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Ask HN: Best questions for an engineer to ask a CEO during a job interview?
I’m interviewing right now at a lot of startups and am looking for better ways to ask “so, where is this thing headed?”
What do you always make sure to ask?
- suff 8y agoWhat is the startup's burn rate, and how much capital is left, or more generally 'how much more funding runway is left?'
- misja 8y agoGood question but I'm afraid that you will not always get an honest answer.
- shanehoban 8y agoSometimes it's not about getting an honest answer but showcasing that you are aware of the fundamentals of business and introducing this fact to the CEO directly. Depending on your level of interest and intuition, you can gauge the answer provided and measure its truthfulness going forward. It's also a good way to get an idea of how 'fluffy' the CEO is too in their response. This can be a red flag for not wanting to take the job too.
- ascendantlogic 8y agoDepending 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 8y agoYeah 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.
- rewddit 8y agoWhat keeps you up at night?
- eldavido 8y agoNo CEO can or will answer this. Don't even bother asking.
- leothekim 8y agoWill you share slides from the last board meeting?
- floatrock 8y agoOr at least "do you share board meeting slides at the following employee all-hands"
- notus 8y agoWhere do you see yourself in 5 years?
- intelliderp 8y agoWhat will be the first task I would be assigned to if I am hired?
- mpweiher 8y agoOh...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.
- throwaway45765 8y agoNow that you’ve been acquired, how invested are you in the company’s future?
- agrippanux 8y agoAsk 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.
- Apreche 8y agoWhenever I get a chance to talk to an obscenely wealthy person I always ask: "You have enough money you live the rest of your life in idle luxury. You could just go to the beach and never come back. If I had your money, that's what I would do. Why the heck are you still working?" Of course, if it's a job interview, and you want the job, maybe not the best question.
- yunyu 8y agoNot all CEOs are obscenely wealthy...
- Apreche 8y agoI know, but just in case this one is.
- malux85 8y agoSome do go to the beach and never come back. Most dont. Because most are hyper-industrious. Their wealth is a side effect of their addiction to progress. Last Saturday I was at a billionaires house here in London, and he said he does it for the thrill of the hunt. Another told me beaches are boring. After you take 2-3 months off at the beach you want to do some more things, you want to return to what you're good at. They wants something to challenge them.
- 8y ago
- prolepunk 8y agoWhat 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.
- pcurve 8y agoI 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".
- jrauser 8y agoAs a data scientist: What do you want to know about the thing you're building and how it works?
- whatshisface 8y ago"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 8y agoWould 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 8y agoIt'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.
- notjustanymike 8y agoWhat 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 8y agoThese 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 8y agoI 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.
- shanehoban 8y agoRevenue 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)).
- dfee 8y agoMight annoy or alienate a CEO (maybe that’s a warning sign?). But, these are the right questions to ask.
- fucking_tragedy 8y ago> Might annoy or alienate a CEO (maybe that’s a warning sign?) Yes, this is a warning sign. A CEO of a startup should know that employees take on risk by joining and that prudent candidates will want to take the financial health of the company into consideration when comparing offers.
- testpostpls 8y agoThe best candidates dig into product and market and get all the info they need from that.
- warmind99 8y agoDef might, if your tone is off/the CEO is neurotic. If some rando came in trying to gauge how long he could hang on to a job rather than how he can contribute to the idea I'd be a bit put off.
- cloverich 8y agoIts really dependent on the candidate and the position. A quality senior engineer may be gauging the feasibility of ideas that may take _years_ to come to fruition. That requires a lot of non-technical information and both trust and a good working relationship with sr. management. If they are not willing to freely share information, they probably won't utilize the caliber employee who would typically request it. Its no guarantee but personally when I've interviewed people who have asked these types of in depth and / or difficult to answer questions they've turned out to be orders of magnitude higher quality. They know what successful companies look like, and aren't interested in taking chances on companies that won't or can't utilize them to their potential. Doing so requires sharing enough information and trust that the employee can help steer the ship.
- jressey 8y agoTell 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.
- arclyte 8y agoWhen 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?
- monksy 8y ago1. 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?
- takanori 8y agoWhat 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-a-startup-ceo-cf04d71752e8 https://medium.com/@therealpankaj/interview-questions-to-ask...
- jeremy_wiebe 8y agoI’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)?
- tootie 8y agoWhat 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.
- Avalaxy 8y agoThe 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.
- monksy 8y agoEh. As a potential employee, I want to know the leader at the top has a solid plan ahead. It's easy to walk in the CEO role and screw up everything.
- notjustanymike 8y agoWhich examples bother you?
- Avalaxy 8y agoTo name some: - "You have enough money you live the rest of your life in idle luxury. You could just go to the beach and never come back. If I had your money, that's what I would do. Why the heck are you still working?" (this is incredibly assuming) - "Will you share slides from the last board meeting?" (I think if you need this information you'd probably be on the board) - "Where do you see yourself in 5 years?" (this one made me chuckle but it's also insanely arrogant) - "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?" (someone who states up front that they will for a fact leave after a short period will not get hired by me. The tone also implies that he will leave because something bad will inevitably happen) - "What keeps you up at night?" (IDK, seems way too personal, none of the employee's business)
- notjustanymike 8y agoTotally agree with you on those. They're a great way to tank your chances at the final interview, on the basis of "not a good culture fit"
- mcavaliere 8y agoSome 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?
- balabaster 8y agoSince 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.
- gwbas1c 8y agoWhy did you start (or join) this company?
- OliverChenLei 8y agosalary
- jl2718 8y agoIf 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 8y ago> 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.
- iblaine 8y agoI 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?
- dyeje 8y agoMy 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.
- speleo_engr 8y agoDepends 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?
- riskneutral 8y ago1. What are your strategic priorities over the next 12 months? 2. What is your leadership style like?
- suff 8y agoHave you made any ship date commitments to the board, or to stakeholders, or customers?
- herbturbo 8y agoWhat is the biggest existential threat to this company today?
- yingw787 8y ago1. 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).
- abarringer 8y agoWho's your favorite author on business/leadership?
- jl2718 8y agoI 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?
- arh68 8y agoWhat'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.
- andy_ppp 8y agoI 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.
- josephwegner 8y agoThese 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
- ChuckMcM 8y agoThese are perfect. I especially like the cost center question. It is always a red flag if the CEO doesn't have a handle on where the costs are!
- jacklewis 8y agoCan you please clarify why you say "equity is worth at most $0"? If the company is successful surely the equity is worth something.
- raptorraver 8y agoEquity isn’t money, it’s a lottery ticket.
- maximilianroos 8y agoLottery tickets are worth more than $0
- emilecantin 8y agoYes, 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 8y agoAnd 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.
- blihp 8y agoUnless 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.
- narag 8y agoI 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.
- hluska 8y ago“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 8y agoSorry if it isn't obvious and I come off as clueless for asking, but is this to gauge bureaucracy?
- b_t_s 8y agoThis 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.
- ralusek 8y agoWhat's your salary and why is it higher than mine?
- cstrat 8y agoCojones on this guy
- PopeDotNinja 8y ago"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.
- HillRat 8y agoSales. 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 8y agoSpot on HillRat. You nailed it.
- jbduler 8y agoLook 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 8y agoIn 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.
- evilstark 8y ago"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!
- djeikyb 8y agoHave 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.
- klanghans 8y ago“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.
- kthejoker2 8y agoI 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.
- armini 8y agoThe 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.