Soft Skills Engineering - Episode 213: Interviewing your future boss and screwed by private equity
Episode Date: June 8, 2020In this episode, Dave and Jamison answer these questions: My manager has left, so I have the task of interviewing candidates for my future boss’ position. I’m not doing it alone, one more... engineering lead joins me for my tech round. After this round, the candidate gets to talk to upper management for the final decision. My question is, what are the lines you should never ever cross in an interview when interviewing your future boss. Our company was purchased by a private equity firm this year. Layoffs began immediately. While the company was gradually carved up, leadership continually violated every promise made. This week, during the most recent round of layoffs, I lost my job. I worked my butt off for years trying to contribute as much as I could to make a positive impact for both users and coworkers. Alas, despite all of my efforts, I was proven expendable. It feels like there was little point in doing as much as I did for this company, especially during the panicked response to COVID. How do I find and sustain a sense of security at the next company? How do I ensure that I can safely care about the company—the work done and the people helping to do it—finding that precarious balance between being invaluable and burning myself out?
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it takes more than investing an hour to learn an editor plugin that will save you 30 minutes
over your lifetime to be a great software engineer this is episode 213 of the soft
skills engineering podcast i'm your host jamison dance i'm your host dave smith soft skills
engineering is a weekly advice show where we answer your non-technical questions about the
technical field of software development i wonder if you could add up all the time that has been
invested to learn dvorak in order to type more efficiently i assume it's a net negative some
people learn dvorak to help with like rsi but i guess that doesn't take into account the like
street cred you get which is incalculable there's not really a way to assign a number to that you
got to put a value on that it's not in saving time though it's in you save time because people
think you're cooler so they do work for you instead of you having to do it yourself absolutely
stand back i know dvorak all right dave do you want to thank our patrons yes thank you to those
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by the time this goes out it should have been now i think yeah yeah it's now unless you're hoping for
yeah it's not i it's not now it's donated now it's not now it's soon it's never now but if
you donated when we recorded this it's now perfect all right i'm gonna read our first question this
is from an anonymous listener who says my manager has left so i have the task of interviewing
candidates for my future boss's position i'm not doing it alone one more engineering lead joins me
for my tech round after this round the candidate gets to talk to upper management for the final
decision my question is what are the lines you should never ever cross in an interview when
interviewing your future boss this is great the first line is probably the line of the threshold
of the doorway into the interview room have you ever interviewed someone for a boss position
for your boss have you ever interviewed a potential boss not my potential boss okay i have
once someone else's i mean what do you mean well like i've interviewed people who would be in
management positions but i've never interviewed someone who would be my manager yeah yeah one
time at a startup it was weird in a lot of ways so we were all very young and this was i don't know
what like 2012 or something like that somewhere around there and we were very pumped about
holacracy and flat structures and and we were we read a lot about valve's employment handbook
it turns out when you make billions of dollars in revenue you can do whatever you want for
organizational structure and like it's fine because you have this thing called steam that
makes you billions of dollars yeah anyways we got very pumped about this idea of no bosses
and then the ceo of the company who was older and more experienced but also kind of i think
in retrospect he was pretty good at dealing with us without saying like what a bunch of idiots
i think he decided that we needed some adults in the room and wanted to hire someone who was
essentially going to be the boss but didn't say hey this person will be your boss they were just
like older and more experienced and would take on things that if you squinted looked like managerial
responsibilities but they're because again 2012 a weird time everyone was young their title was
going to be company magician uh just to show you like they couldn't be a an engineering manager
oh no that would that would be against our culture but a magician would be okay
my gosh yeah so so yeah it was it was really interesting the way it played out we had an
interview but it wasn't me deciding if i wanted to hire them it was more like get to know this
person and tell me what you think here get to know your future boss i mean magician yeah it wasn't
I mean there wasn't a criteria we were looking for it's just like do you think you could work
with this person and I did and it worked out okay and I liked him but it was very fuzzy making an
already fuzzy situation fuzzier I think that's that's maybe like one of the least clear ways
you could go into this which is like they may or may not be your boss but you kind of think they
will but you don't know what you're supposed to ask them and you don't know what's going to happen
to add to all the other weirdness of like you don't want to I don't know maybe if you're super
harsh on them then the executives will decide to hire this person but they'll have a grudge against
you because you ask them too hard of questions in the interview or something like ah yeah yeah
there's there's already some weirdness there what was there a moment in the interview when you were
struggling for words and suddenly the candidate like opens up a coat pocket and a flash of smoke
appears and a dove flies out of his coat no but a magic trick that they pulled in this interview
was it turned into them interviewing me and they were just like tell me about what you've done in
your career and talk to me about some hard problems you've solved and i remember saying
words to answer it but my brain was also in another track going like wait what the point
of me having a job so i don't have to get interviewed what's happening that's the whole
reason i'm employed yeah the answer is magic well you know the key in a magician's arsenal is
misdirection yeah judo magician that's maybe what their title should have been yeah like i said i
actually i i like this person and and would work with them again it was just like a weird there's
a lot of weird stuff around yeah this says it is a tech round lines you should cross i don't know i
think if you're worried about crossing lines in a technical interview i think you might have bigger
concerns like i think you should just evaluate their technical skills and and if part of your
evaluation of someone's technical skills involves getting in their face and screaming at them while
they like try and write code on a whiteboard yeah like don't do that but that already sucks
i don't know that you have to do it much differently than you would for an engineering
candidate it's just that the outcome might be like yeah they did well on this thing and not
as well on this thing but we we don't expect them to write production code so like it's okay if they
if they struggled to i don't know do this complicated sql query or something like that
you know ideally what's going to happen is you will ask them a battery of questions or put them
through some kind of process and you'll come out with some opinion about what they are good at
technically and where their strengths and weaknesses are yeah then you just kind of hand
that on and i don't i don't see how that would cross the line with anybody unless your interview
process just sucks yeah although i so i'm i'm imagining that the listener has a little bit
of inner conflict here which is do i go easy on this person so that they'll like me when they're
my boss or do i go hard on them to make sure to weed out any bad candidates and to show them that
you know we only want people here who are super excellent at complicated sql queries and writing
curly braces on whiteboards yeah do you have any say in the outcome because if you don't
then this is a chance to learn about them but not to yes like your goal should be find out what it
would be like to work with them so you can prepare not yes yes into them really hard to to to get to
the the depths of their weaknesses you know and just a slight corollary on that is try to extract
information that can be used for blackmail later when they threaten you with a negative review
ah yeah okay so you ask them to like solve this graph traversal problem but they have to like
do it using like maybe you ask their security questions like you use the name of your your
mother's maiden name is one variable name and like the last four digits of your social yes
that's the other yes first pet name
you have to be very subtle about this like weave it together over the course of three or four
programming problems this problem is going to be about pets we're going to make a pet store
database why don't you just give me the name of your first pet oh man i wonder what wild social
engineering hacks have been done under the guise of interviewing someone for a job because you
could extract an enormous amount of information from somebody yes just as part of a job interview
you know like tell me about this project that you are working on that like sure now you know
I know we did chat about this how I guess there was a story a few months ago where someone went
to interview at a company and it was like across the street from the competitor I can't remember
all the details they worked for a competitor went to interview and oh yeah I remember that question
it was like a health startup or something yeah and they had sold their company but it wasn't
public knowledge yet and the interviewer was trying to extract that knowledge out of them
super sketchy so that's a line you shouldn't cross yeah that's true if you're looking for lines
what are the lines you should never ever cross when interviewing your future boss
again i feel like i'm just being naive but if your normal interview process is going to make
an enemy out of someone then there are two options one your normal interview process
sucks and it's like hurting people but they just don't end up in positions of power over you so
you haven't seen it or two this isn't someone that you want to work with if they hold a grudge
because you you like pushed back and said i don't know if your solution would scale you know like
you what how dare you question my architecture diagram you peasant like i don't know i just
so you're saying if your interview process sucks there's two outcomes and both of them also suck
yeah like you suck by the transitive property of you doing this sucky interview process or they
suck yeah i don't know no one wins here yeah the the key is if you have any influence over the
outcome like if you do i think it's worth i mean they're going through an interview right like they
expect to be evaluated so if you have influence over the outcome you should evaluate them so you
have information that can be used if you have no influence then again it's i've seen the case where
sometimes management candidates will interview with the team and it's just as much about letting
them get to know the team yeah as it is about the team giving really in-depth feedback about them
yeah sort of like a preview of here's who you might work with and kind of here's here's how
they approach life yeah for sure but i don't know if you can find that information out like if you
can figure out what what they want out of you from this this round of interviews that might help you
decide how to approach it it might but i would say that there's there's basically no special
lines here that I would consider when interviewing my future boss, unless I am concerned that this
future boss is going to have some real behavioral problems. In which case, an interview is probably
the scenario under which they're going to be on their best behavior. And some people might consider
part of their best behavior to be open and honest about things that wouldn't necessarily make them
look bad. So I would take this opportunity to ask questions that you might have a hard time asking
after the person has been hired. For example, things like, hey, can you tell me about a time
when you protected your people
from bad senior leadership decisions.
Or tell me how many people you've fired
and how did they go?
Yeah, stuff like that.
You might get some pretty honest,
interesting answers in an interview context
that you might not get after this person is your boss
and is subject to the pressures
and incentives of being your boss.
Hmm, so it's an opportunity.
Or they could just lie to you
to tell the best possible story to get hired.
Yeah, I always do everything it takes
to protect my team from the pressures of senior leadership.
Right. And then they go and interview with the senior leadership.
Yeah.
And it's like, I will crush anyone that stands between this company's success.
You see all these skulls? These are all the people that defied me against senior leadership.
Oh, man.
You just got to be in both interviews.
Hey, can I just spectate in the senior leadership interviews?
that would actually be really interesting because you would see if they are yeah they're kind of
being two-faced about stuff now we're talking now that's a good idea that's a line you should
yes sneak in well i'm not even going to ask you dave i think this question has been answered right
wait you just asked i said i wasn't going to ask you you know we both make mistakes sometimes
i ask for you to forgive me for them you were forgiven shall i read our next question
please okay this comes from an anonymous listener who says our company was purchased by a private
equity firm this year layoffs began immediately while the company was gradually carved up
leadership continually violated every promise made this week during the most recent round of layoffs
i lost my job i worked my butt off for years trying to contribute as much as i could to make
a positive impact for both users and co-workers alas despite all of my efforts i was proven
expendable it feels like there was little point in doing as much as i did for this company
especially during the panicked response to covid how do i find and sustain a sense of security at
my next company how do i ensure that i can safely care about the company the work done and the
people helping to do it finding that precarious balance between being invaluable and burning
myself out oh this sucks i'm really sorry this sounds like a really awful situation to go through
purchased by private equity carved up bad stuff started happening i mean that's sort of the
the playbook i guess to be the victim of a private equity acquisition i don't really ever expect that
to go really well but it still doesn't doesn't make it better when it happens to you yeah
especially if you got carved up oof yeah that's painful yeah so i think i empathize a lot with
the question asker because one of the attributes i bring to my job is is that i care a lot and i
use caring to make up for a lot of other weaknesses of like brain power and like knowledge and you
know all those other things that are important for work but caring a lot has a downside because
the company doesn't care about you you know and and you saw this very clearly in this layoff like
they said hey thanks you know all that extra effort and positive impact hey thanks see ya i
don't know i think you're giving them a little too much credit i i kind of doubt the company
acknowledged it or said thanks yeah that's true there was probably a form email that had the word
thank you in it that sounds too humane it was probably like gratitude offerings or something
i don't know i don't know how you'd like bureaucratize saying thank you but i'm sure
they could find it out your contributions are appreciated yeah exactly your contributions
are acknowledged acknowledged that's that's so much better noted in the correct forms
yes filed away your contributions are appropriately acknowledged
yeah so there there is this tension because i i've tried to make myself not care about jobs
before and i just get unhappy and the tension is you can care a lot about a job and then it can
just disappear one day. It's not a recipe for enduring employment necessarily. I think I've
become a little more cynical about this. It's not that I don't care anymore. It's that I care a lot
about team and people and not necessarily about the company or the employment itself. Does that
make sense? I want to build great stuff with my team. I want my team to be successful. I want to
make the environment better, but I'm under no illusions that the company wouldn't eliminate
my job if it felt like it was in the best interest of the company. And early on in my career, I felt
like I had callings. I was passionate to work in this problem space for this company. And now I
have employment, which is more stable, I think, and less focused on emotion and identifying with
the company. There's also this weird thing where you see a lot of people talking about passion and
calling when they stand to profit financially from you being willing to take less money and
shoulder more risk like vcs are really big into passionate employees and like founders are really
pumped about people who are passionate about the problem domain and thus will work at their startup
for less money than a competing job offer like yes yeah i think i've become a little cynical about
passion and people trying to sell that so i'll i'll be pumped about improving things and making
good stuff but not about like i don't know how to say it not about other things i don't know
what the negative is though yeah other things huh yeah at least you're specific about it
there yeah there are two sets one is the set of people and teams and the other is the set
of everything except people and teams i guess okay that's great i gotta say it's very easy
to feel disillusioned when this happens and I don't say that from personal experience because
I have not had the misfortune of going through this kind of situation but I've been close to
people who have and in these moments you might think everything I invested in this company
was for naught but really the effort you invested in the relationships with your co-workers
will outlast any company or private equity firm and so I would be hesitant to discount
all the work you put in to improve the lives of your co-workers whether that was through
building stuff or just being there for them building relationships with them like these are
good lasting permanent things and they will outlast any company's financial forecast it sort
of feels like the question asker is saying i i put all of myself into this job and then the job
ended yep and how can i put myself through this again because this is really painful like yeah
i'm just gonna go work at another job and and that'll end someday and yep yep i gotta say
this if there's one thing this covet 19 pandemic has caused me to realize about myself is that i
and many people i know have this kind of addiction to certainty like we have this idea that the
world's going to go a certain way if we do certain things and then it doesn't right and and then that
we like have to we have to mourn or grieve that that loss of the way we thought things were going
to go and then we kind of have to reset our expectations i feel like this is okay i'm going
to wax a little philosophical so forgive me but i feel like kids who are growing up in this time
will probably be less addicted to certainty than us old fuddy-duddies are.
I'm stroking. Hang on. Let me see if I can pick this up on the microphone.
This is me stroking my beard. Can you hear it?
Oh, yes.
Okay. That's good sound work.
Interesting. So you're saying kind of implicitly, there's this assumption that I worked really hard.
I was very passionate about my job so it would stick around forever or I would be able to leave
on my terms yeah yeah but instead you had to leave on someone else's terms yeah yeah like I think
like you Jameson I have become a little bit more cynical in my old age but it's I what I have done
is I've kind of channeled that cynicism to calibrating my expectations for what a working
relationship with a company actually is when I was younger I think I used to really fluff that up
and be like you know i i am this company's employee instead of i currently sell my time
to this company in exchange for money yeah you're putting in labor in exchange for compensation but
both of those are actually bad right like identifying as an employee of the company
as like your core existence is bad but also being so detached from your work that all you're doing
is just like, hey, when I go turn this crank, dollar bills come out, so I'll just turn this
crank. These are both bad. They're just different ends of the spectrum. So how do you make sure you
are engaged enough, but not too engaged? Or I don't know, bought in enough, but not too bought
in? You need to start a private equity firm and be on the other end of this transaction next time.
Ah, you can be all in on your own private equity firm. Is that what you're saying?
Yes. Passionate about your private equity firm.
That's right. I am so passionate about this because all the money I make is on the backs of people that we lay off and carve up.
My calling in life is to find struggling companies, acquire them, slice them up, put the people in these companies into this machine that grinds them up and spits out money.
And boy, am I passionate about it.
I turn this crank with pride.
as long as we're as long as we're just completely jaded now let's just point out that probably a
bunch of people above you on the org chart made a ton of money on your misfortune yeah we didn't
even talk about that you're feeling really bad right now but there are some people that made
retirement money on this deal undoubtedly they made retirement money for lots of people
yes yeah while the company was gradually carved up leadership continually violated every promise
made i don't have any any insight into what went on at that level it's possible that they were
promising things that they thought would happen and turned out not to happen when they didn't
have control anymore and it went to this other company it's possible that they were kind of just
promising to try and keep people around and were being very cynical about it it's possible that
the private equity company told them stuff and then just changed their mind too so i think there's
a lot of possibilities and some of them are like yeah they were just totally lying to you and are
scummy that's pretty likely well i mean i don't yeah like i said i have no insight in into this
maybe maybe they hadn't been through a private equity thing before and i don't know and had
never ever read anything about any private equity takeover yeah so the question is like how do i go
on to a next job and i think weirdly the answer to it is is based off this experience that happened
to you like you have learned a lot of valuable information from this yeah you've learned a lot
about like that employer employee relationship you've you've learned nuances about it or or
different sides of it that you maybe didn't see before when you were happily employed
and everything was going great like you you've seen how it could end and your i don't know your
universe of possibilities is a lot larger now so i don't think you have to be like jaded and and
just say i'll never ever give any of myself to a job again you can just know a thing that might
happen is you give all of yourself to a company and then you get laid off and and like going into
it knowing that that might happen i think would protect you quite a bit from being as hurt by it
next time like if i had been i talked about that little startup that i worked at in the last
question if i had been laid off or fired from that job it would have destroyed me oh man i would have
yeah i mean i would feel really bad if i got laid off or fired right now but i identified so much
with like like you said i am an employee of this company and that was part of my identity
all my friends work there like it was deeply ingrained into me and just over time and working
at more places and i feel like i've developed a healthier balance of of being able to care and do
great work and commit to stuff and also having a little bit of armor in case things go wrong
yeah i like that i like that so you're saying don't turn into a completely heartless soulless
employee but also keep your guard up for when sometimes these things might happen again i like
that yeah you just know what might happen now this this could happen now can i just say also
i have a friend who has been through this times 10 at so many different companies and the stories
he tells they are just so funny now to him and to everyone else and i'm just thinking how would
he react to this story and i know that if he were listening to this story he would carefully listen
and he would put his hand on your shoulder and just say oh young one because he has been through
so much i mean i listened to the stories about startups he joined with promises of making so
much money and your shares are worth x dollars but then secretly these deals go on that dilute
the share value by like 98 you know so everything you thought you had is worth almost nothing over
and over and over he tells these stories and i'm just so glad to know them because it reminds me
that your work life comes with no guarantees of satisfaction and payout like you might want and
also other people have had it really really rough compared to you i'm not saying the situation isn't
hard because it is hard but it's great to have that friend who can give you first person perspective
on things that they've gone through and then you can look at them and say oh they made it through
and they're doing okay and they're happy and they are still employed and they managed to make it
work something you said reminded me of a topic we've talked about in the past which is figuring
out how to take things of lasting value from employment. Not take as in steal, but you're
going to do a bunch of work. You will get money in return for that. You also get experience and
knowledge and exposure to different ideas. And I think if you assume, hey, I'm not going to work
here forever. What can I learn or take away from this job that will help me in future jobs or
future, I don't know, maybe positions at the same company or something like shipping the product
will be cool. But 10 years later, after you don't work there anymore, having shipped that product
in and of itself will not benefit you in any way but if you if you can learn like here's how i can
help a team ship a product or here are these broad classes of problems to be aware of when when
something launches live or i don't know just just something that you get out of it besides like
their database transactions run 0.2 seconds faster now yeah and like i don't work there anymore so
that does nothing for me yeah i think that's also helped me a little bit as well where i i am both
working for the company to provide them value but also i'm trying to build myself up and and figure
out what durable knowledge and skills i can i can gain yeah i like that and on the topic of
durability relationships with people are durable they do outlast company tenure and some of the
most meaningful relationships i've had are ones that were formed at companies that i nor they
no longer work for you know and it's fine and it's great and these are meaningful valuable parts of
my life. So I would say never hesitate from investing in those relationships because they
will pay dividends. Yeah, that's a great point. Well, have we answered the question? Oh, I got
one more thing. I think this kind of experience will make you never feel bad again for asking
for more money from an employer. So do it. Is that what you're saying? Yeah. Like, don't feel
bad. Ask for that raise. I mean, remember, this employer will terminate your employment relationship
overnight if it benefits them so why not get more out of it while you can it's fine no problem i'd
go a step further ask companies you used to work for to pay you money now hey you didn't pay me
enough back then can i just have some of that now ask this company that laid you off if that you
could just have more severance yeah oh yeah actually yes yeah i want more severance i have
no idea if that's a thing that would work or is possible probably they will say no but yeah i like
the spirit of your point of like yeah i mean it's at the end it is sort of a transactional
relationship and you have some power in that relationship too don't be afraid of offending
them because they sure aren't afraid of offending you by laying you off yeah and you know i'm very
hesitant to ever say something like hey it's going to be okay to someone who's going through
they're in the thick of going through a really hard time like this but in my life when i've
gone through what i thought were tragedies i can always look back and say you know what it was okay
i'm okay and one day you will be able to heal from this difficult situation and you'll look back and
say you know what i am better now i have a healthier relationship balance with my employer
today thanks to that event and you may never go through something like this again and that's fine
and great but i think you will benefit from it nevertheless yeah this is really fresh like it's
I think it's pretty normal for it to hurt if it just happened and it's hurt for a while too.
I've seen some studies showing that getting fired or laid off is one of the most stressful
experiences that can happen to people. It's kind of up there with divorce in terms of like effect
on your happiness in life. So this doesn't make it feel better, but it is, it's, yeah,
it's a painful thing. So it makes sense that there's pain associated with it, but it doesn't
have to be associated with it forever. That's right. All right. Have we answered the question
now I have and if it would make you feel better one of the things you can do like as kind of a
vengeance play if you want to feel like you've laid someone off you can just unsubscribe from
our podcast and just lay us off from your phone just like the kid who gets bullied at school and
then goes home and pulls legs off of ants or something yes exactly think about how good that
kid feels yeah think of the catharsis yeah think yeah think about how much better his life gets
because he does that think about how that gives him the tools to really deal with the bullies at
school by pulling their legs off well you can pull our legs off anytime by clicking that unsubscribe
button and you're welcome to do that we won't even get mad because we won't even know but everyone
else don't you dare yeah just yeah that's just for you find more people to subscribe to make up
for this listener because we're willing to help them with their pain but like our numbers still
have to go up at the end of the day so that's right
all right jameson what can people do if they want to ask their own question they can ask a question
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