Dungeons and Dragons in the C-Suite
- Admin1

- Sep 25
- 4 min read
Updated: Sep 26

Conquering the Fear of Public Speaking
Sometimes nothing goes right and we have to make it up as we go along. Dr. Prof. Amy Cuddy said, “Fake it until you become it.” It’s good advice, and I’m going to raise my ‘nerd-flag’ a bit higher here because a few weeks back, I was asked to help with a capital raise. During the meeting, the entrepreneur froze when the conversation got pulled into an unexpected direction. Their ‘deer in the headlights’ reaction felt very familiar, and my brain immediately referenced Mike Tyson’s famous phrase, “Everyone has a plan until they get punched in the face.” While the situation unfolded, my brain pulled out of the conversation. I had fallen down a rabbit hole, and all I kept thinking about was how every Dungeons and Dragons gaming session I host with my friends turns out the exact same way.
Wait! Did he just reference a game?
--Yes, I did, and believe me, it’s important.
According to many studies, the number one fear people have is having to speak in public. Do you know what number two is? Death. That means that in the minds of most people, (and Jerry Seinfeld who wrote this joke) if they were to go to a funeral, they would feel better being in the casket than having to give the eulogy. It sounds crazy, but it’s true. We just need to practice fighting that fear in order to overcome it.
But, how?
--Toastmasters.
So, what do boardroom presentations, the Toastmasters, and Dungeons and Dragons all have in common? – they’re great at developing improvisation skills.
Boardrooms can be very chaotic places. Meetings don’t always start on time, and not everyone keeps to the agenda. I’m constantly asked how to get better at presenting when the pressure’s on and things don’t go to plan. Perhaps someone asks you something you weren’t prepared to answer, or a colleague ‘threw a wrench’ into your discussion; just remember to take it in stride. Spend a quiet few seconds thinking if you actually have the correct answer, and in the worst-case scenario say the three magic words, “I don’t know.” Demonstrate your ability to keep cool under pressure, because what boss or higher up is going to promote someone who crumbles the moment things start to go wrong.
Step two is getting better at dealing with the unexpected and learning how to ‘play off your back-foot’. This means you need to rehearse being in that uncomfortable position. You aren’t going to want to do this in the executive conference room, so finding a safe and reliable place to train is your best bet. Queue up Toastmasters International, the public speaking club whose members decided to conquer their fear of presenting in public. Look them up online to find the one nearest you. (Toastmasters.org) Easy to work with and join, they specialize in helping people from all walks of life, regardless of which level they are at in their careers. In-person or virtually, the meetings are usually hosted after hours, a few times per month, and specialize in putting speakers on the spot.
Good or bad, exercises thrust participants into random scenarios where they may have thirty seconds to prepare a firm stance on whether pie or cake is better (it’s pie by the way); or a minute to explain where you’re going for your next vacation and why. (individual experiences may vary…) A referee can be appointed to help you reduce the number of “ahhs…” or “umms” coming from your mouth, and offer you pointers on your body language. Try it out! You’ll thank me later.
Now for the more curious question: How can Dungeons and Dragons help you in the C-Suite? At the risk of raising my ‘nerd-flag’ even higher here, I’ve been playing DnD for over thirty years, and I’ve been a storyteller for a good portion of that. For those of you unaware, DnD is a game where a group of people get together to experience an adventure right at their tabletop. Each person generates a character with their own skills and persona, and does their best to participate in the narrative which the Storyteller (the person who wrote the adventure) has created. The Storyteller creates the framework of the adventure, designs the maps or gameboard, and has the plan. No one knows how anyone will react to the story unfolding, but most do their best to ensure that things move forward. As you’ve probably guessed, not everything goes to plan. The group often takes things into unexpected directions, which forces everyone to make things up on the fly.
When it comes to learning about how to deal with the unexpected, these unplanned departures have been the best teacher I’ve ever had. I’ve created entire story arcs from these divergences, some of which have led to hundreds of written pages, and countless hours designing additional content just to tie up loose ends. It’s been great practice and a tremendous learning experience for everyone involved. Thus, my advice is to try out some of these roleplaying games like Dungeons and Dragons to learn and hone your own improvisation skills. Give it a shot. Maybe you’ll discover a new hobby, and develop your talent along the way.
Either way, preserving the flow of conversation to keep our momentum going doesn’t need to be a real challenge. You just need to practice working off your back foot.
Good luck and happy presenting!





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