Company retreats can feel like a recipe for awkwardness: forced team-building exercises, long meetings, and the pressure to be "fun" on command. But here's what retreat planners don't realize: drawing games for company retreats are a game-changer. They're inclusive (no artistic skill required), they work for any group size, and they naturally create the moments of genuine connection that make retreats memorable.
Whether you're planning an in-person retreat, a virtual gathering, or a hybrid event, drawing games provide the perfect format for authentic team bonding. In this guide, I'll share 7 proven activities, strategies for running them smoothly, and how to choose the right game for your specific retreat setup.
Before we dive into specific activities, let's talk about why drawing games outperform traditional team-building exercises at retreats:
1. No Artistic Skill Required This is the game-changer. Drawing games level the playing field. Your best artist and your worst doodler are equally likely to produce hilarious results. This removes the intimidation factor and lets everyone participate without fear of judgment.
2. Immediate Laughter & Connection Unlike trust falls or problem-solving exercises, drawing games generate spontaneous laughter. That shared humor creates genuine bonding--the kind that carries back to the office.
3. Works for Any Group Size From 8 people to 200+, there's a drawing game format that works. You can run simultaneous games in breakout rooms or manage large groups with tournament-style competitions.
4. Bridges Remote, Hybrid, and In-Person Teams The same games work whether your team is sitting together, joined via Zoom, or split across locations. This consistency is invaluable for hybrid companies.
5. Requires Minimal Prep No materials to order, no complex setup. Most games need only paper and pen (or a digital whiteboard). This means you can add drawing games to your retreat schedule without logistical headaches.
What It Is: A drawing-based version of the telephone game. Person A draws a prompt. Person B guesses what they drew and draws their guess. Person C guesses Person B's drawing and draws it. The results? Hilarious, and they teach a lesson about communication breakdown.
Why It Works: People laugh at how a simple idea evolves into something completely different. This creates a natural discussion moment about workplace communication challenges.
Setup for Retreats: In-person groups sit in circles. For virtual retreats, use a shared digital whiteboard and pass drawings round-robin. Works perfectly on mobile devices at hybrid events.
Time Needed: 15-20 minutes
What It Is: Pairs sit back-to-back. One person (the describer) has an image and describes it using only words. The other (the artist) draws based solely on the verbal description without seeing the original.
Why It Works: It directly tests communication and active listening. The differences between the original and the drawing highlight how much we miss in workplace communication.
Setup for Retreats: Use simple images (animals, objects, buildings). For large groups, divide into pairs and run multiple rounds. Virtual version: one person screen-shares the image, the other draws in their own window.
Time Needed: 10-15 minutes per round
What It Is: Each person draws one section of a large figure (head, body, legs) without seeing what others drew. The paper is folded so only a small guide mark is visible. When revealed, you get a hilariously mismatched creature.
Why It Works: It shows how individual contributions combine into something larger. Perfect metaphor for teamwork. Plus, the results are always absurd and funny.
Setup for Retreats: Pre-print large paper or use Miro/Figma for virtual versions. Small groups of 4-6 work best. Instant mobile-friendly play on tablets at in-person events.
Time Needed: 10-12 minutes
What It Is: Classic Pictionary, but faster. Teams race to guess drawings within a short time limit (30-60 seconds per drawing). The pressure creates chaos and laughter.
Why It Works: It's competitive without being toxic. The fast pace keeps energy high. Perfect for retreats that need an energizer between longer sessions.
Setup for Retreats: Divide into 2-4 teams depending on group size. One person draws while their team guesses. Rotate drawers each round. Works seamlessly on mobile, tablets, or projected screens.
Time Needed: 15-20 minutes
What It Is: Small groups draw a shared theme (e.g., "What Success Looks Like," "Our Company in 2027," "The Perfect Workday") together on one canvas. Everyone adds elements. No predetermined plan--it evolves organically.
Why It Works: Reveals how team members think about shared goals. Creates a physical artifact that represents collective vision. Deep team-building disguised as fun drawing.
Setup for Retreats: Use large paper at in-person events or Figma/Miro for virtual retreats. Assign 3-5 people per group. Set a time limit (15-20 minutes) and let creativity flow.
Time Needed: 20-25 minutes
What It Is: Everyone draws an everyday object (coffee mug, laptop, tree) without looking at their paper. The disconnect between intention and result is guaranteed to be funny.
Why It Works: Zero pressure. No competition. Just pure, absurd results. Perfect for teams that are new or uncomfortable with group activities.
Setup for Retreats: Everyone gets paper and pen (or a digital canvas). Announce the object. Draw for 30 seconds without looking. Reveal. Laugh. Repeat with new objects.
Time Needed: 5-10 minutes
What It Is: Teams get a fun, fictional design challenge ("Design a pizza box for astronauts" or "Reinvent the office coffee maker"). They have 10-15 minutes to sketch solutions, then present their ideas.
Why It Works: Taps into creative problem-solving. Shows how visual thinking can generate ideas faster than discussion. Particularly powerful for product and engineering teams.
Setup for Retreats: Present the challenge verbally. Give each team paper or access to a shared digital whiteboard. Set a strict time limit. Present and discuss.
Time Needed: 20-30 minutes (including presentations)
Materials You'll Need: Paper, markers/pens, tablets (optional). A projector for scoring/timing if you want to make it more competitive.
Setup Tips:
Tools You'll Need: A shared digital whiteboard (Miro, Figma, Google Jamboard, or dedicated drawing game platforms). Zoom or Teams for the group connection.
Setup Tips:
The Challenge: In-person and remote participants playing together requires intentional design.
Solutions:
Opening (First 30 Minutes): Use a quick icebreaker like Blind Drawing. Gets laughter, lowers anxiety, sets a fun tone.
Mid-Morning Energizer (10-15 Minutes): Run Speed Pictionary. Breaks up lecture-y content with competitive fun.
Post-Lunch Lull (20 Minutes): Pictionary Telephone or Collaborative Exquisite Corpse. Fights that post-lunch slump naturally.
Late Afternoon (30 Minutes): Theme-Based Drawing or Design Challenge. Uses creative energy when attention is waning but teams still have gas in the tank.
Evening/Social Hour (Ongoing): Have drawing games available as optional activities. Low-pressure option for people who want to bond in smaller groups.
1. Mix Team Compositions Don't always put departments together. Cross-department pairings and teams create unexpected connections.
2. Have a Scoring System (Optional) Not everyone's competitive, but many are. Simple point systems or "winners get first pick at dinner" adds stakes without pressure.
3. Document the Fun Take photos of drawings and share them in a post-retreat email or Slack channel. Creates lasting memories and extends the bonding.
4. Pair with Pro Features for Large Groups If you're hosting 50+ people, look for platforms that support large-scale games. Some drawing game platforms offer Pro tiers with tournament modes perfect for big retreats.
5. Set Clear Ground Rules "Keep drawings appropriate," "No real artistic skill required," "Laughter is the goal." This removes ambiguity and keeps the vibe inclusive.
Let's be honest: many team-building activities feel forced. Trust falls, scavenger hunts, and icebreaker questions often make people uncomfortable. Drawing games are different because they:
A drawing game might seem like a small retreat activity. But the moments of connection--the shared laughter, the "aha" moments about communication, the surprise discovery that your quiet engineer is hilarious--those are what people remember months later.
Here's your simple action plan:
1 Week Before Retreat: Choose 2-3 games from the list above that match your group size and setup (in-person, virtual, or hybrid).
3 Days Before: Test any digital tools you'll be using. Verify everyone can access them.
Day Before: Brief your facilitators on the rules and timing for each game.
At Retreat: Launch your drawing games with clear instructions and an energetic facilitator. Let the fun unfold naturally.
After Retreat: Share photos of the drawings and gather feedback on which games landed best.
Company retreats are an opportunity to build genuine team connection--but only if you choose the right activities. Drawing games for company retreats aren't just about having fun (though they absolutely are). They're about creating moments where people see each other differently, where laughter replaces awkwardness, and where collaboration becomes natural.
Whether you run Speed Pictionary, Pictionary Telephone, or theme-based collaborative drawing, your team will feel the difference. No forced icebreakers. No complicated logistics. Just genuine connection.
Ready to transform your next retreat? Start with one drawing game and watch how quickly your team's energy shifts. The best part? Works perfectly on phones, tablets, or computers--no matter where your team is gathering.
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