so happy that I was able to learn about it and frankly,

it was a critical unlock for me because it took me, I was stuck on something for years

and I just could not understand how, for me, it was, I was very opinionated about something

and then I realized being loosely held on my opinions didn't mean that I became a weaker

executive, but it was my opinions that got me to be so successful and it required me to rewire

who I was as an executive. That took a lot of time and a lot of energy, but it came from this

realization and then I started to apply it for other strength areas. Now, every time I have a

strength area myself or those that I coach, I immediately talk through all the things that

I bet you exist and most of the time, we're right. What is it for you that you said was your

superpower and your shadow? I think that I was, as an entrepreneur, very opinionated about using

small amounts of information to make decisions and then I was very good at driving those things.

When you come an entrepreneur, you're great at grit, you're great at opinion, you're great at

being decisive and then as an executive, you spend a lot of time making sure everyone has

context. Everyone is heard. Your opinions are actually edited for the collective for good reason

and it's not just to be to placate, it's actually to improve, but as someone who's basically been

right a lot, that requires almost to complete and you're like, well, that's not who I am and I'm

like, okay, you start with the sentence like that's not who you are. You're definitely doing it right

when you hit leadership. What was the process like for you to work through that? You said

it took a long time. What made it effective for you? Was there a coach involved, something else?

I got a lot of setback. I get a lot of negative feedback. I had a lot of abrupt challenges at

work where folks would say, you're not collaborating well, your peers don't have the same level of

respect as they should and I was like, are you kidding me? That's not who I am. These things

that are being said about are completely wrong. I was very much struggling and that's when I said,

you know what, I can struggle and blame others, but what if they were right? I'm going to be doing

this for like 30 more years. It's kind of worth it to figure out if they're right. If they're wrong,

then you don't lose and that's what kind of forced it and then the tooling starts. Then you start

talking through, you know, my self-awareness was strong enough that I was able to say, okay,

now that I understand it, I had some peer feedback that helped bring it home from someone I trusted.

So that was like a kind of a linchpin to this, but these are tough, tough things to break through

and oftentimes they don't come nicely, I guess is the point.

I was going to ask what that turning point for you was and it sounds like it was

direct feedback from someone you really trusted that's like, oh, I really need to take this seriously.

You got it. You got it because I had a lot of feedback that I was dismissing and then I had

feedback from someone I'm like, that person I should listen to because they're giving me the

feedback for the right reasons and they have the right language. It comes back to the power of

getting feedback and getting good at that. And making people feel safe and giving it.

This is a good segue to maybe the last question. You told me once that a lot of the people that

you work with that have kind of made it have a lot of mental health challenges that they didn't

expect their life to be the way it is necessarily when they got there. Can you just talk about what

you see there in that group? Yeah, this is a story that I don't think is told very, very well right

now. And partly because it's such a luxury problem. It's almost a little embarrassing to discuss it

often. So many people struggle with so many basic needs, going through layoffs, going through all

these challenges. I mean, these are real issues. But I think that what I've noticed is that if you

kind of break career as we've done in this podcast between act one, act two, and act three,

if act one is sort of learning and being that sort of builder and then maybe building the car

and then act two is building the factory, act three is like, what's after that? What do you do

after that? And I think that act three in the past wasn't as long as it is now.

Before, people would proverbially retire in their 60s when they used to actually physically work.

Now, almost all your listeners sit at a desk all day. So they don't need to retire by any means.

And health is getting better. You might see folks work until their 70s or 80s. So that means that

their careers are potentially 60 years long. So even if you're 20 years or 30 years in your

career, you're only halfway through. So this act three could be a thing. And I don't think we talk

about act three enough. And what often happens is, and this is what I've been watching for people

that are at my age, is they sort of succeed and then they become lost. And they almost goes hand

in hand. So when I was a kid and I was growing up in the Midwest, you know, entertainment was like

going to the dog tracks and not even the horse tracks. We didn't have horses. So it was the

dog, Greyhound dog tracks. And so people would, you know, bet on a dog and Greyhound would go

around the ring and then you would see, you know, I bet on number three and I'll make a buck or

something. And the way that they motivated the dogs was they had these like fake rabbits,

which sounds kind of cruel and horrible. So I don't want the SPA to come after you. But the

point is that they'd have these like fake rabbits. And what was interesting is the moment that the

dogs, if they accidentally touched the rabbit, the, you know, the sort of the tail, you know,

because the machine broke, because this, these tails would go around faster than the dogs,

which would then motivate the dogs to go around in circles. Sometimes the machines would break.

The dogs would actually catch the rabbit. They would never run again.

And the reason why they wouldn't run again is because there was like, well, what's next?

I've achieved what I was looking for. And so I think this happens a ton is like your listeners

are spending time focused on like, well, one day I will be X, I will be that vice president,

I will have more money, I will have built something, I will have started a company.

But they don't think about like what happens next. And when it happens, when they succeed,

their North Star, their entire way of wiring their career themselves,

it has been around like getting to that place. And I think that if you're going to get their 30

years in and you have a 60 year career, a lot of the discussion I've been having with myself

and with others has been probably need to start working on that North Star now.

What's the second thing? What's your career next look like? How do you ensure that you are

always going to have something important and motivating to do with your career? Otherwise,

you'll keep working because you don't know anything else to do, but you'll be sadder,

or you'll find ways to create war when pieces need it, or you'll spend money in an attempt to

sort of earn more, and or you'll find habits that are bad. And I really want us to have long

60 year or 70 year careers, not just 30 year or 10 year, which is why I enter this into the

vocabulary out there. That is really resonating with me. I had a similar experience. I had a startup,

and my whole goal was just like, I just want to start a company. That's my goal. That's all I

got in life. I want to start a company and then maybe sell it, maybe go somewhere with it. And so

I did, and then we sold it to Airbnb, and then I got to Airbnb, and I was just like, what the hell

do I do now? I don't have any other goals. And it was pretty, pretty sad, exactly what you were

describing. It was just like, I guess I'll just work here, and I don't know, maybe I'll start another

company, but that's not a, I already did the thing I wanted to do. Your story is, I think,

very inspiring, because what you did is you said, I think the thing that I want to do is give,

but I want to do it in my own way, and I want to create something. But I want to do something

that I think I can do for 30 years, and I want to do it, and it has lots and lots of spokes to it.

And so you reinvented yourself professionally, but you created a new North Star. My sense is for

every one of you, Lenny, there's a hundred that could do that, that could do giving, that could

do things that could scale, but that end up falling into what got them to be successful in Act Two,

and they get stuck. And so this is reason why, like when you hit your skip, keep looking for the

next skip is the point I'm trying to make. And I think you're an inspiration for a lot of folks

who have seen you transition and realize, is life after just being a tech professional

entrepreneur, there's got to be ways to do more of this for all of your listeners. And I think

it's never too early to start thinking through it. It's actually quite powering to think that you

have such a long career, you can make mistakes, and you can do some amazing things down the road.

Yeah, this is my fourth career is what I realized. I was an engineer, then a founder,

then a product manager, and this whatever this is, whatever this is, whatever this is.

I guess just to give people something inspiring, productive, what are maybe some examples of

North Stars you've seen that people can evolve into? I guess one path is this path of content

creation, helping people learn stuff. What else have you seen that might work out for people?

I think that all variations here come into two categories. One categories are

ways to drive more scaled economics. I've made millions. My North Star is to now make it tens.

I've made tens. My North Star is to do hundreds. That's what drives people from

its non-entrepreneurship, its investing, its non-investing, its private equity, etc.

Whether we describe that as a bad quest or a good quest is a decision for your listener.

The other arc is around giving. Eastern philosophies that have been around for thousands

of years talk about this as the end state of happiness. I think that maybe to be provocative,

I think that it's okay for you in Act 1 and Act 2 to not predicate yourself around the notion of

giving to others because this is maybe the time on the planet where you need to take and you need to

create. Boy, if you're going to work on an Act 3 and you have 30 years, regardless of where you

are economically, if you feel like you can take that off the table, if you can find ways to give

however that means to you, however that translates to you, is that content, is that volunteer,

is that starting a company that is more mission-based, that is not my role. But I think that if you

were able to do that for 30 years and be giving, not only is that going to be more fulfilling

than your Act 1 and Act 2, but it's tremendous for society, very empowering. And that's where I

commend you because you're giving through your passion, but also making a livelihood.

And I think that that's a very powerful blend that is hard to achieve in Act 1 and Act 2,

giving constraints, and that's the liberation that Act 3 provides.

What do you think your Act 3 plus ends up being?

You know, many have asked me about this. I would say that I'll use the word and then I'll tell you

I won't use that word. So it is around my passion, around coaching and giving to others.

But because I'm a product person, because I've seen success in building products,

thinking about scale, thinking about community, I definitively plan to devote my Act 3 towards

coaching and giving to others and lifting up those that with the right advice at the right time

can change their trajectory. But scaling that and doing that in a way that is very authentic

is really the hardest part and it's a product problem. And so that's what I'll devote 30 years to

and, you know, I look forward to that every day.

That is beautiful. That feels like an exactly correct fit for you and I am here to help

you on that journey anyway, Ken.

Thank you, my friend.

Absolutely. Is there anything else you wanted to touch on before we get to our very exciting

lightning round?

No, I just appreciate your generous offer to have me attend and participate in this wonderful

podcast that you created.

It's absolutely my pleasure and it's not over yet. We've reached our very exciting

lightning round. I've got six questions for you. Are you ready?

I am ready.

What are two or three books that you've recommended most to other people?

So two and both business books. I'm sorry, I'm going to come across boring, but one is

this sort of little bit of an old school book called Crossing the Chasm by Jeffrey Moore.

I don't know if other speakers have spoken about this, but it's a book that Jeffrey Moore wrote

and it's a book that really talks about how to get your first product on base.

So it's this concept of creating a beachhead. And so I like that concept.

It's so marketing is something that we don't talk about enough in product.

And then the second one is a book that none of your listeners have actually probably heard of

called Leadership and Self-Deception. And it's a six hour audio that I highly recommend.

And it's a story about a person who has hit a wall and who's getting all this feedback that

they don't know what to make of. And it's around their mindset being stuck in a box

that was very powerful when I listened to it in my late 20s.

And so I encourage all of your listeners to grab that one. It's not one that anyone normally would

hit, but it's a fun story. It's a good ride. And I think maybe you'll get something out of it.

I have not heard of that second one. I'm excited to check it out. I have Crossing the Chasm back

behind me on that shelf somewhere. And you talk about how marketing isn't something

product leaders and managers think about enough. And I have many marketing-oriented guests on this

podcast and those episodes do the least well. But I'm just going to keep doing it because I

totally agree with you. I think there's so much to learn from marketing and it's connected to

growth, which is connected to product. So I agree. Yeah. And I think that marketing is a language

of connecting products with people. And that is what a product manager does. But we often

lack the language. We lack the thinking around how to explain it. And yet we spend all our time on

data and features. Boy, the diversity of having both playbooks can make one just a much more

powerful builder. So I agree with you, though. Marketing folks are probably some of the best

content in the least to listen to. So maybe that's a plug for people to go back to this episode.

100%. That's what everyone should do. And I don't know if you know this, but actually,

at Airbnb, the product management function has been renamed to product marketing.

So all the product managers are product marketers because Brian is so big on,

you're not just building product. Your job is also to make sure people use it.

And we'll see how that experiment goes, but that's a bold move, I thought.

Very much so. Very much so. But it's an homage to this concept.

Exactly. Okay. Back to our landing ground. What is a favorite recent movie or TV show?

I'm a huge sports fan. So I have tickets to the Warriors and the Niners and I am a big Bay Area

sports fan. And Giannis is my son's favorite player. He's a basketball player for the Milwaukee

Bucks. And they have this Disney Plus story called The Rise Story. And it's a story about his

childhood and how he struggled to find notoriety and how he made it into the professional leagues.

It's a great Disney Plus family show. And it's a great kind of zero to hero type thing. So I

love that story. I feel like you're going to have a really good answer to this next one.

What is a favorite interview question that you like to ask?

I like the format of what's something that everyone takes for granted that you think is

essentially hogwash or inaccurate. Sometimes I'll ask a manager, look,

you've managed hundreds of people in your career what's conventional wisdom that you

bet against that you have found actually inaccurate. And you could do that for what

do people think about AI that's inaccurate that everyone believes. You could do that for

domains. You can do all kinds of things. I love it. Is there something you specifically

look for there or is it just depends on what year? I'm always looking for people to break

this sort of interview mindset. So everyone always prepares for interviews and then their

entire conversation is predicting what you think you want me to say. And as a result,

you can have high quality people that you dismiss because they weren't genuine. There's no way to

answer that question without being genuinely opinionated. Because it starts with what is the

thing that you think I want to say here and then tell me why it's inaccurate. So when I break that

wall, I'm testing as this person authentic because sometimes I'm dismissing them because they told

me nothing new. But I don't want the interview process to penalize them. And this was my save

question. But I can't use it now that I've told everyone.

It's going to be all over TikTok soon. Everyone's going to know this.

Next question. What's a favorite recent product that you've discovered that you love?

The geeky answer in me is the Arc browser, which I think probably a lot of folks are starting to use

in that you're a listener. Part of the reason is I think it's just great for folks that have

hundreds of tabs. And if you work at a scaled organization, you just have lots of tabs.

But I think it's also as a product guy, I thought Chrome was pretty good. And they've got

like gajillions of people using it and billions of installs. And so at some point, you kind of come

to the conclusion that this is probably good enough. And then you see a product obviously built with

a much smaller team. And you're like, huh, there actually is opportunities to innovate.

And anytime you see a innovation on something that's mature as a product person, I think that's

just fascinating. And I was just blown away at how they created something that's better than

something I'd hold as a tourism. Yeah, we had Josh on the podcast. We talked about a lot of

their philosophies. And on the tap thing, I think the key there is it closes your tabs after 24 hours,

unless you put them in a specific place, which I love because I didn't was like,

like you think you would do that, but you don't. And then it's like broke so beautiful,

you wake up in the morning, everything's gone. But you can save stuff that you want.

The other thing I'll mention with our, by the way, also a huge fan to all use,

is and I'm not an investor, just a fan is the onboarding experience is like the best onboarding

experience I've seen. I was just like, like I did it. And it's just, I got a tweet about this. This

is so good. And actually, if you go to that episode, there's a link to get past the wait list and

oh, that's great. Yeah, he gave me many thousands of invites. Okay, keep going. What is something

relatively minor you've changed in the way you develop products and your team that's had a

big impact on the team's ability to execute? A little bit of this is just because of scale.

But oftentimes, we think a lot about the products and the features and the decisions that we're

working on. And then we think that meetings are a nuisance, or it must have necessary evil to be

able to deliver. Sometimes I realize that at a scaled organization, the meeting operating system

is as important as the products that we're building, because it sort of speaks to how we scale and how

we ensure we have the right degree of delegation, the right conversations, and then the right

acceleration on the right decisions. So what's interesting is every quarter in my current teams,

even in my past teams, I talk about our meetings like a product, like we're on version seven in

my team. And so we're like, Hey, version seven, every 90 days, these are the meetings, these are

the discussions, this is how we organize is the attendees. And then here's how we make decisions

to the cadence of the week. This is when people can work from home, hybrid, whatever it might be.

And then I take feedback two months in and then every three months we make another round.

And what it finds is that people then can plan and they can make meeting time effective. And

meeting time is such precious time. It's the most expensive time in a company. So when I was in a

startup, I couldn't imagine doing this. But now this is like my bread and butter as a leader.

It's the process part. And frankly, for new folks that are new in leadership positions in a new

company, it's the one thing you can do when you have low context. When you don't know how the

product works, you can look at things with fresh eyes and see inefficiencies when everyone that's

been in the system can't see it. So I'm a huge fan of rebooting meetings first. So process first,

then people, then product, then strategy is sort of the notion I make. And this is this

first thing I always do. Final question. What is one thing every PM listening should do

to help their career? Ensure that the story you will tell about the work you're doing today

is meaningful for your skip job. So if you sit down and you write down

in six months, in 12 months, in 24 months, when I achieve or finish this role,

here's the paragraph I'll write. Here's the problem I solved. Here's the skill I built.

Here's the headwind I faced. Here's what I did to overcome it. Use I in the sentence. Do not use

we. We will do good things. You are who we are thinking about your career. We're not looking

for we. Master the story now. Understand the story. If the story sucks, you probably should be

thinking through how to make the story not suck. But that to me is a very good career decision.

And I think everyone is building their story today. I want to know that story. I want that story to

be incredibly compelling. Because whether you promote it or not, that story is compelling.

You'll be promoted in career. And that's what we're for.

Michael, this is the first time we've ever met. I'm such a fan instantly. This might be my new

favorite episode. I'm so excited for people to listen to this. There's so much value here.

Two final questions before we wrap up. Where can folks find you online if they want to learn more

and also talk about maybe various community skip and all that stuff that people can check out.

And then how can listeners be useful to you? I'm building this brand around the skip because I'm

so passionate. There's two outlets that people can easily connect. One is the podcast, which

much like yourselves is available on Apple and Spotify and others. So I'd love for people to

join my podcast in here. What I'm now moving my podcast to is almost like coaching calls.

Because I have so many of them, I'm saying like, hey, 30 minutes, let me walk you through a problem

and hear how I'm thinking about it, whether it's a transition discussion or compensation discussion,

et cetera. And then the other one is this newsletter that I have on Substack, which is a

bit of a mirror of the podcast. It's different forms of the same topic areas. So I'd love for

your listeners to connect with that. I think as far as getting in touch with me, LinkedIn is where

I spend most of my time professionally. And so between Twitter and LinkedIn, my presence is

relatively easy to find. And then how listeners can help me. I mean, one is one, you can build

the most fulfilling career story and be your best, but also give back and pull others forward,

whether that's through your Act 3 or whether that's just helping others. I mean, I think that

would be the most fulfilling to me. I think feedback from your listeners to me on things they

wish I would spend time talking about is incredibly empowering for my content. Because then I can

deliver more meaningful content and it's very different from yours. But I think it's all around

the arc of trying to help people gain forward and be more effective tech professionals. So

I would love to hear from your listeners. Just to make sure people know where to go to do this,

for feedback, do you recommend LinkedIn? Yeah, LinkedIn is the ideal. But you can also find

me on Twitter if you're just trying to add a quick, if you're trying to follow me, follow me

on LinkedIn. If you're looking for feedback, just tweet me. And then for the skip newsletter, what

is the URL to go check that out? It's theskip.substack.com. Amazing. And you don't publish often,

but each issue is incredibly valuable. So we'll definitely link to that all in the show notes.

Mikkel, thank you again so much for being here. I will let you go now. And this was amazing.

Yeah, thank you, Lenny. Appreciate it. Bye, everyone. Thank you so much for listening.

If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your

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Machine-generated transcript that may contain inaccuracies.