Management as a Career Calling

I was interviewed on an engineering management podcast! Listen to it on the web via managingmanagers.tech or on Spotify!

In July of last year, Pat Kua emailed me to ask if I wanted to be a guest on a new podcast he was creating: The Managing Managers Podcast. While I’ve never met Pat in real life, I was familiar with Pat’s work across the engineering management internet/Twittersphere, and he had previously included some of my blog posts in his LevelUp newsletter. After talking through the logistics, we scheduled a recording in September, and in the first week of March the episode went live.

Working with Pat was great. It quickly became obvious that he was experienced in this type of thing, he was extremely kind and responsive throughout the process, and the software he used to record the podcast worked without a hitch.

I admit that I had some initial trepidation when considering his request — generally around accidentally saying something stupid or regrettable — but several years ago I made the conscious decision to adopt a philosophy around saying yes to “free” career opportunities. “Free” in this context means opportunities without dramatic tradeoffs, including new opportunities that scare me a little but don’t cost much other than time and effort. This has turned out to be generally good advice, and it’s paid off over time.

Overall the interview went well, and it was definitely instructive. There are things I’d do differently next time - look at the camera more, be more conscious of filler words, etc. - but those takeaways are only borne of reps. My main hope before recording was that what I said during the interview would correctly encapsulate my thoughts on the topics at hand, and I think I accomplished that.

For a ~45 minute interview we covered a wide breadth of topics, including my career journey to date, why I think management is “a different planet” than IC work, and how I evaluate my own performance as my role, scope and title both increase and get less defined.

A couple topics I particularly enjoyed talking about(via Pat’s transcripts, lightly edited for clarity/brevity):

Management as a career calling

Patrick Kua: Great. I’d like to maybe backtrack a little bit and go back to one of the things I heard you say. Which was, I heard you say, the management track as your true calling. What does that mean to you?

Yeah. That’s a really good question. This is actually a thing that I’ve talked about with a number of people. I’ve had people email me, being like, ‘hey I’ve thought about going to the management track…’ I have tactical reasons why I think the management track is better suited for me personally. I think it aligns a little bit better to some of my skills. Some of my differentiating skills. So, for example, I really don’t struggle to put my thoughts to paper. Which sounds really weird, right?… But there’s this trope, “Oh I tried management and it was horrible. I was in meetings all day and I had to write docs all day.” That’s kind of true. I think it’s a very uncharitable take on it, but inevitably a lot of your artifacts are communication, either written, in person, or presenting. And if you hate that, maybe this isn’t the job for you. But I don’t mind that. I actually have never struggled with any of those parts. So that part is not even a thing that I consider a blocker.

The other thing about calling, though, that I can’t really explain really well… the analogy I actually give people is:

So growing up I owned a bunch of guitars. I owned maybe five. And I knew a lot about guitars. I can see a guitar from my desk right now. But the reality is I suck at guitar. And the reason is when I pick up a guitar, I just don’t care that much. As much as I appreciate a good guitarist, I understand a lot about it and I can probably identify what guitar they’re playing. And I like music. But when I sit down to put in the reps of building the callouses and doing the scales and learning the music theory, I just don’t. I never did. It’s just not resonant.

Whereas when I’m in the work of day-to-day management, I really find this intrinsic value in understanding incentives, living out the cultural beliefs that I want to be true in a team. I don’t really mind the long feedback loop. A lot of the pitfalls that I think people don’t like and the main differences between an IC track and a management track are things that I don’t really find that problematic. Ever since I stepped into the function… I like planning. I like making a strategic decision. I like taking a diverse set of inputs. I don’t mind the meetings required to do it. I like understanding the incentives of non-engineering people to help dictate our roadmap. I really like the mentorship aspect. So in that way, it’s really hard to explain resonance, but it just feels better. That isn’t to say I don’t like to code. I was a staff engineer and I did write a lot of code. It’s just if I had to choose, it’s the management track.

My three expectations for my performance

Patrick Kua: Great, Yeah, no, you’re absolutely right. Which is, as you talk about, it gets more generic perhaps. Or more vague. But there’s that sense of more responsibility or accountability associated with that title. And that’s an interesting dynamic because at some point, there’s expectations. So if you’re thinking about your manager, how do you think about, are you meeting their expectations around your job as a director in your role?

… I’m driven by three goals when I think about what I want my managers to get from me. The first goal is: I want to demonstrate excellence in my function. I want to be unquestionably good at what I do. I don’t want them to ever question my competence as someone who is accountable to the business outcomes and the strategic outcomes. Managing up. Managing across.

So there’s the technical stuff. Am I accurately representing our wins and our challenges and our context to the company leadership? Am I taking the appropriate inputs? Am I approaching them with the appropriate strategic context and the data that’s coming in from marketing and strategy and the business side to help drive our roadmaps? When I have the opportunity to speak or to create a written artifact, is that artifact good? So I think that’s a big thing. Do I demonstrate competence and, thus, serve as an exemplar for them, in terms of what does a strong manager look like.

The two sides to the management coin are not only are you good at the technical stuff but are you good at the human stuff, which is critical. Do I manifest the values that I say I care about? Do we have the culture? Does our management sync and the wider syncs demonstrate the psychological safety that I think that I proclaim is critical for the success of a team? So I think that’s a big thing. Am I good at my job?

The second goal is: am I in the work with them? Am I actively coaching them through problems? I recently listened to this podcast by Scott Galloway, who’s this famous person. He was a CEO and he’s a podcast host. He’s an NYU Stern professor… And he talked about how he thinks the two frameworks to think about leaders are the inspirational leader and the player coach. The inspirational leader gets up in front of people and is like, “Here are the reasons why you should work here and why this is a good use of your time.” And thus when the inspirational leader gets on stage, everyone is very excited to work for this company.

The player coach, conversely, is not really about that. The player coach is more, “Hey, you’re making a presentation. I’m really good at presentations. Let’s work together and let me walk you through how to make a really effective presentation.” So for me, I think the inspirational part is kind of embedded in the first component. I want to be good at my job. But the second component, player coach is really important too. I have a lot of experience. I’ve gotten a lot of reps. I want to make sure that when my managers are trying things, I’m able to lend my experience in reps to them to make them better and grow their capability to create a roadmap, or to define a strategy, or even make a presentation.

Then the third component to this is I really want to make sure that I’m sponsoring their career growth. I heard the saying once, “Work for someone who will mention your name in a room of opportunity that you’re not in.” So I think that’s really important. I think the notion of understanding the career goals of my reports and then when I hear an opportunity where someone in engineering leadership is like, “We need someone to streamline onboarding” or “We need someone to streamline incident command,” I can put their name in the hat, if that’s something that’s consistent with their goals.