The Intersection of Business and Design, with former Shopify Product GM Lynsey Thornton

Ep 12

Jul 26, 2023 • 54 min
Lynsey Thornton shares what she learned helping Shopify grow almost 100x as GM of Core Product, VP of UX, and more. We review some common challenges companies hit as they scale, how to identify hires that have high growth potential, how different personalities contribute to team effectiveness, how to design an org for maximum impact, user research as a driver of strategic outcomes rather than checkbox-checking, and how to level up as a leader.

Allen: Welcome to It Shipped That Way where we talk to product leaders about the lessons they’ve learned, helping build great products and teams. I’m Allen Pike. Today’s interview is with Lynsey Thornton. Lynsey was a leader at Shopify for eight years where she held titles like GM of Core Product and VP of UX, has a background as a user experience researcher, and is now a founding partner of Backbone Angels. Welcome, Lynsey.

Lynsey: Hi, Allen. Thank you for having me.

Allen: Thank you for making the time. I always enjoyed our chats over the years when we’ve got the chance to talk about products, and teams, and how all the tricky parts of actually making that stuff happen. So I’m really glad to have you on the show. So before we get into it and dig into some of our topics, I wanted to give you a chance to kind of summarize your background. I did like a one sentence summary, which is fairly shallow given all the fun and fascinating things that you have done. So how do you like to summarize the Lynsey story so far?

Lynsey: Yeah. I mean, it was a pretty good summary to be honest, Allen, but so I guess my whole career has been sort of at the intersection of business and design, and that was even my interest level back in high school where I was hoping to have a career in art, but also wanting to make money, so trying to look for what that might be, et cetera, which ended up in going into multimedia, which was the word at the time, which was kind of jack of all trades, emerging internet, bit of video editing, bit of sound editing, bit of graphic design, et cetera, so that you could make nice websites. Then I did an MBA after that, which was a very unusual route to go, and that was mostly because I was working in a cafe at the weekend and really actually enjoyed that, loved it, but realized that I didn’t know all that much about business, and if I wanted to get to a managerial level in a company at any point, maybe I should know a little bit about that. So that was a weird and wonderful year and a half doing that as well, and I think all the way along since that it’s been trying to find that balance of design and business in roles, and that’s meant sometimes I took a role that was too businessy. Sometimes I took a role that was too arty and trying to just sort of thread that needle the whole time.

Allen: Nice. I love that. The intersection of business and design is I think always been interesting to me. Maybe that’s why we get along well. That’s sort of the story up to sort of gotten into you’ve combined the design, you’ve combined the business. At some point you ended up at a company called Shopify.

Lynsey: Yeah, and I had never heard of them, Allen. I’d moved over to Vancouver from Dublin in July 2012. Sounds like I’m not sure about that. And I got a job here first of all working for a company called Vision Critical in the city, which I didn’t love, if I’m honest, didn’t feel like I was doing great work there, and a couple of minutes into that job, Shopify contacted me on LinkedIn of all places. So as much as I and I feel like most people hate LinkedIn, LinkedIn did me a big service in 2012 by helping one of the Shopify co-founders, Daniel Weinand find me online, and he just sent me a message that said, “Interesting games and design research?” Because up until I moved to Canada, I’d been working in a gambling and gaming company for five years prior to that.

Allen: Ah.

Lynsey: And that was a huge runaway success story company as well, a very similar trajectory to Shopify to be honest. I joined when the digital team was about, as you know, somewhere at like 50 people or something, and I left when it was about 1,500, and we had all the same kind of discovery arcs that Shopify had in terms of small, highly committed workforce, et cetera, all going through it together, all learning a lot together, et cetera, and that’s where I’d learned to do research because, quite frankly, I was designing things that were getting put out and people hated them. So we had the absolute brainwave to maybe run it past a couple of people before it got released and find out whether it was actually…

Allen: Yeah, maybe check out.

Lynsey: Especially as I wasn’t a gambler myself, and so at one point, honestly, Allen, I can remember I was designing the live betting graphics for curling, and I had never watched a curling match in my life, and I was just googling, “What is curling?” Nobody in Ireland knows what curling is. Yeah, that had been my background up until that point, and it was a excellent way to understand human psychology motivation and be able to apply that to what people were doing online at the time and how general consumers were responding to the evolution of the internet. So anyway, so Daniel had found me online, and I googled Shopify, and there was an article that had the title, “Is This Canada’s Smartest Company?” So obviously that was interesting. So anyway, I went over to Ottawa. I’d just moved to Vancouver, and I really wasn’t interested in going down into the -25 situation. So I went over there, and I was lucky enough to arrive on Cyber Monday, which is Shopify’s, obviously, biggest day of the year, and there was such a fun atmosphere in the office. There was just such a good energy, and I was really psyched at the end of the day, and I was pretty sure I was going to join this company. I’d never worked remotely, but I thought, “Let’s see what happens, and maybe I can learn some things, and I’ll give it a year,” and that lasted for eight and a half.

Allen: Nice. And so how big was the company when you started at that point?

Lynsey: I think there Was about 140 people when I joined, and the design team was about 10. I was the first kind of, I guess, user experience generalist on the team. Up until then, everybody had been more of a sort of full stack designer, all designers who could code and were really, really good at building and delivering the product themselves as well.

Allen: Right. And so it was in that kind of Dunbar’s number range where it’s like up and until when you got there, everyone could in theory know one another, and so it was still quite small in the scheme of companies, and then how big was the company when eight years later when you departed?

Lynsey: It was probably… Ugh, to be honest, I’m not even sure. It might have been around 8,000, 9,000 when I left, but it’s safe to say huge amount of change, but also a lot of constants, Allen, like a lot of people were there the whole time. At one point, we had just historically low turnover in the team. We didn’t lose anybody. I didn’t lose a leader off my team in about six years, and so it was just a great place to be. Everybody was getting a lot out of it. Everybody was putting a lot in, and we were just having a lot Of fun.

Allen: Yeah, that’s definitely the sense that I got. Obviously, all things change, but for many years I would sometimes a little bit marvel at Shopify’s ability to hire and retain people out of our Vancouver… We have some really talented people here in Vancouver, and then yet another person would be like, “All right, I’m moving to Ottawa, because I want to work at Shopify.” And then I would be like, “All right, well, I’ll see you in a year or two,” and then seven years later they’re like, “Yep, now I own a home, and I have a family here in Ottawa,” and I was like, “I did not predict that path,” but Shopify has done a good job at both collecting talent and giving them good reasons to stay. So this is interesting to learn that you’ve done this scaling out twice, like in a different position the second time around your more senior roles the second time, but you’ve seen this path twice of a company going from relatively small to huge and growing by multiple orders of magnitude. What are some of the things that you sort of learned, maybe some interesting observations and/or interesting mistakes that can happen when companies go through both the growth and then just try to keep doing great work when you are thousands of people instead of dozens?

Lynsey: Yeah, it’s a great question, and it’s funny because I’m doing a good bit of advisory work now for a VC company called Bessemer, and that means I’m working with series A, B, and C stage companies on elements of scaling, and regardless of whether they’re doing well or not, it’s the same problems and the same challenges. It’s just whether they manage to overcome them. There’s a huge element of luck in there and timing, but definitely the challenges to scale and grow are pretty static. I think just the environments change, but a lot of it is a highly psyched founding team who can rally, who people just want to be around, want to learn from, who hire people that are smart and motivated. Definitely in both Shopify and Patty Power, which was the company in Ireland’s case, we hired reasonably inexperienced people who were highly motivated and looking for opportunities and change, and so that’s a mindset that I’m going to take with me for the rest of my life now I think is that I personally care more about attitude and passion then I do skills. Skills have to be there, right? Otherwise you’re getting fired at some point, but they can be taught. They can absolutely be taught, and so many of the R&D team, for example, at Shopify were non-college educated. I think at one point we did a survey into the company, and there were more master’s degrees in the customer service team than there were in the R&D team.

Allen: Oh.

Lynsey: And that’s because we put such a value on doers, like people who could teach themselves, who could come in, and I really hate the term lifelong learner, but people who just cared enough about something to be sort of doing it in their own spare time, who cared enough about something to career change at some point and teach themselves something else. So for us it was definitely a lot more about the willingness to learn than it was the exact set of skills you came in with.

Allen: So this is interesting to me because often when I talk to different people about hiring, and especially as I get further in my career, I care more about hiring leaders, hiring individual contributors, has a bunch of other interesting trade-offs, but especially when thinking about hiring leaders, you’re talking without I think using the term about potential, right? Like, “This is this person that we think. Right now they might not know a lot about X, but they have what we think are the skills and the underlying capabilities and habits that let them learn about things like X, and they care a lot right now.” And when I talk to other leaders, often I find very divergent arguments from people as to some people will say, “It’s all about potential, hire for potential, promote for potential, build a team of amazing potential, so that you can then shoot for the stars.” And then I have talked to another leader who say, “Potential is basically just your set of biases of how much you think this person… You basically look at them and you imagine other successful people, and then you can’t actually measure that, and plus it’s so easy to hire people that you are excited about the potential, but in practice they don’t actually know what you’re doing, and so that you end up going in circles, and really you should be hiring people who have done it before.” And obviously some of that probably is just like maybe applies at different scales, or I guess that’s maybe my question for at least my first question on that topic to you is like is that hiring for potential really mostly something of you’re a small company right now that is growing rapidly, so you need people with potential, or whatever, however you measure or even try to describe potential, or is that mentality in your mind of hire people who’ve done it before actually going to kind of set you back no matter what scale you’re at now?

Lynsey: Yeah, I think it’s a bit of a mix, right? Those statements I find people tend to contradict themselves on those because life is a big contradiction, and the reality is it is a mix. You need different types of backgrounds on teams, especially as those teams are getting larger, especially as the stakes are higher. When you’re a smaller company, and you don’t have the funds to be dropping a potentially seven figure salary on somebody, then you’re going to go for a potential in these roles because you don’t really have the opportunity to go over to Google and take one of their incredibly seasoned managers who are going to be earning an eye watering salary. I think where we landed over the years, and we went back and forth and made a bunch of mistakes on this, so we definitely had to check ourselves every now and again. Are we still correct on this potential thing? And because, of course, there’s scaling issues with that. There’s no one perfect strategy for hiring, and if you go the potential route, the downside of that is obviously inexperience. The upside of it is capacity to have imagination to innovate and maybe an element of naivety that plays well in terms of their willingness to try new things, and go an extra mile, and all of those things. I think it’s too simplistic to say, “Either hire somebody with experience or not.” Where we landed in the end was you want to be trying to catch somebody who still has growth potential, and so the bigger we got, I saw more and more that people would come to Shopify from the bigger name companies as we became bigger name, and I could tell in interviews that their thinking was, “I’m here already. I’m at the level, and I’m just going to come in, and I’m going to perform.” And we actually didn’t want that because that tended to come in practice when we did hire people like this the reality was that they were coming in and trying to apply what worked somewhere else in the same way at our company, and that just didn’t work in this specific instance. I’m sure that works in some other companies. It didn’t in the psyche of Shopify, and so what we needed was leaders that still had room to grow or people who we didn’t think had peaked, essentially, because the peakers tended to just kind of be there for the paycheck a little bit more, and I’m sure they wanted to do good work and their intentions were good, but the reality was they weren’t growing at the same level of the company, and we needed them to put away the idea that they had already done it all and were simply here to execute again.

Allen: Yeah, that’s really interesting and makes a lot of sense. Of course, everyone has their own… That’s part of the fun of talking to different people and different leaders is like everyone has their own experience, and that leads us to certain mental models that then differ based on everyone else having their different experience, and then you try to make the most of it all, but how much in your instinct is that tendency of Shopify to do best when you were hiring people with this high growth potential and not necessarily as much the people who are like, “Yeah, hire me because I know how to do the thing that you want me to do so I can come do it,”? How much of that do you think was the pace that Shopify was growing at that time, as opposed to any other factor like the inherent culture of Shopify as a learn things, try things type operation?

Lynsey: Yeah, totally. That was a bit big factor. The reality was we were… If let’s just say we hired you, Allen, and you were put into a leadership role, the chances are one year from hire date, your role, team, and department would be completely different. You’d probably be working on something else, and so the capacity for change there was unbelievable, and for people who had a really, really set idea for their career, that was pretty difficult for them, and so that was also something that we tried to kind of screen for was that type of adaptability and understand, like trust I guess, that they could apply themselves in other areas, and that they would be given up opportunities that were interesting continually, even if those opportunities changed. I do think a big byproduct of it was the scale and the rate at the scale was happening, because those teams were doubling, tripling in a year sometimes. At one point, we kind of had to cap it and say, “We’re not going to grow a team by more than a 100% year. That’s unhealthy,” because obviously there’s all sorts of downsides from that and difficulties in delivering and all of those things. Yeah, I do think it was a combination of both.

Allen: Yeah. Okay. That makes sense to me. Definitely I’ve heard more I don’t want to say horror stories, but more bad outcomes of people getting hired with a fixed mindset not being able to grow rather than the other way around, but occasionally you’ve probably talked to people who get hired in at a company that’s kind of maybe the company has sort of peaked where it’s just like, “Oh, yeah, we’re…” I don’t want to throw anyone under the bus, but maybe Intel right now is like there’s a lot of like people think of them as a company that was once great and maybe one day they’ll be great, but right now they’re kind of trying to fight for their lives, and they’re not growing right now. And so if your vision is like, “I know how to do this one thing well, and if in 10 years I still had that same job title, I would be okay with that,” then you might have an easier time at a company that’s fairly stable in size than in a company that’s hyper growth right now, and zero people will have the same title in five years or maybe in three years at that pace. So that makes some sense.

Lynsey: Totally, and there’s a spot for everyone in all different types of companies, and I think that’s just a self-awareness that people need to have when they’re interviewing somewhere. It’s interviewing is always a two-way street, and you’re deciding if you want to work at the company, and the company is deciding if they want you to work there, and that’s where honesty really comes into play I think in terms of how a role is positioned to somebody when they’re interviewing, because if there’s in any way a suggestion that you were to come into Shopify and have some stability, then that would be a lie.

Allen: Yes, and then you’re going to have people who are like, “Yeah. Sure, I’ll commit to this,” but then they don’t know what they’re committing to.

Lynsey: Yeah.

Allen: Yeah, that makes a lot of sense. I think one thing I’ve seen people… And regardless of whether or not it’s how fast the company is growing, but even in just if it’s a fast changing company that people will sometimes over-index on trying to understand the role that as you have sketched out right now on the idea of, “No, no, but tell me more about the role,” or, “so is this role be responsible for X or Y, or will I’ve had final authority over Z?” And it’s just like if you’re too worried about that right now, then maybe this is going to be a problem because whatever currently we think is true could change in six weeks, as opposed to evaluating the company and the people that you’ll be working with, which tends to be more useful I guess for that kind of thing.

Lynsey: Definitely. Definitely

Allen: That kind of brings me to sort of another topic that I thought would be interesting for us to dig into a little, which is all the personalities that come in, right? Where you’re bringing in, you’re hiring people, obviously, you’re trying to hire A players or however you want to label people who do great work that are also growing and also care a lot. And the more people care, it’s kind of like an 80/20 thing, like 80% of the time people who care a lot are helping, but then 20% of the time sometimes that can cause friction, or surprises, or people go off in some weird direction, or they care a lot, but about the wrong things or whatever. So what have you seen in terms of what lessons have you learned or would’ve been your kind of takeaways maybe from the way that all those kind of personalities can mix? You said there’s a position for everyone. Is it really just about making sure everyone is in the right place and that there’s reasonable boundaries, or is it actually like as some people tend to say it’s like, “Well, yeah. There’s all these personalities out there, but at this company,” this company is like, “People with this mindset, then we all get along cause we share this thing in common,”?

Lynsey: Yeah, It’s a great question, and it’s a difficult one as well. I think the important thing is that A, lot of people I notice don’t even think about personality really. They think about skills, and I can also remember doing it myself the first time I was building a team back in Ireland, I can actually remember drawing a diagram essentially of the different types of skills that we had in the team, and then trying to hire for the missing or the weaker set, which seemed totally reasonable to me at the time, but of course there’s a lot more to it than that. It’s the team I think is far more likely to be successful if the personality mix is correct. And by that I don’t mean that either people have to be the same or there’s definitely not space for everybody I will also say. I meant across the spectrum of companies as opposed to in any one given company.

Allen: Oh, I see. There’s a place out there for you, but here may not be the place.

Lynsey: Oh, yeah. It’s just not here, unfortunately. Yeah, yeah. I mean, I can remember we were doing a marketing, or recruitment campaign, or something at some point, and I think the team were sort of trying to talk about inclusivity, but what came out was, “There’s a space for everybody here,” and I was like, “Actually, that’s really not true, and I understand what you’re trying to say, but there really isn’t a space for everybody.” We are hiring for a specific type of personality, and one of them is adaptability to change, like if somebody comes in really, as you said, wanting to know too extreme detail what their responsibilities are going to be, exactly what they’re going to be working on, and they’re really dead set on that, they are going to have a hard time. And so we looked to even screen that out before people came to us. So I was looking for where has somebody sought change in their life, like has somebody moved abroad at some point? Has somebody started a startup? Has somebody taken an initiative and done something to change their life, or have they had the same stable job forever, and lived in the same town forever, and not done a huge amount outside of that? That doesn’t mean that they don’t have the capacity or the stomach for change, it just means they’re less likely to seek it out, and so I was drawn to the people who were more likely to seek change in their life as people who would tend to thrive in that environment. Other people can survive in that environment but not necessarily thrive, so that was definitely something that we were looking for. And then you were ultimately looking for placing them on a team where the goals and sort of general ethos is aligned with their personal goals. So for example, if the team is focused on a set of goals for Shopify that are focused on the merchants that we were trying to build for, but one person on the team is incredibly self-motivated and is night and day thinking about that next promotion, that is a really tricky spot, and that’s an or awkward conversation with that person to kind of get them back on track with what resonates here and the type of results that would be expected to be seen before you can even start thinking about that next promotion, for example. So I do think the balance of personality and skills is one that managers and leaders should definitely consider to gather when they’re building out those teams.

Allen: Yeah, it’s interesting you mentioned promotion oriented behavior and self… I don’t like to use the term self-centric, because that flags people as like, “Well, I’m not self centered. I want to have a path towards my career.” And ambition, like you want people who are ambitious, you want people who understand what skills are valuable. We want people who care about having an impact. I tend to blame it on certain corporate cultures and maybe I don’t know how much it’s people versus what they were brought up in, but there are some cultures that you hear about the horror stories of like, “Oh, well, why did this product fail?” It’s like, “Because the things that needed wouldn’t get written up in a promo packet in the HR structure of Google, so this product died,” and it’s like, “Okay, how do we prevent… We’re designing organizations. How do we make it so that people are motivated, and it’s a clear path to having an impact, but you’re not creating a world where whatever you’re measuring is the only thing that they’re trying to…” I mean, I know it’s kind of inherently I’m like, “How do you solve the most difficult problem and one of the most difficult problems in all people leadership?” But how do you solve that?

Lynsey: It is. It is true though. I mean, I don’t have a perfect answer for that because I don’t think we solved it perfectly. There is nothing more frustrating than at one point I was leading a team that was about 500, 550 or so, and there was always a handful of people who every time I would talk to them it would only be about when is their next promotion, and it was so frustrating because it’s sort of the performance and conversational equivalent of I want you to show not tell, and so it was really hard to explain to people how it worked, and how it wasn’t guaranteed. This wasn’t the civil service. If you were there for four years, it didn’t mean you were going to be a director ever, potentially. You had to do the work to get there, and it was something that we always struggled with was articulating exactly what needed to happen for you to get to a level like director, or VP, or even lead. Lead was a little bit easier because it was often around taking ownership over a larger product area, seeing that through to completion, seeing it dramatically improve, seeing actual customer and monetary results the other side, et cetera, but the higher up you get, the more nebulous it becomes and the more difficult it is to articulate because so much of it is spur an idea for a new business line that makes the company a million dollars. You can’t really say, “Check, that’s a requirement,” because it isn’t as simple as that. Sometimes somebody does something else to go above and beyond in a way that is suddenly undeniable that they’re at the right level to be promoted into something or other. Yeah, so I wouldn’t call it self… Self-centric is probably the wrong word. Everybody is self-centered. Often where it does get out of control for people is if they aren’t getting the clear answers on what is needed to see them through to the next level because sometimes those answers are difficult, sometimes they just aren’t getting clear feedback from people, but that can often turn sort of toxic where people start to, I don’t know, take on more credit for work that was teamwork than their own, or they can start exhibiting lone wolf behavior where they want to do more things by themselves to show that it was them and not others, et cetera. So it’s a tricky situation that I think requires really careful thought and feedback from the leaders and the managers to help the person through and to help them understand that that type of approach doesn’t land that well with their manager usually.

Allen: Yeah, and that all makes a lot of sense, and I think some organizations, especially if you’re a medium-sized company that hasn’t yet seen… It’s often fairly straightforward to write a promotion criteria for individual contributors or to get somebody up to a line manager or something like that, but as you get up in your layers it becomes, like you say, more and more nebulous. And one of the things that I’ve seen people who are newer or the organization is newer, they don’t yet have the language like that you had off the top of your head of like, “Oh, lone wolf behavior, and lone wolf behavior doesn’t land well,” like that kind of stuff to reach to clearly and crisply communicate why the thing you just did, or the behavior that you’ve been seeking, or the things you’ve been prioritizing, I can see why you would think that would lead to you getting promoted, but we don’t yet have a need for this role that you are trying to get yourself promoted to, and going and undermining your team is not necessarily going to get you promoted into that or whatever. So that’s I think part of the challenge is also getting that pattern recognition I think to some of those things.

Lynsey: Yeah, take time.

Allen: Switching gears, something that I also think is interesting, it’s like it’s all related to the skill stuff, but you have this background as you’re talking about as a user researcher, which is one of my first things that got me really excited about software as putting things in front of people and seeing how horrible the thing I made was, and being able to go back and make better.

Lynsey: Never fails to hurt and shock.

Allen: Right, and maybe that says something about us that having that shock then motivated us to do better instead of being like, “Ah, maybe I’m not cut out for this.

Lynsey: Yeah, totally.

Allen: Well, when you think about research and use, so you were doing research at the very base level at Shopify and then up to running our org with hundreds of people in it, that research was a big part of that. How do you think about research and its strengths, and how to use it best, and then how it can sometimes maybe be misused, or underused, or when it’s at its best and when it’s maybe can get misaligned?

Lynsey: Yeah. I mean, it’s been an incredibly interesting decade for research I think from so much has changed in that decade, and people have been doing technology research since IBM in the seventies, but it really has only exploded in the last 10 years, and I think it’s saturated itself a little bit in the last five to the extent that there were probably too many people going into research without the correct amount of training, and there were research teams getting built sort of for quotas versus outcomes, and so research is in a tricky place right now where the industry is kind of redefining itself and working out where to be helpful now, because ultimately that’s your job. There’s no one discipline, I think, is deserves its seat at the table. They all have to be fought for, and they all come with showing your value, and so when I joined Shopify originally, they were at the stage where you mentioned it was probably around the stage where people started to know each other less, but why I was hired was it was kind of around the time when people stopped knowing the customers as much, so it was just that stage where the original founder problem, which was that Toby struggled to sell snowboards online, the team started to get to the stage in size where there were more customer types than just Toby, and people didn’t know those yet. And so the first thing I did was go into customer service and ask what the customer type was like, go into R&D, ask what the customer type was like, and get two radically different answers, and that told me there was quite a lot of work to be done. And how I’ve always thought about research is that it is additive to the business. It’s not a hoop to jump through. It’s not a step that is required along the way. It is an opportunity to expand and advance the business mostly by identifying new revenue opportunities and identifying places to build loyalty and trust with customers. Those are kind of the two big ones for me, and so any opportunity that I could in there I was looking for where do merchants make sales that are not on Shopify? They could be on Shopify. Where are they losing time and money, writing things on paper in their store, et cetera that we could automate or that we could remove from them completely? What do they not want to think about? What parts of their business do they hate? All of these things, and then ultimately, did they trust Shopify and were we in a position to offer more products and services because we had that built trust, and if not, how could we build that back up?

Allen: Yeah, it’s interesting that you say that, because the way you frame… And this probably reflects partially your intersection of design and business, right? Whereas a lot of folks that I’ve talked to about user research in their orgs, and if it varies a lot from org to org in the way the product management also varies a lot from org to org, but that you’ll hear people talking about how user research groups in some organizations spend a lot of their time and attention on basically trying to measure micro benchmarks of things and like, “Okay, well, how… I mean, what percentage of people found this button,” and things like that, stuff that some teams would say, “Oh, well that should just be an automated AB test or some telemetry in our product rather than…” That’s not at all what you’re saying. You’re saying, “Go out and find new revenue opportunities,” which is something that research absolutely can do, but that if you ask five people, “Who on the team is going out and finding new revenue opportunities,” a lot of people would say, “Well, that’s product management is doing that.” So how does that relationship work ideally in your mind?

Lynsey: Yeah. And when I joined Shopify, we were part of product management for… Well, I joined as part of design, moved into product pretty quickly, and then we actually disbanded product for a couple of years, and I moved back into turned UX at that point, but I do think this is one of the pitfalls, and it’s not that there’s no space for that type of work or there’s no business where that type of work is valuable. There is, but it’s sort of akin to a sort of a production designer who’s churning out variance on creatives for a promo. It’s very low level work. I would expect it nowadays to be part of a product designer’s general repertoire, like they need to have a basic ability to watch a customer use the product and have a bit of objectivity and common sense when it comes to what’s been working and what hasn’t. It’s not very hard. So I do think that I would expect that of any product designer today. The researchers, I think the best researchers are given a little bit more space. They’re a little bit more senior. They understand the business very well. They understand technology well enough to understand where that’s going and to understand and make recommendations that help their business line up with where’s tech going, where’s the business going, where are our customers going, and then where do we need to be? And that’s the type of strategic recommendations that I think research is actually helpful for. Is that part of product? Yeah, it should be. I don’t personally care if a company has a research practice or not, and that’s why I don’t really like… People will come to me and say, “I’m here to build a design practice,” or, “I’m here to build a research practice,” and I’m like, “No, you are not. You’re here to provide value for the company, and one of those activities might involve building a design practice or a research practice along the way if excellence in that work is part of one of the things that you think will help you deliver, but no, you’re not here to build a practice. You’re here to show value to the company and be able to display that in a way that is going to make it undeniable that you’re an asset to the business.”

Allen: Yeah, that’s a mentality that is I think very few people graduate from their whatever, their bachelor’s degree with the mentality of, “Oh, okay, my career goal is to have an impact and deliver value.” Obviously, that’s not the way that teenagers think about what their passion is, but that’s the journey that most people sort of… I don’t want to say they need to go through, because certainly some organizations, some individual contributor roles. You can just have this little box, but the leadership path is slowly evolving from, “Okay, I have this hammer, and I know how to hammer things really well. I’m an expert hammerer,” to this much more abstract, much more ambiguous, much more sometimes terrifying, but extremely satisfying when you do it, “I need to have an impact. I need to have a value. I need to be making money, sort of crassly, but making the business more successful using the tools that I have so far, but also often, sometimes even more importantly, using the tools I don’t have yet.”

Lynsey: Yeah, totally. And who does that research work, or who does that thinking around what is necessary in the next couple years and what problems are most opportunistic and most pertinent. It doesn’t really matter who does that as long as somebody is doing it, and all of the roles in R&D change so much over time. This is the other thing to just remember is like you do not pursue a career in tech if you don’t expect your job to be radically different every three to five years. Your job title is going to be different. Maybe UX research won’t even exist as a term in same as multimedia doesn’t exist anymore in another 10 years from now, because it’ll be something else, and it’s not necessarily that the problems go away. The problems are the same, but different roles, different roles and responsibilities, different types of people in those roles are all just different ways to attempt to solve those problems. None of them are perfect. Airbnb’s founder got up at a conference last week and said that they were disbanding product management, and of course this ignites a massive debate on the internet. It doesn’t matter. Every company should be able to approach the work in the way that is most optimum for them to get things done, and so when we talk about placing personalities on teams and different types of roles and responsibilities, for us, they were so fluid at Shopify depending on who was available to work, and who we thought were the best people that could lead it. Roles are fluid, and they should change every couple of years, and I do think people without wringing their hands about exactly whose roles and responsibilities are what, let people play to their strengths in companies, and let people who display interests in certain levels take the lead on those if they can prove that they’re good at those things.

Allen: I think that speaks exactly to what we were talking about before, which is like trying to find people who think this way, but then also foster a mindset on your team of a bunch of people who are solving problems, and building great products, or whatever, at thinking at the more abstract level rather than this ego of I am a product manager. What do you do? I manage product. Who are you? I’m a product manager. What is your goal? To be a more senior product manager. Right? If you really let that just completely become your personality, then if a CEO goes out and says, “We’re disbanding product management,” which I’m sure I’m not having seen the quote, I’m sure he is not saying, “We’re not going to do those things anymore.” He means, “We’re going to reformat the way that title works and the way the reporting and the collaboration works, still having those same activities happen under different hats and things like that.”

Lynsey: Exactly.

Allen: And I’m sure there’s many people who were previously product managers who will be product managers other places, who can have the big impact at Airbnb just in some other way.

Lynsey: 100%.

Allen: But if your whole personality is, “I am a product manager,” then I could see how that would sound like an attack on you, as opposed to an opportunity.

Lynsey: And the changing of a role rather than get your backup about why it’s changing, the question should be, “What is prompting the force for change,” like, “What’s not working that is prompting this discourse and should that be addressed objectively?” Yeah, if people are too entrenched in their, “I am a product designer,” like even the term, “Product designer,” wasn’t very popular about five, six years ago. I can remember backlash at Shopify when we introduced it originally. And so all of these things change, and people need to remember that and be open to that, and your title is not your value. Your value to the company is the set of skills that you can bring, and the personality, and the delivery, and what it means to the company ultimately.

Allen: I think that is a perfect… I couldn’t have designed a better segue into the topic of your role changing. So you came up through this UX path doing UX research, and heading product, and the design team was reporting to you, and then at one point you made the shift to this multi-discipline role where you are leading a totally different type of part of the business, which I was surprised when that you made that change, but very kind of fascinated like what motivated that, and then how did that go? What did you learn from that process?

Lynsey: Yeah, loads. And then at the end, for the last nine months, I randomly switched to a commercial team and was running marketing, sales, support, et cetera, like wild.

Allen: Which is not a path I would have predicted either.

Lynsey: No, no, and technically I probably shouldn’t have even been given that job, but that was really fun, and that was-

Allen: But you learned a lot.

Lynsey: Yeah, totally. And that was the beauty of working somewhere like Shopify. You get opportunities that you wouldn’t get on the street, because you’ve got that trust internally, and you have the opportunity to go for things. The whole way along was a exercise in discipline, expansion, and mindset changing as a result of that. So the first one was we decided to start a content team, and that was given to me, and I can rememberwe had coaches at Shopify, executive coaches, and that was an unbelievable perk. It was by far one of the most valuable things that we did, and I can remember totally panicking talking to my coach and saying like, “Oh my god, I’ve bought this stack of books,” and I was going to have to learn to be a great writer because I thought I was a really good researcher, and that led me to believe that I had to be a really good writer in order to be able to evaluate the content team, and whether they were going to be any good, and whether they were successful, and all these things. And I can remember her being like, “Stop. Do you think Toby, the CEO, has a UX research book on his desk right now?” And I was like, “No. Okay, fair point well made.” And her take was, “Look, you just need to be able to work with them to identify the problems, half of which they already know, or if you’re taking over a team that exists or you’re building one from scratch, you’re either coming in to solve problems that are known, or you are working towards a goal that is fuzzy but available, and it’s just about working with the people to get the right couple of key hires in place that you can trust that you know are good from various sources, doing a bit of research, upskilling yourself so that just enough to be helpful and not to be unhelpful.” And so it started with content, and then when Daniel Weinand left, who was the co-founder, I took over the UX team more broadly. That was super scary. The GM change was super scary. All of it was because the team at Shopify was so awesome, so fun, so skilled, so passionate, and it was so much responsibility to go in and suddenly be responsible for hundreds of people’s jobs, careers, livelihood, et cetera, and then ultimately a million plus merchants over time on the other side. Yeah, there was a lot of self searching along the way and a lot of coaching to try to come to terms with A, not being an expert in those fields, but being able to contribute and starting to work out what the common themes are with great leaders that were discipline agnostic, like what could you see in a great leader regardless of whether they were engineering, or product, or anything else, and trying to apply those, and I would say that that is a lifelong task. I don’t think I nailed that completely, but it was a fantastic exercise in getting okay at it.

Allen: I love that you brought up this idea of discipline agnostic leadership, because that’s something that me and my team have been talking about more and more over the last couple years as we get into these your managing managers type roles, where in my sort of immature younger mindset, you had this discipline chain where, “Okay, well, the most senior developer manages becomes an engineering manager, and then the best engineering manager manages engineering managers.” Of course, eventually that breaks down at some point, but I just didn’t think any further down that, because I wasn’t far enough in my career, but that set of discipline agnostic leadership skills you’re talking about, of which there’s a thousand books written about, but so many things worth learning can pull you through to pretty much any role, even if you sort of don’t have any grounding for it.

Lynsey: Yes.

Allen: And that’s how you sometimes have people who start a company where it’s like, “Oh, okay. Well, I previously ran a tech company, and now I’m running a company that makes outerwear,” or something.

Lynsey: Totally.

Allen: And it’s like, “Well, that seems like completely non overlapping,” but-

Lynsey: No, and so much of it is so common working out what motivates people, the leaders on your teams, whether they’re individual contributors, whoever it is, working out what the intrinsic motivators are of the people on your team is so crucial to not just kind of fumbling a role like that. So you have to know whether, let’s say, is Allen motivated by freedom in terms of type of work, freedom in terms of decisions, freedom in terms of time spent, holidays, that sort of thing? Is he financially motivated? Is he status motivated? None of these things are right or wrong. They just are, and you as a leader need to work out what those things are in order to I think best serve and keep making sure that your team members feel recognized by you. I will say I definitely did not do this perfectly, but I was always trying, and then I think listening. I spent a bunch of time with the different teams over the years trying to work out what is a good engineer, what do you think is a positive engineering culture, what do you think is the best situation that gets the most out of your team and our teams, and just trying to balance those things in your head and work out what the commonalities are across groups.

Allen: I love that you highlighted this necessity to understand what motivates people, because that’s one of those things I was completely naive to, and is actually until relatively recently, I was reading Laura Hogan, who’s like a engineering manager, a coach, and a writer, and she’s awesome. And she had turned me onto and our team onto this idea of the BICEPS Framework. BICEPS stands for belonging, improvement, choice, equality, predictability, and significance, which are in their model it was like categories of things that often motivate team members, and so there’s a little exercise you can do, which I can link in the show notes, obviously, develop a custom one for you that’s advanced version, but if that’s not something that you’ve done with your team members before as working through what motivates them, then there’s this kind of little framework you can do. And we’ve come across with a whole bunch of times. We’re just totally surprised like, “Oh, I’d assumed you really cared about this, but actually you care more about this. I assumed that you cared about improving over time, but it’s actually choosing the path and feeling ownership over what choices we make matters to you more than necessarily that your skills are getting better even though that’s important to you, but relative importance or whatever.” And so that was a really cool, useful tool for me on that path.

Lynsey: Yeah, that’s awesome. I love that people have so many different frameworks for this, and all of them are valid. You can start with a one pager and build this out over time. I feel like if this isn’t something that you have done before and it can be a bit of a daunting task, there’s loads of templates. Just pick one. Just pick one, go for it. If it doesn’t work, you can change it next year and do a different exercise with your team, but anything that takes you from zero to one in terms of understanding, setting aligned goals, and just getting your team members is totally worthwhile.

Allen: I love it. One last thing as we run down on time that I think would be good to touch on, and it weaves in through a lot of the stuff that we’ve been talking about today. We’ve been talking a lot and in different angles from this idea of people want to move up, and have more impact, and be generating value in all our various leadership terms we might use for doing awesome work. We’ve talked about the importance of making sure you’re delivering value instead of just focusing in on your discipline, and doing that in a way that is outsized to the role that you’re in, and doing that in a way that it’s like business value and building those skills such that you do get recognized not for doing lone wolf stuff, but for kicking butt, basically, in the way that the more senior leaders of leadership would think about it. So what would be your advice to folks that are looking at where they’re at in their careers and the role that they’re in to try and kind of supercharge that, basically?

Lynsey: I would say start with your performance goals for the year. I once had a team member who I just thought this was exceptional. He had a very well aligned… He’d written it himself, a very well aligned list of goals and objectives for the year, along with how much of his time he should be putting towards each of these things. So some of it was training and betterment, some of it was product goals, some of it was things that he needed from his team, hitting hiring goals, and the right goals, advancing people in the team, that sort of stuff. He had all this done out himself, and him and I would just go through and tweak that to make sure that that was online with what I was expecting from him. All the way through to the other side of somebody has never written these before, maybe you’ve never written any performance goals for yourself. Step one, write them. Just a one pager is fine. Send them to your manager, see if they land, and then I think an important, very important follow up question is, “What would have to happen for you to be wowed by the work that I do this year?” Because I think when things are written in performance goal fashion, they’re often very check the boxy, sort of ship this product, et cetera, but it is the wow things that really get people promoted, and it’s difficult to articulate that, but it’s a good challenge A, for your boss to be shown that and make sure that they can give an example of something, because, of course, every now and again there’s a situation where nothing is good enough, and somebody just can’t get there no matter what they do, but the more you have written down on the topic, the easier it is for you at appropriate review time, not every time you meet your manager.

Allen: Every one-on-one.

Lynsey: Yeah, exactly, to go through that and check in on where you’re doing, and then I think at a personal level, the mindset that I’ve always found the most helpful is the question of, “How can I be helpful?” Of course, you need to check in with yourself and make sure you’re not being taken advantage of and all of these things, but day to day you I don’t think should be thinking about you. Day to day it’s like, “How can I be helpful? Where can I uniquely provide value that other people can’t? Am I doing those things? Where could I go above and beyond? What do I want to do? What am I interested in?” The more passion you have for the job, the more likely I think you are to do well in that job as well.

Allen: Awesome. Love it. Well, sounds like a plan. We’ll all implement that and get back to us on the show about all of the promotions that this leads to. Thanks so much, Lynsey. Where can people go to find more about you and your work?

Lynsey: We’ve got a website for the Backbone Angels group where we talk a little bit about our investment thesis, the types of businesses we like to invest in now, why we do it. So that’s Backboneangels.com. Other than that, there’s always my favorite website, LinkedIn.

Allen: LinkedIn, hey, it set you on a good path, so we can all make fun of it, but-

Lynsey: It did. It did. I must say I’m fairly lazy on there. I don’t maintain a portfolio or anything like that, so there’s a bunch of podcasts out there that I’ve been on, et cetera if you Google my name.

Allen: Well, thanks so much for being on the show. It Shipped That Way was brought to you by Steamclock software. If you’re a growing business and your customers need a really nice mobile app, get in touch with Steamclock. That’s it for today. You can give us feedback or rate the show by going to Itshipped.FM, or @itshippedfm on Twitter. Until next time, keep shipping.

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