What Stops Us From Taking a Leadership Role

Guest: Jean Hsu, Engineering Leadership Coach

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Have you been in your current role for a while, and are eager to try something new? Perhaps you’ve thought about transitioning from being an individual contributor into a leadership role, but you’re not sure if it’s the right move for you? You might worry about being qualified enough, leading people, being an authority figure, and what your day-to-day will be like. While it sounds exciting and maybe a great opportunity to grow, you worry about your existing skills getting rusty.

Well, all this month on Build, we’re going to be exploring the tradeoffs that aren’t talked about when we choose to transition from being an individual contributor to a leader. In today’s episode, I’ve invited on Jean Hsu, who was formerly an Engineering Manager at Medium and is now an Engineering Leadership Coach.

Here’s what you’ll learn in this episode:

  • why our perception of who or what we think it takes to be in a role is often wrong, and why we are more capable of learning and growing in a new role than we realize;
  • when it comes to leadership, it’s OK to take time to discover your own style; and
  • why the comfort and well-defined nature of our current role makes a transition harder and make us feel less accomplished in the beginning.

Once you’ve watched today’s episode, Jean and I would like to know: have you recently done a transition maybe from being an individual contributor to a manager or a leader? What were some of the concerns you had, and how did you go about handling that transition? Let us know in the comments below.

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What Stops Us From Transitioning Into a Leadership Role Transcript

Poornima Vijayashanker: Have you been in your current role for a while and maybe you’re considering a transition from being an individual contributor to a leader, and you’re not sure if it’s right for you? Well, in today’s Build episode, we’re going to explore some of the tradeoffs that aren’t talked about, so stay tuned.

Welcome to Build, brought to you by Pivotal Tracker. I’m your host, Poornima Vijayashanker. In each episode, innovators and I debunk a number of myths and misconceptions related to building products, companies, and your career in tech. Now one myth that I came across early in my career was the transition from being an individual contributor to a team leader. I struggled with this transition because I worried about my skills getting rusty and whether or not I had the skill set to actually lead people. So if you’re grappling with this, we’re going to cover it in today’s episode. To help us out, I’ve invited Jean Hsu, who is an engineering leadership coach. Thanks for joining us today, Jean.

Jean Hsu: Thanks for having me.

Poornima Vijayashanker: Yeah. You and I met a couple months ago at a event. I’m really curious to know a little bit more about your background. If you can walk us through what drew you into tech and ultimately led to what you’re doing today.

Jean Hsu: Sure. I went to school for computer science. I actually went to a liberal arts school. A few years in, I started trying to figure out what I wanted to do and what I really enjoyed was the coding and the projects and the—I didn’t really know anything about applications, what the applications were going to be, or what software engineering was as a job, but I really loved the classes. I think that when people talk about how to attract women to tech, a lot of the conversations are actually, they don’t seem as relevant to me because I really loved the actual coding itself, and I didn’t know anything about what I would do after I graduate.

Poornima Vijayashanker: So where did you land after college?

Jean Hsu: I had interned at Google the summer before I graduated, and then I ended up taking a full-time offer at Google that started right after I graduated. I moved up to Mountain View and I was there for about a year and a half. Then I quit and wanted to see what else was out there, and kind of had the sense that Mountain View and the Google campus is a little bit of a bubble, and so I started to dabble in Android development. I ended up at Pulse and did some of the Android development there. Then after that—I was there for about a year and then I ended up at the Obvious Corporation, which later became Medium. I worked on their first prototype. Then I was there for about five and a half years.

Poornima Vijayashanker: Oh, wow.

Jean Hsu: And then I left about six months ago.

Transition from engineer to engineering manager

Poornima Vijayashanker: So what catapulted you to strike out on your own?

Jean Hsu: It was kind of the right time to make a big change. I don’t know if it’s like, I have two kids. I have an almost two-year-old and a four-and-a-half-year-old and that’s very, it’s not stable, but there’s sort of a monotony in taking care of them. I had been at Medium for five and a half years, so I think there was a part of me that just really wanted a really big change and I was ready to kind of jump in the deep end again and figure something out that was completely new to me.

Poornima Vijayashanker: Now when you’re at Medium, that’s when you did your transition, right, from being an engineer to an engineering manager.

Jean Hsu: That’s right, yeah.

Our perception of who or what we think it takes to be in a role

Poornima Vijayashanker: What kind of prompted you to even consider this transition? Because a lot of people just think, “I’m happy kind of coding away. Why rock the boat?”

Jean Hsu: Yeah, I mean for me I was pretty happy coding away, but I think I wanted to see where I could be more impactful. I don’t know that I really chose it for myself. I was sort of, I wanted to have more impact and influence. Sometimes I was stepping into tech lead or project lead roles. I think at some point it was like everyone kind of knew that this was kind of the path I was headed and I was almost the last person to know. It was interesting because when I made that switch and started to take on a few direct reports, I think everyone was like, “Oh, it should have happened like a long time ago.”

Poornima Vijayashanker: What do you think they saw in you that maybe took you a while to see in yourself?

Jean Hsu: I don’t know. I guess I didn’t really know what a manager did. Even at the time at Medium it wasn’t called manager. I think they still call it a group lead, so it was very much this mentor, advocate, coach role, which is sort of, what I’m doing now is very similar to that. I think it was that people saw that in me, that they felt like they could talk to me about things and that I would help them solve their problems. I was never very much of a command and control, top-down type manager, which is maybe what I thought managers did.

Poornima Vijayashanker: Yeah, so maybe it was your perception or, “My misperception of this is what a manager is, so clearly I’m not a manager because that’s not what I want to do,” when really you’ve naturally been doing a lot of great tasks or I guess things that managers would do.

Jean Hsu: Right, yeah, like when you, if you ask me like, “Oh, do I want to help people and support them and help them solve their problems,” like, “Yeah.”

Poornima Vijayashanker: Right, but not maybe the “I want to enforce strict process or—”

Jean Hsu: Right, like I’m just going to tell you what to do every day.

Why we think we aren’t capable of leading

Poornima Vijayashanker: Got it. Tell us some of your concerns, then, going in, aside from this “I don’t know if I’m capable of being a manager or what a manager role entails.” What were some concerns with that?

Jean Hsu: I mean my transition was pretty gradual. But as I got more and more in it, I definitely had this concern that it was too early to go 100% in that direction.

Poornima Vijayashanker: Why?

Jean Hsu: I mean I think a lot of it is the tech industry. I sort of have this sense that people who don’t look like me, specifically white males, if they are, they look young and they’re in a management position, people tend to give them more the benefit of the doubt and think, “Oh, that’s someone who is like so talented that he got promoted into management.” I sort of worried the opposite would happen to me where people would look at me and say, “Oh, she doesn’t even have that much technical experience,” or like, “She looks really young. She came out of a boot camp,” or something, whereas I really had like a decade full of experience. I definitely had that anxiety of how will I be perceived once I leave this company.

Poornima Vijayashanker: And how did you handle that perception, kind of get over it?

Jean Hsu: That’s a good question. I think that a lot of it was sort of—I mean I also had the sort of struggle of do I then count as someone who’s like nontechnical anymore. You see these statistics of like, “Oh, 70% of women leave their technical roles.” I’m like, “Am I contributing to that?”

But I think what I landed on is sort of like the whole point is that you should be able to do what you feel, like is your calling, and that you want to do and not that I’m contributing to the statistic that we want to go down, not up. I think that’s part of how I kind of came to terms with it. Then when I was thinking about how to, like if I was leaving the IC work too early, what my manager helped me focus on was what would I get out of doing more of it.

He’s like, “Well, if you want to do VP eng or a head of engineering type role, I feel like you’ve already demonstrated that you can do that. Even if it’s areas that you’re not familiar with, you can work with engineers to figure it out, you’ve done that before, and so what would you get out of it.” I was like, “Oh, I guess I just…” It’s sort of this feeling of like I should do it, I should do more technical work, not that I really wanted to or that I was drawn to do more of it.

Poornima Vijayashanker: It’s interesting that he led you down that path of what would it look like in your current role if you were to do more of maybe the same, or where would that kind of take you longer term, and is that the kind of work that you want to do.

Jean Hsu: Right, and he was very open with me and saying like, “OK, well, you know what? I understand that you may want to go, kind of like shift back a little bit, but for this quarter we really need you here and let’s reassess.” It felt very like a temporary, not temporary, but it was like an ongoing conversation. It wasn’t like if I wanted to go back into IC work, I’d have to leave the company. I always had that advocate in him.

How long it really takes to transition into a leadership role

Poornima Vijayashanker: So you ultimately decided to take the choice and go from being an individual contributor, an IC, into a leadership. What were the first few months like in that transition?

Jean Hsu: It was kind of a long transition. I’d say it was like over maybe two years. The first few months I mean I definitely had this sense of like, I don’t have time to get my work done because when you’re responsible for both the coding work and being responsible for teams or people, it’s really hard to have that, like make your time.

Poornima Vijayashanker: Right, contact switching.

Jean Hsu: So I definitely felt like it was easy to just say, “Oh, I had a day full of meetings. I didn’t get any work done.” That’s a very, very common mindset to have when you make that transition.

When we don’t have something tangible to point to, we feel unaccomplished

Poornima Vijayashanker: I think for me when I went from being an engineer to a founder, the hardest thing was I’m no longer going to have something to point to at the end of the day because before I could build something and deploy it and be like, “Look, what I built,” and at the end of the day I was like, “Yeah, I talked to five people.”

Jean Hsu: Yeah, I started keeping, in the times where I felt like the transition was the roughest I started keeping a log of what is the one thing that I felt was most impactful that I did that day, and sometimes I kind of had to make it up. I was, “Oh, I had a one-on-one with this engineer, and maybe she thinks about herself fundamentally differently now and is now going to interact with people in a slightly different way.” You kind of have to take those where you can get them.

Poornima Vijayashanker: It’s squishy and you don’t see the results immediately and it’s developing a level of comfort with that. I think that’s one of the harder pieces and where people get demotivated when they’re not seeing their results fast enough versus with code it can be very instantaneous.

Jean Hsu: Yeah, and I think management success or being a leader is a little bit more subjective and the feedback loop is a lot longer.

Poornima Vijayashanker: Yeah, let’s talk about that. Yeah.

Jean Hsu: I mean it could be, I mean if you’re just talking about actual feedback that you get, that’s, I don’t know, at companies that kind of have—can I curse on here?

Poornima Vijayashanker: Of course.

Jean Hsu: —have their shit together, it’s like six months. Every six months you get some feedback on how you’re doing, the official formal feedback loop. But beyond that you have the one-on-one. That’s a very individual relationship. I think for a lot of people they don’t really see the impact of their work. One of the things I’ve been thinking about is for engineering work for the most part your impact is somewhat proportional to the work you put in. If you spend two months building a system with a team, that’s two months that you put in. Hopefully it’s an important thing that you’ve done. Then the management work sometimes you can do some tweaking or some restocking up front that can have really big impact that people might not trace back to you, and so you sort of have to see that loop, that feedback loop for yourself.

Managing and leading your peers

Poornima Vijayashanker: Were you ever in a situation where you also went from being an engineer with a bunch of teammates to then being their manager and having them as direct reports?

Jean Hsu: Mmm-hmm. Most of my early direct reports were new grads. In some ways that was sort of easier. I had just been there eight years ago and so I had a very good sense of like, “Oh, this is kind of where you are now, and here’s the type of support you need.” I’d say as a tech lead it was sometimes a little bit more difficult, especially when I was suddenly responsible for managing the work of people who were more senior than me, that I feel like I kind of took a very hands-off approach, which sometimes was like, there’s just miscommunication. But it is something I feel like especially as a manager you have to navigate, like how, it’s OK to be friendly with people. I mean obviously you want to be friendly with people in the workplace, but how much you can be like good friends outside of work.

Poornima Vijayashanker: And how to be authoritative.

Jean Hsu: Right, and navigating that was a little bit tricky to me. Figuring out if someone invited me to something, “Should I go?” I’m like, “What? If I did something, who should I invite?” In some ways I just didn’t hang out with people at work who were on the engineering team because it was like, I felt like I had to invite 30 people. I don’t want to invite 30 people.

Poornima Vijayashanker: Right, so you want to be careful about playing favorites and stuff like that.

Jean Hsu: Right. I think I was especially sensitive to that, because I had seen it, I’d seen it happen. People who are friends go to Vegas together and then you’re just like, “Whoa, I understand you’re friends, but it’s hard to say that that’s completely separate from your work.”

Poornima Vijayashanker: What about the boss factor? I know for myself as an older sister bossiness is just totally normal for me. But did you have a sense of like, “How do I go and be more of an authoritative figure or disciplinarian” sometimes?

Jean Hsu: Yeah, most of my—that kind of stuff was in one-on-ones. I feel like one of the areas that I kind of grew into was to bring that to a more group setting and a lot of my feedback would be around like, “Jean has,” like, “We want to hear more from her, like we want…” People wanted to hear more from me. They knew that I was, kind of like, I had an opinion but I wasn’t like—

Poornima Vijayashanker: Voicing it.

Jean Hsu: Voicing it. Actually after I had to figure out that I was going to leave and do my own thing, I kind of became more unintimidated. I was sort of just saying whatever I wanted to say in meetings, which probably actually made me better at my job.

Poornima Vijayashanker: What do you think kind of got you to that level aside from putting in your notice? Did you have a mentor that kind of helped you see these were hurdles or things that were holding you back as you were doing the transition into a leadership role?

Jean Hsu: Yeah, I mean I had a lot of peer support and my own manager was very helpful and kind of providing that feedback in an ongoing basis. I think for me it was also seeing that when I spoke up in meetings, because one of my pet peeves is like inefficient meetings and—

Poornima Vijayashanker: I agree.

Jean Hsu: One of the things I would start to do a few years in was like, “OK, I’m just going to get up and start to facilitate the meeting and get people on track and kind of cut people off,” and that came out of a facilitation role that we had at Medium, but sometimes there’s unstructured meetings so I kind of just take that role. The first few times it was like, “I don’t know if this is OK. Do people think I’m being overbearing?” But once I started getting feedback of like, “Oh like, thank God you were there to do that,” or people would start electing me to be the facilitator—

Poornima Vijayashanker: You’re doing the things they’re thinking of doing, yeah.

Jean Hsu: Right. I was like, “Why do I just sit here with this sinking feeling of like, ‘Ugh, this meeting, why don’t I do something about it.’’”

Poornima Vijayashanker: Oh, that’s great, so you were, yeah, naturally gravitating towards taking the reins and steering people in the direction. It wasn’t as if you were having one-on-ones with your boss, your manager every week and saying, “I have this problem. How do I deal with it?” You naturally saw opportunities and thought, “I’m going to dip my toe in and see what happens.”

Jean Hsu: Yeah, I think there was probably a long way I could have gone before. One of my goals—actually I never achieved this—was for people to tell, for my manager to get feedback about me that I was over the top because I knew there was a long way to go.

Poornima Vijayashanker: Oh god, yeah. I always push people for that. It’s like yeah, push to a level of aggressiveness and then they’ll know.

Jean Hsu: Yeah, because I could tell that it was really myself holding me back and there was so far from where I was and where that was really going to be a problem, and so I kind of wanted to see what was the range there.

Poornima Vijayashanker: Did you ever hit the—

Jean Hsu: No I did not, I left before.

Poornima Vijayashanker: Something new to aspire to then.

Jean Hsu: Yeah, maybe.

The choice to stay with the known path

Poornima Vijayashanker: What do you think you’ve gotten out of the—now, what is it, a year, two years since you’ve been a leader—what do you think you’ve gotten out of that experience that maybe you wouldn’t have gotten had you stuck to your individual contributor role?

Jean Hsu: I think there’s equal—I was going to say impact and influence, but I feel like even in the IC track there’s ways to achieve that and to lead also.

Poornima Vijayashanker: Yeah, we’ll get to that. Let’s talk about the leadership.

Jean Hsu: As a manager, I felt like it’s definitely pretty exhausting to be the person sort of taking care of people and supporting them, but there’s a lot of rewards there too, which is like you know that these people have someone who they feel safe coming to and there’s issues. I don’t know. It’s just like a level of influence that, what I had from my manager, just being able to extend that to everyone else, that was really, that really meant a lot to me.

Poornima Vijayashanker: Any impact on the product or the company that you can speak of?

Jean Hsu: In terms of the company a lot of my role was also doing engineering operations work, so kind of like team-wide processes, taking what was working on my team or other teams and kind of expanding them to be part of, more of the whole engineering team’s processes. Then something I also saw at Medium was engineering was the largest team. A lot of times engineering would pilot something and then it would work really well and so we’d expand it to the rest of the company. That was kind of cool too, to see that level of like, “Hey, like what’s going on over there? They seem to be like pretty well supported.”

Poornima Vijayashanker: Then coming back to the question that you proposed. If you had stayed in your individual contributor role, how do you think it would have manifested itself?

Jean Hsu: I don’t think that was ever really for me, but I think that once I could see that I was capable of doing it, that also made me much more comfortable to switch to the management track, because I really felt like for a while that I wasn’t cut out to do the hardcore infrastructure platform work, and they’re kind of going that way as my career route. Then I did spend like a quarter or two, really diving deep into platform work, and I could see the path there. Once I could see the path and I was like, “OK, I can see this, if I don’t do people management and some of the other things I’m doing and I just focus on this, I could see how I could get to where this person is in five years or 10 years.” It was interesting because just seeing that helped me kind of be comfortable with moving to the management track more fully.

Poornima Vijayashanker: You mentioned there being opportunities for leadership for individual contributors. So for folks who might in our audience choose to stay as individual contributors for the long haul of their career, what do those opportunities look like?

Jean Hsu: I mean there’s a lot of different, even in the individual contributor, I mean some people include tech lead as part of that track. I think in the more purely individual contributor track you can still expand your influence and you can be the architect of larger, larger and larger things or just be able to coordinate. I mean it becomes less individual even though you’re still doing the work.

Poornima Vijayashanker: Sure, you’re just divvying it up or directing people, but maybe not responsible for their career.

Understanding the path of a new role

Jean Hsu: That’s right, or you’re thinking more about the high-level technical strategy of the company or—I mean, that I think eventually leads to architect or CTO type roles, whereas once I had kind of figured out the paths, I didn’t really have a sort of canonical like VP eng, like, “Oh, this is what a VP eng does, and this is what a CTO does.” Had worked at Google where you have no visibility, to those people, Pulse, which we were just all kind of figuring things out, and then Medium where my manager was the head of engineering and it was very much like a hybrid VP eng/CTO role. But once I had figured out what that actually meant, it was pretty clear to me that the path that appealed to me most was sort of the VP eng route.

Poornima Vijayashanker: Yeah, it’s nice when you have a little bit more transparency.

Jean Hsu: Yeah, because otherwise it’s just like, “I don’t, I don’t know,” like, “I don’t know where I’m going because I don’t even know what the options are.”

Poornima Vijayashanker: That’s a good final set of words for our audience, is getting a sense of what the various tracks look like before you pre-select or make the decision to not participate, just kind of get your facts straight, get a sense of what each role is like.

Jean Hsu: Yeah, the book The Manager’s Path was really good for that because she, Camille, the author, she lays out a lot of the—I like how she lays it out because at the end she talks about all the core things that a company needs and then the different combinations of roles that they use to achieve them, because VP, eng, and CTO can actually mean very different things depending on the company you’re at.

Poornima Vijayashanker: Nice. We’ll put a link to it in the show notes. Thank you so much Jean for sharing all this awesome information. I know our audience out there is going to get a lot out of this. For those of you now in the audience, Jean and I would like to know: have you recently done a transition maybe from being an individual contributor to a manager or a leader? What were some of the concerns you had, and how did you go about handling that transition? Let us know in the comments below this video.

That’s it for today’s episode of Build. Be sure to subscribe to our YouTube channel to receive the next episode, where we’ll dive in a little bit deeper and talk about how you want to manage your concerns around your skills, getting rusty when you go from being that individual contributor to a leader. Ciao for now.

This episode of Build is brought to you by our sponsor, Pivotal Tracker.


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