Soft Skills Engineering - Episode 508: My company is an unethical spammer and my coworkers take so much sick time

Episode Date: April 13, 2026

In this episode, Dave and Jamison answer these questions: How can I get our company to follow the law and stop sending SPAM without being regarded as negative? We’re sending out emails that don’t comply with CAN-SPAM, and I think we should comply due to the risks, but I don’t want to risk any blowback! People want the emails to look more ‘human’ sent, and putting your mailing address at the end of an email is not very human, so we’re not doing that… It’s a medium startup (500 people), but I’m close enough to the marketing work that they might know it was me! Should I send an email to our general consul? How can I raise concerns and do the right thing without being regarded as not a team player?? How do I stay motivated on a team that’s always sick? I’m on a team of 3 ICs and one manager. The other two ICs are plagued by health issues. I am trying to be empathetic, but this has been going on for the at least a year. One of them regularly takes sick days, often turning into sick weeks. The other has a long term issue and regularly does half days. This affects our ability to produce results, but we don’t have a PM and don’t really have deadlines given the nature of our work, so it’s not really noticed. I feel like we are moving a lot slower than we could be, and when we do check-ins on our goals at the end of each quarter, we maybe only hit like 50% of our goals. To me it’s quite obvious why we don’t hit our goals, but everyone else seems to be surprised by it. My manager can’t manage with enough rigor to produce results. I’ve brought this up to them before (our goal misses, not teammates being sick), but nothing seems to change. As the only seemingly-healthy member of the team, there’s no incentive to work more than the bare minimum. I feel like I should be taking more sick days! This is very demotivating and I feel like I’m stagnating. How would you all approach this situation? Should I also suddenly have health issues? Is this actually a blessing in disguise and I should make the most of it? Show Notes https://overcast.fm/+ABLmzfhZxak

it takes more than claiming i've done incredible work but the risks of releasing it are too great to be a great software engineer this is episode 508 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 sandbagging i don't know well i just want everyone to know that this episode is so powerful that we've actually sat on it for three months and we shared it with all the most influential people in the world first and now it will be released ethically now that everyone's had a chance to prepare we did give out a hundred million dollars of listening credits and so

that's right people have done incredible things with that very real money that's right definitely exists and is worth that much yeah it's worth a lot and the credits we don't really keep track of them so i don't know it's a kind of an honor system thing it's a it's like those tip boxes at restaurants uh-huh my startup operates on the give a penny leave a penny take a penny model for payments we partnered with 7-eleven yeah i guess that is basically the open source funding model though it's basically give a penny take a penny yeah leave a penny take a penny keep open ssl running so the internet stays alive dave do you want to thank our patreons patrons i do i want to thank the patreon platform but also i want to thank those who are contributing on the patreon

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Thank you. I agree. All right, Dave, should I read our first question? Let's do it. This is from a person named Ethical Team Player. How can I get our company to follow the law and stop sending spam without being regarded as negative? We're sending out emails that don't comply with can spam. And I think we should comply due to the risks, but I don't want to risk any blowback.

People want the emails to look more human sent and putting your mailing address at the end of an email is not very human. So we're not doing that. it's a medium startup of 500 people but i'm close enough to the marketing work that they might know it was me should i send an email to our general console how can i raise concerns and do the right thing without being regarded as not a team player all right well man can spam i looked this up the can spam act is very old it is 23 years old now that's just not a word i've heard in a long time some of our listeners are probably younger than that oh boy yeah okay there are a couple weapons you can use in this fight but you are fighting against powerful incentives which are

number go up yeah and marketing's job is number go up and basically anything you can do almost everything you can do here is going to make number go down and they will not be pumped about that I worked somewhere where we sent two-factor auth codes, and they were four digits long. And every year we got a security review, and it dinged us saying, hey, these should probably be six digits because four digits are pretty easy to brute force. And every year we had the same debate, which was like, yes, but number go down because six is more than four, and some amount of people will drop out. And so number go down one, and we did not update it. Oh, yeah. Marketing is great and is useful, but it is a double edged sword. And one of the benefits and downsides is I guess this is the double edged sword part. It is so much more measurable now. And that means it's very easy to push back against stuff saying, wait, this will impact our metrics and or show that it does impact our metrics. Yeah. For this specifically, I think you have a counter number, which is, hey, email deliverability is impacted by people saying our stuff is spammy.

And often this is enforced at like this email provider level where, I don't know, whatever underlying vendor you're using will ding you or you can potentially even get cut off if enough people report your stuff is spammy. True. And the fact that that hasn't happened yet means maybe it's not actually that spammy. Yeah. I'm ignoring all the actual law here because I don't know what it is. In space, there's no such thing as spam. All email is allowed. That's right. And it's all good. Yeah. Space law is silent on this point. Because it's just not a problem we've encountered yet. Yeah. I mean, certainly I've seen just an avalanche of clearly LLM generated emails

from air quotes people. And maybe those are falling afoul of some legal stuff. In fact, something I've been meaning to tell our audience about that is we probably get five to ten maybe maybe 15 or 20 of these every week about the podcast yeah and they are hilarious because they've gotten good enough to now they know they need to be personalized and so we will get an email that says things like hey just listen to your most recent episode really loved the comments you made xyz and they'll actually have actual comments we made and then they'll say that relates to a guest that i think you would love to have on your show who covers marital intimacy like yeah this was actually a topic and i just laughed so hard

because i'm like i guess i i mean great job personalizing sort of yeah a robot downloaded a transcript of our show at least we're pretty sure yep and then pitched their marital intimacy guest which is like right down the center of the fairway for our podcast topics yeah i mean it's a i guess it's a non-technical skill so hopefully you don't need that at work i stand corrected the universe of addressable topics is bigger than i realized i guess yeah should i send an email so yeah it depends on if you're trying to i mean legal and to some extent security and compliance exists to hedge against risk they're not often profit centers they're often things to avoid potential catastrophic risk

and so there's a bit of a like the sky's falling or boy who cried wolf issue with legal and compliance where generally every single individual thing they say is unlikely to happen but if you just never do any of it then at some point some risk will bite you and so you're hoping you being the business you're hoping that by having these departments they will prevent some actual things that would have happened and the cost won't be too great so it is a powerful cudgel to use but that's a different approach than saying like hey our business will actually be better off because of maybe deliverability or trustworthiness or something so like this is kind of the whistleblower route versus the i will try to convince you route and if you go the try to convince you route

and then you go the whistleblower route and you're worried about being found out, like, yep, you will be like, if you mount a campaign to say, I really think we should improve our emails and make them less spammy and talk to marketing about it and go back and forth

and they just say, no, thank you. And then two weeks later, legal comes down and says, we have to do this because of the risk of financial damages from us being sued or whatever. They'll definitely know it was you. Mm-hmm, totally.

but you know one thing they won't know it to you what if you fight spam with spam oh what if instead of instead of reporting your company or reporting you know telling the people in your company you don't agree what if everyone at your company starts receiving incessant amounts of spam which don't have the unsubscribe option which don't have any of the can spam requirements and then just see how they feel you're sort of trying to incept them with this idea of like we want you to organically come to the conclusion that spam is bad in general and the world would be better off if everyone including us sent less spam yeah or at least complied with the canned spam rules yeah um okay i mean maybe it'd be even better if you sent some that did comply

also so they saw how much how much how much better and nicer it made them feel that's a great idea even more spam you could even call it out be like look you're getting a lot of spam right now but i just want you to know this is a good one this is the artisanal like i don't know oak barrel aged smoked spam yeah exactly oh man where did spam come from i mean is it literally from the meat i don't understand that connection oh oh i know this this is this is a throwback and maybe it dates me but i know why it's called that why is it this is a monty python reference okay and there's an episode of monty python where all the characters just yell spam over and over and over and they drown out everyone else okay and so unsolicited bulk email that makes all your

other emails hard to find because of how quote loud it is became known as spam because of that sketch was that a reference to the canned meat product yes okay yeah that was cool thank you now i know yeah it's a good one a little bit of internet internet history internet lore as the youngsters say now back in the day and in fact just this last weekend i went and saw the musical spam a lot oh which was your spam aficionado i'm pretty much super into spam spam enthusiast how topical i know perfect it's so funny oh you do a lot of prep for this podcast yeah i was really committed to this question i booked yeah got tickets i even rolled my ankle going down the stairs to my seat so i was really just

and i i played injured even though i had an injury i stayed in the show just so that i could give you this story yeah maybe i'm just naive about the ways of marketing but i feel like i can tell when i get a marketing email and i wouldn't look at an email and say oh it doesn't have the address at the bottom yeah i will respond now yeah that's the thing if that's the main gotta be i mean it's just gotta be a funnel thing where there's just enough people who will that it's still worth it it just seems i don't know it depends i guess it depends on the business bizarre if it's if it's like consumer facing and you're right it comes down to like a few percentage points or something maybe that's what's going on but i also don't this doesn't seem like it's a major big deal to me

and so it like i guess let me i would ask the listener to be introspective about what is motivating your concern is it that you are concerned about the actual nature of the email being harmful in some way? Like, this is bad. We are doing a bad thing. Or is it that you are a really strict rule follower and you know about the canned spam legislation and you want to comply with it just because it's a rule?

You know, these are kind of two different scenarios. If you just want your company to conform to the rules, like because you're such a deep rule follower, then let the rule system punish your company. You don't need to do this. It's not your job. And if, indeed, they are an egregious violator of this rule, they will be punished. Now, I haven't really followed the CAN-SPAM compliance regulatory actions that have taken place to companies.

But surely there's somebody who is in charge of regulating that, and they will come after your company if your company is found to be breaking that law. So just let that system play it out. And if they don't, like if they don't enforce that law, then your rule follower heart can rest at ease, knowing that your company has apparently not violated the law in such an egregious way that they are going to be prosecuted for it. But let's go back and evaluate like setting aside the rule follower aspect of your heart. If it is indeed something else, like you actually think these emails are harmful or bad in some way, then I think there are ways to raise this concern with the people in charge that don't make you look like a negative Nelly or like a negative, you know, what's the right way to say this? Like someone who's a detractor in the business. yeah and that just comes down to a matter of messaging i just googled penalties and many different numbers all appeared 53 000 per email is the maximum 43 51 i don't know where these are coming from my my two seconds of legal knowledge on this as of a fresh google says that the ftc enforces it so i guess you can report them to the ftc if you really want to like that's that's that's

your ultimate lever here if you want to cost your company millions of dollars because of this yeah but it's probably not what you want right like you probably don't want a regulator to come and smack yeah it sounds like they're worried about someone else doing that yeah if you do want that you could ask a friend to do it on your behalf is this like the irs where there are bounties the irs has bounties i think so you're saying i can turn my neighbors in for tax evasion and make money i thought there was something about that i don't know because i've been wondering what i'm going to do in a post ai software engineering career and this sounds pretty good yeah yeah i could pay for a lot find out who among my peers family and friends are committing tax fraud and

report them that's my new income just start up some casual conversations and then be very careful about paying taxes on the bounties like just make sure you pay those right well should we talk about how like how a narrative situation could work here like how to actually communicate this yes i think a little research is warranted here. First of all, a little introspection to decide like what is motivating me here. And if truly you think that your company is creating a bad experience for the recipients of this email, then find a way to articulate that bad experience. And then go to your company and say, hey, you know, I know our company really values delivering a high quality experience to our users. And I want to contribute to that. In that spirit, I've found a few things

that I think we can do in our email campaigns that will make a better experience for our users. They're low cost. I've done the analysis on conversion risk, you know, or like whatever the, you know, whatever the KPI is that these emails are trying to hit. I've done a little research on that. I think the trade-off will be worth it. But here are the three things I think we should do to each of our emails to create a better user experience for our email recipients and just propose them and see here you didn't just show up and say we aren't complying with can spam and we need to comply what you're saying is i've identified a part of our values that we can do a better job living up to here's how we can do it i'm sold my spamming days are over yeah there's also a if you

accuse people of being spammers you will trigger some defensiveness probably exactly for sure true if you're saying hey you're you're shady like the average person is going to say i'm not shady and thus i will stop paying attention to the words you're saying yes instead you give them a way to listen without it being a a i don't know implied attack upon their character it's a lot easier Totally. That is so true that it probably is worth saying a second time. When you come out of the gates accusing someone of being bad, their defense mechanisms will kick in. It's subconscious. They can't help themselves unless they have extreme self-attentive mindfulness, which is rare. they will respond negatively to that they will defend themselves your brain is hardwired to defend itself against that kind of thing and yeah what's really going on here is that even if they are doing shady stuff i promise you they have told themselves a story that what they're doing

is necessary and good most almost everyone has an internal narrative that convinces themselves that what they are doing is the right thing and sometimes it's because like well everyone else is doing it sometimes it's like well i'm just getting what i'm due because of all the years that i was on the receiving end of bad stuff so i just i'm just making up for that whatever it is but they have some story and if you can figure out what that story is like how do they justify this then you can talk a little bit about like here's a better story and replace that narrative with something that that still speaks to their goodness and helps them affirm that they are good while getting the changes done that you want to get done and and on that note i i wish i i'm going

to have to look this up and put it in the show notes. There was a magnificent podcast that came out this week where some random somewhat junior software engineer who I'd never heard of interviewed a now retired VP from Amazon who did 15 plus years as an Amazon VP. And oh my gosh, this guy, like you could probably take all 508 episodes of soft skills engineering and replace them with this one like three hour interview where this VP talks about exactly stuff like this. Like here's how I navigated the world as a VP at Amazon. It was mind-blowingly good. So many truth bombs and so many like super candid stories about like, here's how I fire people. Here's how I negotiate to get the good people on my team. Here's how I get other VPs to give me

what I want. It was crazy. I really enjoyed it. I actually learned a ton from it. And I was like, oh my gosh this is a world we live in and a lot of us don't know it anyway i'll link that in the show notes but his ideas this vp's ideas about how to craft a narrative he calls it polite fiction it's the name he gave it which means like how do i tell a story to you that is close enough to the truth to get the job done but and and polite enough that you will accept it it was wild i still haven't listened to it i know you you mentioned it to me earlier and it's on the list now oh cool did i did i message it to you yes okay i've got i'll go find some dishes i've been saving just for a waiting for a good podcast a lot of dishes for this one's a few hours worth

yeah good news i am filthy finally you're filthiness i've got plenty of dishes all right have we answered the question i think so good luck good luck dave will you read the next one. Yes. Okay. This question comes from an anonymous listener who says, how do I stay motivated on a team that is always sick? I'm on a team of three ICs and one manager. The other two ICs, oh, by the way, IC stands for individual contributor. The other two ICs are plagued by health issues. I am trying to be empathetic, but this has been going on for at least a year. One of them regularly takes sick days, often turning into sick weeks. The other has a long-term issue

and regularly does half days. This affects our ability to produce results, but we don't have a PM and don't really have deadlines given the nature of our work, so it's not really noticed. I feel like we are moving a lot slower than we could be, and when we do check-ins on our goals at the end of each quarter, we maybe only hit like 50% of our goals. To me, it's quite obvious why we don't hit our goals, but everyone else seems to be surprised by it. My manager can't manage with enough rigor to produce results. I've brought this up to them before, our goal misses, not teammates being sick but nothing seems to change as the only seemingly healthy member of the team there's no incentive to work more than the bare minimum i feel like i should be taking much more sick days

this is very demotivating and i feel like i'm stagnating how would you all approach this situation should i also suddenly have health issues is this actually a blessing in disguise and should i make the most of it this is a fascinating question i feel like dealing with this as a manager is one of the hardest problems i don't know i guess there's infinity hard problems but this is one of them if someone is underperforming and is just i don't know they're just not showing up or they're mean and make your team worse or they just don't have the skills firing people is hard but it's not as hard as like someone has cancer yes and thus is unable to work as much as someone else that doesn't have cancer having cancer i don't know what do you do

like it's it's just right smack dab in the middle i don't know what the health issue is here but it sounds somewhat chronic and for somebody at least and known to people i don't know i don't know what the easy solution is like you could put on your shrewd cold scrooge businessman hat and say well it's not illegal to fire somebody for having cancer and they sure aren't working enough so see ya so bye bye find somewhere else with health insurance yeah oh man do you sense in this question that there's some amount of skepticism that these people are actually sick a little bit yeah i wonder if some of these are like mental health days and then some people maybe are maybe you feel like they're exaggerating it or or this sort of like gosh you people can't do anything type of eye

rolling going on i don't know the details are not clear but i mean even then that's still tricky to deal with as a manager some of that is legally protected there are like workplace accommodations people can demand and some of that may involve different working hours or expectations so i don't know yeah this one is very tricky and i also sense this might be remote a remote situation yeah where you can't like see the people in person and that has two effects one is that it's harder to confirm that they're sick you know because sometimes you can pick up a vibe from someone like oh yeah this person has clearly been struggling with an illness yeah because you see them in person and detect it the other downside is that it's hard to really connect

with them and empathize like what exactly is going on and i don't know so i think that's a complicating factor and it does seem like that's what's going on here at least reading between the lines yeah i'm gonna be honest i have to pull out the old reliable on this one i think the easiest thing you can do here is work on a different team if you want to work on a really high performing team that really pushes to hit goals and gets a ton of stuff done i do not think there's a way you can give feedback to your manager and your co-workers to smush this team into that shape i mean you could kill them i guess accelerate their illness oh my gosh i'm just trying to think outside the box here a little bit really outside the box what would a brilliant unaligned

ai do you could yeah you could get sick too take a bunch of sick days but i feel like that would make you sad the question esker says i talked to my manager about the lack of productivity from the team and nothing has happened and i think you know when you're having a discussion like this now Did we say this is just one team or is this a team in a bigger company? I'm going to assume it's a team in a bigger company. It says software startup, but yeah, I'm assuming it's not. This isn't the whole company. This is one team.

Yeah, so like the option to go to another team is potentially viable. You always have the option to go find another company, of course. It may be a little bit harder to do, but when you sit down with your manager, I think it's worthwhile to let your manager know through a very carefully constructed story that this team is not working for you and you know that's not how i would say it the way you need your manager to hear it is you need them to know that you are considering other options because this team is so unproductive and that you want to work on a productive team your manager needs to understand that now there are ways you can say that without sounding like a threatening jerk

there are also ways you can say that without bringing up the the very the potentially very real health issues here and one way to craft that story again back to the polite fiction kind of thing is like, Hey, it's, it's really important to me to work on a team that is doing their best work and really productive. I'm, I'm a little concerned that our team hasn't been able to do that. And it's making it a little bit hard for me to, to see myself here in the longterm, you know, and, and I, I know you want to have a really productive team too. So what, what can be done about this? Like, how can I help with this? And that that's kind of where you turn the story into like, how can I help and contribute? But you've also planted the seed

in your manager's mind that you're going to leave and you need to be prepared to back that up. Because Jameson, I'm with you. Working on a team where you end up carrying all the load and you're just not getting anything out of it. It's just, I don't know, it's a painful way to spend most of your productive waking hours. And to be clear, I think I'm basing this mostly on the vibe I'm getting from the question asker. They don't seem super close to these two sick team members it doesn't i don't get a lot of sentimentality yeah i feel like they're frustrated by the impact on their productivity which not everyone would feel right maybe if you were on this team for a long time and you're close to them like you you want to stay here and it doesn't

bother you as much because if the business is okay with it you're okay with it and you get to still hang out with these these people you're close to and it sucks that they're sick but but whatever that's not the vibe i'm getting it's definitely frustration and i don't think that frustration will i don't think the circumstances will change you can change to be more okay with it or you can go somewhere else i am curious though i'm curious what is behind the frustration you're feeling we don't hit our team goals is not a common complaint i hear a lot from ics and that really we don't need our team goals and no one else cares and it really bothers me like yeah especially because no one else cares it's not like you're getting a bunch of external pressure sounds like

yeah is it just like well i mean if your team goals were more reasonable for with your capacity is is that what bothers you is it no i do want to do a lot more and we just can't as a team i think it might be worth yeah maybe you know and you just didn't put in the question but it's probably worth introspecting that a little bit if you don't have an answer that's what it sounds like to me is like i know this team is capable of so much more and it just feels bad that we're operating below our potential i mean pivot to curing cancer that's you could cure the diseases oh yeah that's an option yeah what are you doing in software you could make this team productive yeah hey what are you sick with hang on let me go prompt claude really quick

have you tried vitamin c yeah claude said acupuncture fixes it i think then go get your hr team to introduce an acupuncture benefit and problem solved there was that blog post a while ago about somebody whose dog had a rare disease and then they used llms to like synthesize a cure for them specifically did you see that yeah i think i did see that i'm assuming that means you can do the same thing for this disease for this human i'm sure that's how things typically work yes so do that it's a blessing of disguise and i can make the most of it yeah i think if if your attitude does not change you will be miserable yeah on this team and so it sounds trite but your options are change your expectations for your co-workers

or change your co-workers yeah or just yeah like well actually a sub option in the change your expectations category is just be grateful you're not working for a spammer yeah yeah it could be or for someone who would fire somebody for having cancer i keep saying cancer again i have no idea what this is and cancer is very sad right and it would suck to get fired for it and your company hasn't so that's actually kind of great like you work for a very humane company yeah yeah that's one way to look at this you could ask your manager to hire a couple more people to kind of like offset the productivity losses yeah i feel like that's probably not gonna happen yeah probably not i don't know you're still paying these people yeah i there's also um one last thing i'll say is

it's possible you said my manager can't manage with enough rigor to produce results again this is a tricky situation and it's very possible there are sensitive discussions happening which you are not privy to this is the kind of thing that i think would not be shared with the team if someone was so sick that it was impacting their work performance quite a bit and the manager was trying to figure out what do i do about this they're not gonna pull you aside and say hey i'm thinking about firing this sick person will that make you feel better or i legally am not allowed to fire this sick person and that really bothers me just so you know like and i'm also not legally allowed to talk to you about this situation yeah oops so i didn't carry on yeah yeah tricky tricky

issue it's such a cliche but health is very important and it's very easy to take for granted How many soft skills problems have I had in my life that are just not related to this? And pretty, pretty nice. Yeah, for sure. It's probably the number one most important problem not to have. Yeah. And good news, listening to this podcast improves your health. I guarantee it.

I think there was a study that just happened that said people who listen to this podcast are all alive. I think we just have to classify this podcast as a supplement and then we can say whatever we want about it. Yeah, exactly. The FDA can't. That's right. and the fda can't do anything about it that's right we promote longevity health happiness and get your vitamin soft skills this is a great supplement though it really is yep all right dave i think that means we're done okay 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 and ask your questions about any topic that we would like to answer and thank you thank you so much to everyone who fills out that form each week we really appreciate it and to those who send me random emails about completely off-topic subjects that you'd like to have a guest on we don't thank you for that but we do thank you for filling out our form to ask a question yep thank you thank you we'll catch you next week