Soft Skills Engineering - Episode 222: Cowboy CTO and underpaid after promotion

Episode Date: August 10, 2020

In this episode, Dave and Jamison answer these questions: Questions Hey, long time fan of the show! Our current CTO came in as the result of a merger. For most of his life, he was a solo developer and owned his own company. The struggles we are facing now are: He is not responsive at all, neither via chat, nor email, nor any other communication tool. He often says “I’ll do it” but then takes weeks to finish He has thousands of unread emails in his inbox When he writes tickets, the details are unclear for others He codes way too much for a CTO, in my opinion, and his code is a bit messy compared to the other developers Since he is a really nice person, we all want to give him feedback that makes him understand his role better, and to avoid being a bottleneck. I know that changing another person is hard, but at the same time I know that he is motivated to become a good CTO. How do I help him?” Hi. I’ve only recently discovered your podcast this quarantine, and it’s been really helpful at work already. So when I was faced with this problem, I immediately thought of you! I have been a professional software developer for just over a year and have received great feedback from my manager and team. During my performance review, I asked what I would need to qualify for promotion. I got the news that I had already been recommended for a promotion! Meanwhile, a friend still in university got an entry-level job offer from my company that pays more than I would make if my promotion went through. Where I come from, there are no negotiations when companies recruit at universities, so it’s not a matter of them negotiating a better deal. If the promotion does not come through I have no qualms trying to negotiate. If the promotion does comes through, would I come off as ungrateful if I bring this up? Am I asking for too much by wanting to be paid more at a higher position than what a new grad would be paid at entry level? I know it’s not an ideal world and I feel greedy as I type this, but I just want to be compensated for what I think I’m worth. I also think that it also comes down to my ego at some point. SEND HALP

it takes more than using a tiling window manager to be a great engineer this is soft skills engineering episode 222 i'm your host dave smith i'm your host jameson dance soft skills engineering is a weekly advice podcast for software developers about the non-tech stuff excluding how to tile all the windows i mean tiling came from like tiling a floor so that's not super technical right it's home improvement based it's not technical based it's not technology but it is a technical skill yeah that's true also a popular window manager has the name moan has the word monad in its name so i have to make fun of it oh and what's that x monad oh i never heard of it yeah there's a window manager written in haskell and you can tell because the name is x monad

oh my gosh but it's relatively popular among people who aren't like pumped that it's written in Haskell even. They just like the window manager. Well, I do have to say that this is a very non-scientific statement, but some of the best engineers I know use tiling window managers. Yeah. Are they the same engineers who turn their monitors vertical? I don't think so. Those are some pretty good ones too, though. I use like the dumbed down, fancy, shiny Mac OS version, which is just like shortcuts that I can use to switch windows around to different sizes but i feel like i want to i want to watch someone who's way into tiling window management and just look at them and figure out how backwards my

workflow is i use a series of shortcuts where i actually put my hand on this device called a mouse and i move it around to to reposition and resize my windows it sounds so efficient it's pretty good i never have to lift my hand off the mouse you know that mother of all demos that doug engelbart did in the 60s at xerox yeah it's like the one where he shows off the mouse for the first time and it was like totally revolutionary and it is kind of funny that now it's uncool to use a mouse in some circles if you're an engineer it's like this incredible user interface invention that is now lame lame it's all about the foot pedals now the vim foot pedal i want to thank our wonderful patrons thank you so much to the folks who support

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that's true i'm pretty short and economy class is is very comfy it's also comfier because i i take my shoes and socks off and just stretch my feet out onto the armrests of the chair in front of me it turns out you have tons of room if you do that yeah perfect you just have to buy that seat though well i haven't i have a hack i discovered where i don't buy the seat i just do it air travel life hacks yeah just annoy everyone around you and sometimes the air marshals let you get away with it yeah all right i'd like to thank veteri for sponsoring this episode veteri is an online marketplace where job seekers can find employment in the development industry go to veteri.com soft skills and you'll hear more about them later hey you want to read our first

question i do this is from a listener named turtleneck hey guys long time fan of the show our current cto came in as the result of a merger for most of his life he was a solo developer and owned his own company the struggles we are facing now are he is not responsible responsive he's not responsive at all neither via chat nor email nor any other communication tool he often says i'll do it but then takes weeks to finish he has thousands of unread emails in his inbox when he writes tickets the details are unclear for others he codes way too much for a cto in my opinion and his code is a bit messy compared to the other developers since he is a really nice person we all want to give him feedback that makes him understand his role better and to avoid being

a bottleneck i know that changing another person is hard but at the same time i know that he is motivated to become a good cto how do i help him thousands of emails in the inbox huh amateur are you one of those people that just leaves emails unread no i am a compulsive email filer yeah that number has to go down yeah i do have friends that have tens of thousands of unread emails in their inbox and i don't understand how they function how i don't know how do you even muster the strength to get out of bed in the morning when you have to confront that every day exactly maybe they're motivated by seeing that number go up every day they're like i wonder how hyatt got today it's like a stock price they're like yes i'm rich unread emails up 30 over the

past quarter yeah there's the there's the part that tickles my brain in unpleasant ways of just seeing that number be really large but there's also the pragmatic part of like sometimes email is important and if you just never read it doesn't that cause bad things to happen sometimes yeah although surprisingly it doesn't cause bad things to happen a lot of times if you don't read it yeah i guess yeah maybe that's the other reason why i don't like it is because it makes me feel like all this time i spend into reading email and making that number go down is a total waste where i could just do nothing and then eventually someone will yell at me and i'll be like okay that's one email that i should have read out of like 40 000 i'm fine with those odds it's good

that's like five nines yeah he's unlocked the secret the thing i latched onto in this write-up was he takes weeks to get things done he gets things done impressive what a go-getter yeah he says i'll do it and he delivers that's great i think a bad version of myself could look something like this where i'll say yes and just ignore stuff. I'll, I'll try and juggle too many things and drop the ball. I'll hide away in the code because it's comfortable and comforting and easy to make progress on. So I, I can feel the pull of this approach. This is like the, I'm an engineer who got pulled into management style

of management. Yes. Can't you just leave me alone so I can do engineering stuff, even though I am a manager or an executive. Even though I happen to be running the entire engineering department of this company. Listen, just because I'm a CTO doesn't mean you can email me asking for like budget reports or something. I just want to code, man. Yeah. It sounds like he hasn't adjusted to what his job actually is and he's still trying to do the job that he wants it to be, which it is not anymore. Yeah. Which is I'm a solo business owner running a company and writing all the code and having a great time. Yeah. Leave me alone. Yeah. I mean, there are places where a CTO is sort of like a super individual contributor. And if they're small enough, then a CTO is kind of

just like the individual contributor. Yeah. But it sounds like that's not the case. If there was a merger and there's a team that this person is responsible for, it sounds like there's at least several people who depend on or interact with the CTO. And he's sort of just ignoring that. I just want to know how this decision process went down during this merger. They're like, okay, let's combine these two companies. On the one side, we have a dozen engineers or more with the leadership structure of some kind. On the other side, we have a solo code-slinging technical founder cowboy. Hmm, who should we make our CTO?

Maybe, I mean, it doesn't say who it is, and I'm sure it's not this person, but maybe it's like the guy who wrote Redis, you know? Like, clearly technical expert in this very specialized field. those people sometimes become ctos but like that guy likes to write code he doesn't like to manage teams at all and i could see how that might happen where it's someone who who built this thing that's core to the company or just like very very very super expert at something but doesn't doesn't enjoy all the stuff that comes attached with that once you get acquired maybe this cto is actually working a second job during covid maybe he's an intern at google yeah it would take a little bit

longer to get stuff done you had a second job i wonder if he doesn't understand the effect he's having on the team especially if he's coming from a solo developer who owned his own company like maybe he thinks he's being really productive and everybody is just bothering him and keeping him from being productive but if you point out that say you're blocked waiting for a pull request review or there's some approval thing he needs to do or the team is unsure about what to proceed how to proceed and they wait like a week for some feedback or decision from him seeing the impact of him avoiding these uh kind of more group focused or communication related responsibilities might motivate him to change if he just doesn't know how bad it is for other people because of this

then telling him how bad it is for them might help. I think that might actually work in this case. I mean, the question asker says, well, I should say Turtleneck, which I'm sure is your real name, says the CTO wants to improve. And so, I mean, just tell him. Yeah.

I think that's a great idea. Have you ever done that? Delivered critical feedback to a superior? You know, it's hard because every leader says, I want your feedback, but they don't really want your feedback. I welcome criticism. It makes me stronger.

My door is always open. So my impression is that his boss was like suspected this was a problem, but felt like it would be more effective if he heard about it from his peers instead of his boss just saying, hey, you need to fix this. Sort of the subtext I got from this. But I mean, that might be a good point. You could talk about instituting 360 reviews as a really backwards roundabout way to doing one very specific 360 review from you to your cto yeah i mean that's like the nuclear option but it

works probably say what you will about nuclear weapons but they work they they do what they're supposed to do they sure blow stuff up yeah boy do they and they leave the earth uninhabitable for generations. Much like 360 reviews. Those also blow stuff up. Yeah. So that's one option is to kind of encourage a 360 review process of some kind for everyone and just make sure the CTO is not exempt. It's the easiest thing in the world for me to say, just tell him. it would be hard to tell him though i'm trying to think of times well i i think i think you could do this like the beauty of this situation is you don't have you're not dealing with like a character deficiency yeah where you have to say like you're not smart enough you know that's not what you're

dealing with yeah this is strictly behavioral stuff that is discretionary so you could say things like you're on the critical path too much and it's slowing down our team's velocity and you can give examples right that kind of feedback is totally feels a lot safer to give than i don't like your demeanor or you're not very smart yeah you mentioned being on the critical path too much and i think i was kind of imagining this was someone who isn't great at communicating but it's also very possible they just are juggling too many things because they are used to working at a lower level than they need to work right now so they're they're just way down in the weeds and implementation details plus trying to do all this other stuff the cto stuff

and what they really need to do is kind of drop all the implementation detail stuff i don't think it's in the question we read but the original question mentioned something about waiting for a pr review and just don't like maybe your cto does not review code or doesn't block code reviews anyways maybe they can they can hop in and do it if they want to but if they don't have time to do it then maybe instead of waiting for them to have time you just pull them out of that process yeah yeah and that that's actually how you could couch this feedback is not about the person but about process changes to help the team scale and go faster the ticket thing i feel i'm very guilty of that sometimes where i have this understanding in my head of what we should do so the ticket is

like do the thing in my head and then it's like it's like a shortcut to remind me of the stuff i know instead of an explanation for someone else who doesn't have context but now it's for someone else to work on so i think i've even said something like there's like a one word description and then it says talk to jameson for details that's like how i write the ticket to save myself from having to write it all out the instructions are not about how to do the thing the instructions are about how to jog jameson's memory yeah following three key words will make me remember describe this room in his memory palace to trigger it i've done two things to solve that one is suck it up and write it all out sometimes i feel like i can't do that because i'm so busy and then the thing that kicks

me out of that is like it'll waste way more time if i put nonsense here and people have to follow follow up later so if it's important enough for me to ask someone to do and i have all this context i should write it out let me just comment on that real quick like when you ask someone to come talk to you about it all you're doing is kicking the can down the road you're still gonna have to spend the time about probably about the same amount of time as it would take to write it down but that's a problem for later jameson and i hate that guy he gets the short end of the stick so often jameson is just a big loser so that's all i can to ruin his life nice okay what was your second thing so maybe i should not be the person that has all these problem details in my head

like that usually means that i'm trying to own sort of solving the problem and implementing it and another solution is just to divest myself even more from it and that way it's not dependent on me using my smart brain to figure out what to do and then writing it down and communicating it effectively it's more on other people to figure it out and they're not as blocked by me and then i can like swoop in and give feedback if i need to but i'm not the one figuring out everything that we have to do explicitly that sounds very good for future jameson yeah it does yeah i i give with one hand and take away with the other from future jameson very nice well i mean the The other option here is that your CTO is actually a little bit disengaged because this is a post-merger situation and there was undoubtedly some kind of equity involved in the merger of these two companies.

And given that this was the solo owner of that company, there's probably some cash or equity on the line that's got time expiration on it and your CTO might just be running down the clock. Yeah, that's a good point. It's a call out to folks negotiating acquisitions where you need a clause about like email answer rate and your ticket completion and you got to really nail down those deliverables. We will only give you this equity after one year if your 360 reviews are 4.8 out of five stars. Yeah, that's a good point. They could just be resting investing. Oh yeah, possible.

I don't think so though. The turtleneck says he is motivated to become a good CTO. So, yeah, I would talk to him about it. That seems pretty reasonable. Well, have we answered the question? Yeah, I think so. Good luck. This one doesn't seem as terrible as it might have seemed on the surface, given what we know about this CTO.

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If you use that link, you will help support the show. And if you get a job through Vetteri, they will send you $300. Thank you so much to Vetteri for sponsoring the show. Okay, David, you want to read our next question? You bet. This one comes from an anonymous listener who says, Hi, I've only recently discovered your podcast during quarantine and it's been really helpful at work already. So when I faced this problem, I immediately thought of you.

I have been a professional software developer for just over a year and have received great feedback from my manager and team. during my performance review i asked what i would need to qualify for promotion i got the news that i had already been recommended for promotion meanwhile a friend still in university got an entry-level job from my company that pays more than i would make if my promotion went through where i come from there are no negotiations when companies recruit at universities so it's not a matter of them negotiating a better deal if the promotion does not come through i have no qualms trying to negotiate if the promotion does come through would i come off as ungrateful if i bring this up am i asking for too much by wanting to be paid more at a higher position than what a new grad

would be paid at entry level i know it's not an ideal world and i feel greedy as i type this but i just want to be compensated for what i think i'm worth i also think that it comes down to my ego at some point send help comes down to my ego at some point yes doesn't it all though yeah yeah i mean salary is very tied to ego and it's very hard to separate value and perception of value from pay that's i mean i think most people do that yeah which is why my new salary negotiation technique is to tell people to get over themselves that's such an ego you want how much money geez let's work on having you accept the world as it is a little bit more that way i can pay you under market that's right it's in both of our best interest

your mental health and my wallet yeah you'll be happier i'll be richer it's a win-win we both win awesome so it sounds like they're currently underpaid and will keep being underpaid if they get promoted that's my reading yeah me too and if they do get promoted they'll maybe they'll be this glorious ceremony where someone hands you the promotion plaque and it's got a number on there and you're like this number is too low and then they say but we already engraved the plaque so can't change it now i do think there's something of like usually when you get a promotion that is not the opening of a new salary negotiation right so i think if you wait to find

out if you're promoted or not and then say but actually i wanted more than this i don't think it will smoothly result in you getting paid more although i did do that once i had totally forgotten about this but i did wait so did i oh no this was a this was at a much smaller company and yeah same it was at a tiny startup for me yeah so i got this like change in title and my boss told me the new salary and i kind of just looked back at him and said yeah that's that's okay and he was like oh what were you expecting and i and i literally said these words well if it had been x i would have jumped out of my socks and he was like okay and then a week later he came into my office and

said i got you x and i was like oh my gosh i did not expect that to work huh so be lucky yeah i wouldn't expect that to work at most places i've ever worked yeah it yeah i had sort of a similar experience and I don't know why it worked there. But I can tell you, I think you would be much more likely to have success if you brought up the issue of compensation earlier and if it was part of a promotion. Yes. It's basically never too early to bring up comp. If you have a comp concern and you wait, it just gets worse. It just gets harder to fix. Yeah. I think I would suggest bringing it up right away. If you're going to negotiate for that rate either way, whether you get the promotion or not, then I don't know that there's harm in asking or bringing it up right

now. And it can be easier to do a salary adjustment as part of a promotion instead of just like a random raise out of nowhere. Yes. Yeah. Because if you wait until after the promotion, you have to understand there's been a bunch of paperwork and red tape in the background leading up to that promotion, including a salary change. And now if you wait until after the promotion comes through, you're basically asking them to do all of that again yeah i used to be confused by this and think it was laziness of like oh i don't want to i don't want to like submit this form again but it's not that at some places there there there are like these gigantic complex machines that get set in motion that depend on months of meetings and committees and approvals and like it's not even

that it's that much work for you to do it's that there is a lot of other downstream stuff that has to happen that right will probably not happen if if it just happened already yeah like there are approvals you have to get you know hr might have to weigh in various levels of leadership might have to weigh in and approve and i remember doing when i was in management and i did salary negotiations with people and they would come back to me and ask for just a tiny bit more i would just kind of cringe because i thought okay i'm gonna have to go back and i have to talk to my ceo i have to go to hr i have to fill out this form is it real like do you really for like a thousand bucks a year do you really think it's worth it like just you should ask for

more you know it will cost me ten thousand dollars to ask for more money so you better make it worth it yeah so yeah i i don't think your promotion has anything to do with this question at all the fact that new hires are coming in and being paid more than you is enough to justify a raise because at this point you have a year of experience not just in general as an engineer but also on the domain of this company, which means you are inherently more valuable. Now, the fact that you're up for promotion means that the company thinks highly of you anyway, so you're in a good negotiating position. But new hires coming in should not be making more than you if they are coming in with the same amount of experience, same educational qualifications and whatnot.

So I would not feel bad at all asking for that, even though it's awkward. But the way you do it is you bring in the data point and say, I'm aware that new grads are coming in at X. I would like to be making you know x plus five percent yeah just make it simple and and don't be afraid to ask for a very specific number i think a lot of times we we sit down with our bosses especially you know more junior engineers and we're like well you know i'm going to kind of beat around the bush i'd like to make more but i don't want to i don't want to seem greedy just ask them like they deal this is their stock and trade management deals with these numbers all all day long it's what they do so just say look i make x and i'd like to make x plus five percent i like it i'll

pay you one percent to do it for me commission sounds so certain yeah yeah i think you're right i was going to ask how you use this data point of of your friend and it sounds like you're saying don't mention hey person x told me how much money they're making yeah but just you know in general yeah i think so yeah also if you're if you're feeling greedy just wait till you find out how much money your boss makes. Then you will feel even greedier. Yes, you will no longer feel bad for asking for more when you realize that the ceiling is way higher than I thought. Yeah. What sound advice have you given, Dave? Have we answered the question? I think so. All right, good luck. What can people do if they would like their own questions answered? Go to softskills.audio and

click on ask a question where you can fill out our form. Thanks so much to everyone who does it. You keep the show going. If you want to support the show, you can tweet about it. You can follow us on twitter at softskillseng and you can share it with your friends thanks very much we'll catch you next week