Improv workshops for teams · Chicago & on-site anywhere
The most useful two hours your team will spend laughing.
Hands-on improv workshops that teach teams to listen harder, build on each other's ideas, and stay steady when the plan changes. Founded and led by Charles Curren: ten years on Chicago stages, trained at iO, The Annoyance, and The Groundlings.
No stage. No spotlight. Nobody has to be funny.
Founder Charles Curren (top right) with his Chicago improv team.
01 · Why improv
Improv isn't a stunt. It's a set of habits every team needs.
Every team improvises: in the client call that goes sideways, the brainstorm that stalls, the meeting where nobody says the obvious thing. Improvisers just practice it on purpose. Here's what your team walks away with.
Listening that changes the answer
You can't plan your next line and hear your scene partner at the same time. Same goes for meetings. We practice the kind of listening that makes people feel heard and makes the next idea better.
“Yes, and,” the real version
It doesn't mean agree with everything. It means take what's offered and add to it. Teams that do this brainstorm faster, hand off cleaner, and spend less time arguing about who was right.
Comfort with the unplanned
Speaking up, thinking on your feet, recovering when something flops. Improv makes failing cheap and fast, so people stop being afraid of it back at work.
“Yes, and” means making others feel seen, and giving them additional energy to build off of.
02 · How it works
What a session actually looks like
Every workshop starts with a short call about your team and what you want out of it. From there, a typical two hours runs like this.
Warm up, everyone at once
Simple whole-group games. Nobody's watching anyone, because everyone is too busy playing. This is usually where the skeptics turn around.
One skill at a time
Exercises in pairs and small groups that isolate a single habit: listening, agreement, letting go of the plan. Low stakes, lots of laughing.
Scenes about real work
Always in groups, always optional. We put the skills into situations your team recognizes: the messy handoff, the stalled brainstorm, the client curveball.
What comes back Monday
We name what just happened and connect it to how you actually work together. You leave with two or three things people will use this week.
What you'll need
- A room with space to move around
- Chairs pushed to the walls
- Six to forty people
- Zero experience
That's it. Charles brings the rest.
03 · Formats
Pick a format. We'll shape it around your team.
The Energizer
60–90 minutes · up to 40 people
Open an offsite, wake up an all-hands, or give a retreat its shared high point. Fast, fun, and aimed squarely at connection.
The Workshop
2–3 hours · 8 to 24 people
The full experience: listening, “yes, and,” and working the skills into real situations. For teams that want something to keep. They'll have a great time anyway.
The Series
4–6 sessions · same team
Habits stick when you practice them. Weekly or monthly sessions that build on each other, plus custom tracks for leadership, sales, and presenting.
Flat rates, no per-head surprises. Workshops start at $1,500. Travel outside Chicagoland quoted separately; virtual sessions available for distributed teams.
04 · About
Who's running this thing?
I'm Charles Curren, and Sidecoach is my company. I've spent the last ten years on Chicago improv stages, more than 300 shows, and eight of those years training at the theaters that built the form: iO, The Annoyance, and The Groundlings in Los Angeles. I still perform most weeks with teams around the city.
Here's what all that stage time taught me: the things that make a scene work are the things that make a team work. Listening. Committing. Making your partner look good. Stepping outside your comfort zone is genuinely fun when the room feels safe and someone's steering. Building that room is the job.
I'm not here to turn anyone into a comedian. I'm here to make your team better at being a team, and to make sure they have a great time doing it.
Charles Curren · founder, Sidecoach
For whoever's reading this thinking, “absolutely not.”
Introverts do great here.
Improv rewards listening, not volume. The quiet people in the room are usually the best scene partners, and they often get the most out of it.
Nobody performs alone.
Every exercise is in pairs or groups, and it's always fine to sit one out. There's no stage and no audience. Just your team, in a room, playing.
Nobody has to be funny.
The games are funny. You just have to show up and play them honestly. The laughs take care of themselves.
05 · Questions
The things people ask before booking
Do we need any improv experience?
None. Everything is designed for people who have never done this and would rather not. If your team has a few theater kids, great. They won't dominate the room.
What size group works?
Six to forty is the sweet spot for one facilitator. Bigger event? Let's talk about format. A shorter, high-energy session scales up well.
Where do sessions happen?
Your office, offsite venue, or a conference room, anywhere in Chicagoland with no travel fee. Charles travels nationally, and virtual sessions work well for distributed teams.
Is it work-appropriate?
Completely. Ground rules are set up front and the content stays clean. Nobody gets singled out, and nobody's put on the spot.
What do you need from us?
A 15-minute call beforehand, a room with space to move, and an honest sense of what you want your team to get out of it.
How far ahead should we book?
Two to four weeks is typical. Shorter notice is often possible. Just ask.
06 · Book
Let's find a date.
Tell me a bit about your team. You'll hear back within one business day with a few options and a flat quote.
Got it
Thanks. You'll hear from Charles within one business day.
In the meantime, the only homework is to not do any homework.