Question Dumping

Updated: August 14, 2020


Clear your mind and organize your thinking.




Asking generative questions

Acting strategically


Synthesizing / Validating


This particular workout is specific to the Staying Strategic program. However, it can be used in other contexts, and there are lots of possible variations. See Variations below for more.

We recommend using Google Docs or Microsoft Word for this workout. Put the current date at the top of the document, and style it Header 1 if you’re using Google Docs. If you’d prefer to use sticky notes and a pen, allocate 20 minutes instead of 10 for the question answering step.

Basic Steps

  1. Pick a project. If you’re working out with others, you can each pick the same or different projects.
  2. What are the top of mind questions for you right now, in this very moment? Take five minutes to dump whatever questions are in your head, one question per line.
    • Use up the whole five minutes
    • Quantity over quality!
    • Don’t worry about “good” or “priority” questions
    • Don’t worry about organizing your questions
  3. Review your list for yes/no or multiple choice questions, and rewrite them as non-yes/no questions.
  4. Add a score in front of each question based on how certain you feel you know the answers — 1 (no idea), 2 (some idea), 3 (pretty certain) — then sort them in numerical order.
  5. Take ten minutes to try to answer as many questions as you can. (Take 20 minutes if you’re using stickies and a pen.)
    • I like to start with questions with a score of 3 (i.e. ones where I’m pretty certain I know the answers) to get those out of the way, but you can choose whichever order you’d like
    • For questions with a score of 1 or 2, just offer your best guess. “I have no clue,” is a legitimate answer. If it helps, write down how you might figure out the answer to the question. For example, is there research you can do? Is there someone you can talk to?
  6. Review your answers. If you change your mind on how certain you feel about the answer, update the score.

Congratulations! You finished your workout! Take a breather.

Multiple Repetitions

This workout is helpful in isolation, but it’s even better when you repeat it over and over again. In the Staying Strategic program, we recommend doing this workout twice, then following it with Question Sensemaking workouts, revisiting this workout again about every other week.

If you’re repeating this exercise, don’t peek at what you wrote down previously. This is all about what’s top-of-mind for you in this current moment. It’s okay if you repeat past questions or answers. It can even be helpful by building your self-awareness of where your mind goes in times of stress, which can help remind you of where you need to focus.

Watch Eugene Do This Workout

Eugene Eric Kim (the creator of this website) used his own Staying Strategic program to help him plan the Fall 2020 launch of the Collaboration Gym. This meant doing this and the Question Sensemaking workouts repeatedly. You can watch recordings of him doing the workouts with his audio commentary below:

Question Dumping, First Time

Question Dumping, Second Time

Question Dumping (along with Question Sensemaking), Third Time

Design Notes

At its core, this workout is about taking the time to get your thoughts out of your head and onto paper, where you can do something about them. This simple habit is an effective way of staying clear and managing overwhelm.

What’s different about this workout from, say, journaling or free writing (which are also excellent practices) is its emphasis on questions. Asking good, generative questions is at the core of high-performance work — facilitating groups, acting more strategically, and learning.

Given enough time, most of us can come up with good, generative questions. The challenge is how to train our muscles to do this more frequently and easily, especially in real-time. Dumping the questions in your head, and reviewing and reflecting on which questions are most powerful, helps you build these muscles.


Jelly Helm has an exercise called 100 Questions, where you brainstorm questions until you have 100 of them (either individually or collectively). You then cluster these questions (similar to the Question Sensemaking workout).

You can do this in five-minute iterations or in one single go. If you do this in iterations with other people working on different projects, you can review each other’s questions every few iterations and offer questions for them.

The most important thing to reach 100 questions. If you run out of questions, get silly. Ask questions like, “What should I eat for dinner?”, or, “What is the meaning of life?” This forces you to think outside of the box, which stretches your muscles and elicits more creative thinking. It also helps make sure you’re asking the right questions.