Asking useful questions

Sun Jan 9, 2022, 553 Words

In this post I explain why some questions are more useful than others, and how to ask better questions. Asking excellent questions is an important skill that improves the outcome for anything you work on. The best questions are specific, leverage existing mental models, yet force you to think beyond what you currently know by evaluating problems from different perspectives.

How do good questions improve the outcome for anything you work on? Good questions cause us to rethink what we believe about a situation, while the best force us to examine how we came to hold those beliefs. Rethinking what we believe involves investigating how we came to hold those beliefs in the first place. Inevitably, that means identifying what we know to be true - the facts of the situation, which are indisputable no matter the perspective - and our interpretations, assumptions, and inductions based on those facts. Once facts and their derivatives have been identified, it’s much easier to incorporate new information or update assumptions that are unsound following closer scrutiny. This process is akin to mentally editing yourself, just like how you self-edit documents you’re writing before publishing them. As in writing, self-editing via rethinking almost always results in an improved product.

Good questions relate directly to the concern at hand, yet are specific enough to trigger rethinking or exploration. If I’m holding a 1:1 with someone, asking them “What have you been up to?” is a bad question if I’m looking to learn more about their state of mind. It is both vague and doesn’t relate to the concern at hand, so it’s unlikely to elicit relevant information. On the other hand, asking a friend I haven’t seen recently the same question is a good question because it is relevant to the current concern - namely, updating my knowledge about my friend’s life. Going back to the 1:1, a more direct and specific question like “What is on your mind right now?” is far more likely to provide relevant information because it is both highly specific to my concern - understanding what’s on their mind.

The best questions go a step further than relating to the concern at hand, they cause us to consider what we already know from alternative perspectives. No matter how much we try, availability bias means your initial read of a situation is based on what comes to mind easily, not necessarily what’s most rational. Meanwhile, our totalitarian ego causes us to instinctively resist changing our mind, discounting information that clashes with our perspective and emphasizing information that confirms it. Sticking to easily-available snap judgment probably isn’t the optimal way to make decisions. Thankfully, we have a secret weapon. Questions can gracefully pull us back from an initial interpretation and promote rethinking the situation. For example, after finding yourself upset at something small, asking “Is my reaction proportional to the problem?” will prompt you to rethink the problem and your reaction. In Richard Feynman, “… you must not fool yourself, and you are the easiest person to fool.”

You should now have an understanding of why some questions are more useful than others, and how to use questions to improve whatever you’re working on. Ask specific questions that leverage your existing mental models. And guard against your cognitive biases by asking questions that promote rethinking.