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

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

#51
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.

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

#52
post #51

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.

> 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.

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

#53
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?

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

#54
post #38

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 whatev…

Some of us have enough money that we just don't care. If you want people to tiptoe around your feelings I suggest messaging some broke new grads.

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

#55
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.

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

#56
post #47

Earlier quoted context omitted.

Which examples bother you?

To 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?" (th…

They’re not bad. They’re similar to questions asked by employers to candidates. The fact that you find them arrogant, to me, says that you hold yourself in higher regard than you hold your employees; that you feel superior in some way.

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.

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

#57

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 whet…

These 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.

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

#58
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?

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

#59
post #57

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 whet…

These 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 man…

I 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.

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

#60
post #38

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 whatev…

Some of us have enough money that we just don't care. If you want people to tiptoe around your feelings I suggest messaging some broke new grads.

Why are you even applying to work for someone else's company then if you're so super rich? If you're gonna be arrogant you can expect many companies to shut the door for you.
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