Why great product leaders should stop obsessing over the roadmap | Diya Jolly (CPO & CTO of Xero)

Brett: Let's do it. Thanks for joining.

Diya: Thanks for having me here.

Brett: Um, so maybe a place to start is just your definition of what an excellent chief product officer does and what's the impact they're having on the business.

Diya: Yeah, I think a lot of people think a good chief product or an excellent chief product officer actually helps ship stuff. Uh, but that's from my experience, far from the truth. The key job of a great product, uh, chief product Officer, is essentially setting the direction, not worrying about every single feature, not worrying about even big, even reasonably reasonable sized products down to every feature level, but set, uh, setting the vision and the direction for the product, but which then aligns with the vision and direction for the company.

And then building a team around it that can execute down into the details. Because if you have a chief product, most people think a chief product officer is someone that decides the roadmap, someone that decides, uh, how each, uh, feature, uh, uh, how each feature ships, how it's designed, et cetera. And I don't think you get really good products, um, based on that.

So that's one. I think the other thing for, uh, an excellent chief product officer is just like understanding your customers deeply so that you can decide what bets to make. 'cause you can't make every bet. And so if you don't truly understand your customers deeply, what ends up happening is you make bets that don't really add value.

And then the third thing I would say is resource allocation. Right? Where do you actually, let's say you made four bits, they're not all equally important and they're not all equally complex. So how do you design your org, design your resources, or allocate your resources in a way. That you can move those forward.

And people think resource allocation or organizing is a one-time thing, but it's not our, our, the world around us these days changes every quarter. So these are decisions you have to revisit almost every quarter.

Brett: Do you think that definition that you outlined is the same for all great companies, or do you think the chief product officer role is quite context and maybe CEO or founder dependent that you're working with?

Diya: So I think that the basics of being able to explain to your team, um, the direction of the product, uh, understanding your customers and resource allocation bets and resource allocation is the same. I think the process of getting to it is very different, different companies. So if you have a founder as a, as a, um, CEO, the founders had a vision for a while.

So really is you can't go off into a room and, uh, with your team and co-create a vision. That's usually hard. 'cause I've worked for a founder. Um, I was at Okta before Zero and I worked for a founder. You have to co-create the vision with the founder and to, to a very large extent, actually influence the founder because at the end of the day, they've been thinking, dreaming of this for 10 years.

What you can often get to the table is the depth of understanding of the customer. That's where you, you, you are. Um, that's where you can come from because very often a founder starts with a deep understanding and intuition of the customer, but then they're running a company at the end of the day. And so it, the it loses, it becomes old that understanding, and that's where you can help co-create the vision.

So that's one. Um, I think if you are working with more of a, I'd say an o, um, of a executive, CEO, um, you have, you still co-create the vision. But you co-create the company vision almost because product is such an important part of the company vision. And then once the company vision is co-created, you then have room to actually genuinely create the product vision.

Ex operational CEOs are not in the, why does this button on this, uh, UI look different? But, uh, founder will be in that much of detail.

Brett: Do you think it takes a certain type of chief product officer to be successful in a founder run company that is different than a hired CEO run company? Or not really?

Diya: I think definitely.

Brett: Talk more about what, why that is,

Brett: because you've obviously done both

Diya: uh, yes. I, I think, um, and I was at FreeWheel, which was founder, founder led as well, um, with a very strong product. I think, um, the difference is you have to be wi will, you have to be willing to give up some level of autonomy when thinking about the product

Brett: in a founder like

Diya: in a founder led company.

Um, and you have to be willing to, um, you have to know how to influence really well, and you have to be able to understand what influences the other person. Uh, because often for, for operational executives or of, uh, executive CEO, it is, um, the metrics are clear. Business growth, customer happiness. For a founder, often they're what makes them a founder.

And I try to start a company and I, and I kind of got a taste of it, which is the reason they become successful is the whole world says they're gonna fail. Nobody likes their idea about them. So their gut instinct made them, or their, whatever insight they had is what made them, made them succeed. So more often than not, they will go by their instinct.

Whereas I think, um, an executive CEO more often goes by repeat patterns of things that are known or data. And so how do you influence in either case is very different. Um, and I think, I think the, the being with a founder, C-E-O-A-C-P-O with a founder, CEO, requires probably more EQ and understanding into what the founder values in addition to just the business growth.

Brett: What's that dynamic of sort of like navigating that feel like particularly, 'cause I would assume to your point, one of the things that are special about founder run companies, not always different than, than externally hired CEOs, but they have this feel, and to your point, gut instinct for the business and the customer.

And so it seems, you know, you join and it, it seems in one way you can be overly deferential

Brett: and then in the other way, not. Push back enough, like there, there seems like a, a, a, a very specific tension that you have to navigate.

Diya: Look, at the end of the day, founders want the companies to succeed, right? Um, so that's one thing. So if you put the, put the best of the company before and you are recognized, and, and I think this is true for anyone. If you have a team player in any company that puts the company before themselves, then people know where you're coming from, right?

You're coming in the best interest of the company, you define the outcomes and you de debate the outcomes, right? So I think that is the way to neither become def deferential nor to become, nor to, and to not be able to have an open debate. So, um, I think always take it back to what you're trying to achieve.

That's important and that works across the board how you, how you drive to, or how you convince someone. Maybe different ways. One is more like, well this is the world we could build if we did this. And the other is these are the customers we can go target and this is the revenue we'll get, or this is the value we give the customer and they become more sticky or the lifetime value or whatever you wanna do.

So I think those are different. But at the end of the day, if you are aligned in the outcome, I wanna build a great company. I wanna build a great product for, uh, for, for, uh, uh, for, uh, my customers. And I don't care where the idea comes from. Right. The other thing everybody thinks is like PMs or CPOs are supposed to come up with the vision.

Like, honestly, like a vision is a collection of people coming together and understanding customers deeply enough and stitch and, and then yes, usually a CPO will stitch it together. But honestly, unless your jobs, there are very few people running around that like just sit in a room all day and can like, be like end to end.

This is the perfect thing to do.

Brett: Do you think about value to the customer or value to the business?

Diya: uh, look, I think I am a firm believer that if you add value to the customer, you will find a way to, to capture the value eventually. Mm-hmm. And yes, I, I almost think of it as if you cannot capture value, then you are fooling yourself that you added value to the customer. Hmm. Right. Or enough value to the customer.

So I think, I almost think of those two as interlinked. And if you go with, I am adding, if, if you focus on adding value to the customer, you will figure out a monetization model eventually. Mm-hmm. Um, or how to monetize it. So that's one framework. I, there are other frameworks that are hard, that are easier to do.

When you do, um, large, large scale planning, so like annual planning, you always wanna make sure there are rules of thumbs all over the place. I'm, I'm I, I'm a very Google pm In some ways, um, 30 to 40% on existing customers, 30 to 40% on new time, 20 to 30% on things that are really big moonshots, right? Like depending on, depending on, and so you use those interchangeably, right? You, you go by the rule of thumb, but really rule of thumb by itself does not work in all situations. So right now, for most people, you better be taking a lot of risk in your roadmap, right?

On things that will work or not work. So, um, and these rules of thumbs don't really work right now with everything that's happening with technology

Brett: Share. Share more about that.

Diya: Well, I mean, I think right now where things are at, you are. If you look at, if you look at what's happening with ai, um, we all know, yes, AI will automate things.

We all know AI will give you more insights, but what will it change in the product, in the workflows? Will, will apps become headless, right? Um, what does it mean in terms of, for us in accounting, do we take risk on the accuracy? Should we, in which cases, these are all like risks. Do, do we, like, does our workflow change now from a workflow that drove action?

Now, agents are driving actions to a workflow that does reviews and proves it took the right action. These are all unknown, right? So we did something called, uh, we built, we built, um, and this is a great, this is a great example. We built, um, automatic bank reconciliation. What this means is your transactions in an accounting system are matched to your cash in your bank. And, um, our customers are like, no, no, no, no, no, no. You can't do this. You can't do this with a machine. There's so much nuance to it. What do you mean? Yeah, I will do it.

Brett: and accuracy is just.

Diya: Trust. Yeah. And we're like, okay, but like, it seems silly not to do this. And so we're still like, we'll do it. But in the process of doing it, a we achieved, uh, 97% accuracy.

So we saved them like 22 hours. Uh, each small business, 22 hours a week or, or a month, sorry. Um, and then, um, the thing we learned and we iterated our way into was people are uncomfortable till they can, till they can see what you did. The second you can show them exactly what you did, people are happy. So, but when we went into it and we went into it relatively early, it was unclear if this was a ton of effort that was gonna be completely wasted.

So I think, but if you didn't go into it in this era, two years later. We would've been way behind, right? So I think the pace of change is so fast right now, and the customers themselves are changing the way they use and behave with products that they themselves don't know what they'll be comfortable with.

So you do have to take some leaps of faith and, and take more risk in what you're building right now if all you're doing is what customers are asking for right now. I, I think you'll get left behind.

Brett: Going back to sort of the start of the conversation, when you think about being effective as a chief, uh, chief product officer, what does that now look like? You know, let's say in 2026, you want to make more bets that are obviously ev positive, but are lower probability. But the payoff could be enormous or at least high variance.

Uh, there's a wide degree of uncertainty and you have to execute through it to, to sort of understand it. How do you go from that in a very high level sense to what is gonna happen at any VIN point in time? And then to the point you made at the beginning, how you think about resource allocation.

Diya: this, this is, uh, this is a great point. So we actually, um, are just doing this, which is la what, what we're bets over the last couple of years in, in AI now have. Not mainstream. They're in your 20% bucket, but they're not the, or the 20% moonshot bucket. It's not moonshot, but it's like innovative. And what's truly moonshot has become even more forward thinking.

So like, what could

Brett: what? Yeah, what's the difference between.

Diya: so an exact, so an example is auto bank reconciliation worked? Can we automate book close? Can we automate, um, can we automate tax emissions? Right? Um, that's the, now, now that's the thing where like, can you automate data capture? Like, can you just, can you, can, those things are becoming more common.

Like they, you, you're almost sure, like if I can automate, if, if reconciliation works, you can automate books, close books, close works. You can automate tax, right? So those don't seem like things that customers wouldn't adopt anymore. It's just a question of how to build them at Resource allocation used to be a problem. Today you can get a lot of certainty whether you're in the right direction or not, with a very small team reasonably fast. The question more is how do you, how do you make sure they're not sucked in by the system and the current ways of doing things?

Brett: Say more about that.

Diya: Um, so innovation off or different ways of thinking often happen when you have, when you have to start with nothing, because then you have to think of a new way to do it, because if you do it. If you do, generally do it in the same way, the, um, let me think of an example, uh, an easier example here. So let's say we are thinking about if we were to start an accounting software company today, or a payments company today, 'cause we're both, what would it look like if you're sitting in an existing system?

There's so many constraints as well as so much distraction that it's really hard to rethink it from scratch. So, um, a person would go, well, okay, if I'm gonna rethink an accounting system, our ledger does X, Y, and ZI need to think how I can build something to fit this. Whereas somebody that doesn't have a ledger would start from, okay, what is the experience and then what do I need to build from there?

Um, somebody doing it in the system would go, okay, I have this other thing to worry about. I have this meeting to attend. There's this team meeting to attend. Uh, and so there are multiple constraints in free space, like in, in, in the ability to think and go deep. Um, you tend to go to your existing customers, which often they may not be the, the tech, like the early adopters, right?

Um, so I think it's just generally relatively hard to innovate something from the ground up that is completely new in an existing system. So the question becomes, how do you find a team, invest in a team, create a team, and keep them sheltered so that they're not sucked in by the system?

Brett: Is it just doing that is the answer or there's nuance to how you do that? Well,

Diya: Well.

Create a startup, if you're really, so then you have to find the right people, the right teams, the right goals. It looks, in many ways, it looks very much like what you guys do, except you can only lay one bet on one team and one set of people. So the probability of success also is much lower. Mm-hmm. But the difference is you have, you do have some industry knowledge or depth of knowledge, and you do have a hypothesis before you go in.

You don't, you don't just say, I'm gonna start a team on the site that's gonna innovate. You say, I think the world is gonna evolve in this way. It's simple example, SaaS sa uh, SaaS versus, uh, license based model versus wanted to build a transaction based model. Super hard to do it in the current system.

Existing customers will revolt. Uh, billing systems won't work. Uh, sales incentives won't work. But if you put someone on the site, this is something very easy for people to understand. They have none of those constraints, right? So your hypothesis is transaction based mo eventually the world will move to a transaction based model.

It's not a, it's not an it's, you're not going and saying, oh, just figure out what to do. That's why t

Brett: Building sort of on the AI theme for a second, what do you think is different about being excellent as a chief product officer in 2026 versus excellent as a chief product officer in 2022?

Diya: I think a couple of things. I think one is, so we talked a little bit about this. No longer understanding your customers is important, but understanding your customers can mean multiple things. Understanding your customers can mean what they're asking for, uh. Understanding your customers can also mean bringing technology to bear in a way that they don't know what they need.

The second is obviously harder, and that is more important now. Okay. So it can't just be, I go have a bunch of customer conversations. These customers want x. It does require a depth of understanding of what the problem is. Um, an example there is, um, a good example there is we were being told repeatedly that we needed to, um, we needed to show the actual bank statement, um, during the reconciliation process. And they're like, you have to show it. You have to show it. And when you dug deeper, as an example, as. The issue was not that we weren't showing the bank statement, the issue was they just wanted the total. So we could have calculated our total as an example, this is not an AI example, but like this kind of thinking, like normally in the old, in the before ai, you could have gone there and been like, Hey, um, the customers asking for this.

You dig a little deeper into the works here. If you don't truly understand what they're trying to do and how you can bring this new technology to bear to make, to deliver even more value than they're asking for, it becomes hard. So that's one thing. I think the second thing is it's not so much about like, I need to give this capability anymore, right?

It is more now the way you need to think is how do I make their workflows easier, right? It's shifted from here's the capability, do they do utilization to how do I take what exists in front of me and, and collapse the workflows and make it easier so that in a lot of cases. You, you create new outcomes of time saved, um, uh, business grown, right?

'cause you can, you can actually do stuff for the business now. So I think it, it's just a different orientation.

Brett: Do you, from where you sit right now, does it feel like incremental change or it's trans just night and day? E Expand on that a little like, like those, I, I understand sort of those two points, but like when you pull on that, why is that so profound?

Diya: the concept of an app has changed.

So your ability to think about a customer's entire day in life is just like, you can no longer think my customer wants to do this in an app. You think you have to think, uh, my customer wants to get paid by their customer. What is the best way for me to get them paid? Versus I'm gonna put a button that resends an email, right?

Uh, uh, resends an email to ask their customer to pay. Uh, now it's like. Can I bring them on WhatsApp? Can I remind my customer, ask them if they're visiting? That cus like it, it's so many other, like, can I send them a text message? Um, how often should I do it? When should I remind? What's the best way to get paid?

All of these things are a lot more possible. So you, you're designing software and not with I'm helping humans conduct work, but I'm actually trying to get to an outcome.

Brett: Do you think you are flying at a lower altitude on average, more in the details or the same,

Diya: That's a good question. Uh, yes. In these areas I'm flying at a much lower altitude.

Brett: and what does that look like?

Diya: That's a very smart question. Um, I think, I think it's being, I think while you are, and here's why you're flying at a lower altitude, because you're trying to change the way people work. You're trying to change people because you, as one of, as you as the senior product and engineering leader. Are the catalyst for change right now, right? Because otherwise people will just keep doing what they do. So I think the way things look is someti you are having deeper discussions on, you are more in the initial sausage making, you are having deeper discussions on, um, what should, uh, how does the technical architecture need to change to be able to support, right? Like usually technical architectures are reasonably well understood, but now it's like, should we do this so we have more flexibility?

Should we be model agnostic? How quickly should we be able to change models? What can be probabilistic? What cannot be probabilistic? What has to be deterministic? Um, do we need a UI here? Will the UI be chat based or will it be a, will it look like it's traditional? Should chat be a sidecar? Should chat be the ui, right?

Like, so you get into this, all these levels of detail because you're fundamentally changing the app. Three years ago, we would've said. Oh, I'll give you a very basic example. Um, we want to do, we wanna, let's build for the mid-market segment, right? Like we don't just wanna be small business. You'd go and say, okay, can you guys figure out how to build for the mid-market segment?

And, uh, let's go figure out. And you'd do a bunch of customer calls and you'd be like, okay, here are the list of features we need to build. And then your team's been through the process of like building the us trusting the work, like building the workflow so they could go work autonomously and then come back here.

Every decision starts becoming very strategic and fundamental to the direction of the product, the way it evolves, and the tech stack, the way it evolves for the future. Mm-hmm. So yes, you are much more in the sausage making.

Brett: what's your definition of politics or a political company or executive team?

Diya: Whenever there are more than two people in the room, there's politics. This is at home. This is in homeless 'cause you've lived with each other and like, but this is everywhere, right? Like it's three people, which means any two can have an opinion that the other person doesn't have. And so the weight has changed on the, on that one person that's left out.

So to me, like I think I accepted long ago, whenever there are three, if you have a company of three people, there's politics. Mm-hmm. Right? Um, I think to me politics means at its core form two things. People are not rowing in the same direction. Okay. Um, which means there's friction in the system to achieving an outcome and people are carrying more burden of convincing, influencing, aligning than they have to.

And then I think that politics and then at the surface level, if you touch the why it is incentives are not aligned for some.

Brett: What about when you think about the, the different businesses that you've worked at and you think about the most political environments and the least political environments, what's going on? Like, what is a CEO doing that's different? What is an executive team, you know?

Diya: a, yeah, that's a very good. So I think one is, so, so when I talk about incentives, the incentive system has to be set well, right? But, but by the CEO and then subsequently by the executives. Um, I think two things. When a leader jumps in and solves problems across their teams, there is a lot of reason for the teams to lobby for their self-interest, right?

Which then creates a me versus them. When a leader rewards collaboration, even if the collaboration resulted in an imperfect situation, um, as much as they reward impact or enough, like impact is important, but like enough. Then I think that sets the behavior of collaboration because it is an outcome that is, again, it goes back to incentives.

If, if you are, if you're recognized for it, you will do it. Right. Um, if you reward putting the company first versus the best answer always. Okay. Um, that's a system where, where, uh, that's another thing a CEO can do, right? It's, and, and when you say reward the company first, it could be, you may have the right answer, but in executing this, you are going to actually make a hundred people demotivated, right?

So is that ultimately the right thing for the company? If you think like that and you reward that, I think that is, that that is what leads to lack of politics. And then I think, look, I think the other things are how safe do, like what culture, like do you create a culture of. How do you support your people?

How safe do you feel? Because when you feel safe, you're, you don't generally, you're not generally looking, um, you're not generally looking to, to, when you feel safe, you generally tend to act in the best interest of the environment, staying same. When you feel unsafe, unsafe, then you either want something for the environment or you wanna change the environment.

Brett: When you go back to the, the comment about, um, the incentive structure,

Diya: Yeah,

Brett: can you make that more tangible? Like what if incentives are important for a whole host of reasons, but one is to get people to do what's best for the company, is maybe one simple way to think about it. Talk about like the different levers.

Diya: yeah. So examples, um. If somebody did not, if somebody's project did not go well, but they went outta their way, project product launch did not go well, but they went outta their way to, uh, make another team better. Do you increase their comp? Does that go into their performance? Is that recognized it on all hands?

Brett: Do you think that is more important, less important, or the same importance, uh, versus comp?

Diya: I think there is a balance. You wanna work in a culture where you feel empowered to do the right thing you wanna work or empowered to move away. Actually, I should say this differently, autonomy, sense of purpose, growth and comp. They all need to be balanced. Um, I don't, I don't think most people for long periods of time can just be coin operated.

It's just really hard. Human beings are not made like this. It's just really like, imagine working in an environment that gives you a ton of money, but you do it again and again and again and again and you're doing the same job again. I just don't think it works long term. You tend have a of attrition,

Brett: So you talked a little bit about the importance of creating a, a safe or or, or supportive environment. What are your thoughts on, on when you're leading a function, the role of being demanding and having high expectations and like how those fit together?

Diya: I think you can do both,

Brett: Talk more about that.

Diya: I. I think you have to do both, right? So if you demand, you have to demand a lot to get results, especially in this day and age, right? Uh, but if you demand without giving people the support to succeed and letting them know that taking risk is okay, and failure is okay, you're gonna have a culture where nobody takes risks.

Nobody tries to grow. And, um, everybody is, um, it's a fear-based culture. There's no innovation, there's no growth. Everybody's doing the easiest things. Your roadmaps are sandbagged, your revenue numbers are sandbagged, right? Like nobody's willing to take risks. So I think what I tell my team is like, look, we can't know the future.

We can only try. You can't be wrong a hundred percent. You, you can't fail a hundred percent of the times. But I don't expect a success, a, a a a batting average of, I don't expect a batting average of a hundred, a hundred percent. I expect a batting average of depending on level 70, 80, 70%, et cetera. This is like, if you, if you go back to OKRs, right?

Your OKRs should be that your average should be 0.7 in the score of the okr. Mm-hmm. If it's always one, you haven't stretched yourselves and it should be okay to be 0.7. So that's what I mean, right? Uh, by creating an environment that's supportive and, and allows you to stretch. Um, so that's one. I think the second thing is when a person is fitting into, let, let's say somebody gets promoted and is trying to do a new role, can you make sure that.

Not you personally, but you've created a culture where there's enough support around them. How do I do X? What does it mean to do? Y Can you give people enough time to grow into their roles? Is another example, right? If somebody takes a huge bet, can you go? So for example, um, uh, we took a bet where we said, and I, and I did this.

I'm like, I don't wanna wake up in two years and find out that the entire app is agents in a chat. So we're gonna go off and build our own app on the side. That is where you're gonna do accounting from a chat, okay? And it's all agents. And the effort failed mainly because customers are not there. Like they're not ready.

And maybe accounting will never become purely chat just because of the amount of data. Uh, but can you sell it? Can you. But the team we had there, can you like celebrate their failures, right? Can you celebrate failures You learn from? The question isn't, shouldn't be, did you fail or did you not achieve an outcome?

The question is, what is your batting average? Is it an acceptable batting average? And then when you failed, did you learn from it? And are you repeating the same thing multiple times?

Brett: Do you find that a portion of your job is to raise the ambitions of the org and, and, and you, somebody says, well, you know, we can ship it on,

Diya: That's literally my number one job.

Brett: expand on that.

Diya: Um, it's very interesting if you are, what you get, as you get more senior in the org is you start noticing things across teams and you also right for your, your wrongly have input from outside the company and have. And your job is to bring input from outside the company in terms of how, how things should function within.

And so you, you're not stuck in the doing as much, so oftentimes you have more perspective. We just went through it. My whole team is so stressed out that we've over committed for next year and I'm like, nah, I don't think so. Uh, because, uh, I saw us go from as, as a system, not as individual teams because you're there looking at their own teams.

I saw us go from a velocity of x to a velocity of y from a ch architecture change of X to an architecture change of YI am seeing the trajectory, I'm seeing which teams are of outperforming the trajectory, which means other teams can get there. And my decision's based on that. And I'm, and, and I'm seeing where the slack in the system is.

So I think you do end up getting a better sense in many ways, unfortunately, of how far you can push the teams. And so your job is to get them to rise to that level. Now, if you are always unrealistic, somebody told me you're being unrealistic, right? Like, they're like, when you talk like this, it sounds like you're unrealistic.

And I'm like, okay, lemme show you the data I'm seeing. The data I'm seeing is, here's the benchmark here, here's where we are at the be we've increased by, uh, productivity by let's say 50% in the last two years. And the world is increasing productivity by another 50%. So we should be able to do that. We'd like, we've caught up the world.

There's no reason we cannot. And oh, by the way, here's where I think the slack is. They're like, oh, that makes sense, right? So I think, I think often your job is to raise ambitions and push in a way where if you push so hard that people always fail, that is a doom loop, right? And then people are gonna start saying, yep, sure.

We'll say yes to you and it won't work. So there's this judgment call of like how far you raise the ambitions. And then what data are you ba raising those based on? Which is usually not the way people think about it. Like usually people go and say, here's the amount of work I have to do and this is how long it'll take.

And this is what it means. You look at more macro trends and, and and, and, uh, both inside the company and outside.

Brett: And based on that, it's, it's more quantitative where it's really, there's just a, when you're really experienced, this is getting this right. Okay.

Diya: It's both. It's a combo of both, right? It's not, it, knowing that X team is performing better than y team is really hard to say what is performing better?

Brett: Yeah, because it's complex.

Diya: It's complex, but knowing you're getting more output from this team versus this team, and so this team has found some secret, why can't you raise your other team to the level of this team?

That's a gut call, right? Going. Yes. I think the complexity is the same. Yes. I think. People on this site might need a little bit of change or need to learn a skill or something. Those are gut calls. There are also, obviously you can benchmark externally, benchmark internally and go, we did X last year, we did y the year after.

And like industry benchmark says, here's how productivity is increasing.

Brett: Who in your career has done the best job of this, of, of demanding the most of you? And like, what's the story behind it?

Diya: I'll say Sukhinder, has probably taught me more than anyone I've learned in the last, like, like it's taught me an exceptional amount while giving me a tremendous amount of autonomy, uh, on things that I know well.

Brett: What, what, what did she teach you?

Diya: Um, how do you raise, how do you, how do you keep raising the bar while being supportive? Right? Um, how do you mix? 

Okay. Um, global, never Xero is globally so complicated. How do you globally scale this way? Right. What excellence looks like outside of product and engineering? What is excellence in marketing? What is excellence in sales? Or what's excellence in finance? Right? Because here I have someone who is actually an expert in all the domains I'm not in.

Mm-hmm. Right? Um, so, and relent, relentless relentlessness. Just how do, how are you relentless without tiring our teams up?

Brett: what do you find very tricky about being a chief product officer? What's really, like, you've been doing this for a while, what's really hard about it? Or maybe if you're not in the seat, you don't quite get it.

Diya: I think a lot of people would think it is about making a lot of decisions, and I think the more senior you get in any role, especially in the product role, it is about making a few decisions that are big and irreversible. And you need more time to think than to do. And the only way to get there is to have very, very strong lieutenants, which I've been blessed with.

I've been able to build up my team to have that so that you actually don't have to do a lot of the execution. So an ex, like I said, like I'm not gonna, I'm not gonna be able to execute my way out, or my team's not gonna be able to execute their way out of whether what a headless app looks like. That's a deep thinking.

You need time. Um, you are not gonna be able to execute your way out of what the next genus, uh, SaaS app looks like, right? You, you will do a bunch of experiments in the wrong direction. So I think that's what people, people think it means. More reviewing, more doing, and I think it actually, you, you need to be very focused about which decisions matter and what matters, and then spending time on those things.

I am. Famously, I am awful at email because I'm like, email is tactical. Right? And I, I, and like, I'm terrible at it. Um, and people, it's not because I run out of time. It's because I'm like, okay, that's today's problem. And I, and there are enough people in the sys in, in the org that will solve it. My job is not solving today's small problem.

My job is figuring out where we should go in the future. And I think that's not, that's a good functioning org and that's not understood very much. I think oftentimes when you step into the role, you go, my job is like actually making sure everything is done.

Brett: Is it easy for you to figure out what are the decisions that you really have to sit with and wrestle with versus those that should be pushed down?

Diya: Uh, so I have a mechanism. So there are two mechanisms, right? Mechanism is I will push down stuff. And then wait and see what fails. Okay. Because often if I try to do, I may hold too much, but I'll generally push down stuff and then like keep enough of an eye to see like if it, if it fails or not. Actually I'll push down stuff that has impact below a certain amount and not worry about it till somebody escalates.

Then there's stuff like this really matters for competitive next year. Like this, this set, this set of pro or this product we're launching or this. Um, so we were building tax in the uk. That really like is a big, meaty thing that can change our position. If we can do integrated attacks, uh, um, uh, closing your books to tax, I'll push it down, but I will make sure I have enough status updates to know when things are going well enough in as light touch away as humanly possible, or I've delegated it to a direct, um, that I have a lot of faith in that is delivered weekly, in which case I won't worry about it. And then there are for all other, and for, sorry for the big restart. Sorry. So I put decisions in three buckets. One is like impact on the business, but like not make or break for the business. Those are delegated down until somebody escalates decisions that have big impact on the business. But what you have to do is fairly certain, in which case I delegate it down, but have, but do keep an eye.

Whether it's by putting a trusted lieutenant that will raise, escalate that I trust to cash the issues and escalate. Or by making sure there's enough status update. And then there are decisions that are just ambiguous. What is a, again, I go back to like, what will the UI of tomorrow look like? Mm-hmm.

Right? That, that you just can't delegate. Um, so most of my time is spent in the big things that go wrong, right. And even more time is spent on the things that like, are just ambiguous. You just don't know the answer.

Brett: How much of a given week or month goes into those big, ambiguous,

Diya: Uh, 50 plus percent. 50%, right? No, 50%.

Brett: I feel, I feel like great executives would want to do that, and then the day to day just gets in, in the way of that, you

Diya: Uh, so I, I have a right. I do two things.

Brett: you never respond to an email. It saves you a lot of time. The more you're, if you respond very quickly, what happens? You get more email.

Diya: exactly. So I, like, I eyeball an email and it's truly breaking. And I, in many ways it is bad because I forget, like I, I don't get to urgent emails sometimes, but people know that they can find me on the phone if it's truly urgent, right? Um, but yes, I am notorious at being awful at email and Slack like awful.

Um. My, my trick is the following. So I actually will carve out one full day where I will not do meetings right? Every week. Every week. It doesn't matter. I will not do

Brett: And you really protect it.

Diya: I really protect it. Um, and again, like people will tell me I have more flexibility to do that than others, but, but I will try really hard.

The second thing is, it is harder in this job, but I also protected, uh, at least two hours a day. Um, usually at the end of the day, my brain, I'm, I'm a night person. So like I, most of my creative ideas happen, like unfortunately between nine and 12, uh, it's harder in this job because of the global nature. Uh, but I would do that, but that's another thing I do.

So I, I, and then it's not only about thinking yourself, then it's like you have to bring people into a room. So I, most of my ears laugh because I am militant about my calendar. Like I'm literally militant about what meetings get, get on my calendar. Um, and I'd say you don't always need 50%. Like, but right now, if you are not spending 50% of your time thinking about what your product will look like, what value it'll deliver, it's just gonna be hard to compete.

Brett: And so.

Diya: And you have to be blessed with a great team. I, I, in the last three years, I think I'm at a place where like I can close my eyes and my team can do it, ton of the heavy lifting on day to day.

Brett: So when you have this, step one is creating the time for it, what do you actually let, let's say on tomorrow, Friday, you have the whole day clear.

Diya: Yeah.

Brett: What are you actually doing to work on these really important, ambiguous problems that at least in your mind are, are kind of your core jobs?

Diya: Um, so I'll pick one, right? Um, I, I won't say I'll make progress on all of it. So at any given time, I think you can go very deep on one. So let's say, um. I take a new problem 'cause I've been talking about how the apple will change for a while. Let's say, I wanna figure out how SAS models are changing. So tomorrow, tomorrow I would go, um, close all the tabs that are open.

Uh, basically I actually switch my browser from Chrome to Safari so that I can't actually get into my work browser and literally go and see like, what are people saying about it? Um, has anybody else done it? What feedback have they gotten? Can I try a product like that? Um, if I were to write down what it would take us to move in that direction, what would I be worried about?

What would I not be worried about? Um, what are the risks? So it's really is like just exploring the world outside. It's, it's exploring the world outside, gathering information, coming in, thinking about it, building a structure from where you can have a debate, right? Teeing the debate up. Okay. Um. Maybe you could likely for something like this, you can't tee a debate up in one time.

Right. Um, you probably do this for like, let's say 2, 3, 4 weeks, and then you can tee a debate up and then it becomes, okay, if you've debated it, then you go, okay. Now that I've debated with everyone, it's big enough where like, I need to give it more structure. So then for the next 2, 3, 4 weeks after that, it'll be, I'll be giving it structure, trying to write either a document or build a prototype.

Now it's very easy to build a prototype. Mm-hmm. Um, and then it'll be okay, bring it back. Either at that point you hand it off to someone, or if it's still too big, then you take feedback once again, socialize it so that that's what you would do. And then, then when it comes to execution, you're very clear on what has to execute.

Brett: When you think about the last few years in this category of very big ambiguous problems that, that you have to solve, what's, what's the one that is like you really nailed? What's the story behind it?

Diya: So I can give you two very different examples. Um, one is an old world example, not ai. And then I'll give you an AI example. Um, an old world example is. How does a company like Xero compete in the us right? This was, um, uh, our, our, uh, uh, head of m and a, right? How do we compete in the us? Like it's very clear if we just do it organically, it'll take too long. But what is the right bet to make? Is it if we do something inorganically? Is it to acquire another bookkeeping provider here? Is it to acquire tax provider here?

Is it to acquire? Like, what, what should we do? And I think we bet on, we bet on lio, which everyone knows we've, we've acquired Lio and the, and the decision we made, which since has proved out to be, in retrospect, proved out to be an amazing decision, uh, is. For small businesses, the most important thing is their cash flow.

They don't think about accounting, they don't think about, like yes, they think about paying people as a, yeah, as a, um, as a, um, re yeah, as a requirement, but cash flow is most important. Mm-hmm. And two, if you could build a way, if you could own controlling their cash flow or making the them have better cash flow, that would, in a way that is world class, that would probably be a great way to attract attention and get entry. Invoicing. There are about a hundred, like ar there are hundreds and thousands of companies like, uh, doing ar. So it's probably not the best place to go to Bills, interestingly enough. Um, even before you incorporate a company or you invoice someone. You do, you pay legal fees, you in tech, you might pay to do a prototype somewhere else.

You may pay for supplies. Bills is actually, interestingly enough, the first thing a small business does. So a payments company that is early in the flow of a relationship with small business and then trying to find a company that had the right tech stack, right the right founders, had the right culture, right, had the right uh, product.

Brett: Do you find most of the time that's the case?

Diya: I think most of the times,

Brett: It it is just, is not glaringly obvious. Only in retrospect.

Diya: yeah, I think the big decisions are not clearly obvious and I honestly think like.

Batting averages on big decision. If, if every one of the big decisions you take turns out correct, you're doing something very wrong, like you're not taking enough risk, something's very wrong. So the batting average, again, like I say this like on big decisions, is like if you're batting average is two thirds,

Brett: You doing

Diya: probably doing a good job.

Brett: What was the AI example you were gonna share?

Diya: the air example was, um, interestingly enough, everyone around us in our category was doing was staying away from, um, they were doing, uh, AgTech uh, actions. Okay? Um, the bet we took was AgTech actions are important, but the ability to chat with your app to get financial insights is really important as well.

And insights are gonna turn, quote, unquote, gentech as well. In accounting, people were really worried that what if the thing hallucinates and you return wrong information. We made a bet early on. We call this our insights product. So financial insights where you literally can go to our chat bot jacks, our chat jacks and you can basically, um, do a whole scenario planning.

And when we were making the decision, we're like, can you do this at accuracy? What if we make mistakes? What if we misguide people? And I think in retrospect, just going and saying, we're gonna do it, we're gonna do it at accuracy. Um, and then pushing the teams to do it at accuracy and putting in the scaffolding that was needed for the accuracy.

It completely just, one is like we're ahead in the market, nobody else does it. Uh, second and we're at like 95% accuracy or something like in the answers return. And you can do pretty complicated things. Like you can go, should I add another shift? Should I buy, get a loan? Should I buy a car? Like you could do pretty, like, it's literally like talking to your advisor. Um, but it also helped us just up our AI infrastructure. What I mean by that is how do we do evals? How do, what do we use for ground truth? Right? Like it just because the problem was so hard, it just completely changed the game

Brett: Do you find that often? That, that if, if the, if you sort of raise the bar on what you're willing to do, it forces a lot of the enabling pieces to come into place.

Diya: yes. This is why, uh, as often as I'm called irrational, I'm like, no, you give human beings something to do and you motivate them to do it, it'll get done. We've done way bigger things. We've learned how to fly, right? Like, so

Brett: We got rockets in

Diya: we got rockets in space. Like, we've, like, we've done a lot, a bunch of bigger things.

Brett: Right. Um, what, what's something that has gone quite badly,

Diya: I also think, um, and this is what convinced me, that like while SaaS workflows will change, workflows will stay there. People don't know what to do when they come into an open chat. It's, it's very different. When you come into a chat with something in mind. It's very different when in your workday you open the chat and you go, this is not the core thing.

I think about like. Small businesses don't come to us thinking, oh, I wanna now interact with accounting, or right now I wanna interact with payroll. Right. Um, so they need the structure that guides them through. And then at, I don't think when it comes to finances, people will ever be comfortable without some kind of review workflow.

Um, because no matter what you will want to go, even if you look at the review workflow only once out of 10 times, you will want it to be there and be able to, you will want the audit trail to go back. And the chat only interface makes that very, very hard. And so I think, I think we put in too much time, too much effort into that.

We gotta, the good thing is we got a lot of learnings for our, for our current product and we have some really cool new ideas that I, I'm not ready to talk about yet. But I think that was a thing that we could have shortcut.

Brett: At a business of your scale, how far in the future are you spending most of your cognitive calories?

Diya: Look, the answer differs. Um, it differs from what it was, let's say, three years ago to now. Uh, now things are so uncertain that you're really thinking 24 months and that's become the future because things are moving so fast and nobody knows. Historically, you would be laying the groundwork for more than two years out in the future, right?

You would be going, okay, um, I've set these things that are gonna come to fruition in two years. What do I wanna do after that? How do I start laying the seeds? For what? Like making the decisions and laying the seeds for what needs to happen after that. I think now it's more like, how do I lay the seeds to reach a completely different situation in two years?

Or like, not even seeds, like how do I lay the, like how do I start, how do I start getting the org to execute And, oh, by the way, execute in a very different way to reach a completely different state in two years or 18 months.

Brett: Do you think given the environment that we're in that, that you need just many more bets? Just the total number of bets needs to go up,

or it's more just the nature of what the bets are? Right.

Diya: So saying many more bets is a little dangerous, right? Because they, they, they, it's very like, you could do a hundred things today, but do they amount to something? I think. It is very important to have a, I think you, you need today, if you have one hypothesis on how the world will work, very dangerous. If you have, I'd say somewhere around two to four hypothesis or where the world will be, and then your probability on that, and then, then you line up your bets accordingly, right?

So, um, will apps get more headless? Yes. So like we need to start up, will apps get more gentech, almost a certain probability. So there should be a bunch of resources on that. Will apps get, um, more head, will apps get more headless? Not saying completely headless, high possibility. Um, so you should have some bets.

There will. SaaS apps completely disappear. I, I the will, the workflows disappear. SaaS is an overloaded term, probably not, at least in our category, just because it's compliance. You need, like, you need the workflows to prove that you're doing the right thing to submit the taxes. There's an audit trail. You, you want a little bit of a bet there, but are you gonna put like more than 5% of your 10% of your battery resources there?

Probably not. But you do wanna keep up with the learning so that you can make a pivot as soon as you can.

Brett: Something you only hinted at that we haven't talked that much about is what does it mean to be on an executive team?

Brett: What does it mean if you are excellent in the capacity of being a team member on sort of the e-staff of a company? And is that any different than, you know, you have your executive team underneath you?

Is that any different than being world class as an executive that's underneath you versus this peer set that is running the company?

Diya: When you get to the C stuff, you are truly holding the. Business or, or the, the, the context one is you need to understand multiple domains at some level of depth, excuse me, to truly have impact.

I think especially as a CPO, it's very, very hard if you don't understand multiple domains in some ways. The second thing I think is you are problem solving. You switch between problem solving in your domain to problem solving at the company level. And a great example there is, I can talk about what AI is gonna do to the face of an app till I'm blue with my team and believe that's an existential threat. But that conversation does not make a ton of sense in depth at the C level. What makes a ton of sense at the C level is, uh, with my peers is like, okay, I need, what do we need to do to make our numbers this year? But what do we also need to do to make sure we're there in three years? What does the resource allocation look like?

Oh, by the way, what does that mean from a cost perspective? Do we need to go acquire something? Why in which category? So it, it, it, it's just different. I think you put on different hats. It's not even altitude. I think you put on different hats, um, in those functions.

Brett: When there's a senior PM that is a star and wants to have lunch with you or you know, then you have your direct, and then in between that you have a director or vp. For maybe a few of those different levels.

What's the advice that you tend to give if they want to eventually be a chief product officer

Diya: I think so for me, it's been interesting in that like I haven't said I want Title X ever. Right. The recipe that's worked for me, and this is what I tell them. I'm like, I, I don't know if you should worry about a title. I think if the title happens, great. But you should worry about what you wanna look back at when you end your career and be proud of. And to me it's been a few things, which is how do you continue to grow and what makes you continue to grow, keep seeking those experiences out. Growth by itself is not enough. How are you having impact? Because impact fuels growth. It's just, it, there's like, the more impact you have, the more chances you get for growth. Yeah. And then work with people that bet on you and will help you grow. So that's one, one formula I've used. Um, and every time I take a new job, like it literally is that formula, right?

Um, the, the second thing is I think people get too stuck in one experience. So to the extent you can, and this, this is why I say don't worry about titles, because often you need to go back to go forward, seek out. As many different experiences, whether that means you're working, you do startups, mid-size, big companies, whether you change domains.

Brett: Even if they're not trying to climb the ladder, but they're their expanding scope and impact. Are there bottlenecks that you see that that tend to be patterns like that, that pop up, that get people stuck?

Diya: Being able to demand high performance from your team, uh, often to people feels like, um, you are pushing them too hard and why will they wanna work here and why will they wanna work for you and you're a bad manager, et cetera, et cetera. Uh, and that taking its extreme performance management feels very bad and it's a very hard thing for even the best of people to learn.

I think the second thing that people really struggle with is not knowing everything. The more senior you get, um, and how you balance for that. And I think the third thing people struggle with is not doing everything. Uh, so this goes back to the. The more senior you get, the fewer things you pick as your focus.

And I think the last thing is, as a junior person, so you have the most flexibility to carve out thinking, thinking time. I think at, at the two ends, either you're very senior or you're very junior in the middle. It, it's very hard to carve out your own thinking time because you're at the behest of too many people and too many things and too many fires.

Um, so I think, but if you don't do that, you can't, you can't invest in having higher impact or your growth. Sometimes the investment is for your growth. Uh, sometimes the investments for impact. So those are the places where I see people start, start to sort.

Brett: In each one of those, are there, do you have a piece of advice or, or, or something that can be condensed or is it just too multifaceted?

Diya: No, I think, uh, for the performance stuff, like look, um. You build a gut intuition on what's possible and what performance you need. And generally, your gut intuition is right, like demanding, demanding of other people what you would demand of yourself is never a bad thing, right? Um, and then demanding more of yourself is also not a bad thing. So, so one of my big rules is like, if I won't do it, I won't ask people to do it, right?

Um, this is why I often get told, uh, you do too much and you ask too much of people. Um, uh, so I think, and I think the, the not having performance in a team is actually detrimental to the whole, uh, you won't get the right, the whole team won't get the right opportunities. You won't retain stars, you won't learn from other people than dealing with someone who is not performing well.

Because even one person can push, pull a performance of a team down by 20, 20, 30%, right? Because other people are carrying the weight. So that's one. The second one was getting okay with not knowing everything.

I think the, the, the advice I give people is, and I've had, I've had so many people struggle with this, which is like, you are, you're, you need to hire people who can do their jobs without you. You need to hire people who can step into your role in a couple of years. And by the way, you can learn from today because nobody's immune to learning, right?

Um, and, and they'll obviously learn a lot from you, but you can learn from them. That's the only way you're gonna succeed on focusing your time, on moving the ball forward in bigger things. And I think it takes a while for people to get there. Um. And it's okay not to know everything. It's okay to say, I have to go ask so and so person as long as it is not as long as you know, enough to make sure that things are not off track. Um, thinking time. I think, look, it's hard, but like, this is what I tell people. Like every company has a rhythm. Some companies start really fast on Mondays, but then Fridays are slower. Some companies start very slow and literally run into the weekend. Some companies actually like slow down in the middle of the week, find the thing that works, right?

Like find something that works and try to reinforce it to the best of your abilities. Um, and if you don't ask to, if you don't tell people that that is the situation, people are gonna tra travel over the calendar. This one's easier said than done, to be honest. Um, but you have to find a way. I, when I was, when I was.

A director, I literally would call in sick to get my thinking time once in a while because I'm like, I, I just like, there's, there's like, and I would tell my manager, I'm doing this because you'll respect the fact that I'm, I need to get stuff done and I need time to think, but like, I can't convince a hundred other people, so to them I'm sick.

Brett: Maybe lastly, you mentioned this at the very beginning of our conver, or maybe it was towards the middle when we're talking about politics at companies. Um, what is it that you want your reputation to be

Diya: a great question. So, um, multifaceted but honestly known for actually being able to build products at change industry is one and second, build businesses that help like that last for a long time. Um, is the second.

Brett: good place to end? Thanks so much for doing this. We really appreciate it. It was great.