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We played Dungeons and Dragons as a Team Building Experience.

We hired a DM to host 6 hours of adventuring. It was WebiNerd-tastic! Here’s what we learned.

We’re a rather small but quickly growing firm with a 100% remote workforce. As such, we don’t have “water cooler time”. Getting to know one another personally and professionally; our strengths and areas of focus can be challenging at times. Everything we learn about one another has the potential to bring us closer and make us a more cohesive and effective team.

I have fond memories of playing Dungeons and Dragons throughout my life, and I’m also the founder of The WebiNerd – I am required to think outside the box when it comes to growing the company. So, I tasked everyone with rolling a D&D character and off we went on a great adventure to save the realm – a band of would-be heroes from WebiNerdia. 

As we played, I was drawing parallels to the business constantly. Maybe your dragon to slay is marketing automation, client support or any number of other business monsters. Taking the time to use your creative mind is healthy and may just inspire something new in your organization too. If nothing else, it’s fun!

What we learned from our time in a fantasy world.

Make more time to just BE together as co-workers

Our company is forever fully remote and our staff live around the country. We don’t walk past one another’s desks or bump into each other in the break room, so making time to be together without an agenda is really crucial. Other fun things we have in mind to meet this need are a movie night watch party and a regular “working meeting”. The working meeting is simply a block of time for us to sit in a virtual meeting together and get our work done. We can share thoughts and ideas as if we were across the table from one another. 

Minimize distractions when a crucial task is at hand

Ignore the bats – kill the hellhounds! At one point in our D&D game we got held up attacking the nuisance bats while ignoring the larger, more imminent issue of the hellhounds and giant worms. This moment affirmed the importance of putting processes in place that help you and your team stay focused on the larger goals. Develop tools and processes to help your team reel in those wild distractions flapping around your heads that may keep you from making the greater progress.

Know your role and perform it first and best

No one benefits from the cleric going rogue. Take the time to ensure that your team members know their role in your organization end-to-end. I love people that can pitch in to help others and sometimes save the day, but not if their own work suffers because of it. We rely on one another to be timely and accurate in our own work before contributing to other goals. 

Understand the roles of others

Effective party members (and employees) know how to identify key resources for quick success. No one wants to spend time asking around for answers. Provide your team with the organization’s structure and relatable work functions to keep your team members from wandering in the woods. 

Don’t be afraid to try unexpected, creative solutions

If you want to use your magic hand to try and grab the bats, that’s fine. Just be ready to deal with it not working. Unexpected solutions often make everything come together in new ways that make great sense. Give it a shot, try something new, but be prepared to pivot if it fails and minimize the potential for blowback to affect your results. 


Setting up to play Dungeons and Dragons

Creating a Character

A good friend shared a personality test with me last year that states what D&D character and class you are and I got a kick out of it. I assigned it to the team to help me learn more about them. You can take it here: What D&D Character Am I? 

With a character and class selected, we sent people to the D&D Beyond website to build their character sheet. This required a bit of assistance as we only had a couple of members familiar with D&D, but it was really fun to laugh and joke as we rolled our elves and halflings, wizards and bards. Some people really didn’t get it until we started playing, so it was important to be there to guide them through the fog of war. 

Why did we go about choosing characters this way? D&D is a game of imagination and fantasy, but our goal was to get to know one another better. Having our characters being somewhat reflective of our real-life personalities was important to the experiment – important enough to merit answering 140 questions

Finding a Dungeon Master

I found an amazing friend on LinkedIn to host for us as a Dungeon Master (DM). There are many “professionals” out there offering this DM as a service model, but I found none of them were actually business people willing to respond to my emails (get it together, folks). So, I met with Samanta Chan and she was willing to help us out. 

Sami sent us all to roll20.net which we used as a Virtual Tabletop (VTT) to play the game. She was kind enough to collect our character information and have it all built out for us to play when we arrived for our first of two sessions. With a bit of introduction, we were off on an adventure to save the villagers of Lakemere from the monsters attacking the crossroads nearby – pretty epic for a first outing.

Here’s what Sami had to say about the experience:

“Dungeons and Dragons is a game about collaboration, imagination, and creative solutions. Though it might be a steep learning curve, the team at Webinerd threw themselves into the game wonderfully, and by the end, were coming up with solutions any DM would be proud of. I hope that this taste of D&D will encourage them to look for some new games so they have more memorable adventures!” 

Samanta Chan

Why I’m learning to be a Dungeon Master

I may be the owner of a small company working with hundreds of corporate clients, but I take this nerd thing seriously. I’ve always wanted to DM since I was a kid in school. I used to read the dungeon manuals from cover to cover, but it was hard to put a game together. Doing this online instead of on paper makes it so much more accessible, saves a ton of time and new learning. Now that it’s so easy to do, my inner 13 year old is awake and excited. 

Being a DM gives me a chance to give others the gift of escape into the world of their own imagination. It’s really fun to see how various people take on their role in the game, who likes to role play and who is happy to just be swinging a war hammer. 

Aside from the epic fantasy of it all, D&D is a great exercise in creative thinking, extemporaneous speaking, solutions finding and so much more. It’s been really fun and I’ve found a chance to help many grateful people learn the game. You can find me online as Kalt Abent – let’s get nerdy!


Interested in running your own D&D team building experience? I’m still learning, but I would love to chat and share what I’ve learned so far.

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