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Does leadership start when you’re made a “Head of” or as a bossy child? Postlight’s senior leadership team takes over the podcast for a roundtable discussion on leading and learning. Nathan (Product Management), Michael (Digital Strategy), Natalie (Product Design), and Aaron (Engineering) share the mistakes that have made them better leaders, how being vulnerable builds trust, and how they can spot the spark of a potential leader within their teams. 



Michael Shane Leadership is hard. Nobody’s perfect. We’re all people. You want to delete that? Should I stop that? That sucked, didn’t it? That was garbage.

[Intro music fades in, plays 10 seconds, ramps up.]

Gina Trapani Hello! Welcome to the Postlight podcast. We’ve got a very special episode to share today. Recently, our senior leadership team converged in our office in New York City, and they had an in-depth chat about leading product design and engineering teams.

Chris LoSacco We are thrilled with how this turned out and we are so excited to share their wisdom with you. So, have a listen!

GT Enjoy!


Nathan Henry Hello everybody. We’ve taken over the Postlight podcast. We are not Chris and Gina. We are discipline heads across Postlight. Let’s do some introductions.

MS Hey everybody. It’s Michael Shane. I’ve been here a couple times before, but I lead digital strategy at Postlight.

Aaron Ortbals Hey everybody. It’s Aaron Ortbals here. I’m one of our managing partners and I head up engineering.

Natalie Kurz Hi, it’s Natalie Kurz. I am the head of product design here at Postlight.


NH And I’m Nathan Henry, head of product management. So we wanted to talk a little bit today about leadership and we’re going to do a round robin panel with the group here. My first question, I wanted to kind of dive into a little bit more like, what’s your history of being a leader? Like when did you start becoming a leader? So maybe that’s just a soft entree into, you know, how you began as a leader. Michael, I’m going to put you on the spot first.

MS Sure. I suppose my first leadership experience would’ve been when I was working at Bloomberg, specifically Bloomberg media, which was two jobs ago. And the thing that sort of stands out there is leadership means really different things in different environments. You know, Bloomberg is a really big place. It’s a big corporate environment. There’s a lot of really smart, really ambitious creative people there. And I sort of arrived in a context of transformation and renewal in the media business, specifically focusing on digital platforms and digital audiences. And, you know, at one point in Bloomberg, I had 30 people underneath me and a couple of direct reports and that was like a very structured sort of corporate experience. And it’s totally different from the type of leadership that I’m doing now and that I’m working on, but I learned a lot of really valuable lessons there that I assume we’re going to get into, but I’ll let Natalie go next.


NK Well, I would say, I guess your question was my history as a leader. Well, I’ve always been a kind of bossy person. So I would say maybe like from the time I was eight years old, I started bossing people around and leading people. But from a professional perspective, which I think is more what you actually meant, I was thrown kind of into the ocean, I would say, as a leader. I really had no preparation. Basically just had someone who had faith in me and gave me a job as a director and said, build a team and learn all the things. I’d never managed clients before. I’d never managed people, I’d never hired and was just literally thrown into the deep end to figure it out. So I did that. [Laughs.]

MS I think a lot of us start that way, right?

NK Yeah. I mean, you know, there’s very little like, now I’m going to make you a leader. So let’s go through this preparation. I was just very observant of the people around me that I could model my behavior after. And honestly, I learned a lot of things not to do from those folks as well, and just failed a lot, went home angry a lot and learned quickly, and then kind of found the things that I was good at and tried to focus on those. But yeah, first year kind of walked around in constant fear, I would say.


NH I think that’s how you know, you’re doing it right. [Laughs.]

NK I hope.

MS Yeah. Well, you mentioned something. Aaron’s going to blow our minds in a minute, but you mentioned something really important which was about how much you failed. And I think great leaders have just as much, if not more failure, than success. Maybe you become a leader or are given opportunities because of your success. But I think you stay a leader because of what you learn from your failures or your mistakes. Failures is kind of an intense word, but everybody screws up. Everybody has suboptimal outcomes. [Natalie laughs.] And it’s what you do next that matters.

NK Totally agree.

NH Aaron, what about you?

AO So I’ve been with Postlight since day one, you know, since we started this place almost seven years ago. And a lot of my leadership journey has been here at this place. I’ve always been a practitioner, somebody that wrote a lot of code. I really like building things and Postlight, that’s really what we do here. We build stuff. And I started sort of managing, doing a lot with clients, early on at Postlight. And really again, we were a pretty scrappy team, a lot of people that really like to build things and like you, Natalie, I sort of, I had to learn my way. A lot of us learned management and leadership kind of as we went and sort of grew from there. You know, it takes time to learn these things and you make mistakes, but you’ve got to be open-minded and you learn how to deal with people. And this group is just a testament to that.


NH That’s great. My foray into leadership was not on purpose. It was very accidental and it was a training manager in a 9-1-1 center. I really enjoyed showing people how to do the job and be successful by doing. And that just sort of manifested into building trust with everybody that worked there. And eventually it almost feels like last person standing. And it was like, well, you should just do this now, since you’re here and everyone likes you, can you just show these people and like manage them? I was like, in my mid to high twenties, I had no idea what I was doing. No clue. And the job was a matter of life and death. And then you have like, responsibility to actual humans as a 20 year old. Like I did not know what I was getting into. So when Natalie said there’s a lot of mistakes there. Like, yeah, I feel that very, very much so.

NK Those are much higher stakes. I was, you know, managing websites for pizza chains and things of that nature. So, definitely higher stakes there.


NH But people still require any care, no matter what the job is. And so that’s the tricky part. But also back to Natalie, something that you said that was an Easter egg, I threw out because we’ve all well, Natalie didn’t, but Michael and Aaron lied to us. I bet we all were leaders way sooner than someone said we were leaders. Your story, Natalie reminds me of the first time I actually like took direction. I was five or six years old and I loved to play football. I loved to play tackle, flag football, but I had to be the quarterback because I knew the play that would win. And so I would tell people the route to run. I knew when to throw the ball, like for me, that was like the first time I could understand leadership. And so I want to go back to our friends Michael and Aaron and push you a little bit more. Natalie, I don’t know if it’s bossy. I think you knew maybe what you wanted. But Michael, when did you actually see a leadership skill? A lot younger than someone telling you were a leader.

MS Okay. This is legitimate leading of the witness. You know, my first career was as a classical musician and it’s from the time I was 13 until I was almost 30. That was my life all day, every day. And you have to learn not necessarily about leading people from a position of absolute authority when you’re in that world. But you have to learn how to bring people along and get them to buy into your vision. A specific example or a context for that would be chamber music, small ensembles. You can think of things like string quartets and things like that. These are 100% collaborative enterprises, and everybody’s got music on the page that was written by some genius, either last year or 250 years ago. And everyone has their own interpretation, but there are also constants that everyone has to agree on.


What are we tuning to? How are we going to set the intonation of our instruments? What is the tempo? How quickly or slowly are we going to play this? And in some cases it’s truly based on consensus and other cases, depending on the piece or the context, it really should be driven by one person or one instrument, but you have to find a way to bring the group with you that will still keep people invested and fulfilled artistically. I mean, that’s essential if you lose that buy-in in a musical context, there’s no way to end up with a successful performance by any measure. So now that Nathan has really expanded my brain and forced me to look back on this. I mean, I guess that would be true. And I had plenty of unsuccessful interactions in that context. I mean, I’m not afraid to admit that maybe more of them were unsuccessful from an interpersonal perspective than others, regardless of how the performances went. And I learned a lot about how to make people feel safe taking risks, how to get them interested in your point of view and how to have strong but productive discussions, especially around really subjective things. And in our world, there’s a lot that’s objective when you’re making software, but there’s still plenty that’s subjective and subject to opinion. 

I mean, one of the ways in which I lead that I think is sort of core to me and in my approach is rallying people around a standard. What is it that defines how we are going to do this thing? What defines strategy at Postlight, in whatever form that takes, whether it’s a proposal or it’s how we communicate with clients, what’s the standard that we’re setting for ourselves and how do we motivate each other to maintain that standard and be very consistent? I mean, that’s something that I took away from my time in music: risk-taking should be based on a foundation of fundamental mastery and capability. And that’s something that I try to communicate among my team and hopefully get people excited about learning and achieving. And I’m really fortunate that I have a team of amazing, amazing, impressive people that I get to work with. And I learn just as much from them week in and week out. So that definitely translated. But it’s something I’ve had to learn to temper. You know, I mean, I came from a world where if a single note out of thousands in an evening was out of tune, that was completely unacceptable. I also learned eventually how to transcend little things like that, but that was always the aspiration, was to begin from a place of flawless execution and then interpret, expand, go deeper experiment, take risks. What I learned is that it can’t be transferred one to one. When I first arrived in, in the world of business and I was in any kind of position where I had responsibility or authority—and Bloomberg was where I really first had that—you know, sort of going in and brow beating people or being absolutist about what was good and what was not, or what was acceptable and what was not, it doesn’t work. Certainly not consistently. And even if it does work, it’s often not worth the long-term costs.


NH That’s great. I want to hear from Aaron. And when you showed up as a leader, as some version of you that’s not today.

AO So I’ve always kind of liked to cut my own path for better or worse, where I think my passion for software, I would push in certain ways and in client services, that’s a double-edged sword. You can show up with a client and if you push them too far, that’s not great. But if you can help them, if you can really say, Hey, this is going to work better. I think my strong opinions in that way helped me sort of build leadership skills where , sometimes you overstep, you make a mistake, sometimes you don’t. But in the end we’re known here for accelerating timelines for people, and sometimes a little tenacity, a little pushing can be good. And having strong opinions around how software’s built has been sort of one of the things that’s helped me in my career, and you learn where and when to push and how far to take it. And in the end, if you’re aligned, you ship good things. And I think the people management side of things, dealing with humans, is kind of a different skill, but at least with software and having empathy for people around what you’re building, you can find the right path. And I think it always worked out for me. And I think a lot of people with passion in this business thread that needle, and as long as you’re a good person to work with, you like working with other people, you understand their perspective, it can work out.

MS You said something really important that I want to pull back out, which is that if you are aligned, you can ship really good things. It’s so important in every context, it doesn’t matter how brilliant you are or how right you are. If you’re not aligned with the people around you, if you cannot build some kind of agreement, even if it’s an agreement to disagree, you can’t ship good things.


NK And I want to bring it back to Michael, the whole analogy of music, cause I completely agree with that is I think that the mark of a good leader is kind of, you know, being that conductor, making sure everyone’s on the same page and kind of driving forward—it’s not dictating, right? But it’s kind of keeping everyone on the same page, keeping everyone at the same pace. And moving that part forward.

MS Yeah. I mean, I don’t wanna stretch the metaphor too far—

NK Do it.

MS But the greatest conductors in the world are the ones who have the greatest intuition for recognizing when they’re not the leader in the moment in the music. And I think the greatest leaders in all contexts are good at making other people leaders or helping turn other people to leaders either temporarily or permanently, depending on the context. And in our work, sometimes clients come to us and they’re already well-established, dynamic persuasive leaders and that’s one kind of project. Other times clients come to us and actually what they will need in order for their platform to succeed or for them to reach their goals is for us to ship the thing. But that thing is going to need a steward and is going to need a leader. And I’ve seen it happen in my career on projects over the course of months or a year or more, the person that we’re collaborating with or the team that we’re collaborating with blossom into new kinds of leaders because of the challenges that we go through over the course of a project. So helping others become leaders is the mark of real leadership in my opinion.


NH Well we’re going to get to that because that’s a lot of our work here is developing current and then future leaders. But we did tee up quite a bit of mistakes. So, we made a lot of mistakes to get to this point. And I don’t want to put all of our dirty laundry out there, but maybe we put some learnings together and share the biggest mistakes that we’ve made that helped shape us as leaders. And I’ll volunteer to go first since it’s a tricky question and I wouldn’t ask you to share without sharing first. One of the things that was really transformative to me is I lead Michael, a couple things that you said about consensus and alignment and getting everyone on the same page, that’s just naturally my skill and who I am. And so that transcends into my leadership style. So empathy is naturally there. I wanna find people where they are and help understand where they are and help move them to where they want to go, where they can go and where they should go.

And the first time that this actually caused internal conflict was the first time I actually had to separate employment for someone. And I went into that effort, making myself feel very divorced from the process because I didn’t want to be emotional. I didn’t want that person to have any sort of emotional tones because I knew that, you know, he wasn’t going to work here tomorrow. And so what I did instead of extending with empathy, and rather than being who I was, I had a brick wall. It was very business. It was very transactional. It felt very cold. And the process of doing that in itself is also just not fun. It is not good. It is not a positive experience for anyone in the room, particularly for this person who was being told that he wasn’t going to work here anymore, but I actually made it so much worse because I showed up as a different person. I changed exactly who I was to be not who I am. And, you know, looking back on that I could have definitely delivered that message in a way that also came from me genuinely. And maybe I could have supported him through that process better. It was never going to be a good thing or a warm thing, but that is something that I took that even when the chips are down and things are terrible, who you are as a person and who you are as a leader, that’s where that’s challenged. And that’s where you have to actually play into your strengths and make sure that you are leading with who you are, not who you think you should be at that time.


You’re in that position for a reason. You’ve made those mistakes to get to the level that you’re at. And so that’s something I think through a lot, not necessarily in terms of, you know, firing people that is not something I want to enjoy, but just making sure when it’s a stressful situation that I think about how do I lead? And just going back to brass taxes, to what are my skills in this, and making sure that those are the places that I’m leading with. I’m going to bring Natalie in next for maybe some mistakes.

NK No, that’s great. Because honestly, one of the biggest lessons that I’ve learned in my career was that you really have to understand yourself, your own strengths and weaknesses as a person, before you can be a great leader. And I kind of bring this back to, you know, starting out. I was a young woman in tech and I felt I had to act a certain way in order to be heard in the room, right? I was very aggressive, very brash, very confident at all costs. And that didn’t always work right? Sometimes it did. Sometimes it got me jobs, in fact. But I learned over the years that you can adjust that style and that demeanor to the situation to better serve as a leader in those circumstances. And there are circumstances when the personalities you’re dealing with are going to need a little different type of leadership style, right? Or the clients that you’re working with are going to respond to a certain type of personality. So understanding for myself, where I excelled at those things, where my weaknesses were, where I needed to maybe rely on somebody else to help me get through those parts, I think are really a key piece of being a good leader. I think the other thing I learned along the way is that leading isn’t about being right or always having the right answer.

NH That’s so true.

NK So again, it’s a lot of, I guess, self-reflection and understanding, understanding yourself, understanding the kind of leader you want to be.

NH You learn the most when you are wrong. If you’re right all the time, there’s nothing to learn.

NK And I think some of the people that I found to be the hardest leaders to deal with in my career were the people who were so staunch on, like, this is the right way. This is my opinion. There’s no flexibility. Do not challenge me. Right? Like those, aren’t the types of leaders that people typically follow.

NH Well, that’s more of a dictator than a leader. So we definitely don’t have that here. Fortunately.

NK No, definitely not.


NH Aaron, mistakes or things that you learned along the way that sort of paved you, you know, as the leader that you are today? You’re the leader of the biggest discipline here at Postlight. You’ve got the most sort of share of voice when it comes to humans and making sure that everyone is happy and feeling supported from the top. So you have a lot of extra pressure, I would imagine. So how did you get to this journey by making some mistakes along the way?

AO Yeah. So one thing I learned over the years is that you’ve got to really focus on trust with people that you manage and you talk to and giving just honest feedback. I think Nathan, you were talking about letting somebody go. It’s extremely hard. And as a manager, those are some of the hardest moments, the hard constructive, or negative things you have to deal with. And when you are in a situation like that, that person shouldn’t be surprised. And I think a lot of early managers, they make mistakes. And I know I’ve made mistakes like this, where you didn’t deliver the feedback soon enough, and you weren’t honest enough, you didn’t turn that something negative into a constructive, motivating thing for someone. If they’re struggling with something, you have to have a conversation where you want them to succeed. And they come out of something that started negative with, with a positive attitude. And it’s a really tricky thing to weave through and it takes practice.

NK Yeah. I think it’s so much worse to continue to let somebody fail, right? Than to have those tough conversations.

AO Yeah. And at Postlight I like to think we’re all super nice here. And it’s actually kind of interesting because there are places where people just yell at each other all the time. And what’s weird about that is it’s not great at all, but there’s an honesty to it. And so when people are overly nice, it can be also a challenge. You’ve got to find a way to strike the balance of sharing, honest feedback so your relationship with your team or the people you work with, or a client, you’ve got to be honest and you’ve got to push things forward. And it takes, I think, years to really master that stuff.

NH I think it’s continual also, and into something Natalie said, I’m thinking about positivity and delivering those messages. If it’s all positive, it actually begins to not mean as much as it should. And so the constructive criticism has to be there to offset all the positivity. Yes. Everything should be celebrated, but there’s also sometimes work that needs to be done or corrections that need to be made and getting ready for this podcast, I think about, you know, managing up and how do we receive messages and is it the clear direction that we need to hear as leaders? And so I want to dive into that for just a bit, like, how does your team deliver feedback upwards to you? I mean Aaron started talking about us delivering feedback, but what are places where we get feedback? And do you think that there is an honesty that comes up and back? Do we do that here, I guess is a very raw question. I will start with Michael.


MS Yeah. I mean, Aaron, you said the word trust, you were talking about trust in sort of giving feedback or maybe delegating and in order to receive good feedback from people on your team, they have to trust you. And as someone for whom trust in others doesn’t come naturally, it’s something I have to work on, I can say from experience that lack of trust is based on fear, as in if I trust this person and then it doesn’t go as I predict it will, I am afraid of what might happen. So the first step to creating an environment, I think where people will be truly honest with you is to show them that there’s nothing to be afraid of. There’s a couple of ways that I do that. The first is I look for every opportunity to raise my hand and say, oops, I could have done this better. Or, Hey, look, here’s an example. See what I just did? Look that could have been better. Or when someone improves my work, which happens regularly on my team and frankly is an essential element of our success, improving each other’s work. When that happens to my work, I celebrate it. And I think I do that probably at least once a week, if not more often. So I look for opportunities to show people that we are all improving and we are all on this journey together. And that creates an environment where hopefully people have trust, have reduced fear and are willing to be honest with you.

The other thing I think that’s important is to have reasonable expectations, especially for example, when someone is just joining your team, trust is not something that is binary. It’s not on or off. It’s a continuum and it’s gradual, and you’re going to start with zero or minimal trust as you get to know someone and it’s going to increase. So the other thing that’s really, really important is patience and to not rush it, which is another thing that I struggle with is rushing to answers, rushing to solutions, trying to get out of ambiguity or conflict as quickly as possible. But in doing that, then you can end up in control mode trying to wrestle a situation to the ground and not allow for any ambiguity or any dynamism whatsoever. So patience is also essential when you’re talking about trust with your team. You have to give people the time to build their trust in you, and you have to make sure that you’re taking steps to earn it and only then will they be comfortable telling you what you really need to hear.


NH Can I jump into that just one second? I think you have to continually earn it too. I think it can’t be oh, I’ve earned the trust and now, so now I’m done.

MS Yeah. It’s not a light switch.

NH Yeah. You have to continue to earn that trust. And there’s going to be times when misalignment happens or crisis or communication, you know, challenges happen. That trust meter’s going to go back towards the zero side and so you have to continue to work on bringing that back. And I think that’s the lens, without having that trust, you can’t deliver that feedback. And I think the better the trust is the more honest the feedback can become in both directions. Yeah. And I think it’s continual work.

NK And it’s hard to give feedback up, right? You think that there’s going to be punitive response, or they’re going to get mad at you or they’re going to fire you because you criticize them. So having that trust, I think is just the utmost critical part of that. I think another piece of that is how you receive that feedback. Right? Don’t get defensive, you know, acknowledge that yes, there were maybe mistakes made and I see where you can think that, I’m going to do better next time and then doing better next time. Right. So, taking that feedback and then taking action on it so that they understand that they were heard and that you value the feedback you got. One thing I like to do is at least once a year, if not more, kind of just send out an anonymous survey to folks that I’ve led, whether it’s in a project or a direct report and just ask them, what can I be doing more? What did you wish I had done more? And I’m fine making it anonymous. Cause I think people feel a little bit more at ease giving that type of critical feedback when they don’t feel like there’s any retaliation possible. But yeah, you know, that’s something I think as leaders you should always want to improve, right? Whether it’s your leadership skills or your practitioner skills or your client management skills or whatever collaboration, whatever it may be. But just asking others how you’re doing, I think is a key component of that.


MS And you may have to do it many times before they’re comfortable actually telling you how you’re doing.

NK Sure. Absolutely.

NH Here’s some questions that we use on the PM team. So we’re doing this. Like we have new managers. We have first-time managers, we’re growing the team. It’s a really great space to be in, but I want to make sure that the managers have the support and feedback to do better. So some of the things that we ask are, tell me about a time when you needed me to motivate you? What was the situation and how did I approach it? Meaning the manager, like how did the manager approach it. Tell me about a time when I delivered feedback. What went well and what could I have done better? So I’ll write about the feedback. And then another one is like, did I help you grow at the speed and in the way that you want and need? Really just trying to understand that we can calibrate that person’s desires. And so we’re using a mechanism to get to that feedback, which is super important.

AO I was thinking about this and building trust in a remote environment, which is actually pretty interesting. I think because Postlight’s engineering team has always been distributed. We’ve got people around the United States. I’ve been remote as a leader from Austin, Texas since the beginning of Postlight. And I think you’ve got to find ways to build that trust. And also we used to, we used to come to New York as a company and build trust in person a couple times a year and it can take a little longer remotely. And also people are different. Like some people are very naturally online and they can easily build trust through a screen. Others cannot. But I also think, with that, I think, correct me if I’m wrong, but I think the engineering team may be a little bit less vocal in some ways than the other disciplines just across the board on average. And so you really, you’ve got to make sure people feel like they can be a little vulnerable when they share something up. And again, to Natalie’s point, like there can’t be retaliation. The feedback has to be received. You can’t go off the rails. But really I think what we all want here at Postlight is to hear things that people want and people want to change and that they feel like they’re comfortable sharing it. And it can be a lot of times identifying the next set of leaders, people that are willing to share feedback and be honest.


NH Agree with that. And I think you said something that was actually leading right into my next question was over top of our disciplines we’ve identified leaders. We see current leaders that we have now and ones that might be in the future. And so, the other challenge is that we each have different disciplines. We each have different team sizes from somewhere, probably in the sixties. I’m imagining Aaron you’ve probably got some, some number in the sixties of team. Michael, you probably have a team of maybe six or so. So there’s a spectrum there just in terms of skill and also humans. So I’m wondering, when you think of your teams, what are the leadership qualities that you look for? That gives you the glimpse of, huh, I wonder if we can bring some of the characteristics out of these people to have them become leaders, to be able to depend on them in ways that benefit the whole team, not just their project teams or the work that they’re doing. And so maybe Natalie, I’ll start with you.


NK Sure. So for me, it’s definitely not about like titles or experience, right? Like those are pieces of becoming a leader, but mostly those are things that you get after you’ve become a leader, right? Or you continue in that path. You know, I think it’s about attitude. I think it’s about empathy. I think it’s about the ability to take ownership of things. Flexibility, I think is key. You know, I think to some degree, a skill in the craft when you’re talking about, you know, within the disciplines that we have is like, you know, I want a design leader to be good at design. That’s an important piece. Kind of bare minimum, I would say, but they don’t have to be the best at all aspects of design. Right? And being a good communicator. You know, I think two things that stand out to me is somebody who can be calm and mature in difficult situations. I think those people tend to stand out as leaders to me as well as people who just have good instincts. I think a lot of being a leader is just trusting your instincts, knowing when they’re right, knowing when they’re wrong and kind of being able to act in the appropriate manner to the situation. And sometimes that’s going to be led by experience. And sometimes it’s just going to be led by that instinct. So those are the kinds of things I look for.

NH That’s great. Michael, I happen to know your team probably more on a one-to-one basis just because they’re a smaller team and I’ve worked with all of them. Your team is made up of more across the board, just very generalization here, more senior practitioners across their fields. So I’m wondering if you see or spot different leadership traits.


MS Yeah, absolutely. To me, leadership is a set of capabilities and a sensibility that you grow into through your experiences. Leadership is what happens after you pass through a crucible. This is, you know, prodigies, in my opinion, don’t make great leaders. Prodigies are great performers, but they’re not great leaders. Leadership is a state that you reach through forging, for lack of a better term. And I think that’s an important thing in my experience. The other qualities that I look for in leadership is leaders are learners. Not all learners need to become leaders, but all leaders are learners, in my experience. So I look for a talent for learning, but also a passion for learning, which can be expressed in different aspects of life. It doesn’t have to only be about the work that we do or the discipline that you focus on at work.

AO Yeah. I mean, it’s really about identifying leaders and those instincts. It’s really important. It’s actually super exciting too, to see that blossom, as somebody grows in their career. And it’s really important for anybody’s growth, right? Especially here, you’re going to be given the opportunity to push it forward at Postlight. I was going to talk about something I’ve thought about a lot over the years, which is really leaders, especially experience leaders, the higher they go up in leadership. It’s about good decision-making. And I think part of this is instinct or rooted in instinct, but it’s, you know, as a leader, you have to make thoughtful decisions and ideally spend a lot more time on just making good decisions or giving good direction, less around like building things yourself. So it may be that you trust the team to build things, but they have a hard decision in front of them. All of us spend a lot of our time really just thinking about the solution to a problem. And we were just talking about this the other day, Nathan talked about when people come to us with a problem, ideally they come with solutions as well. And I think leaders, a lot of times, they’re providing solutions and leadership potential is a combination of seeing that right, where somebody has identified a problem and they need it solved. And they’re not just coming to you with the problem, they’re coming to you with the problem and a couple different ways that they can solve it well. It’s a really, really good indicator of somebody that’s on the right track.


MS You used that word trust again. And I think it’s also important to recognize that the more experience you get, the more you realize how much you don’t know. And I think one of the most powerful things a leader can say in any context is, I don’t know, what do you think we should do? And there’s a big difference between that and sort of a dereliction of duty or kind of throwing hands up and taking three steps back.

NK And being like, your problem.

MS Right. It’s a very important distinction. One pushes people away and one draws them in.

NK Yeah. I think that comes back to like, I think humility is a really important quality in a leader, right? As I said earlier, like it’s not about being right or always having the answers. Sometimes it’s knowing when to ask for help. And it’s knowing when to rely on the people around you. And it’s knowing when you need to do some professional development and increase your skills in certain areas.

MS Especially in our business where we can be in a different industry every three months.


NK Right. And skills are constantly changing. And I mean, I know that there are designers that are very young in their career that are coming in with way more knowledge about certain aspects of design than I’ve ever had. And I look to those people, I rely on those people to help teach myself and teach others around them.

NH Well, my last question is a fun one, hopefully. Where on your team, and not whom, but where on your team does leadership show up?

NK Yeah, I think for me, it’s I see a lot of it in folks who have a natural affinity for mentoring others, right? So oftentimes someone will jump on Slack and be like, Hey, can I get another set of eyes on this thing? Or I’d love to troubleshoot with somebody. And it’s the people who are like first in line that say like, yes, I would love to do that with you. I think that for me is a really key point of where leadership shows up. I think, oftentimes on projects, design is not necessarily the one steering the ship, but I look at designers who are leaders who kind of insert themselves in there, right? How can I help ensure success of this project? How can I help gain trust with this client and build that relationship? That’s a key point as well, of kind of being a leader within design. And then finally I’ll say just modeling desired behavior, right? Just being a good teammate and advocating for what’s right. And kind of taking the feelings and considerations of their coworkers into account. I think all of those things to me stand out as leadership qualities and the places that I tend to look for when I’m looking at leaders.


AO Yeah. So really in the end, all of this is to support what our goals are, which is building things and folks that make good decisions that help us build things better, maybe a little faster, maybe better quality, make a bigger impact. All those things are great. And a lot of times that helps rally the team, right? When you’ve got one person that’s really motivated, helping guide what we’re doing, then the rest of the team performs better. And then all of a sudden you’ve got essentially leadership on a project. And I think it’s interesting too, to think about our work and how projects require leadership, but we also have departments and teams that require leadership and they’re related and similar but different.

NH What you say is really important. Leadership, it isn’t just about being someone’s manager and giving them their reviews and checking in with them every week. Leadership shows up in who can figure out how to solve this problem, who can bring the team with them to solve the client’s needs. You said something like cheerlead the team to make the team rally around the unifying, you know, sort of north star to deliver that. And I think that’s where leadership can show up. It’s not just about, you know, managing people and staff it’s, How can you demonstrate leadership in your craft, your team, your emotional fortitude to sort of handle really adversity and bring people with you? Michael, where on your team does leadership show up in places where maybe you might not expect it?

MS So my team is one of the smaller teams at Postlight. Technically now we’re actually nine people, which is the largest we’ve ever been, but we’re still the smallest team at Postlight. That said, because of the nature of our work, both building relationships with clients and working with our teams after the clients come in the door, we are spread across the organization. And my team gets to work with everyone and where I have seen folks that work with me on the strategy team make the most impact or exhibit the strongest leadership is when they exhibit what I call generous equanimity. And by that I mean that regardless of the situation, regardless of the needs, they act with grace and poise and courage and with a mind to protect the standards we have to meet. But they do it for the sake of other people, not for the sake of themselves. They’re always looking out for someone else or another group when making decisions and taking action. And I’m thinking specifically in the context of working with our teams and our clients on projects, because that’s often where the most variability can occur and generous equanimity that can be produced on command in a repeatable way, in a reliable way. That to me is a sign of maturity and leadership.

NH Well, that’s incontrovertible.

AO Yeah. And our strategy team here, you know, they’re sometimes put right in the middle of the trickiest situations that we have to navigate. They’re gluing the client and the team together, and they’re dealing with challenges and it’s not an easy job at moments. And they have to, they have to really figure that out and the best of your team, which I like to think they’re all fantastic.

MS I like to think so too.

AO They do this over and over again.

NH I think the other part to note here is they’re in a situation—not to make this a strategy lovefest here. But Michael’s team doesn’t get the choice to say, I don’t want to work on that today. I don’t want to take that client call today. I don’t want to handle that tricky challenge today. They have to be ready to act immediately. And so that is leadership in and of itself, is just being there, showing up and defending their teams. Other places where things show up on product management is, for me, when people raise their hand to be like, yeah, I want to help, that’s leadership. And whether it’s welcoming a new PM to the team or reviewing a template that we might use for a kickoff deck.

MS Which to clear is the same thing as saying, I have trust, I want to take a risk. I want to put myself out there for the sake of others or the team.


NH A hundred percent. The other part where leadership shows up that I want to highlight is this happened a short time ago. Someone came to me and said, I made a mistake and I fixed it, but I want to tell you what I’ve done. And I thought that was really telling, because I didn’t have to know that it wasn’t a big deal, but they wanted to show with me how they learned, how they approached a problem. They made a mistake, they fixed it and it’s okay. It wasn’t a big mistake, but I thought that was so great to show that sort of trust being reflected back at me and that humility and that self-awareness to say, here’s a problem. I did make it better, but now I have fixed it. And here’s what we got to.

MS Whoever you are, we salute.

[Outro music fades in, ramps up.]

NH That is true. Well, thank you guys so much for your time. This was great to sit down.

NK Thank you so much.

MS Absolutely.

NK And you thought I was going to be the one that talked the most?


CL Well, that was great. Thank you to the senior leadership team here at Postlight. We love hearing leaders talk about leading. It’s something we do a lot at Postlight, so we hope you enjoyed it and learned something as well.

GT Postlight is a strategy, design and engineering firm and we’d love to hear from you. If you’d like what you heard today, reach out. You can speak to one of these leaders directly. If you’d like to send us a note to and we’ll see you next time.

CL Thanks very much.