
Ask HN: What can I ask potential employers? - josephwegner
This question is specifically referring to startups, because startups generally have more risk involved.<p>I&#x27;m currently looking at job openings at startups. There&#x27;s some that interest me, but I&#x27;m worried about some of the risk that comes with joining a startup.  That&#x27;s not to say that I&#x27;m not willing to take on any risk, but I at least want to know what I&#x27;m getting in to before I bet me and my families financial well-being on it.<p>That said, I&#x27;m never sure what I&#x27;m allowed to ask startups. Given that I haven&#x27;t been hired yet, I would think some startups would prefer not to give out too much information about business plans or traction statisics.<p>Am I allowed to ask questions like:<p>- How much runway do you have left? What&#x27;s your plan for extending that runway? If you&#x27;re planning on new investments, are you actively seeking that?<p>- Why do you think this product will succeed?<p>- What&#x27;s the end game? Are you hoping for an acquisition, or an IPO, or a lifestyle business? Something in between? Are you close to achieving that goal?<p>- (assuming I&#x27;ve found something the startup is currently struggling with, like churn...  I mostly want to see that they&#x27;re working towards smart solutions) What are you planning to do about your churn problem?
======
tptacek
You can ask any questions you want. If your interviewers are offended by
questions, that's a bad sign, because smart questions are one of the few
valuable social signals you can pick up in a conventional interview; teams
that get pissy about questions are probably rejecting lots of good candidates.

The runways questions should get reasonably specific answers. You should be
able to discuss runway in terms of headcount/months.

You can ask if they think their product will be successful, but that's kind of
silly.

You can ask about endgame, but you're not going to get a straight answer. Your
incentives are wildly out of alignment with management's, and almost always
will remain so. You can ask leading questions about potential acquirers if you
like. Note that bizdev discussions are virtually never transparent, reasonably
so, so don't get upset if important details are omitted from the discussion.

------
cperciva
You can ask any questions you want. Potential employers are not obliged to
answer, of course, and you may decide that their lack of answers is a reason
to seek employment elsewhere. On the other hand, there may be cases where
employers are not able to answer questions (e.g., due to confidential
negotiations which are underway) so not getting an answer doesn't necessarily
mean that they're trying to hide bad news from you.

Similarly, the questions you ask might lead them to decide not to hire you
(e.g., if one of the questions is "how on earth do you expect to get people to
pay for such a stupid product?").

~~~
ape4
Even if you ask the "stupid product" more tactfully. eg "I can't see a large
market for this product."

~~~
jtheory
No need for "I can't", even. They probably have solutions in mind (the target
market may be bigger than you think, or has deeper pockets); you're asking to
hear them. Put in a bit of thought before the interview, and charitably assume
they've put in more. (If they haven't, that's a bad sign, of course.)

"Tell me more about your target market -- how many pro wedding planners are
there out there who might be actively seeking out something like this? Are you
also targeting self-planners?"

------
MehdiEG
You can certainly ask these questions. In fact, as a startup co-founder
myself, I would find a prospective employee asking these questions to be a
very good sign as it demonstrates that:

1) You understand what a startup is and how it works. Most people don't. It's
easy to forget it when you've been in the startup world for a while but tech
startups are a very strange type of business that most people simply don't
understand. Angel / VC funding, valuation, runway and exits are completely
foreign concepts to most people. If you demonstrate that you understand what a
startup is and yet still want to work for one, then you're more likely to be
the type of person who will stick around even when times are rough.

2) You're actually interested.

And if I was to apply for a job at a startup, I would expect the founders to
be completely transparent about these things. Something's fishy if they try to
change the subject.

------
misterjangles
I think those are all perfectly fair questions however I would take the
answers you get with a grain of salt. I wouldn't expect an employer to admit
they're 6 weeks away from going under at a job interview.

Startups are risky and a lot of times you are convincing people (including
yourself) that it is going to work. So startup employers kinda have to be
optimistic and positive, otherwise everybody would be freaking out and fearing
for their job.

Also - without having any idea what startup you are talking about - the odds
are against you that the company will make it. That's just the reality of
startup life.

~~~
alok-g
Which is why one should ask in ways that are more likely to generate good
answers for the question you actually have.

So "Why do you think this product will succeed?" may be posed as "What are the
key risk factors involved (that I can help you with)?" The former is a
question about their value proposition against the competition, and they would
have articulated it often enough already to be convincing to you as well. The
latter would open them up somewhat about the risk factors in their path of
success.

------
the_watcher
I think asking for a rough estimate of runway is totally reasonable. Just
don't expect them to tell you how much cash they have on hand or to get an
exact timeline. But expecting something like "one month," "six months but we
are talking about ways to increase that," "one year," or ""one year+" seem
like reasonable responses to me if they expect you to take a leap of faith
joining them.

Are you seeking new investment is a reasonable question, but it could
reasonably not be answered, I think.

Why you think the product will succeed is a question I can't imagine not
asking.

What's the end game is a great question. If you are joining a startup, you
need to know the end game so you can properly value your compensation.

If you know about a problem, you absolutely should ask how they plan to
address it. Again, this could reasonably not be answered with too much detail
on the startups end (you'll likely get the kind of answer a reporter would).

The answer or lack thereof are all very valuable pieces of information, and no
company I would like to work for would hold me asking them against them (so
long as I respect their wishes in terms of what is actually shared).

------
snorkel
All startups are:

1\. going to give you the same super optimistic answers about funding and
runway because they usually start posting jobs when either they just got more
funding or they are about get more funding and everything is wonderful
according to them. They're not going to tell you "Dude, we're really screwed.
We have about 3 months left! You still wanna job here?"

2\. some will not hire you just for asking because they prefer employees who
can take the risk

To find out what their true health is, ask them:

1\. How many paying customers did you have last year?

2\. How many paying customers did you add this year?

3\. How many paying customers canceled, or what's your cancellation rate?

A good answer indicates healthy year-over-year growth with a low cancellation
rate that speaks to good customer retention and customer satisfaction.
Especially in a subscription business retaining customers is critical.

If the company has less than 20 people are the answer is "I don't know" or "0"
or "1" or "We weren't in business last year" or "We don't charge any customers
yet." then it's has approx 50:50 odds of surviving another year.

~~~
jtheory
The closer you can get to talking about risk honestly, the better.

> 2\. some will not hire you just for asking because they prefer employees who
> can take the risk

You can tell them the level of risk you can take. If you have a new baby and
only 1 month of savings, maybe it's for the best they don't hire you if
they're in a weak position.

On the other hand, if you're single and have a ton of savings from a
successful exit, you may be ready for a hail mary job. Make sure they know you
the risk isn't a concern for you.

------
jvns
You can ask anything you want. Prefixing your questions with "I want to know
what I'm getting into before I bet my family's well-being on it" is a great
way to start.

When I was interviewing, I asked literally anything I wanted to know, and
people in general responded really well. If something is confidential, they'll
tell you, and you can try to refine the question to something they can tell
you.

I brought a small notebook of questions to interviews and referred to it to
make sure I didn't forget anything important. Nobody seemed to think this was
weird.

Blog post I wrote about this: [http://jvns.ca/blog/2013/12/30/questions-im-
asking-in-interv...](http://jvns.ca/blog/2013/12/30/questions-im-asking-in-
interviews/)

~~~
toomuchtodo
Julia,

I compiled this gist from your blog post when you first posted it. Can you
throw it up on your Github account if you have one? I don't want to take
credit for your work, but I did think it would be awesome to make it a
versioned doc that people could contribute to.

[https://gist.github.com/anonymous/be647549b757259e4732](https://gist.github.com/anonymous/be647549b757259e4732)

------
zacinbusiness
I recently had an interview with a pretty high-profile company and I asked
them why they thought their product was better, or at least how it was
different, than its primary competitor. The interviewer seemed pretty pissed
that I asked that, and in my opinion the answer was essentially that "Our
product has fewer features" (she said that it was simpler, which isn't really
true).

~~~
paulbaumgart
Sounds like a shortcoming they're trying to rationalize away. Major warning
sign, there.

~~~
zacinbusiness
Yeah I thought the same thing. Didn't get the job and then got a better one
just a week later, so it worked out. I hope them the best, but they act like a
startup even though they've been around for a long time.

------
roberthahn
If I were hiring (I'm not), I would be delighted if you asked those questions.
Other questions you should ask:

\- What are your sales goals? How do you intend to hit them?

\- Do you keep and maintain a cash flow statement? (Not having one, and not
updating it regularly is a red flag - its job is to tell you when the money
runs out)

\- Who is responsible for sales? Do they have the experience required? If not,
what's the plan to make up for the shortfall?

\- Do you share your business goals with the entire company? How do you ensure
that the entire team is aligned with those goals?

\- What are the biggest challenges you're struggling to overcome?

------
sharkweek
Those seem like perfectly normal questions - in fact anyone who acted
defensive toward those types of questions are likely less confident in the
answers they would have to give.

------
brudgers
In my opinion, once equity is on the table then reluctance to answer any
financial question is a bad sign. That's not to say that hesitation is a bad
sign - a founder may not have thought it all through yet. But once it is put
in terms of "I cannot evaluate your offer without knowing these things" then
it is reasonable to expect forthright answers.

However, before there is an offer on the table, then this sort of question
might be considered premature without the interviewer turning to the subject
on their own which if they are pumped about the company they are likely to do
anyway.

Realize that these questions can come across as mercenary. That is, if you are
evaluating the job solely as an accountant then it would be prudent for an
employer to assume that you will only stick until something better comes
along. That's not always a good impression to leave at an interview.

Consider that the interviewer for a technical position may not really be
focused on the business side. In a startup a technical interviewer who has
detailed financial models in their forebrain may be a sign they are already
looking at an exit rather than growth.

In the end, everything comes down to a matter of trust. You're betting the
future on whether or not you can trust the company to take your interests into
account.

Good luck.

------
tedchs
When I interviewed with an early-stage startup, I met with the CEO and
interviewed him just as much as he interviewed me, and I asked questions like:

\- are you profitable?

\- if you had zero revenue starting today how long would you last?

\- have you ever missed payroll?

His candor in answering these questions was a big plus for my decision to
join.

Note, these were asked near the END of the interview process, actually after
they made me an offer. In general, after you get the written offer is a good
time to ask any final hard questions to confirm whether you want to hitch
yourself to their wagon for the next couple years.

You should be prepared for many of the questions you listed to be legitimately
answered with "I don't know exactly what the future will hold". E.g. A
business planning for a buyout might later realize they are better off on
their own, so it's better for all if they hadn't told you one thing before and
then changed course.

~~~
josephwegner
Good point on asking if they've ever missed payroll.. I got burned on a
previous startup by that, and that would have been a HUGE red flag before I
started there.

------
4wardobserver
Going with a startup means that they are going to ask you to dedicate much of
not all of your life to them for a while. With that in mind, they need to be
honest and frank with you. They need to trust you and you need to trust them.

Tough questions from them is expected. Tough questions for them is only fair
given what they want from you. So, if they dodge them or you don't feel that
they are telling you everything, don't take the job. If you can't trust them
now, it'll be harder to trust them later.

Suggested questions:

1\. Why do you feel that this company with its product or service is better
than what is out there? (They need to convince YOU).

2\. Where are your risks as a company? (Finance, competition etc)

3\. If your CEO spending time on running the company or raising funds? (You
don't want both at the SAME time)

4\. How many employees did you have a year ago, six months ago and now? (Good
growth means the right direction)

------
joelgrus
Those are all good questions. (I have been asked all of them by people I've
interviewed.)

Also, necessarily all the people interviewing you have already made the choice
to leave whatever they were doing before and join the startup, you should ask
them how they decided that was a good risk to take.

------
einhverfr
By asking these questions you demonstrate you are interested in the job as an
investor of your effort, not as someone seeking a paycheck. By all means ask
these questions. By all means take the answers with a boatload of salt.

Now, they may not answer. They may not be able to answer. But what they do say
and how they approach it will tell you a lot about whether they are looking
for employees to help build the company or just to do work. And if they decide
not to hire you because you asked the questions, you _really don 't want to
work there anyway._

------
BioGeek
Some more things you could ask in this article by Hacker School alumna Julia
Evans [1] and this article on Runtime Era [2].

[1] [http://jvns.ca/blog/2013/12/30/questions-im-asking-in-
interv...](http://jvns.ca/blog/2013/12/30/questions-im-asking-in-interviews/)
[2] [http://www.runtime-era.com/2013/03/my-interview-questions-
fo...](http://www.runtime-era.com/2013/03/my-interview-questions-for-
potential.html)

------
yoodenvranx
"do you plan to move the company to another city in the next 2 years?"

This happend to my girlfriend recently... She got her dreamjob, moved to the
other side of the country, invested some money to get a nice flat and then
after 4 weeks they told her: "btw, we are going to move to a town 100 km from
here in 5 months". Since she got the job I also moved to this new town and now
we both have to move again.

------
miles_matthias
A little off topic but my advice is to have any agreements be explicit and in
writing. Probably obvious to some, but it's easy to get a good conversation
going, just go with the flow, and not follow up afterwards with an explicit
agreement around terms/expectations. In a startup this can be even more
important because you may find out they don't have the resources to give you
what you want.

------
calibraxis
Ideally, you'd get to know one of the employees. Then ask away. Ideally you'd
want one of the more employees more capable of cynicism (or realism, if you
wish); statements like, "It's a really good environment!" are useless. You can
ask what would happen if you perturb the system: "What if I do <something
often interpreted as upsetting the chain of command>?"

If you know the industry, or can speak with a friend in it, that's good. Then
you can predict much of what they do/think, and watch out for
irrational/ignorant deviations.

Will they give you contact info of a normal employee, or leave you alone to
speak with them? If they're really good, they'll do it without you needing to
ask.

Bosses are professional liars. (This includes technically true statements
designed to mislead. Whether they're even aware of it is not relevant.)
Conditioned daily to say what maximizes their interests, or they fail. They
are virtually the worst sources of direct info, unless they open up their
books and emails to you (which they won't). They often don't even know some
answers due to blindspots.

So when speaking with bosses, I try to observe "rationality" (which I agree is
subjective). Charismatic talkiness is a flag; it may indicate ego. Evaluating
it isn't easy; that practiced charisma may be useful for success, but it can
also be a pain to work with.

One thing I care about is how much ability I'll have to help the company
maximize its success. Part of that is knowing how many employees there
currently are, and what kind of people they are, because their work is "legacy
code" as far as I'm concerned. Do I have to deal with it? (Because usually
it'll suck.)

But really, the high-risk sort of startups come with... well, inherent risk.

------
the_watcher
One final note: The "no stupid questions" rule is still a good one. Employers
should want to hire employees that want to know as much as possible about the
business they are in. Even if the question seems unbelievably basic, not
knowing the answer and making the wrong decision because of it is so much
worse.

------
auctiontheory
You can ask anything you want. On the other hand, you should realize that your
questions convey your state of mind, and anything you say can and will be used
against you. But that's not necessarily a bad thing: apparently you have a
family. If you have a lot of lifestyle questions, and they are a 7 day/week
operation, both sides may decide it's not a good fit.

A good company will be delighted to hire an engineer (assuming you are an
engineer) who asks intelligent questions about the business - it shows that
you can go above and beyond doing "your job," and that you are aware that your
technical work has a business outcome. You do not want to work for an employer
who is threatened by your questions, or refuses to answer (most of) them.

------
obicho
I have worked at a number of startups and I hire my teammates on occasions.

You actually need to ask intelligent questions that show that you have done
your research thoroughly about the company.

Avoid \----- \- asking trivial questions that are already answerable through a
simple look on their website or on Google

Do \-- \- ask about their competitors and how they differ from each other and
where does the company come in the eco system

\- ask about founder/manager background to evaluate the team's chance for
success base on the experience of founders team

\- look up info on google news about the company or the industry which the
company is in. Think of questions to ask them by referencing the news

\- do ask for product roadmap and strategy. Ask hypothetical questions like
given situation X and Y, how would the company handle it and why, etc.

Hope this helps

------
ig1
They're all perfectly reasonable questions to ask.

------
beat
This is interesting to me because at some point this year, I will need to
start doing straight hiring for my own early stage startup. And I can tell you
right now that if you ask questions that express an understanding of how
startups actually work and legitimate concern about the health of the
business, I'm going to be _far more inclined_ to hire you. I'm looking for
people who are not only technically sound, but are culturally prepared for
working at an early stage startup.

I find myself doing informal, unannounced "technical interview" with just
about every interesting techie I meet these days. Most simply aren't good
enough to be interesting very long. :(

------
danielweber
"How much runway" is completely above-the-board. If they won't tell you, run.

"What's the end-game?" will probably give you the runaround -- it certainly
has for me, with silly redirects like "we are more interested in building
value for our customers" when it's obvious that management is always extremely
concerned about the long-term plan, so this is interesting to write down and
compare to what happens later to see what they say, but of no real use during
your interview process.

------
elmuchoprez
How many days of vacation did you personally take in the past year?

~~~
jes5199
one day a coworker came over to my desk and said

"The guy I was interviewing just asked me what time I come into work in the
morning! Can you believe the nerve? I don't think that's a good sign."

... and that's when I realized that we had some serious overworking-culture
problems and I needed to get out of there.

~~~
AznHisoka
Ha, thats one of the top questions I ask employers: What's the usual hours?
Seriously, I'm not gonna work my ass 10-12 hours a day for any company unless
there's a huge reward at the end - looking at you Facebook, post IPO, Speaking
of which, I'd be pretty pissed if I was a FB employee seeing 16 billion being
thrown at a handful of people, while I'm working my ass off.

------
TallGuyShort
Those are all reasonable questions, IMO. When I think of the people I've
worked with who successfully passed a company's interview process but turned
out to be a short-lived employees or a poor fit for the organization, the
situation could have been avoided if the employee had interviewed the employer
more and understood what they were getting into better. Both parties need to
do the research and ensure they want to work with the other party.

------
hluska
Those questions are excellent.

Taking a job at an early stage startup is a lot like making an angel
investment. Consequently, you need to think like an investor and ask tough
questions. While you're asking the questions (hopefully you get to ask the
founders), pay attention to both what they say and how they say it. If they're
resistant, avoidant, or generally difficult to get answers out of, you should
be very careful.

------
mcv
These sound like very smart questions to ask. As you say, working for a
startup is risky. They could go bankrupt and leave you with a few unpaid
months of work. You want to be able to understand and manage the risk you're
taking.

And if they don't want to answer these, particularly if they don't even want
to share their basic business model, I'd be a bit wary of working there.

------
gesman
Watch for signs in between the lines (answers), not for the answers
themselves.

All answers will be optimistic and positive BS, but pay attention to subtle
things, body language, eye contacts, hands gestures, finger movements, your
own emotional feelings when communicating with these people, etc...

Some of these will be green signs, some are red.

Do not ignore little things - they are the ultimate answers.

------
namelezz
Ask your employers to tell you someone in his or her team that s/he enjoys
working with and why. This will tell you if you will be fit well and valued in
the team. Otherwise, you may feel isolated later, or you may join a team and
realize that the popular ones are not doing anything but kissing managers'
butt. It's a sad team!

------
cmer
Too few candidates ask about the founding/management team IMO. Prior success
is often an indicator of future success.

------
probinso
"What has been your career path to this point?" \- tells you their
professional history, their startup background, let's you know what their
comfertable talking about wrt the end of their previous companies.

I also use this question for larger companies, to get a feel of the calibur of
potential peers.

------
balls187
Great topic, I think it's a smart idea to ask questions, especially if you're
concerned about risk, but in my opinion, with a change in approach you can get
a more effective answers.

Most of your questions should be directed at the CEO, or at the very least a
co-founder. Depending on the size of the company, the people you're
interviewing may not know about funding issues and exit strategies.

Asking about Runway is a good question. If you're worried about coming into
work one day and finding the office closed, ask point blank about your
concern. This is a good test question to see if the company believes in
transparency.

You're right, the company may not want to go into too much details on it's
traction and funding, but they should be comfortable talking openly about your
concerns.

As to new funding, you should be able to find out their last funding round,
either through Crunchbase, or from SEC Filings. Startups tend to fundraise in
the late spring, and the late fall. Come thanksgiving, investors are hunkered
down for the holidays, and summer vacations make it difficult to get people
together. So if you're approaching a company during those times, you can
assume their prepping for a funding push later.

Despite what others may say, the CEO is always fundraising. Perhaps not
actively, but working towards their next round.

Ask about milestones towards their next raise. If their a consumer app, what
are their MAU targets. If their SaaS business, what are their Churn and MRR
numbers. What are some other milestones that they're pushing towards?

Questions about potential exits aren't that interesting, because it's easy to
judge a business that is poised for IPO, and those that are ripe for
acquisition.

If the business has taken institutional money, then there really is only two
viable outcomes: Acquisition, or going Public. Investors won't invest in
lifestyle businesses.

[Soapbox] Your family's financial well-being hopefully isn't tied to a stint
at a startup. Perhaps I'm a bit old school, but I believe in some amount of
financial planning--something like a rainy day fund that can keep you afloat
for 3 months without income. [/Soapbox]

It's not just startups that are at risk for closing down. Irrational Games
just closed shop and let go of all but 15 people, and that was despite
releasing several AAAA blockbuster titles.

Losing your job at a startup isn't nearly as bad as you might think. There is
a major shortfall in technical talent in most startup hubs, investors and
founders are always looking for talent. After Zynga shut it's seattle offices
down, a local VC here had an open house for the employees that were let go.
So, if things go bad, many founders and investors will work to help secure you
a position elsewhere. Plus, again, it's hard to hire people.

------
michaelochurch
You can and must ask those questions. If they find it rude or "forward", then
that's a good sign that you should not join them.

Salary, title, equity, benefits and vacation time are best discussed (and
negotiated) after an offer is in place. I _wish_ it were socially acceptable
to discuss these earlier (it would save a lot of wasted time) but it's usually
not. What the business is doing and how much runway it has, you should ask
early. You have a right to know, and if they have a real business they believe
in, they'll be excited to tell you.

~~~
kabdib
At some point, you are interviewing them.

I've made a few mistakes in that direction. One memorable one is the startup
where (a) I learned the phrase "train wreck", (b) witnessed a fight between
VCs wherein various employees had to pick sides, (c) had to talk to a
psychologist the company hired to find out "what was wrong in engineering"
[ans: managers were morons], (d) had a meeting with Smokey Wallace -- an early
Adobe heavy -- one fine Sunday morning to do a technical brief of what the
company was about [ans: not much, could have been replaced with 2KSLOC of
Perl], and (e) had the president of the company break down crying when I told
him I was quitting.

Due diligence would have saved me from everything, but at east I got some
interesting stories. I'll never get that ten months back, though.

------
benched
I'm having trouble thinking of questions where the answers would have
information content.

For example, you could ask whether your entire chain of command and half the
team are planning on leaving within a year, but the answer you get won't have
any information content. It will be about how everyone loves what they're
doing and is fully committed to the mission.

