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

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.

"What's your opinion on Effective Altruism?"

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

[flagged]

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

"How do you feel about unions?"

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.

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.

By what standard do you define morality?

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

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.

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.

- "Do you support tech workers unionizing if they choose to?"

- "Should Palestine should be free?"

- "Do Black Lives Matter?"

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.

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.

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.

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.

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.

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?

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.

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.

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.

What's your take on cryptocurrency projects?

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

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.