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?
131 comments
[ 3.1 ms ] story [ 180 ms ] threadDepending 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.
New employee, thinking they're really clever: What would you do different if you had unlimited resources?
Steve Jobs: I do.
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.
"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.
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.
The mostly idle rich simply have different hobbies and social circles than most people. So, you only really hear about the rich people still running companies etc.
What I've found to be productive is to a) Work part-time and b) choose what I work on based on ROI and personal interest. Still plenty of time left for the beach if you work 15 hours per week on rewarding projects.
I sold a company at a young age and had enough money to not have to work for several years. I sat on the beach. I traveled. I had fun.
Then I got tired of it. I really wanted to do something with my life.
So I started another company. That one didn't work out as well as I'd hoped, so I collected myself and invested in/became co-owner of another company. That one has done really well. I don't need to start another company to make money.
But I'm starting another software company now, and excited to do that. I am less motivated by money, and more motivated/excited to see this dream come to fruition.
There are certainly some people for whom the beach doesn't get boring. I absolutely know people who exited for millions, whether as a founder or an early employee, and just retired. They won't be interviewing you, however.
The people who decided to start again are the ones who have a kind of genuine excitement for making the world a better place, and their startup is a vehicle for them to do that.
At my last company our lead investor was Rich Janssen (great name, right) and he said exactly this. He founded Realtor.com and took it public and founded a data analytics company that sold to Myspace. He had a $10M house in Montecito, CA next door to Oprah, and a million dollar yacht. I asked him why he didn't just retire to some warm sandy beach. He said he tried retirement but it didn't work. Golfing and sitting on a beach made him feel old. Working with young people made him feel young.
Quite honestly, I don't think he had enough money to retire on the beach.
This might sound controversial for some, but the answers to these three questions would tell you pretty quickly what kind of company this is.
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.
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.
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)).
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.
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.
2. How do you encourage innovation at [place]?
3. How has your role from (research the person) changed going to CEO?
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’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)?
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.
- "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.
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.
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.
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!
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.
If I have learned anything from startups it is that anyone who can talk a good game can raise money (fyre festival/theranos).
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?
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.