Make the Bold Choice: What Improv Teaches Us About Psychological Safety and Leadership
A shoe, a shirt, and a very calm scene partner
There’s always one.
I’ve been facilitating a particular improv exercise (“3 Things”) for decades, and it never gets old. The instructions are simple: “Turn away from your partner and make three bold changes to your appearance that your scene partner will immediately notice.” When they face each other again, they have to point out the changes.
Some participants play it relatively safe. They roll up a sleeve, untuck a shirt, or rearrange their hair. Others get a little more adventurous.
And then there’s always that one person who gets unapologetically bolder than everyone else.
In a recent improv class at Carolina Improv Company, that person was a young man who balanced a sneaker on his head, tucked one arm into his T-shirt, and communicated with the conviction of someone who saw nothing unusual about his appearance.
Across from him stood his scene partner, hands folded, wearing a calm, knowing smile that seemed to say, “Okay. This is our reality now. Keep going.”
The photograph is hilarious. But after decades of watching people participate in this exercise, what fascinates me isn’t just how ridiculous someone is willing to look.
It’s what happens when another person accepts that ridiculousness without judgment.
And that’s where an improv exercise becomes a powerful lesson in leadership, communication, and psychological safety at work.
Why making bold choices matters in improv
In improvisational theater, performers learn to make clear, specific choices that give their scene partners something to recognize, respond to, and build upon.
A tentative choice creates uncertainty. A bold choice creates possibility.
When someone makes an offer with conviction, their partner doesn’t have to waste time figuring out what’s happening. They can focus on what happens next.
That’s why I love this exercise.
Through the years, I’ve noticed something remarkably consistent. People approach boldness differently. Some hesitate, some cautiously test the boundaries, and others throw themselves into the experience without a second thought.
And every time, at least one participant reminds the rest of the room that there’s another level of boldness available.
The lesson isn’t that everyone needs to put a shoe on their head. Instead, the lesson is that most of us are capable of being bolder than we allow ourselves to be.
The exercise also reveals something about human behavior. Even when people are explicitly encouraged to make bold choices, many still instinctively calculate how they’ll be perceived.
Will I look foolish?
Am I going too far?
What will everyone think?
Those questions don’t disappear when people leave an improv classroom and return to work.
The leadership connection: Are your employees playing it safe?
Think about the last time someone on your team suggested an unconventional idea, challenged an established process, or questioned a decision.
Did they communicate confidently? Or did they soften their message with phrases like:
- “This might be a stupid idea, but…”
- “I’m probably overthinking this…”
- “I don’t know if this would work…”
- “Maybe we could consider…”
Those phrases aren’t necessarily signs of insecurity. Sometimes they’re attempts to protect relationships, respect authority, or avoid appearing confrontational.
But they can also signal a workplace where people have learned to minimize their contributions before anyone else can dismiss them.
And that creates a leadership problem.
When employees hold back their ideas, concerns, and observations, organizations lose access to valuable perspectives. Problems remain unspoken. Opportunities go unexplored. Innovation becomes something leaders say they want but unintentionally discourage.
A team that feels compelled to play it safe will rarely produce its boldest thinking.
Psychological safety: The missing ingredient in bold leadership
Harvard Business School professor Amy Edmondson introduced team psychological safety as a shared belief that a team is safe for interpersonal risk-taking.
Her research on 51 work teams found that psychological safety was linked to learning behaviors that helped explain differences in team performance (Edmondson, 1999).
Subsequent research reinforced its importance. A meta-analysis of 117 studies found positive relationships between psychological safety and outcomes including task performance, employee engagement, and information sharing (Frazier et al., 2017).
In practical terms, psychological safety means employees can ask questions, acknowledge mistakes, challenge assumptions, and contribute ideas without fearing humiliation or punishment simply for speaking up.
Now look at that photograph again.
The man with the shoe on his head is making the obvious bold choice.
But his scene partner is doing something equally important.
He’s accepting the offer.
He’s not rolling his eyes, criticizing the choice, or trying to make himself the center of attention. He’s simply present, engaged, and willing to see what happens next.
One person demonstrates the courage to take a risk. The other demonstrates the acceptance that makes taking risks easier.
That’s the relationship leaders should be paying attention to.
What the improv principle of “Yes, And” teaches leaders
One of the foundational principles of improv is Yes, And.
People often misunderstand it as a requirement to agree with everything.
That’s not what it means.
“Yes” means acknowledging and accepting what someone has contributed as the starting point for the interaction.
“And” means building on that contribution to move something forward.
Imagine an employee approaches a manager with an unconventional idea for improving a process.
One response might be: “We’ve already tried something like that. It won’t work.”
Another might be: “That’s an interesting direction. What problem are you trying to solve, and how might we test your approach?”
The second response doesn’t promise approval. It creates an opportunity for exploration.
That distinction matters.
Research by Vera and Crossan (2005) explored the relationship between improvisation and innovative team performance, emphasizing the importance of collaborative behaviors and supportive organizational conditions (Vera & Crossan, 2005).
In other words, encouraging people to think creatively isn’t enough. The environment must also support the behaviors that make collaboration and innovation possible.
Leaders don’t have to accept every idea.
But they do need to consider whether their immediate reactions encourage employees to contribute again.
Three ways leaders can encourage bolder thinking
- Reward the courage to contribute, not just the quality of the idea.
When someone raises a concern, challenges an assumption, or suggests an unconventional approach, acknowledge the willingness to speak up.
Even when the idea isn’t feasible, the contribution can still be valuable.
- Replace immediate judgment with curiosity.
Before evaluating an idea, ask questions that help you understand it, such as:
- “What makes you think this could work?”
- “What are we overlooking?”
- “What would we need to learn before deciding?”
Curiosity creates space for ideas to develop before they’re dismissed.
- Model the behavior you want to see.
Leaders who admit uncertainty, acknowledge mistakes, and share unfinished thinking demonstrate that vulnerability and competence aren’t mutually exclusive.
If you want employees to take reasonable interpersonal risks, show them what that looks like.
And when someone makes a bold contribution, pay attention to how you respond. Your reaction may influence whether they, and everyone watching, feel comfortable doing it again.
The boldest person in the room isn’t always the leader
After facilitating this exercise 100s of times, I still look forward to discovering who will take it further than everyone else.
There’s something wonderful about watching someone abandon the need to look polished, proper, or predictable and simply commit.
But I’ve also learned to watch the other person.
The one who receives the unexpected offer.
The one who decides whether to judge it, resist it, ignore it, or build upon it.
In improv, just as in leadership, boldness may start with one person, but it takes another to make it meaningful.
Here’s a question for all you leaders out there:
When someone on your team makes a bold choice, do you help them build on it, or do you make them think twice about doing it again?
Your team doesn’t need you to put a shoe on your head.
They need to know they won’t regret taking a chance in front of you.
Ready to build a workplace where people feel safe speaking up, thinking differently, and making bold choices?
Through improv-based leadership development, team workshops, and organizational health consulting, Carmine Communications helps leaders strengthen trust, communication, collaboration, and psychological safety.
Let’s talk about creating a team that isn’t afraid to contribute its best thinking. Contact Gina Trimarco at gina@ginatrimarco.com.
