Toby Delamore

Episode 28
Brave UX

Unlocking the Potential of Product People

In this episode of Brave UX, Toby Delamore speaks about the importance of coaching, mentoring and peer learning for product professionals, and shares ideas on enhancing collaboration.

Highlights include:

What is COLAB and what problem is it seeking to solve?
Why is it important for team members to be aligned on outcomes?
How can you get a difficult stakeholder onboard with your ideas?
What has your experience as a mentor taught you about yourself?
What does good cross-functional collaboration look like?

June 22, 202101:00:16

Listen on:

Who is Toby Delamore?

Toby is the Co-Founder of COLAB, a global community of hand-picked product professionals, who are committed to life-long learning.

Toby is also a GM of Product at Xero, where he provides product leadership to a cross-functional team of over 20 talented people, as part of a global small business accounting product that is used by over 2 million people.

Before joining Xero, Toby was a Product Manager at Roam Digital, one of New Zealand’s largest and leading full-service digital consultancies. He also invested several years at Trade Me, New Zealand’s equivalent of eBay.

Transcript

Brendan Jarvis:
Hello, and welcome to another episode of Brave UX. I'm Brendan Jarvis, managing founder of The Space InBetween, and it's my job to help you to put the pieces of the product puzzle together. I do that by unpacking the stories, learnings, and expert advice of world class design, UX, and product management professionals. My guest today is Toby Delmore. Toby is the co-founder of COLAB, a global community of handpicked product professionals who are committed to lifetime learning through COLAB members join a micro community where they help each other to level up, participating in safe, open, and honest conversations by day. Toby is a product manager at Xero, where he provides product leadership to a cross-functional team of over 20 talented people all working to deliver beautiful software as part of a global product that is used by over 2 million people. Before joining Xero, Toby was a product manager at Roam Digital, one of New Zealand's largest and leading full service digital consultancies where he led product discovery, validation, and execution for startups and established businesses alike. Toby also invested several years at trademe, new Zealand's equivalent of eBay, where he evolved and established new products and product strategy, including launching a data platform that created new value for both the business and customers passionate about helping others to level up. Toby is also a mentor at Plato, a mentoring organization set up by alumni of Y Combinator, Paul Graham's world famous seed fund and startup accelerator. And on this wintery day, Toby's joining me on Brave UX to talk about product management strategy and collaboration. Toby, welcome to the show.
Toby Delamore:
Thanks, Brendan. Looking forward to this conversation.
Brendan Jarvis:
Well, don't say that just yet. You don't know what my first question's gonna
Toby Delamore:
Be. No, that's right. It could all go downhill, but I'm excited. I think there'll be some really good stuff to talk about with you.
Brendan Jarvis:
Indeed. Now, Toby, tell me, is it true that you like to run around fields wearing body armor while carrying a small ball inside a small basket that's attached to a big stick?
Toby Delamore:
That is true, and it has been described in many ways. One of my best friends was nice enough to call it quidditch but a lot of people passionate about the sport of lacrosse, and I'm one of them, and I've been lucky enough to play it around the world, which has always been a great adventure and something I've really enjoyed to do since high school.
Brendan Jarvis:
I understand your first job was actually working for the New York Lizards, which is a professional lacrosse team. What was that experience like?
Toby Delamore:
Yeah, I took it on as sort of a summer job, and that was really interesting. I think in America, sport and sport management is so big, you know, think of the big four in terms of places like the NFL and mlb, they're huge organizations. So even to be part of a professional sporting organization, the New York Lizards was really interesting. Probably the first taste I got of business and running a business because it wasn't like we just went to the sports field and threw a ball round with that stick with a net. We actually were part of marketing it, part of ticket sales and learning how to build that business up because professional lacrosse was growing at that time. And so it was an exciting time to be part of that. And probably a role like credit was getting me interested in business and working to build up a business.
Brendan Jarvis:
And I understand since coming back to New Zealand, and now you're obviously at Xero, and as I mentioned in your introduction, you've worked at Roam Digital and also trade me prior to that, but you've maintained your connection to lacrosse. I believe you're actually the chair of New Zealand lacrosse. What is it about the sport and wanting to be involved in the leadership so much that has captured so much of your attention and energy?
Toby Delamore:
Yeah, I think it's enjoyment in leadership that you can help influence change. And so when you're passionate about something and I'm passionate about lacrosse, if I can step into a role and use my skills and expertise and provide value towards change that's positive then I think that's something everyone should do if you get that opportunity, especially for community elements. So lacrosse is a grassroots sport and the, there's no paid roles there. It's people who work hard on the ground to really build the sport so that others can come in and enjoy it. And we're seeing great growth in high schools across New Zealand, and that's what makes me kind of excited about taking on those roles is if I can build that out, other people get the opportunity to do what I did, which is jump into a sport in a high school, take you around the world, play in America, play overseas. So yeah, it's that passion to use leadership to drive change, which then goes on to create both value and enjoyment for other people. So yeah, I enjoy those roles
Brendan Jarvis:
And something else that helps drive changes coaching. And I understand you've done that both in sports and also in the professional realm. It's something that you've pursued quite a lot in recent times. I mentioned in your introduction, Plato, which was a mentoring organization set up by some Y Combinator alumni. What is Playto and what is it trying to achieve
Toby Delamore:
And coaching, mentoring, they have a slight difference, but I think ultimately it's the same goal, which is helping grow people. And Plato I found is a really nice platform that's sort of taking mentorship, which I think especially in New Zealand can be a little bit ad hoc and unstructured. Not that it needs to be really structured, but more than just catching up randomly and no real preparational outcome planned. And so what I really liked about Plato is they built this platform that helps articulate your skills and your background either as a mentor or a mentee, and then start to connect people who have those common focuses. So in terms of what I can do with Plato is sort of put for what I have done in my past, what my experiences, the areas I work in, even if it's just things like a SAS business, and then mentees on that platform can find me and say, well, I'm working on a SAS product as a new product manager, and so I want to have that experience to lean into and ask questions about.
And so what I think Plato's done really well is build that platform to provide the connections. And then something else I'm passionate about, which is the conversations between product people, that's the bit that myself and other mentors bring to the table is the unique conversations we can have with those mentees. But Plato's given that platform to allow it to happen and allow those connections to happen. So yeah, it's a fantastic platform. I really rate what they're doing and they're excited to see where they can grow that of next level of mentoring and coaching beyond the sort of casual, just catch up
Brendan Jarvis:
[affirmative]. Yeah, I understand. And now when it come to COLAB, of course soon, but I want to ask you about your participation as a mentor. What has that taught you about yourself?
Toby Delamore:
Yeah, I think the first thing that it teaches you is you don't have all the answers. If you go into mentoring because you think you know everything and you're just gonna tell people how to do it, that's never gonna work out well. So what it's taught me is, yeah, I don't have all the answers, but if I can help someone to think about something or steer them in a direction or ask them the right question to make them think I can help people realize that actually they know a lot more than they think or they have skills that they haven't trusted as much until someone really challenges them to do that. So it's sort of built on my experience in sport with coaching, with leadership to sort of understand that your role as a mentor is to come and help people reflect on themselves and what they're doing so they can look to understand and put forward their own next step and not just have you tell them what to do as a manager or someone might do.
So, yeah, it's really taught me that skill made me reflect on how I do that, making sure that you don't, and again, this is something that I think when you're young, you get caught up in, which is just tell people what to do. I know what to do or I think I know what to do, so I'm gonna tell you. And mentoring has given me that reflection that actually it's not about telling people what to do, it's about empowering them and helping them get the best out of themselves. So that's something I've really enjoyed having gone through some mentoring now, both having mentors who have taught me a lot, but also doing mentoring teaches you as you get into it and work with different people,
Brendan Jarvis:
Sometimes you just have to sit in your hands and ask questions.
Toby Delamore:
Yeah, you do. And it's hard. And I've got a couple of great mentees here at Xero and sitting with one recently and she was asking, well, how could I do this? And it is very hard to hold back that impulse to say, right, well, here's what I think you should do A, B, and then C, because that's the way I would do it. And so the challenge is always that element of holding back your own opinions and thoughts to the therefore go and just ask that question that gets them to think and almost think aloud through what it could be and give that little nudge when it's needed. So yeah, it's definitely hard.
Brendan Jarvis:
I had a conversation with a fellow Kiwi Robbie Allan, who was in product until recently at Intercom, and we were talking around not specifically mentoring, but about I suppose the vigor when you're younger in your career that you have and the passion that you have for being right, and how often it's not always about being the one to be seen to be right. It's gotta sit in your hands and you've gotta be a bit more patient with people and come to help them to come to their own conclusion. But anyway, this is about you. I wanna talk about COLAB. It's something that I'm quite interested in and I'm sure that our audience will be as well. We were introduced by Lucas Colo, who's the VP of Designer Roam. Now I understand that you, Lucas and a few others have been up to something lately, and as I mentioned it's called COLAB. What is COLAB and what is the problem that it's seeking to solve?
Toby Delamore:
Yeah, yeah, we've had a fantastic team that's been building COLAB, and COLAB is something that we've been experimenting with. We started very lean, just simply putting something out into the community to see what people thought. And it was really focused on what can we offer that sort of empowers growing product professionals through collaboration. And we are looking to solve this problem that I've actually actually had in my experience and Lucas and my other co-founder Adam had, which is in product, it's really hard to find that time to sit down with your peers and learn from them and talk about your experience and get into the real world experience you have in product. There's a lot of content out there about product management that'll tell you the best frameworks tell you the best way to do things but on the ground when you're practicing it, it's hard.
And sometimes it feels like, why can't I do it in that perfect way? Or why doesn't that framework work for me right now? And that's because every product manager and every product person out there has a unique situation they're dealing with. And so for me it was about how can we start to unlock some of this value that each individual product person has and leverage it through collaboration so others can grow from it. So what we have of established with COLAB are these micro communities of product professionals and they've focused on coming together over a six week program to foster growth talk about really key challenges that they choose, and then share their practices and experience around solving those challenges. And then around that we are boiling a community that is part of bringing those cohorts together and then leveraging them to help each other throughout their day to day work.
Brendan Jarvis:
[affirmative], tell me about this idea of a micro community. When you say that, what do you mean and what does that look like in the context of COLAB?
Toby Delamore:
Yeah, so it's a really interesting term because I think it's starting to come to the forefront a bit more. And we've seen kind of usual communities that are big communities, you got great ones like mine, the product, and it's a huge community of product professionals, which is fantastic. But these micro communities are very focused in on the people that are part of them. And to me the slight difference that is quite powerful is the relationships. And so within micro communities, you start to build the relationships with the people in them, and you've sort of seen that maybe with something like a mastermind group or things like that. And by having the smaller community, the relationships build and they become stronger. And with strong relationships comes trust and the sort of vulnerability to share challenges and things that you know might not share in a wider community. And so for me, micro communities are the sort of sub segments of the broader communities we see today but they're focused more on bringing together a smaller group of focused people who want to work together. And I think foster relationships as well as learning
Brendan Jarvis:
[affirmative]. Yeah, it sounds really powerful. And just how big are these micro communities that you're bringing together?
Toby Delamore:
So we've started with cohorts of 12 product professionals, and again, it was of experimental, was 12 the right number? Would 20 be the right number? We can still experiment with that, but we are bringing together market communities of 12 people. We found that works quite well. It's enough that in six weeks you're actually getting to the end of that with some really strong relationships. And that was something that we were quite interested in because when people leave these six week programs, it's not a kind of finished thing. We don't really want to be that program that's just tuning people through. And once you're done, thanks very much, we're looking for the next person. Want those people to come out of this with a network that they go on to use for years afterwards. And we're seeing that where people are going through these programs and because it's 12 people, they are building that relationship where afterwards they're connecting and meeting and reaching out to each other to use each other's expertise to help them. So 12 people in our micro communities in our cohorts which has been a good number, but really interested as we build out COLAB and what we're starting to offer in market cohorts are just one of them. And as we offer more value ads for product professionals and the wider product community, I'm really interested to see if those micro communities might be 20 people or maybe have a really small one of five based on a specific topic or particular focus. So yeah, really interesting world to be playing in
Brendan Jarvis:
[affirmative]. I mentioned in the introduction that the premise of these communities is to have clearly professional conversations about product in a safe and open and honest way. What is collab delivering that a lot of product professionals aren't getting in their day to day in their workplace?
Toby Delamore:
I think it's that time to collaborate. And I think for me, collaboration and product management is a really strong skill and something that brings a lot of value. And so when you're doing product, as many product managers will know it is full noise. You have a lot on, you've got the fires burning, you've got the stakeholders asking things, you've got the team that needs information you've got a strategy to write that you were meant to finish last month, so it's all go. And what I always found was that meant you didn't get the time to just look at what you're doing and learn more from others. And I think what people are getting out of that is that time to just sit down and have that space to have those conversations as well as that ability to just ask someone, I might say, Hey Brendan, how have you tackled this before?
And you can tell me right there, and that's gonna gimme an insight to sort of say, wow, I never thought of it in that way, that's really useful. I'm gonna take that straight back to my work and apply it or great, I'm not crazy, you're doing it the same way. That gives me this sort of sense of relief. And something that was really a powerful to me that one of our members mentioned was that having gone through COLAB, he came out of it saying, I no longer have this imposter syndRoam. I no longer feel like I am sort of alone in this product world. There are other people out there who have the same struggles, who have the same challenges, and that makes me feel confident that I am tackling these things alongside others even though we don't work in the same company, you understand the pain points and things I've gotta go through. So to me that's really powerful, giving people that forum that allows them to have these conversations and talk and just share enough that they start to feel confident in their own roles and what they do.
Brendan Jarvis:
It almost sounds like peer coaching or peer mentoring of sorts.
Toby Delamore:
Yeah, I think there is naturally that. And what's really good is it's not just mentoring because we put a facilitation structure around it and we pick key challenges. So we might one week talk about product strategy and the next talk about how you build great product teams, you're actually having a bit of focus. And that's I think what we're finding the balance with is allow people the space to talk and share their own thoughts and ideas, but provide the framework and a bit of structure that makes it valuable. Otherwise it is just a conversation that could go anywhere and might not be as valuable. So that facilitation really makes it stay on track, have a good focus and drive value into real elements of the product management role.
Brendan Jarvis:
[affirmative], how do you decide who gets picked to become part of a cohort?
Toby Delamore:
Yeah, that's probably the hardest thing that we do. And we were really focused on making sure we could bring together a group and a cohort who could provide value for each other. So we look to bring together the right group of people based on their skills and experience diversity of thought and backgrounds and really a balance of expertise depending on where they've worked or what they do or what we can reflect on them being passionate about. We ask a few questions in the application process which give us insight into what people are looking to get outta COLAB. And so we want to make sure we bring together a group of people that are gonna both connect well but also challenge each other well and bring thought or viewpoints that may not have been part of someone else's own experience.
Brendan Jarvis:
[affirmative], you mentioned diversity, both of thought and of background. What does diversity mean for COLAB and how do you ensure that that diversity is being reflected in the micro communities that you're creating?
Toby Delamore:
Yeah, I think it, it's important to us, it's important to have that diversity of people with different backgrounds and where they've come from and who they are. So I think we try and look at all the applications and select to get that really good balance, whether it is just making sure we have a really good balance of male and female or different backgrounds of where people have grown up and in the countries or ethnicities they come from, we wanna bring those different viewpoints because it's not just, Hey, what company have you worked for that's important in your diversity of thought? It's where did you grow up? What's your life story? And if someone like me, I grew up on Hickey and then went to America and that's given me different thoughts. Lucas, he grew up in Brazil and that's a different life and a different culture and a different diversity that he can bring in terms of his own thoughts and the way he approaches things. So yeah, I think for us diversity is really important and it's something we try and do our best to balance across all spectrums. So yeah, I hope we get it right and it's something that we continue to challenge ourselves on and I hope that we can just continue to have more and more diverse people coming into COLAB that help us build out that platform to be a diverse area of thought
Brendan Jarvis:
[affirmative]. Yeah, and I think that's a really positive thing to be doing. It's also something that I'm consciously aware of on brave UX as well. It was recently highlighted to me that there is a strong bias in my guest towards males and a particular white males. So something that I'm keenly aware of and working on as well. Now thinking about COLAB and the problem that it's trying to solve, what does that say about the predominant culture that your participants, your members, your micro communities, what does it say about the culture that they're working in?
Toby Delamore:
I think for some it shows that there is a challenge within the culture they're working in to really have that product culture. We talk about customer centricity and leading with the customer at the forefront or solving for customer problems. And not every business has that at the forefront of their thinking and that can be a challenge. I think also though it also doesn't point to just problems with culture, it's just such a busy and tough role in product management that it sort points to, and I do this myself naturally, the first thing you do is you cut your own growth and learning out of your time because you have things you need to deal with and your priorities that you have to tackle. And so what I think it sort of shows is that people are looking for growth opportunities, they want to grow in their careers, they want to grow themselves and expand their kind of thought and skill set but it's very hard to do that because you've got work, you've got life, you've got family.
And so I think what we wanna try and empower more of is a space for people come in and do that and provide that quality of growth that is worthwhile putting time into rather than taking a scatter gun of doing multiple courses and hoping some of them stick. I think we're trying to drive that ability to provide good use of time towards growth because time is valuable for product managers and we know that. So to your point, I think there is certainly some business cultures that are growing and still in their infancy in terms of having the right culture towards products and building out that customer-centric culture. And I think for others there's just that personal challenge of putting that time into your own growth and where to go to find that chance to have growth and learning
Brendan Jarvis:
[affirmative]. Well, let's go a little bit deeper into this predominant culture or the reasons for why people might come to COLAB. I was reading on the website the following, as product professionals, we've found that the best way to grow is to learn through shared experiences informally we've learned through friends and colleagues creating our own internal framework of best practices. What was missing was a structure to validate these frameworks and to learn openly without judgment or fear of competition. Now in particular, I wanna focus in on judgment or fear of competition because I think this is something that we may have just danced around a little bit when we were talking about the culture. What is it that you've seen out there between yourselves as founders and through the people that participate in COLAB that reinforces that fearful or competitive culture that's so counter to the product outcomes that we wanna achieve as product professionals
Toby Delamore:
In terms of a competitive business culture?
Brendan Jarvis:
Yeah, I'm just interested in what are those practices or beliefs or cultural norms that product people are having to contend with in their day to day that have made them fearful of having these kind of conversations openly within their own organizations?
Toby Delamore:
Yeah, I think it's definitely that challenge and pushback that you can get in a business where as a product manager you advocate for your customer and you try and put that at the center of what you think about. And isn't to say that is everything there is the balance in product management, your role is about working out the best balance of customer value to deliver business value, but I think in some cultures is that sole focus on revenue or sales. And so it can be challenging for a product manager to be that advocate and take that stand to say, this is what we need to focus on. And you'll get pushback and you'll get, especially if you're a sole product manager or product management is a small discipline within a company that's gonna result in you feeling like you don't get heard. And that's tough when you don't get heard.
And so if you are the minority in the company, I think a lot of people try and talk and the more you get pushed back, the harder it becomes and the less motivated and safe you feel to provide those opinions. And so I think when you come to a space like COLAB, as I said, you have fellow product practitioners who may have those same struggles. They may be a product manager or a startup that's trying to convince the founder around how to think about things. And so you have that ability to help your approach the learning of others and what they've done and how that can work towards that. I think the other thing as well is that it's not just within businesses, but it's something that's not a problem, but a part of a wider community where you don't know everyone or you don't have a relationship with them is that there is judgment.
And I feel it on social platforms and I'll post something on LinkedIn and I'm sure as many people do use this fear of, will people judge me for what I've said? Will they think it's silly or that's, why am I saying that? And so I think there is also that in broader communities, in public forums where you don't want to just say, Hey, I'm really struggling with this, or I actually don't know how to write a product strategy, could someone help me take some bravery to put that out? And I think what we are trying to build as in terms of culture is a space that feels safe to do that and say, I have no idea how to do this, guys, could you help me? And it's been really refreshing to see we have a community for the alumni of our cohorts and the things people put in there are personal challenges and things that you have to be vulnerable to ask for help on.
And I think that building of relationships and trust allows you to feel safe to ask those questions. And so I think there's a slight issue and it's a bigger, broader cultural issue where vulnerability and putting forward that you don't know, something is always judged as therefore you, you're not smart enough or you aren't good enough to be able to do that. Whereas it's just a learning curve. We don't know everything. You're just trying to learn and do your best. And if we could reach out and ask people for help throughout every forum, I think we'd have incredible learning and growth across everyone. Unfortunately we are human and sometimes humans can make mistakes and judge others. So yeah, I think culture is super interesting and I certainly have never realized until we started doing COLAB, how much that is something people are looking for is that safe space and that culture that allows 'em to speak up and be heard
Brendan Jarvis:
[affirmative]. Well, it sounds like what you're doing is gonna be super important and super valuable for the people that participate in it. Toby, just before we move on to a topic that I have in mind, who is this really aimed at? What sort of level of career product professional is this best suited to?
Toby Delamore:
Yeah, I think we've majority are sort your mid-level product people who have had some time and roles and I think gone through enough experience in their career to start understanding what is a challenge for them, what they found difficult. And saying that we've had a whole range of product professionals from product owner roles through to chief product officers but that sort of middle tier product managers people have had two or three years experience in product has been good. It means that each participant can bring their own thoughts and ideas to the table. They understand product a bit, but they're still learning and so others help them learn in that way. So that's sort where we've started, but I think as we grow we are looking to diversify and provide more focused offerings that allow for each stage in the product career to come in and get value.
Brendan Jarvis:
So I believe you're onto your third cohort?
Toby Delamore:
Yes. We currently have our fifth cohort open for applications at the moment. Fifth. Yeah. Excellent. So yeah,
Brendan Jarvis:
It seemed like you were opening up different tracks as well. I saw that there was a leadership track and also there was a design product design track. Is that a fair reflection of what's going on?
Toby Delamore:
Yeah, those are two areas we're interested in starting to gauge people's interest. I think we've gone through this early growth of just testing that this could add value and be something that people enjoy and get growth out of. And that's sort of been validated. So now as we go into our fifth cohort, we're starting to look at, as I said, some of that diversifying of what could be offered. So design leadership are things we're interested in. So if anyone is in that particular type of role and interested in what we've been talking about, then we'd love to hear from them because we sort of crowdsource the inputs to help us determine what we can build to add value versus just building something with the expectation people will have value for it. Looking forward to seeing if we can kick those off.
Brendan Jarvis:
And for everyone that's listening, we'll be linking to COLAB in the show notes so you can find out more about those new cohorts and all that's going on at COLAB there. Now you mentioned Toby, that something that you were interested in and had a passion for was enabling collaboration. You've said in the past, and I'm gonna quote you now through my time in products, I've learn that creating successful products is hard. Why is creating products hard?
Toby Delamore:
Creating product is hard and creating product is hard because it is made up of so many factors that need to come together to make it successful. And even when you think you've got them all right, there's a factor out there that you haven't considered or just happens to come in, that makes it hard to make it successful. So product is hard and it's also a team sport and that makes it harder because it means you can't just go and do it. You bring together different strengths and skill sets to enable a product to be successful and that can be hard to do. Humans are complicated both in terms of the teams that build product as well as customers. And so you need to understand both that customer side where you need to understand what your customers are, what's their motivations, what the value they're looking for from your product, and you want to understand what you need inside a business to create something for them to solve that problem.
And I think that's something that people miss sometimes with product management is looking at that broader team within your business and sort of saying, well, how do we bring this collaboration together to ensure that our products are successful? And that's not just at a product team level, we've got the classic product management trifecta of design, engineering and product, whichever one will know well. But really I think as you step into product management and product leadership, you need to be thinking about marketing and sales and customer support. All those elements are also teams that need to collaborate with you to ensure product success. So yeah, product is hard. It's hard because it's a team sport. It's hard because there are elements in there that are so intangible that you need to understand and take into account and you have to roll with it. It's a fluid ever evolving, iterative process so you don't get a cookie cutter for product success to just stamp out successful products. Everything is different every time, but that's what makes it fun.
Brendan Jarvis:
Well, I've certainly found collaboration, particularly in the early stages of my career, was difficult being an only child, I've had some hurdles to overcome [laugh], but I feel like I've rounded off a few sharp edges over the years.
Toby Delamore:
Yeah.
Brendan Jarvis:
Tell me, Toby, take me to a time where you remember collaboration and the context of product management really working well,
Toby Delamore:
It's sort about taking, and this is something that I've learned, and Marty Kagan who you had on the show actually, he sums it up really well, which is collaboration is not about consensus which I think is important to note. It's not about just making friends with everyone and feeling like everyone is your friend and hey, we all agree this is an awesome idea, [laugh]. And so for me, I think collaboration is when we were looking at Roam, we were working with our good nature of Wellington company that build rat traps, self rat traps quite a cool product. And we had to figure out how we're gonna bring this rat trap to be a digital connected product. And that takes a lot of collaboration between the Roam team, the good nature team between the team at Roam and what we were doing. And that collaboration came in challenge and conversations, but ultimately understanding the outcome we wanted to get to.
And I think what we did really well in that space is we defined that early and we had agreement, this is where, this is the outcome we want we dunno how we can get there, but we agree on that outcome both as good nature and Roam and together and as a team and working through it, it was really successful collaboration in the sense that we had that common purpose, but expertise who worked with autonomy in terms of design or engineering and that type of collaboration is I think when you start to know you've got a good team that can collaborate because they know their expertise, but they loosely hold on to what they've created or their belief in it and they can take on board feedback and sort help shape that final outcome. And it was really good. That was a time where I sort of saw a team work well together, solve problems, solve challenges, you're dealing with Bluetooth technology, there's a lot of challenges that come through and ultimately come out the end of it with a really great product that worked really well.
Brendan Jarvis:
So tell me, you've just described what good collaboration looks like. You've talked about the ability for people to be able to challenge one another, but holding their own opinions or perspectives loosely. What is an example or what are some of the things that people should avoid or look out for when they're trying to set up and frame an effective collaboration on product?
Toby Delamore:
It's a good question. I think it's avoiding that thought, that collaboration is just feedback and acceptance. [affirmative] not starting out with this concept that what you're trying to do in terms of getting collaboration is just get people to agree with what you're putting down [affirmative]. It is about understanding and helping others understand that collectively everyone is gonna play a part in building the success. So if you're a product manager out there, it's making sure you understand that you are not the shining light or the night armor leading the charge. You know are really that person that works to bring others in, empower them, lift them up and get them to share their expertise because any good team is built up of experts in their own right of something but they need other people's viewpoints and perspectives to help balance it all collectively. So yeah, avoid that mistake of thinking you've got the answers or you are the product manager, so therefore you need to come up with the ideas and instead focus on understanding your team, their strengths, their skill sets and building. Again, this kind of comes back to the concepts around, I guess COLAB a bit, but building that trusted environment where you're not just friends, but you have the trust to challenge and you can loosely hold on to what you believe is the right idea so that when good information or good challenge comes across, you can adapt to that and change. If you are rigid with your ideas and your concepts, that's where I think it starts to break down and collaboration quickly goes out the door.
Brendan Jarvis:
And I also liked when you mentioned describing the collaboration at good nature, also being clear on what the outcome is that you're trying to achieve. I feel like that makes it much easier to discuss the various merits of people's perspectives or ideas when it relates to feeding into where the product might go.
Toby Delamore:
And that's something that we've also had here at Xero, been working across five teams including a UK team, and that's a massive time difference, night and day. And how's that going really well apart from the large bags under my eyes
Brendan Jarvis:
And I believe you've also got a six month old baby in the house, so [laugh], I don't envy that positioned.
Toby Delamore:
Yeah, yeah, sleep is rare. But that was another great example of bringing together teams under a collective outcome, an agreement that was the collective outcome, but the autonomy to execute within their domain of expertise. And that I think really helps you get that successful collaboration because everyone knows what you're trying to achieve and get to and they don't just know it, they agree that is what it is but they haven't been dictated to how to do it. And so each can dive into their world and help solve it. And at Xero we had the UK team working on their part and really doing a great job there and then bringing it to the wider team and a team could challenge that and they would take that away and think about it and vice versa. So that's worked really well, both at Good Nature and Xero.
And I think that's something that product managers sometimes need to remember that sometimes your job is just to help align everyone so they can bring their expertise. You don't have to solve it, you don't have to come up with the perfect plan around what and who is going to do what, bring people on the journey, align them against that common goal and make sure they believe that and understand why that is the outcome required. And then you will start to see their expertise come through and they would do a fantastic job because that's what they're great at. [affirmative]
Brendan Jarvis:
Product management doesn't always just involve the team or teams that you're managing, either does it also involves interacting with stakeholders which may be more senior or in other teams that are outside of the product organization. It's sometimes referred to as a role, the role of product manager as a position where you need to influence without authority. What have you found that has, firstly is that true in your experience? And if it is, what have you found that has worked well for you and having those conversations with stakeholders, getting their support and and keeping them aligned behind the outcome that you're trying to achieve?
Toby Delamore:
Influence without authority is very true. I think it's a good way to of describe the role of the product manager, which is you. You're not the boss, you're not the dictator of do this and it shall be done. And so to me, a lot of it comes down to this storytelling power of product managers. And that comes from this kind of cross-cut viewpoint that you get to have and as I've just talked about, there are expertise in your teams and across the business that you can really bring together for a collective outcome. But your sort of superpower and product is you get to be across all of them and you start to build understanding of the business, of the customer, of UX, of engineering, not at the deep level of the experts, but at a good enough level to start to understand what needs to happen across all of them.
And the critical part of that is the storytelling. So helping stakeholders or different parts of the business understand what you need to do to make an impact. And that comes through helping them understand the impact probably at that customer level, that story about how the business will go into creating something that solves a problem for a customer that is therefore gonna drive the value in that business. So I really think it's that storytelling element and the same guy I tell my team about is don't just come and tell people this is what we're gonna do. Bring them on that journey to understand the story behind it and why it's important. And if you can do that, I think you get people on board and have their buy-in a lot more than just putting up the slide deck that says roadmap A, we're going from here to here, we'll see you at the end. So yeah, story party
Brendan Jarvis:
I was gonna say and whatever you do, don't tell me that there's something wrong with my roadmap because it's been finalized
Toby Delamore:
[laugh], right? Yeah. You dare my roadmap. I beautifully crafted it. I've used some nice colors and I quite like it, so it's not changing. Yeah,
Brendan Jarvis:
I'm starting to think that only children probably don't make the best product managers, but that's just a suspicion, a hypothesis. I haven't validated that. [laugh], we talked about strategy a little earlier on, I think you mentioned product strategy. When was that something that became part of your career or part of your role as a product manager?
Toby Delamore:
Yeah, the first time product strategy really came to the forefront was when I was at trademe and we built out a property data platform which sort of gave people insights into property pricing and what a property might be worth a very topical thing here in New Zealand. And we built that platform and it was great, a great product bought it to the market and was successful. And then that was the point as a product manager realized, well what next path do we go down? What is going to be required to make this successful? And ultimately what is the outcome we're trying to achieve over the next of 3, 4, 5 years? And so that's where I started to realize, well product strategy that is a key part of a product manager's role more so than making sure a product is launched, I think. And that was the first time I sat down and state at a blank piece of paper or a blank slide deck and sort of product strategy, how do I do this? So yeah,
Brendan Jarvis:
It's an interesting topic. It often has as a term or a thing that I find is quite difficult to ground as in just exactly what it is. Mm-hmm. When you took out that blank piece of paper and that pencil and you started to think about, okay, well how am I gonna take this product forward? What does it look like in the future? All those big strategic questions that you just mentioned, did you initially think that what you were doing was product strategy?
Toby Delamore:
I think I knew that was the term was product strategy. What I was doing was not product strategy. [laugh],
Brendan Jarvis:
Tell me about that. [laugh].
Toby Delamore:
Yeah, I think without the kind of understanding of strategy, because strategy is a bigger, broader topic, knowledge in terms of how you do it and what it looks to achieve. And so at that point I didn't have that. So to me I was thinking, oh, product strategy, that's what I do. And really all I was creating was a plan which is a lot easier to do because it is just step one, two, and three. And I think that's a common thing that you fall into with strategies. You think I just need to create a plan build feature A, then feature B, then feature C, outcome being hopefully customers love it but strategy is not a plan. And I think that's what I learned through doing that was as I dug into it more and more I started to realize, okay, it's not just about what we need to do, but the why behind that.
And it probably wasn't until I read a kind of classic and mentioned before book on strategy, which is good strategy, bad strategy which I highly recommend people read. It's big, it's broad, it's focused on business strategy, but it's gonna ground you in the fundamentals of strategy that allow you to look at a product strategy and really determine what you need to answer to create a good product strategy. But the part I always really like from it, and that I kind of refer to as a really simple crux of strategy when people ask me what is product strategy is just defining where you will play and how you'll win. And those were the things at that time, that strategy I didn't know or think about. I thought about the plan, but I didn't think about those two key kind of concepts.
Brendan Jarvis:
I think there's something interesting, there's many things interesting in that actually, but something about the context of when you were starting to do that work is interesting. And I suspect that this is something that is shared by many, many other people around the world, which is clearly nobody else in the organization had a good grasp on what the strategy was for that platform either. Otherwise you would've known about it and you wouldn't have been wrestling with those questions.
Toby Delamore:
Yeah, yeah. I think there's sometimes that thing where there is that is your thing, so you've gotta work out what we're doing with it and maybe there is a higher bit of strategy around it in a business with that sort of layers of strategy. But yeah, it can certainly just fall on your shoulders to work out how you are going to create a strategy that achieves those bigger, broader business outcomes that are defined in a business like Trade Me or Xero. And that that's quite daunting when you're staring in a blank piece of paper saying, well how do I do this?
Brendan Jarvis:
Is it fair to say that when in a product manager's career, they start wrestling with or be being given the opportunity to wrestle with this question of what is the product strategy that they are entering the phase of their career where they move from management more into leadership?
Toby Delamore:
Yeah, I think so. I think when you start looking at strategy, you are moving into leadership because, and again, I like sport analogies, so to me it's sort of moving from being a player to being a coach. And when you're a player, you just are on the field and you just gotta execute. You gotta do your role, you do your job. When you're a coach, you need to be thinking in broader and longer term about what is the game plan for that next game before it's even played. And so how are you going to win based on those factors like another team or the conditions or the skills and strengths you have in your team? How do you leverage all those things, factor all those things to put a plan in place that is hopefully gonna help you win. Now the key part to that is you're not the player who executes it. And I think that's a good reflection into leadership, which is you may come up with that strategy in the plan, which is gonna help to find how you could win, but ultimately there's someone else who's gonna be that player who executes it. And so your role becomes critical in the sense of leadership where you're defining the game plan. You're also now starting to coach, empower, enable others, your players to come in and do the best they can to execute that game to win.
Brendan Jarvis:
I really like that analogy, really do. Toby, are you ready for a couple of scenario based questions that might help product managers that are experiencing a relevant scenario that I'm gonna ask you about?
Toby Delamore:
Yes, yes. We put some good scenarios into our COLAB sessions and I've always been jealous as the facilitator that I don't get to dive in and answer them. So this sounds fun. Well
Brendan Jarvis:
Now's your opportunity. You're on the other side. [laugh], are you ready for the first one?
Toby Delamore:
Yes.
Brendan Jarvis:
Okay, here we go. You're a junior product manager and you're having trouble getting an important business stakeholder on board with your team's ideas for evolving the product. You've got another meeting with them tomorrow and you want to make the most of it. How should you approach that meeting?
Toby Delamore:
Yeah, always tough. And with your meeting being tomorrow, that's coming up quick. I would say work to understand that stakeholder and build a relationship with 'em so you can have a conversation with them about it rather than telling them what you want to do. But what I'd say is go into that meeting with less of a plan to present what you are going to do and go into that meeting to start understanding what that stakeholder is looking for from their side of things. What do they need to be done? What are they trying to achieve? So you can understand that first to therefore look at what you are doing and help them understand how that may even drive some of the things they're looking to have outcomes on. I think a common mistake you can make when you are a junior product owner or someone just kicking off into product is you think your job is turn up and present the solutions and how it's gonna happen and it's not. Your job is to go in there and understand what your stakeholders might need, what they need answered, and then adapt to provide them the information that you have to answer those questions. So yeah, ask them. Cool.
Brendan Jarvis:
Yeah, bring a bit of empathy to that conversation. Yeah. Lovely.
Toby Delamore:
Yeah.
Brendan Jarvis:
Are you ready for another one?
Toby Delamore:
Yes.
Brendan Jarvis:
Well this will be our final one, so second and final one.
Toby Delamore:
Okay,
Brendan Jarvis:
Here we go. A fellow product manager has become interested in product strategy and wants to meet with you as you're known as someone who has a good grasp of the subject. They tell you that the things they've been reading make sense to them, but they're struggling with how to apply them in the day to day. What do you say to them?
Toby Delamore:
Yeah, applying theory to real life is hard and I think that's because it doesn't always work first time. So what I would say is two things. One, don't give up on the first try. There is a reality to trying things in real life that sometimes you have to try a few times understand constraints and what's affecting it to adjust and kind of work through it as well as you just learn, you iterate, you learn and you'll get better as you practice it. And the other is to consider any of your unique factors. So while a book may tell you this is how you write the perfect strategy, you may be in a different business, you may be in a different scenario, you mentioned broader business strategy and the influences that could have on it. So understand those factors for your unique situation, [affirmative], and then work those into what you're doing. And don't feel disheartened if you can't do it the perfect outlined way that an article or a book may tell you so long as the outcome that you get to is a successful one.
Brendan Jarvis:
[affirmative], good advice, always contextualize. Very, very true. Toby, I am conscious of time. We need to bring this down to the close. So my final question for you is, over the coming years, what is your greatest hope for all the talented people who make products?
Toby Delamore:
I hope to see product people really start to shine in businesses and we see it at some of great companies around the world where product is helping lead those businesses to great success [affirmative]. And I hope we see that just grow and product become one of the disciplines at the forefront of business success.
Brendan Jarvis:
That's a great note to wrap things up on. Toby, thank you. This has been such a great conversation, impactful of practical insights for people to apply in their product practice. Thank you for so generously sharing those and your experiences with us today.
Toby Delamore:
My pleasure. Thanks so much Brendan fantastic conversation. Really enjoyed it and look forward to chatting to more product people out there and understanding what they're doing in the world of product.
Brendan Jarvis:
You're most welcome. And Toby, if people wanna find out more about you and also about COLAB, what's the best way for them to do that?
Toby Delamore:
Yeah, best follow me on LinkedIn. You can find me there. That's probably where I spend the most time talking about things, but I'm also always up for a conversation or a coffee and in person or online. So I can share a calendar link where people can book me in for one. And you can also follow COLAB on LinkedIn and just search for all capitals and check out COLABcohorts.com and if you're really interested in joining a cohort, we're kicking one off in June, so get in touch.
Brendan Jarvis:
Excellent. Thanks Toby. We'll be making sure that we link to all of those great resources for everybody. And to everybody that has listened, it's been great having you here. Don't be shy, get in touch with Toby, have a look at COLAB. If it sounds like it's something for you then to apply. And if you've enjoyed the show and you want to hear more great conversations like this with world class leaders in design, UX, and product, don't forget to leave us a review and subscribe. And until next time, keep being brave.

Toby Delamore

Unlocking the Potential of Product People

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