Interview - Dion Flynn

Improv for Business

Full Interview-


Growing up, Dion Flynn was the only brown kid in the trailer park. He wanted everybody to like him so he learned how to be creative and make people laugh. He used laughter as a medicine for the life pain that he was in at the time. Humor was the coping strategy and the language of his family. According to Dion, comedy, at its heart, is one technique for taking very difficult things that are hard to process and turning them into things that are entertaining. It’s a good skill set to have growing up. Dion was good at it and people started responding. Because of where and how he grew up, Dion got into television very early. Fast forward to the present. Dion Flynn has been seen on The Tonight Show over 100 times and is best known for his hilarious impersonation of Barack Obama. 

Joining the Army

He failed 9th grade because he wasn’t able to focus. Dion’s mom took him to the recruitment office to join the army but he was too heavy. When he was 17, Dion quit school and ran away to take some time off. He lost 100 lbs and came back and was able to join the army. “The army for me was about finishing something,” according to Dion. During his four years in the army, he learned how to face his fears, bond in an all-male environment, and learned lessons that you get from other men that you don’t get from your parents. The army took him out of his comfort and gave him life long confidence. He was also able to travel all over the world and learn about other cultures. “Adapt, improvise, and overcome was one of the informal philosophies of the army,” he said. He would find fixes and workarounds for things under great deal of both artificial and real pressures. He was stationed in Korea’s Demilitarized Zone (DMZ) between North and South.  That was his real-world mission with real-world pressures.

On Improvisation 

Dion learned some basic tools that are taught in improv schools around the world. One of them is the use of “Yes, and…” which is a way of accepting everything that’s brought to you and building on it, rather than saying “No”. Leaders can learn a lot about guiding people from practicing improvisation and learning “Yes, and..”. According to Dion, building empathy is one of the main things that come from practicing improv. When you are a high-status person like a leader or a CEO, improv gives you a chance to briefly play a different role in a fun way so you can understand what a low-status person feels like. “I give space for the small voices in the room to be heard fully without railroading them with my authority.”
Dion has worked with CEOs and leaders. According to Dion, these leaders are sometimes boxed into their own authority role and would benefit greatly from playing in an improv workshop so they can see the side of their workers and letting them be heard. People often get scared that if they let a low status person speak, it is going to overwhelm their high status position. Leaders must understand that it’s not a threat to let someone be fully heard.The trick with improv is the beauty of the brick-by-brick iterative dialogue.
Improvisation also helps salespeople tremendously, according to Dion. Improv uses ‘offers’ which is a basic term used in business. Dion shares that in an improv scene, everything a person says or does is an offer. When you train your mind to look at everything as an offer, you will learn how to build with things even if the reactions are instinctually off putting. This way, you can convert moments that would’ve ended the sales process in a non-manipulative fashion. Tapping your own intuition, increasing your awareness, and developing self-confidence that you can use in a sales process can be learned by practicing improv.

Improvisation for Introverts and Extroverts

Alan Alda, a seasoned actor and a great improviser, started a program called The Alan Alda Center for Communicating Science. He recognized that there are scientists who have earth-shattering, earth-saving, and life-saving things to say but they don’t know how to communicate it to lay people. These highly intelligent people in science are sometimes very inward and have a level of introversion in them. According to Dion, if you can’t communicate and get the deep thing that is inside of you out, no one can take any action on it. Sharing yourself is a major part of the improviser’s mindset and it involves saying the positive thing that you want to say about someone’s good work. “It is expressing a boundary in a way that gets your message across, but is not off putting and doesn’t alienate you from others.”
According to Dion, he is both an introvert and extrovert and his work over the years has helped him gain a deeper understanding of both personalities. He recognized that people who identify themselves as introverts or extroverts sometimes have a little bit more that they can learn about what is true about that orientation. Self-proclaimed introverts have a ton of wonderful things to say and can contribute and express them with a little bit of training in theatrical improvisation. Self-proclaimed extroverts can redefine the meaning of their personality and recognize the  crossover between the two personality types. 

Personal questions with Dion Flynn

LI: What is your favorite word?
DION: Silver. The color and the word too. I like it because a silver thing is shiny and bright reflects other things. The word itself has so much fun in it. It involves your whole mouth and your life.

LI: What is the sound that you love?
DION: OHM is nice. It’s a three-part, a triphthong, that is non-religious but if you make all three of them, it can touch all parts of your body. It almost makes your body a tuning fork and it tunes you into the present moment.
LI: If you could be someone or something else, who or what would you be?
DION: I’d be an eagle or a hawk circling down the breeze as the old lyric says in a Johnny Cash song. The ability to get up there, see everything from way up, ride the thermals, go back up, and to be an apex predator in that position so that nothing would attack me. I wouldn’t want to be attacked while I was gliding. That’s why I’d want to be maybe a pterodactyl or an eagle.

LI: In one year today, where will Dion Flynn be and what is he doing?
DION: I’m hoping that the health concerns that we have globally right now will recede and I will be working more with people in the same room. I’m looking forward to continuing to bring people together —  see them laugh, see their eyes, to see people cry sometimes, and see people have insights. That’s where I’ll be.