Transcript

Gina Trapani On a daily basis I’m like, “Ok. The meetings are the work. This is ok. But yeah, we’re good. This is good. Should I be in this meeting? Maybe — maybe not. No, but there should be a meeting about something else!” [Laughs boisterously, Chris laughing along] 

[Intro music fades in, plays alone for 16 seconds, ramps down] 

GT Hey, Chris! 

Chris LoSacco Hey, Gina! 

GT How’s it goin’? 

CL Oh it’s going very well. How are you? 

GT I’m — where are — where are Rich and Paul?

CL Uh, yeah, I was gonna ask you! Don’t they usually host this podcast? 

GT I dunno! We had that all-hands later, first all-hands of the year. I don’t know, were they there? I didn’t see their little faces in the boxes! [Laughs, music fades out]

CL I don’t even know! [Gina laughing] It’s a new era for Postlight! 

GT It is! It is! New year, new us. No, we jus t— we kicked out Rich and Paul from the studio. Just for today. They’re gonna be around though. 

CL They love this podcast too much to completely disappear. 

GT I think they’re gonna be like, “Wait! There’s a Chris and Gina episode that we didn’t know about?!” We’ll surprise them! [Laughs]

CL [Laughing] Probably! 

GT [Laughs] Listen, I wanted to take over the show, for just at least one episode and we’ll show up in future episodes. 

CL Yeah. 

GT Cuz we had . . . a ridiculous 2021. I mean — ok, let’s just set the baseline: everybody had a ridiculous 2021. 

CL I mean, for so many reasons. 

GT Right, for — right, depending on how you define ridiculous. But Postlight had a wild 2021 and you and I, our roles at Postlight changed and looking back at it — and I didn’t really have a chance to, like, think about it until we had the holiday break . . .

CL Mm hmm. 

[1:33]

GT . . . there for a week, where I was just like, “What happened?!? Woah!” 

C It was a wild ride. I mean, yes, we took over as CEO and President and we’re thinking about how we, you know, continue to expand and grow but just in terms of, like, the number of people that we’ve brought on to the group, we went from— I think we started at around 60 or 70 at the beginning of the year, we ended . . . north of 110, close to 120, and we’re just on a— a sort of crazy trajectory and that has, you know, led us to think about— I mean, first of all, we had to figure out our own leadership style as we were taking the reins but then we also had to think about, ok, how do you set things up for this, you know, very fast growing company that shows no— no signs of stopping? But there’s a lot to talk about. 

GT I mean that 100 employee milestone was a big one. We hit it— 

CL That was a big deal. 

GT— in the fall. So, we essentially doubled in size from the beginning of the year to the end of the year, from like 60-ish to 120-ish. But that one hundred mark was big, I think— 

CL That third digit. 

GT— not only from— it’s that third digit! But there was a moment where— I mean, we’ve been— you know, we’ve been at Postlight for five, six years. You from absolutely day one and me, you know, I don’t know, nine months in or something. 

CL Very early on, yeah. 

GT And we were a small company where, you know, you’re 50, 60 people, you can keep everybody’s names in your head and, like, their locations, and you could name at least one of their pets or kids or their spouse— Like, it’s your circle of people and you know everybody in a certain way cuz it’s a small enough group and you’re in meetings with lots of different people but that one hundred number is when you’re like, “Oh! [Chuckles] We’ve expanded beyond the just casual see one another in meetings kinda size,” and it’s hard to— especially in a pandemic when you’re all remote, it’s hard to, you know, know people and necessarily have to develop out frameworks and processes and systems— 

CL Yes. 

GT— for things to happen because they don’t just automatically happen cuz it’s in everybody’s head because we’ve been working together closely, in small group settings, for a long time. 

[3:25]

CL There was a long period of this company where I, personally, was part of the interview process for every new person that came on. I was doing initial chats for product managers; I was sitting in a later stage for designers and engineers, and we’re at a place now where that’s just not tenable. Same thing with onboarding, like we should talk about onboarding because you can’t have every new hire sit with the founders or sit with the President and CEO to learn about the company, you have to codify some of these things so that when new people join because it’s — again, this blistering pace— there are things they can refer back to. 

GT Definitely! I mean, that was a big transition for me: not being involved, not interviewing every candidate, at least the more senior candidates it was— it was a very strange transition and you realize, like, I have to have leaders who understand what the business needs and is able to make these decisions, you know, and we have to all kind of be on the same page. And this is something that, you know, you very early on I think was like the first kind of few months that we were talking about our transition into our roles, I remember you said to me, “I think we need to establish a senior leadership team.” 

CL Yeah. 

GT And I was like, “Oh! What does that mean?” 

CL [Laughs] Well— 

GT Where did that come from? [Laughs] 

CL I mean, we have this very unique benefit because we’re a client services company where we get to see inside of all these other organizations that we work with and some things seem to work really well and you’re like, “Oh! I wanna steal that for our company.” And other things are like, “Oh God, we gotta make sure we’re not—” 

GT “Let’s avoid that.” 

CL “ — we gotta make sure we’re not doin’ that!” 

GT Yeah, don’t do that!

CL Yeah. Yeah. 

GT We can do an “oh” episode [laughs].

CL [Chuckles] Right, yeah, what not to do. But the senior leadership team idea— this exists at some of our clients. And it makes, I think, a lot of sense when you think about scaling responsibilities across a wider group of people and it involves more trust and more delegation than we had because once you establish that group, you have to empower them. You have to say, “Ok. You are our senior leaders, we need to orient around a common goal, and then you need to feel like you can make decisions within your sphere of influence to go after that goal.” And not everything can be, you know, decision-by-committee, or even decision-by-the-executive-leadership, like it— we have to agree on where we’re going and then the senior leaders have to be in power to go after it. And, you know, we always had a bit of that at the company but I think it got more formal, in a good way, when we sort of drew that circle around our senior leadership team. 

GT Yes. 

[5:48]

CL To go further on the, like, the delegation part of it: I think this was something that you really pushed, I mean, me and yourself to do more and more as we sort of stepped into our new roles is figuring out how to delegate and how to, rather than just doing the thing yourself, identify the right person to do it. 

GT I wanna talk about that delegation moment because that is, I mean, a big part of our transition is me being like, “What is this new role?” I think I ask myself the question, “Should I be doing this task?” [Laughs] Every day— 

CL 12 times a day, yeah. 

GT— maybe still but particularly in the beginning. What I really liked about the senior leadership team— and it’s very common, you see this a lot— We didn’t have it formalized. But, I mean, if you imagine our work chart is like seven lanes of groups that rule up to us and so we essentially drew a circle around the top layer and we made it a team, so it’s instead of it being like all the, you know, spokes on a wheel and everyone kinda came up to us and then we would go down to whoever else, it was getting our senior leaders to collaborate with one another in this much more— in this formal way, right? And being part of that team. And I [yeah] think that was huge. That was tremendous. And on some teams, we were like, “Who is the leader?” It forced us to decide, like that person and there were clear roles and responsibilities but we can say to our senior leaders, like, “Come together on these things and then come to us with your recommendations are,” versus it being just, you know, one-way communication between us and them which was— it was a big upgrade, I think, and I think in that our senior leaders were part of now a team, not just heading up a team. 

CL Absolutely! I think we should be transparent about the fact that this is still a work-in-progress. And I think that there are still— even today, there are areas that we’re identifying where we’re like, “You know what? We need to make sure that,” for example, “our digital strategy team and our marketing team are working more closely together.” [Yes] And so we have to sort of continually reinforce the idea that it is a team. That it’s not just seven distinct lanes that we have to sort of orchestrate from above. That’s probably the ongoing work of every executive leader, I think, is to continue to reinforce the team nature of all these groups. 

[7:52]

GT And empower people. Give them the autonomy to make decisions and make recommendations and, you know, have a point of view about what should be done versus just being like, “What should we do?” 

CL Let me ask you though, Gina, like, how do you empower— because this is hard for both us. I mean, [yeah] I know it for myself, I know it for you too. Like we, you know, we came from doing the work and I think our first instinct is to go in there and say, “Here’s what you should,” or, “Let me do this.” What— I mean, you said it before, asking yourself the question, “Who should be doing this for sure?” Are there other things that you’re like— you’ve implemented for yourself to delegate or to— to empower so that you’re handing things off? 

GT I mean, it’s such a hard transition from being that doer to the delegator, right? Like, both of us were— you know, started— you ran product, I was an engineering leader, like we were doing the work and it’s really hard to break yourself out of that mindset of like, “If I want this done right, I have to do it myself.” That’s not true, by the way, cuz we have incredible talent and I am often surprised and delighted in the best way about what I’m getting because it’s better than what I would’ve produced or it was a different angle [mm hmm] or brought context that I didn’t have. And so, I think, you know, this is— again, this is also a work-in-progress. I think that I’ve had to really examine and be like, “Is this high value? Who is the person who is like most, you know, uniquely qualified to do well on this thing?” Also, I just think that there are a lot of opportunities, there are, you know, stretched tasks, there are opportunities to grow when— you can give an opportunity to grow to someone else by delegating. And I still on some days can’t get outta my head that, like, the Pointy-haired boss cartoon [Chris laughing] where it’s just like, “Well, the bosses just hand out work to do and they don’t actually do any work themselves.” Like, because I— deep down I really love the grind and I want to roll up my sleeves and right the thing and sometimes I do, and sometimes I do it not because I have to and I don’t have the talent, cuz I love it and I want to and sometimes I just need to work out what’s in my brain.

CL Yup.

GT But the truth is, is that— I mean something that is just so incredibly satisfying is seeing our team and all the folks on our teams just rise and become those leaders and take on things that they even thought maybe were beyond what they could do, and succeed at them. And that’s tremendously satisfying and that’s really good— that’s really good for the business. 

CL Absolutely! It’s such a good point that you’re making and I think it is natural— I mean, I certainly feel it as someone who, you know, continues to grow into leadership, feeling like, you know, delegation is a bad thing and like, you know, it’s the caricature of the boss who just is pointing fingers and saying, “Do this thing, do that thing.” I would give one more concrete example that you suggested that I thought was really great which is a Help Desk. We established a Help Desk. So, for a long time, you know, many years of the company, the admin tasks just rolled to the partners. And it was like if you need, you know, your Google Workspace password reset, or you need an account on Miro, the partners were the admins for everything. So, you always had to go to a partner, and that time— I mean it’s, you know, five minutes here, ten minutes there, 30 minutes, but it adds up! [Yes] And it’s very high-value time. It is, you know, you’re taking— this is a hyperbolic example but, you know, you take time from a very important, you know, client relationship and you redirect it to managing Google Workspace, and it’s like, “Woah, what are you doing? Not the right call for the business.” And so we established a Help Desk where anyone can ask and as part of that Help Desk, we distributed admin responsibilities. We said, “Actually, department heads are gonna own some things; our office managers are gonna own some things; our executive business admin is gonna own some things.” And like, it required trust and [yes] letting go but it is much more efficient now. So when someone has a question it’s not requiring you or me or Erin, our head of engineering, who’s a managing partner, to go in and adjust things, you know, they’re able to handle it without us stepping in. And it’s a better experience for the person asking [yes] because they’re not waiting until you free up, or I free up, they’re [right] getting a much faster response because they’ve got more people on the ground. 

[11:55]

GT Absolutely. I mean, you give the team the chance to help each other and help themselves. It’s huge. I try to— I think we have to continually figure out ways to do that. Part of the reason why and something that’s been a growth opportunity for me is that— and our roles now— like, our job is to be thinking— like, looking at the horizon, not looking at the path, right? Like, we’ve been thinking two steps ahead. [Mm hmm] You know? Like we’ve been thinking ahead about, you know, strategy and where we’re going, like bigger picture things, and for me, like, it’s hard not to get kind of sucked into the grind of the day-to-day, you know, business. And so, it’s important— I’m thinking about what the COVID protocol’s gonna be, you know, the office the week before we all come back, right? But folks aren’t gonna be thinking about it until the night before. [Chuckles] I mean that’s a— [yup] that’s a very simplistic example. But that thinking ahead and having the headspace to think ahead, like those five minutes here and those five minutes there, “I’ll just do the thing,” takes away from that ability to kind of look— you know, look out over the— over the forest, I’m mixing bad metaphors [laughs]. 

CL [Chuckles] Look out over, through something or whatever. 

GT Exactly [laughs].

CL Yeah.  

[12:58]

GT Another thing that you— you had this vision when we were transitioning into our roles and the growth was so extreme that you were like, “There are so many systems I wanna upgrade at Postlight. Like the assistant meeting, the software that we use is falling down in particular ways, it’s only getting worse with every new person that we hire. And you were like— it was so great, I remember that day, you presented that deck to me, you were like, “Here’s what I think we need to sunset, here’s what we need to transition to, and it’s gonna be better in all these ways.” And it was very satisfying, I think really for both of us to [yeah] make sure that we were using great systems, cuz we love using great systems. Like, tell me about, like, how long had that been cookin’ in your brain?

CL A while. I think, in the back of my head. I’m a believer— I know you are too— tools matter. The things that you’re using on a day-to-day basis has a real effect on not just how effective you are in your work, but like how happy you are in your work, and how you sort of show up to things day-to-day. This is not a new concept, and I think it applies pretty widely, actually. I think it applies to, you know, your personal life as well. But I think it appl— you know, when you’re running a project team— I’ve made this point before, I wrote about it on our blog. The team needs to care about its process almost as much as it cares about the work it’s doing on the product. It’s not the same time investment, but you do need to take care of how you’re working alongside or even before you’re actually doing the work. And so when it came to, you know, thinking about how we upgrade the company systems, I saw pretty quickly, like, we need to make better choices with the tooling we have in place as we go from— again 60, 70 people to 120 plus. So like our expense software should be better. The way that we, you know, have company documentation. Like, that needs to be cleaned up and well organized and it shouldn’t be a question in people’s minds when they come in like, “How do we, you know, take PTO?” Like, that should be really clear. And it should be in a system that doesn’t require, you know, 14 hoops to jump through to administer permissions. We should have a really good payroll system with good benefits and that stuff— you know, know one wants to, like, spend the time there but you should. You don’t wanna over invest. You don’t wanna spend, you know, countless hours, like, inventing and reinventing how to do paytime off tracking, for example. [Mm hmm] But we do wanna think about how are we setting ourselves up so that we’re not experiencing these small moments of pain, like, every day? That’s what I wanted to do, that’s what we talked through, and I think we’ve done a bunch of them. And there’s more to do. For example, our annual reviews process last year, we used a tool for the first— you know, we had been doing it like everybody else does with Google Forms, Google Spreadsheets [laughs]—   

GT Spreadsheets! [Laughing] Yeah! Docs! 

CL Duck taped together. 

GT Yeah. 

CL And it was fine. But like it wasn’t great and this year we used this tool called Culture Amp— 

GT [With Chris] Culture Amp. Mm hmm.

[15:52]

CL — and I don’t know that Culture Amp is a perfect piece of software but it’s good. And I think it had a much better experience and, frankly, was easier for our people ops team to administer. 

GT Right, it was purpose built and it was easier to administer. At this point it wasn’t like, you know, seating at the wedding, like figuring out who is peer reviewing who was in the past— 

CL That’s like a mini job!

GT — for a person, yeah, in a spreadsheet, trying to match people up and Culture Amp did all that for you.

CL Yeah, and I think this is gonna be something that is gonna be ongoing for us. We don’t wanna drown in process cuz that’s a fail on the other side but we don’t wanna be so process-averse that we’re not thinking about, “Ok, how do we make sure that things are running smoothly?” And upgrading the things that need to be upgraded on a month-to-month or quarter-to-quarter basis. Another thing that comes to mind is the employee survey, which we ran for the first time which was suggested, actually, by Vicky, our head of product, who’s fantastic. And she— she caveated by saying, “Listen, we’re gonna learn some stuff that we might not wanna [chuckles] learn, so we need to be ready to respond to it,” but I think we were! We were ready to respond to it. I’m curious if you have thoughts about that whole process and how that went and— 

GT The suggestion of the survey blew my mind at first because, again, I was like in a small company mindset but realizing at a hundred people, one person’s response to an employee engagement survey is one percent of the responses, like because— It’s funny cuz Vicky, who’s been on the show before and is fantastic— she has been in an organization that grew— that experienced rapid growth and she was like, “Look, we’re gonna ask specific questions about employee engagement. You know, we’re gonna look at the numbers in aggregate; the results are gonna be anonymized in a certain way; we’re gonna see trends.” And I, like, I did a little bit of a double take at first because I was like, “We don’t have enough people to really see good trends in aggregate.” And that wasn’t true. Like, I was wrong and I was so glad that we did this survey because we really did, you know, it’s sort of a measure of sentiment around particular areas of employee experience and employee engagement and the feedback was really useful cuz we got to make decisions, you know, about what we wanted to change and do; what we should focus on; and what folks especially felt like they weren’t hearing about from us in the all-hands; and what people cared about that we could address better. It was very actionable feedback so I was so glad we did the survey. I, again, had to shift my thinking from like, “We’re not a 45-person company where I’m gonna hear what people are thinking and feeling just in the course of meetings and interacting,” right? Like, I mean, I would love if that were true but there are some folks— You know, we’re big enough now that there are people that I don’t interact with, you know, on a personal level on a daily basis, and I’m just not gonna get that— that feedback. 

[18:24]

CL I mean, I think this is something to take away for, you know, people who are out there who are listening; who are in a similar situation where you’re at this inflection point and your team or your org is growing past everybody knows everybody to having to operationalize a bit. And, I think doing something like a survey, it can feel a little alien. I don’t, you know— 

GT “I’m gonna make people fill out boxes!” This was— I worried about, “Ah! I’m gonna make people fill out TPS reports and it’s gonna feel really informal and big company and bad!” 

CL Me too!

GT And so many people not only feel— you know, checked the box but then opened the, like, “Add comments” and typed in in their free form [chuckles] text box and added more information. 

CL It was great! 

GT People really were engag— you know, very high response rate. 

CL Yes! We had a very high response rate and our people ops team diligently, I mean, they went through every single response. We talked about it, again coming back to the Senior Leadership Team, the SLT, we talked about it with the SLT. We [yeah] said, “Here are the things we’re gonna take action on.” You know, at the next all-hands, the company all-hands, we presented back: “Here’s what we heard; here’s what’s going on; here’s what’s not going so well; and here’s how we wanna address it.” And I think it was really positive and we’re gonna do it again this year too. It’s one of those things that, I think, we, again, we were a little hesitant about making that jump at first but once we did, it was worth it. 

GT It was definitely worth it, I’m glad that we did it. And I think we probably— we might even do it more than a couple of times this year, even just see trends over time. 

CL I mean, there’s a lot to talk about here. Maybe we could regroup again and talk— You know, this theme of formalizing and writing down things that have been ephemeral, it’s a big theme in something we’ve addressed— we’ve encountered in other places. 

GT Yes. 

CL As the company has grown. Maybe we get together again and, you know, shove Rich and Paul out of the studio [Gina laughing] and do an episode on that, what do you think? 

[20:09]

GT Yeah, I think we should do that. I think we should do that. I also wanna be totally upfront with everybody about just the challenges of like practitioner leaders and when makers become managers and sort of that transition on your team and in yourself and, just, in general, it’s tricky. And it’s part of career growth, it’s an important part of career growth but definitely on a daily basis I’m like, “Ok, meetings are the work, this is ok. But yeah.” 

CL Yes. Well, this was great, Gina. You’re gonna be hearing more from Gina and me as the year goes on and as we take Postlight [outro music fades in] to new and exciting heights. In the meantime, you mentioned career growth, we’re hiring. Are we hiring? 

GT We are so hiring. In 2022, we’re gonna continue on this trajectory and continue to grow. You should go to postlight.com/careers. We literally are hiring in almost every group in the company because we had a great year, we’ve got an incredible portfolio of clients who are just building big platforms that have tremendous impact on the world and, yeah, you should come check out postlight.com/careers. You should send it to your friends who are, you know, looking to come and grow because people come to Postlight to grow, [chuckling]  both clients and candidates. And, yeah, it’s a lot of fun! Let’s kick Rich and Paul out of the studio again soon cuz I wanna talk more about writing things down; I wanna talk more about leadership. It was a great year, this was a big transition for us. I so enjoy doing it with you. This is just the beginning, I think, I think— 

CL I’m having a blast. 

GT — and it’s a lot of fun and I feel incredibly grateful to have this kind of platform on this show and our team and yeah, looking forward to doing this again. 

CL Onward.

GT Get in touch with Postlight: hello@postlight.com. Hope to hear from you soon.
CL Thanks, everybody [music ramps up, p