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Ask HN: Best questions for an engineer to ask a CEO during a job interview?

by northisup on 3/27/19, 2:46 PM with 129 comments

• by notjustanymike on 3/27/19, 3:16 PM

  What are the problems you are personally trying to solve?

  How do you like to make decisions?

  What do you believe is the purpose of a manager?

  What do you believe motivates employees at your company?

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

  How do you recognize major achievements?

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

• by HillRat on 3/28/19, 2:46 AM

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

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

• by hluska on 3/27/19, 11:54 PM

  “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.

• by shanehoban on 3/27/19, 3:16 PM

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

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

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

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

• by josephwegner on 3/27/19, 9:56 PM

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

• by Avalaxy on 3/27/19, 3:39 PM

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

• by mpweiher on 3/27/19, 2:58 PM

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

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

  Steve Jobs: I do.

• by dyeje on 3/27/19, 4:24 PM

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

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

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

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

• by PopeDotNinja on 3/28/19, 2:03 AM

  "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.

• by takanori on 3/27/19, 3:24 PM

  What value does the product drive for the target stakeholder?

  At what frequency is this value delivered to the stakeholder?

  How does the stakeholder know they are receiving value?

  How does the value compare with the price paid?

  What is the product’s TAM?

  What things are out of the company’s control?

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

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

  Explanations here:

  https://medium.com/@therealpankaj/interview-questions-to-ask...

• by leothekim on 3/27/19, 2:55 PM

  Will you share slides from the last board meeting?

• by arh68 on 3/27/19, 8:46 PM

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

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

• by speleo_engr on 3/27/19, 4:46 PM

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

  Have you ever been close to missing payroll?

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

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

• by tootie on 3/27/19, 3:36 PM

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

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

• by evilstark on 3/28/19, 4:25 AM

  "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!

• by yingw787 on 3/27/19, 8:30 PM

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

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

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

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

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

• by jl2718 on 3/27/19, 4:04 PM

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

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

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

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

  So ask them how they became so wonderful.

• by kthejoker2 on 3/28/19, 8:30 AM

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

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

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

• by mcavaliere on 3/27/19, 3:42 PM

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

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

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

• by jbduler on 3/28/19, 3:52 AM

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

• by agrippanux on 3/27/19, 3:02 PM

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

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

• by jressey on 3/27/19, 3:19 PM

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

• by balabaster on 3/27/19, 3:45 PM

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

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

• by narag on 3/27/19, 10:34 PM

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

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

• by pcurve on 3/27/19, 3:09 PM

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

• by jeremy_wiebe on 3/27/19, 3:34 PM

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

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

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

• by notus on 3/27/19, 2:56 PM

  Where do you see yourself in 5 years?

• by rewddit on 3/27/19, 2:54 PM

  What keeps you up at night?

• by armini on 3/30/19, 2:27 AM

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

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

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

• by iblaine on 3/27/19, 4:09 PM

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

  * Does the company have contingency plans for down markets?

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

  * Will you share slides from the last board meeting?

  * Why the heck are you still working?

  * Have you had any regrets?

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

• by klanghans on 3/28/19, 6:39 AM

  “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.

• by djeikyb on 3/28/19, 5:55 AM

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

• by jrauser on 3/27/19, 3:09 PM

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

• by prolepunk on 3/27/19, 3:08 PM

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

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

• by andy_ppp on 3/27/19, 9:41 PM

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

• by throwaway45765 on 3/27/19, 3:01 PM

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

• by monksy on 3/27/19, 3:23 PM

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

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

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

• by riskneutral on 3/27/19, 5:47 PM

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

  2. What is your leadership style like?

• by blihp on 3/27/19, 10:05 PM

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

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

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

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

• by herbturbo on 3/27/19, 8:15 PM

  What is the biggest existential threat to this company today?

• by abarringer on 3/27/19, 8:40 PM

  Who's your favorite author on business/leadership?

• by gwbas1c on 3/27/19, 3:46 PM

  Why did you start (or join) this company?

• by arclyte on 3/27/19, 3:19 PM

  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?

• by ralusek on 3/28/19, 12:25 AM

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

• by OliverChenLei on 3/27/19, 3:48 PM

  salary

• by suff on 3/27/19, 2:50 PM

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

• by suff on 3/27/19, 6:38 PM

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

• by intelliderp on 3/27/19, 2:58 PM

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