Soft Skills Engineering - Episode 498: Testing in big corporations and how to get my first management job

Episode Date: February 2, 2026

In this episode, Dave and Jamison answer these questions: ‌ Hi Dave and Jamison, Internal dev asker from the second half of Episode 441 checking back in. Your “ask what scared the previous dev” advice in particular has paid off handsomely; I now carry around a little book of eldritch warnings and, somehow, people keep bringing me their unknowable monsters to interpret. It’s almost as though the previous dev knew these sorts of things would happen! I didn’t set out to acquire Lovecraftian knowledge, but here we are, still in one piece. Today’s puzzle: getting busy humans to test our stuff early, while feedback can still make it into production. We’re trying to build a culture where people will poke at a rough prototype now, instead of filing a Very Concerned Ticket three hours before release. How do we get people to test and provide feedback earlier? Do we stay disarmingly warm, promise tiny time boxes, and make a public show of “you said / we changed” until participation feels like the default? Or do we wave our terminal windows around threateningly on a screen share and promise doom (and minor annoyances) until they comply? Thanks for lending sanity to the abyss, —An increasingly arcane internal apps dev I have been listening to your podcast regularly and am inspired by how the podcast and the community have grown. I am a developer with over 10 years of experience and have moved to Sweden from a country outside Europe, with the ambition to build my long-term life and career here. For several years, I have tried to take that step myself, but often encounter the same obstacle: I am told I need experience as an engineering manager — but without the role, I can’t get the experience, and without the experience, I can’t get the role. I have invested a lot of time and energy in developing myself: learning about leadership, coaching, communication, and team dynamics. Despite this, I find it difficult to see a clear path forward. With everything happening in tech right now, I sometimes feel stuck and uncertain how to break this cycle. My question is: how did you take your first step? How can one realistically enter an engineering manager role when the door seems closed without prior experience? Thank you for creating such an honest and inspiring podcast. It already means a lot to me — and to many others, I am sure.

it takes more than realizing that the password reset request email from microsoft is actually a phishing email from rn icrosoft to be a great engineer this is episode 498 of the soft skills engineering podcast where i'm your host jameson dance i'm your host dave smith soft skills engineering is a weekly advice show about all the non-technical things that go into the technical field of software development like kerning importance of kerning yes wow that rn microsoft is very good very clever when you get to be that big of a company do you just buy every domain that could be reasonably like do you think they own rn microsoft.com let me check i don't think they do i just checked the cert oh my goodness let's see how much money it costs to buy it nope it's not

for sale maybe they do own it i don't know but that feels like a way you could you could extort them right you just have to buy up all the sneaky domains i i'm sure you're not the first to think of that probably not i'm probably about 25 years too late exactly you you are generally last to market on the nefarious plot scene yeah i've noticed that about you well i'll accept it that's probably worse things to be like oh yeah totally like first to market yeah i'm i'm first to market at the nefarious schemes then i would be a crypto millionaire dave do you want to thank our patrons yes i do big shout out to everyone who contributes at a level that earns them the absolute privilege of us saying your patreon profile name on the show this time we have a one

time shout out to boots the cat who is dead learn more at boots.rip i i went to boots.rip and i guess i did learn more because there's a picture of boots i think who is i believe dead sorry that's a bummer yeah cool website though okay and shout outs to those that are giving at the level where we say their name every week and they are let me just share my screen okay can you see it does the subservice org do rubens or is it just cold cut joel balanced the parens but forgot the emote icon sad face emote icon go ahead run your own mail server what are you chicken bach bach my actual name on linkedin is yami debugging in the dark canny the mobile development ordinary first of his name it's just you know what i'm

gonna look on linkedin i i don't think this is true i don't see you funny that i just only thought to do that today all right moving on quote or one equals one drop table miyamix jacob channeling bork bork bork eat your little salad piggy and don't forget your hairball donut the missing semicolon christy the world's okayest programmer will angel will spread through these patreon names like a virus new year new you get project ops with fly true.io nick molyneux embedded software engineer sorry embedded software greater than software engineers my entire ide is smaller than your node modules there are lots of things smaller than my node modules yes javier gonzalez chewy

ted timbrel three closing parens with the word followed wrapped in parens by a single opening and then a closing paren wow that was hard to read well done very well done i'm impressed then a literal open brin then Dan from drone deploy never is not just greater on Mars flamingo emoji emoji I like liver I like no I like chicken oh man the

patrons have gotten in my head today your brain is scrambled from all the brins oh I like chicken I like liver meomics meomics please deliver Swiss Python okay I will measure text bandwidth beautiful is better than ugly explicit is better than implicit simple is better Kyle boss can't see Dodds

Jenny Kim the stochastic parrot Ira Chan Jonathan Kings and I, beautiful functional user documentation. You're my favorite customer. Oh, thank you. Will Angel, Jameson, I think you stopped sharing your screen and we can't see it. Deploy drone from Angel Will. Brayden Gaines, Brittany Ellick. Closed parenthesis followed by a single closing parenthesis character.

Oh, absolutely love it. Thank you so much for contributing. If you'd like to contribute, go to softskills.audio. click the support us on patreon button and let the creative juices flow with your patreon profile name if you can't think of anything just put will angel oh should i read our first question dave go for it all right this is from an anonymous listener who says hi dave and jameson i'm the internal dev asker from the second half of episode 441 checking back in your ask what scared the previous dev advice in particular has paid off handsomely

Hey! This was a question about what to do having joined a company as a new internal app dev when the previous one is leaving. The previous dev had been there for a long time and there was a couple months of overlap. And the question is, what should I ask before the senior person leaves?

Yeah. I don't remember what we said, but it was probably pretty good. At least, apparently we said, ask what scared you. And that paid off handsomely. I now carry around a little book of eldritch warnings and somehow people keep bringing me

their unknowable monsters to interpret. it's almost as though the previous dev knew these sorts of things would happen i didn't set out to acquire lovecraftian knowledge but here we are still in one piece today's puzzle getting busy humans to test our stuff early while feedback can still make it into production we're trying to build a culture where people will poke at a rough prototype now instead of filling out a very concerned ticket that is capitalized i hope you could tell from my pronunciation three hours before release how do we get people to test and provide feedback earlier Do we stay disarmingly warm, promise tiny time boxes, and make a public show of, here's what you said, here's what we changed, until participation feels like the default?

Or do we wave our terminal windows around threateningly on a screen share and promise doom and minor annoyances until they comply? Thanks for lending sanity to the abyss and increasingly arcane internal apps dev. Okay, Jameson, I'm going to need your help with a couple of references here. Okay. This person says, I carry around a little book of eldritch warnings. What's an eldritch warning? eldritch is like the lovecraft word are you familiar with lovecraft oh that was going to be my second question what is lovecraftian okay uh sci-fi author from the early 1900s

who created a genre of sci-fi horror that is now named after him it's also called cosmic horror it's kind of the the unknowable cold uncaring universe and humanity's tiny place in it and there's these horrifying godlike beings that are entering our reality and you briefly see them and go insane and there's a lot of like your your mind can't comprehend unknowable geometries and okay yeah so eldritch horror is probably a phrase he used a lot but a phrase that if anyone says that word it means they're referring to that type of thing okay yeah cthulhu have you heard of like call of cthulhu or the mountains of madness or oh cthulhu that's Yeah, he invented Cthulhu.

Okay. I thought Cthulhu was a real thing. He also said a lot of very naughty words. So he's a little heavy on the profanity. Not quite profanity. He's got some, well, how do I say this on the podcast? I don't think I do. I think that's the answer.

Anyways, that's what it's about. Okay, good. All right. So we have an Eldritch, a book of Eldritch warnings. So, yeah, it's like this cursed knowledge that drives you insane if you know it, while also promising you great power, that kind of thing. Okay. Oh, good, good, good, yeah. Yep.

Which kind of fits. Anyways. Yeah. Okay. Does that answer your question? It absolutely does. Now I forgot the question. And that answers the listener's question.

The end. Okay, so how do we get people to test and provide feedback earlier? and I guess we have a problem here where people aren't really looking at their stuff until the last minute and then reporting problems at the very last moment when it's too late to fix. Yeah.

I'm curious to know, are the very concerned tickets bugs they have found or is it big requirement shifting, whoa, whoa, whoa, this needs to do this totally different function instead of the thing it actually does right now? Because bugs just means you haven't practiced no bugs-driven development correctly

and there's always room to improve at that. But there are other options besides test it, although other people testing is very useful. I mean, just UX feedback and, I don't know, testing with users is great. It turns out it helps a lot, but that very concerned ticket capitalization makes me feel like maybe it's like someone's manager

who figures out, wait a minute, they're launching this thing that obviates my whole team? Whoa, whoa, whoa. Ah, well, that would be a whole other dynamic. Changes my process. We can't have that. Yeah, cheese moving. So I guess I'm asking,

are you trying to make the software better by finding things that are confusing or annoying or broken are you trying to communicate more widely to the organization hey this thing is going to exist and here's what it will do and avoid surprising people when the thing suddenly exists or a secret third thing yeah or a secret lovecraftian thing yeah hmm you know i've i've had very interesting results, both from myself on the other end of this. And I guess I've been on both sides of this actually. And I've been surprised at human behavior being uninterested or unwilling to participate in the process early. And then once it's too late, being super eager to participate in the process. I'm not going to look at your prototype. I'm not going to look at your mock-ups.

i'm not gonna check my email or read the slack message for months yeah but once you ship this i am going to go into an absolute fit of rage about all the things you messed up yeah you know i definitely have seen that on the other hand i've also seen people who get involved too early and they're like oh i want to see like i want to see the very first iteration that the developer works on and i'll start giving feedback and they give feedback on a bunch of like obvious bugs it's like well yeah that part's not done yet like you shouldn't have even looked at that part you know And they're like, oh, yeah, but it's not working. This button doesn't do anything when I click it. I'm like, yeah, we haven't built that yet. It's just like a wireframe or it's like a stub or something. And so it's like you have people on both sides of this divide and not very many people in the middle, I've noticed. Hmm. I've also, depending on how intense the politics are at your place, I kind of hinted at this, I guess. But there could be a downside of attracting more attention, which is more time for people to meddle, time for your project to become part of someone's plans instead of just a thing that you're working on, which may or may not be helpful for you.

I do think your instinct to get people to test our stuff early will lead to better software. And so it is noble and is certainly worth doing. But what do you do? There's one factor here that I think changes everything about the strategy I would employ if I was in that situation. And that's that these are internal applications for your team members to use. you're not deploying this out to a 10 million user audience whose businesses depend on it and who are going to cancel contracts if you you know move a button or something and they have to retrain all their all their medical staff or something like that that's not your situation

here now i'm not saying it's a small number of people but it it is much easier to pivot in on internal piece of software and change process internally for your own company than it is to affect a customer who bought something and expects it to do what they paid for and so i would say give up on this whole idea of like here's a prototype you know here's something we put together in figma just give up and instead start shipping stuff in a much earlier state and put it behind feature flags or whatever you got to do to gate access to it so that only certain people can have access and just say look it's ready for you to look at now and don't even tell them like this is not done just constantly iterate on this thing so i got the impression

from this question like oh three hours before we're gonna go to production i got a ticket from a very concerned person and i'm like so what like you can go to production all the time is this like a one this is like a once a year opportunity and maybe it is i don't know i think it's kind of assuming it's a it's a web app where or some environment that you can update i am as easily infrequently maybe it's embedded software maybe it's deployed on some gnarly mainframes and you have to brave yeah you have to crawl through some extensive duct work to with a floppy disk in your teeth to insert it that was great mission impossible vibes you just yeah there i have a dumb idea here's my dumb idea find someone who is going to be using your software put a half an

hour meeting on their calendar say yeah i'm going to show you this tell me what you think yeah this is the dumbest possible version of user testing and user testing yeah very deep discipline with much literature you can read about it and many strong opinions you can have about the exact way to do it but if part of your time is people are busy this sounds like a larger company calendars often have great sway in how people's time is used and if this feedback is important enough for you and you're also trying to save yourself some future pain, it probably is worth you also spending the time to be there and watch them do it.

And that's a good way to make sure it happens instead of saying, please test this and tell me what you think. Then it's async and then it's on the to-do list. Yeah, I like that a lot. And user testing is so much less expensive and burdensome for internal software because they're just your team members, right? You can just go, like Jameson said,

just put a meeting on their calendar. It's awesome. Yeah. if they don't show up put another one on yeah yeah you get the meeting yeah i think that's all my advice do that have we answered the question i think so i mean i'm sure there's a hundred reasons why this might devolve into a more complicated scenario but the reality is i think if you can pivot like not pivot if you can evolve your process into a more incremental process where you are releasing a little bit more frequently so that you can put something out there

and yeah it's not going to be perfect but then you can get feedback because people are actually going to start using it yeah and then just release a new version as soon after that as possible i think you're going to be great and then forcing the feedback is i think a really good thing yeah when i worked at a big company i found that one of the most effective ways to get people's attention was to put a meeting on their calendar and people would do it to me too it worked it was a good mechanism yeah it was a bit of a corporate dark art and can be abused like yeah all the dark arts yeah like all the lovecraftian geometry yeah i i think another way to think about this is what are their incentives here and they probably have a long to-do list and you saying hey will

you please test this is sort of like you asking for a favor like the immediate benefit to them is not super clear the amount of context it will take to understand what the thing they're even trying to test might be large depending on how close they are to the the development of this application um it's it's expensive the payoff is not clearly very high i'm not saying it's not very high but it's not obviously high payoff so it's easy to just push down the stack that's why i think the meeting thing is useful i think yeah just say okay you shipped like like dave said great you have your very concerned ticket three hours before release great we'll address that in our next release tomorrow or next week whatever and as you show that the feedback is worth it to

them then i think it will be easier for people to participate in the future and you might not have to work so hard to gather it because they will have seen it work but i think it will be more work up front because they're they're i don't know they're being risk averse it makes sense yeah well all right we've answered our next one yeah please do yeah from an anonymous listener who says i have been listening to your podcast regularly and i'm inspired by how the podcast and the community have grown well thank you very much we appreciate that i am a developer with over 10 years of experience and have moved to sweden from a country outside europe with the ambition to build my long-term life and career here for several years i've tried to take that step myself

but often encounter the same obstacle i am told i need experience as an engineering manager but without that role i can't get the experience and without the experience i can't get the role i have invested a lot of time and energy in developing myself learning about leadership coaching communication and team dynamics despite this i find it difficult to see a clear path forward with everything happening in tech right now i sometimes feel stuck and uncertain how to break this cycle my question is how did you take your first step how can one realistically enter an engineering manager role when the door seems closed without prior experience thank you for creating such an honest and inspiring podcast it already means a lot to me and to many others i am

sure this is a good question we often talk about this in terms of getting your first job as a software engineer where everyone wants to hire more experienced engineers but you can't get the experience without a job, and so it feels like a chicken and an egg thing. This is a more focused version of the same dilemma, I think. Yeah, it is. And also, a lot of people don't want engineering manager jobs, so it's a little bit of a different kind of scenario. You're saying engineers that they just want to write code, they don't want to do all the other stuff? Yeah. As I think about, as I kind of observe other industries, like let's take sales, for example, it seems like in sales, a lot of people are aspiring to be the sales leader

the manager maybe the same is true in other fields too but in software engineering i don't see that very much i'd say less than 10 of software engineers aspire to engineering management well those numbers might work out because i don't know i feel like one manager for five to ten engineers is a reasonable number at 10 even it's getting a little bit high yeah like this okay i'm told i can't i i yeah i need more experience to do it it's true that you do need the right combination of opportunity that fits someone who has not done this before and demonstrated aptitude to give some confidence that and you probably will be able to do this so there are many engineering manager jobs that you would not be a great fit for or or not visibly be a great fit for larger

teams or managers of other managers or or mission critical projects or something like that but that's not all of the jobs yeah i have a potentially concerning thought that i'll get out of the way and then we can get to all the positive stuff but one thing that could be happening here is this could be someone's way of telling you i think you will not be good at this because everyone who has been an engineering manager had to do it for the first time and someone asked to look at them and say i think you'll be good at this and if if people keep saying, well, you need experience to do it. Sorry, you're not a good fit for this role. Maybe another one, not this one though. And if it's the same kind of company and the same people

saying that, that might be an indication you do not seem to, according to whoever's making these decisions, you don't seem cut out for it. And it may or may not be true, may or may not be true at this specific company, but maybe not true at other places. So if it is really this persistent vibe that is following you around at this job and you've been here a while, it is possible you could do that somewhere else you're risking things and starting over a bit moving to another company as well but that i just want to plant that horrible seed in the back of your mind yeah thanks a lot james you're welcome but it's probably not it's probably probably not uh yeah oh yeah i mean it's probably not actually that that would be depending on how close of a

relationship you have with a a manager you could ask them hey i keep getting told this do you think I would be able to do it. And if you trust that they would tell you if they didn't think that. So hard to, exactly. It's so easy to get a false positive. Or even, okay, maybe less of a binary yes or no question. What do you think I would struggle in in that role? What do you think would make me not a great fit? That's kind of more things to work on. Yeah. Still hard to get an honest answer out of that one, I think. Yeah. Maybe that's just my cheery, non-confrontational American West culture.

This person is in Sweden, and my stereotypical impression of Nordic peoples in general is that I think they are more blunt. Okay. So maybe it'd be easier to get a clearer answer. Yeah. Maybe not, though. I don't know. Way to paint an entire complex ecosystem of cultures and history with one blunt paintbrush. Everybody knows that three hours of daylight a day makes you blunt.

Explanation's clear. I think it's pretty straightforward. you don't have time to mess around you have three hours outside i have three hours i don't have time for your stupid questions yeah i'm gonna give you a straight up answer i'm not gonna dance around this thing yeah okay you see the sun's already setting oh boy yeah i mean i i think a lot of people get into engineering management even though they aren't necessarily trying to do so like this was kind of my story but I found myself really not wanting to be in any kind of technical or even people people are technical

leadership at all for the first I don't know 10 years of my professional life but there was definitely a weird gravity well pulling me towards it often and I've probably told the story on the show before but i think i quit my first couple of jobs because of that gravity well i just kept getting tugged into this more formalized leadership where i was doing less and less code writing and more and more like project managing customer relationship managing and you know people kind of like recruiting like you know all the things that managers tend to do and i'm like i need to reset i gotta get back to writing code i think i've done that three times and eventually i just gave in and allowed the gravity well to consume me but it you know timing for me the timing needed

to be right where i felt like i was ready to do that and that's what i'm doing now so i kind of have the opposite problem i didn't want it and it wanted me of course back then the timing was i'd say a little bit more favorable to career growth because right now yeah boy i think things just seem really calcified right now yeah when the industry is expanding rapidly there's more roles for leadership yeah absolutely more need more demand yeah less supply because i said leadership i mean management but you're basically saying that the only reason i got tapped for leadership is their desperation i can't disagree with it oh i guess i am kind of saying that i don't think i meant it that way but i mean there there is a somewhat standard path into engineering

management which goes be a good engineer be someone who is visibly known to be competent and capable be good at communicating with other people both on the engineering team and someone outside the engineering team as well so have have good technical chops ship stuff talk to people And then there's a kind of project or tech lead role, vague intermediate state where you're not just shipping code for yourself, you're not just pulling tickets off a queue, you're in some way involved in defining the work and helping it be delivered by more than just yourself. You're not doing management. You're not doing performance reviews or one-on-ones or maybe a lot of cross-team coordination or that kind of stuff. But there is some amount of higher level organization of longer delivery timelines, more people involved. And doing well at that is a way to demonstrate. And maybe I'd be good at the other stuff involved in that as well. and if you do that stuff and then there's a need where you are there'll often be a new team forming or a manager that leaves or some some gaps somehow and then you can say well look i've done this other stuff that isn't quite the same job but can build confidence that i could do this job

so they don't say a lot about their specific technical roles i see learning about leadership coaching communication team dynamics i think that is useful for being a good manager and probably less useful for demonstrating you would be a good manager because unfortunately it really is like do good work on projects that involve multiple people that's and those skills can help but there's a risk that you get sucked down the aisle of corporate business self-help books read a bunch of airport literature and feel like well this is what i need to do to become a good manager versus like i need to show i can deliver stuff with other people yeah i agree and i think that that that's a good segue to my advice which is if you want to be an engineering manager or

and frankly this applies to any role if you want the job start doing the job now that doesn't mean you can do a hundred percent of the job on day one but you can start doing the things that are part of that job. And eventually, it'll become a very natural transition at some point where someone is like, oh, we lost a manager over here. So-and-so has already been doing half of the management stuff. Let's get them plugged in and go into town. So what does this look like on an engineering team? This looks like volunteering to be your scrum master. This looks like writing technical design docs. This looks like managing ticket statuses and helping do some of the administrative stuff. All the things that your manager, you see doing that you could help them

do without having the full people management authority, offer to do those things. And if it's not clear to you what those things are, ask your manager, what are some things that I could help take off your plate, knowing that, you know, I'm interested in doing kind of management stuff in a non-threatening way, like, hey, I'm not coming for your job, right? But, you know, ask, what are some of the things that I could take off your plate and help you reduce your workload a little bit. I'm willing to do it. I'm willing to put in some extra time to do it. And then see what your manager might actually be happy to unload some things on you. By which I mean mentor and guide, not unload. And you'll win. You'll benefit from that because you'll start doing some of the

things you like. And this has two benefits. One is that, what I said before, you'll actually get experience doing management stuff. And when an opportunity opens up, you will probably be on the short list of people considered for it but the other benefit is you might learn that you hate this yep and this would be a good way to find out before you accept a job with a management title where you're kind of stuck and saying i hate this and i want to get out of it is you know your hands are a little bit more tied i have seen how many have i seen five six maybe six engineers who were not managers and were the kind of engineer I'm talking about, where they're good communicators, they deliver well, they work on stuff across teams, move into engineering management, and

then move back out. Yeah. I mean, I've done that. Yeah. And it's not that they weren't horrible at it. It wasn't that they were just crashing and burning. It's that they discovered that is not what they wanted to do with their lives. so that is a useful thing to know or even just know and not at this company or not right now or

yeah because it is you do miss some stuff yeah but it's hard to know until you try it yep and if you think you want to do it you think you would like it i think that's valuable information if you just think i would like to make more money and be more valued and grow my career it is still possible that you'll find joy in this or the fact that you are making more money and advancing your career will will help but it's possible that the actual work you do will not make you happy and yeah it's not the best good to know though it is well have we answered this question i believe we have what can people do actually there is a question we didn't we didn't answer what's that how did you take your first step oh what do you know it was the way i described you should do it

i was just a developer building stuff i feel like i was a relatively good communicator and helped plan and coordinate stuff and i was kind of leading a project or two and then there was an opening we had kind of a reorg and shuffled some people around and i actually said no the first time i was asked to be a manager because i was so you didn't pursue it i think i wanted to by the time it happened but you said no um i don't remember if i wanted to at that point i do remember wanting to have more influence and decide more about what happened. And it felt like, oh, this would be a way I can do that, which is sort of true and sort of not. But the second time around that there was a need, I felt like I was more ready and I wasn't that ready, but probably

more ready than I was before. So it wasn't, I should go talk to some people from around this time. Now I'm trying to think, I'm probably just rewriting my memories in real time, trying to recall this i feel like i told my boss hey if this opportunity comes up again i'm interested like sometime after the first time that they asked me so i think i i had kind of also put into their brain hey but jameson's a person who could do this and the company i did this at managers were not cool like the engineers did not want to do management so that also helped a little bit yeah interesting okay yep so you're just so great the opportunity just came to you you manifested it i think it probably took years and luck and some amount of skill on my part

and the right circumstances and trying and there was a gap between when i decided i actually i would like to do this and when it happened i think it was i don't know a year or so but it wasn't immediate so it goes all right very cool yep that's a very incoherent retelling of this story i should make a i should figure out a more polished narrative that may or may not be true yeah so that it sounds better needs to look more like the hero's journey yeah exactly and then a wizard approached me yeah all right now clearly we've answered the question yeah i think so i think we got it and what can people do if they want their own questions answered go to soft skills.audio and click the ask a question button where you can fill out our little form we thank

each and every one of you who takes the time to fill out that form each week. We very much appreciate it. We love reading your stories and your questions. Please keep them coming. Thank you. Thank you. We'll catch you next week.