
Ask HN: Best questions for an engineer to ask a CEO during a job interview? - northisup
I’m interviewing right now at a lot of startups and am looking for better ways to ask “so, where is this thing headed?”<p>What do you always make sure to ask?
======
notjustanymike
What are the problems you are personally trying to solve?

How do you like to make decisions?

What do you believe is the purpose of a manager?

What do you believe motivates employees at your company?

From an employees perspective, what makes your company a unique place to work?

How do you recognize major achievements?

... basically I like to dig into culture (which is always top down), and
empathy. I want to know whether the CEO considers employees people or a
resource.

~~~
jl2718
These are important culture questions, but you will never get the truth from
them. Everybody knows what you want to hear. If you ask a harder question,
they will dislike you. Maybe the only real way to get at this is to ask about
specific standards and procedures that define the culture.

If you want to get right to it, culture is 99% defined by “who” is given power
over hiring, firing, and promotion.

If it’s your manager, you will be his personal assistant. If it’s your peers,
you will be playing Survivor. If it’s a board, you will be fighting for a spot
on the most glamorous projects.

~~~
notjustanymike
I disagree with your points, and think there is no need to act so jaded.

When asking these questions, you will sometimes get honest answers and
sometimes get the pre-canned responses. How people choose to answer questions
tells you a lot about the kind of person you're dealing with. I value the
answers not just for their content, but also how the person chooses to
interact with me.

If a CEO only flatters me with sugary answers then he's likely lying to my
face, which is a trait I dislike in leaders. Unfortunately, this behavior will
trickle down to managers and peers (with occasional short lived exceptions).
If he's honest about the issues they face then I can likely expect the same
from others.

Culture in a company extends far beyond hiring, firing, and promotion. Those
are unique events that combined happen a couple days a year in a smaller
company. Day to day culture is far more significant, and focuses on how we are
expected treat each other. Honesty, acknowledgement of problems, and
transparency are the things to look for.

~~~
spectramax
I disagree. You’re most likely going to get a “CEO answer”.

The problem with asking these questions is - what is the criteria for a good
vs bad response? What are red flags?

These questions sound super handwavy and can be answered easily by polished
talk. They’re useless mostly.

Instead ask specific questions that can reveal deeper issues. If you’re asking
about time, then ask - how many months until X? If they waggle around then
follow up again - specifically, how many months or quarters do you think it’s
going to take to do X?

~~~
notjustanymike
True, hard numbers get solid answers. But then what? Are you any closer to
knowing what your day will be like? You can get those numbers from other
people in the chain. This is your short chance to understand how the head of
the company thinks; don't waste it on information you can get elsewhere.

------
HillRat
Sales. Always ask about sales. Specifically, what’s the sales culture — who’s
responsible, what’s the acquisition model, how well do the sales folks
understand the offering, how do they manage the funnel, and so on. At the end
of the day, unless you’re talking to speculative R&D-driven startups whose
future success will be driven by technical breakthroughs, everything comes
down to how effective the sales org is, how well it meshes with the company’s
aims and mission, and how well they will work with the other groups. An
immature or poorly-structured sales org will kill the best technology in the
market, and ruin your enjoyment of a job.

If you can, see if they’ll run you through a client pitch, give you a chance
to poke some holes in their approach. Get a feel for how much they care about
solving customer problems, their ethics in client capture, what they’re
promising the market, and how you feel about them as people. Tells you a lot
about a company.

~~~
jbduler
Spot on HillRat. You nailed it.

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hluska
“Let’s say that I want to spend $5 a month on a SAAS that will save me x hours
a month. What process do I have to go through? What if the SAAS is $25 a
month? Or $150?”

Of all the questions I’ve ever asked, I consistently learn the most from this
one.

~~~
lesss365
Sorry if it isn't obvious and I come off as clueless for asking, but is this
to gauge bureaucracy?

~~~
b_t_s
This is a great question. It can show a lot of things, overlay bureaucratic
process, control freak, lack of trust/understanding of devs, general
disorganization, penny wise pound foolish mentality, not invented here
syndrome. Or it can show that the company values devs, trusts them, and wants
to retain them.

------
shanehoban
Revenue rate - Does the company take any money in, or is it simply running off
funding

Runway length - Similar to above, trying to gauge if the company is self
propelled or not

If received funding, how much and when was it received, also ask for burn rate
here.

Very quick estimate of company health = Revenue per month - (burn rate per
month + (head count * average monthly salary)).

~~~
floatrock
These are investor questions, not employee questions. In my experience, you're
either going to get a vague dodge or a flat-out "we're not going to share that
/ it's confidential" response unless you're applying for a C-level position.

A better approach is to dive into the product and make a judgement... "What
does the company need to do to secure its next round of funding?" VC-scale
rule-of-thumb is you need a new funding round every 18 months... 12 months to
improve the metrics, then 6 to close the next round. Figure out when the last
one was, when the next one comes due, and how honest the company goals are
from now until then.

~~~
xemdetia
I think I have asked these kinds of questions in every one of the interviews
I've ever done to whoever was the senior manager/C and they haven't even
blinked at answering the question. It is critically important to me to know if
the business feels healthy as it directly affects my confidence in the
company, the vision that the person across the table is trying to sell me, and
if the person in front of me has their head screwed on right. This is the kind
of information that I use in combination with external signals to call
bullshit or not. To also colour in this perspective a bit a frank 'I don't
know, we are too small and we are struggling to get our internal operations on
track and are looking for people who can help' is a sane and reasonable
answer.

If I join the organization without asking these sorts of questions and realize
that the person leading the company doesn't even know how their own company is
running that kills my morale. It could also be that when I ask these sorts of
questions I am frank about my opinions: I don't mind being part of the machine
but I am business oriented and derive motivation/happiness from doing what I
can to accelerate that business even further.

------
josephwegner
These are the questions (and reasons for them) that I have used in the past:
[https://joewegner.com/blog/startup-interview-
questions](https://joewegner.com/blog/startup-interview-questions)

~~~
jacklewis
Can you please clarify why you say "equity is worth at most $0"? If the
company is successful surely the equity is worth something.

~~~
raptorraver
Equity isn’t money, it’s a lottery ticket.

~~~
maximilianroos
Lottery tickets are worth more than $0

~~~
emilecantin
Yes, but not much more. E.g: I can go right now get a ticket for a $50M prize
for 5$.

How much do you pay for equity (in the form of reduced salary), and what's the
expected upside?

~~~
learnstats2
And I would value that lottery ticket at about $1 today - with the
understanding that: a) the face value is over-stated by around 100%, and b) I
have no hope of riding out the variance, so the gamble is a poor one for me.

------
Avalaxy
The arrogance of many of the questions posted here surprises me. I am not
unwilling to give answer to all sorts of questions that aren't the employee's
business, but for some questions posted here the tone is so hostile and
assuming that there is ill-will that I would probably not hire those people
based on arrogance. The fact that software engineers are in a good position
market-wise, doesn't mean you can say whatever you like to someone.

~~~
cheesymuffin
Some of us have enough money that we just don't care. If you want people to
tiptoe around your feelings I suggest messaging some broke new grads.

~~~
Avalaxy
Why are you even applying to work for someone else's company then if you're so
super rich? If you're gonna be arrogant you can expect many companies to shut
the door for you.

~~~
baoha
I can see you're not from a hot job market for software engineer.

Here (Bay Area) people usually don't apply for jobs, specially jobs at
startups, unless they're really into the products/team/tech/... Even old-
school walking-dead companies like Cisco/IBM/HPE pay way better than most
startups in term of cash compensation. And given the high risk of failure,
startup should sell itself hard to attract talents.

I also found those questions are normal, far from being arrogant.

~~~
Avalaxy
I must say that I am indeed not in the SV bubble. I come from a CS background
and I now find myself in a position where I'm hiring people for my own
company. This means I totally understand both sides. I'm mostly recruiting in
the Amsterdam area though, and software engineers are not seen as rockstars
here so it's a big cultural difference.

~~~
krageon
In the Amsterdam area the done thing is to treat software engineers as
disposable trash, unworthy of a proper salary. This is an important piece of
context when considering your attitude towards them, which to me personally
doesn't speak of a large capacity for patience when it comes to the kind of
questions meant to give people peace of mind.

------
suff
What is the startup's burn rate, and how much capital is left, or more
generally 'how much more funding runway is left?'

~~~
ascendantlogic
Depending on how open they are start asking questions about their cap table
too, especially if they're offering you equity as a large part of
compensation. Getting 1-2% in options is wonderful unless they have a down
round or two on the books and those investors are going to wipe everyone out
with their ridiculous liquidation preferences regardless of how much the
liquidity event is for.

~~~
gct
Yeah I had a startup offer me 50K shares or something like that and I started
poking at what their full diluted share count is and they hemmed and hawwed.
Pass.

------
mpweiher
Oh...one fun one (not during the job interview, but during a town hall for new
hires, QA sesssion).

New employee, thinking they're really clever: What would you do different if
you had unlimited resources?

Steve Jobs: I do.

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dyeje
My goals when talking to a CEO are to get a feel for the strategic direction
of the company and culture fit. I try to ask these questions to a variety of
people at the company to evaluate how aligned everybody is, but usually the
CEO has the best insight into strategy.

To that end, I don't really have any generic questions because they vary
greatly by situation. Some examples:

Company was beginning to enter the enterprise market so I asked questions
about the direction of the sale team, their comfort with enterprise sales
cycles, etc.

Company was tightly integrated to a third party platform so I asked questions
about that relationship, wether they wanted to move that tech in house, how
they would do that, etc.

------
PopeDotNinja
"What is suboptimal about working here, the kind of stuff that someone people
will cause some people to quit & that others can accept? I am gonna find out
if I take the job."

A CEO who answers the question directly, with confidence, makes me believe
their answer, and appreciates your directness gets +1 gold star. If you ask
this question, you'd better be prepared to reply directly & with confidence,
too. When confront someone directly, you should assume they will do the same
to you. Have some good stories ready about why things that might drive someone
else bonkers are things you can accept.

------
takanori
What value does the product drive for the target stakeholder?

At what frequency is this value delivered to the stakeholder?

How does the stakeholder know they are receiving value?

How does the value compare with the price paid?

What is the product’s TAM?

What things are out of the company’s control?

If the company doesn’t have a self-serve product ask why?

What is the company’s short-term, long-term distribution strategy

Explanations here:

[https://medium.com/@therealpankaj/interview-questions-to-
ask...](https://medium.com/@therealpankaj/interview-questions-to-ask-a-
startup-ceo-cf04d71752e8)

------
leothekim
Will you share slides from the last board meeting?

~~~
floatrock
Or at least "do you share board meeting slides at the following employee all-
hands"

------
arh68
What's the exit plan? To run the company privately forever? To hit IPO? To get
acquired by some megacorp (which one)? What's the timeline on these things?

I wish I'd been able to ask the CEO these things. I've had an interview
interrupted at 10am by the CEO showing up to work, walking into the (his)
conference room I was being interviewed in, no knock, drop his stuff and
leave. Yes, it was an open office, and yes, I think he had pretty much checked
out at that point.

------
planteen
Depends on the company size and how long they have been around. Based on
experience, I will always ask the following at a smaller company:

Have you ever been close to missing payroll?

Depending on the answer, make sure to find out when was the last time they
missed.

It is very stressful to work at a place that has cash flow issues. They may
very well be honest that they are on the cusp of big deals and/or funding. But
wouldn't you want to know if there are short term issues before you start?

------
tootie
What is relative prominence of technology to the company's strategy and key
decisions?

This is an important one. Even so-called tech startups are almost always
driven by business goals. Marketing, sales, financials, etc. Tech can easily
get put in the back seat and just asked to execute on business decisions they
weren't involved in making. That makes for a very unfavorable culture to
developers.

------
evilstark
"What is the one thing an engineer could do that would make a huge difference
in where we are trying to take this thing?"

This question

\-- a) gives him an opportunity to tell you exactly where we are trying to
take this thing,

\-- b) shows you what he thinks is the value of engineering talent, and

\-- c) gives you a good picture of what exactly you should be focused on if
you want to really succeed here.

Go get em!

------
yingw787
1\. Would you prefer a large number of small customers or a small number of
large customers, and why?

2\. What is your current pricing model for your product(s), and how will your
pricing models change over time?

3\. What tangible efforts have you made to make high-level business decisions
transparent across all levels of the company?

4\. (optional) Why have you chosen your particular financing model
(bootstrapping / VCs / other), and what are the pros and cons you have
considered?

You should be looking for a high to very high degree of alignment between
sales/marketing and engineering, high price points and premium markets, and a
good amount of transparency. The insurmountable problems that will make your
life miserable are the problems you cannot solve and cannot solve with
technical means (working for low pay / benefits cut / company is VC playground
and has no future / etc).

------
kthejoker2
I don't have a specific question to suggest, but I find it very helpful to
think about and clearly write down three things about any question you intend
to ask others for evaluation purposes:

1) SO WHAT - why am I asking this question? What am I trying to learn? How
will I use the answer to make my decision? 2) what are some possible answers
to this question? is there a "best"/"worst" answer - the answer I (don't) want
to hear? This can be objective or subjective, but you have to have a strong
opinion. 3) two good follow-up questions, especially if the answer is neither
extremely good nor bad.

I find that rubber duck thinking through this cuts out a lot of questions that
seem superficially okay but actually give you no useful criteria to make a
decision.

------
jl2718
If you want to get the truth from people who are accustomed to spin, ask the
opposite question:

If you want to know: “How important is meritocracy in this company?”

Ask instead: “How important is loyalty in this company?”

But let’s be honest. At this point, you’re less worried about getting the
truth than getting the offer.

So ask them how they became so wonderful.

~~~
notjustanymike
> So ask them how they became so wonderful.

Oh God, never do this. The only CEOs who respond well to saccharine flattery
are the ones you never want to work for.

------
mcavaliere
Some of this you can look up on CrunchBase beforehand, which you definitely
should do. For me I believe in trying to gauge just how prone to borrowing the
founders are; if they have a solid model and are more inclined to seek profit
rather than investment (except after proving the model, and primarily to
increase growth), then that's a good sign.

If however they seem like they approach is constantly to borrow money, that's
a red flag.

* How much runway does the company have? What will the plan be when we start to run out? * How well have you proven the business model? * What type of validation/research did the team do for product-market fit (before building the product)? * What's the management team's approach to profit vs investment?

------
jbduler
Look for signals. Pretty simple: the caliber of the CEO, CTO or the caliber
and experience of the VP Eng. Then look at the VC's funding the company, and
the names of the partners on the board. If top tier VC (say Sequoia,
Benchmark, or A16) invested in series A after having invested in seed, then
you are good. VC's can be be wrong for sure but they have done a ton of
background checks on founders, the tech, why customers would buy, etc.. There
is no way you can do as much and have as many contacts. Ignore vanity signs
such as "Fancy Advisors", they bring next to nothing. Same for "Fancy Big
Client", just a free test on some ancillary product. Good luck

~~~
akchin
In general this is good advice. However I would advice against depending too
much on VCs. They don’t really get it right a lot of the time. At the end of
the day it is the caliber of the team, the sales/customer acquisition strategy
and the competitive dynamics of the market and the position of the company
within this market. So the first part about judging the team is valid. The
answers below about asking questions about sales/acquisition is very good.
Depending on the stage of the company, you should also ask about profitability
or if there is a clear path to profitability.

Also don’t shy away from asking challenging questions...such as competitors
etc. and be wary of a CEO who is dismissive of challenges. You should get a
well thought out answer.

------
agrippanux
Ask what is the current strike price and how many shares are outstanding.

Then do simple math on the equity part of your offer and figure out if
spending the next few years of your life there is worth it. Feel free to run
analysis on 2x, 10x, 100x, etc of the strike price.

------
jressey
Tell me as specifically as possible what this company will look like when you
will have considered it a success. I don't want to follow a leader that
doesn't have a clear vision of what they're working towards.

------
balabaster
Since you came on as CEO, has your vision for the company changed or evolved?
What impact has the culture of the company had on your vision and how do you
plan to adapt the culture here to achieve your objectives? Have you had any
regrets about anything you've had to do to get the company to where it is
today and what would you do differently if you could go back and have a do
over?

I want to know more about who this person is than any of the financial details
of the company. I want to be able to believe in this leader of the company. I
need them to show me they're a leader I want to follow.

------
narag
I ask what's the biggest problem the company has around the position and
what's being tried to solve it.

How this question is answered gives information about what to focus on, also
about how they react to problems.

------
pcurve
I think that's a fair question to ask, but I would also ask something along
the line of, "specifically what kind of help do you need from this engineer in
helping your company get there".

------
jeremy_wiebe
I’d ask some form of “what separates you from your competitors?”

I’m interested in why this CEO/company thinks their solution is better?

How will they protect their advantage (or rather, how is that advantage
protected)?

------
notus
Where do you see yourself in 5 years?

------
armini
The most important question you need to ask is to yourself when you walk out
of the meeting:

1- Did I understand their purpose and mission? 2- Was the leader someone
inspirational & respectable that I'd be whiling to support during a crisis?

If you don't understand the mission and if you can't respect them then find
something that's more suitable.

------
klanghans
“Why do you think, you are the right CEO to lead this company?” And start
listening for BS-Bingo, CV flattering or the real reasons.

Why is this question so important?

Because the CEO of a company sets just-cause, cultural, visionary goals.

If he fails to bring that to the table, you job will be problematic by good
chance.

The problem always starts from the top, so find out if he’s a problem or a
solution.

------
rewddit
What keeps you up at night?

~~~
eldavido
No CEO can or will answer this. Don't even bother asking.

------
iblaine
I curated a list of 'winning' questions from this thread. Good luck and please
ignore everything in this thread.

* Does the company have contingency plans for down markets?

* what is the current strike price and how many shares are outstanding

* Will you share slides from the last board meeting?

* Why the heck are you still working?

* Have you had any regrets?

* Does the company take any money in, or is it simply running off funding?

------
djeikyb
Have you ever missed payroll? When was the last time? In my case the, answer
was “not recently, but..” and led to further discussions where it became
obvious the company had a tenuous business model and every payday was a
gamble. Literally the ceo told me this, just cause I asked.

------
jrauser
As a data scientist: What do you want to know about the thing you're building
and how it works?

~~~
whatshisface
"We don't know what we want to know, but we have a vague sense that if we knew
we would benefit from knowing it."

~~~
Avalaxy
Would this be a bad answer? I think part of the data scientist's job is to
look at the data and see what beneficial information can be gathered from it
and how it can be used to optimize the company/revenue/costs.

~~~
sidlls
It's a terrible answer. It means they don't even know enough about what they
want to have even an idea of what questions to ask. They may as well be
flipping coins or tossing crap at the wall to see what sticks.

Empirical inquiry doesn't (usually) start with aimless exploration of data
hoping it tells you something. It usually starts with an observation and some
pertinent questions.

------
prolepunk
What are the hiring practices? Is everyone salary disclosed? What is
percentage of women occupying technical positions?

This might sound controversial for some, but the answers to these three
questions would tell you pretty quickly what kind of company this is.

------
suff
Have you made any ship date commitments to the board, or to stakeholders, or
customers?

------
andy_ppp
I always ask what is the best and worst part of your job to the
interviewer(s). I am actually interested in discussing that though so it might
go terribly if you don't actually want to understand more about what they do.

------
throwaway45765
Now that you’ve been acquired, how invested are you in the company’s future?

------
monksy
1\. Does the company have contingency plans for down markets?

2\. How do you encourage innovation at [place]?

3\. How has your role from (research the person) changed going to CEO?

------
riskneutral
1\. What are your strategic priorities over the next 12 months?

2\. What is your leadership style like?

------
blihp
Unless you are going to be a direct report (short- and long-term) to the CEO,
specific situational/tactical questions aren't going to be of much value since
your manager (either existing or TBD), rather than the CEO, is going to be
making most of the decisions that directly impact you day-to-day. I'd be
asking more open-ended 'big picture' questions about things I cared about at a
strategic level (how are they funded and is there an eventual exit strategy
and if so what is it[1], overall product/services direction, who they view as
their primary customers/competitors, short and long term challenges to
survival and growth, how do they see me helping them get where they're going
etc) and see where they go with them.[2] Ask followups that try to get them to
elaborate but not necessarily challenge the previous answer(s)... you want to
get their views even if they conflict with yours. You are not trying to change
their mind or show them how smart you are. (if you ask intelligent questions
well, a good CEO will notice)

You're likely to get better answers if you've done at least a bit of homework
about the company and space they're in and ask specific and relevant, rather
than generic checklist questions. Let's say it's a small 10-person company...
they probably don't have any managers yet. So then you'd probably want to ask
some questions to get a feel for how the CEO views management and what makes a
good manager to try to sense of how that's likely to evolve. If they're a
100-person company, that question has already been answered: you should be
talking to a couple of the managers during the interview process and get your
feel for management and their priorities from them. Essentially, try to ask
the CEO the questions you can't get answers to by talking to other people
and/or observing the environment since who and what's already there tells you
more than the CEO's answers would.

[1] Sure, funding/exit strategy questions matter from an economic evaluation
of what the best case financial end-game is for you. But it also tells you a
great deal about what life is going to be like while you work towards it. Your
experience at a 10-person company that is self-funded and profitable is likely
to be very different than one that is VC funded but identical in every other
way. For example, a self-funded startup (more likely to just be a small,
rapidly-growing business) there may be no exit strategy and that can be a good
thing from a quality of life standpoint.

[2] Keep in mind that a lot of the answers you will get to these types
questions will at best be aspirational and at worst be canned responses. Six
months later, business realities might require changing direction and
invalidating them anyway. That's why I wouldn't care too much about the
specific answers (unless they are commitments to you that they are willing to
put in writing), but rather the sense you get of the person and where they
decide to go with the answers. Does the discussion seem casual and natural or
formal and forced? What are their priorities and did they seem cagey, sincere,
controlling, on a mission, narcissistic, driven etc... these indirect answers
will help paint a picture of what you can expect your life at that company to
be like and whether or not you think the CEO has the traits needed to actually
pull it off. If you get no sense of the person and/or everything sounds too
perfect/generic/canned/polished/politically correct... I'd take that as a red
flag.

~~~
eldavido
Best answer here by far. Also judge based both on the content of the answer
and the other party's ability to reason about the question.

In general it's important to be mindful of the fact that hiring is a business
transaction. The CEO's goal is to close (hire) you -- if you get accurate
information as a byproduct of that, great, but accuracy/honesty isn't the
goal.

I've learned to expect that everything coming out of management's mouth is in
furtherance of the shareholder's interests. They are not looking out for you
an employee. If you want real answers to these questions, either work through
your network or form your own opinions. Management will always just spin it --
their view of things is your first and perhaps best data point, but always
cross-check against industry press, friends, and your gut feel/experience.
e.g. if your management consistently says your company is great, you have the
best tech / fastest growth / best investors, actively seek out the other side
of the story (generally outside your company) to see what's fact and what's
bullshit.

------
herbturbo
What is the biggest existential threat to this company today?

------
abarringer
Who's your favorite author on business/leadership?

~~~
jl2718
I like this question, but I find it hard to answer for myself, because I’ve
read an awful lot of fluff nonfiction from the business section and still
can’t think of any that actually tell you how to manage. Mostly just
anecdotes. Which books would you suggest for learning known best management
processes?

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gwbas1c
Why did you start (or join) this company?

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arclyte
When I leave here in 2-3 years, will it be because of the people, or because I
haven't gotten a raise and/or promotion?

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ralusek
What's your salary and why is it higher than mine?

------
OliverChenLei
salary

------
intelliderp
What will be the first task I would be assigned to if I am hired?

