Asking Good Questions

November, 2024


There is no such thing as a "good" or "bad" question, only genuine and manipulative questions.

Upon asking a question, if I am curious about the answer, it is a genuine question. Otherwise, it's manipulative.

As a 14 y/o, I used to schedule meetings with random industry professionals I found on LinkedIn. I would search "Software Developer", open a few profiles, and send them a message asking if they would be willing to have a call. After hearing back, if they were interested, I would then investigate their profiles deeply and compile a list of "good questions" to ask on our call. My intention with these questions were not to have a discussion, but instead to leave an impression so I would be remembered. Embedded in my questions were signals that I had investigated their profiles and read their blog posts, but that I still wanted to know a bit more.

I followed the same process when attending conferences. I would approach conversations with the idea that if I ask enough good questions I would leave a lasting impression.

I did this to build my network.

Fundamentally, I was asking manipulative questions. I didn't care about the answers, I just wanted to be remembered.

Now that I am older, my methods of "networking" have changed in two major ways.

  1. I only reach out to people I actually want to talk with
  2. I only ask genuine questions

When I finish reading a book or research paper, if I have more questions, I'll often write an email to the authors. This email is very simple -- I tell them where I found them, thank them for writing the piece they've written, and then I ask my questions.

If I'm genuine with my questions, a simple email exchange often suffices. An email exchange will never satisfy a manipulative question.

I've stopped caring about whether my questions are open-ended.
I've stopped caring about if my questions lead to the other person talking more about themselves.
I've stopped caring about asking "good" questions.

I only care about whether I'm asking genuine ones.