Soft Skills Engineering - Episode 150: How to fight imposter syndrome as a technical lead and Getting in to meetups

Episode Date: March 25, 2019

In this episode, Dave and Jamison answer these questions: I worked for four years doing web development for a company while I got my degree, and loved it. I eventually became the lead developer because I had been on the team the longest. I thought it was really cool. I worked with the team to make organizational tech decisions, trained new hires, held regular meetings to discuss projects. After about 6 months, though, imposter syndrome started sneaking in and I felt like I was making things worse, not better. I figured the team needed someone who actually had senior level experience, and the pressure was getting to me. So I bailed. I’ve since had a few people approach me and say they want me to join their early-stage startup in a technical leadership position. I haven’t outright declined, but I’m nervous about being put in a position where the stakes are even higher. My question is if the pressure of being responsible for everything ever lessens. Is it something that gets better as you get more experience? Is everyone in technical leadership feeling this pressure and doing a good job to hide it? What can I do to gain the confidence to eventually lead another team? How do you step into the meetup scene? I have not attended one before, but the idea of them is interesting. However, there is this feeling that I would not fit in due to inexperience.

It takes more than being well-known on tech Twitter to be a great software engineer. This is episode 150 of the Soft Skills Engineering podcast. I am your host, Jameson Dance. I'm your host, Dave Smith. Soft Skills Engineering is a weekly advice show where we answer all of your non-technical questions about the technical field of software development. And you know it's good, because we're well-known on tech Twitter. But are we really?

No. We're not that well-known. No. We are known exactly the amount we deserve to be known. Yeah, which is how it works on tech Twitter, right? like people have the right number of followers for how good they are at technical things it's directly correlated yeah you just look at we were talking about this before the show you just have to reduce everything down to one number and make that number go up that's right so there it is

that's the number better developer make that number of followers go up my twitter follower count actually matches my weekly bug rate uh in oh i write thousands of bugs per week it's the cost of being outrageously productive i know rockstar programmer yeah i just i just throw four loops at the wall and see what sticks can you believe that this is episode 150 no we've never acknowledged any milestone because we're scared to not we didn't do anything special but that's still a that's a big round number good work dave has a zero at the end yeah those are good numbers i've mentioned this a couple times on the show but honestly when we started this idea i thought there's maybe three or four

maybe six episodes of material in this universe we are sitting on a question backlog of hundreds of questions that we haven't gotten to yet so we're not going anywhere people if you hate this show we're sorry because we're still going yep not until we have it all figured out we are a while away from that we're like weeks away from that at least yeah we're at least two weeks away from finishing this show which is how all my software estimates work uh do you want to thank our wonderful patrons yes thank you for those who are supporting us on patreon at the level where they get a shout out every week that's matthew voidovich the agile ventures charity zach grannon luis santos nick cantar sean clayton good old sonic the hedgehog marais rousseau and chris

hogan thank you so much if you'd like to support us tell them where they can go jameson they can go to softskills.audio and click the support us on patreon button i have uh i don't know if we want to edit this out or what but actually marie rousseau dm'd me and said you pronounce it as marie and also don't worry about my last name so i assume that means we've been butchering it so much that he's given up hope that's right they are clearly not qualified to pronounce my last maybe next year maybe next year marie will write in and say and now you get to learn how to say my last name you've proven worthy thanks moran i apologize for all the times i said your name wrong i only apologize for this time because that's the only time i knew but the rest of the

time i was just doing my american best uh yeah let's get into the questions all right should i read our first one yeah please do okay this comes from alex alex says i worked for four years doing web development for a company while i got my degree and i loved it i eventually became the lead developer because i had been on the team the longest which is the the best qualification for promotion to tech lead well alex has been here the longest okay all right alex goes on to say i thought it was really cool i worked with the team to make organizational tech decisions i trained new hires held regular meetings to discuss projects but after six months imposter syndrome started sneaking in and i felt like i was making things worse not better i figured the team

needed someone who actually had senior level experience and the pressure was getting to me, so I bailed. I've since had a few people approach me and say they want me to join their early stage startup in a technical leadership position. I haven't outright declined, but I'm nervous about getting put in a position where the stakes are even higher. My question is, is this pressure of being responsible for everything ever lessens? Is it something that gets better as you get more experience? Is everyone in technical leadership feeling this pressure and doing a good job to hide it what can i do to gain the confidence to eventually lead another team that's a good question uh it's like the nose game method like whoever puts their finger on their nose last that

person is the technical lead someone's looking looking down at their phone they look up and go huh the tenure does sometimes correlate with experience especially at startups where there's yeah i don't know it's not the worst way uh and i assume that wasn't the only reason too it was probably because probably because you know what you're doing one thing you should know about me is that when i was in a director role i put a college student intern as a technical lead of one of my teams so you know you're like right in line with my with my philosophy all right go work for dave uh i felt like i was making things worse not better that's a really interesting feeling i feel like i feel imposter syndrome sometime and the form i feel it in is um i don't really know what

i'm doing or how to solve this problem and i assume other people do and they're just kind of like sitting there with their arms folded saying will jameson figure out the thing i already know that he should do but it doesn't usually come in the form of me feeling like i'm actively making things worse and i feel like i i i try to i think i can notice tangible results based on my efforts and that is one thing that helps kind of combat the feelings too it's like these people are happier now that i'm here or we got more done or there's a higher standard for quality or um wait a minute all kinds of different things you decided three things that are not measurable how do you how do you know they got better i just feel it i feel it in my gut dave okay i don't know the gut the gut

ometer yeah it is heavily gut based um people being happy you can just ask them are you happier or less happier than this same time 12 months ago yeah yeah do some uh do some audience surveys i that's probably a separate discussion how you measure those things but i think it it part of what you do as a team lead is is uh well this depends wildly actually but some of it might involve solving kind of like organizational or problems or team wide problems and you should be able to say like my efforts are having an effect or not so some of it could be kind of looking at the results of your of your efforts instead of just going with this feeling of like i feel like i'm not doing a good job yeah and and i can say that from my experience this feeling of

not really knowing if you're doing a good job uh it actually never really goes away i think and once in a rare while you get a glimpse into something that tells you yes you're doing a good job or no you're not but i still remember the first time i stepped into a management role full-on people management this is after years of technical leadership i stepped in and i'm just like, okay, I'm here to learn, figure out what I can figure out. And then after a year, my CEO asked me, how are you doing? Like, do you feel like you've learned and you're performing well at this point after one year? And I said to him, I have no idea. And this is after I'd been in the industry for over 10 years in various leadership roles, technical leadership roles. I still had nothing.

I just had no idea. Did you think you were doing a bad job or you just really had no idea? Like, did you feel like you were doing a bad job but weren't really sure or did you just feel like i could be doing an amazing job or i could be horrible or i could be fine i think this yeah it's kind of a little bit of that all three like i think though i think the spectrum leaned towards more like i know i'm not doing a terrible job like my team hasn't all quit my you know the building hasn't burned down we haven't had any major outages and you know the on-call rotations are functioning properly and you know we're getting customer issues dealt with in a timely manner so you know like that stuff all pretty good um but then the big question was like are

there huge things that i'm missing and that i'm not doing yeah uh and i felt like there were i just didn't know what they were nervous about being put in a position where the stakes are even higher i think there's probably something interesting to explore there the pressure getting to you and this and worrying about the stakes being even higher i feel like in my experience the times where i've learned the most have been times where i felt like i don't think i've ever been somewhere where i felt like i was utterly incapable of doing the work i think that would be a hard place to learn but the times i've learned the most have been where i wasn't sure if i was capable or not but the gap wasn't so huge that i couldn't imagine a world where i could do

it um so there is some amount of fear of like maybe i can't do it because i haven't done this kind of thing exactly like this or in the same situation before but if someone could do it and they knew they could they would probably hire that person instead so i don't know i think i think you can take people's word for it if they say they want to bring you in i think there's a big difference in the pressure that one feels in these two scenarios where on the one hand it's like who should be our team lead uh alex you've been here a while maybe you could do it and alex is like sure as opposed to we deliberately made an offer to this person person to join our company and be our technical lead it's like oh boy i gotta you know i really gotta step up to that on the first

in the first situation you can always just say look i i didn't really sign up for this i just fell to me because i was the person who'd been here the longest like pressure's off right whereas in the second situation it's like this company interviewed me made me an offer with the title on the paper of technical lead and now i gotta live up to that yeah yeah i guess that makes sense in terms of a different amount of pressure do you think alex mentions technical leadership a few times do you think that they mean literally focused purely on the tech or does that mean like engineering management i think in this case it's tech yeah it's kind of like yeah lead lead developer yeah more more senior developer type thing um i'm a position where the stakes are even

higher i mean i feel like there's a lot of stuff you could say to that um there have been a lot of successful companies built on poor technical foundations uh and and given perfect knowledge of the past and the future you could maybe argue maybe there would be more there's probably some companies killed by bad technical decisions too but i feel like very rare yeah i feel like it's pretty rare and if you're trying to do good work that counts for a lot of things if you're looking out for mistakes and trying to learn from them and trying to fix problems as they come up like i don't know there's there's a pretty wide spectrum where someone can be effective uh if if they care yeah so caring covers a lot of potential issues i just when you said

companies that fail because of technical issues i just had this thought in my mind where it's like hey how's your startup doing oh man we totally flamed out and failed oh what happened we just couldn't figure out our database pooling we've got to shut down the company yeah i mean maybe like velocity issues where you can't get features out fast enough or something but yeah i think and and i'm sure uh magnolia do you remember that bookmarking service no they they were a yeah bookmark tracking service where you could save all your bookmarks and they lost all of their data all of it and and didn't have any backups or lost all their backups or something they just lost everything and we're like well i guess our company is gone okay that's just shut the company down

but uh i think that's pretty rare i think the other the other way this manifests is in a second degree effect where you have or a second order effect where you have really bad technical decisions that lead to a quagmire of a code base you have to work in that causes developers to leave because they're like this is terrible i don't want to work here so it's kind of like a technical decision that manifests in the business so have have you ever worked somewhere where you felt like you know the code here is really good because i i never have yeah and maybe it's just maybe it's just acclimating to your environment and and kind of like not seeing all the things that are working well because it pains me personally when there are issues in the code

especially if a customer uncovers something caused by it i'm like oh i just feel it so deeply but i feel like everywhere i've worked the code has been about the same level of duct tape together and it's just like that's what production code is everywhere it's it turns out that there will never be enough time to do it right and well and everyone knows all the requirements up front and yeah i don't know so what you know you've been now in a management role for a year or so and various technical leadership roles what are the main differences between how you run a team today as compared to a few years ago when you had never or when you were just starting out i think i am much more comfortable setting expectations and holding people to those expectations

i think that i have a better understanding of how and what to push on to the team and what to do for the team i think when i first started out i was just like well i i do everything i guess i just do do everything for everyone all the time whenever they ask yeah and and yeah so maybe a little bit more focus and i've seen enough things um go wrong both from my part and from other people's part that i feel like i'm a little bit more calm about most of it i i mean if you've listened to the show you know that i'm prone to stress sometimes yeah uh and and when i first started yeah years ago i i took a i've kind of told this story before i i like lost the nose game at a startup and had a like people and technical leadership position and and i was just terrified

and stressed out all the time of like um if i make a mistake then we're doomed and i've made a lot of mistakes and we haven't ever been doomed so there's kind of just this broad feeling of like yeah there'll be a lot of stuff that i don't know how to do and it'll probably be okay as long as i it's kind of like the flip side of the that thing i mentioned earlier where caring and trying counts for a lot um and and seeing that it counts for a lot has helped me relax a little bit that's cool which if people know me now they're like you say you're relaxed but uh compared to what i was yes really yeah to me you've always struck me as relaxed oh well relaxed is maybe the wrong term easily i i'm less easily stressed out okay that that i can handle yeah that makes sense yeah okay

I mean, for me, I think one thing that I've learned is to, to more easily identify things that are important and unimportant and to recognize them as such, rather than thinking that everything is important. Kind of like you were saying, you know, do everything for everybody. Do you, do you have an example? Yeah. Like, okay, here's an example. You know, what kind of, we're right in the service.

What kind of dependency injection framework should we use? And it's like, uh, I don't know. I don't think it really matters. you know like at the end of the day um i don't think it makes a huge difference and it's the kind of thing we can undo if we find out that it's bad uh without too much effort so you know that kind of thing whereas like one of my co-workers comes to me and says i'm considering quitting okay that's important we should talk right yeah probably whereas i think you know younger dave might have said these two things are equally important yeah okay i could see that

that makes sense um is everyone technical leadership feeling this pressure and doing a good job to hide it yes i don't know if everyone is but i certainly do yeah you feel it or do a good job of hiding it uh i feel it i do not know if i i guess i am admitting it publicly so i'm now doing a poor job of hiding it yes what can i do to gain the confidence uh that i think a lot of that is just experience yeah i don't think it's something you can do outside of leading a team that will give you the confidence to lead a team yeah like no matter how many business books you read you're still going to be not confident until you've been through it yeah but i read turn this ship around why is it still hard i know everything i need to know commander whatever his name said

that i had to empower my my poop deck swabbers or whatever they are and then the nuclear submarine would work effectively that would be like i don't know the business analysts or something you got to translate all of the navy positions into scrum roles on your team one you know one of the benefits of getting old is that the people that i knew when we were young careless i mean sorry when we were young carefree fun-loving kids are now in these positions of responsibility but i knew them when they were young and carefree and so it makes me realize like wait a minute that guy doesn't know anything and he's a cto so i think the answer is uh basically like no one is great at this and um you don't have to worry about it like and and also everyone

above you on the pecking order they all secretly know that they were once just like you and still frankly still are but they've just learned how to kind of hide it and they've learned what's important what's not important and how to do their job uh in a way that makes them successful otherwise they wouldn't be in that role unless they're the son-in-law of the founder which slightly different story but but like they know they understand it and then i think the other thing that really helps me is that when i was in a director role i wanted to get feedback from my people so bad and i remember i would dedicate significant portions of my one-on-ones with lots of people to ask open-ended questions like, name anything we should change. You know, what should

we change? Is there something in our architecture, in our organization? What do you think we should change? And nine times out of 10, they'd be like, I don't know. Yeah. Like, isn't that your job to figure it out? That's exactly right. Like people just, I think people spend a lot less effort thinking about how bad of a job you're doing than you think when you're in a leadership role. Yeah. I'm trying to think about technical leadership that I've had. And I feel like most of the time i'm i am a lot more focused on my own work and there's there's maybe a handful of times where i feel like i just really wish they would not do this thing or would do this thing uh and past jameson has mostly just ignored having those conversations i think i'd maybe

approach him differently now but i think i've also come to appreciate how nuanced and complex these situations are and so sometimes when i say that was the wrong decision and i'm referring to like a leader somewhere in the org chart up above me i think i now appreciate that that leader probably had 12 other things on their mind as well that complicate this decision so much more than i appreciate right now um so i i mean this is like me saying i'm a good follower because i've been a good leader or sorry no that's not true i'm a good follower because i've been a leader good or bad don't try and guilt trip me and take away the time-honored salve of complaining about how dumb all the people in charge me are that's that's a it's like a worker's right

those high muckety mucks don't know what it's like in the real world yeah uh yeah have we answered the question i think so i say go for it everyone's flying by the seat of their pants jump in there's no way to get confidence in this role except getting in the role and getting your hands dirty yeah all right i will read our next question this is a short one from an anonymous listener how do you step into the meetup scene i have not attended one before but the idea of them is interesting however there's this feeling that i would not fit in due to inexperience interesting so uh i believe what you're supposed to do is you stroll up to those swingy doors but the saloon style swingy doors your spurs click against the ground you step in the player piano

stops itself i guess everyone turns all the dirty haggled not haggled haggard faces turn and look at you and then they all turn back to their drinks and music resumes music resumes yeah it's kind of like that you have to prove your cowboy or cowgirl credit and that is literally how you step into the meetup scene yep the click of your spurs what a what a masterpiece and a steely gaze i can tell you've been reading fiction recently all these great verbs yeah uh i've not attended one before i'm trying to remember my very first meetup i ever went to i think it was a ruby meetup um and i felt weird i didn't know anybody i was a student and i feel

like most of the people there were professional working developers so they were on average older than i was uh like 12 months i don't know looking looking back i swear they were all 40 and titans of industry but yeah this so this was uh maybe a few months into me learning how to program at all so i i really didn't know anything or have any experience i just heard ruby was cool and heard there was this meetup thing but i didn't really talk to anybody but no one was mean to me i don't know i just sat and listened and i actually met there a guy that i later worked with who became a friend even though we didn't really talk very much then i just listened to him talk about protocol buffers and then like four years later i was like weren't you that guy

that talked about protocol buffers one time i was hiding in the corner too shy to talk yeah this question kind of presumes that there's some kind of experience bouncer standing at the door being like what six months get out of here kid yeah there's someone with a yeah like this test of a true developer or something yeah and and of course there is an implicit test when you start opening your mouth uh but you don't have to open your mouth you can just or you can just ask questions well if you're really worried about looking inexperienced that's true it might be hard to ask questions like what does that thing you said even mean but there i think i think the real situation here is that at most of the meetups I've gone to I would say more than half of the

people there are extremely inexperienced maybe just barely starting out maybe even just having a desire to learn how to program so not only not only are all the things Jameson and I have said so far total fiction but in fact you might find that you're not even on the lowest end of the experience level at the meetup so I've felt that at JavaScript meetups specifically where there's a large um especially around here there's a lot of boot camps and the boot camps heavily encourage their students to attend meetups and their graduates as part of networking and finding a job i haven't felt it as much at other other technology or programming language meetups i've been to ruby ones and go ones and general distributed systems ones uh some other ones too

and it felt like those are um all of the ones besides the javascript meetups felt like there was a smaller group and it was more experienced people in general yeah that makes sense so it could maybe depend on the on the technology and they were all very welcoming none of them was forbidding one of them was at some guy's mansion in the mountains that was kind of weird but it was welcoming um it was just weird to be like sitting on this rich guy's couch if you can learn ruby as well as i have all of this can be yours yeah it was a bizarre experience uh i feel like there's also so there's the technical experience side but there's also just the social part of it where you're going to this group of people who you

assume all know each other and it's hard to meet new people and it's especially hard to be the outsider of a group and even harder if you feel like you maybe don't even qualify to be a part of that group i i could see how that uh that could be the case um what would i do if i were in that situation you could reach out to the organizer and say like hey i'm thinking of coming uh and just kind of introduce yourself if especially if they're on meetup.com or any other website there's a there's an easy way to find out who organizes the meetup and i i feel like people that organize meetups are generally very interested in community and welcoming people and growing their their group yeah so i think you could kind of intro yourself to someone there and

make a connection so you're not just going in cold without knowing anybody yeah i'd say outside of like bay area insane meetups or new york city insane big meetups most organizers are more concerned with growing their group than they are limiting who can come yeah that's true those are a whole separate category they're but they're basically monthly conferences yeah um and are very high demand and and this the talks are kind of a different style and quality and caliber yeah i'm thinking about like brooklyn js or waffle js or all those all those rad sounding ones that someday i'll go to i like your idea of reaching out to the organizer just to get a sense for what's going to happen there before you show up um yeah i think that'll be a big confidence booster

and i'll bet you 99 of the time the organizer says hey happy to have you come say hello when you get when you get here and i'll shake your hand and introduce myself to you yeah most meetups i go to are are in the order of dozens of people like like low single digit dozens yeah like five to like 30 people are almost all of them uh i i'm trying to think too i organize a few conferences of several hundred people and have had attendees reach out like that before and just been super interested in meeting them and talk to them when they got to the conference and there's just something about when you're running this group you just i don't know you just want to make people feel welcome so i think that would help you could bring a friend too oh yeah wingman yep although uh

i think i have seen that happen before and i've i've noticed people come new i used to run a meetup for a while for several years and there would be um people that would come with a friend and if both they and the friend were new they would often just kind of split off by themselves and then the problem would change from i don't know anybody so i won't talk to anybody so i don't know anybody so i'll just talk to my friend yes the whole time yeah um and i mean you can do whatever you want you can still do that and at least you're going but also if you do that um try and use it to break into meeting new people instead of just sitting back with your friend i love it well we answered i think so the answer is just go yeah just go wear your spurs uh be

prepared to draw down practice bringing the brim of your hat up and down so that your eyes the slits of your eyes just peer out from under the brim yeah if you get that wrong it looks really dorky let me tell you your hat is it's it's not your eyes peering out you just literally can't see anything and you run into the post and then when they ask you if you've heard about this new javascript framework which is the equivalent of drawing down you won't even be able to stare them in the eye good luck it's it's the wild west out there no it'll be friendly uh what should people do if they want their own questions answered hit us up on softskills.audio and click on ask a question thank you so much to those who have done so we are overwhelmed inundated one might say

metaphorically with questions we really appreciate it keep them coming yeah thank you we'll catch you next week