3 Mistakes Product Teams Make (And How to Avoid Them) with Zendesk SVP Product Shawna Wolverton

Shawna Wolverton, EVP of Product at Zendesk, identifies three mistakes product teams make: assuming you know customers without deep data, building homogeneous teams that create blind spots, and failing to kill features that drain resources. She proposes concrete fixes: empathetic listening beyond scripted questions, deliberate diversity in hiring and research, and rituals that celebrate failed experiments.
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Being broadcast now, Shawna, and then you'll just give it about 10 seconds. Take it away. Good luck. Right. Good morning. Good afternoon, everyone. I'm Shauna Wolverton, and I'm the EVP of Product for Zendesk. And as the manager and kind of lead of the product managers at Zendesk, I like to think of myself actually as the product manager for the product management organization. Uh, I don't get to roll up my sleeves and do the work of building product much these days, but I do get to build the sort of teams and processes that lead to great products. But, uh, I have spent my time in the trenches. I'm incredibly lucky to lead a product organization coming up through product and I know how hard this job can be. There's a whole bunch of accountability without a ton of responsibility. And there's just a tremendous amount of work to sort of balance out, you know, the needs of your customers and the needs of your business. But from where I'm sitting, the joy that comes from seeing the impact that the things that you build have on the lives of your customers totally make suffering all of those slings and arrows, totally worth it. And, you know, once you have those customers, they are rarely shy about telling you, you know, exactly what they want. Who among us is not carrying the long list of voice of the customer requests from planning cycle to planning cycle? Maybe if you're lucky, you're even going toe to toe with your go-to-market organization about how many of those, you're putting into your release plan every cycle. But, you know, I think our mission as product people and builders of products is bigger than that. You know, we're not just the people who walk the requirements from the customers to the engineers, right? Our mission is really about building the things that they need. And that comes from a tremendous amount of empathy. And I think there are a few things where, you know, we're all very busy. There's a whole bunch of things going on, and even the most seasoned among us can sort of forget and make some mistakes, right? We're human. And I thought today I would talk to you about a few of those. But before I started, I thought I'd tell you a little bit about Zendesk for those of you who aren't familiar. We are a service-first CRM. Company, and I think when I think about our mission, it's really about delivering the products that let our customers deliver great experiences to their customers. And even before we all scattered to our homes— welcome to mine today— we were incredibly distributed. We're doing product development across 10 global offices and, you know, 4,000 of those employees have been working remotely for a long time. But it has been a great equalizer for us. I have a whole new appreciation for what it's been like to be in the tiny office in Montpellier and to feel a little disconnected. But Zendesk is adjusting, just like everyone else, I think, and learning a lot through this process. So I thought I'd sort of do a little sort of retro, right, on the sort of mistakes that folks make sometimes when we're really going fast and we're thinking about a lot of things and we sort of can sometimes take some shortcuts. And this one I think is especially hard for us to talk about because we really think of ourselves as the people in the organization who know the customers the best. And And I think for me, when I think about what happens here, we make some assumptions. And my biggest assumption that I have made in my career a few times, actually, is forgetting that I am not my customer, right? I think we often have to make assumptions, and our brains are hardwired to sort of make assumptions. If our brains didn't do that for us, we would all still be lying in bed trying to figure out how to get our coffee this morning. And so this is good, right? I mean, I think we need to feel like we know things and put them out there and keep moving. But we can sometimes get a little lost here. I think my biggest example of this is really early in my career. I was building out— a supplier portal for people who did manufacturing. It was super cool. Um, but you know, I had all of these plastic injection molders and metal stampers, and I was trying to build a great platform for them to collaborate with the people they did business with. And I was learning about their capabilities by putting a form in a fax machine and then getting it faxed back. And you know, Shawna, who grew up in the Bay Area, who, you know, shameful confession, my 4th grade birthday party was at the computer lab, right? Thought, of course people want to do this in a different way. And so I built out this great form and surprise, surprise, no one turned up. I got the opportunity when I worked there to go to the world's best trade show, Plastics World. Absolutely nothing better than getting a tchotchke at a trade show that's warm from the gigantic plastic injection molding machines. But while I was there, I got to visit one of these suppliers. And I went into their office, and I saw that they had a row of fax machines, and they were all humming, right? They were sharing design plans. They were, you know, contracts, bids, all was happening on these fax machines. And I asked the woman, where in your office is your computer? She's like, well, the guy who does our books, has a computer in the back. Is that what, what you mean? And I think it was incredibly eye-opening to me that, that something that I would want to use was definitely not something that was appropriate for the people I was building for. And, you know, we got to go back to San Francisco and, and think a lot about how we can incorporate what's happening with faxes. How can we sort of be an interface between these companies who really want to go digital and to start interacting with suppliers in this digital way and accommodate this sort of analog process that was there with, with the customers. And that's something, you know, that, that data wouldn't have told me. I think we rely a lot in product management on data, and it's great, but it doesn't always tell you the whole story. And I think, you know, executives can sometimes fall into this trap as well. I I remember a later point in my career building out a great mobile application, and I had an executive who insisted that we not have a little notification badge because he didn't like them, right? Of course he didn't. He had, like, a whole pack of assistants that checked his mail and made sure the things that he needed doing were done. But clearly, that's not always the experience of our users. And I think this mistake is really You know, you can't understand people and you can't keep learning if you're already really certain that you do. And like I said, I think we all have our amazing dashboards. We have tons of data. We have tons of metrics. We understand, you know, I think to some degree how things are being used. But it sometimes gives us some blind spots about what's really going on and why maybe the things we're building aren't as successful as they, as they could be. And I think the solution here is really about listening. I think as product people, we often, you know, get in front of customers and we have a really strong agenda, right? We have a prototype we want to show them. We have some very specific interview questions that we want answers to that are very specific about the thing that we're building. We sort of listen, but only so that we can get to the next question, or we can say the thing we want to say. And I think the time we spend with customers, it's important to see the bigger picture, to sort of zoom out and let go of some of that really, really deep focus we have on what's right in front of us and understand, what are their lives like? What is it like to be in that job? And shadowing does this to some extent, but even then you sort of miss the forest for the trees. What is their commute like? What are the kinds of things that they might be able to do because they have a coffee break every morning and they stand in line at Starbucks? And is there a set of things you can do when you sort of know a bigger picture about the lives and experiences of the customers that you have. And I think this second issue is really about, um, sort of the perils of, uh, you know, homogeneity. And I think we also in this way are sort of hardwired to really talk to the people that we know and who are like us, right? I think, you know, we hire the people we went to school with or that we had you know, we knew from other jobs. We talked to friends of friends. But, you know, when you find that your interview process is 6 hours of playing Settlers of Catan with the team to see if they're a fit, you might be missing out on some really diverse points of view that you kind of want in the room when you're thinking about product. I think this is something that's top of mind for all of us right now, given sort of the state of things in the world. But it's not just about who's in the room. It's also about really knowing, you know, who your customers are. This is my favorite sort of ridiculously silly story of what happens when, you know, you don't have the right people in the room, or the right people in the room aren't empowered I assure you, I have never thought that my lady hands needed a specific pen that was pink. And I think we're all familiar sort of with this, you know, pink it and trinket, and that's how you reach ladies. But, you know, it's abundantly clear to me that if you, you know, had a woman at the table, this is the kind of thing where you could have saved quite a bit of embarrassment, really. But I think, you know, for a more sort of relevant experience to us, you know, I have a friend who was leading a product team in a Salesforce automation startup in the Valley. And they started talking to a whole bunch of people around them, right? And the biggest thing they heard over and over and over again was about a need to have an integration with Crunchbase, right? All of their customers, all of their partners were startups, and they had this laser focus on really enabling these teams to have a different kind of conversation with the data that could come from that kind of integration. And surprise, surprise, uh, when they took their exciting product announcement out into the broader world, outside the Bay Area, outside of their network, um, you know, the rest of their customers really could not have cared. And, and they had a whole bunch of other kinds of data that could have been interesting, you know, Dun Bradstreet data, Manufacturers of the World, you know, and we can sometimes get a little enamored and a little closed off in our bubbles when we talk to the people that we already know. And I think, you know, this idea of talking to our friends too much is really an issue on both fronts, this idea of who we bring in and put on our teams, and then who are the customers we're talking to. I think, you know, doing product development in 10 different countries definitely is a challenge, right? Staying aligned. There's a lot of overhead that it takes to really keep everyone on the same page and working towards common goals. But what it does give us is this tremendous opportunity to have sort of a built-in level of diversity. What does it feel like to be a customer in Kraków? We wouldn't know that, really. It would be really hard for us to know that without having an office there. And those experiences, the way you do business in different countries is very different. And it's been tremendous for us to be able to use the sort of network that we have internally to really help us build products that are appropriate in a bigger, wider world. So this slide, I made it in the before times. So clearly, we can't literally get out anymore. We're more like in the Get Out horror movie. But here we are, right? And I think it's a matter of us virtually getting out and— I'm not going to say there's a silver lining to any of this. It's gross. But I think there are some opportunities here. And it's natural. Now, I think we used to just sort of say, oh, I have to go get on a plane, and I have to go visit those places to really understand. And now that we're all sort of sitting here staring into the void, it gives us a chance to really broaden our networks. We can reach out. To more people, we can do the research to figure out who the people are we can talk to, and who are the people that we can recruit now, right? I mean, we have— we've all adjusted very, very quickly to remote work. And to be able to leverage that to bring on a different kind of staff, to recruit people from different geographies, to bring that different kind of— viewpoint of the world to the table when you're building things. And then as well as finding a whole new diverse set of customers to talk to. I think we all have the sort of people on speed dial that when we need quick feedback, you know, we know them. They're customers we always talk to. They're the colleagues who give us feedback. And it's a great time now to really rethink some of those relationships and look and do the work of kind of finding a new batch of folks to talk to, because we all know that having a diverse set of viewpoints makes products better. And this one to me is really interesting, right? I think there is a dark corner of how we think about product development that is knowing when to let go. I think we We spend a ton of time building new features, new products, and we're invested, right? Our ego is in there. We think it's the greatest thing that ever was, right? And sometimes it doesn't work, right? And it may not be any fault of our own. It's the wrong time. It's too early. Too late. The world changed. I mean, if you had poured your life and soul into a great product for people who run events in late 2019, you'd be having a pretty rough time right now through no fault of your own. And so I think, you know, we really, really want to be right. And it's really hard when we find out we maybe missed the mark. We had this problem as well, right? We knew that it was critical to a CRM portfolio to have really great analytics, and it needed to be something that we owned and that was part of our own portfolio. So we made a really great acquisition, a fantastic team. We get to go to Montpellier. We even, you know, moved some of our San Francisco staff to Montpellier. They didn't I don't complain too much, you wouldn't be surprised, but we toiled, right? We toiled for years and we tried technological approaches and we kept, you know, they didn't show early signs of working, but we kept at it because we were too afraid to stop and to reassess because so much time and energy had been sunk. Thankfully, finally we had the courage you know, we, we took a step back, we redefined the problem, and we went at it again. And, you know, I think stopping a thing isn't always forever, right? And you can try again. And we did. And the exciting thing is we launched our new analytics product, our sort of enterprise version, just last week. So sometimes it's not no or not never, it's just not now. And I think A lot of the hard part here is about knowing when to let go. We set up so many metrics when we start out about what success will look like, and we don't really sort of say, how will we know that we didn't quite get it right and it's time to stop? We have a whole— I'm sure all of us who run product can talk about a feature where a whole bunch of time was invested and we we're carrying it around a bit like a millstone, right? You know, we got those first 5 customers, they were super excited, and then that curve started to drop off. And we have those 5 customers and we're really optimistic and we're really hopeful, so we don't— we keep going. And that's an important, you know, opportunity cost of a thing we're not working on otherwise. And so I really like to think that we need to have some new rituals here. I think, you know, we have launch parties, and we have cake, and we toast each other, and we celebrate the hell out of when things launch. I'm trying to institute a new practice that it's the wake, right? Every time you try a thing, and maybe it doesn't quite work as well as you thought it would, and it's time to let go, let's celebrate it. Let's take the time to thank it for its service, thank the folks who built the thing, and talk about what we learned from that experience and sort of bring it all back, right? I mean, this to me is, you know, we all talk about the product development lifecycle, but it tends to end at shipping for most of us. And we spend all of this time on discovery and research and building, and we have this thing that we've poured our lives into. And then the lifecycle, we just sort of, it trails off. So bringing it around full circle really constantly looking at your portfolio of what you've built, about what's working, and maybe where you might want to start reinvesting some of that time and some of those people on the next thing, and try again. But yes, have a party, celebrate it. Marie Kondo, thank it for its service, and you get to move on. So, I mean, I think in conclusion, this is really about You know, we're all doing some of these things, right, in some degree or not, and we can all make some incremental progress by investing a little bit in each one of these fronts. We have to listen to our customers and listen to hear them, not just listen so that we can get validation on the things we think we already know. And soliciting the people that aren't our usuals, right? It's so easy. We're so busy. And the time it takes sometimes to go out and find differing views is really critical in making sure, one, maybe you don't do things that are embarrassing, or two, that you don't do things that don't have, you know, a great fit out of your sort of bubble. And then this idea, like I said, that knowing when it's time to let go, investing as much time in that end of the lifecycle as we do in the beginning. So thank you so much, and I'm excited to talk to you with your questions, and I— maybe I can give some answers. Thank you so much. Oh, Q&A. Ooh, already lots of questions. All right. How do you balance intuition and market research when developing products? That is a great question. I think, you know, I call the prioritization process of being a product manager sort of alchemy, right? I think there is a little bit of science, but so much of this is art and, and is to some degree intuition. And I think, like I said, if you're surrounding yourself with a really diverse set of, of people, you can sort of start training your, your gut on when you think you're pretty certain about things, sort of in your guts, and when it's time to go out and, and do more research. I think I am always out in the world trying to understand the competition, the kind of— like I said, there is a very long list of things customers want. But I think we know that to get new customers, sometimes you've got to do something that maybe is a little more innovative than fixing some weird corner of your product. So I think, you know, this is always, like I said, a little art, but definitely something that you can sort of eventually get in tune. What unconventional channel for feedback have you been surprised with? Apologies to everyone who had to do the migration, but in my previous life, I was responsible for the Lightning project at Salesforce, and we put a feedback button in the product, which was something we had never done before. And there was a tremendous amount of expletives in the early days that came through that channel. Um, and what was delightful about that was that they all, uh, got a note back from the SVP of product, uh, at Salesforce. And I got to build actually some really great relationships through that feedback channel, where I think a lot of people were, you know, raging into what they thought was an unmanned inbox. So I think that was great, really going direct to customers. And then, you know, I have learned some really, really great things over the years by, you know, having great, you know, personal relationships with people who were my customers, you know, meeting their children and knowing the names of their pets, I think has been a way to develop a kind of empathy I didn't really have earlier in my career. Um, what am I most excited about from a product development perspective? Have customers demanded most in a post-COVID world? I think that's a great question. I think COVID has really changed a lot of how we're thinking about our product. I think support teams have tended to sometimes be remote teams, but often they were remote together. One of my favorite stories from our own customer base is we called it the chat chopstick, and there was a whole group of people in the room, and when someone was feeling overwhelmed, they would raise up a chopstick with a big index card on it that said "help." And so really rethinking and changing the prioritization of some things, the sort of understanding presence and routing, who's busy, who has capacity, what are the skills. I think that was something we always knew we needed to do, and COVID has really upped the sort of urgency on some of those things. Yeah. What's the biggest mistake you've made for your team? Oh, goodness. This is a weird one, because I do think one of the things I'm most proud of about the way I think about product is really about customer empathy. And I think especially earlier in my career, when I was thinking about the balance between the business and the customer, I— I definitely used to err on the side of the customer, and I think really losing touch a little bit about what sort of the business needed around a cadence of innovation, of continuing to push new things into the market, whereas I was really feeling the pain of customers around some of the— we used to call them paper cuts— that happened in the organization. Push really hard for us to fund and fix a lot of those things. And sometimes there's just really diminishing returns as you go down that list. And so really learning and maturing when to understand what kind of investment to make in really going to the bottom of the pile, right? I think you can have every single feature request fixed and end up out of business because you've lost the ability to get new customers. So that balance has been huge for me and a big place of growth in my own career. Do you have a threshold for determining if it's time to let a feature go? Yeah, I mean, I think it's a lot— there is utilization, um, but you can have, in my experience, you know, you can have a product where you've got 10 customers use the hell out of it, and it becomes a critical part of their business. So if you were just sort of looking at, you know, the customers who bought it and how much are they using it, you'd miss a little bit that it's just not working for— there's just a whole bunch of customers who aren't using it. So I think it's about understanding how— putting some thresholds on how much you're going to invest, both in time and in sort of marketing and sales resources to drive utilization. And I think it's about getting alignment across the business on, you know, what the goals are. And if we're not meeting them and you're not meeting them consistently, it's time to go. Again, this is not so much science, but I think it is important that when you start, to sort of know what those— to align and agree across the business that this is a thing we're launching. Every launch is an experiment and an opportunity for us to learn. And part of some experiments is that you get the data and it didn't work. I used to think I was going to go into the sciences and I was going to be in pharmaceutical research. And I learned that it can take 10 years to get that kind of feedback. Software is amazing. I'm so glad that career choice went sideways. What is your process around talking with customers? Do each of your PMs have customer interviews? Who else is interviewing customers? We're lucky enough to have a really lovely research department. And, you know, in scaling them, what we're doing is, is having them sort of train all of our PMs how to be better customer interviewers. And oftentimes we, we get to kind of do that together where research and PMs go out and have customer interviews. But more and more we are finding that our, our PMs are getting trained to have those conversations themselves. And I think One of the things I want to bring into my organization, I haven't yet, but it was a great thing I heard from another product manager. They actually took headcount and they hired onto the product team a research coordinator. And it was someone who owned helping customers get a whole set of— helping our PMs get an interview set up with customers, which is a huge multiplier. It's, I think, a thing that takes a lot of effort and can take a lot of time from an already busy PM schedule. So really, you know, making that a priority in your organization and making it someone's job to really help you find those customers to talk to can really make this a lot easier. And then I really encourage all of my PMs to spend some percentage of their time, you know, hanging out in the community. I think it's easy for us to sort of delegate that out to community managers or support people, and I think it's a great way to really engage with a passionate set of users. It's often hard, right? I mean, people often will come and, and you have to say that the thing that they care deeply about is not something that's on your priority list. And so I think we tend to sometimes avoid it, but it is a really, really valuable resource. And especially now that we are all sort of in our homes and we're not hosting giant events where all of our customers are turning up and we can't just sort of, you know, tap people on the shoulder in the hallway. One of my favorite things to do when I go visit customers is, you know, walking around if I see the product in use, I'll almost always stop and talk to someone in the organization, and I ask them to tell me what they dislike the most. It's, it's really easy for us to want to hear all the things that people love, but, um, I, I think it's critical for us to sort of hear what's driving people crazy. Um, can you give more advice on how to incorporate these learnings into your product team and processes? Absolutely. So, um, one of the things I've instituted on my team is that when we talk to customers, you write it up and, um, and you share that. And I think, um, you know, making sure that you're not hoarding the information that you learned about your customers is really important. And exposing more of your team. I mean, I think, um, you know, in any product management organization, you have people who are junior who probably aren't getting the kind of opportunities that other people have to really get in front of customers as much as some of the other folks, or they don't have relationships yet. So making sure you're bringing those people along when you have the conversations. Let them ride along. Let them see what those good conversations look like so that they can have more of them themselves. And then making sure you share that information out across the teams. I'm also excited. We have a whole process where customers come in and we interview them actually in front of the whole company. So it's not just product people who are hearing from our customers, but the whole organization can really hear sort of the good, the bad, and the ugly of what it's like to be a Zendesk customer. For a startup just starting out, how do you find those 5 key customers? Oh, man, it's hard. I've been lucky at Zendesk, clearly, where we had some good customers already. But I spent— I call it my year in space, working in a new space startup. And it was really about trying to find product-market fit outside of the traditional buyers of data from space. Turns out governments really want it. But we were sure that there was a great democratization effort. And it took a tremendous amount of leveraging my networks to find people in industries who were willing to sort of talk to us. And some of them were like, yeah, cool, but not ready. And so it really was a lot of trial and error, a lot, a lot of conversations to finally sort of stumble across the people who were willing to really partner with us in those early days to understand what was possible with the data that we had and what kinds of different things they could do. I mean, I think it's It's especially difficult when you're bringing a new capability to market that people really haven't thought of before. I think they didn't know they had a problem. And helping them find the ways in which the thing you're building can bring value is fun, frustrating, but I think it's just try, try, try again. And if you're finding more often than not that people sort of aren't really excited and, you know, those 5 customers are really hard to come by, then it might be time to rethink what it is you're working on. And then let's see, how do you get customers to talk to you? Um, that's a good question. I think we all are very busy. I think You know, when in doubt, there's always bribes. I am not opposed to starting out conversations with new people by offering gift cards for their time or some kind of quid pro quo. I find that at least current customers— this is harder with prospects— but current customers really love feeling special. And, you know, if you can give them a sneak peek of your roadmap, if you can invite them in to talk about you know, helping you shape that roadmap and making them feel part of your process, then they're going to be much more willing to talk to you. And like I said, it— whenever you can sort of get referrals outside of your own network and, you know, get the cred that comes sort of from someone else, sometimes those conversations are easy. But General curiosity. In my experience, people like to talk about themselves, so if you show up and ask people to talk about themselves rather than asking them to listen to you talk, you sometimes get people who are much more willing. How do you get management on board if they're not? Oh my gosh, isn't that— maybe that's my next talk. I think that that is, to me, one of the most you know, one of the biggest challenges, right? You've got a pile of data, you've done a bunch of customer interviews, you're super excited, and your boss is like, "Eh, I don't know." So I think in those cases, sometimes it's a matter of, you know, getting that usage data, quotes. I mean, customer quotes to me are one of the most valuable pieces of information. If you can get someone to tell you how excited and the impact that this would have on their business, they can be very persuasive. And then sometimes it's just a matter of like, well, okay, don't let— I will scrap this together with the resources I have. You don't have to fund it, but I'm going to do this experiment. And then letting the sort of success or failure of that experiment speak for itself. It's tricky though. I mean, there's plenty of times, you know, in my own career where there's been a no that didn't, you know, that I couldn't overcome. And again, I think it's another place where sometimes it's not no forever. I am a firm believer in persistence. Quite a few of my successes in my career were continuing to pitch the things that people had previously said no to. You can wear them down. It's worked for me. And then, how long does it take to make a PO move to a PM role? How do you manage that? I think this is really company-specific. I think a lot of cultures are really different, the role of the product owner. Managing that day-to-day Scrum team, to PM, where you're really thinking more about the business, maybe thinking more outbound. They're really different jobs, and I think we tend to get lazy and sort of dump them all into the same job category. So I think if you're a PO and you want to be a PM, it's really about getting those opportunities to do those ride-alongs, right? Talking to engineers about story points and schedules is very different than having strategic conversations with customers about the value you're, you're delivering. So, um, you know, make sure that you are in a place where, um, the opportunities for you to shadow, uh, PMs are there. And then I think, um, in, in some ways, uh, just start doing the job, right? I think people who sometimes get really up into the day-to-day of product ownership, if they take a step back— I just happened in my own organization, I challenged one of those people to, you know, you're talking about resources, you're talking about all the things you want to do, put it up in a deck, write it down, show up, present to me what your ideas are. And it was phenomenal. So I think, you know, there is very little time in my career where just starting to do the job I wanted didn't at least move me forward a few steps. How do you best communicate that it's okay to fail for your team? Yeah, I mean, I think so much of this is about leading by example. You know, we have a concept we call blameless accountability. I've worked in cultures that were fear-based, and those are places where it's really, really hard to fail, right? Where there's not a lot of psychological safety. So, I think as leaders, it's really important to model behavior. So, when someone shows you something you know, you are curious and you ask questions and, and you're not, uh, you know, pooping on, on their exciting ideas. And, and when something doesn't go right, like I said, I think, um, you know, what are the rituals you have, um, around what happens when something fails? And how do we, I think, build out those cultures, like I said, have a party. And when you have a party and you do a retro and you talk about what happened and you share those learnings across the organization in a way that doesn't call out a product manager for being bad because the thing they built didn't work, then you can encourage and make everyone feel safe that that's a thing they can do. As well. But yeah, it's so much about the culture that you have and what you celebrate and how sort of blame happens. It's really a much better place to work when people feel supported instead of fearful. Can you give any tips to mitigate bias in user interviews? Yeah, it's hard. I mean, I think being aware of it and sort of— I love to do a sort of pre-mortem when I'm talking to customers, like, where is this person coming from? How do I fit this in the hierarchy of the kinds of conversations I'm having with customers? I know that talking to a CIO is going to be a really different kind of— lens than talking to a supervisor of agents, and they're going to have different needs and wants. And, um, sort of thinking ahead of time about some of that stuff is helpful in sort of how do you tuck that piece of feedback into your mental model for, for what the customers or prospects are thinking about. You're always going to have some amount of blind spots. And that's why I think talking to a really diverse group of people— I was talking to a lot of admins early. I had a platform product. I was talking to a whole bunch of admins. And they were giving me all kinds of great feedback. And I started working on this really great onboarding experience for all of these admins. And I went to an EVC. And it was a bunch of IT folks from a bigger organization. And it turned out I had a total blind spot for— I was imagining all these admins being scrappy and doing work all day. And in a bigger organization, right, there were program managers, and there were IT schedules, and there were ways in which change happened in the organization that I had missed. Understanding your buyers, understanding your users, and understanding the sort of layer of people in between can really help you sort of round out the bias of any one person you talk to. Yeah, how do you start building a new group of folks outside your customer friends? I think, um, it's a, it's a good question. It definitely takes work. And I think it is a little bit about putting yourself out in the world. And again, this is a thing that takes time. But I ended up finding a whole bunch of folks to talk to through the community. I had a technical product. I would sometimes find folks who were asking questions out on Stack Exchange. I definitely tend to put myself out on Twitter. And people can find you that way. So it's not always you having to go out. And find them. I think if you put yourself out there and, and in a way that asks for that kind of feedback, you can find a whole bunch of new, new customer friends or strangers. But yes, always sort of, do you know anyone in this kind of company, is a great way to, um, to leverage your existing network to get in sort of circles out from where you are. But I won't I don't want to dismiss at all how hard it is, but I think it's infinitely worth doing. Let's see. Ah, at what point should the head of product stop working on the product itself and focus on the teams? That is a good question. It is the most interesting thing to me about technology careers, right? We start often as ICs, and we have this job that we do, and we get promoted into management jobs. And it is— the new job bears so little resemblance to the old one. And I think it's human nature for us to sort of key, go fall back and do the thing that's comfortable, the thing we know how to do, the thing that feels easy to us, because, you know, becoming a manager, becoming a leader of an organization, when that, you know, we're not born knowing how to do that. So learning those skills is tough. And I think it probably depends on the size of the team. I mean, I have found as a head of product that I cannot also be a team product manager. There's a weird power differential that comes into play when you're both the head of product and the product manager for some set of things that I think can really sometimes make people uncomfortable or maybe even cloud the judgment of some people. They'll want to please you. They'll want to— And you might not get the straight scoop when you're still in the trenches doing the work. So I guess I would say, as soon as it is possible, heads of product should probably get out of the way. Hire a great team, build out the sort of processes and the rhythm that you want, and continue to Be the coach and the cheerleader from your team. And, you know, set up regular ways so that you can give input and you can give feedback. But I think the most important thing we can do as leaders is lead. How can a CEO best support a product leader like you? Ooh, I like that question. I hope you're a CEO. That is fantastic. I think my best relationships with CEOs come from trust. And I think as a CEO, being able to really clearly articulate the outcomes that you want from, from your product is critical. And, and I think what can happen here is that especially CEOs who come up through product, or, you know, were a founder who were kind of early and instrumental in the development of the product, it's hard to separate. And it's easy sometimes to sort of get down in the weeds and sort of air grievances. So I think it's about setting clear goals for outcomes of the product and then trusting your product leader to execute against those outcomes. And that's where you can hold them accountable and then figure out the sort of cadence that you want and the level of detail you're interested in. And we're more than happy to share that with you. What's the best training for people interested in moving into product management? That's a really good question. One of my favorite things about product management and product managers is that, you know, it is, it is not a trade, right? It's not a thing you really go to school to do. Did not have the product management, uh, Lego kit as a kid. Um, and, and people bring, uh, and come to product management from a whole bunch of different disciplines, and I think it's what makes it so fascinating and so interesting to me. And I think the most important skill that you can develop to move into product management is a people skill. I think a lot of people think it's a technology skill or a project management skill, but so much of this job is about humans. The customers are the humans, the engineers who are the humans, your peers in go-to-market and CEOs. You're sort of a little bit of a human switchboard in this job. And it's definitely not one for people who don't find people fascinating. And I think it's really easy for us to think, I have a massive subject matter expertise in area X, so I will make a great product manager. But really, Understanding that this job is so much about human interaction. So, you know, keep honing those skills and finding sort of— it's kind of corny, but like love. If you can find love for customers and the people you work for, then this is a job that even without a lot of skills, I think you can come into and do pretty well. I think you have to have a fire burning in you for the thing that you product manage. Even if you're not the world's best expert, you have to love it because it is a very, very hard job. I think a lot of people think it's some kind of rockstar position, and most of it is a little bit of a slog. And if everything goes perfect and you have a wildly successful product, There's like 1,000 other people you get to thank and give credit to for that. And when it goes horribly wrong, the buck stops with you. What is your top rule for prioritization of products or features? Number of customers, dollars, tickets? I mean, I think my number one prioritization rule is— I will admit I stole this one, but it's customer trust. What are the things that we need to do to continue building trust with our customers? Because if you don't have the trust of your customers, then you don't end up having any. Is this a thing, a bug, a feature, an incident that is going to deteriorate trust if we don't invest in it. And that's sort of— I call that my— it's my zero priority. It's cheating. I have a 1 to 10, but then I also have a zero. And then beyond that, I think it is very much about where you are in a stage of a company. I think there are times in a company when you have to invest higher in sort of keeping the customers you have. And then there's other times when you really have to focus on what are the sort of products and features you need to invest in to really capture market share and go out and grab new customers. So it's not a universal— outside of my priority zero, I think I adjust how we think about where we prioritize and where we invest based on sort of what stage we're on as a company. How do you gauge intensity of the different problems users are facing when doing research? And using that to correctly prioritize product development. This is tricky, right? Because I think if one of your customers has a problem, it's going to be the biggest problem in the world. And I think understanding— someone asked earlier about bias and how do we— if every customer would tell you about things they want, things that bug them, and putting them, like I said, in that sort of mosaic you have of who the customers are. And, you know, is this intensely awful for 20%, 80%? It's important, I think, when you identify someone's really, really deep pain, it's important, I think, to go out and investigate whether or not that's something that's more or less universal than you might imagine and sort of score it that way and think about it appropriately. Shawna, we probably have time for 2 more questions. Great. So I think there's one here about how much time I personally invest in talking to customers I think it is— I feel that there is never too much time I can spend talking to customers. I think of it as one of my primary jobs is talking to customers and then connecting them to folks on my team who can have even deeper and more meaningful conversations with them. But I will never say that— I'm always, always out in the organization looking for more opportunities to talk to customers. If it was, you know, the majority of my job, I would think I was doing it properly. I think there is— and then bringing that and bringing what I learned back into the organization and back into how I'm thinking about building the team and building the process. That we have. It's a huge critical part of my job. And to some degree, you know, my directs as well also spend a lot of their time talking to customers. And the last one, I think, any advice on a fully remote product team? This is incredibly pertinent. I think we are all going through a massive transformation of this as well. I think it was painful before in a way that we sort of were able to ignore, and now we cannot. And for us, it's coming down to writing things down and having a clear sense of what things need to be written down. You know, how do I write down things to start a project? How are things I'm writing down to communicate the status of projects when you're in a whole bunch of time zones? And unable to sort of get together on a regular basis, having artifacts that you can share is incredibly important. We're recording all of our meetings, so if you miss one, you can be there. And then to some degree, too, for all of the structure, I think it's really important to set up unstructured time. We have product cafes that—
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