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Ask HN: What can I ask potential employers?
64 points by josephwegner on Feb 24, 2014 | hide | past | web | favorite | 50 comments
This question is specifically referring to startups, because startups generally have more risk involved.

I'm currently looking at job openings at startups. There's some that interest me, but I'm worried about some of the risk that comes with joining a startup. That's not to say that I'm not willing to take on any risk, but I at least want to know what I'm getting in to before I bet me and my families financial well-being on it.

That said, I'm never sure what I'm allowed to ask startups. Given that I haven't been hired yet, I would think some startups would prefer not to give out too much information about business plans or traction statisics.

Am I allowed to ask questions like:

- How much runway do you have left? What's your plan for extending that runway? If you're planning on new investments, are you actively seeking that?

- Why do you think this product will succeed?

- What'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?

- (assuming I've found something the startup is currently struggling with, like churn... I mostly want to see that they're working towards smart solutions) What are you planning to do about your churn problem?




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.


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?").


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


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?"


I've pushed the "I really don't see the market for this" question pretty hard when interviewing last time. It showed that I was trying to really understand what the offering was about.

I got the job offer, it was a lowball offer, so I passed, whatever. It does show that some employers like it when people really engage (in a constructive way) with the big picture of what people are trying to do.


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.


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.


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.


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).


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.


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.


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...


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


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).


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


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.


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?


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.


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.


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.


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.


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)


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.


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.


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... [2] http://www.runtime-era.com/2013/03/my-interview-questions-fo...


"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.


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.


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.


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.


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.


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


They're all perfectly reasonable questions to ask.


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. :(


"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.


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


How many hours have you worked the last 3 weeks?


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.


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.


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.


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.


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.


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.


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!


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


"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.


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.


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.


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.


One benefit of working with agency recruiters is that you can find out at least parts of the comp plan (vaca, 401k, bennies) without having to ask directly. If you walk in and start asking 'what's in it for me?' questions before asking the 'good questions' (that poster listed) founders may judge that you are only interested in comp.

Having information on the bennies and perks before talking about cash comp is pretty important. If the company pays 100% of healthcare premiums and another pays 50%, that could be a 5-10K adjustment alone. 1 week vacation accounts for 2% of comp. All the little things start to add up, and if you throw out a number early on without knowing these things you may need to backpedal.


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.




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