I don’t know about you, but before I decided to take on my first leadership role, I agonized over it for months! I worried that as an engineer, the coding skills that I had taken years to learn and hone would get rusty.
And I wasn’t alone in worrying.
As I talked to designers, they told me they worried about their ability to design, while sales and marketing people worried about their ability to close.
Well, I’m just going to tell you the straight-up truth: your skills will get rusty.
But in today’s Build episode, Jean Hsu and I are going to teach you why it’s OK if they do!
Here’s what you’ll learn as you watch the episode:
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Poornima Vijayashanker: In the last episode, we talked about what it’s like to transition from being an individual contributor into a leader, and explored some tradeoffs. If you missed the episode, be sure to check it out in the link below this video. In today’s episode, we’re gonna talk about one of the major concerns people have that holds them back from doing the transition, which is the concern that their skills are gonna get rusty. 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. One myth that often holds us back from transitioning from being that individual contributor into a leader is the fear that we’re gonna get rusty when it comes to the skills that we’ve worked painstakingly hard to craft. If you’re an engineer, you’re gonna lose the ability to code. If you’re a designer, you lose the ability to design. And if you’re a salesperson or a marketer, you lose your ability to close. Well, in today’s episode, we’re gonna debunk that myth and more. And to help us out, Jean Hsu is back, who is an engineering leadership coach. She’s gonna help us dive into this myth.
Thanks again for joining us, Jean.
Jean Hsu: Thanks for having me again.
Poornima Vijayashanker: Yeah. Last time we talked about the benefits of going from being an individual contributor to a leader, especially in engineering. And not to shy away from it if we feel worried that we’re not capable of doing it. But I know another concern that people have is not about their capabilities of doing the future work or being a leader, but, “Oh my gosh. I’m no longer going to be capable of doing my current job,” whether that’s coding, designing, marketing, or so on. Why do you think people have this fear?
Jean Hsu: I think it’s something we touched on last time, which is they don’t see the path of the leadership role. So of course you’re going to hold onto what you know, which is the technical skills, the coding, all that stuff. A lot of the times when I have this conversation with people, what I say is, “As a coach what I’m gonna do is I’m gonna illuminate that other path, the leadership path.” And for most of the people I’m talking to, it’s not as much of a technical leadership path. It’s more of a people management path, which are both leadership paths. But part of my role is to illuminate that, so that they then…then the question is, implies that you don’t want those technical skills to get rusty, right?
Poornima Vijayashanker: Right.
Jean Hsu: Which I often feel like it’s a symptom of they’re not getting enough investment in seeing the rewards of stepping into a leadership role and having a more broader impact.
Poornima Vijayashanker: Yeah, or learning new skills.
Jean Hsu: Right, or learning new skills.
Poornima Vijayashanker: Yeah. Is this a legitimate fear, though? Do our skills become rusty as we go into a new leadership position or any new role?
Jean Hsu: I mean, for my technical skills, yeah for sure, they’re rusty. They’re definitely rusty because I’m not practicing them. I think you do have to get to a point where you feel comfortable with that. I definitely was at a point when I wasn’t comfortable with that, when I was in transition. I remember one morning, I woke up and my calendar was back-to-back, 9:00 to 5:30 filled with meetings. I pulled out my laptop and I opened up three pull requests, just delete code that I had found that was unused. It was like 15 minutes. I was like, “OK. Good. I’ve done something today.”
Poornima Vijayashanker: Well, sometimes throwing out trash is helpful.
Jean Hsu: Yeah. And when I told my manager this, he was like, “Is that the best use of your time?” He asked me this. Like, OK clearly you know the answer to that. It’s a rhetorical question. It’s not the best use of my time, and it’s actually indicative of something else, which is that I haven’t really transitioned my mindset to the actual work that I’m doing in this new role, is work. And seeing the impact of it. That wasn’t clear to me yet. So that’s why I was holding onto this thing that made me feel good in my past role.
Poornima Vijayashanker: Yeah. How can you figure out what the new work is? I think that’s a big problem for people, is they’re thrust into this role, or it’s a nice promotion, or maybe they genuinely want it, but then in that first week, month, even year, they’re not really sure what to do on a day-to-day basis.
Jean Hsu: Yeah. I mean, I think adding to that is that a lot of companies have founders or managers who also haven’t done it before. They’re not getting that model of, oh this is who I want to be as a manager. As an engineer, you see all sorts. Oh, this person went to Android or front end, they’re more of a tech lead. This person’s more of a Ten-X engineer type. And you don’t really get to see that as much if you’re talking purely about the people side of leadership, the people management.
One of the ways that you can do that is, I mean it’s a little bit self-promotional, but working with a coach like me, who can help you see that path or help the people on your team see that path. There’s books. There’s definitely resources. There’s a lot of Slack teams, that I think just being in the Slack teams is lurking. You kind of absorb what are the topics people talk about. And what are the things that come up. When you’re not managing people, you don’t see the things, like performance reviews, performance improvement plans, how to reward people, how to give them positive feedback and incentivize them and motivate them. You don’t see that as a post lead.
Poornima Vijayashanker: Yeah. I think you’re onto something, the concept of shadowing. Actually it can be really valuable. For me personally, I got to do a lot of that, having been at a very early stage startup and not as the founder, but rather as a founding engineer. Seeing how marketing and sales and engineering and product all operated and the leaders in those was valuable because when you’re on the ground floor, you see how people develop, but not everybody has access to that. And not every manager enjoys being shadowed. What are some other ways you could simulate that kind of behavior?
Jean Hsu: You know, I think if you have a close peer group at your company, that can be a good place to start to have these conversations. Someplace that’s trusted and confidential. If you’re a tech lead or you’re a first-time people manager, to have someone you can say, “Hey, I have this situation,” and you don’t have to be alone in figuring out a strategy to deal with it, but you can go to your peer and have this peer mentoring or coaching relationship. I found that that’s useful just in seeing what other people are doing and their perspectives.
Poornima Vijayashanker: Yeah. What about setting expectations? I think some managers are good at setting expectations and some are more carefree and want you to discover it yourself. What have you seen in your experience?
Jean Hsu: What do you mean by the expectation?
Poornima Vijayashanker: So the expectation of, hey if you’re a hiring manager, for example, you’re gonna hire 30 direct reports.
Jean Hsu: Oh, I see.
Poornima Vijayashanker: Or if you are the team manager, you’re gonna push this product. Whatever the goals are of the organization. Some people are better at delineating and having a clear set of expectations, along with standards. And others are like, “Well, here’s the company motto. Do no evil and ship.” So you’re like, “Within the confines of that, what do I do on a day-to-day?”
Jean Hsu: Yeah. I think having some quarterly or monthly alignment and expectation setting is useful. It’s the same as the first time you become a manager or a tech lead, it feels really awkward to not have…most people start off with like no stand-ps. Then they’re like, “Well, I don’t know what this person’s working on. I haven’t heard from them in three days.” It’s like, well maybe you should have standups, or maybe you should have some sort of weekly or bi-weekly, every other, twice a week meeting where people say if they’re on track or not. I think that’s generally a good strategy, is to set the high level expectations and then report back on those. Am I on track to hit those goals? Because then it feels like it’s set up beforehand, so it’s not, “Hey I noticed things aren’t going well, so that’s why I’m checking in on you.”
Poornima Vijayashanker: Sure. Then it feels like am I getting reprimanded or am I getting guided.
Jean Hsu: Right.
Poornima Vijayashanker: So, coming back to this concept again of the skills. And as somebody who is either technical or has a craft, and moving away from that into this more amorphous, squishy leadership role, are there actual skills that you acquire as a leader?
Jean Hsu: Oh yeah, for sure.
Poornima Vijayashanker: Yeah, what are those?
Jean Hsu: One of the ways that I was told to think about it, for me, I was sort of like, “I don’t understand. I have these technical skills and now I’m being asked to do this thing where I feel like it’s a completely different skill set. I’m talking to people one-on-one all day and dealing with the things that are coming up there.” The way I was told, or asked to think about it, was that it’s still problem solving, it’s just that the interfaces and the APIs are people and teams, rather than code and services and the systems. They’re still systems, but it’s people and teams, and you have to think about how do these teams, what’s the API between them and it’s more like that.
Poornima Vijayashanker: What are some skills that you can point to now on your resume or LinkedIn?
Jean Hsu: How to give difficult feedback.
Poornima Vijayashanker: That’s important.
Jean Hsu: How to debug teams that are not working efficiently. There’s the low-level tweaks, like, oh, email once a day. The low-level things. But then taking a team that’s not working very effectively and making a bunch of high-level changes in staffing, and then have them actually be able to execute because of the changes you made. That’s something you don’t get to see. Rather than the little refactors, you’re doing more of a full rewrite or something.
Poornima Vijayashanker: Yeah, a re-org, right?
Jean Hsu: Re-org, yeah.
Poornima Vijayashanker: Yeah. Anything else?
Jean Hsu: Yeah. There’s a ton. As many technical skills there are, there are as many in leadership and people management.
Poornima Vijayashanker: Yeah. I think it’s important for people to understand that. What about writing? Do you feel like that’s a valuable skill?
Jean Hsu: Yeah. I mean, Medium was very much a writing culture. Everything was written internally, the internal version of Medium. I feel like that’s something that—I consider myself also still in a leadership role, even though I just work for myself, but I work with a lot of people and I feel like all the time I spend in writing has come back. It’s a huge investment for me. Yeah, it pays off.
Poornima Vijayashanker: Yeah. So in being a leader, investing in writing is good, whether or not you’re actually comfortable doing it or you feel like you’re particularly good at it.
Jean Hsu: Yeah. I think it’s something that’s really valuable to get better at. Even if you’re not publishing. Whether it’s writing emails. I’m sure you’ve all had this experience where you get this massive email and you don’t even read it. And then whoever sent it is like, “But I sent you all the information.” It’s sort of this brain dump, over-communication strategy. I think writing is just a part of communication and figuring out what’s the right level of communication because you can under-communicate, and most people in engineering teams tend to under-communicate. And then there’s this tendency to over-communicate, to try to correct for it. And then people just tune you out. Figuring out what do people want to hear. What do they care about. That’s all part of the writing, too.
Poornima Vijayashanker: Nice. Now what prompted you to transition to being an engineering leadership coach?
Jean Hsu: In reflecting in my time at Medium, I realize that I had a lot of peer support. A lot of peer support and my manager’s support in making that transition. And even then it was hard. So I started talking to people at different companies and realizing that that transition, most people don’t have any support. They have their direct reports and they have to keep it together, so they seem like things aren’t falling apart. And a lot of times, they have the absent, whoever, CEO or CTO, who’s not really helping them and they don’t have that peer. And so I really wanted to…I saw how the benefits of having a really people-centric and caring engineering manager, because that’s really the type of team we built at Medium, and thinking about how to expand my own impact. It was like, “Oh, what if I worked with a bunch of different companies and tried to help them level up their engineering management game?”
That’s kind of how I landed on that. I also really enjoyed the one-on-one work that I was doing at Medium for the team.
Poornima Vijayashanker: Nice. So that’s what you’re doing now? You are a leadership coach for engineering teams.
Jean Hsu: That’s right, yeah.
Poornima Vijayashanker: What’s your sweet spot in terms of a team size?
Jean Hsu: See, it depends. I work with some companies that are like six people. I work with some companies that are like 3,000 people, but the teams themselves are smaller. I really enjoy the 10 to 50 people engineering teams, because I feel like there’s still a lot of malleability in what they’re doing and how they’re building out their management structure. I like to work with first-time managers, because I feel like there’s no bad habits to break. You can just be the one who is like, “This is what management is.” They’re like, “OK. Yes.” That’s where I initially started when I created my business, but now I’m working with anyone from trying to figure out whether they want to go in the people management direction or stay in the technical side of things, or all the way through directors and VPNs.
Poornima Vijayashanker: That’s awesome. What are some questions or problems that you help them with?
Jean Hsu: A lot of it is honestly the mindset. A lot of it is as people move into leadership roles, or they don’t have leadership roles, but they are expected to step up so they can get the explicit role. A lot of it is seeing that they don’t really need the permission or they don’t need someone to be like, “I bestow on you this role. Now you may do these things.” So just getting people to see that. As a coach, I’ll push them like, “Hey, what do you need to try? What are some things you can try out this week or next week?” Then they report back and I’m like, “OK, cool.” It’s really cool when you have a whole team of people just all experimenting with their behavior and you just see everyone just stepping up a bit more and taking initiative.
Poornima Vijayashanker: Awesome. Well, thank you, Jean. For our audience out there who may want to get in touch with you because they have an engineering team or an organization that could use some of your coaching, how can they do that?
Jean Hsu: They can go to my website at jeanhsu.com and I also have a link to my writing, too, there as well.
Poornima Vijayashanker: Great. Well we’ll be sure to include the link right below this video.
Jean Hsu: OK, thank you.
Poornima Vijayashanker: That’s it for this week’s episode. Be sure to subscribe to our YouTube channel to receive more episodes like today’s and short Build tips. Ciao for now.
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