
Ask HN: How to deal with a hard to work with Start-up CEO? - astartupemp
The problem - Anger management, blames people for things when they go wrong. Unreasonable work expectations for product features and expectations that a person would be available anytime&#x2F;any day weekends including to do work and support. Does not pay properly or on time. Does not communicate properly on what is happening at the high level. In short, someone for whom you will find it hard to work for even if you like the problem the company is trying to solve and doing your best for its success.<p>Potential solution - Quit. But this would burn a lot of fingers&#x2F;relationships and put the company in a spot since I&#x27;m pretty sure most things will break if I leave. There are no processes in place for anything. I manage a lot of things and am overworked with little time for anything else.<p>Been a few years, the start-up still is in the product development phase and there have been good results for whatever has been in the market. Product market fit is yet to be achieved but I believe is possible if people continue working nicely. But with tensions running high, I wonder if that would work out.
======
OliverJones
It's hard, but important, to tease out the personality issues from the
business issues in a situation like this. The personality stuff is a pain in
the neck, but the business stuff is very serious in this case.

Anger management: definitely a personality issue. The guy is probably under a
lot of pressure and doesn't know how to deal with it, so he lashes out. If you
could continue to put up with it, you could probably stay and succeed.

Does not pay on time: definitely a business issue. This is a sign that this
guy will have to be replaced if the company's product gets to market and
succeeds. There's no way this guy will be able to manage a business growth
phase, where meeting commitments to all stakeholders (customers, suppliers,
employees, shareholders) is vital. If he has enough power to prevent his own
replacement, this company is doomed. If he doesn't the company may be doomed
anyway, because investor-appointed CEO quality is unpredictable.

Keep in mind what Gen. Charles de Gaulle said. "Graveyards are full of
indispensible men." Your departure won't trash this company.

You've given it four good years. You've (hopefully) learned a lot. You've done
what you can to make the company successful. If you have options on the usual
plan, they have probably vested. You can, with honor, move on to your next
opportunity.

You'll go through a period of mourning when you separate from these people.
You probably know the phases: denial, negotiation, anger, sadness and finally
acceptance. It's unpleasant but perfectly normal. Good luck.

------
thrill
You do _not_ owe the "company" pain without gain. I just left a similar
position with a CEO who exhibited similar attitudes about people management. I
was the 4th hire into that position in as many years - I believed it was a
technical and process issue they suffered under and took the position in spite
of this knowledge. It's generally not - it's a management and attitude issue,
and if the board cannot take the time to determine that, with supposedly far
more access to the "big picture" than anyone else, then you should feel no
guilt for removing yourself from the situation.

------
wdewind
To sum up:

-Your boss is emotionally aggressive, unreasonable and difficult to work with

-Basic functions of the company like payroll are not being handled properly

-The company is a few years old and has yet to achieve product market fit

-The company is a few years old and still in a position where one employee leaving will severely damage the standing of the company

One of these things, maybe, is possible to deal with (with the exception of
the second one - missed payroll is completely unacceptable). All of them are
absolutely not. This isn't even a question: you're wasting your time and it
sounds like tolerating a lot of misery for no reason. Companies can't succeed
like this.

------
bjt
> Does not pay properly or on time.

That means quit. If the CEO is willing to be that damaging to employees'
personal lives, it will probably never be a nice place to work.

~~~
codingdave
I fully agree. You must be compensated. It does not have to be cash. Equity
works, too. But he(?) needs to be sticking to whatever compensation agreement
is in place. That is a deal-breaker.

Many of the other issues are going to be a case-by-case basis. Does he know he
is being unreasonable? Can you call him on it, and will the behavior change?
Does he apologize and correct himself when called on it, or does he defend his
actions?

In some ways, there is an analogy between working with the CEO of a startup
and a marriage. There will be problems. There will be bad times. The question
is whether or not both sides are committed to the relationship, willing to
hear the other's side, empathize with it, and make the changes necessary to
improve it. In most cases, this is just a job, the answer will be "No" and you
should quit.

~~~
astartupemp
Not open to negative feedback. Any conversation about this is going to blow
up. Some people have tried and failed. Some have quit.

~~~
justabystander
I detailed a bit more in my other rant, but if you want to stay or get what
you're owed, you're going to have to risk the conflict.

The only way to not have conflict about this is to leave and say nothing. If
you think he won't allow you to leave at all without conflict, then you might
as well choose the conflict with the better possible rewards.

You shouldn't let things continue. But whether or not you're going to attempt
to point out the problem is up to you.

------
analog31
_Potential solution - Quit. But this would burn a lot of fingers
/relationships and put the company in a spot since I'm pretty sure most things
will break if I leave. There are no processes in place for anything. I manage
a lot of things and am overworked with little time for anything else._

First of all, people tend to over-estimate the uniqueness of their knowledge /
expertise. The company can recover from losing a key employee, if they have
any chance at all of succeeding.

Second, your contributions may have emotional value to you, but no real
economic value, if the CEO is an insurmountable obstacle to the success of the
business. So you're not really depriving them of anything if you walk.

------
julius
Quit. No second chances, no trial periods to see if the person will change. I
know it is hard, you have invested some good years already. But how many more
years do you want to live like this?

If you do not want to burn the brigde, you can offer them to work for a fixed
period of time (eg. 3 months) and with a lot less commitment (like 3-4 days a
week) on making all the things ready for some replacement to take over.

------
dantiberian
> But this would burn a lot of fingers/relationships and put the company in a
> spot since I'm pretty sure most things will break if I leave.

I've seen friends in a similar situation say the same thing. It's important to
remember that it's not your job to manage succession planning or handling
disaster recovery (unless it is). You can warn them about issues and provide
suggestions, but if they don't schedule that work for you or give you time to
do it, then you're released from that obligation IMO.

------
Kinnard
Can you provide more information? Is the CEO technical? What is your job? How
long have you been working at the company? How long have you known the CEO?
Are you friends?

"Does not pay properly or on time." Have you spoken to the CFO about this? Are
the company's finances opaque? The company has raised?

"There are no processes in place for anything. I manage a lot of things and am
overworked with little time for anything else." This is pretty characteristic
of startups: (work/workers > 1). Building a startup is like jumping off a
cliff and putting a airplane together before you hit the ground, so you have
to build the processes as you build the product and the team. Forget
difficult, it's nearly impossible which is why most startups fail.

A startup requires that you pour your life into it. If you don't want to be
working on it all the time then you shouldn't be working at that startup. If
you are seeking work life balance then you shouldn't be working at a startup.
Don't confuse a startup with an early-stage or young company. These can
provide you with preexisting processes and work-life balance. Believe it or
not there are people who still call facebook a 'startup'. Is coinbase a
startup? No, not anymore. Startups are about love. Could you imagine telling
your wife/husband, 'I love you and I'm committed to you, but I need to be able
to see other girls/guys on the weekend.' That being said, it's critical to
recharge and recreate strategically. Ever have a company field trip or
retreat? Consider implementing a startup shabbat:
[https://www.youtube.com/watch?v=oRdMUhBPRjY](https://www.youtube.com/watch?v=oRdMUhBPRjY)

Much more data is necessary to provide a good answer.

~~~
astartupemp
The CEO is less technical and more business. I run software engineering. First
employee. Company is 4 years old, I have been working here for 4 years. Known
CEO for about the same time. I don't think we are friends since I basically
avoid talking unless needed for work. Companies finances are okay. The product
market fit is not all there yet. But there is a path to revenue. The Series A
raised a few months ago is good enough to cover all costs and more for more
than a year. There is no CFO, the CEO manages the finances. I have build a lot
of the processes and I'm well aware of how start-ups work. We (2 founders +
me) started working out of a coffee shop and now have about 20-25 full time
people.

~~~
pavlov
What does the other founder do? Is [s]he aware that you're considering
leaving?

Sounds like that person stands to lose a lot if you go. Maybe you should be
talking with him or her.

~~~
astartupemp
Other founder is the CTO. I hope to do this sometime. Not so good at talking.

------
striking
Quit.

"What matters is not ideas, but the people who have them. Good people can fix
bad ideas, but good ideas can't save bad people." \--Paul Graham

------
g8gggu89
Is the CEO working these same crazy hours? Does the CEO get paid properly and
on time? Are you getting paid a reasonable amount, really? Where's the funding
coming from and why don't they hire another engineer when they clearly seem to
need to?

Are you giving the CEO realistic expectations of when things will get done,
including time for prerequisite things?

At a bare minimum, I would keep my resume updated and see if you can find a
better offer.

~~~
astartupemp
I don't know how to measure work that is mostly email and meetings. Some deals
have been struck that sound awesome in theory but executing them is a
challenge for me in the present scenario. I don't (yet) care about money. I
spend a lot on office expenses too and there is again no process for that
either and I rarely get paid for those. I'm generally realistic with
expectations and deliver on time but I believe there is plenty of accrued
technical debt by now that I'm not sure I can manage well going in the future.

~~~
g8gggu89
> I don't (yet) care about money.

Will you be happy if the startup goes under and they've been paid and you
haven't?

~~~
astartupemp
At this point I have no other expectations than hoping the product scales as
has been envisioned and solves the problem at a meaningful scale to justify
the 4 years I have put in. I'll figure out the money part somehow or just go
broke and get another job.

~~~
greenyoda
You've already justified the four years you put in by doing much more than
your share of the work to keep the company going this long. Nobody can fault
an employee for leaving an abusive employer to pursue better opportunities.

Take a step back and realize that your self-worth is not based on the success
of this company's product and this company is not your life or your family.
With your skills and the experience you've gained from this job, you'll find a
new job at a better-run company that will have a better chance of releasing a
successful product.

Also, if you quit and they don't pay you every cent you've earned within the
number of days required by law, you can file a wage-theft claim with your
state's labor department - they're very serious about employers ripping off
their employees and will file criminal charges if necessary. There's
absolutely no reason why you should go broke because of this company's
mismanagement.

------
laurentoget
There are three possibilities: 1- you really are a key asset to the company
and the founders realize it, then they will work with you to keep you on board
2- you really are a key asset but they have no clue, and you will never be
rewarded so you should probably cut your loss and leave 3- they do not really
need you and if you are not happy there you have no reason to stay.

the only alternative in which you should remain there is (1) and you can only
figure out where you stand by making it clear you will quit if things do not
change.

TL;DR

learn to say No

------
6d0debc071
> Quit. But this would burn a lot of fingers/relationships and put the company
> in a spot since I'm pretty sure most things will break if I leave.

Well, that may or may not be true. But even if it is, so what? It's not your
company.

You have given them work, they are supposed to have given you money. And you
have both agreed that that is a fair compensation for your work, at least for
as long as you are doing that work for that compensation. And that settles
accounts; you're back to a position where you don't owe them any more work and
they don't owe you any more money. There's no obligation in that for you to
continue to work for them. You don't owe them any loyalty – that's not the
sort of thing you can buy. (Phrased another way 'money is a bad retention
tool.')

There are things where it makes sense to have a degree of personal loyalty to
_some_ of the people you work with in a company (though having a loyalty to
the company as a whole is of course nonsense.) There are people who we might
choose to continue working for, despite the fact that we might make more money
elsewhere, because those people are good at what they do, take care of us, and
we generally enjoy working with them. But it doesn't sound like that's the
case here.

------
ypcx
You are in an abusive relationship with a sinking ship, and you should leave
as fast and as cleanly as you can.

Even if you somehow manage to teeth it through and see the startup succeed,
you will eventually be thrown away as an unhappy and unenthusiastic employee
and be given a bad review, no matter what your achievements or sacrifices
were.

More likely, due to the pressure, you will just burn out, start doing mistakes
and avoiding work, getting yourself fired with a bad rep.

~~~
greenyoda
_" you will eventually be thrown away as an unhappy and unenthusiastic
employee and be given a bad review, no matter what your achievements or
sacrifices were."_

This is a very important point. The company's founders have absolutely no
loyalty to him - they'd throw him out like trash (without the slightest
regrets) as soon as it becomes convenient for them. Thus, he should not have
any more loyalty to them than they have to him, and should not feel guilty
about leaving to pursue better opportunities.

------
kzhahou
You have a shitty CEO. Sounds like he or she can't manage internally. Do you
really think this person can actually lead the company to success? It's hard
enough to succeed when you have everything in your favor, let alone when the
person at the helm is not good at their job.

If the person at top is not good, what are the people learning at the next
level down, and the levels below? Not much. Not how to _be great_. At best,
they're learning how to "manage up" and deal with BS from the boss. Your
leaders must be best in class. Not the best at _everything_ , but the best
people inside the company for their job functions.

You may not have the CEO title, but you are skilled and capable, and deserve
better. Remember also that if the company succeeds, the CEO will reap the
greatest rewards, by orders of magnitude. Should you continue to suffer for
that outcome?

Also, pro-tip: when you leave, the company will not fall apart. It never does.
People leave all the time. There's a _very good chance_ that others are
thinking of leaving (and interviewing as we speak) including the CTO. Oh, how
many times I've left a job, to find out my manager left the week after me.

------
greattypo
"Been a few years, the start-up still is in the product development phase..
Product market fit is yet to be achieved"

Move on!

~~~
ScottBurson
Yeah, this is a huge red flag. Getting product-market fit shouldn't take
_years_.

There are plenty of fun, non-abusive work situations out there. Find something
that's already starting to grow and that has a happy vibe.

------
johnkchow
I've been in a very similar situation before (one of the first engineer hires
in a company that grew to about 15 people when I left). It's great that you're
loyal and conscientious (you won't have any problems finding a job).

The first thing you need to do is sit down with your CEO and have an honest
conversation about how you feel. Come prepared with an outline of all your
grievances and be very specific about what changes that you need to see to be
made. __This includes compensation and hours __. These days early stage
startups are offering super competitive salaries, and it 's more than fair to
ask.

Having this conversation gives him a chance to do you and your coworkers
right. Best case scenario: he totally empathizes and has a change in heart,
and the company as a whole benefits.

But you have to be prepared for the worst (which will probably happen): not
only will he offended by your honesty, he'll come out attacking your
character. These kinds of CEO are just emotionally clueless, and nothing you
say or do will change their minds. In this situation, you must be fully
prepared to walk away from this company. By staying you'll be enabling his
behavior and you have nobody to blame but yourself for being in a hostile
environment. By leaving, you not only will find a better opportunity (and you
will), you hopefully will give the CEO a wake up call.

When I put in my 2 weeks notice, I got blasted and put my founders and fellow
engineers in a tough spot. But a lot of good came out of me leaving.
Immediately after my 2 weeks notice, the CEO pulled everyone aside and gave
everyone raises which were near market rates. The founders also became more
aware of how employees felt. A few other coworkers who were as miserable as I
was eventually left the company too, and they're all in better, happier
places.

There will be some people who will see you as leaving people behind and making
things tougher for them. Over time those individuals will come around and see
that whatever decision you made, you made it for the right reasons. The most
important thing to keep in mind while you go through this: your top priority
is your physical, mental, and (most important) emotional health. Don't listen
to what other people say.

Good luck with all this. This will be a tough journey, but if you keep your
chin up, I guarantee that this will be the best thing that you'll ever do.

~~~
gknoy
> By staying you'll be enabling his behavior and you have nobody to blame but
> yourself for being in a hostile environment. By leaving, you not only will
> find a better opportunity (and you will), you hopefully will give the CEO a
> wake up call.

This also means that you should have a BATNA, such as an offer of a new job.
It sounds very much like the CEO's response will be to ask/force you to leave,
so make sure you're operating from a position of strength if at all possible.

------
jstoiko
> The problem - Anger management, blames people for things when they go wrong.
> Unreasonable work expectations for product features and expectations that a
> person would be available anytime/any day weekends including to do work and
> support. Does not pay properly or on time. Does not communicate properly on
> what is happening at the high level. In short, someone for whom you will
> find it hard to work for even if you like the problem the company is trying
> to solve and doing your best for its success.

Have you raised this to him/her? My two cents: raise all the points along with
one or two advices, this way she/he won't feel attacked but rather helped.

You may end up quitting if you're not satisfied with the reaction but at least
you will have tried to fix it.

------
jwatte
Is the board independent? If so, the board is the boss of the CEO. You owe it
to the board to let them know about problems with their charge. If the board
is Buddy Buddy or the company is bootstrapped, then just give two weeks notice
and start interviewing elsewhere.

~~~
astartupemp
AFAIK, there is no board yet. There are investors and advisers but I have no
way of reaching to them.

------
GFK_of_xmaspast
It sounds like the bridges are half-burnt already, and not by you. Moonwalk on
out the door and get your local Department of Labor on the phone.

------
1arity
Go out with the person on a personal basis. Get to know them ( only so that
what you will eventually say will have more impact ), and then hit them with
the following,

"Your anger and blaming doesn't work. It's actually giving away your power to
others by pretending they are responsible for what is not working with your
company. It looks more and it is more powerful if you own all of this mess,
and take responsibility for all of it. Also, the anger stuff is unnecessary,
it just makes you look frustrated and weak, because you seem to be saying you
are so dependent on these other people that their choices so greatly vex you.
Well...what kind of powerful person would do that? Look, I may not be the kind
of entrepreneur you are, nor have the same technical or social skills. And I
do know what I am talking about. Sure you can choose to believe that I'm just
some person who doesn't have a clue what they are talking about, or you can
choose to believe I know it when I see it. And believe me, I see it with you.
I see your potential, and I see how these things are in your way. I want this
company to be great, and I want you to be great. I know you are, there's just
your lack of clarity on these issues which is missing."

------
lewisjoe
Your personal life and your peace of mind is as important(or even more
important) as your willingness to solve interesting problems. Quit.

------
god_bless_texas
Have you had any honest conversations about this with the CEO yet?

I see most people saying "quit!", but really that is not fair to the business
or the other people who are there. This kind of behavior gives technical
people a bad name, and perpetuates the myth that we are social hermits who
cannot sell or run companies. You admitted that you effectively avoid the CEO,
so how would he know you've got this displeasure?

He or She deserves to know how they are fucking up. If it were me, I would
gauge the response to this conversation as my go/no-go decision maker. Could
be that they are all over the place and don't realize they have reached this
point. You may have a heart to heart and say, "look, I need these things fixed
and top of the list is your overt behavior". Any sane CEO is going to consider
your contribution, realize their behavior has degraded and quickly adjust. If
not, pack your bags, baby!

The pay and such is actually a separate issue, and _no excuses_ should be
sorted out - right now.

~~~
justabystander
> I see most people saying "quit!", but really that is not fair to the
> business or the other people who are there. This kind of behavior gives
> technical people a bad name, and perpetuates the myth that we are social
> hermits who cannot sell or run companies.

This is hardly a fair statement. A person specializing in business, marketing,
or PR would do the same thing - quit if their manager/CEO is terrible.
Moreover, they would have demanded far more out of the company and left within
2 years instead of four.

People saying "quit" are doing it because it's not really worth the hassle to
them. They're avoiding conflict. Which is quite acceptable unless he's going
to use that conflict to better his own position. He's spent four years of
dealing with this and being underpaid. He could just walk and get a better
paying job in a better environment. Standing up for himself might bring
vengeful behavior out of his boss. It would fit with his other actions.

> This kind of behavior gives technical people a bad name, and perpetuates the
> myth that we are social hermits who cannot sell or run companies.

There is absolutely nothing here that deserves you pushing a tech stereotype
or hermit narrative on it. Conflict avoidance is a well-known _human_ issue.
Hundreds of people in hundreds of fields quit because of leadership issues.

It is completely unfair to make people think that you have to allow people to
treat you poorly as part of a proper social structure. That's a hostile work
environment, and there are laws about that sort of thing for a reason. You
don't ever have to "resolve" things. Leaving is always an option.

> Unreasonable work expectations for product features and expectations that a
> person would be available anytime/any day weekends including to do work and
> support.

There's another labor violation. This CEO specializes in "business". He knows
the rules. He has no excuse for his behavior. He doesn't treat his employees
respectfully, so he's not deserving of any loyalty. And the other founder
doesn't stop it, though I'm sure he sees it, too. Management doesn't really
care.

He shouldn't have to have this conversation in the first place. Don't blame
him for not wanting to have it. There are 20+ people in that company. It's not
his job to be the messenger if he doesn't want to.

Though I'd still recommend doing it because it would teach him to recognize
and prevent these situations in the future.

------
rajacombinator
Quit, get a job at a real company. Not sure how you can go 4 years and 25
employees and no product/market fit, failing to pay people on time, and
yourself as employee #1 having no processes in place. (You're to blame for the
last one.) What are the other 22 people doing?

------
rational-future
Ask to be appointed CTO. If it goes through you'll have a lot more freedom, if
not just quit.

~~~
astartupemp
There is a CTO, co-founder and I don't think he is that much better off then I
am except for the fact the the risk/reward equation is a lot better for him.

~~~
boomzilla
This is a key point. If you three all started from a coffee shop, why are they
co-founders and you are the first employee? Even if the other two persons
worked on the company a few month before you started, after 4 years, you'd
been there (and hopefully contributed) 90% of the founders time and
contribution.

Startup life is hard, and it's a lot easier to sacrifice with significant
ownership and a sense of purposes.

~~~
astartupemp
Well I didn't come up with the idea and I waited until they could raise some
seed because I needed a salary. I did build the product from scratch, in fact
that's the only thing out in the market currently. I didn't care about titles.
And I didn't know about equity. I just joined because I wanted to solve the
problem.

------
AshFurrow
Run, don't walk, out the door.

------
fsloth
Do what feels right for _you_. Taking responsibility is a fantastic trait but
you are foremost responsible for you own health and finances. Ethically, IMO,
you are not responsible to the company beyond what it says in your contract.

------
RollAHardSix
> Does not pay properly or on time.

Say 'goodbye'. That's a sin for companies to commit.

Do you have equity? If not, you don't need to worry about the company,
especially when the CEO is providing you no support.

------
metasean
I've been there.

I've done that.

I finally quit and am so much healthier and sane for having done so!

Bullies, no matter how good their ideas, are bullies.

Bullies do not make good bosses, however they do make work environments rather
toxic.

------
jqm
All of these things, although unpleasant, can be worked with except one: "Does
not pay properly or on time."

There is no option. You owe them nothing. Quit. Immediately.

------
revelation
If you're not being paid on time, you quit, and then you report the company.
There is nothing left to discuss here.

------
gorbachev
Your sanity / well being is more important than the company. Quit.

------
g8gggu89
Will you send them my resume?

Is there something like glassdoor for startups so people can try to avoid
startups like this?

~~~
astartupemp
Well I definitely don't refer friends here. But I also do recruit people. I do
take care of the people I recruit by shielding most communication between the
new hires and the CEO. I also believe that I need to plan an exit strategy by
recruiting people that could replace me because the others cannot.

~~~
greenyoda
If you're just an employee, it's management's responsibility, not yours, to
make sure the company can survive your leaving.

You shouldn't feel guilty about quitting, since they'd fire you in a minute
without any warning if it was convenient for them.

------
paulhauggis
"Potential solution - Quit. But this would burn a lot of fingers/relationships
and put the company in a spot since I'm pretty sure most things will break if
I leave. There are no processes in place for anything. I manage a lot of
things and am overworked with little time for anything else."

You may think this, but the company will find someone to replace you. From
what you described, you should quit. Chances are, it's not going to get any
better. People (especially people in power) don't just change overnight and
will most likely try to get you fired if you go against them (I've seen it
happen too many times).

~~~
invalidfunc
This was my scenario recently - and quitting was the best thing I ever did.
They replaced me a few weeks later and the company is doing a-ok. I didn't
burn bridges and am very close friends with the people that work there

Leave professionally, don't bad-mouth anyone, and go on with your life.
Chances are you'll find a better job now you know what to look out for.

------
michaelochurch
I have been there. There are three options here:

Option A: get the fuck out.

Option B: get the fuck out.

Option C: get the fuck out.

Your boss is a jerk and doesn't pay on time. He's hiding high-level
information, which means that (a) he's planning to screw you, (b) that the
investor front is going badly and there might be nothing happening, or (c)
that he doesn't view you as an equal partner in the business. (No exclusive
"or"; probably all three are true.)

You're spending too much time and emotional energy on a business that has no
future. If it had a future, it wouldn't have existed for several years and
still be missing payroll. If you're honest with yourself, I think you'll
probably notice that what's keeping you there is the "sunk cost" fallacy. Stop
wasting more time. Count it as a learning experience and use it for personal
growth, but get out as soon as possible. (Start sending out CVs. Don't
actually quit until you have a better job.)

