The Play Imperative: Rewriting the Corporate Script
Summary
Everyone talks about agility, adaptability, and innovation—but what if one of the most powerful leadership tools is something we already do every day: improv?
In this episode of Conversations in the Future of Work, Rachel Cossar sits down with Amy Warshawsky and Betsy Salkind, coaches and facilitators who use improvisation as a framework for developing communication, coaching, and leadership skills. Their work combines improv, coaching, experiential learning, and mind-body awareness to help people build skills through practice rather than simply talking about them.
Drawing on their backgrounds in coaching, organizational studies, somatic movement, and improv, Amy and Betsy explore how play can become a serious tool for professional development. They discuss why leaders are already improvising every day, how organizations can create environments where experimentation feels safer, and why communication skills become stronger through practice.
How do you pitch the concept of “play” to a rigid, metrics-focused leadership team, and how do you help them realize they are already improvising every day?
For Amy and Betsy, play isn’t the opposite of serious professional development.
It’s a way into it.
Betsy explains that play can help people move out of self-consciousness and fear of getting something wrong and into a mindset where creativity and new possibilities can emerge. Amy adds that even highly structured, metrics-focused leaders already play in other areas of their lives—through sports, music, entertainment, gaming, and other activities. Helping them recognize that connection makes it easier to see how those same qualities can benefit their professional lives.
The goal isn’t simply to make work fun. Their programs intentionally combine play with skills development, creating low-stakes environments where participants can become comfortable, experiment, and then move into deeper learning.
How does shifting our mindset from corporate “agility” to theatrical “improvisation” change how leaders handle workplace uncertainty and real-time decision-making?
Amy makes an important distinction between solving a problem and developing the ability to respond when problems arise.
Corporate agility can become focused on the immediate challenge: What is the problem, and how do we solve it?
Improvisation focuses on developing a way of being that allows someone to navigate change, uncertainty, and unexpected situations as they happen.
Instead of preparing leaders for one specific challenge, improv helps them strengthen the underlying skills and confidence needed to respond to many different challenges. Betsy also points out that improvisation isn’t limited to the theater—we’re all improvising constantly in work and life. The difference is learning how to intentionally access that ability when we need it.
How can organizations practically build psychological safety so employees feel safe enough to experiment—and occasionally fail—on the spot?
Psychological safety begins with the environment leaders create around experimentation.
Betsy explains that their workshops establish a clear structure and set of rules that give participants permission to try things without becoming consumed by the possibility of making a mistake. One of the principles they use is treating mistakes as unexpected outcomes that can become opportunities for learning.
That mindset matters because workplaces can sometimes pay more attention to mistakes than successes. When leaders deliberately create space for experimentation and different outcomes, employees have greater freedom to contribute ideas, take appropriate risks, and learn.
The lesson also has to extend beyond the workshop. Amy emphasizes helping participants identify exactly how they can apply what they practiced to their own teams and workplace challenges, with continued coaching and practice helping those behaviors stick.
In a hybrid world of work, how can professionals use these specific improv-based communication tools to have more meaningful, dynamic conversations?
Hybrid and remote work have reduced many of the spontaneous opportunities people once had to connect, play, and build relationships with colleagues. Amy and Betsy see intentional experiential learning as one way to rebuild some of that connection and sense of community.
At the center of their approach are skills such as listening, responding in the moment, giving and receiving feedback, staying present, and practicing difficult conversations.
Amy emphasizes that communication improves through repetition: the more people practice conversations, the better they become at communicating. These skills help people develop the nuance, listening, and ability to genuinely engage with one another that increasingly distributed workplaces require.
Ultimately, improv isn’t about turning the workplace into a stage.
It’s about helping people become more comfortable with uncertainty, more willing to experiment, more thoughtful about feedback, and more capable of responding to the person and situation in front of them.
As Betsy’s own leadership experience illustrates, even feedback changes when a leader shifts from looking for someone’s shortcomings to asking how they can help that person develop.
Transcript
Rachel Cossar: Hello everyone and welcome to another episode of Conversations in the Future of Work. I’m your host, Rachel Cossar, and I’m really excited to invite two guests on today’s show in a very special episode. I’ll turn it over to them to introduce themselves. Amy and Betsy, welcome.
Betsy Salkind: Thank you.
Amy Warshawsky: Thank you. Betsy Salkind and I work together using improv as a framework for teaching coaching, communication, and leadership skills. We’ve been doing this together for a good five or six years now.
Our backgrounds are a bit varied. Betsy is more of our improv aficionado, and I have a background in coaching and somatic movement. I use mind-body awareness in coaching and in the work that Betsy and I do.
Betsy Salkind: I started out in organization studies and then quit and became a stand-up comic for 20 years, and then got into coaching.
The work we do now, and our great joy, is designing and facilitating experiential learning and growth opportunities. We really feel—and the data backs this up—that when people are having fun, they learn more. When people are actually doing something versus reading, talking about, or watching it, that’s the kind of learning that sticks.
Rachel Cossar: That’s wonderful. We’re obviously all for experiential learning. Typically, experiential learning is focused on that workshop, in-the-moment, human-facilitated component.
At Virtual Sapiens, we’re always curious about what happens next and how we can support that with AI role plays, practice, and feedback.
Betsy, you set us up perfectly for the first topic I wanted to focus on. You’re working with pretty traditional corporations. How do you introduce and win over people’s hearts and minds when it comes to the concept of play, particularly when you’re speaking to people who may be more rigid and metrics-focused in their leadership?
Betsy Salkind: There’s a ton of research showing its effectiveness. It goes beyond play. It’s really about getting into a positive mindset and into a place in our minds and bodies where we’re not self-conscious or thinking, Am I doing this right? Am I going to get punished for doing this?
We move into a space where new things become possible. That’s what every company wants—for their employees to be innovative and creative.
Amy Warshawsky: Many of the leaders who might fit that description are actually playing somewhere in their lives.
Whether it’s sports, entertainment, playing an instrument, gaming, or something from their past, they’re already doing it. When you help them see the parallel and recognize that they can bring some of what they love about those experiences into their professional lives, there’s great benefit.
Rachel Cossar: Do you ever meet resistance from people who say, “That’s my personal life, but this is work, and work is serious”?
Betsy Salkind: We haven’t really encountered anyone who has resisted the idea because it’s never purely play. It’s play with skills development built into the design.
We design specifically for each company and what its team needs. Fun is often something organizations want, especially now that we’re more hybrid and remote and opportunities for fun within groups are more limited.
Amy Warshawsky: People are really looking for community and opportunities to be engaged and involved.
Sometimes people are nervous, so when we’re designing these experiences, we provide structure and create a low-stakes situation. People can come in, get comfortable, realize they can do this, and then move through the experience with less anxiety or resistance.
Rachel Cossar: Let’s shift to agility. How do we move from corporate agility to improvisation? How can the skills used in improv benefit leaders when they’re dealing with workplace uncertainty and making decisions in real time?
Amy Warshawsky: When we talk about agility, we’re often treating the issue as a problem. We have a problem to solve, and we need to be agile to solve it.
With improvisation, we’re talking about a state of being. It’s learning practices associated with being able to improvise in any given moment.
It puts the emphasis less on the specific problem and more on developing the skills and ways of being that enable us to handle shifts and changes in a very fast-paced world.
Betsy Salkind: We don’t really think of it as theatrical improvisation—just improv.
It can apply to anything: music, work, or life. We’re all improvising all the time. The difference with what we do is helping people connect with their ability to call on that skill when they need it and develop confidence that they actually can improvise.
Rachel Cossar: That connects directly to psychological safety. To allow a team to see a challenge as an opportunity, be creative, experiment, push back, and ask “What if?”, there needs to be enough psychological safety for people to do that.
How do you help people take the safety they experience in your workshops and bring it back to their actual teams?
Betsy Salkind: We’re very transparent about everything we’re doing.
We explain the structure, the container, and the rules. These are things people can use at any point.
One of the key ideas is that mistakes can be treated as “happy accidents.” One of the challenges in the workplace is that mistakes are often punished more than good things are rewarded.
Deliberately creating a space where we welcome experimentation and different outcomes can be very helpful. A leader can bring that mindset back to their team, even if the team wasn’t part of the original workshop.
Amy Warshawsky: We also want participants, before they walk away, to think about how they can specifically take this back into the spaces they’re working in and the challenges they’re facing.
It’s taking the conversation one step beyond, “Here’s what I learned today,” and asking, “How can I apply this learning in my specific area?”
That’s also why coaching and ongoing groups can be valuable. They help people continue applying what they’ve learned.
Rachel Cossar: Failure is interesting because many incredibly successful people have also experienced significant failures. Yet people can reach that first failure and think it’s unacceptable or that they shouldn’t continue.
What about younger generations? Do you think younger professionals struggle more with failure or receiving feedback?
Betsy Salkind: There are cultures where failure is already built into the process. Think about sports, for example.
I think companies and leadership are starting to look at failure differently because we’ve been in such a place of fearing failure.
We also teach people how to give feedback and how to receive feedback. Those aren’t things we’re simply born knowing how to do. Feedback can be incredibly helpful, but it can also be destructive, so learning how to give and receive it is critical.
Amy Warshawsky: I think younger people are far more resilient than we give them credit for.
Part of the learning is helping them recognize how resilient they truly are—how they experience failure, get back up, and continue.
Normalizing that process is important. Regardless of the labels placed on different generations, they’re still human beings functioning in a tough world.
Betsy Salkind: That also connects to the person giving feedback.
Most people are already aware of where they’re missing the mark. They may beat themselves up more than you ever could. What people often miss is recognizing what they’re doing well.
Coaching can help by asking people what they noticed, what they learned, and what they could do differently. It turns feedback into more of a coaching conversation.
Rachel Cossar: Giving and receiving feedback are two of the main things we see people practicing on our platform.
The way feedback is delivered has a significant impact on how it’s received. At the same time, people can learn to become much stronger receivers of feedback—to process it, determine what’s valuable, and move forward.
Amy Warshawsky: I love this idea of support and practice.
The more we practice having conversations, the better we get at communicating.
Our larger hope is that by focusing on skills that help people truly be with and communicate with one another, the world becomes a better place. We need skills like nuance, listening, and playing together.
We’re still on the playground as adults. It’s just a different playground.
Betsy Salkind: I have a quick story.
I was once given an employee to supervise who wasn’t at the same level as everyone else on the team. I was essentially cataloging where this person was missing the mark so we could fire them.
My boss told me that wasn’t my job.
My job was to develop them.
That changed everything for me. I started seeing that person in a completely different light, and we ended up with an incredible working relationship.
When the person giving feedback approaches it from the perspective of, “My job is to develop another person,” it changes everything.
Rachel Cossar: That’s a very important perspective and a fantastic place for us to finish.
Amy and Betsy, thank you again for your time, for being wonderful guests, and for the important work you’re doing. And to our audience, as always, thank you, and we’ll see you next time.