Ask HN: What can I ask potential employers?

64 points by josephwegner ↗ HN
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?

53 comments

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

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?").

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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.

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.

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.

"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.

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.

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?

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

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)

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.

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).

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

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.

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.

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!
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.

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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.