When to Hire a CPO, The Three Different Types of CPO

One of the patterns is the three types of product leaders, and they are the operator, the craftsperson and the visionary. What is really important is there is no one right answer first of all. It really depends. But the second thing is that it’s important to recognize that it’s not like a certain person can only be an operator. They can wear each of these hats. So you can think about them as hats. But still people have a primary hat and that’s the hat that makes them most comfortable, that’s the hat they would rather wear.

But the operator is excellent at scaling teams, driving cross org alignment and unblocking execution. And the operator superpower is communication. On the other hand, one of their challenges is actually original product insight. So this is very important to remember. There are oftentimes there are operators who just like have amazing resumes. They’ve scaled companies and products extremely well whether it’s larger companies or mid sized companies. But despite all that experience, they do not have the ability to come up with really original product insights. This is where often things go wrong with CPO hiring or VP product hiring.

Sometimes your situation is such that you do not yet need an operator. Eventually, almost everybody starts needing an operator in their head of product role, but you don’t yet need one, but you bring somebody on with the expectation that like, business is gonna quadruple at some point, so at some point we’re gonna need somebody like this, so why not bring them early? But the problem is now this operator starts operating instead of helping you get to a better position with your product market fit. That requires original product insight.

And without much help, the operator is not going to be able to do it on their own. So that’s just an example of where, like, things go wrong.

It is nearly impossible for an operator to bring your product to Product Market Fit. But once you hit Product Market Fit and as your product starts scaling, as the cross organization complexity increases. Now what happens is in addition to managing the product, you also have a real big organization to manage. Oftentimes it’s cross team, right, like you’re not owning everything and that’s where operators are tremendously valuable because they are extremely skilled at orchestrating cross organizational action. They’re extremely skilled at communication to make sure that everybody is aligned.

They’re fairly skilled at setting targets, setting goals and creating a sort of a rhythm in terms of how you launch things in this complex internal environment. So really that is the point, but at some point it becomes very clear that you need an operator and then you need to go find one.

Walk me through that one. So the craftsperson is excellent at defining products and strategy and mentoring other product people. And their superpower is product insight. The craftsperson is able to translate an extremely ambiguous goal or an extremely ambiguous vision into concrete product that has a very high chance of winning. That skill of translating something high level and ambiguous to actual product the pixels, the customer support experience, the interplay of the various things that need to happen to make a product and a business successful they are able to translate that really well.

Again, their superpower is product insight, but they’re not excellent at dealing with large orgs and its taxes. Right? Because any large org comes with all sorts of taxes that you have to deal with. They just don’t enjoy that. They love spending time with the team and users. It’s interesting operators, they love spending time with their peers, other functional heads, and company execs, and the board. Whereas, as craftspeople absolutely love spending time with users and customers and the team, and they get really excited about product deep dives, and, oh, let’s walk through this flow and how can we make it better.

So that’s the craftsperson. It’s a very essential ingredient in any team. Whether it’s a product leader or even individual product managers, you need these people so that you can translate something ambiguous into something concrete.

That is a reasonable default, especially if you’re early stage, say perhaps pre PMF or just about reaching PMF, then craftsperson is of good default. When I go through these kind of sessions with founders one of the core things I ask them is like why do you want to hire a product manager? What is it that you want this person to do that you are doing right now? Sometimes, Harry, the answer is I want to delegate a lot of the operational work. I want to delegate figuring out how the sprints are going to work or figuring out how customer support is going to get impacted by this new product feature that we are launching.

Those types of things I want to delegate, but I still feel like I need to own the core product insights and some of the definition of the product. In those cases, you may want to bring a sort of like a mid level or a junior operator type person and kind of delegate those operations while still holding on to the visionary and craftsperson hat yourself as a founder. So that is possible, but the default craftsperson is a good place to start.

There are two core things that tend to break across most situations. One is within the team. As a team grows, a large part of your role as a leader, you’re basically a repeater. You just have to keep repeating the same thing. If you’re managing a team of 25 people, you can have a sort of personal relationship, some amount of trust, some amount of like just mind meld with a group that say 20 or 25. Now your team is 50 people. It’s impossible to create that mind meld.

So you need to change your approach. Now, instead of relying on one to one or one to few interactions, you have to rely on one to many interactions. But people don’t remember as much as we think they remember. So you have to keep repeating the vision, the goals, the strategy. That becomes a really important part of your role. A craftsperson can do this but as the team scales, a craftsperson most craftspeople don’t enjoy that. So that’s one thing that kind of starts breaking internally for a craftsperson.

Externally, so outside of the org, what ends up happening is as the business scales, there are other parts of the business, other departments like sales and support and BD and marketing and various other parts of the organization begin relying on you. And you begin relying more on them as well. You’re no longer kind of self sufficient and scrappy and there are a lot of alignment issues, are a lot of dependencies that you need to resolve. When you reach a certain scale that becomes an extremely large part of a product leader’s role.

So that’s the part that starts breaking outside of the team. What is the profile of a visionary? Among these profiles, the visionary is the most rare. The visionary is excellent at big picture thinking, inventing what’s next and their superpower being that they can see what others cannot see. One of the challenges with a visionary is that a visionary finds it difficult to translate that big vision which by the way, again, by definition, very few people can see that vision. Even many craftspeople cannot see that big vision.

A visionary finds it hard to translate that to concrete product steps. Like, okay, so I want to do this. I want to revolutionize, I don’t know, spreadsheets And I have a certain vision in my head of how that is supposed to happen, but what is the first step I take? What is the next step I take? And what’s the step after that? That is where a visionary works very well with a craftsperson because a craftsperson can translate that into concrete steps. And again, there are many visionaries who are also craftspeople.

And I’ve worked with many such folks. So they can do that job, but only to a point. These really great visionaries, they often find it hard, not always, but they often find it hard without the support of craftspeople and operators to do it consistently. Should the founder not be the visionary and the CPO not be the craftsperson? It’s usually one of the founders that’s the visionary. Perhaps, you know, there’s another founder that’s more like an operator and maybe even a third that’s more like a craftsperson.

But typically, there’s one founder who’s the core visionary who then takes ownership of the product and sometimes wears the craftsperson hat. And like I said, they can be fairly good at it to kind of translate that vision into certain kind of product manifestations, but at some point it becomes harder for them. Like, because once you start getting users and once you start getting usage, what ends up happening is users are pulling you in many different The visionary has a very clear view of the future, but being responsible people, they also now take into account user and customer feedback and that can get confusing at times.

Even if it’s not confusing for them, they may find it hard to kind of like bring the team along on like, okay, given all this kind of conflicting feedback and this plethora of ways in which we can take the product, here’s what we’re going to do as step one, step two, step three. Here’s how we’re going to actually build out the product. These are the flows that matter. These are the flows that don’t matter. That’s when, whether it’s a CPO or a VP product or even a Director of Product or an individual product manager, craftsperson becomes a great asset for visionary.

The journey around when to bring in a product leader really, really corresponds to where a company is in their growth trajectory. Pre product market sit, founder’s usually doing most of the product management, working with directly with the engineers, getting things built. Then usually, you know, you find product market fit, and and maybe you bring on your first product manager or your first, you know, sort of quote unquote product leader. And really, the job is to continue to execute on the founder’s vision. And so you gotta be really clear that that’s the job.

The founder typically is the one who’s really driving and your job is really to execute. And then when you sort of hit this like level of scale of things are working well, we’re humming, then your job as the product leader becomes not just executing the founder’s vision, but how do I create predictability? How do I create repeatability? How do I start to hire team and start to make this machine move faster to continue to essentially execute? And then I think you hit another phase, which I’ll just call kind of hyper growth or late stage where you have a product and it’s humming, now and it’s time to open up new growth levers.

So you’re talking about new products. You’re talking about new geographies. You’re talking about new channels. And that’s where you typically see someone bringing in a CPO, someone who’s seen the movie play out before, hired great product teams, you know, able to work in a really complex environment. That’s typically how you see the kind of trajectory.

Absolutely not. And the best product companies out there find a way not to. An important part of that formula is, one, what’s the role of the founder? Founder? And this is where I think the relationship between the CPO and the CEO or the founder CEO becomes really critical at this stage that you’re talking about. The mistakes that I see happen is that the CEO founder goes to hire for a skill set that is either at odds with what they really need, or they’re not actually honest with themselves around the role that they want to continue to play within product.

And so if you’re if you’re a strong visionary founder CEO, really, you just need an operator and an executor, but you go hire someone who’s drawn that vision, well, then you’re just gonna clash. Or opposite, right, you really need someone who’s gonna bring that vision. The founder or CEO has moved into a a much different role, but you go hire what you just described as sort of the operator, well, yeah, you’re gonna start to lose that product culture and that that vision and that craft.

So I think it really actually comes down to understanding the dynamics between the sort of what is typically a founder CEO and the CPO, and who has what strengths, how do those complement each other, and making sure there’s incredible clarity around who’s gonna be doing what as it relates to product.

I think the most important part is starting first with what do you describe as the competencies with which you evaluate product managers or what you need out of product managers or your company. So I think most importantly, before you even start bringing anyone in through the door, is getting onto a piece of paper. What are the core competencies that we believe are required out of every product manager here or very specifically the role hiring for, and how are we gonna test each of those competencies. And so once you sort of have at least a general framework for what you’re looking for for candidates, then it typically goes through sort of a three part process.

The first is usually the hiring manager phone screen. This is typically where you wanna really understand more deeply their background and their experience and their skill set, and maybe even most importantly, their interest in the role. And if you can get ahead of wasting time across the whole interview process just to find out that really this person’s interests don’t really align with the role, so hiring manager funds screen first. Assuming that goes well and the hiring manager feels confident that their experience and their skill sets are relevant, then you typically will move on to the panel interview.

And the panel interview will really be taking those core competencies, assigning them to each of the individuals on the panel, and having a very clear and repeatable way with which you’re teasing out whether someone has that sort of competency or not. The biggest mistakes that folks make on the hiring panel is there’s not a lot of order and structure. And so you’ve got, you know, one person goes in and asks one question, and the other person goes in and asks another question. Questions are actually, like, pretty similar, and so you don’t actually tease out anything new from each of the different steps of the panel.

For me, I’d look at really kind of four main components of what I would expect out of a product manager. So the first is really all about synthesizing large amounts of information and data points and being able to use that to prioritize the right problems to solve. You might call that strategy. The second bucket is, can you then use your curiosity, your creativity, your intuition to tell a compelling story around what a winning product solution might look like to that prioritized problem. And that’s where we sort of talk about product sense.

The third for me is, can you then inspire and influence your team to deliver this winning solution that you’ve sort of come up with? And that sort of the bucket there is leadership and communication and and execution. And then lastly, can you sort of set up the right success metrics to ensure that you know whether you’ve actually made the impact for the business that you were expecting to? And if you didn’t, are you sort of adaptable to testing and learning and iterating until you get it right?

So I think those sort of strategy and product sense, leadership, communication, execution, and analytical thinking tend to be sort of the different buckets that most product organizations are looking for in product managers.

Well, if you’re early stage, your product team maybe is one person. Right? Maybe you’re hiring one PM. This is another meta mistake as people think like, I’ve raised my seed round. I have $4,000,000. Like, let’s go hire a team of 20 people. That’s what I see all my cohort members doing. That’s probably the wrong thing to do unless you really have product market fit already. But let’s assume things are on fire, like, oh my god, we’ve gotta build all these things. Like, great news. I would say at the early stage, the number one thing I would filter for and find some products that you think are good and some products that you think are bad, ask them about them.

See if they’ve ever gotten to the point of thinking about why a product they love is great versus why a product that they don’t love is bad. And can they explain it to you? Do they have an opinion on it? These are things that are very squishy. It’s very hard to like, how how would you, like, write a multiple choice test that would test that? It’s very difficult. But these are the things you’re looking for because they show that the person has, thought from first principles about why a thing that they see is true in the world is true.

And the why is what matters. And the skill of asking why and learning why or figuring out why is the number one skill for building early stage companies. Because that’s what you’re doing all day long. Why is this working? Why is this not working? How do we do more of the thing that is working?

Again, most people do this probably too early. So that’s, like, the common theme here. So I made this mistake myself. At Bump, we got to, like, maybe it was 30 employees. All of our vanity metric graphs were, like, going way up. We were feeling really good. And I thought our company is gonna need to, like, figure out our business model eventually. We’re gonna need to keep scaling and hiring. I’m gonna have to do more fundraising. I better hire a product lead to take over from me, and I’ll go focus on those other things.

And I did. He was awesome. And then we realized, oh, actually, we have not really solved product market fit. Sure, we have a lot of people who use our product, but, like, we can’t figure out a way for them to pay us. We can’t figure out anybody else in the world who will pay us for access to those users in some way. So really, we don’t have product market fit. Whoops. And I realized the success or failure of my company actually has to do with what this person I just hired is gonna go figure out for me.

Generally, that is a very dangerous place to be where the founders or the CEO of the company is not working on the most important problem for the company’s success. I just found at some point that I need to be doing that. It’s my responsibility for this company to be successful. I better be working on this. And now all of a sudden we have two people who wanna be top person on product. Dave made a mistake. You know, I was wrong about when to hire this thing, and we parted ways, and that was the right call for the company.

other piece of it is people wanna hire people like them. When you’re hiring the top product lead for your team, if you plan to be around for a long time, you probably don’t wanna hire someone exactly like you with the same set of skills. As an example, on Google Photos, when we grew enough to where I needed to hire someone to run the product team, I very explicitly wanted someone who had a complimentary set of skills. What are the things that I’m uniquely bad at? Let’s find someone who’s world class at all of those things, and they will, like, really plug a big gap in our team.

That’s the way you should do these things.

Yeah. 100% agree. I would say, like, the number one failure mode when people hire product leaders is they over index on previous scale, how big of a team have you previously managed, or tenure. Like, how long have you been doing this? What experience do you have? Do you have experience in our domain? It turns out that if you’re the median PM in the world, you’re, like, middle of the not good, not bad, you’re just median, if you stay in the game long enough, you will be that person.

By definition, almost. Right? If you last long enough, you will eventually lead a team of 25 PMs. But you’re not actually good necessarily. You’re medium. And it’s very dangerous to hire those people. You’ve heard this saying before, but like, a players hire a players and b players hire c players. It’s totally true. It happens, like, literally all the time. I watch it happen. Once you hire that b player to be your lead, like, bye bye. Your team is gone. Like the best people on your team are not gonna wanna work with that person.

So how do you avoid it? I think you gotta retain this ability to be either a craftsman or a visionary, hopefully both, because those are the people that people wanna follow. They wanna listen to what they’re saying. They wanna work with the people who wanna work with that person. I think it’s incredibly valuable. Yet, founders think, I better hire this experienced person who knows how to do this. But turns out they don’t actually know how to do it.

Yeah. Is there a time for work? Yes. But there still must be a product visionary and a craftsperson. You gotta have somebody on the team who’s doing that role. It’s totally fine if that person is the founder CEO or the co founder who’s focusing on product. And if you’re hiring an operator to like run your team, which those people are incredibly valuable, you can’t really operate at scale without somebody who’s good at that. But you should not confuse that with who is the visionary, who’s the person, you know, leading the charge on what we’re gonna build next, who’s the person that reinforces the culture that we want at the company day to day.

That person must exist. It’s fine if it’s not the chief product officer. It just needs to be somebody.

In my experience, most of the really strong PMs that have emerged, say, on the Google Photos team came from backgrounds with no experience in this domain. I probably go so far as to say that it’s anti correlated with the top performers. The top performers tend to come from some strange background. I think one of the folks you talked to on our team joined Google as like a salesperson, and now they’re a PM running like a big chunk of Google Photos. And again, I think it gets down to this like self selection for ambition, like a chip on your shoulder.

These people wanna prove that they can do this or they can win. And those people tend to work harder. They tend to like understand the customer more. They go the extra mile, and these are the things that separate success from losing. I’m so enjoying this. What’s the difference between good and great in those PMs? I guess it comes down to two things. The ability to really understand the user very deeply, and then the ability to craft creative solutions to those problems that you find. Those, I think, are the two core parts of the job of being a PM.

I’m a big believer in the founder as the product leader. I personally never invest in a startup unless at least one of the founders is a proven product leader. Now, of course, the equation, the calculus is a little different if neither or none of the founders are a product leader. First of all, I don’t have a lot of confidence in that company. But second, you’re gonna have to bring products expertise on much, much sooner. But if we can assume in this discussion we have at least one founder that’s a proven product leader, then it actually becomes quite clear.

And honestly, it’s a function of the number of engineers more than anything. That’s the heuristic I use. And that’s because at a certain point, there is no way for that founder to be close enough to all of the engineers to be able to make the daily decisions on the product that founder needs to make. Partly this depends on just how many hours is this founder willing to invest in this stuff. But realistically, once you get past about 25, 30 engineers, the teams are saying, I can’t get enough time with the founder.

I just can’t get enough time. We’re going too slow. We’re waiting. We’re making bad choices or no choices, which is worse. That seems like an awful lot of

Realize it’s not like 25 flat engineers where all are considered equal. What they are, they’re naturally gonna group around product teams. If you have 25 engineers, you’ve probably got a minimum of three, probably four, five product teams. Each one of those will have a very senior engineer. It’s those people that have to have that very close relationship with the founder. That tech lead, of course, is talking in detail with all the other engineers about how they’re gonna divide and conquer on the work. How do I structure the hiring process for them?

most important, actually. Let’s talk about what you really need. What kind of person are you looking for? Is it literally just your capacity is out, or maybe you’re much more the visionary and you need somebody that knows how to make this machine work a lot faster. These are some pretty different responsibilities that you’re talking about. We wanna be very clear on the kind of product person that you’re really looking for, and then we can get to work. Yes. For sure. Most companies, in my opinion, don’t do a very good job on the whole hiring process.

They’re just very random. Another big thing we need to talk about is what is your philosophy on this? Would you rather hire, say, university graduates and develop them into the kind of people you need? Or do you say, no. I want people that are been there, done that, and I’m willing to pay a lot more, but I’m paying for that experience. Both of those can work. What’s great about startups, the biggest reason somebody great would join your company is because of your product vision. You are trying to do something that inspires them.

Look at all the people that go work for Tesla or SpaceX despite crazy everything because they are so passionate about what those companies are trying to do. This is our number one tool for attracting strong product people, is having a very inspiring and compelling vision. Here’s the thing though on hiring that’s most important. If you decide for whatever reason you’re gonna hire junior people, then the worst thing you can do is do that and not have somebody in place to develop them. If you just hire junior people and they have no coaching on an ongoing basis, you’re just throwing good money after bad.

That’s exactly what happens in so many companies. So the prerequisite for hiring junior people and I wanna be clear, I love this model. And this is the most scalable model I know. Look at Google. Look at Apple. They do a ton of this, but they have too. The mechanism in place, their managers know their number one responsibility is to coach and develop these people. Let’s run with this though.

If you’re hiring experienced people, that’s one interview. If you’re hiring, by definition, inexperienced people, that’s a very different one. You’re looking and obviously, when you’re looking for experience, you’re looking for whether they can prove to you they’ve learned about the business, they’ve learned about customers, they understand the techniques. To me, that is much more straightforward. When you were hiring on potential, then you’re making a bet on really more innate traits. And then you’re looking for things like, is this person got a strong work ethic? Does this person have a strong sense of curiosity?

Is this person that gives up very easily when they run into roadblocks? There’s a lot of ways to test. I’m not a fan, by the way, of tests in terms of people who will have these assignments. Why

In my experience, they’re not very indicative of what you’re really looking for. And let me put it this way, I still haven’t found that test that I think is any good. It is true though that the risk for an inexperienced hire is higher. I always tell the first of all, I tell the founder, please don’t do that unless you have a like a director in place who knows it’s their job to coach and develop those people. Don’t do it. Otherwise, you’re just setting them up to fail.

But if you’ve got that person, then I tell them that they basically have three months to get those people to competence. That’s what it usually takes, is about three months to get them to competence.

He’s absolutely right. There has always been a debate in the product world. Do you hire people from the domain, or do you hire product people based on product potential and expect that they can learn pretty much any domain? I am squarely on the side that I think he is. My evidence for that is just look across our industry, across time, that all the innovative products, almost all of them came from people and teams that had no real domain experience. You probably know Shreyas Doshi. The way he phrased this, I give him credit.

I love it. I’ve shared it with lots of people. But one of the things that’s critical about product is to be able to understand the difference between domain expertise and domain dogma. And it is very hard when you grow up in a domain to be able to know the difference. You’re too close that way. That’s my theory that explains why is it that so often the innovations come from people outside of that domain. I’m a big fan of hiring for product people and I expect them to be able to learn the domain that’s part of the three months.

I know some people that came from the domain that are rock stars. It’s just that for the most part, I would rather have somebody with good product skills that I know can learn what they need too quickly.

When is the right time to hire a product manager? My first piece of advice always is you should wait longer than you think you need to. Founders often have this dream. They’re gonna find this amazing person. They’re gonna agree with them on everything. They’re gonna know how to build incredible product, and they could just kind of, like, delegate this. But it turns out that’s rarely the case. Usually, what actually happens, you find this person. You as a founder, you still have really strong opinions about what to build, and you’ve been doing them for a long time.

And then there’s, like, the team building it, and so this PM just becomes this middle layer between you telling them, hey. I really think we should build this, and they’re like, do I have any autonomy? Do I have any way that I can actually inform what we’re building? You’re just telling me what to build, and they’re just, like, telling engineers what to build, and it becomes a really hard job for a lot of PMs. A lot of times, the founder has a bad time with that too.

So just like default advice is wait longer than you think. But the three things that have founders have told me are kind of signs that they need to hire a PM. One is they’re experiencing a bunch of bottlenecks, frequent bottlenecks, where engineers or designers are just, like, blocked waiting for them to make a decision, waiting for them to make to review a design. So if you’re finding there’s just, like, your team is blocked and you need somebody to unblock them, that’s a sign you may need APM.

Another is just frequent misalignment. Timelines are not on people like design engineer, for example, are not aware of, oh, we’re trying to hit this date, or they’re misaligned on priorities, or they’re misaligned on the strategy, where people are just not in sync, and that’s what PMs are really good at. And so that’s a time when a PM could come in and help you. A third bucket is really interesting, and this happened at a few companies, and that’s where you have an opportunity to explore a new idea and a new direction, kind of like a new little side opportunity.

As a founder, you just don’t have time, and you wanna find kind of a mini CEO to take that on. So as an example, Zimride, to explore the idea of Lyft, hired their first PM, and his job was go exploring this idea of Lyft for us. Snap and Twitter, from what I understand, both hired their first PM to explore monetization on the platform. So that was their first PM. I love that as a startup

Yeah. Totally. So There’s a lot of ways to do it. Unclear exactly what the best way to do it, but the way I I like to approach it and it works is you basically bring a candidate in for a whole day, try to break up the interview process to a project at the beginning of the day, and then a bunch of one on one interviews the second half of the day. And before I get into those two, just like broadly, the things you wanna be looking for in a PM.

There’s kind of these five key skills. Focus on their execution skills, their collaboration skills, their just broad leadership skills, their vision plus strategy, and then their ability to do customer re user research and extract customer insights. Five things to focus on. Okay. So they come in. The first thing I like to do is do a little project. And the way I like to approach it is I sit them down and I give them a prompt. I print it out. Here’s like a problem that you as a PMR needs to solve.

It could be like, how do we increase adoption of this feature by 50%? Or how do we grow supply in our marketplace by a thousand percent? That kind of thing. And then you give them some context so they have all the information. Then you give them ninety minutes to sit there and just think about it and put together a presentation or a doc with how they’d approach it. And then they present it to a group of cross functional team members, and then there’s some Q and A and things like that.

And the thing you look for there is not they have the best answer have and they come up with the best solution, but how do they break it down? How do they approach the problem? How do they zero in on where opportunity could be? And then just like their gut instincts, what might work. Personally, I hate putting people on the spot with a really hard task because as a PM, you don’t need to be like on the spot solving really hard problems. You have time to think and process and research.

That’s why I like the old time to think about this thing, not just, like, cool design a solution on the whiteboard now. Go.

So as someone who has actually literally given this advice to someone as of two weeks ago, I’m going to cheat a bit and share what I said to this founder. Right. I said two things. One, the biggest risk here is an act of commission, not omission. What I said was you’re going to make a bigger mistake and like it’s a bigger negative impact on the company if you hire the wrong person versus hire the right person. So it’s a high leverage hire. Unless you absolutely, absolutely need it.

At the earlier stage, you are the founder. You are the one solving problems for people. So if you outsource that job, that’s a big risk for you. Right? You need to live and breathe that problem enough that at some point if it becomes obvious that there’s another person or there’s a coprocessor that’ll help and like there’s arms and legs that are needed here, yes. But until then, don’t do it because you can’t think of the problem for people because that is a symptom of a bigger problem there, right?

And you can’t solve it by hiring a product manager. I think the second is I would say one of the questions people ask and the sponsor ask to you is like, folks say about pre product market fit, what’s the role of a product manager? It is actually something similar to what we just described. I think a really effective like hands on, some stage product manager can be the boots on the ground, like, actually talk to customers, actually do a whole bunch of research and connect the dots from, like, what the problems translate that to what is the minimum viable product that is being built.

And so you need somebody who’s just like deeply invested in the problem space. Do not hire a general athlete problem PM is my advice.

I think across the board, there’s one invariant, which is you have to decide upfront what stage are you hiring for. Right? So in this case, if you’re saying like it’s an early stage product, the most important factor I would look for is just like the hustle and drive at that stage. At a later stage and for a different product, the domain experience may matter a lot more. But my bias or my preference is really higher for the hustle and extremely strong high tolerance for ambiguity and uncertainty.

Because, like, if they get queasy on the roller coaster ride, they’re not the right people.

So there’s two things. One is it’s what they did versus what they’re saying because some folks interview very well. That doesn’t often always translate. In fact, actually, like, I think studies have over and over proven for things that are kind of like there’s a lot of practitioner judgment and decision making discipline involved. The interviewing correlation is only weak. So I would look a lot at kind of the back channel on this person. For example, there are different phases for big companies. Sometimes, like, there’s all these amazing tailwinds that help companies grow.

You know, if you were working on News Feed and Facebook or Search, of course, the web grew with it. Mobile grew with it. So you have to differentiate between people who were in the parade versus help the parade. And you certainly have to look for the jerks who pushed everybody aside and somehow got to the front of the parade.

One pushback I oftentimes give to founders is that they should be hiring a product leader so soon. Because as founders and therefore CEOs oftentimes, you think that you should abstract yourself out of every function in order to scale. That’s almost true. You know, I think you should abstract yourself out of almost every function except for the one that is your superpower that you are the unique person in the world to do. And you should keep doing that as long as humanly possible. Is Mark Zuckerberg still the head of product at Facebook?

Is, you know, a lot of these people are still the heads of product of their own companies despite the scale, scale, and it’s probably because that is their superpower. They didn’t want to fully hand the reins over on something that ultimately differentiated them creating this company over somebody else. So step number one is challenge yourself. Should you really be hiring another product visionary if that’s you? Or should you hire some people that are more towards the execution side? Help you scale on the accountability as opposed to the vision.

Number one. I I think the second thing is, you there are different types of product leaders for different stages of a product. You know, some are are very comfortable being very design driven, setting a product strategy, a vision, rallying the troops around this, ensuring that the experience is exactly what it needs to be. Whereas others are more of the data driven program manager types who come in, you know, it’s always about here’s what we’re seeing. We just need to iterate and iterate and iterate this product to make it better and better and better.

Those are two different skill sets to some degree and very few people have them both in equal measure. So you have to also think about the type of product leaders you need right now. And then it’s about going out and, you know, finding the people that are in the, you know, in the weeds and the products you admire. In terms of actually hiring those product leaders, first of all, I would ask about projects they’re really proud of, which gives gives you a sense of what their values are for measuring the quality of both the product and a product team.

I would look at their product quite a bit. I feel like a product always speaks to the DNA of the team behind it. You can tell who wasn’t talking to one another, you know, what the values were, whether there was a designer outsourced or in the room sufficiently empowered, etcetera. And, you know, based on what I see, I would actually ask some questions, like, how did the product end up this way? Or why do you why do you do it that way? I’m just trying to get a sense of the reasoning around some of the decisions that were made so I can better understand, you know, what was going on under the hood there.

I would certainly ask about their operating model design and with engineering. You know, it’s important to understand how a product leader sees him or herself in the context of these other people. And you get a lot of lot of data, you know, from their answers to those questions.

I think one signal is if the team is constantly reacting to what the product needs, like if you’re constantly underwater, the things you end up prioritizing are the things that you learn really late are broken and you’re not feeling like you can be proactive identifying where the product is going, then that means that the team is collectively, whatever the current recipe of folks on the team are, doesn’t have the right balance of being able to think proactively versus just reacting to things that are happening. And so that might be a one good signal of like, well, the division of labor and the time allocation right now just isn’t right.

So you either need to hire a PM to help think about that stuff or hire a PM to help take on a lot of the work that’s happening so that the the right subset of people, founders, or the head of product or designer or engineering, or whatever, can start to think more about that stuff proactively. Because that can be a very dangerous slippery slope if the team collectively ends up just being reactive rather than thinking about where their product should be going. So that’s one.

Two, I think another signal is if the team is getting large enough that there’s a lot of communication lossiness around, We’re doing a lot of stuff now, but not everyone’s clear on what the priorities are and we’re feeling really disheveled and organized just because it’s like becoming very expensive to keep everyone on the same page. That can be another signal. You need help. Those are probably, I think, the two most powerful ones.

Well, I think the answer to this question should differ depending on the stage of the company. The needs and the skills that I’d look for in a PM at a very, very small company would have some subtle and important differences compared to what you would look for at a company like the size and scale of a Twitter. I think from a skill standpoint, I think at an early stage, a PM needs to be like an infectious truth seeker of what customers need and want. Like, they need to be immersed in your product.

And if they’re not immersed in your product, they need to have the right skills that will make them the most intimate understander of all things that are working well and not working well about the product. They need to be like ruthless about spending time with customers, and they need to be just hoovering up as much data points, either qualitative or quantitative around like what’s working and not working at the product. That’s one. Two, they need to be incredibly comfortable with ambiguity, with kind of doing whatever it takes.

Like the startup mode in particular, think, there’s so many ambiguities of being at an early stage startup and it is not an environment where people who need extreme clarity can thrive in. You need to feel comfortable wearing multiple hats. You need to be comfortable doing things as part of your job description that may not necessarily be part of the classical job description. Sometimes see, like, folks that have only worked at larger companies struggle with this because they’re so used to having a lot of structure and clarity around, like, okay, my job is this, and therefore my expectations are this.

And so I think that having someone who’s comfortable with ambiguity and comfortable wearing multiple multiple hats and comfortable doing what it takes to scrappily make things work while still having an eye towards making them more durable over time is really, really important. What

I think hearing about their experience, what folks have done in their prior roles and what challenges they overcame or, you know, even just like asking very high level prompts like, what’s the gnarliest, most frustrating thing you’ve had to deal with in your last role? Either some customer problem you had to solve or some team dynamic that was really stressful, and how did you navigate it? Like, people will direct you in very helpful ways if you give them prompts about their own experience, and that in itself can be very illuminating.

Right? Hearing them share their recollection of something that they perceived to be challenging for them and how they overcame it and how they navigated it. I think in those stories, you can learn a lot around, a, what they’ve experienced and b, how they think about these challenges. So it’s always imperfect when you won’t really know until you work with someone, but soliciting these anecdotes of their experience can be far more helpful than that sort of cookie cutter interview questions that are easy for folks to have good prepared answers to.

Do you have favorite questions that you do like to ask in product

I like the really open ended questions that will solicit the stories. Right? Like asking folks to describe something they’ve worked on in their last role that they’re most proud of. You know, what’s something you, like, completely whiffed and failed at? You thought it was totally gonna work, but it didn’t. And, like, what did you learn from that experience? I think it’s important to hear about interpersonal challenges too, like, you know, what’s an area of conflict you’ve had, especially for folks that are coming into a larger environment or larger team, like, me through really gnarly interpersonal conflict you had and, like, how did you navigate it?

Like, what is one product that you use every day but can’t stand using? Like, you wish you didn’t have to use it every day but you do. And then also, like, what’s a product or or service that you adore and love? However big or small it might be, like, why do you love it? I think just getting people to talk about the things they enjoy and the things they don’t enjoy and why is helpful. You learn a lot about them. And it’s less about judging the thing itself and more about just, you know, hearing how they think about it.

do you think many founders go

or make mistakes when it comes to hiring their first product

I think the most classical mistake is actually not in making hiring mistakes, but in making the mistake of waiting too long to realize you made a mistake. In my experience, the way harder thing, I’ve made this mistake plenty of times myself, you just realize that too late, and it takes too long to transition that person out. And that is really, really expensive. It’s expensive for the hiring manager. It’s not doing any favors to the candidate who will likely have a better chance succeeding somewhere else, and it’s not great for the team.

Teams who work on really hard problems can either be incredibly inspired by the strength and quality and camaraderie of their teammates or can be incredibly demoralized by a teammate who’s just not the right person for the right role. And that, I think, is the far more common mistake of just taking too long to figure that out.