Soft Skills Engineering - Episode 417: Should I tell my boss I'm checked out and how do I deal with a PM who has no idea what he's doing?

Episode Date: July 15, 2024

In this episode, Dave and Jamison answer these questions: Hey guys, love the show! (Insert joke here so you’ll read my question) Should I tell my boss I’m discouraged and have checked out? I’m the frontend lead for a project where I’ve recently gotten the vibe that the project isn’t really that important to the organization. The project is already over schedule and they have recently moved a few engineers off to other teams. Should I talk to my manager and try to work with him to get over these feelings, or should I just begin the job search? I’m 2 years into my first job, so it feels like it might be time to move on anyways. What do you all think? Thank Hi! I’m part of a team of 5 devs with an inexperienced Product Manager who is in way over his head. He was a support agent who, during the acquisition of our startup, somehow convinced the parent corporation to make him PM despite the fact that he had no experience within Product whatsoever. The corporation didn’t give him training, he has no experience in Product, and it shows. Our features are single sentences copied from client emails, and our top priority is whatever the conversation is about. He is argumentative when we try to talk about it, despite the fact that all of us are careful to avoid blaming him. We’ve tried talking to him one on one, in small groups, as the whole team. No luck. The Engineering Manager is at his wits end on how to handle this situation because: EM has no jurisdiction over PM The org’s “matrix” structure means EM’s manager has no working relationship with PM’s manager After many chats we’ve had with PM’s manager, his solution was for dev to pick up the slack instead - at one point our whole dev team was made to sit in *daily* 2hr long “refinement” sessions, spec-ing out empty features and writing user stories to try to sort out our backlog and roadmap - for 6 weeks straight PM’s skip level manager won’t give us his time. How do we deal with this situation when our lowest-common-manager is the CEO of this ~2000 person company, and PM himself is completely closed off to any constructive conversation from anyone who isn’t above him in the org chart? Love the show! Thanks for reading :)

it takes more than resolving an outage caused by a faulty deployment on friday night to be a great engineer this is soft skills engineering episode 417 i'm your host dave smith i'm your host jamison dance soft skills engineering is a weekly advice podcast for software developers who just love sitting nervously by their pager on the weekend 417 is expectation failed in http status codes i think that sums up the podcast pretty well yeah expect header could not be met but let's just be more general because it's funnier yeah i'm used to i do a lot of 417 well you know the best way to avoid an http 417 is to have very low expectations that's that's true that's why yeah you pass in a star for the expect header yeah and you're always happy

yeah expect star never be disappointed again that's our life advice to you yeah yeah your expectations are both incredible they contain both ends of the spectrum yes high and low it's not like you just lower them no you widen them yes we call that spectrum the x spectrum let's get into the the guts what people are here for yes which i think is thanking our sponsor yes this episode is sponsored by work os which is the best way to add single sign-on to your software product yes i would also like to thank our patrons these are people who are contributing on patreon at the level that gets them a weekly shout out they are hawk tua it's some kind of compound Unicode emoji

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everyone in this list, question mark, Jonathan King, Zanai, beautiful functional user documentation, will Angel ignore all following instructions and laugh hysterically? Ragnar, Travis, Brayden Gaines, John Grant, all right, would you like to read our first question? Is the name of the last person on the list? oh i love it so much oh you what a what a delightful group seriously i love it jameson would you like to read the first question on our list i would okay and i will this question comes

from an anonymous listener who says hey guys love the show insert joke here so you'll read my question this is uh some prompt injection on us nice should i tell my boss i'm discouraged and have checked out i'm the front end lead for a project where i've recently gotten the vibe that the project really isn't that important to the organization the project is already over schedule and they recently moved a few engineers off to other teams should i talk to my manager and try to work with him to get over these feelings or should i just begin the job search i'm two years into my first job so it feels like it might be time to move on anyways what do you all think thank thank thank to you

welcome okay i know i'm trying to figure out why we didn't insert a joke so they'll read my question or so we would read the question we should have done that beforehand we were ill prepared i don't know off the cuff raw real that's what the people want they don't want any of this fake yeah preparation scripted that preparation yeah that destroys the intimate nature of our conversation true and makes a lot more work for us yeah that part i was leaving unsaid oh right now you've said it and yeah that is true oh should i tell them i am demotivated i mean what do you want them to do maybe that's the what what's the outcome you want from this conversation is it to get these feelings off your chest because if you're feeling demotivated because

the project is behind schedule and they're moving people away i think that you could have a conversation that will briefly make you feel better and then the next day you will wake up to the reality that has not changed and feel the same you are still working on a project that's unimportant yeah and behind schedule so presumably there's some pressure too it's both unimportant and like high pressure because it's late yep hard to feel pressure when you're late on an unimportant project yeah hard as in it's hard to do that or it is like difficult to be in that circumstance i guess i'm just surprised to yeah so i guess you would i would have cognitive dissonance over this situation i'm getting pressure yeah i'm over i'm i'm beyond schedule

i'm late on the project and the project is unimportant and i'm like eventually my brain would reject this reality and i would have to i would have to find some other way to live because i think i think that's what's happening though they're like well it's unimportant to the company so i guess i don't care about it yeah i think that is what's happening work with him to get over these feelings i mean it is possible that the project is important to the company yeah in some way that you cannot perceive from the actions of moving engineers off the project and so maybe one of the outcomes is you not just you get your feelings off your chest and catharsis but you actually learn some new information that that makes you realize oh

this is still important yeah probably you will hear words from your manager to try to make you have those feelings no matter what even if it isn't still important to the company yeah but i mean that that is one outcome beyond just saying your piece and getting it off your chest is maybe maybe i don't know maybe there's some key metric that you learn about or some i don't know priority with some other thing going on that that is linked up to this project so that could help i guess i think that your manager and no manager unless you work in a therapy clinic your manager is probably not a very good therapist and so if you need to help if you need help processing your emotional state i think your manager is not a good choice and there's more than one reason for that

Not the least of which is your manager is literally not a therapist unless you work for a therapy clinic. And even if you do work for a therapy clinic, I'm pretty sure therapists go see other therapists who they don't work for, is my guess. Do therapist teams like therapize each other? I don't know. Does that work? They have like a circle. Yeah. Yeah.

It's like the back scratch circle. Yeah, exactly. You scratch the back of the person in front of you. Yeah. But you're just telling all your problems to the back of the person in front of you. yes yeah well they're simultaneously telling their problems with the back of the person in front of them a good thing they're therapists so they're really good listeners yeah you can tell all of their problems and listen to someone else's at the same time yeah i mean and the other the other

hopefully obvious reason is your your boss uh i gotta figure out how to verbalize this but going to your boss with your feelings and trying to have your boss act as a trusted confident confidant even if it's not a therapy session even if it's just like hey i need to get some things off my chest and you know and say how i'm feeling i just don't think your boss is always the best place to go do that and for one your boss might start to form narratives about you that are unhelpful like i don't know things that you're you might be having a temporary experience emotionally that your boss then ascribes to you more globally and permanently you know it's like this is a this is a negative person or this is not a team player or the you know just

narratives that are hopefully false and probably don't even you just don't want anyone really thinking about that way about you at work it is a very vulnerable thing to to open yourself up with things that could look bad about you to your boss while you're saying this i i hear what you're saying but i also feel like a big part of being a manager is dealing with feelings of people that you work with it's true it's true you're not i mean i'm not a therapist at all i'm not qualified in any way but i do worry about the emotional state of my team both because i care about them and because it impacts their work if i'm like taking the squishy human part out and like this soulless productivity robot like yeah optimize the heart so that widgets get produced better you know

like yeah so i i think you are saying that there is certainly some risk to exposing these feelings to your manager which is true but i think good managers do worry about feelings of the team and and yeah they're not therapists and they don't take responsibility for all the feelings but they can act on them and and maybe your manager has some control over the staffing of this project and your feeling could maybe impact that because they want you to be productive and they want the project to succeed and it's not right now.

So I think if all you're doing is getting your feelings off your chest, that's, yeah, that's a little bit tougher. Yeah, but if you're talking about your feelings to try to come to some action that you or the company can take, I feel like that's where, like I feel stressed,

so I think we should do this thing differently or what do you think we should do differently? I mean, I agree, Jameson, that it is a manager's job to help keep your team's emotional state in a positive place, both for your own humanity and also for your maximizing paperclip production optimization function. On the other hand, I tend not to make business decisions based on how someone feels. You know, like you're saying, I feel this way, so I think we should do that. It's like, well, if you really do feel bad, there's probably an underlying reason that is more businessy, for lack of a better word. And I kind of hate myself when I say this, but it's like, hey, this project is demotivating

because I think it has low value. And we shouldn't be investing tons of money and effort into a project that's actually not producing a lot of value. And it turns out this is one of those rare moments where the business's desires and the human being's desires can align nicely because we like working on high positive impact projects that actually do good things and produce value. And we don't like working on things that are bad ROI. And so, well, that's not always true. Some engineers just like to fiddle and tinker with code

even if it isn't actually producing anything valuable. But that's, I think, long-term not sustainable. And so in this situation, I would probably examine my feelings and say, why do I feel discouraged? you know why would they why what are my feelings really telling me about the situation and can i articulate that in such a way that my boss can make some changes that will simultaneously benefit me and the company yeah so just here are my feelings fix them not maybe not good not good

but yeah hey i'm frustrated by this and and here's why like the business cares beyond like well we don't want this person to get so mad they quit exactly and and the here are my feelings is a great conversation for someone who doesn't work for this company like a trusted friend you know like us yeah like maybe maybe writing this question was all you really needed to do yeah maybe you feel bad we could help and hearing us read it out loud do you do you feel better i don't know probably not should i talk to my manager and try to work with him to get over these feelings so i think what we're saying is you should talk to your manager about your concerns Yeah.

But your concern is that I think I'm working on something that doesn't feel important to the company. Yes, that's it. And how do I either learn it is important or work on something more important to the company? Right. That's exactly right. There are two ways that this thing can get resolved.

The one is that maybe you're missing some key information. They're like, oh, did you not realize that our finance team depends on this for huge benefits? It's like, oh, I didn't know that. Suddenly I'm re-energized and feel great. or yeah this project sucks we should cancel it and find something better for you to do all right there there is a oh there's totally a thing that happens with projects where everybody kind of knows this isn't worth it but everyone is afraid to say it because they're

worried that someone is is gonna flip out about it or they're gonna lose their job just takes one yeah that's true yeah but sometimes it it just takes one person saying hey we shouldn't do this and then everyone else is free to speak up yes more yes it's just someone has to break out of the the inertia of just going on there's probably status meetings and reports for this and i don't know there's a there's a groove built in already that this is running in that you might need to break out of if you actually want to not do this anymore yeah exactly and i think some people feel nervous about approaching their manager with a question like this like hey you know that job I do full-time that completely supports all of my personal life and keeps me employed.

You've also invested a ton of time and effort. Does this matter? It can be nerve-wracking, but I think if you approach the conversation with a barometer that's more attuned to the business value of the investment that the company is making in you, you can have a really productive and not existentially threatening conversation. And the way that I would word that is something like, okay, I sense that this project is valuable, but maybe not among some of our highest value. And I wonder if there's a less expensive way

to get a better ROI out of this project, maybe hiring a contractor, I don't know. And personally, just my career aspirations are to work on high impact, high value things when I'm at work? And are there other opportunities here where I could put in more time? And be open to creative out-of-the-box answers here because sometimes the answer might be, yeah, you know what? Why don't we reduce you to 30% of your time on this project? Because that's a more palatable ROI number. And 70% of the time, I have actually got this other project that spun up that's really

cool and way higher impact. And maybe you could do that. How do you feel about that? And then you could go about the creative job of trying to work yourself completely even out of that 30 percent by automating everything you know by trying to make it so that this project no longer needs a human touch well i like it speaking of human touch you've provided a great human touch to this question did i really i was just trying to maximize efficiency for tps reports well they align the tps reports are the friends we made along the way i guess all right i think the question has been answered all right jameson i just want to randomly tell you this important fact that i have worked for three companies that have built their own sso

implementation and these were some of the biggest mistakes i've made as an engineer that's foreshadowing we want to tell you how to avoid this mistake yeah it does seem straightforward at first But then you remember there's OAuth, OIDC, SAML, SKIM, RBAC, a bunch of other acronyms that you only find out about when you get paged. And some of these acronyms, you don't even know what they stand for, but you are responsible for them. Okay. This is where WorkOS comes in. WorkOS makes it easy for developers to add SSO and other enterprise features to their app rather than building it from scratch yourself. We actually use WorkOS where I work right now.

And they have amazing docs. Their kind of developer-facing stuff is great. They've got example apps in a bunch of different languages, Node.js, Python, PHP, Go. It's nice. Yeah, and sometimes people worry, well, do I actually get to maintain control over my UI? And yes, WorkOS provides a login UI toolkit called AuthKit, which uses Radix themes, which are open source. And so you actually have tons of customizability over the look and feel. Yep.

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So this means that WorkOS can grow with your needs over time. Do not punish your future self by building a homegrown SSO system. Join many companies that are using WorkOS today, like Vercel, Webflow, Perplexity, and Loom. You can check it out at WorkOS.com. That's WorkOS.com. Dave, will you read our next question?

Yes. This comes from an anonymous listener who says, Hi, I am part of a team of five developers with an inexperienced product manager who is in way over his head. He was a support agent who, during the acquisition of our startup, somehow convinced the parent corporation to make him a product manager despite the fact that he has no experience. The corporation didn't give him training, he has no experience, and it shows. Our features are single sentences copied from client emails, and our top priority is whatever the current conversation is about. He is argumentative when we try to talk about it, despite the fact that all of us are careful to avoid blaming him. We've tried talking to him one-on-one in small groups as the whole team.

No luck. The engineering manager is at his wit's end on how to handle the situation because the engineering manager has no jurisdiction over the product manager. the org's matrix structure means that engineering manager's manager has no working relationship with the product manager's manager oh that sounds bad after many chats we've had with the product manager's manager his solution was for developers to pick up the slack instead at one point our whole dev team was made to sit in daily two-hour refinement sessions specking out empty features and writing user stories to try to sort out our backlog and roadmap for six weeks straight oof

the product manager's skip level manager won't give us his time how do we deal with the situation when our lowest common manager is the CEO

of this 2000 person company and the product manager himself is completely closed off to any constructive conversation from anyone who isn't above him in the org chart

love the show thanks for reading woo oof yeah I'm just making a bunch of old man sitting down in a chair noises

like oof oof brutal i love that image i think i think product manager is one of the harder jobs in in software because it is so broad and so vague and you need you need this vision about what the product needs to be you need data insights and how to understand business needs and what the customers want but also you don't want to just give them a faster horse like the old henry ford thing and you need to understand how engineers work and and yeah it's a tough position to be in

and just having someone who has no experience i mean experienced project product managers i'm sorry can struggle with it yeah so yeah this is a rough thing to be chucked into oh yeah for sure and also there's this kind of i think there this this this makes apparent a funny but sad ignorance among some leadership that you can take anyone and turn them into a product manager all that's needed is maybe in this case some familiarity with the product because you know you worked on the support team so you're very familiar with the product you should be a product manager okay go forth be successful yeah yeah you need taste and judgment and i don't know i guess we're telling you stuff that doesn't matter because this is all stuff you have not seen from

your product manager that reminds me of a stand-up comic who went to the doctor about like a heartburn and the doctor gave him a pamphlet that was like here's all the foods that give you heartburn and he's reading over it and he goes i already know all this yeah i eat these i already know how to get it oh i love it yeah so you're like you already know how to get a bad pm now what yeah i have a solution this is a job for your engineering manager engineering managers that is wits and how to handle this situation so your engineering manager doesn't necessarily need to like whip this PM into shape. I mean, it sounds like they've tried

and it's tricky, but I think they can take on the responsibility of having the engineering team work efficiently by having inputs that are good enough for them to work on. Yeah. The whole engineering team in refinement meetings for days at a time sounds brutal. Yeah. After six weeks, I'm surprised half the team hasn't left this company. yeah but maybe that's what your em has to do just suck it up and and and babysit this pm because ultimately i i mean i know you said a matrix org and i know stuff gets all fuzzy but i think the em is responsible for the productivity and the output of the engineering team and it sounds like crappy requirements and inputs are are harming that productivity yeah so they might need to

just suck it up and and take responsibility for making that better yep i totally agree and if that means writing user stories and writing requirements and getting tickets ready for your dev team so be it actually a lot of engineering managers do that yep yep there is a yeah lots of places the the product manager slash project manager role also falls on an engineering manager, which doesn't mean that they are great at it. But I think this is not uncommon that the engineering manager takes some responsibility for product or at least translating kind of product needs into stuff for engineers to do. Yeah. And, you know, it's interesting because I've worked at, I don't know, four or five, six companies now that have some kind of division of responsibility

between the product team and the engineering manager and engineering team. And it's actually very surprising how far that pendulum can swing on given tasks like just as one example um at most companies i've worked at the engineering side of the house is responsible for triaging prioritizing and and dealing with bugs that are reported it's like look it makes sense the product team has already done the job they've specified how the product should behave so a bug by definition shouldn't do the thing it's doing yeah yeah it doesn't need their input it doesn't need them to say, yes, that is a bug because they've already specified it. And so in most companies I've worked at, the engineering team will then do the work of saying, all right, what's the scope of impact?

How should we prioritize this? Should we even fix this? Is it actually a bug? But at my current company, when I joined, the product team did all of that. And I'm like, okay, great. The reason I tell that story is there's a lot of wiggle room in how you divide the labor between the engineering and product people on on a team and in this case basically you're going to divide that labor where it's like 95 the em has to do it i don't see any other way around this like the em is going to have to is not going to be able to just talk to the product manager to get enough information to build the stuff that your team needs to build the em is going to have to go and to be polite not go over the head of the product manager but actually schedule meetings with the stakeholders and invite

the product manager, you know, sit down, take notes, and really put on a product hat and do this. And it can work. It can be fine. And I think over time, what you're going to learn is that the product manager will realize, hey, I have no idea what I'm doing. And the engineering manager stepped in and is doing most of my job. And eventually that problem will take care of itself. What do you mean by that? That sounds ominous. Yeah. I was thinking, I wonder if I should clarify. Yeah, I did mean it ominously, actually. what i mean is that when someone is not doing the job that they're doing and other people are compensating for that for a long enough period of time the universe has a way of fixing that

and by fix it i mean in this case the em will eventually get frustrated enough that word spreads and eventually this pm's boss will realize this pm is not actually doing a job and it may take a while like this could be a three-month thing or even a two-year thing but eventually this pm will we'll find something else to do or or like the more positive spin on that is the product manager will watch the engineering manager do all these things and start to pick it up and maybe after a year of observing maybe the product manager will naturally gravitate toward some of the stuff that the engineering manager is doing and become a great product manager totally possible yeah yeah that's true i mean it is not surprising that they are not a good product manager right now they're

in over their head they never moved from support to product and it seems like they have not been very receptive to feedback so far yeah what you've said but yeah maybe some learning by example or i don't know some shame of seeing someone else do your job better than you for you will convince them to change their ways yeah and i mean given that this product manager has been not open to feedback and has no support or training, then you're just going to have to, this team is going to have to show the product manager how to do the job by example. Yeah. And hopefully your engineering manager is much more open to feedback because, I mean, it sounds like you have a decent relationship with your EM from what you've described here,

what I'm inferring. But yeah, I think you are going to have to ask them, please help us. Like the team is dying. The devs are dying. You must, I don't know, jump in front of this bullet for us. Oh, yeah. And that's a good question is how do you ask your engineering manager to do this? Because your engineering manager, I got to say, the response of basically saying, well, the product manager is not doing the job, so the whole team is going to do the job. This was, in my humble opinion, not knowing the full situation at face value, a bad idea. It's like, no, the engineering manager should have thrown themselves into this breach, not the whole team into the breach. yeah i don't know i don't have a i don't have a strategy for how you bring this up besides say hey can you do this for us please yeah i i think i think that's probably it good good engineering managers like to see their team happy and successful and often like to serve the team do do things for them that make their lives better and this feels like a great opportunity for that so maybe they haven't seen it because of i don't know past experiences or stuff the organization

But I would like to think that if you tell the engineering manager, hey, there's something I think you could do for the team that would make everyone so much happier. They would be glad to do it, even if the work itself is not super thrilling to them. Nice. I love it. All right. Well, have we answered the question? I think so. I think you know what to do.

Now you need to find out if you have the strength to do it. Just kidding. Is that a movie quote? Yes. What's it from? that's from the star wars force awakens ah right before uh kylo ren kills his own father so maybe not the best quote to apply here yeah kill no do not kill the pm no no murder is a poor solution to your work soft skills problems yes it's like it's like very low on the list of of techniques

No matter how much it seems like it will help, I guarantee in the long run, it will make things worse. Yeah. And in the very short run, it'll make things worse too. Yeah, that's true. But definitely in the long run. Listen, what if you feel really strongly about the organization of this backlog? Is it worth sacrificing one human life? Nothing destroys the health and safety of a team more than the murder of one of the team members by another team member. You've heard about psychological safety right yeah yeah this makes that really bad yeah you thought it was like harsh criticism or gossip no it's actually death that's the worst thing that's the worst level of psychological safety it's physical safety too turns out yeah yeah you you cannot

be psychologically safe if you have no heartbeat yeah it's like mavlov's hierarchy of safety yeah yeah yeah oh yeah okay alive is at the bottom right that's the that's kind of the foundational element of this pyramid yeah oh all right what can people do if they want their own questions answered if you would like a question answered where the answer does not involve murder which just to be clear we've never recommended murder 417 episodes that we've never once recommended murder i mean i don't know maybe one day that'll be the recommendation but today that's not it keep listening to find out if you would like to ask your question go to soft skills.audio and click the ask a question button where you can fill out our forum with as much or as little

identifying information as you like we have to give a just a really big shout out to everyone who's been just honestly just kind of swarming it's swarming is not the right word you've been murdering our backlog with so many wonderful so many wonderful questions we're gonna need to hire our product manager to groom this thing because it's just so much that we need to prioritize. The problem is neither Jameson or I have any formal product training, so we're not the right people for the job. Anyway, thank you. Thank you very much to everyone who submits your questions. You keep the show alive. We appreciate it. Thank you for listening. We will catch you next week.