100 Questions

Updated: August 20, 2015


Practice thinking in questions.




Asking generative questions


  1. Pick a project. If you’re working out with others, you can each pick the same or different projects.
  2. Take five minutes to write down all of the questions that come to mind about the project. If you’re working out face-to- face, write each question on a sticky. If you’re working out remotely, used a shared document that you both can edit at the same time (such as a Google Doc). This exercise is about quantity, not quality, so just write, don’t edit.
  3. Take a minute to cluster your questions.
  4. Repeat the question brainstorming and clustering process at least one more time. The best way to do this exercise is to keep repeating until everyone has at least 100 questions if everyone is working on different projects or until you have a combined 100 questions if everyone is working on the same project.
  5. If you’re working out with two or more people, share your questions with your partner. Count the number of Yes / No questions, and (with your partner’s help), rewrite them as non-Yes / No questions.
  6. Identify (with your partner’s help) 1-3 questions that will help you move forward with your project.

Design Notes

Asking good, generative questions is at the core of high- performance work — being strategic, being facilitative, synthesizing what we hear, and learning.

Given enough time, most of us can come up with good, generative questions. The challenge is how to embody this muscle so that you are always thinking and listening for the right questions.

100 Questions gives you that time. All it takes is a few iterations before coming up with new questions is challenging. This forces you to think outside of the box, which stretches your muscles and also elicits more creative thinking.

If you combine this with time to reflect on which of your questions are most powerful, you also enhance your muscles for asking good questions.


  • After two iterations,do an additional iteration where you review your partner’s questions, and brainstorm questions for her or his pile. Then switch back, and continue.