Soft Skills Engineering - Episode 459: Am I cutting edge and how to compliment someone who went from super jerk to super nice

Episode Date: May 5, 2025

In this episode, Dave and Jamison answer these questions: I work for a B2C fintech startup as a senior engineer. Our onboarding funnel has a lot of moving parts due to regulatory compliance and a litany of requirements from various parts of the business. As a startup, we also live and die by optimizing for and demonstrating growth, so we need to gather data from our product and pipe it to various analytics platforms. Finally, we need to offer customer support for high-touch edge cases. All of this is connected together in a very patchwork way between our own code and various secondary and tertiary systems (CRMs, CDPs, data warehouses, etc). I am torn between two ideas. One is that we may very well be doing something “state of the art” in terms of integrating all of this together. The other is that we are engaging in wheel reinvention on a massive and incredibly wasteful scale. I have no way of knowing though, because I am having such a hard time finding holistic accounts from anyone who has done something like this. My gut says that this is something dozens, if not hundreds of companies have had to build at some point, but I don’t know where to find people talking about it. How do I find documented, real-world case studies for how to build a complete package like this? Everything resource I can find online is a myopic, narrow slice of the entire pie focused on only one aspect of the problem. No one is talking about how you integrate e.g. a sane and scalable analytics stack with a fast evolving product. All they want to talk about is how to make a “webscale backend” or “do growth hacking” while assuming someone else is going to draw the rest of the owl. Where do I go to find these people or these resources? Maybe these constitute some form of “trade secrets” - does anyone even want to give this information up freely? If my higher-ups saw me go outside the company for resources, would _they_ think I’m leaking important secret sauce? Sorry that got so long. I love the show! Keep being awesome. I’ve been at my company for about four years, and I’m currently a senior engineer. When I first joined as a mid-level engineer, there was a certain tech lead who wasn’t exactly known for his warm personality. On my very first day, I joined a Zoom call and witnessed him verbally berating someone. This type of behavior was fairly common at the time and earned him quite the reputation as a jerk, though thankfully it became less frequent over the years. Fast forward to today, and he’s genuinely transformed. The intensity has dialed way down; he’s now approachable, supportive, and even recently earned a promotion to engineering manager. It’s honestly been impressive to watch. We have a friendly relationship, and I’d like to acknowledge his growth because I genuinely admire it. But here’s the catch: How do I, as someone junior to him, respectfully bring this up without accidentally implying, “Hey, congrats on no longer scaring everyone at work”?

it takes more than opening the dev tools fast enough to run a javascript snippet to stop a feature flag check that prevents you from using an enterprise feature when you're just on the pro plan to be a great engineer this is soft skills engineering episode 459 i'm your host dave smith i'm your host jameson dance soft skills engineering is a weekly advice podcast for software developers who pride themselves on command shift i and then pasting javascript really fast i feel like you could have a computer do that for you yeah but then you'd have to take the time to write a chrome extension yeah figure out all that package it up make your bundle or learn tamper monkey yeah all all of which i've done and sometimes i just go i'm gonna be fast

i think you really are putting the professional in the pro plan though when did when did pro become worse than enterprise i know right you have you've earned the pro title enterprise is equivalent to contact us yeah get ready to talk many dollar signs lots of sales conversations yep lots of i wonder how much they would pay for this yeah value-based pricing how much money can i get out of you yeah enterprise whomst among us has not tried to sell lots of money of stuff yes should i thank your patrons i was hoping you would thank you too croissant connoisseur i only learned to code so i could look cool in public but now i get excited about cleaning up legacy code please send help noah labhart era dad jokes cron job failed with exit code one oh this is so

offensive we actually can't read it out loud oh yeah i'll leave it to to you to decide if that's what it says or if it is something so offensive we can't read it alexander kuznetsov nick molyneux attribute error none type object has no attribute two string javier gonzalez chewy ted timbrel bob vance vance refrigeration yes become a senior engineer.com is a newsletter you should read doing my part to make dave's heart swell but he should probably get that checked yeah dan from drone deploy chase w norton never is not just a crater on mars flamingo emoji i like chicken i like liver meow mix meow mix please deliver trash panda get status kyle boss can't see dodds that guy over there nevar is not just not just a planet in the vulcan system jenny kim the stochastic

parrot helicon.ai best observability tool for ai red panda is best panda patreon.com.au not hiring me but i got married jonathan king znai beautiful functional user documentation i'm your host steven colbert williamangel.net is now rehiring personal data salespeople because the ai productivity bump was a fad entry level six years experience ragnar brayden canes john grant britney ellick come to the slash new conference in newcastle australia may 28th and 29th if it looks like a duck swims like a duck and quacks like a duck then it's probably a soft skills engineering listener and ouch my 401k yes thank you thank you these are the uh the hall of champions the heroic people that clicked the right buttons and and hooked up the right bank account information to contribute

at the level where you shout them out every single week and you can join them if you go to softskills.audio and click support us on patreon where any amount will get you an invite to our slack team and enough of an amount will get you shout outs of various words that you type yes which make us happy also so thank you ah thank you thank you do you want to read our first question dave yes this comes from an anonymous listener who says i work for a b2c fintech startup as a senior engineer our onboarding funnel has a lot of moving parts due to regulatory compliance and a litany of requirements from various parts of the business as a startup we also live and die by optimizing for and demonstrating growth.

So we need to gather data from our product and pipe it to various analytics platforms. Finally, we need to offer customer support for high-touch edge cases. All of this is connected together in a very patchwork way between our own code and various secondary and tertiary systems of CRM, CDPs, data warehouses, et cetera.

I am torn between two ideas. I got to say, Jameson, just inserting here, this feels like it's going to be a technical question, but I'll keep reading. You got to trust me. Yeah. Okay. So I'm torn between two ideas. One is that we may very well be doing something state-of-the-art in terms of integrating all this together. The other is that we are engaging in wheel reinvention on a massive and incredibly wasteful scale. I have no idea of knowing though,

because I am having such a hard time finding holistic accounts from anyone who has done something like this. My gut says that this is something dozens, if not hundreds of companies have had to build at some point, but I don't know where to find people talking about it. how do i find documented real world case studies for how to build a complete package like this every resource i can find online is a myopic narrow slice of the entire pie focused on only one aspect of the problem no one is talking about how you integrate for example a sane and scalable analytic stack with a fast evolving product all they want to talk about is how to make a quote web scale back end or quote do growth hacking while assuming someone else is going to draw the

rest of the owl i know that reference how to draw an owl isn't that the one yep okay last last paragraph i promise where do i go to find these people or these resources maybe these constitute some form of trade secrets does anybody even want to give this information up freely if my higher ups saw me go outside the company for resources would they think i'm leaking important secret sauce sorry that got so long i love the show keep being awesome we don't know how to stop we will that's a promise we can keep so i picked this question because although it is pretty technical i think it hits at this this vibe of there's this duality i don't know that's the right term but it sounds smart oh yeah it feels like two things are often true that one we have

this unique secret sauce here and two like holy crap someone has had to have figured out a better way to do this yes i have a suggestion which is the the best way to summon a horde of people telling you how dumb and wrong you are and how you're doing nothing novel and how this has all been done before better by other people is to go on like a conference speaking circuit or write a blog post that gets posted to hacker news but how novel and awesome your thing is and then the commenters will come out and say well actually you will harness the collective energy of the internet's well actually which can probably like send humans to space if we're focused correctly i'm only slightly joking though i think if you write down and say hey here's what we're doing

we think it's really awesome it is likely to draw attention that will point you to things that that are prior art or something like that yeah oh speaking of prior art you could patent it and then people try and invalidate your patent and then boom which you'll find out about through lawyers approaching i guess yeah that's pretty slow feedback cycle that's the practicing agile law two and a half years after your patent comes it gets uh accepted then yeah the lawyers show up yeah as you were saying you could write a blog post and then just kind of like attract the attention of all the internet naysayers you suggested so in the blog post describe it and then say it's good i think you you really to get people's attention you might have to say

this is the absolute best way yeah to wire up all your analytics and crm data into one place yeah or not even into just say this is the best way and then people will have something to disagree with yeah don't you think in reality people are going to read it and go yeah oh that sounds like the same garbage sausage making that my company does i i don't know i mean then that that'll tell you something right if you say this is the best way or if you say we have invented a novel way ah yes that can also trigger people to say no uh look at all these other things no one else is doing this yeah but if you get people to tell you you're wrong yeah it'll teach you some stuff i think the most likely outcome though is you do that no one reads the post so yeah you have to get lucky you

to win the the lottery on getting attention i mean for the specific problem domain of like analytics and data it feels like data engineering growth hacking data warehouse there's there's like a cluster of disciplines that all seem like they would touch parts of this but maybe that would get you into the same problem of myopic slices of the pie i assume that there are lots of vendor blog posts where they say the answer to this problem is pay us a bunch of money for our tool yeah i feel like every vendor has one company that goes all in on them and then there's the symbiotic relationship where the vendor talks about that company a lot because they're the kind of the exemplar customer they do everything in the service even stuff it's maybe not good at

or useful for they or they pay the most money to that company yeah and they pay a ton of money and and then so they get talked up a bunch as like this awesome use case and so everybody's looking for one of those but it sounds like you don't have that situation you have the expected setup of a bunch of different stuff, piping things all over the place to a bunch of different systems. I think what's happening here in this organization, so I know that the question is,

how do I go find out information about my, what's the right way to say this? To get other people to share how they do things internally. But I guess I wanted to respond to just the likelihood that I think you're going to find anything interesting. And I think that likelihood is very low because I think what's going on here,

you mentioned CRMs, that's going to be your marketing team. You mentioned CDPs, that's going to be your sales team sorry opposite crm sales team cdp is going to be your marketing team data warehouse is probably your engineering team or like a data engineering team and so like a product team product yeah someone who cares about that i think what's happening here is you are watching conway's law unfold before your eyes where the organizational structure tends to impose itself on your software systems and they will not integrate cleanly unless your org chart has also

integrated and i'm guessing it hasn't and this is actually very very common i see this all the time like we have full-time people at my company who's like 95 of their day job is getting data cleanly from the crm to the cdp to the data warehouse so that it can be visualized on our bi systems for our executive dashboards and for the dashboards we put in front of our teams for their performances performance and stuff and it's just like yeah it's a mess it's just kind of how it is so yeah in this very narrow situation i don't think you're going to find anything interesting out there but maybe they have found a novel elegant solution maybe they have built the interesting thing i i think it is you could put it out there my higher ups saw me go outside the company for resources would

they think i'm leaking important secret sauce right i hope not i mean the fact that it's fintech is maybe a little wrinkle on here because right maybe it could be some more sensitive information but just talking about like analytics and data and how you pipe stuff around that feels pretty generic it's also i mean if you are doing something cool it's good marketing material engineering hiring right you attract people by by talking about the cool stuff you're doing kind of build your your engineering team's brand so that's useful diving into that question of will this be considered trade secrets or will i be revealing something i shouldn't typically in my experience at least the company's intellectual property has very little to do with how you track

like customer data internally like things that would go into a crm or cdp or in this data warehouse listed here that's usually just like hey we bolted this together out of necessity it's the best we could do it's not like this novel thing that we feel like is a competitive advantage typically so i i wouldn't worry about it yeah it's usually and maybe that's a unique thing you have here maybe it's not for you but it is usually the real engineering effort goes into the product right and then up until a certain scale it's it's like the little scraps that fall off the table go into data until it becomes important enough that you put a team on it yeah it's possible that you are doing something horribly wrong like your blog post contains a line that

says and then we copy all the credit card numbers onto the google sheet that we share exactly with our customer service team in case they need to figure out what transaction belongs to what credit card number or whatever. And then that's bad, but assuming you're not doing anything horribly wrong with personal PII or sensitive data, then I really would write it up and put it out there. I think it's also a good time to throw an LLM at this and say like, here's some architecture diagrams. Here's kind of my description of the code flow. Help me write a blog post that describes how this works and then find me other blog posts that have done the same thing you can also do that that's true i mean yeah if it's digested the contents of the internet then it

could have some combination of weights in there that'll that'll spit out some evaluation of your data architecture and then please check my blog post for violation of pci compliance yeah somewhere some auditor just had a brain aneurysm when you mentioned replacing them with an llm yeah You know, we said when we started this podcast, we'd be willing to accept the casualties it would cause when the days finally come. It's that important to the world. Some people may die from this show, but it's a trade-off we're willing to make. I'm willing to make that trade-off for the Patreon names. I honestly don't have a better answer than write about it and talk about the thing that you wrote and share it around to people. Yeah. And if your company's big enough,

they might even have a policy in place that says anytime you write about the company it's got to be reviewed before it goes live and that'll be like your safety net to say like hey i published this but someone reviewed it and they signed off yeah well have we answered the question i think so all right best of luck shall i read our next question yes please this is from a listener named lightly salted meow mix which is a delightful name wait okay is this a cat commenting on how the miyamix tastes good or is this a human who's sampled it either way i'm very interested yeah yeah lightly salted miyamix says i've been at my company for about four years and i'm currently a senior engineer when i first joined as a mid-level engineer there was a certain tech lead who wasn't

exactly known for his warm personality on my very first day i joined a zoom call and witnessed him verbally berating someone this type of behavior was fairly common at the time and earned him quite the reputation as a jerk though thankfully it became less frequent over the years fast forward today to today and he's genuinely transformed the intensity has dialed way down he's now approachable and even recently earned a promotion to engineering manager it has honestly been impressive to watch we have a friendly relationship and i'd like to acknowledge his growth because i genuinely genuinely admire it here is the catch how do i as someone junior to him respectfully bring this up without accidentally implying hey congrats on no longer scaring everyone at work huh what an

interesting question on the one hand i feel like it would be unlikely that someone who was this intense and this much of a jerk at work would have changed without being aware of how much of a jerk they are so hopefully if you say something that implies like hey you used to be so mean and i'm glad you're not mean at work anymore hopefully that's not news and they won't be he won't be shocked and offended and what you're implying i was a jerk hopefully he knows because he did it That would be the moment he reverts back to jerk mode. Yeah, yeah. You're going to trigger a relapse.

But on the other hand, I am continually surprised by everyone, including myself, all of our collective ability to not be very aware of anything. So, I mean, maybe there was personal life stuff going on, right? Maybe he was having some relationship troubles or health challenges, or maybe there's something that was causing him a bunch of stress. And he kind of resolved that thing and it influenced him to become less of a jerk instead of a deliberate effort to say, wow, I'm sure yelling at people a lot at work and I would like to stop.

But let's see, intensely dialed down, approachable, supportive. Hmm, I'm trying to imagine and you're a friend. I feel like you should be able to say something about it. You could just say, hey, I really appreciate how much you have worked on being more approachable and supportive. and i remember some early interactions that were kind of scary and sounds like you were pretty upset at people and i've noticed you really have become more less of a monster i don't want to say approachable and supportive again yeah you used to be horrifying used to be one of the worst people

i knew and now you're not congrats good work yeah now you're the second worst is there a an approach here that doesn't involve acknowledging the bad side of this while simply focusing on who this person has become yeah where you just say hey really appreciate how approachable you are and how respectful you are to others it's great and i like it thank you instead of acknowledging the the relative change meaning the delta between what you were and what you are yeah i think that might feel less impactful because you're part of the excellence here is is how big the change is right but it wouldn't be bad i mean i don't think there's a way you could take it wrong maybe you go into the conversation by saying how much you admire his current state without

acknowledging the past and see if he gives you an opening to acknowledge the change yeah it's true maybe he'll say like yeah man i remember your first day and how i chewed that person out on zoom and then you say yeah boy am i glad i don't do that anymore right like i was such a monster i'm yeah and who knows maybe maybe he'll open his soul to you and say i'm actually recovering from a serious like alcohol abuse situation in my life or i've i was coming out of a bad life circumstance or something you know something that is personal but kind of helps explain it and then that's your opening right and you can say wow fantastic job i just want to say like i'm really impressed with the changes you've made. But maybe I would probably go in, especially in this situation

where I'm kind of a more junior person, I would probably go in not really wanting to acknowledge the change, but just acknowledge the current state and then see what kind of opening or closing he gives you. Every time I think it's probably going to be fine, what's the worst that could happen? I remember how wide the range of human experience is. And certainly there's some combination of circumstances where this friendly kind human just blows up at you if you say the wrong thing so well that's i mean especially this particular human right like that's something this person has done so i don't know i just feel like it's probably fine if you say hey i admire how great you're doing and i really appreciate i see such a huge change in you from when i first joined and

i really appreciate it i'm sure it took a lot of work on your part yeah i feel like the chances of that going poorly if this person is is as supportive and kind as you describe them to be or just sound so low yeah that sounds pretty naive well yeah but also i'm just acknowledging that yeah it is pretty naive i have not seen a lot of ways things can go horribly wrong yeah yeah and my my recommendation for letting the other person give the permission to acknowledge the change is not really based it's not coming from a place of fear like oh he might yell at me that's not at all what i was thinking it was more like just respecting that person's desire to talk about things or not you know yeah that's true i mean if it was a really bad time in his life then

maybe he does want to just focus on the now yeah maybe who knows either way it's pretty personal i mean no one makes a change like that without effort i think that that just doesn't happen automatically yeah some people do get softer as they age like i'm certainly in that boat like i in certain ways you know as i've aged like i'm maybe a little bit more emotional sometimes about cute things you know like things involving kids or relationships you know things like that they kind of yeah tug at my heartstrings a little more than when i was a young whippersnapper but still even having said that this kind of change where you literally yell at people at work and now you're like super approachable and nice that probably took effort yeah which is i don't

I find it inspiring that people do change like this. I am scared sometimes I'm going to get stuck. I'm going to get frozen as just whoever I am right now plus 50 years. But you're already so great. What's the problem? Just lock it in, man. Well, I suppose I could get worse. So maybe frozen is not the worst outcome.

Press that cruise control button on your whole state. I don't want to, though. I see people around me who, I mean, I have a limited view of their internal experience, but to my perception, they appear to have just kind of done that, just kind of locked in at some age and not really changed at all. And that sounds sad to me. I feel like I've got plenty I would like to get better at or improve on. And so good job, your friend slash maybe manager. Well, have we answered this question? i think so just go in there with gusto and tell them how proud you are of all the changes they've

made in their life from all the terrible things they used to do dave this question reminds me of something which is i just really appreciate your personal hygiene so much and you lately have smelled so good every time well i'm glad to hear that i've been working on that how do i tell you that you used to horrify me with uh your awful stench well i i ran out of deodorant for 20 years and now i've got some more i stopped my dog feces deodorant regime the all-natural yeah well congratulations thank you what could people do if they want their own questions answered. Go to softskills.audio and click the ask a question button. And the more passive aggressive you write your question, the better. We just really like that. And we read

every one of them and we love them. So keep them coming. Thank you. Thank you. Thank you. We will catch you next week.