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How do you find new leaders? Is it better to promote from within or hire from outside? Do former practitioners make better leaders? As Postlight’s CEO and President, Gina Trapani and Chris LoSacco ask themselves these questions daily. This week, Gina and Chris share their thoughts on how to spot leadership qualities and empower new leaders.


Cris LoSacco I don’t–it was a leading question. [Chris & Gina laugh] I totally agree.

[music ramps up, plays alone, fades out]

Gina Trapani Hey Chris!

CL Hi, Gina!

GT How are you?

CL I’m great! We’re back!

GT We’re back! We took over the show again. This is–I don’t know–this is gonna be a regular thing.

CL That’s right. More war stories about the exploding company that is Postlight the agency. [Gina laughs]

GT What is the word that you feel like comes out of your mouth the most when we talk about the team and the future of the company? And what we’re building here?

CL Leadership? 

GT Yesss.

CL Yeah. [Chris laughs] I think that’s the one.

GT We say leaders and leadership. I mean, also, look, our clients are also typically our leaders inside their orgs. They’re people who are responsible for some numbers, some teams or some big business goal. Leadership is, we talk about it constantly. And do we have the base of leadership that we need for the company to grow for everyone to be having good experience to feel supported and empowered and enabled to do their best work?

CL So if leadership is the most important thing, the paramount thing, how do you go about it? Like, I mean, we have this conversation a lot. I’m gonna play dumb for a second here. There’s a lot of questions when it comes to establishing a leadership team and a leadership structure, like, where do you find them? How do you make sure it’s effective? How do you have good communication both up and down the chain? Let me start with a question. When you’re thinking about minting a new leader, should you be looking at the people you have? Or should you be going outside?

GT I mean, this is a really, really great question. I mean, this is always the question, do we bring out from within? Or do we go outside? I think it’s every leaders job to be constantly sort of scanning the team and looking for those sort of tell-tale qualities internally, that lend themselves to leadership, and we could talk through some of those qualities are. I don’t think that everyone is that has those qualities is necessarily ready to take on, you know, traditional management leadership, which just means like, I have direct reports, and I’m, you know, responsible for them. Or if it’s, you know, in our context, in an agency, Postlight, we build stuff for our clients, you know, engagement, leadership, you know, to put yourself forward as the leader and the representative of Postlight to our clients. That’s another kind of leadership, there’s practitioner leadership, which is like, I’m a really, really, really good designer, you can see that and you respect that. And I have gained sort of implicit authority, because of just how good I am at my craft, I mean, there’s a few different kinds of leadership, but you should always kind of be scanning your team. And seeing those those potentials, who’s got those those little lights, you know, they get brighter over time, hopefully, right? That, you know, like, this is somebody who is ready to rise to more leadership responsibilities. But then, you know, going outside and bringing in an experienced leader who doesn’t have all the context and history and. you know, time inside your org that can bring in perspectives and experience from elsewhere, that’s also, it feels very high risk, because you’re like, I don’t, you know, it’s, I can make my best judgment in our interviews, but we’re gonna see how it goes when they when they arrive, but that–

CL It’s a new person.

GT But it’s a new person, exactly, and how are they going to mesh with the team. And it feels risky. And in fact, that was something that we were, Postlight, I’ll just be upfront, we weren’t so great about that. The first few years, we only promote a really from within, so the trust and respect was sort of built in to r&d leaders as we meant to them. But when you hit a period of rapid growth, which we did, particularly last year, you know, we needed to bolster our leadership team in a way that kind of really necessitated going out going outside. We hired a few key leaders from outside, they were big hires that felt very consequential, and we stretched we were like, okay, we think this is and it has gone very, very well with both.

CL I want to go back though, Gina. So you said, you should always be scanning your team to look for a certain set of qualities that would lead to one of those paths you suggested. Management, like having direct reports, or leadership either with a client, even at a product company, you know, you’ve got stakeholders, how do you, you know, orient around those stakeholders as a leader? So I’m curious, like, what are some of those qualities that you think you look for in those tracks? And where do they show up?

GT I think one of the biggest, most important qualities of a leader is communication, clear, consistent communication, that ability to connect with others, to put forth a message that aligns a group. I don’t know, they call them soft skills, which are think really like undersells them, yeah what does that mean? But that ability to create trust and to you know, relate to others and to feel like I’m I care about you, we’re in this together, and that is with a with a stakeholder or with a direct report, or with a peer, and I’m going to help you out. And having that there’s a little bit of an innate sense of like, like splitting up work being that good collaborator, knowing when to go in and say, I’m going to help and do this for you, and knowing what to say, like, I know you’ve got this, like, let me know how I can help. You know, just those dynamics, you can really see those emerge from from folks, I think as they as they progress in their careers. There’s another quality of leader and it’s like a little bit of a dirty word in our industry, but it’s managing up, like communicating to the executive team, like in a lot of scenarios, client engagement scenarios, we interact with very high level people at our clients, right? CEOs, CTOs, SVPs, and that ability to kind of boil down messaging to its core and making it clear and having a point of view and putting it in front of very senior people who haven’t been in the weeds with you every single day. That is a very particular skill set that I think you really develop over the years as you get more exposure to very senior people.

CL Yeah, so you’re not talking about just, you know, being really nice, or asking about their kids or whatever you’re saying, how do you do the work of editing and summarizing what’s happening day to day or week to week on a project with a group of people and bring it to an executive level person in a clear, concise way? And I totally agree with you, that is a skill, a distinct skill from doing the work. Because you have to think about, sometimes we say people, you know, they want to show that they did a lot. They want to, you know, they want to show–

GT Show the work. [Gina laughs] Let me tell you every single thing that I did.

CL Exactly, let me run down my schedule from last week, or here’s the 14 JIRA tickets that we addressed. And it’s like, okay, in some context, there’s value there. But what you’re talking about is something different, which is a level of, you know, almost analysis on the work that’s happening to say, here’s what you really need to care about, that is absolutely a quality of good leaders. And it is something that we sort of look for, especially when it comes to engagement leadership, because doing this for a client is invaluable. If you can make sure that you’re telling people, here’s what you need to know, in 10 or 15 minutes, as opposed to a two hour meeting. That’s gold for our clients. And that’s one of the things we offer to them as we do our work.

GT Absolutely, you know, risk, challenges, opportunities. Like I mean, look, I love you know, I think execs like love to know, the team was working really hard, and they did all the things. But that proof of work. In the end, all that that high level leader wants to know is like, did we move closer to our goal, exactly what we need to do next? And what should I be afraid of? I mean, like raising risks to, but in a way that’s not like, here’s this minefield of all the things that could go wrong. It’s like, you know, we’re doing this, we have a very strong point of view about why we’re doing this is the goal we’re going toward this is what we’re going to measure our biggest risk, you know, either or the assumptions we made the biggest race, we think is this, here’s what we’re doing to mitigate that risk. And we will monitor this and let you know, if it comes to fruition. 

CL I mean, you just said something very important. Here’s what we’re doing to mitigate this risk, that implies that that person has thought through not just hey, we need to be careful about something. But instead, we need to be careful about it in this way. And here’s what I think we should do to be careful about it. And that extra step, again, it’s a leadership quality, right, especially as we see people who are less inclined on that path. They’re just gonna say, we better be careful for X, and not think about the follow on, which is that I mean, it’s just as important, man, it’s more important, frankly, because you need to be able to mitigate the risk for it to be effective.

GT Yeah. I mean, if you’ve thought ahead of you, okay, like, here’s the rescuers what I think could go wrong. And then often, you know, you say, okay, so like, what do you think we should do about that? There’s some people will be like, well, you know, I don’t know, like this can go really wrong. Or then you have that person who goes, you know, I thought it through. So here’s what I would do. The thing about a leader is that they internalize the task, the team issue the client problem, like, as like, they make it their own problem. Like, this is not my problem. And if you know, like, when you go to the doctor, and they’re like, you know, well, this thing has happened, my kid, okay, well, you have these three options. I think it will if this was your child, what would you do? Yeah, what would you do? Tell me what you would do. That’s what you want to hear. And you can tell the difference. I think this is a leadership quality of the person who did take that next leap, and go like I thought it through and here’s why, if it were me, I would do this. And here’s why. That’s a really big one.

CL That’s a really big one. I think you said it perfectly before you got to constantly be scanning because you will see the signs when someone is going that extra step. If you’re looking for it, versus just, you know, saying this is risky, we need to watch out. It’s a key leadership quality. Do you think people management is different than the skills that you’re listing? And what do you look for when you think about minting a new people manager, someone who’s going to have direct reports for the first time?

GT Yeah, I mean, I think that that has to be someone who is genuinely interested in developing, you know, the career that I mean, in a way, they’re going to be the advocate the person at the table for their direct reports. They’re going to advocate for the direct reports, they’re going to see and raise risks with those, if there’s something bubbling on the team with their direct reports, they’re going to lay out a clear path of growth for that person. So for people managers, I mean, you know, we’ve had very senior people say, or people who are really on that trajectory, that leadership directory and say, I don’t want to manage others, like, I don’t want to be responsible for others careers, that’s a particular thing. It’s a big responsibility. I think that in those cases, the thing that I really look for is the person who understands, you know, like, what Postlight is trying to do, and the employees sort of experience that we’ve set up in order to do that, and is able to work with their direct reports, like kind of within those constraints and frameworks, and you know, the situation that we’re in, which is that we’re an agency, and we have clients, and there are particular things that come along with that, and create that good experience and create that growth path. And think about their direct report not as like a resource that they can allocate to a project, but like, as a human being on a path in their life, and in their career, who are trying to, you know, get particular motivations for to come to a certain job, what they’re trying to do, and how to find the alignment between what the company is trying to do, and what that individual is trying to do. So that we can, you know, be together in this space in 2022 to try to do a thing and like, enjoy working together. That’s really what’s needed. And that’s particular skill set, but that that, you know, the communication, that trust in that engagement and that empathy and like, you know, trying to take off your boss, well, sometimes you do need to be a boss.

CL Sometimes you do need to be a boss.

GT Yes, put on the shoes of your direct report and see it from their perspective and align them with the goal of, you know, what we’re trying to do in the business, that’s what I look for, that’s a hard thing. You see it in small ways here and there. Things come up between people all the time, and people speak to one another, peers, or collaborators, not necessarily a manager or something has gone wrong, or if they’re worried about something or something’s not going well. And you can kind of see the people who raise issues or bring something up or ask questions, you know, who really, like it’s resonated with them, and they want to, like, take the opportunity to raise it and say, like, what can we do here? What should I say? Like, what is Postlight’s position on this? How do we make this easier, better for our team, for our clients, etc.

CL I want to build on that most recent point, and also the word used before, align, I think that’s a hallmark of good management, is aligning what’s right for the person and their career growth and what’s right for the company and its goals. And I think that is easy to say and hard to do. It is a skill that you can, I mean, hopefully look for, you can certainly cultivate it. But representing the company is important for a manager. I think when you have direct reports, you have a responsibility to them, to make sure that they are on the path that they want to be on. But you also have a responsibility to the company. Because now you are the representative for what the company is doing and the decisions it’s making. And you know that is good and bad. And I think the best managers are the ones who can balance that really, really well. And I come back to that word align and sort of line up what’s best for the person and what’s best for the company. And it’s not always going to be exactly a Venn diagram where there’s no margin. I think sometimes it’s hopefully going to be in the 80 to 90% range, so that there’s a lot of overlap. And then the 10 to 20%, where there’s not overlap, you work with that person to say, here’s how we address the challenges. And I think the best managers are able to do that and navigate that really, really well. Again, even when someone is not a manager, you’ll see some of the signs that you can pick up if you’ve got a team because they connect with where the company is going and how to talk about it even amongst their peers or amongst their project team. They relate back to the company’s goals and where the company is going. And that’s a very critical sign I think and can be again, a great lead into a good manager is someone who can who can balance those two things.

GT You’ll see certain people step up to self organize, I mean, even if it’s just like an outing to the museum or a game night or in a more formal way, you know, an ERG.

CL What’s an ERG?

GT An Employee Resource Group. And we’ve got, I don’t know six or seven of them, actually just started doing these in 2021. And they’re groups of employees self organized around a particular issue, identity, thing in the world. And there are leaders of each of the ERGs, self selected leaders, often not managers sometimes, but often not, who lead discussions and start events and have conversations about you know, whatever the particular issue is. We have Women plus, LGBTQIA, caregivers or parents–

CL Immigrants.

GT Immigrants, mind, which is on neurodiversity. We have quite a few ERGs and that kind of voluntary, like these aren’t, you know, formal direct reports, but that kind of leadership, I’ve attended a few ERG events and seeing just the leadership of the organizers and creating a space to like spend some time together and connect in this way that isn’t right on a project isn’t around necessarily Postlight, but a shared experience or a shared concern. You see a lot happening there. I mean, those are folks, they are leaders, those aren’t just emerging leaders and they’re leaders in different contexts. But those are great, great signs.

CL There are ways to look at what’s happening today in your organization, whether it’s on a project team, in an employee resource group, like the ones you’re talking about, even in sort of casual interactions, like before or after a meeting or in, you know, non-project related settings, where you will start to see the signs, maybe their small surface and keep your eyes open. And as your team grows, you want to let those signs impact, you know, some of the decisions that you’re making when it comes to looking for the potential next generation of leaders and managers. It’s interesting, though, Gina, like, you can’t do that when you’re thinking about a new hire. So what do you do when you’re trying to interview someone? Right? We have an active role out right now for Director of Product Design, like it’s different, right? How do you try to approximate this when you’re interviewing or having a conversation with somebody for the first time?

GT Yeah, I mean, that’s a completely completely different thing. I mean, and that case, you’ve got, you know, 30 minutes, maybe an hour with this person to talk to them about, I mean, this is, you know, if you’re interviewing for leadership role in this particular role that you mentioned, we’re looking for seasoned, experienced leaders. So in that case, you’re, you’re want to understand what style of leader are you? What kind of leadership were you doing? And are you looking to do, always, in every interview, but a particularly leader interviews, looking at communication style and tone and just efficiency of communication. Like, is it clear? Are you explaining too much? Are you saying too little, there’s just that communication bit, but also how you think about your team and how you want to split your responsibilities, you know, outward facing, inward facing, people management versus practitioner? I mean, those are, I love interviews, because the stories that kind of people tell themselves about their career and what they’ve done and what they’re proud of, and what they want to do next, just, you know, tell you a lot and that word that you mentioned earlier that, you know, is there alignment here, is there a good match here, you know, at Postlight, and what we’re trying to do, what our styles are, and what our needs are, with, you know, where this person is at? It’s funny, we’ve done some analysis, look back at like reviews of candidates. And I always doubt that you can really have a full picture of a person after one or two interviews, you know? But first impressions, you actually learn a lot in that first conversation. 

CL It’s true. It’s true.

GT What do you look for when we interview leaders?

CL What do we mean, when we say leadership style? It’s how have you organized a team in the past? How have you done things like, you know, delegate to the people that are working for you? How have you set up growth paths for them? How have you, again, the things we mentioned before, right? How do you have you tried to balance the needs of the company with the needs of the person, like these are actually questions, you can ask in an interview and hear how they respond. And if you feel like, this person is going to really internalize where your company is going, and how to enable their team to feel connected to it. That’s a great sign. And you can actually sort of run and what I do, is I run scenarios in my head, like if we brought this person on, we invested, you know, a month or two in them to make sure that they get the Postlight sort of view on things. How do I think it’s going to play out? Do I think they’re going to feel really connected to it and feel like, okay, I can translate this to another group of people? Or do I feel like it’s going to be like, a constant negotiation, to get them to connect with what we’re doing and connect their team to what we’re doing. It’s a key metric that you have to try to suss out is, how connected are you going to be, you know, because you need your leaders to be the most connected of the company. And when you don’t have those small anecdotal pieces of evidence, you have to go on, how have you done this in the past?

GT Yes, absolutely. Another quality that I really try to index on and something I work on in my own leadership is decisiveness. I would rather have a leader who made a decision that was wrong and then at one point realized and backtracked, and then fixed it and went forward than a leader who was indecisive, or waffled or delayed or deferred. 

CL That’s interesting. 

GT And this is something that we practice just with our clients, right, we have to have a clear point of view on what we what to do next. You know, making decisions that we can move forward is so key to our work, because it’s so easy to just get caught in this swamp of well, like, we go this way, this could go wrong, could go that way that could go wrong. And there’s no easy answer here. I mean, here’s the thing, right, when you’re a leader, you know, there’s a decision in front of you because there wasn’t an obvious answer. Right. And sometimes, you know, it’s a clear calculus and you plug in the variables and you’re like, Oh, this is the clear winner, right? like those were the easy decisions. But the fact is the most decisions aren’t easy. Sometimes you got to make a leap, you got to make some assumptions got to fill in some gaps with, you know, a guess or an instinct. And that’s just the truth of it. And this is a truth that I think both of us face on a daily basis. [Gina laughs]

CL Every single day. But it’s real. I mean, and this happens in a big way, right, where you’re having a directional conversation about a product. And then it also happens in a very small way, where you’re like, you know, I have to make a call about this particular candidate, or a tool that we’re trying to use, or you know, these smaller things. And I totally agree with you, a leader needs to be able to–

GT Make a call.

CL Make call, use imperfect information and make call.

GT And there’s risk in that, right, like, there’s risk that you’re going to be wrong. And so you’re making yourself a little bit vulnerable, like, and this is actually a quality you can look at, like you can be in a meeting with this tough decision ahead of you, and you’re talking through, okay, we could do this, we could do that. And then they have that person who’s like, well, that’s not gonna work for this reason, or we tried that in the past. And it didn’t work. Like the person who’s shooting down every possible path forward. And then there’s that person who pipes up and says, I think we should do this. Like, there’s a risk that that thing will go wrong. But given all the options, like this is what we should do. They’re going on a limb, they’re putting themselves out there, and they could be wrong. And they might get a ‘I told you so’ later, right, but I vote rather index on that person. And when you’re whether you’re managing direct reports, or you’re leading engagement, that decisive effect clarity, like around that point of view, like I think that we should do this next, I think just earned you a lot of credibility, even if you’re not 100% right 100% of the time.

CL 100% agree. Let me ask you one more related question. We’re a technology company. We have product managers, product designers, engineers. Do you feel like the best leaders and the best managers were practitioners at one point, meaning an engineering leader used to program and a design leader had Sketch or Figma, or Photoshop or Illustrator–going way back now–open at some point, and they were moving pixels around? Or do you think that’s not as important? Do you think just being, you know, familiar with the practice is okay, and what you really need to over index on or just index on, or these other soft skills?

GT I prefer leaders who, if they’re not current practitioners, were practitioners at some point, particularly people leaders, because that experience of doing the work and understanding what that is, even if it was 10 years ago, when the world is pretty different. I think it’s important, I think it’s important from a credibility standpoint, I think it’s an important from an empathy standpoint, like I understand what your day to day job is. Now, I mean, this is an opinion, it’s a little bit–I have friends who have, you know, I have a close friend who’s a non-technical person who is managing engineers. And she’s like, I don’t have to know how to code in order to and she’s really good. So I couldn’t be dead wrong here. But this is my own bias. I think this is my bias, right? Because I’m a practitioner leader. And this is a lot of what Postlight does, is, you know, we’re all sort of practitioner lead rich, and Paul practitioners, right. So it’s kind of, we kind of base the company this way. So I could be wrong, but I do lean toward leaders who were practitioners at some point. And I mean, when you mint a new leader, you know, when we mint a new leader, internally, it’s typically not like a switch from like, I’m a coder. And now I’m a people manager, right? You don’t go from like, 100% time practitioner to 100% time manager. Now, I’m a manager part of my time, but I’m also you know, a practitioner. And so context switching, I think, is also an important difficult part of leadership.

CL It’s interesting that you reference your friend. And like, I wonder about other industries, where we don’t have as much direct experience. You know, it may not be as important if you are a claims adjuster, you know, that you’ve done claims adjusting before, and now you’re managing a team of those folks. I do think, though, I mean, when it comes to building product across the stack, you really can’t substitute–

GT Hands-on experience. 

CL And I think it’s certainly how we hire and what we look for, I mean, you know, full transparency, we’ve interviewed folks from outside the company who, who didn’t have a strong practitioner background for leadership positions before, and we passed. And it’s not because they, you know, necessarily couldn’t do the job. I just, I think, wouldn’t have felt right for us because, you know, so much of what we do is share our expertise with our clients internally and having someone who was a little further from it just never felt authentic.

GT Yeah, it’s a bit of a credibility thing, I should say aloud though, a great people manager is absolutely gold and that set of skills just because you’re a good engineer, or a good designer, or you know, a good product manager doesn’t necessarily mean that you’re going to be a great people manager. And I think we have seen this in in companies and in my career and our clients, like, you know, that person who’s just really good at what they do get promoted to lead a team and they’re just not they just don’t have those people management, those qualities or those skills, like they got promoted to a different job just because they’re really good at this other job, you know, and that’s a mistake to avoid.

CL Before we end I wanted to make this point that we actually have embraced a an alternate track in our growth frameworks across the groups, right engineering design, we want there to be an individual contributor role that is beyond lead, and you don’t have to manage. And that’s okay. Because of exactly the scenario you’re describing. There are people who don’t have that aspiration, and don’t connect to that. And that’s perfectly fine. And they can still be amazing engineers or incredible designers. And we want to enable that too. And so I think we would encourage, you know, everyone listening to also consider that, that like, you don’t always have to be looking for who’s my next manager, you know, can I make my superstar have direct reports? Because that might not always be the right answer.

GT Right. It’s true. It shouldn’t be one track play to those strengths, you know, play to the strengths. 

CL Play to the strengths. Well, this was great, Gina.

GT This is really fun. It was fun to talk about. It turns out that we’re hiring. [Gina & Chris laugh] I mean, I know this entire conversation has been about the fact that we’re hiring, we are hiring though, if you are a leader looking for something new, you should go to our site, it’s If you know someone, a great leader who’s looking for their next step in their career. I mean, look, if anything happens when you come to Postlight, it’s that you grow, I think you grow about five years in your career at about 18 months at Postlight. [Chris laughs] Because we have such interesting and varied work across so many different clients and industries. And it’s a hell of a place to grow and lead. And we have a lot of leadership to do here. 

CL It’s true!

GT So come join us!

CL It’s career rocket fuel. 

GT It’s true. 

CL It’s also worth mentioning, hiring is hard. And if you’re out there, and you’re trying to scale your group, and you’re having trouble, and you need help doing some of this or getting some folks in the building quickly as you look to hire the right person, because you don’t want to make a move on the wrong candidate. We can help there too. Reach out to We’ve had a lot of experience and success working with client teams who were on the precipice of scaling. And we helped them sort of get to that next level, and then figure out how to train them up as we exited. And we’re totally comfortable in that. In fact, you wrote a great post called ‘Building for the Hand-off’ on our site.

GT Happy to hand-off to your internal team once you gotta go. And for sure, yeah, get in touch. 

CL We’d love to hear from you. 

GT This was a lot of fun. We would love to hear from you. This is great, Chris. I’m glad we got to talk about leadership more. We talk about it every day. But now we got to talk about it with our 1000s of listeners. 

CL That’s right. Let’s do it again soon. [Chris & Gina laugh]

GT Definitely. 

CL Alright. 

GT Thanks, everyone. 

CL Bye y’all.

[music ramps up, plays alone, ends]