Better Questions

Note to future self…

For a while now I’ve been wanting to write a post on the importance of asking better questions but I’ve postponed doing so several times because I don’t have a basic framework to use a starting point and heck I don’t even know what would be the purpose of the post. Nevertheless, here’s my initial attempt at figuring out how and why we should ask better questions.

Ironically I think the best way to get started is by asking two simple questions:

  1. Why are great questions valuable? Most problems in life can be solved by asking the right question. In all likelihood, someone in the world has the answer to your questions. If you assume these factors to be true, then asking the right questions is one of the best cognitive tools in your arsenal.
  2. What factors inform a good question? Factors might include but are not limited to:
    1. Potential for insight: how likely is that the answer to this potential question will yield significant insight to you?
    2. Order of operation: questions are usually asked sequentially so some questions might only make sense if they’re asked before or after another question.
    3. Ease of response: how likely is the respondent can answer that question quickly while still providing valuable insight.

Here are some other quick notes on good questions:

Types of Questions

  1. Factual: these are questions that have one right or factual answer. For example, what’s the speed of gravity?
  2. Argumentative: these are questions where there might be many correct answers or where the answer might be expressed in terms of likely it is to be correct. The strength of the answer will depend on how the strength of the respondent’s argument. What is the best career for someone graduating from college?*
  3. Preferential: these are questions with a specific answer that will vary depending on who you ask. These are different than argumentative questions because for these types of questions the only input that matters is the preference of the responder. For example, do you prefer a vacation in the mountains or on the beach?

*This leads me to believe that the strength of question lies in what it’s trying to optimize for.

Best Practices

  1. Avoid asking binary questions (questions that can only be answered with a yes/no) because this limit the insight you can derive from asking a question.
  2. Avoid interruptions. Again order of operations matters and the answer to one question might lead to an even better follow-up question. Let things play out.
  3. Avoid leading questions. The way you frame a question will influence the answer you get. Don’t ask questions just to confirm your what you believe is the right answer to that question.


I’ve definitely gone down a rabbit hole with this post. I am not even scratching the surface and it’s evident that I am already out of my own depth here. Asking good questions is a skill that takes time to master because there are so many factors to consider. Nevertheless, I think the next steps for me is to keep thinking about the relationship between messenger and receiver of a question and how to maximize the insight that you can derive from the questions that you ask.

That’s it for now. I will report back with any updates.

Now back to work…