On good questions

When the genie gives you two wishes, you always wish for more wishes. Likewise, when it's our turn to ask questions in an interview, a good question to ask is: "What's a good question?"

Our usual unoriginal questions aren't doing us any favors. "What's it like to work at Evil Incorporated" is a terrible question because it's priming the other person to lie to us or at best give us some curated crap. Requests for information are not the only way to go. Soliciting information is not the only function of a question.

Instead of asking for information, we can sometimes ask for help. "What's a good question" is exactly that. It might make one look like an ignoramus, but it helps us quickly find out if this is the sort of place where help is on the menu.

We never know what's a good question to ask our users, clients, or dates because we don't want uninteresting questions that beget uninteresting answers.

Even scientists and philosophers often ask terrible questions. It's because nobody knows the interesting ones. That's why we talk. A good conversation is not the process of exchanging answers, but rather a collaboration to find good questions.

Finding answers is only difficult in Math because a good equation doesn't help you solve itself. In every other matter in life, we're looking for the question because a good question has built-in clues to the answer.

"Why does this thing not work" is not a good question. "Why does this specific object show this strange behavior under these precise circumstances" might be a great question but it's hard to find. But it's worth looking because it has part of the answer.

So what do we do when we don't know what questions to ask? Asking for help is sometimes a good option. It's not about outsourcing the problem to the helper. It's not about burdening them with our hesitance and perplexity.

A good request for help doesn't even have to include a request. Done right, it sounds like an offer. We can share our motivations, incentives, and goals. We can think out loud, provide context, and reveal where we struggle. This has the effect of pulling in certain people. To the helpful, it's an invitation to participate.

Not everyone is eager to help. But sometimes, some people do. How do we promote that? How do we become more likely to receive help? A good start is by asking for it, instead of running pointless investigations.

In your next interview, don't ask about the company culture or the other person's favorite Tarantino. You can ask for help: "Listen, Tim. Evil Co sounds sublime. But I'm still unsure. I loved my last job but I'm here because things happened. I can no longer do that because I'm this kind of person today. I'm eager for this and anxious about that. Do you think people like me do well around here, Tim?"

In all likelihood, Tim is an asshole. But good riddance. We flushed him out early 🥳. We don't need Tim. What we need is to go where we're going and the way to do that is by figuring out who's eager to help not who has the best answer.