Dion Flynn Keynote Speaker

  • Best known for his impersonation of Barack Obama on The Tonight Show Starring Jimmy Fallon, over 100 appearances

Dion Flynn's Biography

Dion Flynn is a teacher, improviser, comedian, performer, writer, and army veteran best known for his impersonation of Barack Obama on The Tonight Show Starring Jimmy Fallon, among his more than 100 appearances on the show. He is an expert in fun and innovative ways to help people connect with themselves and others.

Dion discovered that the skills he used on stage and TV for both improvisational and scripted comedy paralleled the skills needed in recovery from process and substance addiction, and also came in handy for basic human development as well as interpersonal and business communication skills. As a result, he co-created The Improvisor’s Mindset (with Jeanne M. Stafford) to draw connections between these theatrical skills and the critical skills needed for successful, grounded connection for the spiritual seeker, and an enhanced business and personal life for the rest of us.

Dion sees the journey from isolation to connection as the basic journey of any recovery and the basic storyline of the soul.

Dion has performed with, taught, or led improv workshops for MTV, VH-1, Logo, Rock The Vote, Google, PNC Bank, Herman Miller, The M&A Advisor, Ardent, Maersk, PWC, Ecolab, The North Carolina Lawyers Association, and more. He holds a master’s of fine arts degree in acting from New York University’s Graduate Acting program and has worked with Spike Lee, Rosie O’Donnell, Kate McKinnon, Josh Radnor, Shakespeare In The Park, The Public Theater, The Guthrie Theater, The Moth Storytelling, Armed Services Arts Partnership, and many other world-class artists and organizations.

Dion Flynn will get your people connected! Cited by Oprah Magazine as “one of our favorite creative thinkers. Your audience is wowed and takes home sure-fire nuggets that open more doors and close more deals using the basic tools of improv.

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Dion Flynn's Speaking Topics

Improv for Business

Learn to react naturally and spontaneously in every situation. In this highly interactive workshop, Dion Flynn puts audience members at the center of the experience. Whether delivered in person or virtually, participants learn the power of the improv principle "Yes, and" and how to keep conversations flowing naturally, collaboratively, and productively.

This workshop is ideal for managers, leaders, teams, and anyone who regularly interacts with customers or colleagues.

Participants will learn how to:

  • Apply the "Yes, and" mindset to workplace communication
  • Think more quickly and confidently in unexpected situations
  • Improve collaboration and team dynamics
  • Enhance listening and communication skills
  • Build confidence in professional interactions

Truth in Comedy

Let's get everyone together and do some stand-up comedy.

Dion Flynn leads groups of any size through a stand-up comedy workshop inspired by the unique quirks of their own corporate culture. Every organization has its challenges, inside jokes, and shared experiences. Through comedy, participants uncover truths, strengthen connections, and create a memorable shared experience.

By making light of workplace challenges, teams can surface important conversations, improve morale, build stronger relationships, and uncover opportunities for growth.

Participants will learn how to:

  • Use humor as a tool for connection and team building
  • Explore workplace challenges from a fresh perspective
  • Strengthen trust and camaraderie across teams
  • Improve morale through shared experiences and laughter
  • Reveal opportunities for growth through creative expression

Improv for Sales

The basic tools of improv are the basic tools of human relationships—and therefore the foundation of successful business development and sales.

In this engaging workshop, sales professionals learn core improvisation techniques and discover how those skills translate into stronger customer relationships, better conversations, and increased sales performance.

Participants will learn how to:

  • Listen more effectively to customer needs
  • Build stronger rapport and trust with prospects
  • Respond confidently in dynamic sales conversations
  • Think on their feet during negotiations and objections
  • Apply improvisation principles to improve sales results

Improv Recovery Workshop

Actor, comedian, Army veteran, and recovering person Dion Flynn—best known as Barack Obama on The Tonight Show Starring Jimmy Fallon—leads recovering individuals and healthcare providers through theatrical improvisation workshops designed to strengthen connection, communication, and recovery.

The fundamental skills of successful improvisation mirror many of the skills required for successful recovery and healthy human relationships. In a safe, supportive, and fun environment, participants practice valuable tools for personal growth and connection.

Participants will practice:

  • Listening
  • Public speaking
  • Spontaneity
  • Empathy
  • Acceptance
  • Awareness
  • Presence
  • Vulnerability
  • Confidence

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Videos of Dion Flynn

Improvisor’s Mindset Sample
Truth in Comedy Workshop
"An Actor Prepares" with Dion Flynn and Josh Radnor
Putin & Obama Go On "Dr. Phil" Show

Comments & Testimonials

One of the funniest guys I know.
Jimmy Fallon Host The Tonight Show
Dion is extremely intuitive and is a fantastic listener. He can pull things out of you that you didn’t know were there and allows you to decide for yourself what’s the best…. I highly recommend him!
Paul V. Pompeo Lumen Technology Sales
Dion is both an inspiring artist and an excellent manager of people, which is a rare combination.
Thomas Brennan Senior Writer & Producer

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