Best and Worst

Choose this exercise

Purpose: Prompt brief personal storytelling across a group using participant-generated superlative questions.

Use it when: Use at the beginning of a meeting, workshop, or retreat when a group needs a fast, low-stakes conversational warm-up with clear personal boundaries.

Skip it when: Skip when the team is in acute interpersonal conflict requiring formal mediation rather than a casual icebreaker, or when participants lack common conversational boundaries.

Group arrangement: Single circle of 4 to 8 participants. For groups of 9 to 24, split into parallel subgroups of 4 to 8.

Timing: SessionLab lists 10 to 15 minutes for 5 to 10 participants. With 8 minutes allocated to sharing, a single circle of up to 8 people fits cleanly at 1 minute per speaker.

Materials and tools

• Two blank slips of paper per person for in-person groups
• One writing pen per person for in-person groups
• One hat, bowl, or container per subgroup to hold paper slips
• One timer for the facilitator
• Shared digital whiteboard or document for remote or hybrid delivery

Before participants arrive

1. For in-person: place paper slips, pens, and one central container on each table or in the center of the circle.
2. For remote or hybrid: set up the shared digital whiteboard with designated columns for Best and Worst questions before starting.

Say this to open

We will do a quick round called Best and Worst. Everyone will write down two questions: one asking about someone's best experience with a topic, and one asking about someone's worst. We will pool them, draw two at random, and answer them. Keep your prompts light and safe for work.

How to run it

1. Write superlative questions 3 minutes

   Say the opening script. Distribute paper slips and pens (or direct participants to the digital board). Ask each person to write one 'best' question on slip one (for example: 'What is the best recipe you know?') and one 'worst' question on slip two (for example: 'What is the worst trip you have ever taken?'). Instruct participants to keep topics light and work-appropriate.

2. Pool and draw slips 2 minutes

   Collect all slips into the central container. Shake or stir the container to mix them thoroughly. Pass the container around the circle. Each participant draws exactly two slips at random. If anyone draws their own question, they may keep it or swap it for another slip from the container.

3. Share answers 8 minutes

   Start the timer. Go sequentially around the circle (or across breakout groups of 4 to 8). Each person reads their two drawn questions and answers each with a brief response. The facilitator monitors the timer to give each participant about 1 minute total (30 seconds per question). Participants may swap a slip with the central pool or pass without penalty.

4. Debrief 2 minutes

   Ask the room: 'Which question in the pool was the most unexpected to answer?' and 'What did you learn about someone else that you would not have guessed?' Call on 2 or 3 volunteers to respond before closing the activity.

Debrief questions

• Which question in the pool was the most unexpected to answer?
• What did you learn about someone else that you would not have guessed?

Finished output: A completed round where every participant has answered two peer-generated questions or exercised a pass option.

Remote

Use an online whiteboard with two columns labeled 'Best Questions' and 'Worst Questions'. Each participant adds one hidden or flipped sticky note to each column. The facilitator shuffles the positions and numbers them. Participants take turns calling out two numbers, revealing those notes, and giving their answers verbally or in chat.

Hybrid

All participants, including those in the room, connect to a shared digital whiteboard or online spreadsheet on personal devices. In-person and remote participants post their questions to digital sticky notes. The facilitator shuffles the digital notes or numbers them, and participants take turns selecting two unrevealed notes to read and answer. Alternate turns between remote and in-room participants.

Access and participation choices

• Participants may choose light, everyday topics and decline intimate disclosures.
• Anyone may swap a drawn question from the remaining pool or decline to answer by stating 'pass' with no explanation needed.
• Participants who prefer not to speak aloud may write their responses on sticky notes or post in chat for a peer or facilitator to read aloud.

If the session gets stuck

A participant submits an overly personal or sensitive question.

Remind the room before drawing that questions should stay light and safe for work. If an uncomfortable slip is drawn, offer an immediate swap from the pool with no questions asked.

Stories run long and threaten the schedule.

Use the facilitator timer visibly and cue speakers gently at the 45-second mark so each speaker finishes both questions within 1 minute.

Terms used here

• Superlative question: A question structured around extremes, specifically asking for a 'best' or 'worst' example of an experience or topic.