taylor desseyn

guidance counselor 2.0 · episode 103

w/harry wolff, director of engineering at mongodb

jan 19, 2022 · 31 min · with harry wolff · hosted by taylor desseyn

key takeaways

  • job searching remains difficult at all experience levels; prepare emotionally for six months of active searching.
  • hiring managers should define role clarity and team fit beyond technical skills to reduce candidate burnout.
  • culture thrives when teams reach flow state, passing information naturally without explicit coordination.
  • management requires learning interpersonal skills not taught as individual contributors; prepare for unfamiliar work.
  • stay persistent during job search and keep applying until offer is signed; external factors outside your control matter significantly.

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about this episode

engineering leadership at mongodb: hiring with intentionality, building team culture through flow states, and managing the emotional toll of job searching.

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full transcript

auto-generated from the audio, so expect a few typos. the audio is the source of truth.

Hello, hello. Thanks for listening to Guidance Counselor 2.0. Listen, I want to give you a quick rundown of what this podcast is and what you're about to get into as you listen to these episodes. We had Guidance Counselors in middle school. We had Guidance Counselors in high school, but we didn't really have Guidance Counselors in college and now as professionals, we don't really have anybody to turn to to ask a quick question to learn something about the job search or to navigate your career. So that is what I want this podcast to be for you. I want it to be a tool for you to navigate the job search and your career.

So that being said, I hope you enjoy this episode. And if you need to reach me, Taylor at vaco, VACO.com is how to get in touch with me, old-fashioned email, social media at tdesinted E S S E Y N. And finally, please rate and review this in the app store because I want this to be discoverable for others so they can navigate their careers. Hope you enjoy the episode. the people what they want. Who are you? What do you do? And then we'll go from there. Question asked myself every morning. Who am I? What do I want? And then I got a new mirror because I smashed it.

My name is Harry Wolf. I am a director of engineering now. What a fun title. I'm a manager of teams currently managing two teams trying to get a third online. I've been in the industry for over 10 years, which makes me still young at heart but olden bones. So there's that conspiracy inside me. I am a manager so I am able to talk. I have a YouTube channel that I update with a, yep. And I too enjoy to plaster my face in more places than again just my morning beer, bedside lamp, shade, whatever, for associations where I go sometimes. And yeah, I'm based out of, I'm in Connecticut, just outside New York City.

So I get the lovely benefit of trees with just a short little hop skip train ride to the city. But we're getting MongoDB for five years now. And yeah, happy to be here and excited to talk about things that are weird to talk about. talk about. Yeah. They're hard topics. They're surprisingly difficult topics. Yeah. Correct. All right. So let's dive in. And so let's dive into the job search, right? So you said a lot of great things, you know, off air around timing and a little bit of luck. So I'm interested if you can just dive in. So for the job seekers who are watching today, one, what's some thoughts for those individuals?

Absolutely. I have many thoughts, some of them are valuable. So I actually had a YouTube video not to self-promote terribly much. But I do have a video called, I think finding a job sucks. So there's my opinion on it for you. But I think that I mentioned to offline was that no matter how long you are in the industry, finding a job still remains very challenging, difficult and demoralizing. I think it's really a thing to say. I think there's a lot of excitement around it and there's a lot of change around it, but I think people don't really talk about the uncomfortable aspects of it, which let's call a spade a spade and just get down to the knuckle-tax of it.

But yeah, finding a job is very hard. It doesn't really get easier. You do get more used to it, which is to say that, you know, first thing you get burned by a fire, it hurts really bad, and it really hurts. But second, third times, you know, it still hurts, but you know what to expect more. You can kind of prepare yourself better, which is not to advocate for you to burn yourself, but there you go. Yeah, that's the little ramble. I'll let you kind of go with it there. No, I love it. And so, but talk about, so one thing you mentioned is about luck, right?

And I want to bring that up too, because I post about this too, a lot of times, with people getting rejected, and people not finding a job, it's like 50% not you, at least. And so I was wondering if you have thoughts on that. Absolutely, 100%. Finding a job, I feel like people talk about luck a lot, but skill is what makes luck more possible to happen. I think it's true I've seen like roughing stuff swears. Like your skill and experience is what allows for you to get into the door and then luck is what gets you, you know, what you stay. So many times when you're interviewing at a company and there's just so many factors side of the immediate skills that are being desired in that role that are out of your control.

One of the things to look at is the timeline of that job search for that company. Is this a new role that just opened up? Or is this a role that's been opened for six months now? And the perception of the team hiring is so different along that timeline. Typically from experience, when you start a new job search, you come in with a lot of energy, excitement, and high expectations, which is to say that if you are applying for a role recently opened, you may be at a greatness advantage without you knowing it because the bar may either be set impossibly high. And alongside that, the team itself may not be calibrated correctly to know what to really look for.

So in many ways, it is a look at the draw because when you look at the job opening, some do say how long they've been posted for, but most don't. So knowing that is actually a hidden hint on to where somebody, what you may be facing going into it. And you can't control that. It's just like, that's the job. And there's a gumball machine in your local diner. You don't know if those gumballs are newly put in there. And delicious. I thought about this often. Right? Yeah. And you might also invite into one. And there's like, well, that's a bad matter. I'm not going to say that was really gross.

But yeah, you don't know if it's really stale and might break your teeth. Like the external appearance is the same. So let's talk about calibration real quick. Because I'm interested to dive into that. Because I think that's the biggest issue I'm seeing right now, all these companies have budgets. All these companies are hiring. They're like, oh, great. We're just got an unlimited budget because we just didn't hire last year. So we're just going to hire, hire, hire. And there's no intentionality behind the hiring. Sometimes I've even asked managers, Hey, what is this position going to be doing? They go, I don't know. So what how, yeah, not the best look.

So what are your thoughts about how you structure interviewing for your teams? What's kind of the thought process of like, all right, we need this person. Then what? We need this person, let's craft the job description, let's set the interview panel. What does that look like and how do you bring intentionality to hiring for your teams? Yeah, I mean, there's a lot of logistical work needed to just get a job opened up, which as you mentioned, everything you mentioned is accurate, interview panel role, stuff like that. There's, you know, in the panel, it's aligned with the team to set expectations. And then there's also some, there's, but I try to impart on my team with hiring is, you know, almost like what I try as best I can to make explicit the general idea of what this person will be doing on a team because you're hiring a person with skill, but it's still a person and that's not really a finite thing.

So you're trying to get a net that is as accurate enough to catch the person that you want to include on the team. So do you go back, granular? Do you go like in the first 30 days, 90 days, six months? I mean, is that something that you take a look at? No, what I typically do with my team is actually kind of, set expectations for what they should expect for this person on the team. And I mean, I see that people do like, no 30, 60, 90 days. That's a lot of work to outline that. And I just don't do it because I have other things to not do.

But like, for example, I try to, I like to impart images and ideas and kind of create sentiments of what we're desiring, which is hard to capture in words. So for example, it's like this person we wanna include on the team, the first question is what's the seniority? Like how much experience do they want? So for example, if you're trying to hire a senior person, it's like this person that we're looking to hire, when you interview this person, Is this something that you could see turning towards for mentorship, right? Like, is this a person that you would like to include for that? And the inverse is true for somebody that's less experienced.

Like, is this something that you would want to mentor? Like, it's all of these non-technical skills, but just teammates, interpersonal skills that are, you know, that it's truly the aspects that are, that it's the summation where the parts make up bigger than the whole. Right? It's like, what is the overall picture that this person will have on the team, that the discrete, fact, like the discrete bullet items will be included in that, but like where's that full picture of this person as they are looking to be added to the team? Why is that? So the more and more, right, talking to your boy Dan, right, talking to so many engineering leads, the more I interview y'all, the more I hear, hey listen, we try to go beyond the tech, right?

We try to look at the intangibles. Why do you think the industry is still so plagued by if you don't have React, we're not gonna hire you? It's easy. I mean, it's easy. Do you wanna be an NBA All-Star? Must be at least six feet tall. I mean, the world is huge and it's an easy discriminator. And the fact is that you do get a huge influx of people. So you're trying to make your, like people are selfish. Like how are you managers included? Like we are aggressively selfish. So how can they realize easier? So let's include these easy discriminators, just to like get down to a set that the human mind can at least grasp and get some insight into.

That's so good. So let me ask, so let's kind of go into, since we're kind of moving towards the kind of culture and leadership side, how, what are some kind of main principles that you like to, I guess, employ on your team to building good culture? Yeah, yeah, I love culture, especially culture under a microscope. That's a good culture. Yeah, good culture, like, you know, yeah, culture test, I don't know, whatever. So I have a fallback metaphor that I always use, which I love because I get to repeat myself to new people and it makes it sound professional and original, and it's not, it's tried and tried, and I'm telling you my secrets, Harvey Harry, don't refer to his from third person.

Okay, so I like to, so I typically with being a engineering manager, I always look to sports as a metaphor. I'm a huge metaphor of person. I do beyond four metaphors a day because that's my quita. But I just drop things, right? It's just like dripping. This is why I'm a part of this part. I love it. It's just, it's like, we're just getting into the brain of Harry this morning. I love it. Yeah, it's horrible. That's why I try to patch it. Here it could close, although the ring gets in and that's just becomes, you know, mildew and everything is horrible. So, culture. Yes.

So I wish there was a better metaphor than sports teams because I don't know if that's fully inclusive of all people's perspectives, right, to make a truly representative metaphor. But it's one that I turn to those because I think it's most comparable and also one that I have most familiarity to. But like, so my ideal state of culture is one that, you know, is one in which the team is in a state of flow, right? That's, you know, the the thing that Gil talked about. And the analogy that I make to that is imagine that you're in a circle with your team passing a basketball around, you're passing a basketball everybody.

My ideal state for a team is to be in that state where you can pass the ball to somebody and not have to have them looking at you. Like there is that awareness of the other, so intimately that you understand where people are and can work together without actually having to be explicitly engaged there. And this is a state that you achieve and lose continuously. It's one that you constantly strive towards getting towards. And once you get there, you can be in there in some states and you drop back down. But that is the end goal that is elusive. When you meditate, you try to think of nothing.

And inevitably, thoughts creep in. But your goal is to think of nothing, quote unquote. So it's that anchor that you're trying to push towards. And my role as a manager is to be included in that circle to get the, to set the tone, to set the pace, to set the rules. And eventually, if I've done my job right, the team is in such a state of flow and passing the ball that I can't potentially step out of the circle and go into the sidelines to start coaching from afar and actually have my hands free to do other things and start planning rotations with the team and such like that.

Every so often I have to step back into the circle. Actually you know when the balls drop I have to step in there make sure that's picked up like that's my role but ultimately my role is not being there. It's just to make sure that the circle maintains its shape and its function. And that's my idea of culture. What? So I asked this to every, every guest in leadership. Why do you think IT leadership is so shitty? The plague of our ancestors. Back in 1776. Well, 1970, right when things got started. I mean, it's a very new industry. And it's one that's very past paced, it's one that there's no degree for, I mean, you can get a degree in computer science, but there's no like, like, you know, my mom is a structural engineer and she has to get certified every three, four years to make sure that she's not going to build a building that will collapse and kill people.

That is, there's no equivalent to that for engineering where something could make a leaky, a leaky application and all of a sudden your social security number is leaked and your identity is stolen. There's nothing to enforce a certain level of security and best practices there, which is bad, in my opinion. But it's also the great enabler of tech because you can also shrink towards extreme ends with insane outcomes that have, perhaps, non-desirable side effects. But yeah, so I think there's an element of newness there, a little bit of things being not, I'm not going to say in force, but not really, there's no sort of a case, I'm not sure what the word is, but it's still the world west as far as I'm concerned.

there's definitely more patterns and there's definitely more brute paths. But ultimately, it's also a weird endeavor because it's a very cerebral one that has not, it's a very technical problem space, but the process in which you create value is also artistic in many ways. So it's difficult. It's highly subjective. Yeah, and I think there hasn't really been a focus on making management good because it's just been a focus on just making things at all. So let's make things move forward. I think I'm curious for the rest of my career. Like I was an engineer now I'm a manager, I'm curious to see where the industry shifts as, how does the industry desire, like what priorities is the industry going to place on management in the future as well?

Like, you know, I would hope that my job position becomes more desirable later, like this is me being selfish, but, because there's always me need for, you know, I see individual contributors. Like that's always gonna be the need here, but I think there is more of an awareness of the impact and value that good management can have than also the interest that that management can have. So, and just another question that I consistently asked, talk about your journey of getting out of code, right? I know a lot of people struggle with that. I know there's a lot of developers out there. there's developers watching the show now in the future that are probably like, man, I wanna get into engineering leadership.

Like what's the one thing I need to keep in mind or need to be aware of before making that jump? What would you say? Prepare to do things that you have no skill in. I think there's like, for a long time, I want to be in product. So I think this looks like fun. They're, you know, they're talking to customers, they're playing like a roadmap. And then the more I learned about what product management does and why I was like, oh, they have to actually make all these documents. actually have to listen to customers for hours that end. They have to like, not enjoyable, not for me.

But on the engineering side, I was always curious to have like, I always enjoy hearing about the end result of what product wanted to do. I like to hear what we're trying to do, help into the roadmap. I didn't care about the preamble beyond that, which is the big part of the job in that role, I've done correctly in my opinion. Same thing with design, right? I like contributing and collaborating with design on there. And it's more like the high level areas of what you will be actually creating. Like I was never content to know what I was doing. I wanted to know why and how.

That was always my curiosity. And so me moving into management was a very intentional shift for myself. Like I know people have some kind of fallen backwards into it, which great, love it. Mine was a very intentional pursuit where I joined a startup that had a lead position opening and I think there's more, there's less friction in trying new roles in a startup because again startups just want things to be built and they will take chances more so than established companies that you know don't want to. So I got initial experience in a startup, the manager, and then was able to employ it. Booy, buoy that into a role at buoy?

Yeah, I think I'd like to share it. Yeah, I'm trying to take the SATs again to some practice thing. But then I was able to use that to spring important to MongoDB as manager as well. So are there as an IC, just kind of prove that I was a person and not a bad person. And then, you know, became a manager there. So I mean, the routes to be a manager are varied. You do it by accident, you do it intentionally. It's hard to do it by an internal transfer, which is harder to get promoted into there. But the, what's the core question? The biggest struggle, I think the biggest advice I can give is to truly understand what to manager does.

I think I've heard people in the past just desire to be a manager because they are in charge. They are the boss. And like, that's kind of where it seems their desire begins and ends. And there's no awareness of the shift in priorities and skills that are required that you are not taught as an IC. When you're learning how to, could react, you are not taught how to deal and work through interpersonal conflict on a team. I got this It's not what you learn, and it's when you learn on a job, obviously, but you have to be prepared to solve those as manager. So now a lot of people, you know, you just said, figure out what a manager does.

Can you give, again, it's going to vary with an organization, organization, all that, but high level, is it like 50%, like, can you break down super high level of like what an engineering leader kind of does on the day to day at all? Yeah, so when I was an engineering leader, I had two pivot words that I always came back to kind of center myself on what my day was going to be. Those two words are communication and information. My role as a manager is to communicate with everybody on the team. Internally they communicate externally as welcome team is doing. That's kind of the mouthpiece for that.

And it's communicating information and making sure that everything is kept in sync and coordinated there. manager still code, which is fine if you can do it, but you also have to make sure you do the non-technical sites as well, which is, you know, managing projects, not the code that makes up that project. You're kind of taking the higher up you go in management is the further you zoom out from the forest. When you are in IC, you are chopping down one tree in the forest. Now it is your entire world. You're focusing on that. If you're not the best swing, you know, you're measuring your endurance.

So as you go into a manager role, you're zooming out, and now there's multiple trees that you're watching out for. I'm like, you're helping people out, jumping back and forth. But that's your role, it's make sure that all the trees get chopped down safely and successfully. And then also communicating to the person behind you who's now staring at your group, but also other groups like myself as a director, I'm not looking at multiple clusters, making sure that all those things are being done correctly. So it's a lot of raising up information, but also delving down into the nitty-gritty details to make sure that things are being done correctly.

I love that. So, Bettina chimes in again. If you have any questions, this is the time where you can ask any hiring manager any question you wanted to. Bettina asks this, growing people's also key role of management. What are your thoughts, do you have any good thoughts around growing people? Like what is maybe your something you stand by in regards to training people up? Yeah, absolutely important. I mean, your best, your best senior engineers, your current NSC, your current non-sear engineer. You want to grow the team from within. It is also a role of yours to make your, the better you can make people on your team, the better your team becomes, right?

That's going to work all of up to. So if you yourself can't be that mentor, find somebody who can, whether it be on the team or externally. It's also interesting because not everyone has this similar drive to grow at a similar rate, which is also a challenge. Somebody may be focused on one aspect, but it's, you know, you're talking about people And people are, in my opinion, vastly more complicated than code. So vastly. And so tailoring the growth that somebody wants. And it's a two-sided problem too, because it's not only tailoring the growth needed for that person, but also matching it with what the team needs as well.

I mean, there's spheres. It's the individual to team the company. You're in the middle of that making sure that all ends meet. So absolutely as a manager, your role is to grow persons. And I always bucket into both technical growth, which is a little bit more cut and dry, like this XYZ. And then not to grow, which is much larger of a topic. People call it soft and hard skills, which I just go technical and not technical for use of that. And the non-technical skills are ones that are most influential, in my opinion, on your journey in your career and being able to become more experienced and scared because increasingly the code matters less and less and more is how you do the code and how you approach the code that matters more and more.

I love that. So as we wrap up here, y'all, if you have any questions, please ask us and I'll throw it up on the board. But I wanna finish going back to the job seeker, right? Because primarily, we're job seeker focused. What are just some last tips that you can give job seekers right now just in this market? This market's crazy. I mean, obviously, you're very well aware of that. Just what are some final thoughts for the job seeker today? Never give up. Never surrender. Except those like you, I think. What is that? Whatever. I mean, the biggest advice is honestly, to never give up, don't become demoralized, but also acknowledge that it is incredibly painful and demoralizing and exhausting.

Both these things are true. and to realize that your experience is shared amongst everyone doing so, from the person fresh out of a bootcamp to somebody who has 15 years experience. There is no decree that just because you have X number of years experience that the next job you get will be easy. You are still trying to find a match between yourself and what the company needs. And just like in dating, it takes to the dance. You need to, it's an decision that doesn't rest on their shoulders, no on your shoulders. And there have to be the aspect of luck where you both find what you're looking for while you're going through things.

So it's really just- You're about to write out the song right there almost. I mean, I got a disco ball above my head to- We're gonna turn this thing into a musical here in a second. Here we go. Catch two, the feline perfection. So, feline and good. Okay, what do I'm saying? Oh yeah, don't stop applying. Like even if you have good expectations for a job, like never stop until it's done until someone's singing, and it's not over. So, you know, it's hard. It doesn't get easier. You will get more used to it. You will build up calices towards rejections and understand more external, you'll understand the more external reasons why it didn't happen potentially.

You can also understand discreetly like fail this question, like that's a piece you think they answer why you do do the job. But if everything got went well, you still get the job, you'll have more context around like why beyond it. But don't give up, it is hard, it does suck. It sucks, acknowledge that, don't be shy about that. I had a senior engineer text me, literally this morning I'm reading it right now, man, let me tell you, I was not prepared for the emotional toll of job search. Yep, I mean, I have a friend who is an excellent engineer and just refuses to interview anywhere else.

but he was like, I hate it. I absolutely hate interviewing. And then I'd rather be able to be uncomfortable at my current job than go anywhere else and deal with that whole interview. Here's the process. There's a senior engineer I worked with, a large company, you know the company, they're here in Nashville, they deal with ticketing. Basically, he texted me and he goes, I almost wanna stay where I'm at because I am so over this process. And another senior engineer. And so again, listen, juniors, I know you all are watching right now and we'll watch in the future. Listen, it's hard there, but I have just as many senior engineers and senior folks like Harry that come to me and they're like, this is awful.

This is awful. It took me before Mongo. It took, it took me, I think four or five months went to, to finally arrive at Mongo when I was interviewing from start to finish. Uh, takes time. That's, you, you, I also like, you know, mentally prepare yourself, mentally and emotionally prepare yourself for what it will take. And expect it to take six months. Like don't sugarcoat it. Literally what I tweeted yesterday or the day before I said, the average is around six months. Yeah. So especially if you want to end up somewhere better. Like, yeah, you could say yes to any random job if you want.

Or you're not going to be bettering your situation potentially. So if you truly want to make things better for yourself, that takes time, focus, and energy. And it takes time. And that is six months. Yeah, I mean, literally, so to continue with this text, I said, I said, it's very hard, isn't it? And this developer goes, it is. And I was super picky this time around, which made it draw out longer, right? Which is going to hairy, like you have to be more intentional, but it's just going to drag it on. So you have to emotionally prepare yourself. Yeah, I have to. But that was my case as well.

I was very picky. When looking from my past job to Mongo, I wanted to find a well-funded seed round company that that could pay me an equitable salary to a fan company. So I don't know what the hell I was thinking. Uh, I came maybe close to a few times, but like, you know, you're looking at first 10 people on the job from a second, from a second round founder who has already proven himself successful. So it's a very unique constraints to look for. And they are extremely picky as they should be when they are including somebody else, because during from four to five, that's a huge increase proportionally.

Yeah, yeah, absolutely. Let's see here, full 100% passive looking for a job, only responder recruits reached out to me, took me about 10 months. So there we go. Yeah, there we go. I mean, pastor. That sounds lovely to be so absolute. I mean, I'd say like, if you're like, that sounds like, and again, I think right now that you can do that, I've had a lot of people message me and go, Hey, like what's the best way for me to be passive without like really getting after? Like for me, I think getting your resume on the job boards and I think updating your LinkedIn I think is probably the two most passive things you can do.

It's also funny because passive will then quickly turn to active. Like when you're going to fish in, you are, yeah, like you're going to fish in your lines out there. You're sitting there. You're going to beer. Also, when you hear a snag also, it's action, baby. Like you are go time. And yeah. So and again, and that's where too, and then Harry, I'll wrap up here, but because I won't take too much of your time, but again, that's why you have to be intentional on the front end to ask good questions because you're gonna have so many leads that if you're not asking good questions, you're gonna go down all these paths and get burned out much quicker, much quicker.

Cool. Awesome. Well, Harry, thanks for hanging buddy. I appreciate it, man. I'm gonna have you on, car. stay on for a quick minute real quick when I end this y'all. Thank you again for tuning in. Go connect with Harry on LinkedIn. I just did. So Harry accept my invite. And then other than that, I'll see you all tomorrow. So tomorrow morning, different session time. We're not, we're a little off, off face here. So noon central tomorrow. Hang out with my boys, Jimmy Allen and Ryan Burgess from Netflix. We'll be good when you want to miss it. Harry, thanks again, man. And we'll chat soon. Hey, you did it.

You listened to an entire episode, and I am very grateful, because you know why? There's a lot of podcasts out there. There's a lot of episodes, and I myself rarely finish an entire episode, so I appreciate you so, so much for listening. Quick reminder, please rate and review this podcast in the App Store. I want this to be discoverable to others, and the only way that happens is if you take the time right now and rate and review it. Please, like, right now. Unless you're driving, then don't do it. So, thank you again. If you need to reach out to me, Taylor at Vaco.com, or at Tdastin on all social media handles, and I hope you have a fantastic day.

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