Becoming a manager, career growth, and the evolution of content with Harry Wolff

Harry Wolff

Where are we? What is this thing? Who am I? Existential dread creeps in again in the morning sunlight. My name's Harry Wolff. I have... Oh, who am I? Yeah, that's right. I am a director of engineering at MongoDB. I've been there for about five... Nope, I've been there for five years this month. Longest job I've had, which is huzzah for me. I have been a manager now for around five years, in the industry for over 10 years. Historically, a UI engineer making pixels pushed around on the browser, and then being told that they were pushed the wrong direction and pushing them back, so that was a lot of fun earlier in my career.

I also have a YouTube channel that I post free content, supported by ads supplied by YouTube, about Front-end in general, and occasionally I get feisty and talk about Rust because I aspire toward more strange parts of coding, but that's a weekly YouTube channel about coding, JavaScript mostly, on Mondays. And that's the 411.

Brian

Yeah. I mean, that's a fair introduction. Great work.

Harry Wolff

Yeah. Thank you.

Brian

I want to-

Harry Wolff

Customer.

Brian

So... Oh, actually, I want to... Let's talk about YouTube. Or, at least, your YouTube channel, but let's start with Rust. What-

Harry Wolff

Oh god.

Brian

What do you mean? What do you-

Harry Wolff

What am I doing?

Brian

Yeah.

Harry Wolff

Yeah.

Brian

Right.

Harry Wolff

I'm just trying to stay rusty. I do it all for the jokes is really what it is, because humor keeps me young and graying. I don't know, Rust is... I like to challenge myself. It was funny, I was talking to some friends yesterday about note-taking apps, and it reminded me that in 2013, I decided to make an IOS, a native IOS note-taking app, which the source code is on my GitHub page. It's all in objective C, so I don't know what I was doing with my...

So, it's a strange use of my spare time, but that's kind of where I am with Rust is tickling my brain in ways it hasn't been tickled before, that's a weird metaphor, by learning things that I'm not familiar with.

Brian

I still can't get over that's a really strange metaphor. I'm not able to keep a straight face but if you're listening, I'm like, "Don't say anything about that. Just let it ride. Just go." Yeah.

Harry Wolff

Yeah. Yeah, I mean, I always been a front end developer with Javascript, which is a very high-level garbage collective language that has a lot of the low level concerns handled for me, and always been curious about how things work beneath the hood, so I was always asking the question why, getting an answer, then asking why again. Kind of digging deep. I draw the line at the circuitry. Like, I would not get into hardware because you make a mistake there and then you have to pay to replace it, whereas software you just reinstall it, so it's not too bad, but Rust is just... I mean, it's definitely in vogue. It doesn't hurt that it's the thing to talk about, and it's curious because of...

I mean, the novel thing with Rust is how it handles memory management, and that's a thing that's new as far as modern programming languages go, so I have accepted about that. My biggest pain point in running Rust has been, what do I use it for? Because I don't really have any immediate needs, outside of just like-

Brian

Yeah.

Harry Wolff

... arbitrary programs, but it's mostly a curiosity to scratch.

Brian

Yeah. The reason I ask is that I have... I mean, I am familiar with your positions on JavaScript, which we'll get into in a minute, but also for the Rust content that we put out, like I... You know, I've said it before, and that the Rust community is passionate and so that's both great, and when we screw up... I mean, it's great when we screw up because they'd let us know, but sometimes we don't screw up and they let us know that we... So it's kind of like, "Well, all right. I understand."

Harry Wolff

Yeah. It's an interesting... I mean, I think all... I mean, these are obviously passionate. I think where Rust gets more... I honestly, I think it probably comes from a place of insecurity, if I'm brave enough to say that, because it's still so young that to make mistakes has a far deeper impact than were to say make a mistake in Java, where you have decades of legacy that you can't... Like, that cement's very deep in the ground. You're not moving that. Rust is still close to the surface.

Brian

Yeah. No, I do find that's that... Well, I find that a lot of people say, "I would love..." Or, "I want to learn Rust but either I don't have time or I don't exactly know how." And that's...

Harry Wolff

I mean, the way I learn anything, it's a two step process for me. It's, one, I read as much as I can about it, and I... The metaphor I always use is I like to get a layout of the house, like where's the bathroom, where's the kitchen, where's the bedroom. I understand where things are, then when I actually get down to actually using and living in the house, you start understanding all of your idiosyncrasies, and that just is a result of throwing yourself at the problem. So I've read-

Brian

Yeah.

Harry Wolff

... a lot about Rust now but I've been trying to throw myself at a... to solve a programming problem. I just fail repeatedly, and that's the biggest part of it is just making sure you get back up every time it hits you down. So, it will just keep knocking you down.

Brian

Is there anyone that's been really helpful for you for Rust, that would stand out? Or...

Harry Wolff

The Rust book. The free book that they have is fantastic. I read it-

Brian

Yeah.

Harry Wolff

... on vacation once because that's my choice of free time usage.

Brian

That's a cool book.

Harry Wolff

Yeah. No, I'm aware.

Brian

Okay.

Harry Wolff

I was at the poolside. Like, my wife's reading a whatever and then I'm just like, "Ah, Rust. How to do memory management with a thoughts vector ref." Okay, good. It's also a great sleeping aid too, so both for stimulation-

Brian

Yeah.

Harry Wolff

... and rustation. I don't know what the word is. Yeah, the Rust book's great. I mean, honestly, I've just gone to all the official documentation is the Rust book. You get a overview. There's Rust by example on there as well to show how things are done in Rust. There's cohands that kind of have little, small programming problems that you can approach and then solve for to actually put finger to keyboard and actually apply yourself. What was the last one?

Only recently have I started actually reading the like SDK doc, like actually how things work, and that only started happening as I was trying to code a program myself. Had to actually reference the docs with the manual, especially what I was doing, but I wasn't even up to that stage until I actually had the background general knowledge.

Brian

Okay. That all checks out. I just wanted to pull on that thread as soon as it... We didn't plan any of this. I just, I heard Rust and I was like, "I want to hear what he has to say about Rust." I think probably now it makes sense to take a step back, talk about YouTube, talk about why your YouTube channel exists, and then I'll ask you questions about the things you say on YouTube and maybe we can have a conversation about those things.

So, question number one is, why do you have a YouTube channel? What is that?

Harry Wolff

Boredom. No.

Brian

Yeah.

Harry Wolff

So, there's the... I used to be the guy in the office that would come up to you and be like, "Hey! Did you hear about this 0.1.1 release of this new software that you haven't heard about?" And people would be like, "No, Harry. I don't care, Harry. Go away, Harry." But my excitement was always around that. Just like, new, fun, exciting things, and I eventually channeled that into a podcast where I model myself off of the Daily Show, but weekly, where I talk about all the newest Front-end happenings, and I did that for around two years with a friend of mine, and it was fun, and then it kind of petered out and I migrated it to YouTube where I started doing that on YouTube, and it was in video form, and then I kind of started morphing into doing general YouTube content, of just talking about code, and then I just didn't stop, which is how it goes.

The line I always say to people is, "If I had stopped doing YouTube, I would just been probably watch more TV." Which isn't the most delightful replacement, so, you know, that's an impetus, but definitely going through my own bout of trying to re-find my joy of the channel, because I think I've been in the weeds for a little bit the past year, like, personally, frankly, and I'm trying to just re-find what videos give me joy, to then share that on the channel as well.

Brian

Do you feel like you... Are you, in your own, just the way that you pass the time, are you looking at what's trending in Front-end? Like, are you always keeping up with GitHub and that sort of thing? And then the light bulb went off and you were like, "I should have a platform for this."?

Harry Wolff

Yeah. I mean, it was... Even to this day I still keep up-to-date with what's going on. I used to read 60% of articles that I'd find, and I think I'm down to like 30% now, just due to other time commitments, but the end of it was, the original drive was just if, occasionally... Eventually I found people at my jobs that enjoyed my enthusiasm, so, you know, it validated that there was something valuable there, and then I think one day, literally the thought was like, "Well, if they find it valuable, then maybe the internet might as well." And it was really that thought that opened that door to experiment.

Brian

Yeah. The reason I ask is, Kalin, who's been in this podcast a few times but he's our Front-end developer at LogRocket and he's exactly the same way, and we couldn't, you know. We, meaning the content team. Like, I couldn't do the job without him going, "Hey, is this..." Like, all the time I will say to him, "Does this topic, does anyone care about this?" And he'll tell me straight up like, "No, it does..." Like, "No one cares." Or, "Here's how it could matter." But it's that kind of... And I can't go out and find another Kalin, for example, which is what I like about...

I've watched some of your videos and I like that you've have opinions on things and you share those things, and he does the same thing, just not on YouTube, so that's why I was asking is I'm interested in that, because it's really not... I don't want to say that people don't, at least in the WebDAV space, don't share their opinions, but I like hearing... You know. I don't know how to blog.

Harry Wolff

Well, I try not to share my first impulse, because that's-

Brian

Yeah.

Harry Wolff

... usually wrong, so I definitely have learned, especially as I've gotten older and slower, I've been better at suppressing that first knee-jerk blah! And then kind of refining into bler. And that's kind of what you see on YouTube.

Brian

That's a great way to... Yeah, I like that.

Harry Wolff

Thank you.

Brian

Yeah, no, I mean, it is. It's super accurate. I get it. Yeah. Okay. I almost kind of want to segway into like, "All right, great. So, you take your first impulse and then you go bleh, and then it's like..." Well, also, the idea that's, what if the idea at the Front-end is stable?

Harry Wolff

Well, that's my newest one, right, which is actually funny. I recorded that video. So I open my-

Brian

Yeah.

Harry Wolff

... recent videos was Front-end is boring because it's stable, and it's funny because I was actually looking on Twitter that past week, and all of a sudden I saw all these Tweets about how Front-end's never been more exciting, and changing, and I was like, "Well, that's not what I said." I'm like... Like, it was... Before my video got released and it was in that space of recording it and releasing it, that Twitter was like, "Front-end's exciting." The main point...

I mean, in all honesty, I think most of my points and opinions are boring when you get down to it because they usually distill down. It depends, and I try to keep as close to objective truth as possible, which is also subjective, what's objective, but that's a different podcast, but basically, the way in which Front-end applications are written, at least the UI approach, like how you actually code some button and that gets onto the screen, has largely remained unchanged since React did change everything.

I started in professional development in 2010 when JQuery was still exciting and fairly new. 2012 backbone was rising and that was also very new, then you have mo.js and those were kind of the three paradigms at least I lived through, so that's where I think they matter, because that's my perspective, but they mostly took a fairly imperative way of making UI in the screen where, you know, "This happens so you do this, and then this happens, you do this." The react made the whole declarative model, which people have talked about ad nauseum, where you just say, "This is what I want and you handle the rest." And that's kind of been the MO of most modern frameworks, and that hasn't really changed.

Like, there's been color and accents added around it. You have Svelte taking a compiler-first approach as opposed to a runtime approach. I think [inaudible 00:14:34] on the podcast before, talking about that as well, but the true excitement, in my opinion, of Front-end, is outside the browser in many ways, where you have tooling looking towards Rust to provide features and functionalities that are not possible with just JavaScript.

Brian

So, yeah. I mean, it's interesting to me, the... I've mentioned this a few times in the past, that we, on the LogRocket blog, ran a survey asking people what they didn't like about Front-end, and far and away, the winner was complexity. You know, there's just way too much stuff, so when I see that, and maybe I'm not going to accuse you of clickbait but the-

Harry Wolff

Oh, please. So, actually, that's a funny thing. I've actually been trying to veer towards clickbait more.

Brian

For the views. Yeah.

Harry Wolff

For the-

Brian

Okay.

Harry Wolff

I mean, someone, a very smart gentleman gave a good piece of advice to me, they know who they are, that clickbait, in some ways, says more about the viewer than it does about the author, because what is the honey attracting? Like, we might be making the honey but it doesn't exist without some bees flocking to it there.

Brian

Yeah, I... So, there... Having been doing content for mostly web devs over the last few years, clickbait-y titles, I have the data. It does work. The difference is you have to deliver. Like-

Harry Wolff

Yeah.

Brian

... if you can entice people to read, which is a charitable way of describing clickbait, but they're not going to come back if it's garbage.

Harry Wolff

Yeah.

Brian

So, I mean, also I get accused fairly often of blatant content marketing, and it's just like, "Yeah. Yes. That is what we... Of course that's what we do."

Harry Wolff

It's said as if it's a bad thing but it's literally like... It's important.

Brian

I would love to give this stuff away for free, and it is free, you just have to suffer a small ad at the bottom that says like, "Did you know that LogRocket existed? If you're interested, you could click this button." Anyway.

Harry Wolff

I mean, clickbait isn't a thing that's just from the internet. You talk about newspapers where they have leads, that I'm sure people sweated over to make sure they could put in there, like the... All you have is the title and the small lead of some newspaper clipping to entice people to read their content, and that's the original clickbait in some ways.

Brian

It's... I try not to do... You know. We don't do big declarative statements on the blog, mostly because nobody wants that, but it is funny. Like, the clickbait argument, I guess. I don't know. I don't think we get-

Harry Wolff

Well-

Brian

... views on it all that much anymore.

Harry Wolff

You want to have one step foot in the provocative and one step foot in truth, as long as you can bridge... And then I think, to your point, it's very true for web dev especially, where you want to make sure that you do have that bridge towards meat, because if there's just cotton candy there, it's just going to give people a stomach ache.

Brian

Yeah. I do... And I can't tell. This is something that I think about a lot is there are... I don't know if they're necessarily tropes but there are kind of like... We can call them frameworks. Like, "This is how you write a Front-end blog post." And it's kind of like this versus that, or like, "This is how you do a thing." Or like, "Why you should care about..." There's probably 10 or 15 and I don't know who decided on that. You know, like, "Where did this come from?" And of course we do it because that's what people identify in their Google search results and go like, "Okay, that's the thing I want to look at." But yeah, there are so many other options that we could go with, but whenever I-

Harry Wolff

It's evolution.

Brian

Yeah.

Harry Wolff

It's evolution because someone started it, and that's the one that won and then it grows and it went from, "I have 10 things to tell you about this topic that you're going to enjoy." And then it got down through the many generations of, "Ten things that are great." And you're like, "Oh, well there's that. The wolves used to eat us and now they're our dogs."

Brian

It's funny, like, they... And then I... Well, when I ask develop... or, some developers of... Kalin, for example, when I ask him what he thinks we should do to evolve and he just goes, "Just charts." Like, "All I want is charts. Show me the things that..." He's like, "I just want to see the things that do this." Like, "You don't want... You're not interested in the words?" He's like, "No, I'll figure it out myself."

"Okay, well I don't..." You might be different.

Harry Wolff

Yeah.

Brian

So, one of the things that was talking about or thinking about the evolution of content, our content on being an engineering manager always does super poorly. Like, there's... And I understand why, kind of, but I don't think it's the quality of the content, but anyways, I bring this up because you do talk about being an engineering manager a lot and I think that it probably is perhaps more successful than what we put out, so I like to hear your thoughts on how you think about putting that stuff out. Is it just kind of like things that come to your head and you just want to rip out an episode on that or?

Harry Wolff

I mean, the best thing about engineering content is that it doesn't require as much preparation than-

Brian

Yeah.

Harry Wolff

... technical content because it's mostly verbal and not as hard, which isn't to diminish the value of the content, in my opinion. Like, I still think it's valuable and I put effort into making sure it's good, but it's mostly coming from within that it is... I mean, most of the work is just organizing my thoughts to deliver it in a way that there's a narrative that can be delivered. Even for my YouTube channel, though, those videos, I think I managed to make them better performing videos but historically they've also been pretty underwhelming performance for those.

And I think the obvious reasons that I would point to as well is it's a smaller audience that you're targeting. It's also the niche that I initially carved for myself isn't there. If I was a management YouTube channel, then maybe I'd attract people there, but to have an only-management YouTube channel sounds scary to me. To have content to power that weekly, that would definitely drop down the frequency there.

I'm actually thinking of a video that I might record tonight if I get the energy, another manager video. The impetus is this month is my fifth year anniversary at MongoDB, which is huge for me. This is the longest I've ever been at a company. The longest before that was three years. Typically at tech it's like two years is the average that you hop, skip and jump, so I want to brag about that and talk about it because I like myself. But just having a video that's like, "Hey, I five years at MongoDB. Yay." Like, that doesn't... You know. People are selfish by default, so how is that going to... Like, "What is in it for me?" Like, "There's nothing valuable there."

And I kind of was meditating on that, and there's another video that I've been wanting to do for a while about why people leave jobs, or why you should know to leave a job, and I've have thoughts around that I'll save for the video, but the title that I'm distilling down to is Three Reasons You Should Leave Your Job. And then in there I can talk about how I have not left my job because those reasons do not apply to me right now, so it's kind of like, weaving in my personal... And, actually, it gets pretty woven I guess. It's a nice wicker basket. Not the wicker mat.

I'm sorry, I have like random tangents are just over aged.

Brian

I got the reference.

Harry Wolff

Perfect

Brian

[crosstalk 00:22:25]. I'm with you. Yeah.

Harry Wolff

I know that I'm old when no one gets my references anymore. That's how I know that it's time for me to clock out and skedaddle. It always hurts my soul when a reference is unmet but I... Yeah.

Brian

For me, I've realized that it's just, stop making Simpsons references at work because nobody's... Just stare at you and go like,

Harry Wolff

That's a deep drove to pull from, too.

Brian

Well.

Harry Wolff

Because you have this... Well, there's like, surface level Simpsons jokes but like, you know, our generally applicable then you have the niche ones because I don't...

Brian

Oh, sure.

Harry Wolff

... have that. So, I don't have the niche ones at all [inaudible 00:23:00].

Brian

No, because that was in like, '94 and-

Harry Wolff

Right.

Brian

... you know, it's was not the focus of the episode. Anyways-

Harry Wolff

Holly was tappa, tappa, tappa. That's my gold standard.

Brian

Nice. You got me. Your audience of one thought that was funny. I mean, it's funny, like the... Thinking... I've seen plenty of, "How to prepare for an engineering interview." You know, those are very popular, and you're suggesting the opposite, how to create... Like, how to not interview. How to leave your job. And I have some-

Harry Wolff

Well, it's more like-

Brian

Yeah.

Harry Wolff

It's more like why. Like, why should you. Like, you know, "Does your manager suck? Well, you should leave." Type of thing.

Brian

Yeah. Well, I've seen plenty of content out there that's, "If you are wondering whether your manager sucks." Or even, "If you are thinking about, "Should I not be here?" Then maybe you should go." Which I don't think is true. Like, I don't... Now we are definitely wandering into the territory of the video you'd like to make, but-

Harry Wolff

I mean, I'm not too upset about that. Like, you know.

Brian

Yeah.

Harry Wolff

I've also learned, in my old age, that repetition eventually gets the point across, and there's no, you know. If something's so fragile that you can't repeat it, then it's not worth saying, so, you know-

Brian

Yeah.

Harry Wolff

... go for it.

Brian

Okay. So, I don't think... It's okay to evaluate. Isn't that the whole point? Like, you're evaluating what your future is like and it is possible for new information to... Like, you should bring it up. That's really... I think. Like, if you think that you're not happy at a company or your role, or whatever it is, you should maybe go to your manager. I don't know how that conversation would go and be like, "Listen, I think that you're doing a bad job and I'm unhappy with you." But maybe. Like, if it would work anywhere, I suppose it would work in engineering.

Harry Wolff

I mean, it's also validating your perspective of reality is true, right. Like if you're unhappy and you're uncomfortable, can you turn to your manager to validate that's real? Or do you have to turn to a friend to confirm that? Because that's where a lot of my insecurities come from is I'll have some belief but I want to make sure that it's one that is shared outside my own two eyes, which, you know, ideally you can rely on your manager to say like, "Yes." Like, "You're not growing because I failed in some ways." Is ideally the conversation that is there, right, like, "I haven't been challenging you. You're not really getting new things to do." So like, "Yeah, let's either give you new challenges or you... There's no more room for you to grow here, not for lack of you but for lack of the company's needs." Type of thing.

Didn't even think about what I'm going to talk about in the video but that's still an interesting point.

Brian

Yeah. I think that would be hard for some people to go to a peer and be like, "Are you having a nice time?" And if they say, "Yeah." And you're like, "Well, I'm not." And I guess it depends on what you're working on or just, all kinds of stuff.

Harry Wolff

Yeah. It's also like the question of, is it okay to leave a company because you're bored? And I wrestled with that for a long time and I think that's related to what we were just talking about. If you're not being challenged, you're not being stimulated and you crave that, you need that, it kind of show itself as boredom. I think that is a very valid reason to look elsewhere.

Brian

For sure. I think that can be pushed. And I'm not being contrarian here. Like, I mean, if you're bored in really any walk of life, you should maybe consider a change if it's not... But on the other hand, for your career, sometimes boredom, you can do other things while being bored-

Harry Wolff

Yeah.

Brian

... in your profession.

Harry Wolff

Well, it's like-

Brian

Yeah.

Harry Wolff

... is it engenic or is it just transitory?

Brian

Now we are on a truly deep conversation about boredom, which-

Harry Wolff

Deep thoughts.

Brian

Deep thoughts.

Harry Wolff

With PodRocket.

Brian

With PodRocket. Kate's in the background listening to this, going, "What are you guys doing? Like, I did a good job outlining what this should be like and you guys are talking about what it's like being bored. I hate you Brian." Which is fair. Okay, so, but you do have a video on why engineering managers fail, right, so can we-

Harry Wolff

Oh, sure. Yeah

Brian

Can we talk about-

Harry Wolff

Sould we get into that video?

Brian

I mean, I think you did.

Harry Wolff

No, no, no. I've now done YouTube for over three years, where I actually was preparing a video two weeks ago. I was like, "Should you use TypeScript?" And I was like, you know, I did the outline, I've already recorded, then I searched my past videos for TypeScript and I was like, "Oh. I made this video already." I was like, "Goddammit. That's pathetic."

Brian

Yeah. That happens a lot when you put out a lot of content out. Fortunately, we're like, "Did we already do this?" Well, I mean... So, at some point you made a decision to get into engineering management, right. I don't know how much you've talked about that. And then at some point you noticed that there was some kind of pattern, right, with why engineering managers fail in the first place. Maybe you could talk about either... Both of those things really. Like, how did you make the decision to go from individual contributor to management, and then how do you see why some succeed when others fail?

Harry Wolff

Sure. Yeah. I went into management because of boredom. It is a very simplistic way of taking it but I got a little bit... I got bored of doing this. I found what I was doing as an IC, too reductive for my taste, where it was like, "Here's a thing to code." Code the thing. Okay, good. And that's horrifically reductive, but that's where I was at, and I was not really finding joy there anymore. And I've always been on the UI side of things. I enjoy how things were made but also why things were made. Like, saying to make a form is not enough for me. I need to know why and how it's being used. Even if it might not inform or change what I'm doing, it helps give me incentive and internal word to do that.

So, I've always enjoyed talking to product managers and design, understanding more how they think and just having a more general overlay of how things are decided and put together, and then I also enjoyed, you know, I find myself to be a fairly personable person. I'm able to talk to other people and potentially focus or rally them around some need or cause, and that's kind of where I started looking to management and curious about what it was like.

It was mostly like, "Can I do it?" Was the first question. Like, "Can I do management? Is it something that I'm capable of?" And then I got the opportunity to try First Data startup, where I was leading a small team, and I think that my responsibilities... I always split things with technical and non-technical skills, and at that job I think I was 80% technical, 20% non-technical. And then I came to MongoDB from there, started as an IC, then got promoted to be a manager again, and I slowly started to see that ratio invert just due to needs of the team but also just seeing my own stress level increasing. Like, the higher the amount of code that I would do, the higher my stress would become because then I still have all the non-technical work required of me that I didn't have time to do during the day because I was doing technical work.

The weird thing about going into management is that all the skills that you've learned and gotten good at don't help you anymore. You might've learned how to swing a hammer and hit a nail on the head for the first time really well as an IC, and put a four-by-four together real fast, and as soon as you become a manager, you're the one now saying, "Here's the outline of where things should go but I'm not swinging that hammer anymore." And that impulse to know, to want to swing that hammer, is very strong because you know you can do it, but then you're not empowering the team. You're also not making sure that the bathroom's being installed correctly. I don't...

All my metaphors are about houses because I listened to Brick House this morning, which is a lie just a reference to make.

Brian

I did notice there were house metaphors but I, again, it's not my place-

Harry Wolff

It's-

Brian

... to judge.

Harry Wolff

At least they're not in the toilet. [crosstalk 00:31:18].

Brian

We're not there yet, but okay. Yeah. Okay, so, yeah, that's true. Right? Like, I did the same thing, becoming IC and then going into management, and one thing that I would say a lot is I felt like I wasn't doing... In some ways it's a very kind of... It's almost immature on my part. I was like, "Well, I feel like I'm not doing real work anymore." You know. Like, "I feel like I'm not making stuff. Instead I'm..."

Now, I can understand intellectually I am helping other people develop their careers and doing stuff that they haven't had an opportunity to do, and all of those things, but there is something in me, and I suspect a lot of people, where it's like, you do feel, you know. I'm in meetings all day. I'm not the one that's responsible for making the thing that people enjoy. Directly. Which is, again, is super... It's so linear. Like, why... You know, if you just...

Harry Wolff

Well, it's also like, if you got used to drinking Coca-Cola for many years then it was told that's not healthy and you switch to water, you're not going to enjoy water right away. Like, switching into meetings all day, you're not going to enjoy that right away because you got used to doing the work for a while, so there's definitely this transition period where you have to kind of re-acclimate. It's also all the metrics of your past success have gone away too. You're not being evaluated on how many articles you're writing, how many lines of code you're writing.

Brian

Yeah.

Harry Wolff

And you got rated on these very abstract goals.

Brian

I'm trying to think if I agree. I mean, obviously there's a difference in marketing and engineering, but in marketing, there are some very concrete goals, but the goals are, "Did people come and read the thing?" You know what I mean? Like, it's that. It's not, "Was it good?"

Harry Wolff

Well-

Brian

Yeah.

Harry Wolff

There's probably been one thing. It's one campaign, right?

Brian

Exactly.

Harry Wolff

So your purview becomes... And then you yourself, it's impossible for you to make every individual thing succeed. You just have to make the campaign itself succeed, and that's kind of true for during as well if you're not going to be coding every project but you have to still make sure that every project succeeds, and that's a very different thing to accomplish.

Brian

Did you feel equipped to... Like, when you went into management, did you feel equipped to not just manage people but to coach them, to listen to their problems, to sort that out? Because I think a lot of times, people are surprised at what you end up hearing in those one-on-one meetings. Not just about you, about everything.

Harry Wolff

So, I got to cheat because I was in... I did therapy in my teens, so I got to just cheat, and I was like, "Oh! I've done this. This is a..." Because after a while, one-on-ones can turn into that I think. Honestly, I think healthy one-on-ones don't look too dissimilar to therapy, except you're not really delving into-

Brian

Yeah.

Harry Wolff

... issues when you were eight, just issues about like, you know-

Brian

Yeah.

Harry Wolff

... the eight things you're supposed to do. It was really... I think the biggest challenge was shedding my IC responsibilities and being okay with that.

Brian

Yeah.

Harry Wolff

That was the hardest thing for me.

Brian

Yep, a hundred percent agree, because it was true for me too. It was very much like... Because I felt really... Now I feel like I'm in therapy. I felt a lot of ownership over that, you know, like this is my-

Harry Wolff

Yeah.

Brian

... baby. You know?

Harry Wolff

Yeah.

Brian

So, yeah. I think a lot of people feel similarly.

Harry Wolff

And there's also just... I mean, there are new things for people management that you just don't get practice at if you've never done it before, and you hear about it and you understand it, until you actually feel it. It's a whole different process to go through. And then just fail doing that. That's a weird thing too. It's like, you have to fail again at the things that you've never done before, and being okay with that and learning how to iterate on that in a very timely manner, because it's people that you're iterating with-

Brian

Right.

Harry Wolff

... and that's sensitive.

Brian

It is. There is a certain amount of emotional intelligence that's critical. And you-

Harry Wolff

Yeah.

Brian

I don't... I'm sure you can get better at it. I know that there are lots of formal classes out there but whether or not they resonate with the individual is... Yeah, depends on... Because I've been to some formal management training, and to me it's kind of... There's things that are super obvious, like, this isn't, you know, "Yes. You're right. I should tell my team what's going on." There's... You know what I mean?

Harry Wolff

Well, so, actually for the longest time, I refused to read management books because I had hubris and was like, "I know these things. I, blah, blah, blah, blah, blah."

Brian

Yeah.

Harry Wolff

So I'm finally reading my... I have a list now of books to read, also in large part just so when I ask people for advice, they can no longer tell me to read these books. I just need to cross it off my list of things that people can suggest to me so I can go beyond that. So, I'm reading The Manager's Path right now by Camille Fournier, and it's good. Again, it's not things that are revolutionary to me but what's actually really nice about it is that because it's a book and it's been iterated on, thoughts and ideas that I've had are very nicely put succinctly into the book, and you can kind of see ideas thrown at me that I'm like, "Oh, this is the thing but put in words that I can actually then repeat outward again." And that's been actually very nice to read.

Brian

Okay, so when you were making the decision between, "Should I go from an IC to management?" Did you consider going into product at all? Because I feel like those technical PMs are, you know, like they're very much in demand. Yeah, is that something that... And you had mentioned earlier that you liked talking to product folks, so I'm wondering, is it something you considered?

Harry Wolff

Yeah. Heavily actually.

Brian

Okay.

Harry Wolff

That was great question. Yeah, for a while I was like, "I want to do products. I really want to do products. It sounds really interesting. It seems like they have a lot of fun. They kind of dream up what we're going to work on. They talk to people." Like, it's all this cool stuff. And then I didn't, just because that path is a greater reset for my career than going into technical management. Like, that's really a career pivot. Even though it's the same industry, it's still a whole different set of practices.

But then as I've gotten older and as I've learned more about the day-to-day going ons of a product manager, the more grateful I am I never entertained that thought beyond just an idle curiosity, because I hear about they have to talk to customers and then listen to customers. It's not just being like, "Hey, you like our stuff? You want more of it?" It's like, no, "What's your problems? Let me hear about."

Like, that's therapy there for the company, and that's-

Brian

Yeah.

Harry Wolff

... exhausting . That's not a thing that I find enjoyable, talking to customers and soliciting that feedback and then distilling it, and then the most unenjoyable part in that is then taking that feedback and applying it to the company roadmap. Like, that bridging of from customer to the roadmap, that is laborious. That is not something that I would... I mean, I could do it, I think, but not something that I would really enjoy to do for ever, because that's a long... Then I've now written more documents as an engineering manager. Like, design documents, which product managers do, so I'm not as opposed to that but there's this big...

You dip more into sales territory, I think, is what it is, which is not something that I... It's not sales in the sense of selling a product but in sense of selling a relationship and selling that.

Brian

But there is... I mean, there's a big... Like, I'm talking to more and more product folks this month and there's a big demand... Or, not demand. They're interested in acquiring more technical skills, and I don't think it's because they're interested necessarily and actually writing code. It's so that they can be more persuasive, either internally, and so if you came from engineering and you're a technical PM, I think that would be much easier for you to talk to the engineering team and explain, "This is why we're doing this feature. This is how we could do it in this time." And in a way and basically speak the language. Like, that, to me, makes sense. Now, whether or not you enjoy it is up to you.

Harry Wolff

Yeah. I mean, it's also interesting because the role and scope of a product manager varies greatly with the size of a company.

Brian

Oh for sure.

Harry Wolff

Like, I hear about the product managers talking to other enterprise companies at MongoDB, and I'm like, terrified. Frankly terrified of the people they're talking to, so I'm like, "That's..." I feel way out of my league there.

Brian

Yeah. No, it's... Believe me, it's so different depending on... The PM function is very different depending on the vertical you're in, the size of your company, the stage of your company. Like, it's a wild place.

Harry Wolff

But still, regardless of the size and complexity, if you're a good product manager, you still have a lot of relationships to build, a lot of documents to bridge, mental thoughts, and there's all that work in making sure that the business is growing, which, again, is not... That's not where my joy rests. It's more like, "What's the-

Brian

Yeah.

Harry Wolff

"What's the... How can we build the product?" Like, "What's a fun, exciting thing to do?" That's what I enjoy, but the prerequisites to get there, which is the meat and cheese of the product manager, I'm just going to double down, is not... It's like a stomach ache. It's not what I enjoy.

Brian

Today we found out that meat and cheese is not something that Harry enjoys. I don't know what... Just, lots of people don't. You have... Oh, this has been one of my favorite episodes. I don't know that we have followed a single thread. If you're in your car or walking or... Hopefully you've enjoyed the time with us. Is there anything that you would like to promote, that you'd like to tell people to listen to, go find?

Harry Wolff

Well, I would love to hear-

Brian

This is typically what I-

Harry Wolff

Yeah. I'd love to hear people's favorite metaphor, first of all, or-

Brian

Yeah.

Harry Wolff

... a weird reference. Would love to hear that. Tweet it at me.

Brian

Record Man is probably going to be tops, yeah.

Harry Wolff

Yeah. And then also, yeah, I have a YouTube channel. You could... Easiest way to find it is probably my Twitter account, so at Twitter.com/HSWolff. It's Harry, middle name Spencer, I made that a secret, and Wolff with two Fs. The extra F for good luck, because we all need some good luck. Or just ancestors that had it spelled that way. And that's kind of it. MongoDB is hiring always, so you're always welcome to apply there. I feel like I'm obliged to mention that. I imagine... Yeah, that's enough.

Brian

Awesome. Thank you for coming on PodRocket. Good luck to you. Good luck to-

Harry Wolff

The meat and cheese.

Brian

The meat and cheese, and the audience for making it through this episode. I'll see you next time. Thanks for listening to PodRocket. Find us at PodRocketpod on Twitter, or you could always email me, even though that's not a popular option. It's Brian@LogRocket.