Succeed in your first tech leadership role: learn from our journeys

[00:02:33] Welcome and Introductions: Tech Leaders Launchpad Livestream

Andrew Murphy: Welcome everybody to the first Tech Leaders Launchpad Livestream. This is an event where we're going to get together on a monthly basis and talk about what it means to be a tech leader, how we got into tech leadership and what we learned from that. I'm sure, like a lot of you, I made a bunch of mistakes early on in my leadership career. I learned from them. I became better. And I want to share my stories, but also the stories of the people that I know around the community and people who are passionate about sharing everything they've learned.

Today I have with me two very special people. We've got Allen and we've got Selena. They're going to join me on this journey of discussing what it means to be a tech leader. So what we're going to do is we've got a series of questions we're going to ask each other, but I really want this to be a conversation more than just a panel with a bunch of questions. So you'll see that we might not stick to the script. We might kind of talk over each other and have a good old fashioned yarn. That's perfectly fine.

There's also the opportunity for you to ask questions. If you want to ask us questions, stick it in the chat of wherever you're looking at us from, if it's LinkedIn Live or YouTube, and we'll get to those questions at the end. Feel free to ask them as we go through. I'll be collecting, curating and then asking them to our panel. So let's start off with a round of introductions and we're going to do one fun fact as well. So the fun fact I've chosen for this month is what was your first computer?

I'll start off with me first. So for those of you who don't know, I'm Andrew Murphy. I've been in the technology industry for almost two decades. At this point, I've pretty much been everywhere you can be. A software engineer. I started off as a ColdFusion developer working for government and I've worked in SaaS, products, consultancies and been in tech leadership for pretty much all my career. My first computer was, well, it depends whether you mean I guess PC or computing device. My first computing device was a Spectrum ZX81 which was an amazing computer using BASIC. My first physical, like actual, I guess Intel PC was 486 with a CO processor. Let's move on to Selena.

[00:05:08] Guest Introduction: Selena Small

Selena Small: Hey, thanks for having me. My name is Selena Small. I'm an engineering team lead at Fresho, aspiring CTO—watch out. One day retired professional kickboxer and I travel the world speaking at software engineering conferences with my friend Michael and our project Value Driven. My first computer... Not exactly sure, wasn't really into computers back then but the family's first computer was this big white clunky desktop machine running Windows 98. I'm sure there's a lot of familiarity with that. I was one of just two kids in my class at school who had a computer at home. But the first machine I bought for myself was a MacBook Air. And that was when I was about 26 and started teaching myself to code. So I came to the game a little bit late.

[00:05:59] Guest Introduction: Allen Hsu

Andrew Murphy: Nice. Thanks Allen.

Allen Hsu: Hi, I'm Allen. I'm an engineering manager at the Lookout Way, ex-interim head of engineering. We build software for care companies to run their businesses. Fun fact about me is my first computer was similar to Andrew as a 486 DX2 with the turbo button, and the first thing I did was try to get more memory off it by deleting everything. So I did a Dell Start Start and it wouldn't boot anymore. So yeah, that was my first experience.

[00:06:34] Tech Mistakes as Learning Experiences

Andrew Murphy: I've done that myself. My very first VPS that I had, like online hosted server, I accidentally fat fingered and I did RM RF/ instead of DOT slash and ended up deleting everything on the server. And because I'm smart, I did it with sudo which literally meant I deleted everything. Mistakes you make. We should, we should do a live stream on that. We should do a live stream on biggest mistakes that we've made because I've got so many to share.

So what we're going to do is for this particular live stream, we're going to go through a little bit of our journeys of leadership and the first leadership roles that we had and what we learned from it because I think people learn well from stories. Let's try and tell some stories of what it meant to us to get into that first leadership role and the mistakes we made from it. So the first question we're going to ask and answer is what was your first leadership role, Allen? Do you want to take us through yours first?

[00:07:39] Allen’s First Leadership Role

Allen Hsu: Yeah. So I have been in leadership for about four years and I was an engineering manager to begin with and I never actually thought being a manager was something I wanted to do, but it was kind of like a, let's give it a go. I made a career change into programming and development so it was a, it felt weird to be like I'm gonna do something that I didn't think I was gonna do. And so turns out I actually really liked it. And I really enjoyed the kinds of balance of problems that you get when you're doing engineering, management, and doing some engineering at the same time. So that was four years ago, and I really enjoyed my first experience. But there was also lots of lessons I learned.

[00:08:46] Leadership vs. Management

Andrew Murphy: Yeah, you know, everybody learns lessons. The fact is that you move into leadership and it's a different skill set to what you were doing when you were in IC, which just means there's a whole new place for you to learn and make mistakes and become better. It's a very, very common pattern. How about you, Selena?

[00:09:09] Selena’s Early Leadership—Hospitality & Sports

Selena Small: Well, I should unmute first. It's an interesting question. What was your first leadership role? Because it really depends on what you mean to be classified as a leader. You have to have followers or be paving the way, paving a direction. And loads of people make the misconception that being a manager is by default being a leader, when in fact, managing and leading are really two different things. Managing is more about organizing, overseeing processes, and leading is more about inspiring and motivating and influencing and culture and things like that. And it's interesting, Allen, you went straight to your leadership role in engineering. I want to go back a little bit further because outside of tech, I've got extensive history in hospitality management roles. Way back when I was 16, I was managing the burger bar, the local fish and chip shop where I grew up. And by my mid-20s, I'd been managing pubs and bars and restaurants and nightclubs. But, you know, the key to all of that is I was managing and I wasn't really a good leader.

So I guess that doesn't really answer your question, but sports have been a really big part of my life, too. I've always been really active, and when I was 15, I was appointed the captain of my school's girls first 11 soccer team. And I guess being a captain means being a leader. You need to rally the troops and you need to motivate and push the team forward. And that sports leadership has continued into adulthood. So I took up kickboxing and led as an inspiration to others in the gym there. But I'm guessing you're after something a bit more tech specific.

[00:10:48] Transition to Tech Leadership

Andrew Murphy: Not necessarily. I love where this is going because it talks to what leadership is, which is, you know, like I was saying, not management. But please, keep going.

Selena Small: But in tech, I didn't start as an appointed leader per se. I actually didn't even start my tech career until 27 after, you know, finally finding out what code even was and teaching myself to code. So it was my second job, where I currently work at Fresho, when I started feeling some of this leadership, some influence I was able to have. Almost immediately, I felt I was influential to the culture of the development team. I was one of the early engineers in the company, one of the few women in the development team. They asked my opinions, they took my feedback on board, and I helped influence some of the small changes. So I think technically speaking, I probably started leading in my career at that point. But we had a really senior team, really flat structure. There wasn't huge amounts of opportunity for managing people. But maybe three years in, I did start devising and managing larger projects. I actually influenced some of the projects that have led to teams that we have now. So I guess at that point, I was also really leading in my career, leading the direction of where we wanted to go with the product. And two years ago I was officially promoted to my first leadership role as engineering team lead, still at Fresho. That's probably more than you asked for, but there you go.

[00:12:31] Leadership Is a Mindset, Not a Title

Andrew Murphy: That's great. I love that discussion on the difference between leadership and management and how, like, you were leading without manager in the title. It made me kind of reflect on my first leadership role, and I was kind of doing the opposite. I had "manager" in my title, but I wasn't leading. It's because I didn't really understand the difference between those two things and the fact that being a leader is as much a mindset as anything. I made a bunch of mistakes in that first job because I didn't want to understand exactly what you're talking about there. I was somebody who was promoted to leader based on the fact that I had the most tenure as an engineer, not by dint of my ability to work with other people and lead them. I'm sure that's a very common experience.

[00:13:29] The Change in Responsibility and Experimentation

Allen Hsu: Just a minor aside... It is interesting when you're IC and feel you have more leeway to try things because when you have the authority, now you're like, "Oh hey, we're doing this now," and then everyone's like, "All right, boss says we're doing this." And it feels like you have less leeway to just try things that you don't know if they're going to work. When you're an IC, you can just try things and you don't have to follow me—it's low risk. One of the changes I felt in my first leadership, when given that title, was, "I better not mess this up, so I can't just make stuff up anymore."

Selena Small: Yeah, that's really interesting. You certainly, as soon as you are appointed as a leader, you now have more responsibility. You're answerable to somebody. You have to make the numbers work. You have to justify everything. Whereas as an individual contributor, like you said, you can go run an experiment and if it doesn't work, it's okay. It was just one person. We learned something from that. But it's not like this whole team has gone down the wrong path and, you know, we've missed our company OKRs or something.

[00:15:12] The Accountability Shift for Leaders

Andrew Murphy: Yeah, I guess there's that element of as an IC, you're only accountable for your own output, whereas as a leader, you're accountable for the outcomes of an entire team. There's just this change of what's expected of you that I don't think is discussed when you're passed that management hat. That's a great point. Which leads on to our second question: What do you think was the biggest mistake you made as a leader? I'm going to start off with this one myself.

[00:15:50] Andrew’s Biggest Leadership Mistake: Becoming a Bottleneck

Andrew Murphy: When I first became a leader, like I said, I was just handed the hat by dint of being the person with the most tenure in the team. I'd been there 18 months, as opposed to the people who had just joined there two months ago. So, you know, somebody had to lead the team, and it ended up being me. The biggest mistake that I made was I felt like I was being helpful by being the nexus of all information in the squad. I knew the codebase, I built this codebase. The people that had joined the company didn't know the codebase. So I thought I was being helpful by being there to answer all of their questions and being responsive to guide them to get to wherever they wanted to be in the codebase. But I became the crutch for them. I gave them fish rather than taught them to use a net and fish themselves. It got to the point where I couldn't even take a lunch break. Looking back, I see I wasn't empowering them to help themselves. I was being the solution to all of their problems instead of helping them come up with their own solutions. That was a very hard-earned lesson for me.

[00:17:34] Allen’s Biggest Leadership Mistake: Not Asking for Help

Allen Hsu: I think in my first few months, it was really hard for me to go, "Hey, I need help with this," and asking for help—especially with things like, "How do I talk to someone about this?" or "How do I say this thing that's probably hard to say?" Even asking that question felt like showing my vulnerability. It took me a long time to figure out that that's how you're supposed to learn, that's how you're supposed to get feedback: to say, "Hey, I don't know how to do this. I need help doing it." Part of the reason I was given the role was because they thought I could do it—being an IC, I could figure things out on my own. But in leadership, it wasn't that easy and I didn't pick it up quickly.

[00:19:06] Selena’s Biggest Leadership Mistake: Underestimating People Skills

Andrew Murphy: There weren’t that many great resources, you know, back when I became a leader, for me to find how to do this stuff. And I don't feel like we talked about it and discussed it as an industry as much as we do now. I resonate with that quite a lot. How about you, Selena?

Selena Small: I don't make mistakes. No, I can't speak so much to my current role because I'm still in it and haven't had a huge amount of time. But looking back through my journey and the various management and leadership roles I've had—especially management roles—the biggest mistake I've made is in a similar vein to both of you. I'm an excellent manager—very good with time, process, scheduling—but for my entire life, I've not been particularly great with people. As a child, I was a bit of a recluse. As a teenager, more interested in activities than the people doing them. As a young adult, impatient, even rude. Now, I feel constant self-doubt and social anxiety about what people might think. That could all be seen as a flaw, but the mistake was not realizing sooner the value that people have. Being a good leader is about creating culture and community—it's about the group, bringing their best skills and doing their best work together. Recognizing that is really the key.

[00:21:26] Technical Focus vs. People Focus in Leadership

Andrew Murphy: I feel like that's a very common engineer mindset. We're trained to think about process and systems, not people and how they fit into those things. My CS degree didn't train us to think about these things in a helpful way. This is a good segue to one of the questions we've got here. So Ashik asked, "Would be good to discuss how becoming a manager is not a promotion but more of a career change." How do we navigate this transition effectively? Selena, do you want to talk on that?

[00:22:33] Navigating the Transition: IC to EM

Selena Small: I'll have a go. Since I recently kind of... well, I'm still in the process. How do we transition from engineer to manager effectively? Very, very carefully. If you go from individual contributor to a purely management role, that's a massive jump—you're changing careers entirely. What I've done is move into a tech lead role, so it's 50/50: part-time IC, part-time EM. It's an intro to the management path, but not so far that you can't go back to IC if that's what you want. You're getting a taste. The biggest difficulty is time management; meetings suddenly take over, and you're thinking about multiple pieces of work at once. So, if you're still doing IC work, you need to block out good chunks of time for focus work, or those meetings will take over.

Andrew Murphy: Yeah. And that only gets more extreme as you progress. My last employee job was manager of managers, and the number of times someone looked at my calendar and asked how I get anything done… well, that's my job now. A vast majority is meetings, and only about 25% is conscious, focused thinking.

Selena Small: That's right. The leadership role is about empowering and encouraging others to achieve the things you'd have done as an IC. The transition can be hard because you don't get that instant feedback loop on your work anymore; it takes longer, so you need a mindset shift. As a leader, if your team does well, then you've done well.

[00:25:55] Leadership Success is Hard to Measure

Andrew Murphy: It's really hard to know if you've done that in any short period—such a good point. It's analogous in the IC world though. As a junior engineer, you're happy if your code runs. As a mid-level, you care about unit tests. As senior, more about well-structured code. The feedback horizon gets longer and the ambiguity increases. For anyone who's feeling a lack of success because of new success metrics, reflect that it's a progression, like you've felt before. As you progress as a head or director, how do you measure success for running large teams? It's hard to tell.

Allen Hsu: I think part of the transition is tooling. As an engineer, you care about how your editor is set up; as an EM, if you're not good at calendar management, it's not gonna work out. I was really bad at it at first. You need to show up and be able to prioritize, so that's the tooling of management. Coming from engineering, automate that, figure out what meetings are for, build those processes, and learn from existing EMs about their tools and processes.

[00:29:23] Building Relationships as a Leader

Selena Small: Having meetings and discussions takes up so much time, you need to find ways to make them efficient, but also make people feel valued—like they have a voice and are listened to. I spend a lot of time just having one-on-one chats with people, more than as an IC. At Fresho, we pair 100% of the time on code, so we get a lot of interaction, but now as a leader I talk to the CEO, CTO, other leads, people outside my immediate team—a broader network to help everyone bring their best.

Allen Hsu: Yeah, I can't stress enough how important it is to talk to your peers—other EMs, people doing the same job. It can feel lonely when you move into leadership, as if you're managing on your own. Pairing as an engineer makes things easier, but you don't have that as a leader, so seek out your peers.

Andrew Murphy: We do pair programming—maybe we need to find ways to do "pair leadership" sometimes. You don't want two leaders in a performance management chat, but there's a lot we can borrow from pair practices.

[00:32:25] Learning to Be a Better Leader

Andrew Murphy: How did you learn to become a better leader? How did you learn the pieces of advice you've just given? Allen, do you want to kick off?

Allen Hsu: I’ve been doing this four years. Not sure if I’m any better—it’s hard to measure. Early on, I felt good when I tried my hardest, even if the results didn’t land. But I had to take a step back and realize doing more isn't always effective. I had to learn to listen and ask for feedback—ask, "How do you think I'm doing?" or "Do you find these meetings useful?" People are willing to give feedback if you ask early. Also, I read, and practice is important—even if it’s hard to practice leadership when stakes are high, find lower-stakes ways to try things and get better.

Selena Small: Similar for me—it’s been trial and error, but a lot of self-reflection too. Consider what leader you want to be, look at others and decide who to emulate (and who not to!), be clear in your values. And talk to more people, especially mentors; I always try to have a mentor to talk things through, learn from, and sometimes just rubber duck.

Andrew Murphy: Yeah, finding community is so important—inside your org or out, peers or mentors. For me, teaching is also a way I learn: blog posts, training, teaching others. It forces me to get things clear in my own head, just like when I learned a new programming language by teaching juniors.

[00:40:01] How Technical Should You Stay?

Selena Small: I'm a team lead with five people including a principal engineer. With him in the team, I don't need to stay as technical, but he might leave and then the others may lean on me more. I work in a small company—18 engineers across three teams—tight knit, pair programming all the time, big on knowledge sharing. I try to keep a foot in the door technically to keep open the option of going back to IC work, but I do think I'm destined for management. Even at higher levels you can switch back, so how technical you stay depends on team size and organization.

Allen Hsu: Yeah, "engineering manager" can mean different things. Sometimes it’s very technical, sometimes it’s not. I’ve done a purely non-technical EM role, and now I’m in a 50/50 technical/management split. I like the balance of problem solving on both technical and relationship sides. Find the role that fits you.

Selena Small: Yeah, you can be a CTO at a startup and be hands-on, or a CTO at a big company and never write any code. I think I’d rather do just one or the other someday, but for now, being in both is a good way to find out what you like and keep your options open.

Andrew Murphy: The bad news is "engineering manager" can mean many things; the good news is you can find the flavor that fits for you. Technical doesn’t mean just writing code—it can mean architecture, build/buy decisions, influencing technology direction even if you aren’t coding every day.

[00:46:32] Mentorship and Support in the Transition

Andrew Murphy: When you transition to leadership, does your workplace mentor you or do you figure it out on your own? Allen?

Allen Hsu: I'm pretty sure Andrew's asking me because Andrew provides training for us. At our workplace, we now do leadership training for all managers and provide leadership resources—what to do in spicy situations, things to watch for, etc. It’s super helpful, so you’re not alone. There are heaps of resources online too.

Selena Small: It would be unfortunate if ChatGPT gave you better answers than Tech Leaders Launchpad! We don’t use external coaches or services directly, but we have an internal mentorship program so anyone at any level can ask for a mentor, and we try to match them up. In my role, I’m mentored by our board advisor, who has huge leadership experience. In smaller companies, if we hit a spicy situation, we tend to form committees or small groups, or bring in a more experienced leader for advice.

Andrew Murphy: External mentors can be very valuable—I've used them for challenging moments like layoffs and restructures. There’s no good way to do some of these things, but bringing in experience helps minimize mistakes.

[00:49:22] Leadership Traits in IC & Leadership Roles

Andrew Murphy: Scott McFarlane asks: What do you think are the key differences between leadership traits and behaviors in a non-leadership role versus what is expected in a leadership role? I think it's about leverage and force-multiplier effect. A principal engineer should have impact beyond their own code—helping squads, enabling others, etc. In short, it's about shifting from "one hour of your time = one hour of value" to "one hour of your time = much more value via others." It's a sliding scale—junior engineers might be net-negative at first, as they learn, but over time, responsibility and expectations grow.

Selena Small: You mentioned “non-leadership role” and “leadership role” as though it’s about job titles, but you don’t need a title to be a leader. Juniors can have big influence on accessibility or team practices. As you climb the ladder, you're just expected to inspire, motivate, and influence more—but these traits exist at all levels, not just in titled roles.

Allen Hsu: Empowerment is key—the biggest difference I expect in leadership roles is that you enable others to do things they couldn't before. Leaders have more impact on the environment, processes, and culture. An IC has a harder time changing the culture on their own; leadership roles naturally have more effect.

Selena Small: Interesting that you mention authority—being given a leadership role doesn’t magically make you a leader. You need people to follow, and you can achieve that at any level if you convince people and help them see your vision. Just having the title doesn’t guarantee you’ll lead; you still need buy-in.

Andrew Murphy: In many companies, unfortunately, the title does lend extra weight to your opinions and behaviors, even if it shouldn’t. As a leader, be aware that your actions have consequences beyond the immediate result—they set norms and have ripple effects in your organization.

Allen Hsu: Agreed. As an IC, you can experiment more freely. As a leader, your actions are watched for acceptable behaviors and values—they multiply throughout the team.

[00:59:16] Final Comments and Farewell

Andrew Murphy: I want to point out Alex’s comment—he’s had a lot of eureka moments today and he’s new to his leadership role. Alex, you’re on the right track! Join in, learn, and be a part of the community; you’re not alone. Thanks everyone for being here. This has been our first session on first leadership journeys and what it means to be a leader. Thank you to Allen and Selena, and everyone who participated and asked questions. We’ll be back in a month. Please send feedback, share what you liked and what we can do better. See you next month!

Allen Hsu: Thanks.

Andrew Murphy: Bye everybody.