One of my favorite Dungeons and Dragons paintings is the classic “Dragon Slayers and Proud of it” by the incredibly talented Larry Elmore. This shows an adventuring party proudly standing next to a dragon that they have just slain. The look of satisfaction on their faces is very real. However, the joy for me comes from the size of the dragon. It is pretty small. Not the heroic villain expected. To me they are celebrating their first win together. It doesn’t matter that it wasn’t an epic show down. A win is a win. Something that has brought the team closer together.
This got me thinking about our role as leaders. Why is it that so much communication tends to focus on compliance and improvement. Why don’t we celebrate the wins, regardless of size, with the team on a regular basis. Below I explore a few reasons why we should be celebrating the little wins in both D&D and as leaders in the real world.
Embracing Progress
In Dungeons & Dragons, success isn’t solely determined by defeating the final boss or completing a quest; it’s also about the smaller victories that pave the way. Perhaps your characters learn the part of the Villains grand plan. Or, maybe they make a new ally or buy a tavern. Whatever it is , it’s worth celebrating. Taking a moment to acknowledge the success together at the table helps bring the group closer.
Similarly, in business and life, progress often comes in incremental steps. Whether it’s mastering a new skill, completing a project milestone, or achieving a personal goal, each small win contributes to overall success. As a leader make sure to take the time to acknowledge these victories both with the individuals involved and the wider team. This will give your employees a great sense of achievement and let them know that their efforts are appreciated.
Building Momentum
Just as in D&D where every successful encounter builds momentum for the party, celebrating little wins in business and life can generate positive momentum. In game this could mean getting one step closer to saving the world. Alternatively, in business it can be the next milestone to reaching the annual objectives.
Big goals, on their own often seem insurmountable or impossible. Recognizing and acknowledging achievements, no matter how small, boosts morale and motivation. Letting people know that we will get there. Ultimately, propelling individuals and teams forward with renewed energy and enthusiasm.
Fostering Collaboration
Collaboration and teamwork are the cornerstones of D&D. Each player contributes their unique skills and abilities to overcome challenges. Looking at the team in Larry Elmore’s painting shows a group comprising strong fighters, stalwart clerics and an arcane magic user. Together, they have used their disparate skills to overcome their foe and get a win. Alone, a victory like this would never have been possible.
In business and life, celebrating little wins fosters a sense of camaraderie and collaboration. Recognizing the contributions of team members and acknowledging shared achievements strengthens bonds and encourages continued collaboration. When you succeed as a team, the team becomes stronger. Cultural touch points appear around the journey the team has taken together. For example, remembering the time the team pulled an all nighter to get a project out on time becomes a core part of the team identity, bringing everyone closer together.
Cultivating Resilience
When playing at the tabletop, setbacks and obstacles are inevitable. But it’s how adventurers respond to these challenges that define their journey. In the painting the heroes display cuts, ripped clothing and battle damage. Although small, the dragon they have conquered was no easy fight. If it was easy, there’s no reason to celebrate.
Similarly, in work teams and in life, encountering setbacks is all part of the process. By celebrating little wins, individuals cultivate resilience and develop the mindset needed to persevere in the face of adversity. Ultimately bouncing back stronger and more determined than before. Acknowledging when things are tough and working together to push through makes everyone stronger.
Savoring the Journey
D&D campaigns are epic adventures filled with twists and turns. But it’s the smaller moments of triumph that make the journey memorable. In many games the best memories are often the smaller improvised encounters that emerge from play. Perhaps it is a hireling they picked up in a village. Or their interactions with a bard who wants to write their story. No amount of planning by the DM can make these memorable moments. Rather it is playing together at the table.
Likewise in life, savoring the journey and celebrating the little wins adds richness and depth to the overall experience. Maybe it’s a junior project manger finishing her first project, or onboarding a new client or even finding the best coffeeshop near the office! By taking the time to appreciate the small victories along the way, individuals can find joy and fulfillment in the process, not just the end result.
Final Thoughts on Dragon Slayers
Have a look at the painting again. Are there any other details that speak to you? Perhaps the tiny box of treasure or the look of satisfaction on the heroes faces. Larry Elmore has really created an image with depth and meaning.
For me the painting highlights that in the epic tale of life, celebrating the little wins is not just about acknowledging achievements. It’s about embracing progress, building momentum, fostering collaboration, cultivating resilience, and savoring the journey. Whether in Dungeons & Dragons, business endeavors, or everyday life, recognizing and celebrating these small victories is essential for team cohesion, personal growth, and fulfillment. So, let’s raise a toast to the little wins and revel in the magic they bring to our adventures, both big and small.
Now go slay your dragon – no matter how small it is!
For another take on how awesome Larry Elmore’s painting is check out this video from Bardic Broadcasts.
