The game is organized around two activities, drawing a picture and telling a story. In both of these activities, the group will be split into separate teams, with one team given specific time and instructions to plan ahead. After both activities have been completed, the facilitator assesses and leads discussion around the team’s work, and the teams will have a chance to compare their experiences.


30min – 45min

Number of participants

Ideal 6 – 8, enough for two teams of engaged participants.


  • Drawing surface
  • Red, green, and blue markers
  • x1 printed text of “The Jabberwocky” by Lewis Carroll, large enough for the entire team to read. (you could also display it on a tv or projector)
  • x2 printed booklets of instructions. This booklet should have the following instructions printed one per page, in the following order.
  1.  Draw a red square
  2. Draw two green squares and a green rectangle inside the red square
  3. Draw a dog
  4. Draw a triangle
  5. The triangle should be on top of the red square
  6. The dog should be blue
  7. Draw a flagpole
  8. The two green squares should look like windows
  9. The green rectangle should like a door
  10. Draw seven birds
  11. The triangle should be red
  12. Draw some grass
  13. The flagpole should be flying a banner with the 23rd line of the “Jabberwocky” on it


Split the group into two teams, Team 1 and Team 2. Tell them they will be participating in some group exercises, where one team will be given time to plan, and the other will not.

Activity One – Draw Me a Picture!

Tell the teams they will be given a booklet of instructions for drawing a picture. Ask Team 1 to leave the room, and start the activity with Team 2.

Team 2

  1. Tell them they will be given one minute to review the instructions in the booklet, and four minutes to draw the picture.
  2. Hand them the booklet and start the clock on the planning minute. Do not allow them to begin drawing. Observe how they plan and divide up labor. See if they are able to identify that they are drawing a house before they start.
  3. Once the planning minute is over, start a clock for four minutes and instruct them to draw the picture.

After the drawing time is complete, allow the team to step back and discuss their work for a moment or two. Then cover the picture, ask them to leave the room and invite in Team 1. For Team 1, follow these steps:

  1. Tell them they will not be given planning time, but that they will get a bonus minute at the end to make up for it.
  2. Hand them the booklet and start the five minute clock on the drawing time. See if the team naturally plans, or simply barrels right into drawing shapes. Observe if labor is being shared, and if they are having to do rework.

After the drawing time is complete, allow everyone a brief time to catch their breath, and then cover the drawing, invite the other team back, and begin the next activity.

Activity Two – Tell Me a Story!

Tell the two teams they will be doing a five minute literary analysis on a famous poem. This time, ask Team 2 to leave the room, and start with Team 1.

  1. Tell them they will be given one minute to plan a presentation that identifies the hero, villain, and plot of the piece. Start the clock off. Allow them to use whatever material is at hand, including laptops.
  2. After the planning minute, display the Jabberwocky poem and start the timer for four minutes. Do not allow people to use their phones or laptops to look up answers to the questions.
  3. Once the four minutes are up, have the group give you their presentation on the hero, villain, and plot of the poem. In addition to the correct answers, pay attention to the other details the group adds in.

Hide the poem, invite Team 2 in, and repeat the process, this time with no explicit planning time at the beginning but with a five minute clock.


  • You may need to play around with the amount of time the teams get to complete their activity. You want enough time for the planning group to be able to complete their task fairly well, but without going back and refining their work.
  • If you want to make things extra tricky on the picture drawing activity, remove the blue marker from the room. When the team finds out they need a blue marker, either watch them improvise or tell them “blue markers are on backorder,” and deliver them the blue marker a minute after they asked you for one.


You should notice a difference in the two different activities and how the teams handle them. The drawing activity is specifically designed to be trip up people if they don’t read all the instructions first, whereas the story activity is more straightforward. Just like in software projects, sometimes planning is important and sometimes it only provides minor gains, and the team should reflect on these things if possible.

A couple specific questions to ask

  •  What kind of obstacles did you run in to?
  • If a team didn’t plan, ask them why.
  • Did you fully understanding the picture instructions before you started drawing?
  • Did you have to do any rework?
  • Where there any differences between the two activities? Did one require more planning?
  • Does planning lead to better outcomes? Compare the two pictures, and recount the presentations.
  • Can you relate this to an instance in your day-to-day work? Where is planning effective, and where can we roll through things at face value?
  • What kinds of things are causing us delays or rework in our development? How can we better plan for them?

5 thoughts on “To Plan or Not To Plan

  1. The intention of this game is to highlight when and why planning is needed. By abstracting the planning process away from software development, hopefully the group can critically look at their own reactions during the game.

    The first activity requires planning because it is complex. If you don’t plan before jumping in there will be rework, confusion, or wasted effort. The second activity does not require planning because its basically a research task. Spending time polishing a presentation doesn’t add any value.

    Hopefully with a little coaching on your part, the teams can see the different types of activities they engage in, and where they should invest planning time.

  2. Hi Rob, thank you for your contribution on tastycupcakes.
    I had some question about your game.
    Activity 1, Team 2: After planning session you take away the instruction from Team?

    What is the Intention for the two activities?
    Do you wanna show up the difference between structured and unstructered planning?

  3. Give team two all the same instructions as team one, but instead of explicitly telling them to plan and waiting to reveal the poem, show it immediately. The can use their laptops for presentation purposes, if they choose to. My experience has been that team two does a less technical, but no less effective, presentation.

  4. I’m not understanding how team two will know they are giving a presentation based on Jabberwocky. Do I tell them and allow them to use their laptops and phones to research, unlike team 1?

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