Question Sensemaking

Updated: August 14, 2020


Convert chaos and uncertainty into strategy




Asking generative questions

Acting strategically

Group information hygiene

Working inclusively

Working iteratively


Asking for help

Synthesizing / Validating

Facilitating alignment


This may be the most tedious (at least at first) workout in our toolbox. (Although it can also be kind of fun, almost like playing a video game.) It exercises a lot of different muscles, which may not be apparent until after you repeat this workout several times. It’s also one of the most valuable workouts, which should start to be apparent even after one workout.

Do the Question Dumping workout first (ideally twice) before doing this one.

This workout is specific to the Staying Strategic program and uses this Google Docs template. (Make a copy of it before doing the workout.) In a lot of ways, this is an exercise in using Google Docs. Please be patient with this! Google Docs can be wonky (especially dealing with columns). It will feel like a grind, and it might get frustrating, but it will serve you well down the line.

If you’d like, you can use other tools instead of Google Docs, such as Microsoft Word and even pen and stickies using the Strategy / Culture Bicycle.

If you’re doing this in a group with everyone working on the same project, form a “sensemaking” team with 1-6 people, and do this exercise collectively.

First Time

Make sure you’ve done the Question Dumping workout first and that you’ve created a Question Sensemaking worksheet using this Google Docs template. Make sure your document is in Print Layout mode.

  1. Copy and paste all of your questions and answers from your Question Dumping worksheet into your Question Sensemaking worksheet.

  2. Format your questions in the following way:
    • Make your questions bold. This will visually differentiate your questions and your answers.
    • Highlight the questions (NOT the answers) with a score of 1 in red. (I use “Light red 1.”) Highlight the questions with a score of 2 in yellow (“Light yellow 1”). Highlight the questions with a score of 3 in green (“Light green 1”). This color coding is modeled after a traffic light. You’ll find a legend for these colors in the footer of your Google Docs template.

    • Delete the numerical scores. You don’t need them now that the questions are color-coded.
    • Each question will roughly fall under the following categories:
      • ???? Where are we now?
      • ???? Where do we want to go?
      • ????????‍♀️ How do we get there?

      (See Acting Strategically for an explanation of these categories.) Categorize each question by copying and pasting the corresponding emoji at the beginning of the question. (You’ll also find this legend in the footer of your Google Docs template.) Don’t overthink this. Some of your questions might not naturally fall into one of these categories, or it might fit under multiple categories. You can use multiple emoji if you’d like, but it’s better to keep things simple. If you’re doing this as a group, divvy up the questions and categorize them individually, then review and update them as a group.

  3. Step back and notice any patterns in your colors and your categories.
  4. Sort the questions (and answers) into clusters. If you repeated a question, consolidate it and the two answers, increase the font size to 14, and make sure the score color reflects the current thinking. Keep it simple! If questions could fit into more than one cluster, just pick one. Don’t subcategorize questions. If you’re doing this as a group, do as much as you can individually, then review and finalize together. If different people ask the same question, but with different scores or answers, consolidate the questions, increase the font size to 14, color code it with the lower of the two scores, and note that the answers reflect different opinions.
  5. Give each cluster a title (use the Heading 1 style in Google Docs), and separate the clusters with page breaks. Be creative with your titles! Don’t be afraid to be silly and have some fun.

  6. If you have answers that you feel good about and are ready to mark as THE answer (for now, at least), increase the font size to 14.
  7. Pick up to two questions in each cluster that you think are most important for you to answer. Increase font size to 14.
  8. Finally, create a title page by inserting a page break at the beginning of your document, then insert a table of contents with blue links on your title page. This will give you a high-level view of your clusters. Review your clusters one more time, re-ordering or renaming them if it makes sense.

Congratulations! You have taken your first pass at making sense of your questions. Take a breather!

Multiple Repetitions

If it’s been a few weeks since you’ve done a Question Dumping, we encourage you to do another Question Dumping workout first, then return to this workout.

Now that you’ve taken a first pass at organizing your questions, you can add new questions and answers while continuing to refine your organization.

  1. Spend 5-10 minutes organizing your document. Resist the impulse to answer questions. You’ll have the opportunity to work on them soon enough. If the score of your question has changed, update the highlight color. If you are ready to lift up more answers as THE answer, increase the font size of the answer to 14. If you have new questions, capture them, score them with the appropriate highlight color, add the appropriate emoji, and put the question in the right cluster. If you have a better way of organizing, re-organize questions and clusters.
  2. Spend the remainder of your time answering as many questions as you can, taking a step back to re-organize when it feels appropriate.
  3. After you’re finished, review your document at a high-level. I often take a literal step back so that I can barely read the text, focusing instead on the colors and the questions don’t have answers. What are the patterns? Which sections have lots of one color? Which sections have many answers? Which sections have few answers? What does this say about how you’re thinking about your project? What other approaches might you take the next time you do this workout?

After you repeat this workout two or three times, we encourage you to share it with a trusted peer for feedback. Don’t worry if it’s “not ready”; that’s the best time to get feedback.

You’re also ready to start extracting relevant content into a separate document I like to call “Buckets.” This will essentially be the equivalent of your planning document. I generally start with three buckets:

  • Goals + Success Spectrum. What does Success and Failure look like for your project? Hopefully, you’ve already started exploring these questions. If not, you should start!
  • Action Plan. Roadmap, next steps, and possible experiments.
  • Compass. What are the things that are important for you to remember, but that often get pushed out by things that are more urgent? Put those things here. Be creative with how you express yourself.

Add, remove, and rename buckets as you see fit. When you see something in your sensemaking document that should go in one of your buckets, copy it over.

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 Dumping workouts repeatedly. You can watch recordings of him doing the workouts with his audio commentary below:

Question Sensemaking, First Time

Question Sensemaking (along with Question Dumping), Second Time

Question Sensemaking, Third Time

Question Sensemaking, Fourth Time

Design Notes

First and foremost, the goal of this workout is to build the habit of externalizing our thinking and making sense of it together. When we try to organize the thoughts in our head, we rely on our memory, which is inherently constrained. When we dump our thoughts somewhere where we can see them, then organize them, we are more capable of making sense of the bigger picture, keeping our thinking organizing, and building on our thinking by recognizing patterns and making new connections.

The approach of this workout also enables people and groups to think nonlinearly (which is natural, but hard to follow) while tracking progress linearly. You build your sensemaking document iteratively (thus strengthening your muscles and mindsets around iterations), but the end product — even in unfinished form — tells a story in a more narrative form, which makes it easier to understand and share.

The color coding enables you to track your progress over time (ideally, your question highlighting goes from mostly red, depending on the stage of your thinking, to mostly green over time). When used in groups, it also helps you quickly identify misalignment, which tells you where you need to focus your conversations. You can think of it as a kind of heatmap of the state of your strategic thinking.

The conceptual underpinnings of all of this were inspired by Dialogue Mapping, which was invented by my mentor, Jeff Conklin.