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Get another look into how Postlight works as Chris and Gina discuss how specific training and onboarding guidelines can restrict progress and creative approaches to project delivery. Can encouraging critical thinking lead to better products and happier clients? How much freedom is too much? And do the benefits match the costs? 


Gina Trapani: Unique New York. 

Chris LoSacco: Unique New York. Unique New York. 

Gina: Unique New York. 

Chris: Unique New York. Unique New York. Red leather. Yellow leather. Okay.


Chris: Welcome to the Postlight Podcast. I am Chris LoSacco, the president of Postlight. A digital Strategy Design and engineering firm based here in New York City, and I am joined as always by my co-host and partner in this business Gina Trapani. How are you, Gina? 

Gina: I’m doing well today. Doing well. 

Chris: Great. I would like to talk today about how we do our work. Which is kind of what we talk about every time we get on the podcast. I guess. 

Gina: We do. We talk about how we do our work a lot. I love it though. Never tire of talking about how we do our work. 

Chris: Never tire. I mean, if nothing else we like to share the good and the bad about this business. And hopefully people can derive some value from it. 

Gina: I mean, making software is just messy. It’s messy and chaotic and it’s, it, it needs a lot of talking about, because we are..

Chris: It needs a lot of talking about.

Gina: …constantly figuring things out.

Chris: You know, I came to product management before product management was really a title, and I think even today, we’ve talked about this before, like if you ask a product manager, what does product management mean? You ask 10 people, you’re gonna get 10 different answers and there’s gonna be some overlap, but there’s a lot of room for interpretation when it comes to how do you run a successful software product? And there’s product manager versus product owner versus, you know.

Gina: Project manager. 

Chris: Exactly. 

Gina: Mm-hmm. 

Chris: There are—there are 17 different permutations of what is, you know, kind of like the same role. But what would be maybe interesting to talk about is there are some firms that embrace a particular way of doing things. They say, “We are an agile shop.” Or “we are Scrum.” Or “we are CanBan” and “this is what we do and we want to train our people to know that process inside and out so that when you join, you go through the bootcamp or, I mean, you can get certified in these things now….”

Gina: yes. 

Chris: “And once you know what it is, great. Now you can come in and run that process.”

Gina: Mm-hmm. 

Chris: And we’ve taken a different stance, not that there’s anything wrong with approaches. But the way we’ve treated it is that there is no Postlight way. 

Gina: That’s right. 

Chris: There’s no training document that you can read or slide deck that you can go through that says, here’s exactly how you run a project at Postlight. And—and you know, it is both great and terrifying. It’s, I think when you—when you join this company, and I would love to sort of talk with you about the pros and cons of doing things that way. 

Gina: Yeah, I mean, let’s do this. Let’s do this. This has been a con—constant conversation during the seven years of—of the company’s existence. And you know, if you look at, if you look at other shops that have these—that are subscribed to either, you know, to a certain way of running projects like Agile or they market and package up or commoditize like their, you know, they—they give it a name and they say, “We do the—the big think” or whatever it is, or , you know, 

Chris: Right. Little trademarks symbol.

Gina: ” Special build,” you know. And like this is, these are the steps that you go through. And these—these beautiful slides and it’s just all packaged up and you’re just, you look at that and you’re like, “That makes a lot of sense. Yeah. I wanna run my stuff through that…

Chris: yeah.

Gina: …particular Rube Goldberg machine and sees what comes out at the end.” Like that—that these people seem like they know exactly what they wanna do. And I gotta tell you, you know, when I, There was a time when I was running marketing at Postlight and I was like, Should we, you know, should we think about something like this? We flirted with it a little bit with relay our—our design sprint. It’s like, “okay, we can name it something.” And—but for the most part, overall we’ve made, we’ve kind of put our stake in the ground and said, “actually, Custom software,” which is what we build for our clients. We, you know, we’re not a particular kind of shop that builds a particular kind of thing and a particular kind of size, a particular kind of technology, right? Like every project that we do is unique, “requires just the—the ability to, you know, custom fit your process to the—the client.” So what needs to be done. 

Chris: Yes. 

Gina: Which is a pretty controversial take.

Chris: Right.

Gina: Especially for incoming PMs, who we just hired! 

Chris: That, I mean, that’s the thing. And what, you know, we’ve invested some energy in how we do project oversight, right? Across many active projects. This is our QORE process. Q O R E, quality, opportunity, risk relationship, and efficiency, which we wrote about extensively in the handbook we just—we published on our website. But when it comes to project work, yeah, we give our teams a lot of autonomy. And—and you said to me in the past, like, we work on the movie model. We work on the idea that you get, you know, a great director and a great cinematographer, and great—a great cast and—and a fantastic crew, and you put them together and you have a vision for the movie and—and then you let them go do their thing.

Gina: Mm-hmm. 

Chris: And you don’t say, “Here’s exactly what you need to do on a day by day, week by week basis.” And I think there’s tremendous flexibility in terms of what those teams are then able to—how they’re able to self-organize. 

Gina: That’s right.

Chris: And you just said, you know, it’s also important that every client is different. We do client work, so how do we make sure that our process is mapping to our clients? And that is so critical. Because do some clients wanna really embrace iterations and sprints and story points and the like? Yeah, they do. But not every client does. Some clients, right? They really value predictability or they have a very strict release cycle where you have to be thinking about it. Or you know, some clients wanna be in Jira with you and other clients don’t even wanna know about Jira, right?

Gina: They don’t know what Jira is. They don’t wanna know. Yeah.

Chris: That’s right. And so being able to define what is right for this situation is a—a tremendously powerful thing, but it does require that the team embraces the work. The work is what I wanna say of, of, of doing that setup because every single time you can’t take it for granted that you know the checklist that you have to follow. You know? 

Gina: That’s right. 

Chris: “Oh, I know how to do sprint planning. I’ve done it on my three previous projects.” And it’s like, “Well, on this project you have to be explicit about what version of sprint planning or not is going to work for this team, this environment, this client.”

Gina: That’s right. And it adds a lot of, a lot of overhead. I mean, and you know, in some projects we’re side by side with the client sitting next to them and working with them. So we wanna maintain that flexibility and adaptability to work with them, meet them where they are, right?

Chris: Yep. 

Gina: Work with them the way they prefer to work with them, work themselves. And other times, you know, we’re just greenfield on our own. You know, just start like—and we’re—and it’s up to our team to say, “Okay, here are the tools we’re gonna use here. Here’s our meeting cadence, here’s how we’re gonna talk to one another. Here’s how we’re gonna estimate…” There’s a—an investment up front that has to happen. Cause there’s no assumptions. Because everyone is coming from a different project that did things maybe, you know, in a particular way. It doesn’t mean that’s gonna be the same in their next project. I mean, this—this is—I think works you know well and is justifiable in an agency context when everyone is working on different client projects. Like I can imagine somebody in house listening to this right now and thinking, “That is totally inefficient and weird. Why, you know, why wouldn’t you have company-wide sort of standards for how, how you do things?” Right. I see you kind of shaking your head back and forth… 

Chris: Maybe!

Gina: … because you know, I mean maybe, maybe more autonomy and more like, Hey, why don’t you figure out how you wanna work together versus follow the—the company formula is—is a better way. I think it’s worth that consideration. 

Chris: Here’s the thing I want to ask you though. Do you think the company formula is adequate to answer all the questions that come up when a team is working together, even if it’s an in-house team with a presumably a shared understanding about where they’re going? 

Gina: No, I don’t. I think that a prescribed process, kind of, it—it invites folks to just sort of—I think that you kind of default to or lean back on the process. 

Chris: Yes.

Gina: It discourages some critical thinking and I think that, particularly when you are working in strategy in innovation, like the whole point is that you burn the whole thing down and you just, and you think big and you ask these fundamental questions. Like it’s just part, part of that process is—is doing that right. I’m saying part of the process is not having a process. But, but you just, if you, you know, if, if you hire in an employee and you say, “Okay, I give them the training. Okay, steps one through 30, here’s how we run this particular process.” It just at that. You know, you’re just, you’re just going through the motions. You’re on the assembly line. 

Chris: Exactly. 

Gina: Right? And you’re not thinking like, “wait, this could be better if we did this. Like, it doesn’t fit into the boxes here, but this could be better.” Right. And so you wanna create, I mean, part of what we do is create that space for we’re, we’re outsiders, we’re coming in, we don’t know anything. We are not wedded to any of your culture or processes, or, We haven’t had any of your trainings. So we’re gonna just start from the beginning here. You’re asking for different thinking when you, when you’re trying to make great product, when you’re trying to make a big change, create a system that is gonna, you know, make things better in your business. And, and it’s hard to do that thinking when inside a, a training, you know, process that you got trained on.

Chris: It draws a, a box around you. It draws your little playpen and it, and it’s so easy to not even think about what’s outside of that playpen if it’s strong for you. 

Gina: Yeah.

Chris: I’ve seen it really handcuff teams and their ability to like do—not even do like groundbreaking, innovative stuff, right? But just do anything that’s outside of like, going through the backlog and handling, you know, small bug fixes. Like, and you come in and you’re like, “But what, what are you doing?” And they’re like, “Well, we’re getting through, you know, 14 points of sprint.” and you’re like, “What is happening?” It’s so funny when I think about Agile, I go back to like the original Agile manifesto, right? 

Gina: Yep. 

Chris: Which is individuals and interactions over processes and tools. 

Gina: Yes. 

Chris: Working software over comprehensive documentation. Customer collaboration over contract negotiation. And responding to change over following a plan. Those are the original tenets. And it’s fascinating to me that you get, you know, product managers and companies who are like, “Well, we’re a, you know, we’re agile. That is how we build software.” And then you go in and it’s, in some situations, it’s the opposite of this. It’s like, “well, we don’t wanna talk to the customers because we have our backlog and we need to story point it,” you know?

Gina: Right. 

Chris: Or “we, we are gonna, we’re gonna focus on making sure our confluence is looking really great.” Instead of, “No, you gotta think about what you’re building and make sure you’re building the thing.” And if you’re too capital P process, you lose the idea that the process is just a means to an end. 

Gina: It’s a means to an end.

Chris: That is not the thing you should be thinking about. The thing you should be thinking about is the platform that you’re building or the product that you’re launching. And unfortunately, especially for people early in their career, I think it’s too easy to lose sight of it if you, if you’re heavy handed with, “Here’s how we do things.” 

Gina: Right. “You did five points this week and not seven, like what’s wrong?” Right? Right.

Chris: Exactly. 

Gina: But why? Why? What are we doing? And, and, and does this, does this align with what we’re trying, which, what we’re trying, we’re delivering value to the user, right? Like those are the conversations I’ve been in. Gosh, I’ve been in so many sprint planning meetings where I just, my soul, like, left my body, like, floated out the window. Cause I was just like, we’re, I don’t even know what are we even do like , right? What are we doing here? You know? I was like, well, okay. You know, you, like, estimate how long you make the burn down trial. Okay. Like.. 

Chris: Right? And it’s all this meta work around things that are just not gonna move. You know, there—now there are some teams that I’ve seen do it really well, and they use sprint planning sessions to say, “Let’s make sure we have a common understanding about where we’re going so that we can run really fast after we have this understanding.”

Gina: Mm-hmm. 

Chris: or, “we’re gonna story point things because we have a bunch of new engineers on the team and so we’re gonna use story points as a method of communication.” Or you know, in our world, we’ve often championed t-shirt sizes, which are like, you know, it’s a, it’s a version of story points where it’s like, let’s think about when something is small, medium, large, extra large, and then if something’s extra large, it’s like a, you know, big flare that goes up that says, Oh, we’ve gotta unpack something here.

Gina: We gotta break this down. 

Chris: We’ve gotta break this down. Yeah. And we’ve talked about the importance of estimation at length, I think on the show, and, and that, you know, There’s a real, there’s real value there, but it’s when you get too married to the abstractions that the problems start to come in.

Gina: That’s right. 

Chris: And the reason why I think we’ve been pretty adamant that we’re not going to decide on one particular way of doing things is because we, we wanna avoid exactly that happening. We want to avoid people mistaking. I really get the steps. Instead of thinking what does the client care about and what is that next milestone and what, what expectations have we set and how are we exceeding those expectations? Those are the kinds of questions that we ask in our core sessions, in our core process, right? Those are the things we really care about, about the project or about the client, and it’s not the, you know, “Tell me how you’re performing on your burn down.” 

Gina: That’s right. I mean, I’ll say there is one Postlight way, which is like giving people that room. You know, we, we’ve called it, you know, Duplos and not Legos, right? Like T-shirt sizes, you know, small, medium, large, extra large is a version of story points. Just a lot less granular, right? Like, I, I don’t wanna argue with a PM or have a PM arguing about whether or not something should be five points versus eight points, right? Like, but you know, small, medium, large is that they’re bigger blocks. And I think that those bigger blocks, you don’t get necessarily the absolute precision. Like we, you know, we also, like, we don’t count hours , we don’t have people’s time sheets and count hours, Right. Because it’s just, you know, what value we’re delivering in the time that you’re spending. You know, we, we also like, we, we avoid these like super detailed Gant charts, you know? 

Chris: Mm-hmm. 

Gina: with these cascading dependencies. And if one thing goes a day long, then the whole, you know, all the dominoes fall. We, we kind of make this big blocky chart where we think about this, about a time is gonna be discovery. Right. But we, but in, in doing that and being just a little bit more, Generic and less precise, you get—you’re, you’re saying to your team, like, “I know you’re gonna figure it out. We know a things are gonna change and we know you’re gonna figure it out.” And also like, “we expect you, team, to be talking to one another and working with one another in a way that works the best.” like it’s very heavy handed. Some of these processes are just so heavy handed that it, like, takes the thinking out of, like, the talented professionals who—who are solving very complex problems. 

Chris: That’s right. That’s exactly right. And—and you said it before. What we wanna encourage with our projects is critical thinking, right? Internally and externally. We want people to think about the choices that they are making and think about the choices that their clients are making so that they can help contribute to them. Right? And I—and reinforce the ones that feel like good choices and, and hopefully redirect or change the ones that feel like bad choices. And if you are not thinking critically, instead, if you are following the predefined steps that have been laid out in the, you know, onboarding 1 0 1 doc, you lose that entire motivation. And I would posit it’s not about job levels. Like, I think this, this sort of approach naturally lends itself to more senior people, which is how we started the company. We hired a lot of senior people. I’ve been really surprised in a positive way that our associate level product managers, designers, and engineers, the ones who are really good, embrace this. They like the fact that they don’t have, you know, a template that they’ve gotta sit within. They like the fact that they’ve got room to run and they can really connect with what the ultimate outcome is going to be and go after it. And this is not outta the realm of possibility for people who are early in their careers. In fact, it can be very—Now you have to, you have to have oversight. Right?

Gina: Right. 

Chris: Which is again, where I come back to our core process and being, being able to check in on how things are going and course correct where needed. That is important. 

Gina: Right. 

Chris: But I don’t think this way of working is incompatible with hiring junior people. 

Gina: Yes. I think that’s right as and as long as you, as long as you set their expectations and say you’re getting this reading, you’re getting some more autonomy. You’re gonna learn a lot about yourself and the tools that you like to use and your team, you’re gonna make mistakes and realize that didn’t work and you have to adjust. And that’s a particular, I think that’s a particular personality that—that, like, likes that and wants that, you know, that freedom and autonomy and doesn’t wanna want the checklist. I totally agree. I totally agree. But I do, I wanna be honest though about some of the cons. To, to this kind of freedom. 

Chris: Go for it.

Gina: There have been times, and this, this surprised me and it was somewhere between like 40 people and a hundred people that this started to happen. 

Chris: Mm-hmm. 

Gina: where, you know, we would start to get this question, this question, what would come up again, “What’s the process for X? Like how, what’s the process for X?” and in a lot of cases, and, and I’m even talking about just, like, internal, internal things . 

Chris: Sure. 

Gina: Operational things. And I’d also be like, there’s no process. Talk to a person. You know, like the, I, we don’t have a form and a system and a platform. You just, you just talk to a person. Right. But after a while, that starts to not scale. Right. And so you sort of have to put some, some processes in place. And, and there are times when we’d have, you know, new, a new PM or a new engineer and they would say, you know, in their first week, you know, “Any questions about Postlight?” “How do people do X? Like what, So how do we do this here? Like what, what do…”

Chris: at the company level You’re saying?

Gina: At the company level? Yeah. But even on a—on a project, like where can do, do we use Jira here? Do we use shortcut? Do we like Trello? Like what would be, And our question, our answer would be, It depends. It depends on the project.

Chris: Right. 

Gina: And it depends on the team you’re on. And we would get, like, some confused looks.

Chris: Right.

Gina: And I, and I think that, that it does add that overhead at the beginning of the project where everyone has to see not only the beginning, it’s, it’s something that throughout the course of the project, you have to course correct and get with your team and, and check in, how are things going? The choosing the tools, figuring out the communication cadence that, you know, how we’re communicating to the client, how we’re communicating to one another. We have to figure that out, kind of, fresh every. 

Chris: That’s right. 

Gina: And, and there have been times when I think the disciplines, you know, product management, engineering and design, I think that those teams come together and talk about prior art. What are other—you know, we try to learn from every engagement that we have. What worked well, what didn’t work well? Oh, I’ll try this. Okay, that didn’t, you know, and, and we have tools that become popular for a while and then, and then fall away. And that’s, that’s, that’s natural. We—we’ve also taken a very hands off approach to, if you wanna use a new tool, like we’re product people..

Chris: We’re product people.

Gina: There’s a new interesting tool out there and you wanna use it? 

Chris: Go for it. 

Gina: You should go ahead and use it.

Chris: Yep. 

Gina: Yeah, Yeah. You should know what, what’s new and out there just to be informed and you, and you honestly, you don’t really know things until you use them. So we encourage that. It means that our SaaS, software [laughs] bills are—[laughs]—are…

Chris: Well, it’s a constant [laughs].

Gina: It’s a constant, Yeah. It ticks up and down. 

Chris: Right? 

Gina: Like.. 

Chris: We—we always ask ourselves, are people still using this? And you know, if so do, can we reduce the user count ? 

Gina: Yeah, exactly. Exactly. So—so I think there’s a little bit of like, I think that. There’s, there can be a perception that there’s a, like, this is inefficient. Why don’t we just put a stake in the ground and say the—these, this is how we do things generally, you know? 

Chris: Right. 

Gina: I mean, I kind of get that from the perspective of someone particularly new coming in, being how do things happen here at Postlight? And the answer is like, you get to decide. You know, it can always be like maybe too much freedom.

Chris: I mean, I understand that. I think it still feels like the right trade off to me. 

Gina: Mm-hmm. 

Chris: But I understand that —you’re gonna pay a little bit of a price in efficiency because you do have to invest upfront, right? 

Gina: Yeah. 

Chris: When the cast and the crew and the director of the movie come together, they have to—they have to be explicit upfront about how they’re gonna do things.

Gina: Yeah.

Chris: And if they’re not explicit upfront, that can also lead to problems because you can. You can’t assume that you can fall back on a common understanding of things, cuz there is no real common understanding. Like everybody kind of has their own flavor of it. Even people who have been at Postlight for, you know, two, three years, they have their own project experience, which may not translate into their next project.

Gina: That’s right. 

Chris: So I totally agree with you. It’s one of the downsides that you, you pay a little bit of a tax in efficiency because you’ve gotta be explicit about these things. One thing though that is worth calling out that we’ve tried to do is create Shared artifacts that can help, that you can, that you can tap into depending on what you decide for your team. There’s this collection of things called the project toolkit, which is exactly what it sounds like. It is a toolkit of things you can use on a project. So it includes….

Gina: You can choose. Yeah. It’s a buffet rather than a, Yeah. Seven course meal. 

Chris: Right, And it includes client kickoff decks or, you know, engineering architecture diagrams or database approaches or previous design systems or like how to, how, how we ran a three day remote design sprint. Like those kinds of things are in the project toolkit. And so you’re not always starting from nothing. Like you are required to put in the time and thought to figure out how your team wants to work, but then you can also draw on previous successes to accelerate how things go. You know, once you’ve laid the track down, there’s a bunch of train cars that you can sort of take off the shelf and put on the track.

Gina: Yes. 

Chris: So you can get your train going.

Gina: Yeah. I think—I think that makes a lot of sense. Being able to look at that buffet at prior art and say, “Oh, how did they do this here? Oh, that’s interesting. That resonates with me. I’m gonna use that pit, that piece up. This doesn’t really make sense for this project.” it’s like, you know, you’re not starting, you know, from a blank page. 

Chris: Right. 

Gina: But you still wanna think critically like, “is this right for this client?” And this is something we try to hammer home all the time, “is this right for this client? Does this make sense for this client?” Right? 

Chris: Right. 

Gina: So every, every client in—and particularly at Postlight—like, is different. Different industries, different sizes, different funding models, all—all the different cultures. It takes that, that critical thinking upfront and throughout. You know, my hope is that giving that freedom and that autonomy and not being so prescriptive about exactly how we do our work, just encourages folks to show that initiative to become leaders and say..

Chris: Exactly.

Gina: …”I, this, this works, this works really well”. And look, we’ve had some PMs come in and say like, “I’ve run Agile. I, I’m like, I’m, I love agile. I like believe in the, you know, principles and, and these are, you know, this is some of how I like to work.” And they would kind of run it and the team, you know, some light or modified version. I mean, we often say that we’re like lowercase “Agile,” right?

Chris: Lowercase “a” agile. That’s right. 

Gina: Yes. The manifesto and the principles of Agile, absolutely 100% signed up. But the, the ceremonies and the and the story points, you just don’t, you don’t hear, you walk through the halls of Postlight, you don’t hear people talking about those things. 

Chris: Or if you do, it’s for a specific reason. Right?

Gina: That’s right.

Chris: Again, I think this kind of way of working has been so Positive for a client services company because we can meet our clients where they are, which is something we say all the time in so many different contexts. But if we’ve got a client who really connects with story points and understanding sizing and knowing how much they’ve got in the backlog or ahead of them, especially when they think about the littler things or, or big new features, frankly. And we’re working with, maybe we’re working with a few engineers on their side, and so working in a, in a more typical Scrum way feels really natural to them. Great. We can, we can do that. We can make that, But it’s, it’s a conscious choice, right? It’s more intentional than saying, Well, this is, this has been handed to me because this is just how we do things.

Gina: This is how we do it. 

Chris: Yeah. 

Gina: So I have, I have a question for you, and I actually don’t know how you’re gonna answer this when we talk a lot, so this is gonna be interesting. 

Chris: Bring it on. 

Gina: So before the pandemic, we—the, we were always a remote friendly company, right? But we, we always had our product managers and our product designers…

Chris: in New York City.

Gina: …in New York.

Chris: Yeah. 

Gina: Coming to the office. Right. And our engineering team was a split hybrid. Some in the office, some remote. And the pandemic, you know, forced everyone to work remotely. And during that time we started hiring our product managers and product designers remotely. Cause we were all remote anyway. And it opens up the talent market. The talent market was, it was a, it was a necessary move that we had to meet to make it. But before that, we had a pretty strong opinion, right? That product managers and product designers in particular should be in the same room and talking to one another, right? Because this, this autonomy and this freedom, it requires constant communication. 

Chris: Yes. 

Gina: And this like just being, being around one another and being near one another and being able to pull somebody into a conference room and put posts up on the wall. So I’m, I’m curious to know if you think—so now we’re basically completely remote. No plans for everybody to come back into the office. Right. It’s gone really, really well. I’m incredibly proud of the team. We have delivered really good work in this, you know, remote situation, even with product managers and product designers remote. But I’m curious if you think that this model of having more freedom, more flexibility, and more autonomy was harder with folks we’re hired and started and never had that like time together? And because, Right—cause we weren’t even doing like all company meetings. Was that harder? Was there friction and did it affect the way that we work? 

Chris: I think the answer is yes. I think it was harder. 

Gina: Yeah. The answer is yes. Right? 

Chris: Yeah. 

Gina: It was harder.

Chris: We’re human beings. We run off of interpersonal relationships. That is just the kind of animal we are. And I think it is objectively harder to build interpersonal relationships over a video screen than it is in person. That is, that’s just real. And I remember we, we hired our first remote head of product and she said, “When we get together in person, the value that I get from it is not getting work done. It’s being able to build those relationships so that when we go to do the work, we have some of those relationships in place that we can fall back on.” 

Gina: yes. 

Chris: And then once that is happen, If the whole team is distributed, it doesn’t matter because we’ve gotten really good at the mechanics of working together over video calls and slack and, you know, comments and pull requests and all the, like, these things are, are sort of normal and natural.

Gina: Right. 

Chris: But the team dynamics part of it, the like knowing and getting each other as people and, and because the best functioning teams have, you know, we don’t all have to be like best friends, but there’s a personal connection… 

Gina: Connection. Mm-hmm. 

Chris: …that is so helpful. And it just, it’s harder to do when you’re not in the same room. And I think it’s specifically hard for product managers and product designers when you are creating something new. There’s like this intense collaboration that happens.

Gina: Yes. 

Chris: At the beginning of a project. Or I, I would maybe put like technical architects in the same category where, you know, you kind of have to like bandy about a bunch of ideas that may be bad. If you’re meeting someone for the first time, like, you know, not literally the first time, but like you’re early in your personal history with this team and you’re trying to figure this out at the same time that you’re trying to get connected to them as people. It’s really challenging. And I think we took for granted that you meet someone in the kitchen and you start to like fill in the gaps because it just sort of happens when you’re in an office. I, I will say though, I don’t think it’s impossible. I just think you have to be much more proactive about doing it, especially in the beginning of a project, right? When we have a client project kickoff and the team comes together, we’ve tried to, to give them guidance to like spend time as a team first and figure out, it’s not just about how you’re working, but like who, what drives you and who you know, who are you as people and how do you make sure that you are connecting and supporting each other as best you can? And the teams that do that up front are far, I was gonna say more efficient, That’s the wrong word. Like they’re, they’re more in sync as the project work unfolds. 

Gina: Yeah, I totally, I mean, agree, right? And I think that you do have to be more proactive. You have to be more thoughtful about creating situations where you’re meeting, you know, you’re seeing one another, you’re talking to one another, you’re sharing with one another, and chat about things that aren’t necessarily about the work, right? Because if you build trust between one another, if he’s like, Oh, you know, you figure out what things you have in common. Maybe talk about some things that aren’t work. Like, like when that , you’re right, we’re, we’re wired for relationships and that that social connection, just when things are tough, And you’re like, Why isn’t this thing done? You, you, you’re just, you much more liable to give that other person the benefit of the doubt or to say like, I know you’re going through a hard time right now, or I know you have, or whatever it is. Like knowing one another as people makes doing the work, particularly in the stressful moments. Pre-launch is a very stressful moment. A bad meeting with a stakeholder can be a stressful moment. And if those relationships are there, the team is much more likely to weather it than all kind of be, you know in their own separate sort of spaces going like, ugh, this team. You know, it’s just, it’s harder to do when you’re not see, you know, running into one their, you know, it’s, it’s like they talk about the kitchen and the water cooler. Like that’s a real thing. 

Chris: It’s a real thing. 

Gina: So I agree that it’s not impossible, but it, it does, you know, it does require just more proactive, like, let’s hang out or figure out ways to connect with one another about the work, but also you know, about other things and, and feel like, Oh, like I, I trust you. I like working with you. We’re gonna get this done together. And that always leads to better outcomes. 

Chris: Yeah, exactly. It’s so important. I remember early in my career when we would have. Like big launches and we and the team would all stay late.

Gina: Yes. 

Chris: To like, you know, release something at 11:00 PM or something like that. 

Gina: That’s a big bonding moment. 

Chris: And it’s a big bonding moment. Exactly. 

Gina: Yeah. 

Chris: It should be it, it should be like, Oh God, I gotta stay late. And I have to, But I look back so fondly on those moments and think like, oh, that, those were like, you know, we were all in the ship rowing the same direction, like getting something across the finish line.

Gina: Yep. 

Chris: And it felt so good. And there’s, you know, yes you can do it on Zoom, but it’s not, it’s, you just have to be a little more intentional about it. And I think the best team, the best team leaders, and they don’t have to come from, you know, a product management or product owner title. They can come from design and engineering too.

Gina: Yes. 

Chris: Or content or community support. Like there, there are people who are about the connections between the team alongside the work that’s getting done and they will invest in them naturally. Like they will prompt those points of connection naturally. And it’s so, so valuable as teams are thinking about their, how they work together and what their dynamics are and how they align around whatever it is they have to do. 

Gina: Yeah, I mean, that’s a, that’s a pretty nuanced, I mean, I know, I know people who are, you know, really focused on their relationships with stakeholders and with their bosses and with their team. Right. But—but to be fostering the relationships between your team members, Right. And the dynamic in, in the room with your team, I mean, it makes a lot of sense, right? Because your life is a lot easier when folks are, you know, happy to see one another and, and are, are willing to pick up slack or whatever it is. But yeah, that’s, that’s, I mean, that, that, and now that you say, I hadn’t really thought about it, that—that way. But now that you say that, Yeah, I, I can think of examples where you had team leaders and, and leaders within the disciplines who pay attention to those things and try to foster those connections or create opportunities for those connections to happen. 

Chris: Right. If you take away the crutch of having the predefined, you know, workbook, and it’s like, I just gotta fill in the blanks on this workbook, and then I’m gonna be running my project, if you take that away, you have to fill it in with a different kind of intention and effort and approach. 

Gina: Mm-hmm. 

Chris: And I think the, the people who really connect with this way of working are the ones who will gravitate towards filling it in and saying, I, I wanna be thoughtful about my teammates, about how we’re working together, about how we align around what we’re going after. And sometimes that means embracing, you know, a, a component of a particular way of working. And sometimes it means really resisting you know? 

Gina: Right. 

Chris: Let’s not be too onerous about X, Y, or Z. And it’s, you know, when it—when it works, man, it is the best. Like, you just, you see the teams connect and go. Yes. And I, I’ve been a part of those teams and I see that happening, you know, across our company right now. And it’s, it’s fantastic. 

Gina: It is. It really is. I’m glad that we built a place that that’s, you know, that’s the, the success state versus just running, running the process. That’s right. I guess, I guess you could, you could, you know, say it, that’s the Postlight way. It’s more freedom and autonomy.

Gina: There you—you go.

Gina: And fewer, fewer predefined checklists.

Chris: Look at that. We had a Postlight way after all. 

Gina: [laughs] 

Chris: if you’re listening to this and you are thinking, I would love to figure out how to bring that to my organization. We don’t work like that. Or maybe you do work like this, but you want to find like minds who can join you to go achieve something big or take a big risk or, or make your next big jump with your platform. We would love to talk to you. That is real. We love these conversations. Even if it doesn’t lead to Postlight work for us. That’s okay. We just wanna talk to you. We are software lovers and we want to make a change in this world. People’s lives easier by making better software. So if you would like to talk to us, please reach out. I read these emails. Gina reads these emails. 

Gina: Every one! 

Chris: We’d love to hear from you. Please hit us up and we’ll, you know, if it makes sense to schedule a time we can even look at each other face to face. Or if you’re in New York City, then you wanna make a personal connection. We’ve got a great office where we’d love to host you.

Gina: Yeah, just stop by. 

Chris: Great. Thank you Gina. 

Gina: This is fun, Chris. Thank you. Trying to get back to work. Bye.

Chris: Bye.