Soft Skills Engineering - Episode 338: I am the golden handcuffs and Staying in management

Episode Date: January 9, 2023

In this episode, Dave and Jamison answer these questions: Listener Mattoosh asks,‌ I’m the last remaining support specialist on a really old, not actively maintained, but still lucrative SAAS product. I’m stuck. As a front end engineer I want to work on other projects within my organisation to gain contemporary framework skills, but nobody can backfill my workload. I know option A is “quit your job” but what other options do I have? ‌ I started my journey as an engineering manager at a startup. Over my stint, the company grew and so did the engineering team. Overall I received good feedback from the engineers but the founders didn’t recognize the value of this role and I felt that I wasn’t getting the required mentorship there to grow further. I ended up quitting. It’s been challenging to find another manager role. I get good feedback from the interviews but haven’t received an offer yet. I still am a good backend engineer but that is not what I want to keep pursuing. Appreciate any thoughts or suggestions on what I should do to bag one of these interviews as I don’t get that feedback from the panel. I don’t miss any of the podcasts and do enjoy the show.

it takes more than being in 130 slack channels to be a great engineer this is soft skills engineering episode 338 i'm your host dave smith i'm your host jamison dance soft skills engineering is a weekly advice podcast about all the non-technical stuff that it takes to be a great software engineer including managing all your slack channels did you count how many you were in no it sounds like a very exact number yeah i would not be surprised if it's bigger than that yeah because it depends on so many things are you in other organizations if you use it for work and for other things and do you kind of like lurk in a bunch of channels but you mute heavily or i don't know i feel like there are like i'm trying to think of how many i pay attention to

there are probably like 15 different channels i pay attention to during the work day which is kind of crazy right like it's a lot yeah that's too many i don't know how we got here we should all go back to email i know i feel like i've heard you talk about this before i have my former co-worker of mine said that the way the best way to describe slack is oh i heard you like inboxes yeah does that mean we've reached grumpy old man status like there's a newfangled slack thing yeah totally all right i want to thank our patrons thank you to the folks who contribute to the show financially at the level where we shout them out every single week thank you to valentin at datafold santa hopar noah frazier loge kent c dodds memester josh jenny kim owen shardle craig

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these names will represent a significant percentage of what historians know about this time period so join now if you want to leave your mark on history yeah all knowledge except the archive of soft skills engineering has been wiped out for some weird reason this sounds like a dystopian bill and ted's excellent adventure variant yeah good thing we're etching these into titanium plates yeah and then putting them in orbit around the earth right do you want to read our first

question dave yes this comes from a listener named matush who says i am the last remaining support specialist on a really old not actively maintained but still lucrative sass product i am stuck as a front-end engineer i want to work on other projects within my organization to gain contemporary framework skills but nobody can backfill my workload i know option a is quit your job but what other options do i have i like option a look i already know the very first thing i should do quit my job there's a okay i want to summarize this question help i have an enormous amount of leverage over my company what do i do that's a really good that's a really good way to put it i am the only person in the whole company who can do what i do usually the only time you

have leverage is when you're trying is when they're trying to hire you right we're not the only time but you know what i mean that is the highest leverage moment in your tenure with any company is when they have not yet hired you and they want to hire you so so you're saying look i understand you're not getting the professional development that you want you're not using the technical skills that you want to use or grow but why not console yourself by asking your company for a lot more money it could be that yeah it could also be i mean there are other ways to to compensate you or reward that leverage besides money yeah you could say you need to rewrite it all like pick the thing you want to learn as a way to forever tarnish the reputation of developers

in in this area in the future like no never again will they trust a developer you could so i'm trying to think of things that make this better for the company like if you quit they're gonna have to train someone anyways but they don't have to yet because you still work there so like why would they why would they now just because you say please are you saying you have to threaten to leave to get any emotion here maybe i don't know if i'm trying to figure out what i'm saying by saying it in real time nice i can't see any problem with that let's proceed well you're kind of in like an impasse because it's going to cost the company more money to change anything right like either to swap someone else out with you because you quit or because you

want to move on to a different role and they need to train someone up into your place so like you do have a lot of leverage because there's a lot of money tied to this sass product but also i don't see an option that is better for your company besides like wait for something to change like the best option for your company is you just keep doing what you're doing yeah exactly anything different uh yeah we're gonna just keep using you you're so great we love you is there anything we could do besides changing anything right any words that we could say no actually quite frankly giving you a big fat pay raise would actually probably be the easiest thing for this company to do like yeah of all on all the list of things to do like training a replacement

that's the whole list i can there's way cheaper than training a replacement yeah we'll give you a 20 raise you'll be happy we'll continue to be happy and there's there's probably an amount of money that this company would pay to make this problem go away by which i mean that this problem being having to go find someone to train and do this because also finding your replacement is going to be very hard for them like imagine what it would take to get someone who has never worked in this code base who doesn't want to work in this old legacy non-interesting code code base and ask them to be the the support engineer that's going to take a considerable amount of money they might have to go to consulting rates for that you know they could be looking

at 200 an hour to support this thing yeah with that as your backdrop i think you can definitely i mean that's that's some good leverage because that's what that's what they're competing against and i think they know that they have a massive bargain in you and i'm making some assumptions here but they probably know that better than you do i feel like the way we're talking about this question reveals something about our worldview because the question asker said how do i change to do this other kind of work that I think will be more fulfilling. Yeah, and we're like, you just need more money.

But money, yeah. What if you instead got more money to do the same work that isn't fulfilling? Yeah, I know you asked for more fulfilling work and better technical skills, but look, money solves everything. If you have nicer shoes while you're doing the less fulfilling work,

won't that be the same? Okay, let's set the money topic aside for the moment. I just thought it was an interesting observation that sounds like this question asker may not have considered. And I think a lot of people don't consider how much leverage they have over their employer when they are in an indispensable situation like this. So, okay. If it's okay with you, Jameson, let's set that aside, the money part. It's okay with me. It's very, very hard for you to do right now.

Well, I can set aside talking about money. I just can't set aside the money. Okay. I will keep the money close at hand, but talk about other stuff. I'm thinking here that the way to approach this question with your company about, hey, how do I get into greener pastures and do skills, work on skills that I actually want, is to couch this, to frame this as a existential risk to this product. because your company has a, what do we call it, a lottery factor that's really, really easy to trigger here because they have one person who knows this. And so this is a business risk that they have taken on and maybe don't fully recognize the risk. And so rather than going to your company

and saying, hey, I'm going to quit unless you let me advance my career in these ways with these other skills, you could go to them and say, I believe we have a business risk that is too high to maintain this product offering for our customers. And I'd like to propose that we cross-train someone on this product and we share the support load between the two of us so that A, we have better support capacity. B, we have redundancy in case of lottery factor stuff.

Or C, there is no C. Sorry, I thought there was, but there's not. Think of a C. We'll leave that to you. Yeah, that's an exercise left to the listener. it always sounds better if there are three things it does two things right rhetorically it's very important that there are lists of three yeah yeah i like that idea a lot you are that that's that's a way of reducing risk for the

company you could also talk about it as like reducing the cost of support maybe that means more documentation like there could be some upfront investment work that you put into this product to make it easier for others to pick up or even or even easier for customers to self-serve the support yeah yeah and if if you can make it cheap enough to support then presumably that means there's other more valuable work you could do instead like you you could one case is that you do such a good job that they don't need you anymore which is not great right risky news you'll get to go find more fulfilling work also a risk yeah but also there's probably other important stuff to do most companies have lots of things that they would like to do that they

cannot get to so if you can make the cost of supporting this product low enough in time or or i don't know in specialized skill set then then there's there's now somewhere more effective where your time could be spent does that make sense totally higher value activities so there there is up there is opportunity cost for the business to keep you in this role which is that you can't be doing more valuable things to the business like learning new frameworks right like think about how valuable it will be to you if i spent several months learning elm yeah there's a name i haven't heard in a while yeah i was trying to think of a haskell equivalent of a front-end framework that's like yeah pure script but buckle script i think is it is somehow related to pure

script in a way i don't understand and then what's the other one reason ml oh yeah those are all the mle type languages i i think i am aware of in the front end you just proved your credentials good job thank you i feel like you nailed it have we answered the question i think so like a you've got a lot of leverage if you want more money b and remember there's going to be three here so I'm working on getting the third one as I talk. You could make more money if you wanted to. B, you can catch this as a business risk that the company needs to mitigate.

And C, again, exercise for the listener, but I'm sure you'll come up with a good one. I actually know C, but I'm not revealing it because it's a pedagogical technique where you have to figure it out and you'll be better off. I mean, what if the C they come up with is way better than yours?

You don't want to... I mean, that's unlikely. The C that I'm thinking of is really good. I'm not thinking of a C. I don't have anything. All right. All right. The secret is revealed.

You want to read our next one? Yes. Now I'll read our next question. This is from an anonymous listener who says, I started my journey as an engineering manager at a startup. Over my stint, the company grew and so did the engineering team. overall i received good feedback from the engineers but the founders didn't recognize the value of this role and i felt that i wasn't getting the required mentorship there to grow

further i ended up quitting it's been challenging to find another manager role i get good feedback from the interviews but haven't received an offer yet i still am a good backend engineer but that is not what i want to keep pursuing i appreciate any thoughts or suggestions on what i should do to bag one of these interviews as i don't get that feedback from the interview panel i don't miss any of the podcasts and do enjoy the show nice that's one piece of advice we can't give then don't miss any listen to every episode surely something in there we make no guarantee express or implied about the outcomes of listening to the show though throw this incredible amount of spaghetti at the wall even even more spaghetti

i'm glad you listen and enjoy thank you that's nice of you to say yeah thank you let's see engineering manager roles this is a tough time for that just economically i think that if any role gets squeezed to do more with less it's management i feel like there are a bunch of roles who are like wait a minute my role gets squeezed more to do with less but yeah i'm sure you're right i'm sure you're right i think i think i see your point yeah it's like here's my point it's like if i'm a super hyper growth startup that's just hiring like crazy i'm also gonna to hire a bunch of managers in that same time frame. I might even hire ahead of time, but only if money is abundant and growth is an imperative. Whereas if I am a company that's being, the budget

is being squeezed, money is a little tight. And I'm thinking, well, I've got an engineering manager who currently manages eight people. I need to hire two more. I'm sure they can just do 10. you know yeah it's like uh and maybe 11 and maybe 12 you know it's like and so or even it like if you have an engineering manager who quits it can be tempting to say well what if we just like smush teams together instead of replace them yeah absolutely it's like you can manage 17 people right that's what mr musk said it is very tempting to do that because i think a of hiring less management is a little bit intangible and a little bit hidden from the people making that decision you know like yeah everyone every individual team members

professional growth and experience at work gets a little worse but yeah you know the bug rate in the product might not change the you know that the economics of your product might not change that much but everyone's just a little bit unhappy you know yeah yeah things are like a little more chaotic and there's yeah and you're like well that's that's the trade-off we chose we chose a little more chaos you know yeah and there can be good reasons for choosing that right so i i guess what i'm saying here is uh jumping from an engineering manager role at one company to an engineering manager role at another company is probably one of the more challenging roles to get as a job seeker i think as compared to like back-end engineer front-end engineers like

great we need one of those we'll hire you you know yeah i feel like you you switched points there from economics to like in general it's harder to get a another engineering manager yeah i think i do think i don't know if it's strictly harder in general to get an engineering management job there are certainly fewer of them just mathematically fewer of those positions open at any given moment but right now for sure in the current economic situation i think it is starter even in the before times when interviewing for those roles both for for my own sake to to get one of them and also interviewing to hire an engineering manager i feel like i've i've done a lot more interviews like the ratio of candidates to hire yeah the ratio of yeah yeah yeah it's

higher yes would you say it's like twice as high five times as high one thousand times no i would not say any of those because i don't know oh okay it's more more times as high okay i don't know it felt like maybe like five we had a really long search for one candidate um but so that might be an outlier yeah so so it it might just be it takes more interviews it takes more more tries to to land this role yeah i also think there's there's a bigger emphasis on fitting in with the company style culture i don't know structure yeah where i think it is generally easier to hire i think i guess you said this earlier it's easier to hire a a developer and say you might have different experiences but like your skills will transfer fine yeah i mean you could have they

solve the whiteboard puzzle so they're qualified you know yeah it's like a little more concrete yeah but the the breadth of problems and philosophies to solving those problems in engineering management and and like the orthodoxy is is just so poorly established like there's there's just so many different ways people think about doing it that i don't know i feel like it's easier to to show up and say here's how i think management should work and and see a lot of like people recoiling in horror and saying what yeah no we don't do that you know yeah Yeah, I agree. And the way that I would summarize that is that it's a little more fuzzy about what makes a good engineering manager. And like you've said, you just kind of have to

click with people in the interview sometimes. And that's a much harder roll of the dice than, oh, look, I implemented iterative Fibonacci in linear time with memoization. Therefore, hire me. It's harder. Yeah, like I communicated well about my code while I did it. So you think I will be able to solve hard problems well. I think another way to put that is if you thought the software engineering interview process was unreliable, non-deterministic, and inconsistent, well, boy, have I got some news for you. And I think the point that we're trying to make here is that it's not unexpected for you to get into a situation where it's challenging to find your next role. That's pretty normal. So what do you do about it, though? And to me, you need to develop

well let me back up and say it this way the best engineering manager candidates that i have interviewed have a very crisp management philosophy and very concrete tenets about how they approach a wide variety of different problems you know like i've been asked in management interviews what's your what's your philosophy on performance management and you know it's like oh i don't know i guess i just you know like help people perform good you know it's like that's one answer right or you could have a very crisp answer where you based on experience where you can actually cite examples of times you've helped people improve their performance or that you've had to manage someone out of an organization yeah and i think that it's harder to have those answers off the

top of your head because there isn't just it's not something you work in every day like it may have been six months to 12 months since the last time you encountered a performance challenge as manager and there's no leet code website where it's like okay situation you know solve this problem and then you have to type out an answer although you could probably build a chat gpt variant that would actually interview you for a management role and assess you based on what you type in your answer which would be really cool yeah anyway so that my advice to you is make sure that you have a portfolio of answers at the ready for common management questions such as what's your philosophy on performance management what's your philosophy on compensation what's your

philosophy on team organization? What's your philosophy on how to work best with product management? What's your philosophy on working across teams and building consensus? What's your philosophy on you being the tech lead versus having a dedicated tech lead on the team? You know, like, these are all things that you should have an at the ready, very succinct, crisp answer for. And I think you'll do better in the interviews. Now, that's not to say you'll get the job. Because again, your philosophy might not actually align with the with the company's philosophy, at which point you won't get the job. But at least you'll, you know at least you'll have a crisp answer so that when you do find the company that aligns well

you're ready to go they might not even have one too but they might not and that's one of the reasons i say have a concrete answer because sometimes what a company is looking for is someone who has a clear framework for operating as a manager that they can articulate to the interviewer they're like oh this is great our current managers just kind of wring their hands and are indecisive and don't you know they don't know they don't know what their own philosophy is but if we hire this person, they just kind of do stuff. Yeah. I love that answer. That is also, I feel like, I feel like I get better at interviews as a candidate throughout the process, but I felt like that applied more to engineering manager interviews than to IC interviews,

because I did feel like the IC interviews were closer to the day-to-day skills that I used. right but yeah that that aspect of like articulating your worldview concisely in a compelling way is not you're not going to like sit down in a one-on-one with with someone every week and say let me tell you about my philosophy of management it just feels like very pompous it's like this there's almost like this behind the scenes framework that you're operating in that you don't even know you're operating in because you've never had to say it out loud yeah yeah yeah that's a great way to think about for me or or you're good at this better than i am and like you start with that and work towards it but for me it's been very like it's been a lot of archaeology

right like looking at what i do and then figuring out oh that's that's right that's why it's like internal self-centered self-focused psychological archaeology you're digging through your own brain trying to understand why you do what you do yes i'll tell you jameson that as a manager of managers this has come into more focus for me because now i'm having to coach people to do their management job and so it is a forcing function to make me say out loud what my philosophy is whereas previously i was just like oh yeah i guess i don't know why i ran stand up that way let me let me write a blog post about this you know and this may be a this might be a good thing for you to do is practice writing a blog post each day where you delve into one of the philosophies

management. And if you're looking for inspiration, there is a great book that I don't think I've mentioned on the show before, but I have mentioned in our Slack community, which is a book by Will Larson. I'll put it on the screen for our YouTube viewers. It's called An Elegant Puzzle, Systems of Engineering Management. Really, really good, crisp book. It's like a user's manual for engineering managers you know it's got sections on all of the all the things i just mentioned like mentorship and performance management and organizational structure and then it's like in the least amount of words describe how to do how this person does that and i've really liked it because it's almost it almost reads like a an appliance repair manual you know it's like if you're in this situation

here are the three things i do bum bum bum like oh nice anyway highly recommended if you're trying to find inspiration to get crisp about your own philosophy i second that recommendation it's a great book will has another book about staff engineer that's a similar oh that's him to kind of yeah distill this kind of fuzzy ill-defined thing into some concrete specifics oh that's great i i knew about that book i just didn't realize it was the same author i gotta get oh yeah yeah that's really the staff engineer is more based on interviews with other folks where an elegant puzzle is more i think his own experience and ideas but there's still yeah same style same same vibe that's really cool really cool all right have we answered it think

so should we should we summarize with our rhetorical bullet points of three that are only actually two oh yeah i was gonna offer this one point of feedback which is when you were saying all the things you should have a philosophy of there were way more than three and oh i just ignored all of them after the third one because because i blasted past the three ceiling yeah i was like one two three what and then my expectations were shattered sorry it's okay they were all good suggestions i'm sure as i listen back to this i'll realize i'll skip the first three and then count by multiples of three. So I'll hear the next three next time I listen to this. Okay, good. Yeah. Do you want to summarize it?

Yeah, I'll summarize. So I think the first thing is it's normal for there to be a higher failure rate for management interviews, I think, as a candidate. So that's first thing is that you are experiencing something that I believe is normal. Sub-bullet on that one is that this particular moment in time, I believe will be even more challenging and even a higher failure rate. and then the second point is get really concrete about what your answers are to these kinds of questions so that when you find the company that wants you that wants your philosophy you've clearly articulated it do some psychological archaeology yes and the third one uh again exercise to the reader or i forgot yeah reader's choice all right that sounds great what should

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