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?
What do you always make sure to ask?
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.
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.
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.
The problem with asking these questions is - what is the criteria for a good vs bad response? What are red flags?
These questions sound super handwavy and can be answered easily by polished talk. They’re useless mostly.
Instead ask specific questions that can reveal deeper issues. If you’re asking about time, then ask - how many months until X? If they waggle around then follow up again - specifically, how many months or quarters do you think it’s going to take to do X?
I've run several startups and done a ton of hiring interviews. FWIW, these are terrible questions to ask a CEO. They are too vague and make it sound like you are trying to fake a challenging question.
More than anything else, these questions would tell me "Here is an employee who will demand a lot of my time."
If you want to ask something about decisions, ask something like "Do you favor consensus or autonomy in decision making?" or "How do junior team members influence team decisions?" or something like that.
The manager question is kind of out of left field. It would be like someone interviewing for a developer position asking "So, what do you think is the purpose of a laptop?"
Anyway, that's ny two cents. Use at your own risk.
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.
Of all the questions I’ve ever asked, I consistently learn the most from this one.
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)).
A better approach is to dive into the product and make a judgement... "What does the company need to do to secure its next round of funding?" VC-scale rule-of-thumb is you need a new funding round every 18 months... 12 months to improve the metrics, then 6 to close the next round. Figure out when the last one was, when the next one comes due, and how honest the company goals are from now until then.
If I join the organization without asking these sorts of questions and realize that the person leading the company doesn't even know how their own company is running that kills my morale. It could also be that when I ask these sorts of questions I am frank about my opinions: I don't mind being part of the machine but I am business oriented and derive motivation/happiness from doing what I can to accelerate that business even further.
Even if they don't offer equity, you still have a significant opportunity cost and risk when you decide to work for a startup. These questions attempt to quantify these.
And rightfully so.
Employee is investing time in effort and receives compensation and equity in case of startups. If equity is non-zero, then obviously employee will ask the same questions an investor would.
Salaries in startups are lower than in most corporations - the difference is what employee might consider to be their cost of investing in the company.
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.
One thing I learned from it, is that how insightful a question is essentially how well it circumvents bias. You can ask something typical and get canned responses, but posing an inquiry designed to elude defense mechanisms, and penetrate an semiconscious, semi-intentional haze will probably (and inadvertently) yield the most revealing answers.
> What cost center would have to be cut to be profitable today?
How much do you pay for equity (in the form of reduced salary), and what's the expected upside?
Venture Capitalists are in the business of making money off successful startups. They work day in and day out on finding startups that are likely to be successful and investing in ways to help them be successful. Most of the time, they're wrong. The only way that VCs are able to be profitable is by having a diverse portfolio of companies in the hope that one is successful enough to outweigh the losses of the others.
Picking out successful startups is (probably) not your expertise, and you only get about a dozen chances (on the high end?) to choose a new employer for the duration of your career. The odds are very very against you. Given those odds, we can value startup equity at approximately $0, perhaps a bit higher.
Unfortunately, most startups offer lower salaries in trade for equity. They also are offering you _options_ instead of actual shares. Unless you stick around long enough for a liquidity event that guarantees the option's value, you will have to exercise those options prior to knowing their true value. This costs you money _twice_ for an entity that has a near-$0 value.
The fact that software engineers are in a good position market-wise is a position of leverage to ask questions to make an informed decision when taking the next step in their career.
Frankly, if a CEO found any questions like these arrogant or out of line, I'd personally wonder if I, as an engineer, could do my job effectively or believe in the company's success. But, to each their own!
- "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)
If someone asked you to share some board slides, you could simply explain they’re company confidential then try to tease out what information they’re after with follow up questions. Or maybe consider that they care enough about the business (or want to appear to) to ask questions like that.
Why is asking where you see yourself in 5 years arrogant? I own my own profitable company, no vc funding. I’ve never been asked that, but if I were, I’d be delighted to give an answer. Totally reasonable question.
If someone asked me why I wasn’t relaxing on the beach, I’d explain to them that it gets old. Sitting idle is a terrible way to spend time, although it might not appear so if you haven’t had the experience. I’d tell them that I hope to get them to a place one day where they could see just how overrated it is and judge for themselves.
What should be the emotional response to that? Does arrogance arouse anger?
"What keeps you up at night" is also a very common question... obviously within the context of an interview, the candidate isn't asking about problems with your marriage or your health or whatever other personal issue you might be thinking of. Typical answers I've heard are figuring out how to scale, hiring fast while maintaining a high quality bar and moving up market. Knowing what the CEO is concerned about is a totally reasonable and relevant piece of knowledge for picking a company.
1. Is a poorly worded "what's your passion" question to the CEO
2. That's a red flag, you can redirect and say minutes are posted ... question to gauge transparency
3. No more arrogant than asking the employee
4. Poorly worded... "how do you plan to keep me here when the market turns in 2-3 years to the next fad"
5. Is a perfectly fine question, not asking about your wife
Some of these are poorly worded, none of them are out of line. If you are not comfortable answering them speaks to your character greatly.
A wordy, trying-to-be-cute way of saying "What motivates you to keep working?" or "Why do you keep working instead of retiring?" which is a pretty good question.
"Will you share slides from the last board meeting?"
A bit presumptuous maybe, but not quite into the realm of arrogance. I would verbally summarize the slides.
"Where do you see yourself in 5 years?"
Nothing arrogant about this one; a CEO should have a 5-year plan at least. Although this particular way of asking it has been used verbatim enough times since I first heard it in the 80s, that it now shuts down my mind immediately due to its blandly mind-numbing cliché quality. Which doesn't speak to the candidate's amazing creativity. Don't ask it this way if you're sitting with a Gen-Xer probably.
"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?"
I mean, you tell me. Are you more "I have a terrible personality and poor social skills" or are you more "I get childishly petulant when I don't get promotions and raises I think I deserve?" Both these things are within your control... and so is your exit from the company for that matter. If you were mature enough to take responsibility that is. Terrible question, don't ever say this. It conveys four negative things about you, all of which I would assume are true.
"What keeps you up at night?"
The question is again trying to be all folksy and cute bygoshdarn bygolly, but at its heart it's a pretty good question. In other words right now what's your biggest obstacle / thing you're worried about / thing that's giving you a pain. At work mind you... not your personal life!
Slides from board meeting are about transparency, i do not want to work at organization that is not transparent about fiances(and especially not at one which has high profits, but very volatile cash reserves). If it gets deflected, but a summary is provided ,it isn't a red flag - it means that employees potentially have access to this data.
if you think asking about your future plans arrogant, why are you asking such questions to employees? this is a legitimate question about where you want to take this company towards.
In most western tech jobs - changing job after a year is norm - not an exception. over here it is frowned upon, but 2-3 years is a long enough time in most cases. And there are two main cases of job hopping: increase in salary is way more significant than any rise given; toxic workplace;
Last one isn't personal, but it has implied context of company itself. what are problems that you want to fix, and potential threats.
those questions are even more important if company is paying in equity. I wouldn't want to work there if i didn't get the answer at least to majority of them. It would be a huge red flag - or i would assume that equity is 100% worthless when comparing compensations between offers.
Relationships of power shifted - there is abundance of jobs, and scarcity of good developers. Quite frankly - there are plenty of bad companies, and few good ones - just like with candidates.
You would hate to bring in a bad horrible person in. We would hate to invest time and effort into useless endeavor.
On the other hand, asking for slides from the last board meeting is a good request from someone deciding whether to accept an offer, and "where do you see yourself in 5 years" and "what keeps you up at night" are both perfectly reasonable questions about how you view the potential development of your venture.
If I have learned anything from startups it is that anyone who can talk a good game can raise money (fyre festival/theranos).
Good software engineers have options, if they're not working somewhere that offers FAANG money it's probably because they value things other than money such as a good mission, small team work environment, good management, etc.
As a rule, your company can't pay FAANG salaries, so if you want good engineers you need to sell them on the other aspects of working with/for you. There's simply no reason for them to take a bigger risk than they feel comfortable with on your company given the current market for strong engineers.
You may not like that, that's fair, but other CEOs will answer these questions and they're competing with you for that talent.
Here (Bay Area) people usually don't apply for jobs, specially jobs at startups, unless they're really into the products/team/tech/... Even old-school walking-dead companies like Cisco/IBM/HPE pay way better than most startups in term of cash compensation. And given the high risk of failure, startup should sell itself hard to attract talents.
I also found those questions are normal, far from being arrogant.
New employee, thinking they're really clever: What would you do different if you had unlimited resources?
Steve Jobs: I do.
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.
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.
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...
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.
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?
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.
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!
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).
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.
Oh God, never do this. The only CEOs who respond well to saccharine flattery are the ones you never want to work for.
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.
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?
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.
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.
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.
How this question is answered gives information about what to focus on, also about how they react to problems.
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)?
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.
* 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?
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.
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.
This might sound controversial for some, but the answers to these three questions would tell you pretty quickly what kind of company this is.
2. How do you encourage innovation at [place]?
3. How has your role from (research the person) changed going to CEO?
2. What is your leadership style like?
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.
In general it's important to be mindful of the fact that hiring is a business transaction. The CEO's goal is to close (hire) you -- if you get accurate information as a byproduct of that, great, but accuracy/honesty isn't the goal.
I've learned to expect that everything coming out of management's mouth is in furtherance of the shareholder's interests. They are not looking out for you an employee. If you want real answers to these questions, either work through your network or form your own opinions. Management will always just spin it -- their view of things is your first and perhaps best data point, but always cross-check against industry press, friends, and your gut feel/experience. e.g. if your management consistently says your company is great, you have the best tech / fastest growth / best investors, actively seek out the other side of the story (generally outside your company) to see what's fact and what's bullshit.
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.