practicing awkward questions

When you enter certain situations, it’s likely that you will be asked awkward, painful, or intrusive questions. It’s sometimes worth preparing yourself ahead of time to deal with those questions so they have less power to derail you in the moment.


Some examples of situations in which this kind of preparation might be helpful:

  • Interviewing for a job in which you’re uncertain of your qualifications
  • Interviewing for a job when you expect to be perceived as incapable because of your age, disability, race, gender, etc
  • Presenting on a topic related to justice, particularly if people are likely to try to get you to ~tell your story~ instead of talking about the issue
  • Pitching a business idea for a new type of product
  • Coming out
  • (any number of other things)

It’s worth preparing because:

  • There are two problems you’re facing:
  • One is that it might feel horrible to be asked certain questions
  • The other problem is that answers to your questions will be used in a way that hurts you
  • It can be tempting to avoid thinking about these questions, because it hurts to anticipate them
  • But that can actually make the questions hurt more, and it can make it harder to protect yourself from the practical consequences of answering the questions
  • If you can make the thought of answering (or deflecting) the questions bearable, then they have a lot less power to hurt you, and you have a lot more power to choose how to respond

One way to prepare is to do a practice run with a friend, where they ask you the questions you’re afraid that you will be asked.

  • One really good way to make the questions bearable is to have someone you trust ask you the questions you’re afraid of being asked
  • That can allow you to practice hearing the question and finding it bearable, and still being ok
  • It can also allow you to practice finding answers, and experimenting with which ones seem most effective.
  • If you’ve had some experience hearing those questions, answering them, and still being ok, it can make it a lot easier to answer them when the answers are immediately important

Writing down your thoughts can also help:

  • It might help to make a list of questions you’re afraid of being asked
  • And thinking through what kind of response you might want to make
  • Any way you can think about it ahead of time is likely to be helpful
  • (That said, be careful about scripting too much if you can avoid it. Words that you generate at least somewhat in the moment are often received better than memorized scripts.)

tl;dr If you’re likely to be asked difficult questions, it’s worth practicing answering them. Two things that work well are having a trusted friend ask you those questions, and writing down thoughts.