Why You Should Not Go Into Product Management

Really excited to be here.

So, you know, I’m a civil engineer by training, environmental civil, and then I became a nuclear engineer. But I ended up at the startup, Plumtree Software, and first running QA, then running engineering, and this guy that ran product, Phil Sofer. And every day, I told him how he was doing his job wrong. I was the receiving end, building stuff. Right? So I just told him this every day. And then one day, he decided to move on to leave Plumtree. And he told the CEO, I had to run product to, like, get back at me.

Right? I didn’t wanna do it. I was like, my job’s too important doing engineering. I can’t give that up. But once I got into it, it was incredible.

the thing is, you need to build things that matter. Right? The way I got into engineering is I was in QA, and there was this engineer, and his stuff had so many bugs. So I went into the source control system, and I started to figure out the bugs. Right? And he locked me out of the source control system. So I went to the CEO, and I’m like, I don’t know what to do here. I want this code to work. So he fired the guy, and he told me to write it.

He was a very, like, big hearted guy, but he just didn’t want that kind

into this world through, like, weird ways, so I didn’t understand the job. I felt that the engineering part was more important, but I couldn’t work on things that didn’t have clear customer value, weren’t thought through, and the and, like, Phil was amazing. Amazing product manager. But it’s easy to critique what you’ve never done. Sure. Right? So everything coming over the wall, was like, these things don’t make sense. And I was like, you have to define these things upstream or else we’re gonna go down dead ends.

I think it’s a superpower. I’m not a CS guy, but I ended up being, like, an architect at Plumtree Software and, like, running engineering at a bunch of places. And it’s because I don’t know what I don’t know. Code is not complicated. I can’t write it well, but I can understand it. You can look at it as just a logical system. I I’m a systems engineer initially. So it’s not hubris. It’s just curiosity.

You figure out a way to solve a problem, and everybody thinks you’re crazy. But then you just don’t really have time to absorb that. There’s a saying, if something’s impossible, don’t stop the people doing it. It was said much better than that, though.

I think it’s it’s it’s walking yourself down their vision and then vectoring their vision into your vision. Right? So people come in with a point of view about your product or their business. I use the same methodology for, like, everything I do, and it’s just to go in knowing nothing and then interrogate the person until you feel like you could do their job. And so you really understand, like, they they say I did this, this, and this, but you can’t figure out how they got from here to here.

Keep asking questions until you figure it out. And then you get a picture what they’re trying to achieve. But then you’re like, well, the why behind it. They don’t wanna do all these steps. They just wanna accomplish a job. Sure. And then you say, okay. Well, they articulated a lot of pain in these steps, and you have a point of view that totally different from what they said. And then you kind of, like, try to tease the best imaginable out of them so they say what you want them to say.

I mean, I’m a human, so I’m terrible at customer questioning. It’s impossible not to lead the witness. It’s really, really hard. Yeah. I’ve been doing this for a long time. I I like to have other people that I know on on calls, and then I ask them for, like, notes of when did they see me. One of Ali’s cultural values, but I I’ve kind of internalized it, truth seeking. You wanna get at the truth. There’s all the biases, confirmation bias, blah blah blah blah blah. So the open ended questions.

But the problem is open ended questions oftentimes you can’t get to where you wanna go. Alright? So then it’s just like open ish questions that are kind of leading. How would it feel if it happened this way instead? Rather than like, let me talk at you and show you a demo.

So people like to talk about being customer obsessed. Yeah. But I think of there’s the customer, and then there’s the collective customer. So you have to be collective customer obsessed. You never wanna overfit to a customer because then there’ll be a tiny TAM. Right? Customers, well, I never listen to them in terms of how the feature should work. But what they need to accomplish, suss out if that’s a common need from your collective customer. Because if you’re serving one customer, if you’re obsessing about one customer but it’s overfitting, you’re

There are a lot of conflicting inputs. It’s funny because a lot of people come to you wanting to go into product. You know? We’ll get into that. Yeah. And as you know, I try to dissuade them. But, basically, if you’re rocking it as a product manager, everybody thinks you suck. Think about it. Okay. Your stakeholders are there’s customers, there’s field, there’s engineering, there’s business finance. Right? If sales loves you, engineering hates you because you’re chasing deals and you’re not thinking about the long term future. If engineering loves you, sales hates you because you’re just doing long term stuff and you’re never helping them close a deal.

Like me, when I I was talking to Phil Sofer, everybody thinks they can do your job better than you. People come to me and they’re like, I could do your job better than you from all functions because they’re so frustrated with the path you have to take in order to juggle all the different constraints. And why

It might sound goofy, but have ever read Letters to a Young Poet by Real quick? I haven’t. Okay. The argument is don’t write unless you have to because it’s miserable. People often think, I wanna be a product manager. I’m the CEO of the product. I’m the GM. I call the shots. I can tell people what to do. I can create something. I can be, you know, Johnny Ive. I can create this beautiful thing, and everybody will build it, and customers will love it. But that’s not what the job is.

Right? It’s

a way to make baby steps towards the vision while staying alive, basically.

Yeah. And the fact that you have unadulterated agency. If I’m talking to someone that wants to move from another function into product, the main thing I try to figure out is, are they doing product now? If you’re an engineer and you’re not involved in the PRDs and let’s say you’re in the field. Right? You’re a sales engineer. You’re harping on engineering and product all the time to fix the shit your customers until you see it working the way you want and then you’re doing product management.

But if you can live as a sales engineer or an engineer without doing that, if you can take the spec and build it without fighting, you can never be a so if you cannot not product product manage, manage, then you should be a product manager.

No. I think that, again, they might not have had the title, but have they done it? How do you tease that out in an interview? You ask them where their biggest impact was. And if it has nothing to do with product. If it’s like calming down an angry customer, but it has nothing to do with the value of the cup you know? So you just tease it out and

Yeah.

it’s a complicated topic. Right? You Brix used to have this value called data driven, where we want everybody to be data driven. But it has a dark side because you can weaponize data. Right? You can argue any point of view with any set of data if you’re clever enough with numbers. Sure. Right? So we we modified that to be truth seeking because the point of being data driven was be truth seeking, but truth seeking defangs the dark side of data driven. Sure. So when let’s say you’re gonna build a product.

You wanna, like, ship early, ship often, but how can you figure out the early signal if it’s not revenue based because maybe you’re not charging it of whether or not it’s working. Right? And you come up with a KPI and you can set goals and stuff like that and you track that. And we could talk about that for days, input metrics versus output metrics and things like that. But the key is as soon as you start, like, reporting on it, it becomes the goal. So the data in your progress serves one purpose, one purpose only, which is to figure out your blind spots and where to ask questions.

The goal is not hitting your target. The goal is seeing where you’re varying or going way above your target, why? And then you can dig in and figure out if you need to course correct or not. A lot of times, the right thing to do is change the target. The target was wrong. Like, you came up with a target when you had a point of view and hypotheses before you’ve shipped, and then you disprove those and adjust the target.

Well, I mean, that’s another funny

Okay. So if you’re a startup of one, then continuously. You’re continuously doing the loop of hypothesis validation. No. I’m wrong. I’m an idiot. Gotta change. When you are a company of 6,000 people, you gotta be very careful. There’s a lot of grumpiness to do it more frequently than annually just because a lot of people have built up flywheels that are organizationally complex to hit the goal. But then again, if it’s existential, like, why would you wait? Why would you do something stupid for six months because you have annual goals?

It’s speed everything.

Like, speed of learning is everything. But that doesn’t mean shipping. People talk about one way doors, two way doors, type one, type two decisions, all this stuff. Like, the key is maximizing your learning curve. And there’s so many clever ways to do that, and a lot of it feels slow. You wanna know why you are doing the next step, you know, before you do it. But then sometimes, you can’t figure it out that way, and you just need to try. And that’s when, you know, ship things that you might throw away and do it you know, don’t scale prematurely, don’t overarchitect it, get the learning in.

Because they get the they let the data be the thing.

I I think that’s it. Because here’s the thing. I’m just as bad at this as everyone else. Like, I have these dashboards. I build a lot of dashboards. And if there’s something I don’t understand, I like to do data science until I figure it out. And then I look at these all the time. This morning, I got up. I looked at some dashboards. Am I gonna do anything with that? Tell it to fucking waste of time. It’s like infinite scroll. I wanna see if the next bar is green or not.

I have, like, this dashboard where if it’s a record day, it’s green. And I call it record book for all these different parts of our product. I look at it every day. I get it’s green. It’s green. We’re rocking it. But, like, I’m not gonna do anything with that. So it’s a waste of time. Think about the time people spend. A lot of times, you don’t have a good telemetry in place. You don’t have good BI systems. So there’s humans spending time counting shit to put the number in, to send out the email with all the numbers so people see it, and is that adding value?

That’s the problem. The human energy waste that goes in to data driven product management when it’s not becoming actionable.

And making sure the thing you’re measuring is not gameable

Exactly. That’s like top of funnel metrics. Yeah. Everything I can make the top of funnel as big as you want.

But but things like active users, time is so precious. If people are spending time in your product, there’s value there. Now, it might be never accretable to revenue value. Right? It measure that’s a business model question. But you’re building something that has value to someone if someone’s using it. So those things are hard to gain.

Wait. Product managers are worse than ever? Yeah. Yeah.

You know, it’s funny. I have a kid, freshman in college, you know, and I just pay attention more of what’s going on in college. And, like, people hire consultancies because it’s a top school of people in college to advise their companies. Companies. It’s It’s like like a a racket, racket, a a name which then employs a bunch of college kids to do the consulting. But there’s the mechanics of product management. Most people don’t have, like, the hunger and the curiosity to keep going and because it’s a it’s a thankless job in a lot of ways.

You think you’re gonna be the rock star, you’re the roadie. You need, like, stick to itiveness, whatever that weird word is, to be in product. But the people that have shown demonstrated impact, you know then that if it was them, and that’s a lot of the interrogation when you’re, you know, hiring people, then they they understand the mechanics of the job. If you were at Google during the aughts, you think it was because of you. So how they accomplish extraordinary things at companies that aren’t ramping.

Yeah. That is

biased. Like, you think you’re like, you ship a feature and it grows. Well, because the button’s on the page and everybody’s there.

I think that on average, yes. Because there’s so many of them. And when companies scale super fast, they have to build big teams fast, and it’s just hard to sustain that.

Absolutely. I mean, I think it’s just a different challenge at every stage, and you’ve talked to Ali a bunch. That’s what keeps him awake at night is the innovation factor. Now, objectively, we seem to be accelerating, which is a little crazy to think about. Like, I use the product constantly. That’s the only way I can understand it. You know? But I can’t keep up with everything now. But, again, we’re, you know, a thousand engineers and more than a 100 people in products. But I think it’s a different game at every stage of the company.

so you know venture, you know startups, product. Why do something? Something? Why do anything? The founder. Why are they doing it? They’re doing it probably because they’re the kind of person that has a problem with authority and can’t have a boss. So great products bend reality. And so you realize something could be made a ton easier. Right? You you’re starting a company, you need to enroll someone in that vision, and you need to bring them along because you want a cofounder. You wanna hire the first engineer or something like that.

You need to get them to believe, or else they’re not gonna go through the shit show to try to get there. I think you will things into existence. I think we do impossible things all the time because we just don’t think they’re impossible. But I think human ingenuity can, like, create impossible things because you just really, really want it to exist, and you find a way.

Yeah.

Yeah. And whether you’re talking to engineers, engineers have to believe.

Yeah. But, again, I call it brain massaging. It’s really manipulation. So you arrived at the conclusion you have to do this through logic. Right? Through a set of assumptions and stuff. And it’s because you’ve basically taken the other possibilities and you’ve disproved them. And so you take the engineer through the same thing. The engineer wants to do this thing, and you’re like, okay. It’s great that you wanna write your own API instead of using a standard. That’s awesome. It would be, like, super efficient. It’ll be great.

So how are we gonna get 10,000 developers to understand that? How are we gonna get the whole ecosystem to adopt it? All the things that you’d have to do if you don’t you know, if you invent some new proprietary shit. And then they’re like, oh, that would suck. And then they realize they don’t wanna do all the work you’d ask them to do to build this whole community. And they’re like, we should use a standard. We should use a standard because then we don’t have to do all that work, and I can work on fun stuff.

But you need to take them down your mental travel because you’re not well, you might be stupid, but you probably have a point of view of why this is the right thing. Mhmm. You need them to discover that in their own framework.

It’s so ingrained in being a human. And it ties to the thing about, like, willing something into existence. I think and this will sound completely bananas to you. I think, like, things you build, things you create that you love and are passionate about, there’s a bit of you in it. There’s a bit of your soul in the thing. And then someone’s telling you to toss it out the window. You gotta be kidding me. And so I think that when you’re gonna change Target and people have been working their ass off to build something meaningful to the old Target, you just have to give it the morning cycle.

You have to be empathetic and human. You need them to come along with you on the ride. So what does that mean? It means that,

Yeah. Because of this world we’re in and these things we need to achieve, this creature you’ve created has an illness. And we have to have a funeral for this thing. But you mourn in a funeral. You give it the space to say, yeah, this really sucks. If you don’t put words to that, if you think they’ll figure that out for themselves, you’re lost, and then you have a churn, like, later on because they’re like, management’s bananas. You know?

Yeah. I mean, that’s great if you’re doing something incremental. If you’re like, let’s grow revenue 10%. Put in a product that knows product market fit. You can have no emotion then. But a lot of the job is not about specking the product and building the product. A lot of the job is about enrolling customers you talk to into what’s possible. How can you do that without emotion? Do you have to do what you love? Oh, that’s funny. No. But you have to love what you do.

So I went to the What’s the difference? Well, I went to the University of Pennsylvania Yeah. Because they told me when I was applying that I could get a dual degree in fine art and engineering. And I got there, and they’re like, who told you that? So I called up my dad. I’m like, dad, I have this deep decision to make. Do I go into fine art or engineering? He was like, it’s not a decision. You go into engineering. So there’s a lot of things I put on pause that I love, but there’s beauty in solving problems for humans.

Yep. And if you’re not inspired by what’s possible in what you’re doing, then you should take a hike.

So, like, it gets back to this data driven thing. Like, I’ve known a lot of product managers that ship a product and don’t observe how it’s behaving in the wild through data. I think they’re fucking insane. You spent all this energy and willpower creating this thing, and you’re not obsessively watching exactly how it interacts with the world? That’s crazy.

Yeah. Oh, okay. I mean, we could like, putting something on your website is not marketing. You gotta get in the mindshare of the person whose problem you’re solving. They’re never gonna look at your website. Yeah. It’s crazy. I’ve never run marketing, so I’m always telling them how they should do their job better. It’s the same thing as the flippers before. Do you worry they don’t like you? Not in a bad way, but like Here’s the thing. Like and this is the core of being a humanist, having empathy.

I think everybody’s a genius, maybe not at their job, but at something. And they’re trying to do the best they can. So if you lead with that kind of empathy and understanding and try to enroll them in why it should be different Do you think

Hold on.

point. There’s a difference between hustle, doing the best you can. Like, okay. I’m having, you know, relationship stress. I didn’t sleep well. I have a migraine. I just wanna get through the day. That might be the best you can. You might be dialing it in at work because of some other meta. People don’t wanna suck, but everybody’s world is infinite. So with that mindset, if you’re if you’re talking to someone in marketing or sales or something and you wanna see different behavior, it’s the same as talking to an engineer.

You need to enroll them in why you the the missing opportunity. And just understand, be inquisitive, and be open as to why don’t we attack it this way? Wouldn’t this be opening up a whole new thing? And when I do that, I learn a lot. And a lot of times, it’s like resource constraints and CEO needs this, all these things, sales. So it’s just like me, people thinking product manager is a god role when it’s a

Well, this is this is where it’s unfair. Because I presume that the only way to interact with the world is to fully understand the functioning system you’re in and then have intellectual rigor and observation of data behind it. So I just assume that that’s how brains work, but not everybody’s brain works that way. So if you assume that that’s just free, then it’s 90% art. But if that’s not a natural inclination of people, then it’s probably a lot more of that being done purposefully.

That’s that I was I was just gonna go there. Like, I have created so many detailed frameworks, and it’s basically like, I have mathematical proof that this is what we should do, but it’s so fallible. There’s something like the fallacy of misplaced concreteness. It’s an economic theory. And the gist of it is the more detail you see, the more correct you think something is. You can have this incredible financial model. Like, you know, people do financial models and spreadsheets all the time. You can have, like, a very simple model or you can have one billions of pages and you’re like, they put so much work into that.

They’re really good. But it’s bullshit. So the key is using your collective experience, and there’s a lot of science and math in that, to find holes in the strategy. Because humans are not mathematically definable, and products are for humans. So overrigor is just waste in the system, I think.

this that’s worked for me thinks I’m totally full of shit now. I ask we ask people to do all tons of shit, and

No. I I always wanna get to the why. Like, let’s talk about people on your team or people, you know, in a close adjacent team. Your team love you despite what you said. I mean Well, I think that’s because of the human connection. I am maddening to work for. I’m maddening because, like I said, I need to understand the system. If there’s something that’s done that I don’t understand, I’m picking it apart and asking a million questions because until I get the system, I might give wrong advice.

But that seems like and oftentimes is a little micromanaging. I’m maddening. I think I connect with people on a human level, so they respect the intent of my maddeningness.

Yeah.

Totally. Every one on one I have is fundamentally different.

with Yeah. But that gets to I mean, you have empathy, EQ, and human understanding in to enable you to do that, and that’s really key in a leader. I think a lot of leaders are formulaic, and I think people follow people that see them. When I’m in a room and I’m frustrated, well, if I feel like I’m not kind of in the core of the conversation, but I have a point of view that I think they need to hear, I just wanna feel seen. If I’m not seen, I feel ignored.

And I think when you give people feedback, you need to get their feedback on your feedback. You might not give them any space to talk about the why or, you know, what they’re going through. That doesn’t mean not to be resolute on the feedback. Like, I need you to do this. And if they, you know, if they look ashen and they, you know, they’re, like, stressed out, figure out why. It’s your job to figure out why. Because otherwise, you’ve lost them. Do you know when you’ve lost them?

I’m overly confident in this topic. So sometimes you do. Sometimes it’s clear. Right? But I I generally have this unspoken or sometimes spoken contract with people that work for me. If you’re gonna leave the company, I’m gonna help you find the best job imaginable. But first, I’m gonna figure out if you’re running away or running towards. Like, if you’re running away from the company because something’s broken, I wanna fix it. If you’re running towards an unimaginable opportunity, I’m gonna guarantee you get it, if I can.

But then, some people don’t trust me. A lot of people tell me six months, nine months before they’re gonna leave, and I helped them get a kick ass job. But some people don’t trust me, tell me, oh, I’ve already accepted this offer from blah blah blah.

I do that with my immediate staff. Yeah. But often, you know, oftentimes there’s layers in an organization and, you know, not everybody knows you that well. Yeah. But I feel because I feel strong connections with people. I feel that they should know me that well. Don’t you know me? Don’t you get that I wouldn’t like walk you out of the building in anger?

And when I come into meetings, in my maddening way, there’s like, you know, the term like seagull management? Like, you swoop in and shit over everything then fly away?

Oh, no. No. You sweep in. It’s like Shit. Someone like categorized a bunch of animals and like so I asked people that know me, like, was I too seagull in that meeting? And sometimes to my directs, it’s fine. But then a new product manager that doesn’t know me is like, why is this SVP giving me shit about all this stuff?

because, I mean, we talked about one of my weaknesses is I’m too optimistic. I think that’s unlocked incredible things in my life, incredible things. But it gets back to if you haven’t enrolled people in the vision, oftentimes, can’t achieve the vision, and then it falls apart. And then they’re like, why were you such an idiot for being so optimistic? I’m like, well, if you believed we would have gotten there, it’s your fault. You know? Don’t say that. But being more selective about the things you care about I would imagine investing in a company, you need to care a little bit.

And so not caring about another BI tool is a blessing. There’s so much optionality in the world that when you reduce dimensions, you get more powerful because you can focus, have more domain context, more point of view, and probably more impact.

There’s so many dimensions of it. But one of the classic failure modes of a startup is they get, like, early signal of product market fit, and then they start talking to customers. And customers, big deal, I’ll, you know, roll this out to all these users if you just do this, but it’s not coherent with, like, the the focus. You know? Suddenly, you’re going large enterprise and SMB. Suddenly, you’re going after the practitioner and the business person. And then you try to be all things to all people.

It’s just way, way, way premature, and then you’re nothing to anyone. Now you could choose a wrong narrow focus and implode. That that’s the balance.

Yeah.

This is a funny what’s that new, like, the diabetes drug that everybody’s losing? Ozempic. Yeah. So I read this article, and someone was concerned that it’ll be the collapse of society. These drugs not only That’s quite a jump. Curb appetite, they curb other addictive things. They’re good for people that have a gambling problem. But then someone looked at the data, and this power users are the the thing that makes the revenue for all companies, basically. Like, there’s people that I don’t know if you have Chipotle here, but say, a fast food that eat it every meal.

I go once a year. The company makes a lot more revenue from these people. And if you take away the addictive tendencies of the super users, no one will make profits in any sector of any business anymore because the eighty twenty rule means you’re gonna lose 80%. Obviously, that’s crazy, but it gets to the Same in gaming, obviously. Yeah. Yeah. Yeah. Yeah. Yeah. So the whole world’s gonna collapse. But you need your fanatic users. If your product becomes everything to everyone, you lose the fanatics. But your fanatics are the ones that talk about it in bars, bring their friends in, have the viral coefficients and stuff, but they’re also the ones that push you to do unimaginable things, to really break through barriers.

It’s hard. Like, you need to use your product every day, and you’re not gonna always be the persona it’s for. But you need to at least have an appreciation for what that persona goes through. Products become complicated over time. You add a feature for one person, it might be another click for another person. But I think that’s where the art is. It gets down to the human connection. Is simple always better in product? Simple is like the dumbest word.

what what the hell does it

always better? No. It’s possible to still give the superpowers to the person you’re giving superpowers, but you can’t dilute their superpowers. Right? So when I came into to Databricks, I started using the product, and I was like, good lord. You know? I’m not I’m not a developer. I mean, I’ve done it. I’m not good at it. Good lord. And I there were all these things that I saw as, you know, broken edges to the product, and I thought it was really important that we fix them.

But most of the things I wanted to focus on didn’t matter at all. Didn’t matter at all. It’s like the speed of execution mattered. Auto completing in code mattered, consistent gutter width on the UI. Nobody gave a shit. But it hurt my eyes to see it because different things matter to the developer wanting to be in the flow of their work than the goofy product manager that joins a company that’s like, this UI is not pretty. So it’s not clear what simple means. Simple doesn’t mean removing optionality unless it does, and that’s where it gets complicated.

Like, you don’t wanna give people five ways to do things. If you can give people one way to do things, that’s great if they can still do the thing that they need to do that they’re using the product for, which oftentimes you know, like, I remember. So I’ve been using Atlassian stuff for a while. In fact, we we we talked to them. I was at this company, Plumtree. Jay Simons, I don’t know if you’ve talked to Yeah. Yeah. Of course. It was a machine last time, actually, about the show.

Oh, yeah? Yeah. Yeah. He’s he’s he’s an old friend. I should have sent you his name, but he has plenty of stories. We tried to acquire Atlassian back in, like, ’98 or something. We thought we should get them cheap. They’re a little dinky company, but they had a plan. You know? And they’re like, pound sand. There’s no way. But we’re like, it’s just in Jira. Then there’s like this Wiki Confluence thing. You know? But then in that product, early on, you could do a lot with, like, markdown and stuff like that.

But they moved a lot of those things to a, like, clickable text editor. And, like, I was furious. I was like, these people are jokers because, like, I wanna do all these things. Now all these things, there’s no button for it, and it’s a lot harder. Now that was the right choice. It radically opened up the TAM. Right? There were a lot less people like me. You know, you need to go into that acknowledging that you’re gonna get rid of some people. Are those people you’re getting rid of key to your vision?

Developers have to love us because they’re gonna be the ones influencing the decision that the CFO makes.

Oh, like, okay. So in short, it’s fractal. I use the product all the time. I’m reviewing the product when I’m using it, like, continuously. And so getting into, like, the preview, we have this dog food system and stuff like that. That’s kind of, like, asynchronous product review. But then, you know, in the classic scrum sprint methodology, you you demo every Friday. You want the core group to be seeing things as it’s being built because you can’t waste time if it’s going the wrong direction you need to know soon.

You should have, like, continuous product reviews for the core team and then monthly or quarterly for management. But the danger the danger is, like, the seagull management. Like, everybody bring them along enough in the

in real time? Like, So, let’s take Databricks. So when I got there, there’s a lot of founders. They’re all ridiculously smart. They’re all operating in the company. And you wanna include them in your early thinking because they have so much context. But then there’s also the danger, you know, if you have a handful of founders, they might not all have the same opinion about the button placement. You know? And so that can be very wasteful to, like, do cycles on exactly how something should look with a lot of people, but the intent and the context they bring to it is super critical.

So the danger is the more people in the room, the worse it is. In a bigger company, people in the management chain all feel like they need to be in the room, and there might be multiple levels there, and then it’s just a ceremony. Like, more than six people? If you’re gonna try to make how many people would you have in the room? Like, it’s gotta be less than 10, probably more than four.

But then if you have 20 people, it’s a ceremony.

Yeah. Because you dilute the clarity and the intensity of what you say, the more people are in the room. Even simple as, like, being glib, using curse words, and things like that.

that that takes maybe four seconds. To say it politely, it takes ten seconds. Yeah. And so you want conversations to be as high bandwidth as possible. Like, if we work together a lot, we have the same lexicon. Right? We can be efficient high bandwidth. If you get 10 people in the room, they’ll oftentimes it’ll be, like, damaging. We’ll understand each other. They’ll interpret it differently, and they’ll report the news to other people

wrong.

and everybody’s terrible I’m terrible at it. I like to be partnered with a program management type person because I’m not fastidious. I want notes to be sent out. And oftentimes, I’ll just like, if I join a meeting and there’s no document link to take notes for the meeting, I go apoplectic. And then I’ll create one, and I’ll write really bad notes, and then I’ll forget to send them out. But I’ll invite other people to, and then they’ll send them out. So, like, I really believe in the importance of that.

I’m kinda shit at it personally, but it’s so important because at any company of any size, any venture of any size, people do stupid shit. Sure. Right? But if we get back to they’re doing the best they can, so why would they do stupid shit? Well, if someone does stupid shit on my team, I didn’t give them the context because they’re smart people. So if they’re doing something dumbass, it’s because I failed to give them the context and the framework to understand why it’s dumbass.

the other thing is, like, I need to understand the system of something before I give advice on it, so I, like, dig in hard. I assume everybody’s brain works like mine, but I have a a foible of thinking people think like me. I assume that things that I find self evident, you find self evident because it’s self evident. But that’s the luxury of me being in a bunch of meetings you’re not in. It’s not clear to me what is in someone else’s brain, and I I misread that a lot.

Yeah.

The first conversation I have with someone, it’s the same as a customer interview or talking to someone in another function and moving to product. So I wanna understand impact you’ve had, and then you’ll say something. And until I think I could do it, I keep asking questions. But you do that until you find someone’s floor. I have an engineering background or at least a civil engineering background, and I can decompose systems. You know? And a lot of product managers don’t know how their shit works. In some consumer companies, that might be okay.

But in enterprise software, gotta know how the shit works. Because otherwise, you’ll make bad decisions because you won’t understand the dependencies. Right? So we talked about how, you know, someone that was at Google during the aughts, whatever they did, the numbers went up. But was it causal is the question. So trying to understand how they dealt with a difficult situation. And then is it other people’s fault? Do they take responsibility? How did they get out of it? Were other people damaged in the way they got out of it?

Is that in

Yeah. I like I I try to connect as a human in the first meeting because first of all, what’s my main goal of the first meeting? I wanna, you know, fast fail if they wouldn’t be a fit, and I want them to wanna talk to us again. Oftentimes, it’s easy to forget the second part. But, like, being deeply, deeply curious about what someone’s done, they feel seen. And if you feel seen, you feel a connection, and you wanna talk again. That’s my hypothesis. Or at least people for whom that doesn’t work, I just lose in the process.

great to find a low stakes way to do work together. The best way to figure out if someone’s good to work with is to work with them. Yeah. But then if you say, give me advice on my product, that’s a big lift for them. And also, don’t have the context. If I was

can say something stupid, and I haven’t given them the context, I judge them for So if we take a problem from their domain, change part of the context, change constraint, and see how they deal with it and talk through it,

with them.

it’s powerful to know nothing because you ask questions that seem dumb, but it can kind of throw people off because they’re not the questions they’re expecting. And you see the internal consistency of what they’re talking about, and again, how they’re talking about it. If they’re just taking credit for shit without the how, it’s really the meta. It could be anything. It could be talking about how civilizations on Mars operate. They don’t exist. But it’s like a great world building fiction book feels real, but it’s all made up.

But there’s a lot of intellectual, you know, coherence in what they’re talking about. So I think you can you can smell bullshit pretty easily, even in a domain you’ve never seen before. If you’re just intellectually curious and you keep digging until you understand it.

Yeah. Exactly. Exactly. It’s a five whys process Yeah. But deal with humans.

So people can be incredible in one company and a total failure in another company. I’ve worked with people who were brilliant game changers. Oftentimes, they didn’t show up first that that was obvious, but then they, like, accomplished amazing things. And then I brought them to interview at another company convinced they’d be a game changer at the other company. And then the panel was like, this person isn’t a fit at all. They give me, you know, a bunch of reasons that are true. And it’s just because different companies have different cultures and different needs.

And, like, let’s say, you know someone would be great. You know they would. But there’s people that doubt in the process. If someone comes in and there’s nonbelievers, confirmation bias is very real. So if you can’t enroll the hiring committee to believe that this person’s great, they’re gonna fail. How do you structure a hiring committee? Not too big. You have to have people whose job it is to prove that the person’s a bad hire. If I have people that work for me as the only people on the hiring committee and they know I really like a person, it’ll color their view.

So you have to have antagonists in the system, a small number. It should be cross functional. You need to have someone technical. Well, in enterprise software, you need to have someone product, someone technical, and some naysayer as, like, the core three, and all three of them have to be deeply, deeply respected in the org. And that’s the hard part. You need their signal to matter.

touch with the day to day of the individual contributor. I don’t know what people spend their time on intrinsically. There’s things I assume I ask for something to be done by everybody in the org. And in my mind, it’s just a tiny, tiny extra effort every week. But these things can pile up and be meaningless to the point where they’re just running the machine, and they’re not doing the art. They’re doing the work, not the arts. Yeah. They’re not deeply truth seeking what really matters for the customer.

They’re filling out How do you retain that at scale? Integrate them into customer support once a month? I mean, you know, measure. I hate the measure what people do, but make sure they’re talking to customers all the time. A third of their time should be talking to customers. A third of their time should be using the product and working with engineering, and a third of their time should be thinking probably. But it never works out that way because usually 60%

Why? Because they’re an opposite let’s say, like, when I came into to Databricks, it was bimodal. Engineers thought sales ran the company and were destroying it, and sales thought engineering ran the company and were destroying it. There was no real product muscle. Ali ran product, but then he became CEO, there was a gap. Right? Engineers and sales have I’m say it’s a good word. Motivations. Short term, long term. They’re always gonna think the company would be better if the other had less influence. A salesperson, like, is a customer that wants to give me $5,000,000.

Are you on crack? Why aren’t we building this feature to get the $5,000,000? Engineers like, it it would destroy the company because

I’m like the I’m like the fixer or the mediator for a lot of these things. So, like, I always try to find a third way. People always present options that are myopic. You know? We don’t do this and we lose the revenue, or we do it and it delays our strategy. I’m like, no. I don’t like either of those options. So you talk to the customer and you find out they don’t even need the feature. It happens all the time. You’re like, we could do this for you.

We could do this for you. But wouldn’t it be better if we did this for you? And no. No. I really need this. But then you just tease it out. I’m like, but if we did this, this whole scope of work you have to do first half of next year would disappear. So, again, you talk to the customer, you diffuse the situation, you enroll them into what you really wanna do, and then you make the salesperson realize you never needed the feature. Now, you know, it doesn’t always happen.

And because I’m too optimistic, sometimes I, like, come up with a crazy third way. It’s possible if everybody was inside my brain, but then coordinating all the pieces to do weird shit

think that every great leader in startups, you’re you’re bending reality. You’re creating things that seem impossible. You have to enroll people in that, and once they’re enrolled if you think something’s impossible, but you convince three friends, then the four of you think something’s impossible, but the world, reality, thinks it’s impossible. That’s reality distortion. But you enroll people in it so they can hunker down and prove everybody wrong and accomplish it. As organizations grow and leaders have ego, you can believe yourself and not be truth seeking.

And then you can do your company a lot of damage and you can do people a lot. Think about how many people that have been traumatized by startups. It was kind of like, we wanna accomplish this by any means necessary because it’s the right thing to do, and you start to see less and less what you’re compromising to do that. If you get caught up in your own reality distortion field, it might be impossible. So you’ve convinced all these people that something impossible is possible, and they’re gonna waste a lot of their career chasing you on it because you’re so convincing.

That’s when it gets a dark side.

Like, after every product role I do, when I’m seeking my next role, I want to be anything but product. And then you meet someone like, you know, Ali pulls back this curtain and you’re like, holy shit. I wanna be part of this. Let me do some products. The CEO is the CPO. So it gets back to, are you a rock star or are you a roadie? You’re a roadie. It gets complicated because you want to exercise your craft and do something that you know is the right thing to do.

The CEO is driving the vision of the company and knows the right thing to do. And you can’t be in their brain, and they can’t be in your brain, and you’re both working really hard and really busy and probably don’t talk that much. So there’s always this conflict between you’re hearing that we need to do things that you don’t understand the full context of, and it’s frictive with what you know you need to do. But you don’t have the bandwidth or the time to articulate what’s in your brain to the CEO.

How do you have great communication then? Again, it gets back to hiring, but high bandwidth and truth seeking, taking ego out of it. I’ve had a lot of difficult bosses. Speak to Ali? Very seldom. But it’s generally messaging and calls late at night because the key is to be simpatico enough. Like, for example, for the second half of the year, I listed all the main objectives I had and the tide of the vision and what outcomes they drive. I get his buy in on that, and I just relentlessly go after those.

I oftentimes I send a lot to him responses on unless he disagrees. There’s a lot of delicate shit that goes on. I send to him, probably, you know, a couple other leaders, founders, Adam or whoever. And then if I hear nothing,

Because I form this human connection with people, I underestimate the negative impact my words can have.

Yeah. I might be despondent about something unrelated to the topic at hand. My body language conveys that, and that’s interpreted as disappointment in the topic at hand. How would you change that? Move on. Being cognizant of it minimizes it and takes the edge off it, but it’s just, you know, moving fast, trying Or

I think that gets to, like you talked about how everyone on one is different. Right? Yep. Just be direct and honest. Be vulnerable and share what’s going on, and then they’ll assume best intent with how you communicate.

funny. We both know Jay Simons well. Right?

And he just talked about, like, there’s this stage you get when an elevator ride is, like, heightened and consequential for how you interact with everybody in the elevator because of your role. And people want things from you. People wanna feel seen by you. It gets crazy. The way you can work is hard. Yeah. And you can have a very brief interaction that’s very asymmetric in how much

that’s that’s hard.

hard. And that’s why sometimes it’s like so we’re doing this conference. You know? So I gave a couple keynotes yesterday, customer meetings for five hours, and then I go to dinner with, like, 50 customers. Are you kidding me? It’s so loud. You can’t hear people. Bizarre accents. You have to really focus. You’re just done. You just need quiet time.

the customer and really, really know exactly how the product works and know exactly what the customers need in aggregate.

founders make when hiring product teams? Not being clear about the level of agency they’ll have. A founder CEO is gonna be in the details of all the shit, and that’s good. And some people expect complete agency calling the shots as a product leader, and they

the I was talking about good founders. Yeah. I’ve worked with a lot of people that were basically, like, the right thing for me to say was I’ve got it. And I tried that for the first six months of Databricks, and that’s not what Ali wanted to hear. He didn’t want me to go off and do something and then show him how awesome it was. You know, he wanted to be deeply involved and have the founders deeply involved in the sausage making because they had so much more context, and I wouldn’t go through,

There’s a failure mode where you feel like you have to put together comprehensive frameworks that sales is, you know, given confidence by, and just give yourself time. Do as little changing the world of how the company works as possible in the first ninety days. Should you look for early easy wins? Yeah. But they shouldn’t be vanity wins. You know? If the early wins are human more than technical, you’ll build the followership you need. What are some most important skills to build

So when I was at Plumtree and Phil Sofer left and told John Kunst to make me run product, I met with John Kunst. And he he was at Adobe in the great days. You know? And I was like, John, I’ll do this. I’ll do this if you want me to do this, but I need you to be my mentor. I need you to teach me how to do products. I I don’t know what to do. And he’s like, he can’t teach it.

Just, like, hold on to the wonder. What does that mean? The first kid we had, it’s like urgency for them to, like, roll over. They’re gonna walk. When are they gonna walk? When are they gonna like, second kid, you wanna delay walking as much as possible because then you have to chase them. You know? Just watching them. You watch videos of them as babies now, and you’re just like, it’s just amazing. Every little thing they do is amazing. Stop trying to shape them. Just get a front row seat.

Does it get easier? My wife says bigger kids, bigger problems. You know? So it gets different. It’s interesting. It ties into career. Right? Because these things are balanced. I used to think when I left work to go home, I was being selfish until I had kids. And then I thought, when I stay at work and don’t go home, I’m being selfish. I think the clarity is easiest when they’re young because spending time is good and and what to do. How to navigate as they get older?

How much do you try to try to direct shape? I’m bad. I’m a bad disciplinarian. You know? In sales and engineering, I try to find the third way. The kid is obstinate. You know, the rules are this. I try to find a compromise. Compromise isn’t always good for kids. You know? You need to set boundaries. I don’t know. Isn’t that why you have

You gotta balance it.

Why didn’t that happen twenty years earlier, though? That’s what I can’t figure out. It seems so self evident. When you asked the question, I was thinking more about business model because I think that’s where disintermediating things and there’s a there’s a

In

house. Yeah. Not on the craft of the product. I really respect the craft of the product. The companies that I find most intriguing are ones that have a very unusual insight in the business model. Like, the early days of a company like Opower. They were using data to drive efficiency at power plants in The US because the power plants got paid by the government for reducing the demand of the energy. You know? So it’s like multiple way it’s very complicated to pull things off like that.

Like, figuring out to to the big problems of environmental transformation, energy efficiency, social and economic equity, you have to come up with really creative business models to tackle those things. And I think those those are the fun ones to think about.