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118 / Empathy, Transparency, and Intentionality in Product Management, with Devan Goldstein

Hosted by Paul Gebel




Devan Goldstein


Devan Goldstein works as Group Product Manager for Trello’s end-user experiences. He’s also worked in product and growth for Dropbox, NerdWallet, and Elevate Labs. Earlier, as a designer, researcher, and strategist, Devan worked for PNC Bank and UPMC and had consulting engagements with Heinz, Dräger, Champlain College, and others, from the Fortune 100 to small non-profits. Devan lives in the NYC area and is a daily meditator, an infrequent short-haul runner, and a karaoke regular.

Success as a product manager requires finding the right balance between solving user problems and meeting rigid business demands. For Devan Goldstein, a Group Product Manager at Trello (an Atlassian product), “product management’s fundamental accountability is to ensure that the business gets what it needs out of the teams it has put in place to do the work.”

That means making sure users are getting what they need out of the product such that, in a perfect world, what they need is something that drives product market fit.

“It can’t be something they need that doesn’t create a sustainable business,” Devan says. “It can’t be something they need that is ancillary to the business’ reason for existing.”

How do we get there? Devan Goldstein believes we solve this challenge by adopting a service orientation, aiming above all to help users, the business, and the team.

“Having this sense of omni-directional caring and empathy – not just for users, which is the one we talk about the most, but for your partners, for the teams that work with your partners, and for your stakeholders – helps us understand how all those overlapping needs intersect as inputs to the strategic and prioritization decisions we have to make,” he adds.

Tune in to hear Devan’s comments on the critical traits that all product managers should possess in this episode of Product Momentum:

  • Empathy for both your users and co-workers.
  • Intentionality in your day-to-day interactions; nothing happens by accident.
  • Integrity and humility, even when they might compete.

Paul [00:00:19] Hello and welcome to Product Momentum, where we hope to entertain, educate, and celebrate the amazing product people who are helping to shape our community’s way ahead. My name is Paul Gebel and I’m the Director of Product Innovation at ITX. Along with my co-host, Sean Flaherty, and our amazing production team and occasional guest host, we record and release a conversation with a product thought leader, writer, speaker, or maker who has something to share with the community every two weeks.

Paul [00:00:43] Hey, Devan, how are you today?

Devan [00:00:44] I’m great, thank you. How about you?

Paul [00:00:46] I’m doing great. I’m really excited to share the conversation that we just finished up. I personally learned so much about areas of blindspots that I didn’t even know I had. I’m wondering, what did you take away from the conversation that we had that you hope people can listen for and hopefully learn as a course of listening?

Devan [00:01:02] Well, thank you. I’m really glad to hear you got some value out of it and I certainly hope other folks do, too. I think one of the things that I find myself talking about a lot at work and that we spoke a lot about here today is the ways that as product managers, despite our firm responsibilities for the business and our users, we also have to think about all the people we interact with every day in order to be successful. We have to understand that, like, each of them is this whole person with a life inside and outside the moment of our interaction with them.

Paul [00:01:31] Couldn’t have put it better. All right, here we go.

Paul [00:01:35] Well hello and welcome to the show. Today we are delighted to be joined by Devan Goldstein. Devan works as a Group Product Manager for Trello and he’s in the end-user experience department. He’s worked in product and growth for Dropbox, Nerdwallet, Elevate Labs, the makers of the Balance meditation app, and Elevate Itself, an app for improving language and math skills. Earlier in his career, he was a designer, researcher, strategist, and Devan worked for PNC Bank, UPMC, and had a consulting engagement with Heinz, Drager, Champlain College, and others from Fortune 100 to small nonprofits. Devan lives in New York City and is a daily meditator, an infrequent short-haul runner, and a karaoke regular. Devan, thanks for joining us. Thanks for making the time.

Devan [00:02:14] No, my pleasure. Thanks for having me.

Paul [00:02:16] So jumping in, I really appreciated your perspective, and speaking with you prior to hitting the record button, it just came through how deliberately you think about product management as a role, not just in business, not just in helping people, not just in end users, but in really a holistic prioritization metric of how product fits within this organizational structure. So I’m wondering if you can share just a peek inside at a high level how you approach this idea of product management, especially as it intersects with business needs.

Devan [00:02:46] Yeah, that sounds great. I mean, I might start with a couple of things I try not to do. I was a designer, as I mentioned, and as a designer, I came up in places without strong product management, in some cases without product management at all. And so I really was focused very exclusively on user need with some sense that what we’re working on in the first place ought to solve a business problem. But really we are solving for user problems. And I think that was a deficiency that I realized over time, particularly as I got closer to product management and growth work.

Devan [00:03:16] And on the other side, you know, being in product and growth, I’ve seen a lot of teams focus exclusively on the business side, like, “What will move this number?” And I think we’re in the middle of experiencing a bit of that, looking at the Threads app, for example, it’s like, what if Twitter had Facebook’s, you know, religious emphasis on growth at all costs? And it’s not a great time for a lot of people who are there now. So for me, balancing those two things is critical. And I think the way I look at it is product management’s fundamental accountability is to ensure that the business gets what it needs out of the teams it has put in place to do work. Ensuring that the business gets what it needs in turn means ensuring that users are getting what they need out of the product such that, you know, in a perfect world what they need is something that drives product market fit, right? It can’t be something they need that doesn’t create a sustainable business, can’t be something they need that is kind of ancillary to what the business exists to do in the long term.

Paul [00:04:15] Yeah, the usable, feasible, valuable, viable through lines and the empowered product teams mantra aren’t just buzzwords for you. It seems like all of those product and business metrics really come back around full circle to also having empathy for the teams that build them. And there was a quote that you jotted down in kind of putting your thoughts pen to paper. And I want to read it because I just kind of love the way that it brings everything together. The quote from you was, “Product managers should, in a sense, begin adopting a service orientation, aiming above all to help users, the business, and the team, in something like that order, rather than prioritizing pet projects that don’t deliver value unilaterally, operationalizing our views of how things should work, or putting our own ego or our team’s concerns above others needs.”

Paul [00:05:00] And there’s a lot to unpack in that idea. But what I took away as sort of the kernel of truth amidst all that is really, when you’re talking to people, they might be people on your team, they might be people that we label end users, there’s always going to be a compromise and a conflicting priority from some stakeholder. Can you walk us through sort of how you came to this, just, I mean, it sounds, you know, very heady and philosophical, but it really comes down to caring about people, is what I took away from it. Is that what you intended in writing those things in that order?

Devan [00:05:33] Yeah, it really is. I mean, I think we talk a lot about different ways of categorizing product managers, right? There’s by domain: you can be an identity PM or a payments PM. There’s sort of archetypes like you can be a GM or a designer thinker, you know, there’s all these different frameworks. I think for me, I don’t know if this is a type or something that I believe should be common to all product managers, but having a sense of sort of omnidirectional caring and empathy, empathy not just for users, which is the one we talk about the most, but for your partners, for the teams that do the work with your partners, for your stakeholders, for shareholders. You know, if you’re at a public company like I am, understanding, how do all those overlapping sets of needs intersect as a set of inputs to the strategic and prioritization decisions that we have to make? And it is a balancing act.

Devan [00:06:21] And I think when we talk about prioritization, typically in product craft discussions, we talk about which framework to use or what kinds of scoring make sense and which kinds are, you know, priority theater. But ultimately that’s the, let’s say, science part. You would call it an inexact science. But then there’s the art part, which is saying, “When I look holistically at this situation that I am at the nexus of, how do I understand which path will lead me to the right set of outcomes?” Or, “How do I form a hypothesis about which paths are most likely to do so?” And, you know, “How do I understand whether it’s working over time?” So I think, for me, looking at it through the human lens as a primary set of inputs and filling it in with quantitative understanding, with kind of on-paper mandates, which are a little less human, a little more organizational, hierarchically driven, it just helps me feel confident that I’m getting the best work done. And, you know, to the extent I have been successful at any point in my career, I think it’s been fundamental to that success.

Paul [00:07:22] Yeah. You shared an anecdote that I’m wondering if I could put you on the spot to recap for our listeners. As I remember it, it was fairly early in your transition from design into product management, and you ended up being installed as kind of the fifth product manager in six months on a product. Can you share a little bit how this, you know, this headiness and philosophy of people and empathy came through in this decision that you had to make?

Devan [00:07:46] Yeah, definitely. I mean, you know, I was a designer, I was a senior designer on this team. I was happy doing it. I was leading the design crew for this piece of our portfolio. And the problem from one lens was that the product management kind of group that had hired PMs for this project was not really hiring for a consumer-facing software portfolio. It was sort of just hiring PMs with, you know, excellence in the pragmatic marketing framework and kind of other sort of more business-oriented, and in some cases, more hardware, or, you know, consumer packaged goods or orientations.

Devan [00:08:19] And so the problem was, you know, when we had the software team and we had software stakeholders who have certain sets of expectations about how the work can go, those ways of working just don’t move the work forward. And they’re very frustrating to stakeholders and they don’t get good work out to users.

Devan [00:08:33] So at some point, you know, I was trying to help as much as I could. I was taking on a lot of the vision and strategy work in a way that was more in line with, I think, how we do it in software design and development and less about some of those other domains. And that was helping. But at a certain point, the operation of the team needed attention to actually follow through on the sort of visions that we were laying out. And so at some point, you know, the request came to me like, “Look, it’s not working, do you want to be the product manager?” And, you know, in my head was kind of like, “Well, no, on paper I don’t; but in terms of wanting to fix what was broken like, yes, I absolutely want to do that. I have talked so much with the team and stakeholders. I feel like I have clarity on how it needs to happen and I feel like I’ve not been able to put that in place by influencing this stream of rotating product managers.”

Devan [00:09:17] So I took it on and I think immediately had to try to recognize that the lens for all my work had been this design lens, and I think that was playing the right role for the team at the time. But I needed to play a different role. And figuring out then, “Great, how do I do the part that I wanted my product managers to do and stop doing the part that I wanted to be doing as a designer, knowing that I have this really capable design team that is still working here and I have great relationships with them. I have formed relationships with the engineers. How do I strengthen those and sort of enlist them to help me right the ship?” And so, again, all of that is about, like, a set of needs I was putting before my own. My own interests were squarely in design. And after that role, I went back to design and stayed for a while and also about that omnidirectional caring. We had many users, we had a zillion stakeholders, and we had a large team that really needed that kind of direction, not in a, “here’s what you need to do” perspective, but in a, “here’s how we need to figure out where this is going together” perspective.

Paul [00:10:23] Yeah, that’s actually a great segue into one of the things I wanted to get to. One of the things that I really appreciated in getting to know you a little bit in prep for this conversation is just how comfortable you are having opinions and how much I think you’ve embraced what is quickly becoming a dying art of critical thinking and really coming with a set of hypotheses about how the world works and what teams need and how products get to market. One of the things that struck me in our conversation earlier was the sense of integrity that you have towards the people and the alignment that you’re trying to drive. And I’m wondering if we could just spend a minute talking about these sometimes competing in forces of integrity and humility in leading a team of product managers. If you wouldn’t mind, could you share just a bit of sort of your flag in the ground on where you see teams most empowered and what kind of information people need in making informed decisions?

Devan [00:11:15] First of all, thank you for some very kind words. I really appreciate what you’re saying about me. It’s nice to hear. And second, yeah, you know, integrity and humility and some other operating principles that are really important for me and people who report to me do come into these sort of funny collisions with each other sometimes. And so I think a great example might be like how you drive transparency down as a leader…

Paul [00:11:40] Mm hmm.

Devan [00:11:41] …While balancing that with a sense of empowerment and an understanding that sometimes you can’t say everything you want to say. Operating with integrity to me means, for example, when there’s something that I would love for the teams to know that they have questions about that I’m just not yet, for example, allowed to say, I will tell them, like, “I do have some information there, I can’t share it with you now.” And for me, that’s not a random choice, right? I’m trying to acknowledge their humanity in this situation that is not fundamentally about humanity and say, “Hey, I know you want to know that; I want to tell you; we together are in a situation where neither of us can get what we want. There are reasons for that, they may be good, they may be bad, they will be clear eventually. But in the meantime, let’s look each other in the eye and say we wish things were different, they’re not, and we’ll figure out how to get there.” When I put that sense of their humanity and my own first, I feel like we have much higher quality conversations as a manager and a direct, as a product leader and a stakeholder, however the case may be. Is that the kind of thing you had in mind?

Paul [00:12:44] Yeah, that’s exactly what I was going for. I think that the way that you’ve outlined this professional tension of knowing you want to transmit something, knowing somebody else would prefer to have the information, but there’s this in-between state of, not yet, you know, already, but not yet. I think that when teams trust that the business has the positive intent and a sense of transparency as much as possible, I called it understated, and I think that’s really what I wanted to pull out of that.

Paul [00:13:09] There’s a, I think a sense where KPIs and vanity metrics and some of the things that we hold up as, “This is what product management should be,” the humanity tends to get lost and people’s sense of ego and pride and also just pride in their work. I think there’s something that comes through in the way that you talk and put your intentionality behind the guiding principles is something that’s really worth celebrating. And a follow-up question on that note of transparency. When you are biased towards transparency and you’re bringing a sense of working out problems together and communicating, collaborating, that takes work, that’s a deliberate act, right? So what are some of the ways that you’ve found success or challenge in creating a culture of transparency? What are some of the risks and what are some opportunities we might not be capitalizing on?

Devan [00:13:58] That’s a great question. It’s really hard. And here I do want to plug my current company because I feel better supported in those efforts than I have anywhere else I’ve worked and I’ve worked some really nice places, but one of Atlassian’s values is open company, no bullshit. And these are, you know, published on the website. And a lot of times corporate values sound great and, you know, we live them to some extent. I feel like the degree to which we live our values at Atlassian and that one in particular is exceptional.

Devan [00:14:24] There are obviously going to be things at any business, particularly one of our scale, that it’s not right to discuss in the open. And so we need to acknowledge that. But biasing towards transparency and essentially putting the burden on the person who wants to keep something from being quite so open to explain why it shouldn’t be, you know, having, as you say, a sense of intentionality about where the exceptions lie is super, super valuable work to have supported. I think a big challenge is when it’s not supported and you want to be transparent, but for whatever reason, you have people telling you, “Hey, you can’t talk about that yet.”

Devan [00:15:03] A great example there is once I gave six weeks’ notice at a job in recognition of how much transition work there was going to need to be. It was like a high buzz factor for me in that role. And I knew it was going to take a lot of work to move things around and make sure things could work after I left. And my manager was upset that I was leaving and asked me not to tell anybody. And every few days and eventually every week, I would check in with him. And he ultimately did not give me permission to talk about it until about three days before I left.

Devan [00:15:32] And so while usually I work really hard to follow marching orders, in this case, I felt like, for the sake of the business, I could not go with what he was saying. And so very selectively and with commitments to discretion, I told a few people here and there as needed, “Look, I’m not going to be here, I can’t share details, but we need to do this work together as though it’s going to get handed off to somebody else because it will.” And for the sake of the work, I felt like I needed to get that done and to share.

Devan [00:16:05] So you can run into frictions like that where I think the desire for secrecy is well considered from one perspective, but not another. For example, it was a time of great change in the business. He didn’t want to rock the boat right then. He wanted to have a plan for my replacement before I left. But it was a hard moment to find a replacement, and so I knew it was going to take a while. So that’s one kind of thing that can come up.

Paul [00:16:27] Yeah. Thanks for sharing such a personal story. I think that that happens every day. You know, we treat those occurrences as if they’re rare, but often people find opportunities and move on, and that’s not a betrayal or a blow to an ego. It’s the professional world in which we live. You know, maintaining empathy in that moment, your boss presumably had the best intentions of not wanting to rock the boat, I’m wondering if we can shift gears into a tongue-in-cheek trademarked term called People’s Traits and States.

Devan [00:16:54] Yeah.

Paul [00:16:55] And talking about how to handle pretty much exactly the conversation that you outlined. When people disagree with you or have competing priorities, what is the bar that you have raised for maintaining empathy? And maybe if you can begin just sharing what is a Traits and States analysis and what value do you get out of that? And then more broadly, how do you build that into what empathy means in that context?

Devan [00:17:18] Totally. So in this sort of set of notes towards an eventual manifesto that I wrote and shared with you and that you’ve been referring to, I do articulate some moments where the work we do cannot just be about the work. It cannot just be about the users and the business. It has to be about our interpersonal relationships at the company in order to succeed. And for me, when I’m talking to somebody else, I think it’s almost fundamental, at least to have some semi-conscious understanding of like, where are they at both in that moment, in the day, in that moment, in their trajectory, in their career, what are the pressures on them? How are they responding to those pressures?

Devan [00:17:54] And of course, like, you can’t sit down with everybody and interview them for an hour about their psychological state and, you know, their astrological chart. But you can get a sense of, where are you coming from today? And you can do that explicitly or you can do that implicitly. I think different people have different ways of doing it. But to me, fundamentally, product management is a weird craft and it is entirely dependent on our work with others. And I’m sure that’s true of all crafts, but in my experience floating around a few of them, I think product has that need most urgently to really meet people where they are, or at least understand where they are and tell them you can’t meet them there because of where you are or what you need.

Devan [00:18:29] So for me, really forming a model of, how am I going to interact with this person today and why based on who they are, where they’re at, who I am, where I’m at, and the organizational pressures around us is, again, key to my ability to do the work in a way that feels successful to me.

Paul [00:18:45] So well said. I think there’s a couple threads here that are really, they’re not synonymous. They are parallel, you know, the transparency, the humility, the empathy. But overall, for me, what I’m taking away is intentionality and sort of, don’t expect any of this to happen by accident. This is carefully crafted, and it’s not about confidentiality or keeping corporate secrets and not wanting things to get out. It’s really about making sure that people aren’t harmed by what we do accidentally or intentionally. But having this sense of, “I have a role and the actions that I take have consequences,” and maintaining that sense of balance.

Paul [00:19:21] I think overall, where I’m going at is product managers often sublimate a lot of work we do, as, you know, invisible to the end product, but really it’s the glue. It comes through in how we craft our sentences, how we write our user stories, how we articulate the KPIs. It really matters. And I think that the intentionality is what comes through most strongly. How do you feel about where the state of product managers are at in terms of the training that we get? Is there something that as leaders we can do to foster this sense of intentionality more explicitly in the training that we give for our junior members or people breaking into the craft for the first time?

Devan [00:19:56] I love that question, and actually a few things that you said point me to the first part of my answer. You know, some of the examples you mentioned, they were all about how we use words, right? How we craft a user story, how we write down our thoughts. I don’t think that on the whole, we emphasize the power of written language and it’s ability to sort of make or break the work we’re doing. I think the burden of documentation on us is high, and so we try to crank out those docs quickly. And, you know, there are great writers who can work really quickly. But I don’t think we have a strong sense of intentionality generally about our writing.

Devan [00:20:30] So for me, although writing is sort of the outcome of a lot of the important thinking and intentions that we’ve set, it is also an act of thinking. It is also an act of forming and reforming your intentions. And I work very closely with the PMs who report to me to make sure that their writing is serving their goals, to make sure that their writing is representing who they are faithfully. And, you know, I’ve run writing workshops for the PMs on my team just as a way of saying we can all always be better at this and it doesn’t come for free. You know, as you say, it’s not just going to happen because we want it to. It has to be really focused.

Devan [00:21:06] The second part of what I would say, like, I don’t know if it’s fair to categorize this as training we can do or something. And I do know that there are companies where this just doesn’t matter. This is not part of the expectation for a PM role. I have not worked at those companies, so I can’t say whether this is still valuable or not. But for me, some kind of practice that helps you understand who you are, where you need to grow as a person in ways that affect your work positively and negatively is critical. For me, that’s meditation and therapy and the kinds of hobbies that put you in a flow state. I play music, that’s a big one. It could be different for other people, but I think when we neglect ourselves as people, we do worse work as product managers. There’s an inversion of the hierarchy. I don’t actually want to say that the reason to work on oneself as a person is to be a better PM, but it does help.

Paul [00:21:53] Yeah. I mean, you’re challenging me. What I’m taking away as my top action item after the things that I’ve learned in chatting with you is that I need to build more time into my schedule for just thinking. I am perpetually busy, vibrating through my calendar about the day and not really spending much time in deep thought or flow state. So that’s a big challenge. And I’m sure for folks listening, it’s often cited as one of the big constraints of our role, just bouncing from meeting to meeting to meeting.

Paul [00:22:18] So we’re coming up on the end of our time together. I just have two more wrap-up questions that I wanted to get at. The first one being, we ask every guest what their definition of innovation is, and I’m always intrigued by all the different answers that we get. I think for, you know, 100-plus episodes, we’ve gotten 100-plus definitions of the word. So I’m curious for yours. How do you define the word innovation?

Devan [00:22:39] That’s a great question. I think, to the point about language, there are lots of different ways to use the word. I think in a sort of blanket, what is this noun context? For me, innovation is an outcome. Innovation is the outcome of a set of practices that are designed to move a business in the right direction. Sometimes, frankly, like a business does not need to innovate to move in the right direction in that moment in time. You know, over a long term, probably every business needs to make it happen, probably many times. But innovation is the outcome of a set of processes that, when necessary, will lead to fundamental changes in the products and services that the business offers, the way it brings them to market, or sort of related factors there.

Paul [00:23:19] I love that answer. Well said.

Devan [00:23:20] Thank you.

Paul [00:23:21] Yeah. The last question that I have for you is, you know, what’s inspiring you? What is a book that you think should be on every product manager’s bookshelf, and where can people find you and get connected to the things that you’re talking and thinking about?

Devan [00:23:33] It’s a great question. You know, to be honest, I struggle with books. I’m going to recommend one and then recommend something very different. You know, I love Marty Cagan’s writing and, you know, Empowered most recently is the one I read that really spoke to me. And I also appreciate that it’s written in very short chapters, which is compatible with how I like to take in business content.

Devan [00:23:50] I think for me, to be honest, you mentioned early on, you know, that I focus on things like critical thinking and holistic understanding of what’s going on. It took me until many years into my product career to understand the value of my humanities degree. And I would say for that reason I read mostly fiction right now, and I find two things. One is it just helps my brain get shaped in ways that are broader than the work I have to focus on very narrowly every day, which is valuable in the long term. And two is, you know, the fiction I read is mostly about people and their traits and states and the actions they take as a result. And so I think it’s a way of helping me understand, how do people interact? What kinds of things can be at stake that you can’t see as a colleague, but you can see as a reader, you know, reading a book about a made-up person?

Paul [00:24:35] Mm-hmm. I love that. I love that answer. Devan, it’s been a pleasure. I think the things that we’ve covered are not often talked about, but really important for building teams that are healthy, building products that are useful. So thanks again for taking the time. It’s been a blast.

Devan [00:24:49] No, thank you. I really appreciate it. It’s been tons of fun.

Paul [00:24:51] Cheers.

Devan [00:24:52] Take care.

Paul [00:24:55] Well, that’s it for today. In line with our goals of transparency and listening, we really want to hear from you. Sean and I are committed to reading every piece of feedback that we get. So please leave a comment or a rating wherever you’re listening to this podcast. Not only does it help us continue to improve, but it also helps the show climb up the rankings so that we can help other listeners move, touch, and inspire the world, just like you’re doing. Thanks, everyone. We’ll see you next episode.

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