Ben Winter of SuccessImprov: “How Improv can create a fantastic work culture”

Jason Malki
Authority Magazine
Published in
8 min readMay 7, 2020

I believe improv should be taught in schools as a required course. And not just stage improv. Yes it needs to be improv for stage as that is the easiest way to learn, but it needs to be taught in real life scenarios. How to relate it to life, family, business, and self. The level of confidence that comes from learning improv and implementing it into everyday life, is transformative.

As a part of my series about about how leaders can create a “fantastic work culture”, I had the pleasure of interviewing Ben Winter of SuccessImprov.com and FunTeamBuilding.us.

Ben sees the world as one big stage and everyone is improvising. What most people don’t understand is that there are rules in improv. When following these rules, everything works better. Ben has put this thought into action with his company, Success Improv.

Thank you so much for doing this with us Ben! Can you tell us a story about what brought you to this specific career path?

Through years of personal growth, improv training and performing, and owning several businesses it became clear that improv isn’t just for stage. It is a way of life. It was only a matter of time before I put all of the pieces together to provide a system for businesses to use to enhance their culture, innovation, team work, and so much more.

Can you share the most interesting story that happened to you since you began leading your company?

One of the most interesting aspects of business is the human interaction. We all assume that people will work well together without even setting those expectations. When we sat everyone down and started to share the expectations we had of each other we all realized how off we were about what we thought people wanted. We started communicating and effectively communicated our expectations of ourselves, the company, and others we work with. This level of communication is invaluable in any relationship.

Are you working on any exciting projects now? How do you think that will help people?

We are building an advanced level training with additional rules of improv. To extend the skills that are shared with the basic levels of improv. This will help further team building, innovation, and communication with ourselves and others.

Ok, lets jump to the main part of our interview. According to this study cited in Forbes, more than half of the US workforce is unhappy. Why do you think that number is so high?

Expectations. “The only reason anyone gets upset is because an expectation hasn’t been met.” — Ben Winter (Yes, I said that and I quoted myself). It sums up why people are upset. What most people don’t realize about expectations is that most of them are unknown until the person gets upset. If they would just stop and look at why they are upset they will realize that they had an expectation. An uncommunicated expectation is unknown to everyone. If nobody knows about what you wanted, how can you be upset with them? They didn’t know. Until you know your expectations, communicate them, and have buy-in by others, there is no reason to be upset.

Based on your experience or research, how do you think an unhappy workforce will impact a) company productivity b) company profitability c) and employee health and wellbeing?

As a former unhappy employee I can tell you that an unhappy employee will do the bare minimum to not get fired. This directly affects profitability. And of course, anyone who is unhappy usually has more stress and stress is simply dis-ease (disease). Sickness. Which furthers the effect on profitability.

Can you share 5 things that managers and executives should be doing to improve their company work culture? Can you give a personal story or example for each?

Acceptance. Perception. Expectations. Awareness. Trust.

These five things correlate directly to the first five rules of improv.

Acceptance is simply the nature of accepting what is. You have to know, acknowledge, and accept your point A. Where things are now.

As for a personal example, micromanagement. Until I saw that I was micromanaging people, there was no chance to change anything. Step number 1 was simply accepting that I was doing what I didn’t want to be doing.

Perception is a big problem in our society today. Just turn on the different news stations and see how differently they see the same issues. As the saying goes, “You can’t understand someone until you’ve walked a mile in their shoes.” This is simply about looking at all of the different perspectives within your company.

Once I was able to look through the eyes of my employees I could see how micromanagement affected their morale.

Expectations, as previously stated, when not met is the only reason anyone gets upset. As managers and executives we all have expectations of the company, the employees, of everyone and everything. Anyone who says they try not to have expectations is an expectation in and of itself.

As a manager I had many expectations and I thought that the only way to meet those expectations (known or unknown) was to tell everyone how to do everything. It sucked my time, my energy, and I was always left upset anyway.

When I shared my expectations, when I heard my employees’ expectations, and we met in the middle, negotiated, and discussed things, we were able to come to agreements and understandings previously unthinkable. And in a good way.

Awareness is a big step in this whole process. You need to become aware enough to see you are upset, take a step back, and see if you are upset because of a previously stated expectation or a new one that wasn’t previously known. This is also awareness to see that someone else is upset and to have open communication about why.

I had enough training to be aware of my surroundings. Improv alone is an amazing tool to stay present. This allowed me to see that there was a problem and look for a solution that would help everyone, not just assume the problem was with my employees. It takes everyone to solve a problem thoroughly.

Finally, trust. While nobody should have blind trust of people, things, and situations, they should ultimately trust themselves. Trust that if they are taking the right steps, they can help resolve most situations even if the other person isn’t doing their part to solve the problem.

When I stopped micromanaging I had to trust that it was the right thing for me and for my employees. I had to trust that they were hired to do a job and that they would do it well. I had to trust that even if it wasn’t done my way it was still getting done and would likely be done better.

It’s very nice to suggest ideas, but it seems like we have to “change the culture regarding work culture”. What can we do as a society to make a broader change in the US workforce’s work culture?

This is the trick isn’t it? This comes back to the above. We have to accept that there is a problem, change our perception on where the problem stems, understand that we have to start with ourselves and change our own expectations, be aware of what others want and their reactions to our changes, and trust it is the right move.

Plenty of people have done the research into the “40-hour work week” and its effectiveness or lack thereof. We see stories, statistics, research about better ways, yet so many people are stuck with their perspectives and expectations that they couldn’t possibly trust there is a better way.

To change society we must first change ourselves. After enough people do that, society will have changed right along with us.

How would you describe your leadership or management style? Can you give us a few examples?

My leadership style has changed since incorporating improv into my everyday lifestyle. I listen more. I stop myself when getting upset. I communicate my expectations more clearly. I support others in sharing their expectations. Even if you are the “boss” you can treat people equally. And when those around you feel valued, they become loyal, friendly, and fun.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

It isn’t just one person. I mean, if I had to choose one person it would be me, myself, and I. I was the only constant along my path. There are people, organizations, friends, coworkers, colleagues, family, and random strangers that have help guide my path. I will say that my ex-wife came along and then everything I was, changed for the better as a result of meeting her. She was the one that made it easy for me to take my first improv class. It was her persistence that got me out of the worker seat and into the leadership seat. I was her that pushed me to follow my dreams. It was her and I together that gave me my son. And let me tell you, you have no idea what expectations are until you have a kid. So, because of her my life was turned right-side-in.

At the same time, while she was there for some of the biggest transitional pieces, I was well on my way because of so many other things. It comes back to me being there for me even when nobody else was (or did I not see them there? ;-) Ah perception!!

How have you used your success to bring goodness to the world?

My business is actually just that. I take what I have learned and implemented and I bring that to other organizations, managers, executives, and cultures. I don’t change who they are, I simply provide them with the tools to make themselves so much more. I bring awareness so that they can accept where things are and rather than leave them wondering how, I provide them the tools to get where they want to go.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

Well, I have to quote myself again. “The only reason anyone gets upset is because an expectation hasn’t been met.” I used to be a hateful and bitter person. Not necessarily to anyone else, but certainly to myself. I absolutely hated myself. I had so many expectations of myself that I wasn’t meeting that it was easy to beat myself up. When I actually took the time to stop myself and understand the expectation, where it came from, and how to work with it, I was able to be at peace with myself.

If I had to choose someone else it is Richard Branson’s quote, “If somebody offers you an amazing opportunity but you are not sure you can do it, say yes — then learn how to do it later!” I have taken this to heart on many occasions. And it works.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

Improv improv improv. I believe improv should be taught in schools as a required course. And not just stage improv. Yes it needs to be improv for stage as that is the easiest way to learn, but it needs to be taught in real life scenarios. How to relate it to life, family, business, and self. The level of confidence that comes from learning improv and implementing it into everyday life, is transformative.

Thank you for these fantastic insights. We wish you continued success!

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Jason Malki
Authority Magazine

Jason Malki is the Founder & CEO of SuperWarm AI + StrtupBoost, a 30K+ member startup ecosystem + agency that helps across fundraising, marketing, and design.