With these kind of things I don't think asking questions is really going to tell you much.

People can present themselves differently than they are, and especially people with lower morales will have no problem presenting themselves differently if that is in their interest. Look at pretty much any big company CEO.

If you do need to gauge someone, look at their history, look at their actions, and look at their incentives. If they don't align with what they're saying you should not expect them to act any different than they did before.

I came here to say look at what they do not what they say.

This applies not only to CEOs but to every single human on the planet. One thing I have learned is that many people seem to be easily tricked by certain types of humans saying one thing and doing another (which is contradictory to the "said" thing). It is certainly frustrating to watch happen, when it involves people you care about.

> One thing I have learned is that many people seem to be easily tricked by certain types of humans saying one thing and doing another

Seems to me that almost everybody. And the ones not tricked just happened to be looking at a different place by chance, and won't replicate the same result a different time.

We definitively need some kind of tooling to deal with this.

Talk is cheap.

I found a good question to spring is 'name a time you had to make a moral decision'. If someone thinks about decisions in terms of morality it's a good open-ended question that'll lead into how they approach moral dilemmas. If you suspect you're getting a rehearsed answer, follow up by asking about a moral decision they made where they would have acted differently today. Anyone who rehearses an answer to that question is going to rehearse one where they made the right call, but anyone who actually thinks about things in terms of morality is going to remember a time they made a mistake.

That is an excellent answer.

This.

You’re in a desert walking along in the sand when all of the sudden you look down, and you see a tortoise, it’s crawling toward you. You reach down, you flip the tortoise over on its back. The tortoise lays on its back, its belly baking in the hot sun, beating its legs trying to turn itself over, but it can’t, not without your help. But you’re not helping. Why is that?

.. why would I flip it in the first place?

Did I just disqualify myself as a CEO

Unironically, to a large demographic here, yes.

Fiiine, I Googled it.

.. I'll watch the film later.

Describe in single words, only the good things that come into your mind about your mother.

deceased

If trustworthiness were able to be gauged by a single question world political history would be much more boring.

That being said, asking a CEO to take responsibility for a mistake is a pretty good indicator.

If they own the mistake. That's good. If they own the mistake and try to fix it. That's better. If they own the mistake and ask the people wronged how to make amends. They're probably not a CEO.

What does "take responsibility for a mistake" even mean when it comes to a CEO? Most recent examples of a CEO "taking responsibility" for mistakes that I can think of all involve them looking visibly sad on camera, sending an all-hands E-mail telling people how seriously they are taking things, and of course, laying off a bunch of lower-level employees. Occasionally, they also quit with a $XX million golden parachute, off to be CEO at another company.

You can't just say the magic incantation "I take full responsibility" and leave it at that.

> You can't just say the magic incantation "I take full responsibility" and leave it at that.

A decent rule of thumb is that if someone has to overtly say "I take full responsibility", they aren't taking full responsibility.

There are a bunch of mundane questions that can help gauge how much they care about general well-being... none of these are gotchas, just questions companies generally don't like answering.

What are your views on unionization? Would you voluntarily recognize an union formed by your employees?

Why don't our job postings have salary ranges?

Remote work?

Open-source?

Climate change?

How do you think our new office will impact the local community and housing affordability?

What philanthropic activities do you engage in? What about our company?

How will our culture change once our company achieves success?

What can we get in writing, in revised bylaws, rather than a verbal promise?

The idea that interrogating someone will provide any insight into their moral character is pretty naïve. Look at someone's actions, nothing they say is of account.

It takes practice. After meeting 100 CEOs and watching their companies evolve for 5 years, most people can be OK at it. Some people (famously Jessica Livingston) are much better than average. But few people have the chance to practice that much.

If you haven't had a lot of practice, ask people who have. Investors and other CEOs typically have lots of practice, though sometimes they aren't trustworthy themselves. So ask several people and discard outlying opinions.

Ignore the press, unless there are external facts like a conviction. The press is full of snark and innuendo about CEOs, most of which is just reporters trying to cook up a narrative people will click on.

Fly them in. Give them a driver to assist them in arriving and getting to the interview. Have the driver make an obvious mistake. Circle the block or arrive a couple of minutes late.

Auto-fail anyone who treats the driver poorly. Find the guy that wants and/or tries to help the driver succeed.

Various ways to see the inner person and not the "show person" on display for the interview.

Pretty sure that's from a movie.

Is it? I don't really watch movies.

But that's pretty funny to learn :) Nice.

I think trying to judge morality by anything other than actions is probably the wrong approach, you could ask clarifying questions on some of their previous decision making but hypotheticals and such likely aren't a strong signal either way.

You aren't looking for your soulmate and you aren't a psychologist. The only way you are going to know whether they can be trusted is working with them. Be prepared to move on when things are no longer to your liking.

I do this for a living and I don’t have a great answer. There’s a gut instinct involved. I try to understand how execs are compensated or otherwise incentivized, and then ask myself if there’s a reason they would screw over their stakeholders embedded in their incentives or enabled through some governance loophole. Many are trained to be great at deflecting (anyone with media training should be) so indirect questions tend to be your ally.

This kind of approach would mean you also look at governance structures, which in the case of OpenAI would have focused on the issues with their board structure.

It's your birthday. Someone gives you a calfskin wallet. How do you react?

Hmm, my theory would be: don't look for the morally spotless ones, look for the ones with internal consistency, authenticity, and honesty. Everyone shits and everyone fucks, and in business, everyone cares about money (even if for different reasons). Yet when the time comes to discuss these things publicly, most suddenly become goody-goodies. So that's the first kind of lie. From there on out many other lies will follow. So seeing some unpolished views and although I think is good because where there's a lot of polish it's probably not 100% true.

"What's an instance where you gave up power for principle?"

Being a CEO is already the ultimate answer to the question "Do you care about money or morals". There is a reason that psychopaths are massively overrepresented as CEOs.

My answer would be to check their technical background to see how they ended up as CEO. Was it circumstance, or raw machiavellian ambition?

If you must ask one question I would probably ask, "Do you hate being a CEO?". If they answer "Yes" it likely means they are doing it out of responsibility rather than pathalogical persuit of the unattainable.

This is a good question and there are many good responses here. I wish there was a silver bullet, but after decades of startups and launching new companies and transactions and exits, I've seen even the most ethical people do questionable things the minute even modest sums of money were involved.

You really have to take off your rose-tinted glasses and try to get to know what their core values are. That is the only way.

Ask them what are they going to do if their workforce decides to unionize.

Tell them that their response is going to be publicized beforehand.

> What questions can tech CEOs be asked, to gauge their moral trustworthiness?

None, except to the extent that (there are other requirements, but these apply on top of them): (1) you already know what their honest answers would be, and (2) you can guarantee that they don't know that you know this.

By what standard do you define morality?

I took the question as being about "moral trustworthiness" rather than about having any specific moral code. In my view, "moral trustworthiness" is having a moral code that you adhere to, regardless of what that code actually is. It's the opposite of "moral opportunist", or someone whose moral code changes according to what happens to be the most advantageous at the time.

But I could be overthinking this.

I mean, the nazi’s, Chinese communist party, and ISIS all have a moral code they adhere to.

I think, WHICH moral code you choose has some relevance here.

This is kind of a meaningless question to raise in a vacuum.

For most people who get the chance to talk with "tech CEOs", the basic context of the conversation is usually built on a profit-seeking foundation -- Should I invest in you? Should I sign a commercial deal with you? Should I work with you as an employee? On that basis, morality is often orthogonal to profit (sometimes opposed, and rarely aligned with).

Most people, most of the time, if they are evaluating tech CEOs for any semblance of "morality" or ethics, it is usually most pertinent to consider business ethics -- Will you uphold the terms of a contract? Will you sincerely work to create shareholder value (above personal goals or benefits)? Will you be a good leader for your employees, treat them fairly according to professional standards and company policies? This level of ethics is necessary in order to conduct good business; trust is currency and if you cannot trust a CEO to uphold standard business and professional ethics, then the cost of doing business in an environment of mistrust usually becomes exceedingly high.

Anything beyond that, like is this CEO a "good person", are they working for the betterment of mankind, etc., is usually not worth evaluating for 95% of people -- not because it's unimportant, but because (a) capitalism is amoral and grafting morality on to it is kind of an exercise in futility, and (b) most people are not equipped to evaluate the answers in any kind of serious or logically rigorous way.

Paying attention to the micro interactions of a person (or CEO) with others especially those who have no business interest with them can give a good view of their morality. These can be simple things like a conversation they have with random strangers and their judgement on that.

This is a bit like how, when you're starting to date someone new, you should pay attention to how they treat servers and other workers at the places you're going to.

But in the case of interviewing a CEO, you don't often have a chance to see them interacting with random people.

Once you get them in a state where they can't lie, ask directly how trustworthy they are

> Once you get them in a state where they can't lie

How can this be done, and how can you tell when they're in that "state"?

Some of these questions and their purported correct answers are really explaining a few of the odd interviews I've had in the last few years.

I guess in addition to leetcode, one should grind on trolleycar dilemmas as well to get hired as a coder. :)

Nah.

If a company is using leetcode, I won't further consider being employed by that company. Same if I'm given any sort of weird psychological questions.

Not because companies are wrong in doing those things, but because they are a strong indicator of how the company operates in general, and that I would be a poor fit there.

Fortunately, most companies do neither of those things.

I don't think you can really get a grasp of anyone's sense of ethics without actually getting to know them first. There are no magic questions here.

The best you can do is to look at their history and see how they've behaved in the past.

Is being morally trustworthy a clear advantage from shareholders/profit pov? Those are what CEOs of companies are ultimately about regardless of mission/vision/PR of the company.

What's your take on cryptocurrency projects?

"What's your opinion on Effective Altruism?"

If they say anything positive, you know to run the other direction.

What if they aren't really familiar with what that is? I know it's associated with SBF's embezzlement somehow, but if I just heard the term I'd think, "It's gotta be better than ineffective altruism"

Don't ask CEOs, ask the money/capital behind the company.

Good luck getting an answer though.

you have to be a barista for this too work: "You Latte is going to take an extra five minutes to make is that ok?", then you turn around and start chatting in Spanish to your fellow coffee shop employees.

Can you even trust that their answers are candid and what they really think?

Correct. The reason someone gets to CEO is usually because they’re incredibly polished and can convince anyone of anything.

Of course not. But it's possible to catch the dishonest ones in a lie.

"Can people be trusted when they're not being watched?"

There is no question that will truly gauge moral trustworthiness. The most pathological leaders will craft answers that sound "morally trustworthy", but after taking the role will happily take whatever pathological action they please.

If anything, the OpenAI fiasco is more about the disconnect between boards and the companies they guide. It's not the first time I've seen a BoD take action based on information from the wrong people, but the fact that it has been so public makes it a great object lesson for founders and other leaders.

Most sociopaths are extremely competent at hiding in plain sight. They'll say the right thing when necessary. I would try connecting with folks who have worked under them in the past (not folks recommended by the candidate), especially a few levels below, to gauge their leadership effectiveness.

Ask HN:

"How do you feel about unions?"

Part of the problem with CEO's and corporations in general is that they are legally obligated to make decisions in the best interests of their shareholders, which also typically is highly aligned with their own incentives. What looks like an immoral decision from the rank and file POV is highly rational and maybe at worst amoral when considered in their fiduciary context.

Just to clarify, IANAL, but the "legally obligated to maximize profit" is a misinterpretation of Dodge vs. Ford[1]. It was a very radical decision for the time and hasn't been rescinded but still allows executives a wide degree of freedom in decision making. Acting morally is often highly rational and, whether a maximally efficient decision or not, is, IMO, the correct decision - whether there are clear consequences for acting immorally or not.

1. https://en.wikipedia.org/wiki/Dodge_v._Ford_Motor_Co.