Exercise: Interview (or "be Paul Graham")

Example: (participants A and B)
A: I am a gardener.
B: What is a gardener?
A: It's my job.
B: No, what does a gardener do?
A: I maintain gardens.
B: What is an example of a task that you have to do?
...

Description:

2 participants act in roles of the Interviewer and Interviewee. The Interviewer asks questions to be answered honestly, ideally that would tend towards abstract answers like "What do you do for a living?" and "What did you study in school?". The Interviewer repeatedly asks for more specificity, until the responses are at the level of describing particular objects and tasks.

This goes on for a while, then the participants switch roles.

Rationale: Some of the game exercise ideas are great, but they don't seem to demonstrate using the skill in non-contrived situations. So this exercise is intended to overcome that problem by exposing non-(specificity/concreteness) in our actual communication.

I believe that this exercise can be performed between 2 people who have the barest grasp of the concept. While the skill of being specific needs to be learned, the skill of noticing that the other person isn't being specific should be much easier. After observing the game once, anyone should be able to ask some of the right sorts of questions to get the other person to be more specific. And then by repeated iteration, participants should be able to give more specific/concrete descriptions at the outset.

Caveats:

This does depend on the assumption that the skill "Ask for the right level of specificity" is easily / automatically learned.

A list of questions should be developed that are actually answerable for people in different walks of life (unemployed, did not attend school, etc.).

It might be too easy to cheat by being way too specific. But then, if you can do that, you might not need to learn the skill. Example: starting with "I push keys on the computer keyboard with the tips of my fingers, and characters appear on the screen corresponding to what I typed."

Variation:

One person is the interviewee, several people are the interviewers. The interviewee needs to make themselves understood by each of the interviewers. This might help train new interviewers.