Greg Sheehans Podcast

Ep 11: Andrew Tokeley (Tokes): Mastering Product Leadership

March 11, 2024 Greg Sheehan Season 1 Episode 11
Ep 11: Andrew Tokeley (Tokes): Mastering Product Leadership
Greg Sheehans Podcast
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Greg Sheehans Podcast
Ep 11: Andrew Tokeley (Tokes): Mastering Product Leadership
Mar 11, 2024 Season 1 Episode 11
Greg Sheehan

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Embark on a journey through the intricate world of product leadership with "Tokes", the Kiwi OG of the space.

From the early days of grappling with technological puzzles to his ascent as a product management guru.

Tokes discusses the crucial relationship between founders and product leaders and even covers the role he played with Xero founder Rod Drury.

You can connect with Tokes via his LinkedIn.



Coal Mine Rhythm - Short Version B by Dan Ayalon

Show Notes Transcript Chapter Markers

Send us a Text Message.

Embark on a journey through the intricate world of product leadership with "Tokes", the Kiwi OG of the space.

From the early days of grappling with technological puzzles to his ascent as a product management guru.

Tokes discusses the crucial relationship between founders and product leaders and even covers the role he played with Xero founder Rod Drury.

You can connect with Tokes via his LinkedIn.



Coal Mine Rhythm - Short Version B by Dan Ayalon

Speaker 1:

May, here you are, Andrew. Exactly what's hoax, as everybody knows.

Speaker 2:

You Welcome, yeah thanks for the invite. I have to say I feel a little. You know everyone talks about imposter syndrome. I feel a little bit of imposter syndrome coming on a startup podcast, having never started a startup. Most of my clients were startups and have transitioned from being startups, so I don't know if I have any pills of wisdom for someone who's grinding it out in the garage right now. But let's see where the conversation is.

Speaker 1:

I think you do. I think you do and I think you naturally are being very gracious, but I think you are. Yeah, you might not have been a founder, but you have been the OG of product in well, certainly in New Zealand, for quite some time. I've known you through the zero ecosystem and that's probably a good place to start. There's a little bit of like you know how you got to be in a product role even first, and then maybe we jump into the zero story. Why product? Is that something? Did you grow up going? I want to be a product guy. What was the? What was the story?

Speaker 2:

No, absolutely not, Like like most people who fall into product. It was somewhat accidental, but it makes perfect sense when you look back at this. And so I reflect on my early career as a technologist. I used to. I'm a problem solving kind of a person. I love puzzles.

Speaker 2:

I, you know, I found engineering when I was studying statistics at university and fell in love with the computer side of that rather than the science of it, and through that worked for an agency and discovered this sort of passion for building solutions for for people, but increasingly gravitating towards the human side of of that exercise and at that intersection of okay, so yeah, you've got this problem. There's this constraint of money, there's these technologies you might use, there's some cool stuff we could do for you, but you know you're in a hurry. All the, all the things that you know, you know startups know well, and and I was right in the middle of it and really really enjoying that and also really enjoyed not only the human side of the solutions that we built for people but for the people that built the solutions for people. And so I started to move into the much maligned management space of technology people and became a development manager but deeply cared about the people that were involved in the craft and started talking publicly about it, was involved in a number of technical community initiatives, became like this, weirdly became a Microsoft MVP for a technology called Silverlight, which none of your audience will know what it is, I can guarantee it. I actually I shouldn't malign your audience, they're probably very intelligent, but it was a very, very quick technology. That sort of lasted for about five minutes but it was really interesting and I got into that and became an MVP and started to talk at Microsoft conferences. So I built up this community interest in community and public speaking interest in technology leadership and the people who were involved in technology leadership, and then was looking for my next gig.

Speaker 2:

At the time that zero was getting some headlines. I remember walking with my sister in Napier on a visit to her and she was. She was talking about the Craig Winkler's investment and that this place and you know Rod obviously had a connection with the Bay and so she was kind of, yeah, he's really interesting, you should find out what they're up to, you should work for them. And I was like, well, yeah, I've heard of them. I know a few people who worked there. They sound kind of interesting. So I pinged a few people that I knew who worked at zero at the time and sort of just inquired as to what was going on. I met Craig Walker at one of these Microsoft events. He was also a keynote speaker.

Speaker 1:

And Craig. Craig was the sort of the original engineer. Yeah, so he was. He was the muscle who built the stuff.

Speaker 2:

Yeah, so. So I gravitated towards him because he's like this. He'll never listen to this, I'm sure, but he says really and I'm not going to say anything mean about him, I loved him and I loved working with him.

Speaker 1:

I'll make sure he gets to hear this.

Speaker 2:

Yeah, and I and I love the fact that he he might be an interesting person to bring on your podcast actually. Oh yeah, absolutely. And he was just super opinionated, rough around the edges, look beautiful, his hair was amazing, but he had this sort of like honesty and sort of directness to him that I really loved. And we got to know him at this conference. And then there was. It turned out there was nothing really going.

Speaker 2:

I was looking for a dev manager role again, but in a product company. I kind of liked the idea of working in product. It was attractive to me from a guy who's worked for these very mercenary projects where you know, here's some money, build something that's going to take you twice as long for twice as much and we'll complain about not getting enough. You know, there was this sort of agency world's brutal and I was keen to explore something else and I had this. I had this idea that working for a product company would be as kind of the utopia, right, it's like I'm just going to build what the hell I want. If you don't like it, don't buy it, and how easy is that? All my problems that I had in the agency world were gone, like so I thought, and I mean I learned pretty quickly that you get a whole new set of constructions, new set of issues.

Speaker 1:

Yeah.

Speaker 2:

So it wasn't as plain starting but in a sense of working in an area that I enjoyed, but in a different context. It was hugely refreshing and obviously hugely opportune, Eventually joining zero when Andrew Butel who's someone else you might want to talk to was kind of in a similar role to what I was looking for. He was kind of in that product D dev manager kind of thing but also got his hands dirty with coding, so he was one of these multifaceted, really interesting people. But he was deciding to move on and so I came in. Not only did some of the things he did, but sort of the role broadened. And Alistair Grig, who was my manager at the time and the hiring manager, and Alistair was like a COO at this point.

Speaker 1:

Yeah, I think he would have been COO.

Speaker 2:

He was the ying to the yang of Rod and together they were just a really great duo, and so I regularly think of Alistair as one of the best managers I've had. I actually haven't had that many, but not to minimize the praise, but I really learned a lot from him his attitude, his decisiveness when he needed to be, his calmness under pressure, his he cared about people. It wasn't just widgets for him and that really resonated with me and he gave me a lot of space and confidence to grow into what we called at the time a product development manager role. I don't think anyone's ever been called that since, but it was kind of this blend of yeah, you can look after the development team, but we want you to start thinking about the product and, as a whole, want to represent the product, be the voice of the product at conferences, because I was keen to keep public speaking.

Speaker 1:

And this is super early days. This is sort of 2009. Zero was only incorporated in 2006. It listed in 2007. The company is how many people at this point? 50?.

Speaker 2:

It was the size that I personally was the guy who maintained the list of context in a Skype XML file, right, because that's how we IMB each other. When someone joined, I used to give them the file that they could upload onto their desktop version of Skype so that they could talk to the team and we could communicate. It was pretty slack and all those sorts of call-outs that we use now, and we're all on BlackBridge, so it was kind of like this. It was a funny time when I looked back and it doesn't feel that long ago, but it was a different time. A lot of things have changed over those years. Really, how fast this has changed, yeah, and so, yeah, 2009,. There were probably less than 60 people in the team. I was really the first person who was dedicated to product leadership. Sarah Gopel was there looking up some of the internal systems, but in terms of the main core product, I really started to lap up that idea of product leadership over the following few years.

Speaker 1:

And so because product at this point is not even really a science, there's not. There wasn't all the material. I guess around how to lead her at that point in time.

Speaker 2:

No, no, nobody knew what. So product managers didn't really exist Like there was. I'm sure there were some people who had that title, but probably in banks doing something non-digital right, and so in the digital and certainly in the SaaS space, product management wasn't really a thing that was talked about very much little. On product ownership the closest they might have come to it is if you're thinking about Scrum and the product owner role within Scrum, but that's a very different beast to what we now think of as product ownership and product management, and so I was very naive to what it even was in the early days, but I just kept doing my thing right. I just loved being in the intersection. So I love talking to Rod, I love talking to Gary when he was brought on to run the UK and Chris Redd in Australia.

Speaker 2:

I love talking to these people who were way more entrepreneurial than I was, but I gravitated towards them because I love their energy and what they were excited about bringing into the world, and I always used to say and I don't think this is when I think about it now, I think it's a bad description of what product people do but I used to say my job was to put their dreams into reality right, like you know, somehow constrain their ambition in terms of what we actually tackled and then put into play.

Speaker 2:

You know what we could, that was realistic and do it really well, and we had a very good design ethic, with Philip feeling on board. But I've since come to realize that that's the wrong framing for what a product person does. That's what a technologist might do. If you're a, if a founder is working with a CTO, they might be the handbrake and say, well, I can't do all that, but I can do that for you. But a product person is, as I discovered over my early years, at zero it was much more about refining the value of the thing that the founder was passionate about, and not necessarily saying no to it, but in fact never saying no to it, but like really understanding it quite deeply, and that became my sort of mode of operating in those early days.

Speaker 1:

That must have been really challenging, because Rod and I know Rod you know have been in and around that zero world for a while. Rod is, you know, he's quite a force of nature. He is a big personality. He would have had a very strong point of view he wasn't an accountant. Well, actually, I think he might have had some accounting knowledge. How did that? How did that relationship go, I mean, with a guy like that who is right at the front, he's up on stage leading and you're the guy turning that dream into reality? What is that kind of relationship like?

Speaker 2:

For whatever reason, rod stayed out of my way Like I don't know why, maybe Brightened over, yeah, clearly intimidated by my presence, no, but I don't know what it was. But we engaged and I received a lot of input from him in terms of the things he thought were going to happen and be important. Other people in the organization received him and engaged with him differently and had different experiences with him. My, my, the things I remember are him standing up in an all hands and doing one of his state of nation talks. You know, probably would have been I don't know 50 new people since last week's all hands. We were growing incredibly fast.

Speaker 2:

So he would often sort of retell and this is I tell this to my clients as well about how to, how to do, do strategy. Well, you get up in all hands and you talk, like Rod, because he never wrote a strategic paper in his life. I don't think he never. We never had strategic off sites, we never had a poster on the wall that said this is our strategy, but he spoke it and lived it and dreamed it and communicated it to everyone on these all hands. And one of the things he said was he said and and this wasn't all hands. This was not just to the product people and the technology said the most important people in this company are product managers.

Speaker 1:

I would imagine 10 foot 12. I was going here, mate, you're so know how what you're rushing your shoulders at this point, you know but, but he had.

Speaker 2:

but he he was actually, despite being someone who is incredibly opinionated and directed and self motivating, and a starter right. He created a lot of room for product managers to shine and I am very grateful for him for that and he. His other common framing was that he created zero to as a launch pad for people's careers beyond zero. You know you've probably heard him talk about this Like he wanted people to have an experience at zero, give their everything and then go off and do amazing things. How, how well did that work? It was incredible. List off so many people whose careers now would not have been anything without zero and then nothing to do, zero.

Speaker 1:

But now you know, mine he created a rocket ship that gave people a sense of purpose and energy and belief. I mean, you're definitely part of that. I've seen you on stage and, not to take anything away from Rod, rod was a great presenter but you were always the star of of, you know, the of the zero cons, like you really were. You were, you would rock in there with your kind of long curly hair and and get up and do product demos, hoping like hell that the product you know, that you were not going to have Wi-Fi issues and and you absolutely rocked that as a as the product leader for zero.

Speaker 2:

I loved it Thank you for saying that and I really enjoyed it.

Speaker 2:

It was some of the most enjoyable professional moments of my career and and you know it was that enablement and that ability for me to get in front of those accountants at those conferences, understand more about their world as someone who's not an accountant doesn't really understand what they do in the early days Was on a very, very steep learning curve about how all that worked and those conferences were pivotal in creating a deeper sense of empathy for the customers that we were building for, and by the time I left I don't know what it's like now They'd stopped doing that.

Speaker 2:

The product people didn't go to those conferences so much. It may have come back a little bit now, but there was this period in the evolution of zero, for whatever reason that that they became too big, maybe, and there were too many other people who wanted to be on stage talking or I don't actually know the reasons, I haven't really thought deeply about it, but but it was a shift that I'm glad I wasn't there for that shift it was in the, you know, just missed that shift, but you know that enablement and what I was allowed to do at zero, you know, charted the course I'm on now.

Speaker 1:

Yeah, and I'm keen to dig in a little bit to this relationship that exists between a founder and a specialist product leader. I've seen some of the material you've written over the years around this relationship. Tell us a bit about that. How do you see that role working? Well, yeah, what's the right time to start the product leader? Should the founder be the product leader, etc.

Speaker 2:

I love that you're using the word product leader. I'm trying to socialize this as a term. That's not just someone who is the CPO or the executive level product person, which is typically how it's used it's. But I, in this conversation, let's socialize that product leaders anyone on product, whether you're a product owner, product manager, cpo, vp. That's the collective I'm using because there is no other.

Speaker 1:

Okay, well, that's coincidental, because I hadn't seen that.

Speaker 2:

Good, because my take on that is that even a product owner is a leader. It's an oxymoron to not be a leader and be a product owner. So it's pivotal and it's key to the maturity of this practice. But to answer your question in the beginning, when a founder has an idea and they team up with somebody who can help them realize it may be a technical person who's going to be a co-founder and they build a small team around themselves, they absolutely don't need a product owner, a product manager, cpo, vp, a product anyone. Some companies, some rare companies will found with someone in that role. You know Sonia Shazie's trying to think it's just rare. It's rare to have that person in place at the beginning. You may have other examples, but typically they don't and I think for a lot of companies they don't need one because the mode of operating is it's necessarily scrappy, it's necessarily not navel gazing for too long, getting shit done, testing the market, testing their idea even has legs before they invest in deep thinking about it too far. You know they're probably they may well have some domain knowledge of this product, of this idea anyway. So they're bringing Sonia to market that they probably know really well. So they're not looking for a domain expert, because they're at and they go through this period where it's just all on, they're just all in right, they're just trying stuff, right, and that works and should work, and the way of working that that creates is somewhat more linear in some ways. So your CTO is going to be building up a technical capability to keep up with the stream of ideas and the market feedback and is probably not well. I won't say what they're not, but the founder is directing a ship quite heavily in those early days and I think they should be. They should be opinionated and say this is what I think the market is going to love and someone should build as quick as possible and they should test the theory. Then, as the company evolves, as that startup evolves, gets a little bit of success. Some of those mudslinging things stuck and their idea was as good as they thought it was and they're starting to get some customers on board and the CTO has built up a team of technologists around them. They're now starting to go maybe we should hire some testers and they've got some design happening inside and there this arm of the business that's creating the value, that is building value for customers, and the business is getting bigger and has more complexity in it Because now they have some code that's done to Crete, because they're going pretty fast in those early months. So they're now thinking about technical debt, design debt and scrum and all these delivery things. So they've got a lot to think about. Meanwhile the founders hired a sales team and it's got some marketing on board, has started to build an exec team and maybe you're talking to some venture capitalists about the next round, and so they're building up another muscle within the business that is increasingly disconnected from the other half of the business.

Speaker 2:

Who's trying to keep this thing afloat and trying to build it and trying to keep up with the increasing number of ideas that everybody has. Then I get called, then it doesn't work anymore. Why are these guys going so slow? Why can't they keep up with my brilliant ideas anymore? Why can't I just change my mind next week and try something new and they just follow. I don't know why it should take so long.

Speaker 2:

It's probably fair to say that zero in the early days was. I don't know when it shifted, but we had some of those characteristics of it's not working anymore. We can't just hope that we can just keep up with everything. We can't just keep building on the same platform we are. We have critical customer mass now. I remember when we first got our first dissenting customer. Can you imagine? They're all like friends and family for a while and then they're all loving us. There were these early adopters who couldn't. We couldn't put a foot wrong for them, even though we hadn't got half of an accounting ledger built. I remember when the tide turned and people didn't like us. People thought we were doing the wrong things. People thought it was outrageous that we hadn't built multi-factor authentication or I don't know some other purchase orders. They can't run a business without purchase orders. I'm going, I had to look it up. Well, they had other people use purchase orders.

Speaker 2:

What even are they? Yeah, what even are they? So we turned and now it was like not only do we have a voice of customer with demands and ideas and thoughts about this thing you've brought to life, we have a burgeoning sales force, an increasingly opinionated exec who have been hounded by investors to make more money, to get the hockey stick going and it just doesn't gel anymore. No, there's too many decisions and nobody's making the right decisions or feels like they're making the right decisions or in the right position to make the right decisions. So you get this kind of like two halves of an organization not talking very well to each other. And the instinctive solution of a startup founder who finds themselves in this sort of mid teenage years of their evolution is the problem is engineering is not going to, not going fast enough.

Speaker 2:

I'm going to hire one of those. What are they called? Product donors? They do that, don't they? They, they have a whip and they know how to crack it. And they, they know how to do scrum and work with engineers and make them focus and do all the good things. So they hire somebody in their first product role, maybe straight out of university, maybe they're a BA in the past life, or maybe they pull them out of the support team and think they'll do their smart and what they're actually asking that product person to do is they don't ask this, but what they're actually Wanting to happen is to have the two halves of that organization start talking the same language.

Speaker 2:

For the engineering part of the organization to understand what value is for the business and how value is seen by a founder in terms of the runway they have left, the monetization of the product, yeah, what the cash flow looks like when the next round of funding is going to come through and what that mean. What sort of a product do we need to attract investment? What potential do we need to show? There's a very different set of lens and someone who's writing lines of code and for loops and trying to Trying to keep this thing afloat, that's they feel really not proud of anymore, because it's not, it's not elegantly built anymore and it's creaking. There's two very different worlds that are trying to work together to a common purpose, and so that product owner they hired Strativ University or as a BA has no idea about what that intersection of business looks like.

Speaker 2:

They will almost invariably head to delivery land and start doing project gancharts and roadblocks of features and dates and promises they'll never keep and they will. They'll find it very hard, and so the decision that a founder needs to make is to be honest with themselves about what problem are they solving, for Is it is it? Is it a speed issue? Does their CTO agree and say, yeah, we're really slow, and if only we had, if only we were smarter and did things better and had someone cracking it would definitely go faster than no CTO has ever said that? So, but they need. But there could be reasons why they're going slower that the CTO and founder could not out. But but my guess is that that's probably not the problem.

Speaker 2:

The problem is often there's too many things to do and we don't know which one is the best bang for buck, and even when we do it, we don't know if it was worth doing and whether we got any value from it. And they get on the sort of treadmill of building things out. So the question a founder needs to ask is what problem they're solving. If the problem is, how do we effectively prioritize and maximize value for this business? And they don't think they're in the right position anymore to make those tradeoffs between one thing over another. If they still think everything's a great idea and they're all equally good and that's, and we just need to go faster, then they might not be ready for a product person. But if they recognize that this game at a certain level, is that you can't try everything with the mud slinging approach that worked in the beginning. You've got some big rock decisions, many of them that could take very different paths for your business, and you may need an ally to help you decide which rock to chase. And is that?

Speaker 1:

a senior person.

Speaker 2:

Yeah, and that necessarily needs to be a fairly senior product person who can help them on that journey to understand where the value lies and what the upside of that decision might be. It's not a product owner, it's not a junior product manager, it's not somebody's come from an IC role because they've never had to make a senior leadership. What's IC? Sorry, it's unusual for an IC who may be a genius in their field to be able to transition immediately into a senior product role. It happens, but it's chalk and cheese, right. One's about influence, leadership, hearts and minds.

Speaker 1:

One's about you being a genius, yeah, and knowing the product and that product role, just even in the nature and the way that you talked about these sort of disparate parts of the business kind of competing in their objectives, it's a confluence role, right, like it actually has. And I don't mean confluence the technology, I mean the actual, you know the verb. It is a place where everything's kind of coming together. It feels like, you know, outside the founder potentially, or the founders, it's the most important role in the company, isn't it?

Speaker 2:

Yeah, and not. Another word that gets used for this role is you're the gatekeeper. Right, you're the gatekeeper. So not all of those crazy ideas from that crazy founder get through to the team so we don't disillusion them. It's not that at all, because all those good ideas are intel into where the opportunities may lie. Founders are generally super tuned into their customers and what the customers need. But you know, the job is to work with founders and ideas and to refine the thinking and to really understand the potential of those ideas.

Speaker 2:

And then you know, my working definition for anyone in product, whether you're a product owner or a CPO, is that your job is to maximize the ROI of the efforts of the teams you work with, typically product teams of engineers. So you're maximizing the ROI of their efforts towards the strategic goals of the company, right, and that's not about facilitation, it's not about scrum, it's not about delivery, it's not about speed, it's not what might be about speed to market, but it's not the things that often people typically associate with product management. They often think it's about doing a really good specification and decomposing it so that we can build it in sprints. They're required and necessary, but they're not the essence of the value of a product leader, and so the kicker, though, is to know what you're maximizing for and if you're maximizing the ROI of those people who are going to be building this amazing stuff with amazing experiences for customers that solve problems that the business have decided are strategically important. You need to know how to translate the value of the effort of those people into something that makes sense to a founder or a board or a venture capitalist and they're different languages, because a team will often talk about NPS.

Speaker 2:

They might talk about, you know, they might interview customers and ask them how they're feeling about the products. They're very often very and not and this is not to say it's not important, but they're very customer centric. They think about the what's good for a customer, and they may over index on a particular customer If they're two in that camp. They may listen to every customer go oh, we have to solve their problem, and it's very hard for them to think about the other two critical aspects of this decision matrix that you're making, which is, well you know, what technology constraints do we have to be able to address that problem of somebody, and how long is it going to take us to build it, and what's the opportunity cost of doing it? And then, well, what does the business need us to achieve? What are their goals? Are they, are they chasing, you know?

Speaker 2:

revenue revenue, retention, acquisition? Are they just going to throw heaps of money at increasing the funnel? Yeah, what's the goal here in solving current customer problems may not be the right thing to do right now and that's very hard for someone who loves customers and thinks about customers. And so I got challenged with my definition recently. You know this maximise the ROI of the efforts of those teams towards the strategic success of the company. I said where's the customer in that definition? There aren't product people. All about the customer, Isn't it about customer interviews and learning about customers?

Speaker 2:

And yes, of course, making your customers and solving your customers problems is a great thing to do, is a necessary thing to do, and it's at the heart of a lot of what we do in product is thinking about those customer problems and solving them in innovative ways. But none of that matters if it doesn't meet the needs of the company that you're working for, Because there's any number of things that customers would love and you could make an amazing experience for them and would solve a real problem that they had. But if it doesn't result in increased revenue or increased retention or a more acquireable product or entering a new market, it's for nothing. So it's not in there deliberately because you have to make a decision about which customer problems help this journey. But your ultimate measure of success is not making customers happy. It's making the business shine, which generally is because customers are happy. But the ultimate measure of success is business success.

Speaker 1:

It's super interesting because in my head I've got this kind of conflict going on of what the ideal product person, product leader let's call them senior product leader what they look like. Are they a Steve Jobs type character that cares about the bevelling on the side of the iPhone and the less buttons the better? That obsessiveness about the actual product, in his case a physical product? Or is it this incredibly skilled humanitarian, somebody who understands people and is almost on traffic duties on the Champs Elyse, allowing multiple points of connection coming in? What is the ideal?

Speaker 2:

product leader look like, yeah, unsatisfyingly. It's a little bit of everything, but I think if I was to look and make some assumptions around the state of product leadership in New Zealand in order to be able to answer that question, I think and we're doing a survey I work within a society called Product Oteodora and we're about to launch a survey across New Zealand to try and understand my theory and our theory a little bit more. People should look out for that. Yeah, there's a number of people entering product who are coming from IC roles, individual contributor roles. They may be working already in technology or SaaS businesses and they see product management and they go. That feels like a good career step for me. I'm a senior engineer. I want to get out of engineering and do something different, or I'm in support or I'm in design or a number of different roles. I'm going to love it when I can quote a stat and say 70%.

Speaker 2:

But there's some percentage of people in product management who have had an individual contributor background and are learning the ropes of leadership and influence and hit a ceiling in that role because they don't have those you call it humanitarian skills. They don't necessarily. They still feel like managers are evil. They've read Dilbert their whole life. That's probably a little bit, but they've got this Dilbert-esque view of management who are idiot, pointy-head people who don't really understand the real work that goes on under the hood, so that some of them have come from that culture and that is pervasive. And so when they're asked to present an idea that they have to the founder and senior leaders, it's incredibly intimidating and many of them don't really want to do it and working out how to influence people without just being the gatekeeper or having a really good process or being really good at the analytics they're having to learn it. So we have a, I think, work to do to help people with some of more background and maybe adjacent fields get into product who may be dabbled in leadership and being managers or know how to deal with the executives or have been an executive but now really want to help join the dots and to bring their experience into the product world and the engineering world to help them build their business acumen and to help that executive maybe learn about the realities of building software.

Speaker 2:

It's not as easy as it looks like when you look at it from the outside and haven't not done it before, and it's also this is funny. I'm technologist, right. I know exactly how hard it is to build all this stuff. I still think it's easy. I still trivialize what the engineers are doing. All right, it can't be that. It can't take you three months to do it.

Speaker 1:

Yeah, come on guys. Yeah, it must be here somewhere.

Speaker 2:

I don't know what's going on, so I do it and I should know better. And so people who have never been in that do it in space. So there's definitely this misunderstanding between these worlds and so. But we need to do better than just building product muscle with people who have come from the the technology side of the business, the creative side of the business, where I'm on a bit of a mission to cross pollinate more so that we learn from each other Some of the business concepts and ideas and startup ideas. And while I joked at the beginning that I'm not a startup guy, I am super interested in it because I listened to the pitch.

Speaker 2:

It's a podcast about people pitching their ideas to a sharks tank type thing, and I'm listening to it because I'm fascinated by how people present an idea to someone who's never heard of their idea before and the structure of that narrative that they bring to the investors. Because it's exactly what we do in product. When I'm trying to influence the hearts and minds of someone, not to give me money, necessarily, but to buy into this vision and to get excited about this vision I have for it. That might just be a feature, it might be a change of workflow. It could be very banal, but I still have to, in many cases, get people on board with this idea, and there's this structure of argument that I use. I think about it when I'm talking to senior people about how they structure their strategy, right through to less senior people in product who are trying to work with their team, who aren't on board and think that we should be spending all day on tech debt. It's very similar, and so the more I've been in this game of product leadership and where they fit in this puzzle of creating value for businesses, the more I realize that the product side are learning about what you all know intrinsically about how businesses operate and the realities of getting a business launched and bringing customers in and selling it and marketing it.

Speaker 2:

All these things that are bread and butter for you and your background are not bread and butter for most people and product. They're learning it, and I've been on that journey over the last 10, 15 years learning it, not doing it, but being around it and talking to lots of people like yourself, and I'm trying to bring that thinking and that acumen into the product world and I'm trying to educate well, that's a patronizing word. I'm trying to also bring in the sense of realism and opportunity for founders and entrepreneurial types and executives to help them understand this world of product. That is not intrinsically common sense. You just feel like we should just be able to make it and do it, and fast, and go, go, go. It's not obvious that you need to actually sit and do a little bit more rigor than that when you get a bit more mature and have some more thought around the decisions that you make and implement it to customers.

Speaker 2:

So yeah this blending of these worlds is really interesting.

Speaker 1:

It's super fascinating because it is. It's a very cool career, right Like for people who want to shape something and as humans, we've got a natural desire to create. So for people who want to be creators, what a cool role because you're not only creating but you're actually also influencing. Your listening to multiple stakeholders that's a super cool role. So for founders out there that are listening, at what point in their journey, ideally, do they get their senior product leader on board if they're not a founder?

Speaker 2:

Yes, so I started answering that question for you. So it's when things aren't they know things aren't working. Every founder gets to a point where they go. It's just feeling hard. I don't feel like we're moving fast.

Speaker 2:

It'll often feel like a velocity problem, the CTO doesn't have any answers, they maybe can't afford to hire another five engineers, and it just feels like there's this impasse and maybe the founders finding that they can't dedicate the time they used to be able to, with the team being that sort of storyteller of how exciting this opportunity is for us, and so the team are kind of they're not really talking to the team anymore who are building this stuff.

Speaker 2:

So there's this moment and I used to say, yeah, get a CPO on there as fast as you can. I've changed my mind a little bit. I think you should hold on to that scrappiness for as long as you possibly can. If you and the CTO can solve it between yourselves and agree whether it's a prioritization problem or a velocity problem, do it. Don't bring another person in if you don't need, if you think you can sort it out amongst yourselves. But if you've been thinking about it in senior leadership and there's still some friction there, that's not feeling right. That's probably the right indicator that you need to bring in someone, like a product person, to help broker some of this indecision or this. You know what feels like slowing down.

Speaker 1:

Why the change of methodology there for you? Because I remember you talking about needing somebody who was senior and early.

Speaker 2:

Because I've helped a number of people hire their first Chief Product Officer and it was too soon. It's too big a bringing in a C level product leader. It's too confronting for a founder. It's too hard. It's really hard to. If you do it too early, it's really hard to. What do I let go of?

Speaker 2:

You know, my question to the founder is what are you going to stop doing when you bring on the CPO? And I haven't had many of them that can tell me what they're going to stop doing. They're just going to say, no, I'm going to keep doing what I do, but they're going to make things go faster. They're going to talk to the engineers, they're going to build great specs. They're going to listen to me and channel me. They don't see it as I'm going to stop doing something. But unless you're ready to stop doing something, the CPO is not going to last very long. It's going to expensive hire that is going to feel disempowered. And so what I want to hear them say is and this is when they might be ready for the CPO I don't know. I don't have all the answers anymore.

Speaker 2:

I used to be full of all the ideas. I knew what we had to do when we had to do it and what was the most important thing? It was easy for me, I just knew. Now I don't quite know. I've got lots of ideas. I don't know enough about what our opportunity landscape looks like for me to be super confident that I know what to do.

Speaker 2:

Then you need a CPO because they're going to do some enough research. They're going to feed off your insights and your knowledge and your domain knowledge. So instead of jumping into earlier that CPO and maybe making expensive mistake that you have to back out of, I think you could get away with a senior product manager who aspires to be one of them and helps you. And this sounds a little bit cruel because that hire is probably not going to last long. Whether it's a CPO or a senior PM, they're probably not going to last long.

Speaker 2:

In this product community we joke about the sacrificial lamb being the first product hire running an organo, because it's brutal. Nobody knows what you do. You're never going to satisfy anyone. You're certainly not going to make things go faster. You're probably going to make things go slower because you're going on about customer research every day and everyone's going to blame you for it going wrong and you'll hate it. People won't enjoy working with you and you'll be gone, so in some ways you want to get that out of your system as early as possible, maybe.

Speaker 2:

And so I think if you had a senior product manager who didn't totally fuck it up but challenged your thinking enough for you to really start to see the value, because they've really got to be a champion for the value of product. So they've got to live my mantra of maximizing ROI the efforts of the teams they work with towards strategic success by absolutely knowing what strategic success looks like. And if you're part of the 70% of businesses who can't articulate what strategic success looks like that I work with at least, they find it very hard to articulate a strategic direction and what success looks like beyond having more revenue, more customers, and so that's their first job is to get under the hood of what's really driving this business and what decisions are we making and not making that are our bets for success in the near term and say the 12 month term, about as long as their career will last in that business, and so that's their job. The job is not to administer a backlog. That's a different career. That's a project manager. Get a project manager to do that, get an IC to do that.

Speaker 2:

But if you really want to maximize the ROI of the efforts of the people that you're spending hundreds of thousands of dollars a month on then get someone who's going to really help you do that maximization and whether you call them a CPO or they're a senior PM with aspirations to be more, but they need to be comfortable operating at that senior leadership level of a business.

Speaker 2:

They need to be comfortable asking dumb questions to founders who obviously why we're doing X, not B, not Y, and really use that intel about what's valuable for the company to be their maximization equation for what they're going to do with the team and how to defend the decisions they're going to make with the team that the founder will disagree with. They're saying I'm doing this now and the other thing later because this is going to have a better impact on our customers, going to change their behavior, it's going to attract a new type of audience and it's going to contribute to that strategic goal we had of going to the enterprise or whatever. It is the thing that everyone's trying to run for and that's a hard job. It's not a junior job. It takes someone who's had some battle scars who knows why that isn't obvious for the founder to have come up with themselves and empathize with that and also empathize with a team that's probably feeling hounded by an exec that keeps telling them they're not going fast enough.

Speaker 1:

Does the best product leader come with domain expertise, or is it ideal for them to not have that?

Speaker 2:

No, no, and I used to say that it's a bonus. If they had that, that's even better. But I'm not even sure that's true. Lots of people will tell me oh, my business is really complicated. No, I've got to bring in somebody who knows what they're doing, otherwise how are they going to know what to tell the team to build? Well, because the job's not to tell the team what to build. That's the first answer to that question. And most senior product people are very adept at quickly lapping up a new domain. No, there was no accountants building zero. Right, craig was not, he was had. You know, was famously had his Accounting for Dummies book on his desk yeah.

Speaker 2:

And so I think you're better off hiring for leadership experience first, product leadership experience second, and then in air quotes. How do they balance the diversity in your company? How do they augment what you already have? Are they just going to perpetuate this things you're already doing or are they going to bring something new and exciting and different? We have think about that and then maybe think about well, do they know anything about I don't know laying infrastructure in the streets of Wellington? But don't start with. I know all about infrastructure projects.

Speaker 2:

Therefore, I'd be a Chief Product Officer for you, and this is a great segue, because one of the things you might have seen me posting recently was the fact that 60% of executive product leaders in New Zealand have never held a product management role. Yes, they've never held a dedicated product role before. So they are, and I'm doing some further research to qualify this out. They are far more likely than your. They're far more likely to be a domain expert and an internal hire. So they maybe they created, they became a domain expert by having been in the company for eight years, and so then they got signed the CPO role, and the challenge is that if your first product hire is an internal domain expert. They're probably not experienced in bringing these two halves of a company that have started to refer to each other as too slow and the business. They're probably not going to work out how to bring that together and create a more aligned view of where that value should be sought after. And so they struggle with, I think, product culture and alignment of effort towards common goals. But they have great relationships at senior level. They understand senior level business. They may have been founders and execs. They great orators often. They know how to talk to a room and hold a room and tell a story. They've got lots of amazing qualities, despite the fact that they're not really sure what this product leadership thing is.

Speaker 2:

But the CPO sounded like a good acronym and so that's why I'm focusing on that CPO group, because there's all those people. Half of them are those people and then the other half have managed somehow to come through the PM ranks and be successful at the executive level, which is miraculous, really, when you think about how different the job is and mixing them all up. How cool is that if they can all learn from each other's experiences and knowledge to create these better places. So, yeah, no, they don't need to be the main expert and it may not even help because it may just sway you in terms of you may be too opinionated and too in your lane to be able to see the innovative move that is staring you in the face.

Speaker 2:

If you come in there fresh and you're like would an accountant have made Bankrec the way Philip did it? I don't know, that's something that takes some different set of skills. He quickly understood the problem right. Yeah, philip being a designer, philip Keelinger being the head of design, one of the founders was zero. That's one of his money shots was building that Bankrec. But I don't think an accountant would have come up with that. And so, yeah, domain experience can get in the way. It shouldn't be a heavy criteria in your recruitment strategy.

Speaker 1:

Tokes, this has been an absolute masterclass for people listening to you and understanding more about the role of product leadership and the interplay between the product leader and the founder. Product is quite a. It's a global set of skills. It's a global role. There are people that are going to be listening to this that are not even living in New Zealand. Obviously, lots of people that are living in New Zealand, but people living in Australia are offshore. It's kind of interesting actually just looking at who's listening to this around the world. I will make it super easy for people to connect with you and I'll put that into the show notes so that they can. Any final message or word of encouragement for people thinking of a career in product or those that are already in product? Any sort of thoughts?

Speaker 2:

you want to leave them with.

Speaker 2:

I do, because your audience is probably going to be less product people and more entrepreneurs and founders in the early stage. I want them to become product people, so I want your audience to go. I don't know if you want to mortgage my home and be a founder again. I actually want to work for a company that still feels like a startup, but it's got some massive potential. I want to be their chief product officer, and they should come along to my meetups that I run every month for product professionals. I've just launched a new thing that I don't have a name for, but it's going to be a program for executive product leaders to connect with each other, because they're notoriously disconnected, and a lot of them are doing it, like I said, without any product pedigree, and so I'm trying to learning on the job, and so my goal of bringing them together is to create this program where we meet up and talk, shop and learn from each other and build some assets together, and so I'm running for the next two months it's still two months to go Every two weeks, cpos can drop in and meet their peers and we can talk cool stuff around various topics that are very relevant to their worlds, and I'm noticing I don't know if you've seen this trend.

Speaker 2:

I'm seeing people going from CEO to CPO. I saw another one yesterday from ProjectWorks and it was super spooky because they were a company that was mentioned to me literally the same day. I'd literally talked to Darrell Gray, another zero alumni, who was talking about this sort of move from CEO to CPO. We were talking about Rod kind of did it, vaughan did it, you know, and so, yeah, so those people who are new CPOs, who maybe were a CEO or founder, I really want them in this community because their stories and experiences are gold, Gold, and if they're feeling at all uneasy about taking on this new role that they're learning about, come along and share some ideas with some other CPOs.

Speaker 1:

I love it and for CEOs out there who don't want to forever raise capital and actually just be in the cool shit and building the product, it's a good chance to change your job and go from CEO to CPO. Yeah.

Speaker 2:

I mean there's still a lag of satisfaction going on there, but you're probably used to it being a CEO. But the results of what you do you can sometimes take a wilder bare fruit, which, ironically, my final stat that I'll throw out there is the average tenure of a CPO is 1.96 years in New Zealand, and so it's a tough gig that many don't survive beyond a couple of years, and so it's not for the faint-hearted. But I think there's some resilience in that CEO founder community that would make a big difference in these roles.

Speaker 1:

Well, those are real words of wisdom and quite encouraging for anybody considering this as a career or those who are already well part of it. Andrew Tocley, TOECS to your mates, actually to the broader product community.

Speaker 2:

Even people are my mates call me TOECS.

Speaker 1:

So yeah you go. We can find you on LinkedIn. As I say, I'll put connections to you in the show notes to the podcast TOECS. Thank you, mate, really appreciate your time.

Speaker 2:

I enjoyed the floor to talk about stuff that I enjoy, so good luck with the future guests group. Fantastic.

Speaker 1:

Thanks guys.

The Evolution of Product Leadership
Evolution of a Product Manager
Founder and Product Leader Relationship
The Role of Product Leaders
Hiring the Right Product Leader
Product Leadership Insights and Advice
Product Community Chat With TOECS