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Get Comfortable with Improvisation: Practical Tips for D&D and Leadership

Professional using improvisation learned from D&D at work.

I’ve written previously about the importance of improvisation, both at the gaming table and as a leader. However, improvisation can be intimidating in both cases. Yet, being able to think on your feet, adapt to unexpected changes, and make decisions in the moment is a vital skill that can boost your confidence and enhance your leadership abilities. This article covers practical tips for getting more comfortable with improvisation and explores how this skill benefits both D&D players and workplace leaders.

Why Improvisation Matters

In D&D, improvisation brings life to the game. A well-prepared Dungeon Master (DM) can set the stage, but it’s unplanned moments, like a character’s unexpected actions or a twist in the story, that make sessions really memorable. The ability to react, adapt, and roll with the punches is what keeps the game fluid and engaging.

Similarly, in the workplace, leaders face unplanned situations daily, from client feedback to team crises. Those who can adjust on the fly, make quick yet informed decisions, and guide their teams through uncertainty are more likely to succeed.

Practical Tips to Build Your Improvisation Skills

Here are some tips on how to improve your improv.

Embrace Mistakes

  • In D&D: No DM has every possible outcome planned, and that’s okay. When players go off-script, don’t be afraid to make something up on the spot—even if it’s a little rough. Mistakes can lead to more interesting storytelling. For example, a misunderstood rule might create a new, fun dynamic in combat or a half formed NPC plucked from thin air can become a much loved party companion.
  • In Leadership: Mistakes are learning opportunities. If you make a wrong call, own it, adjust quickly, and move on. Being comfortable with failure helps you improvise with less fear and hesitation.

Practice “Yes, and…”

  • In D&D: Yes, and… is an improvisation staple. Instead of shutting down an unexpected idea, build on it. If a player says something wild, rather than saying “no, that can’t happen,” try saying “yes, and…” to take their idea and move it forward. For example, if a player decides to negotiate with a monster instead of fighting, roll with it and add complexity to the encounter.
  • In Leadership: In meetings, say “yes, and” to ideas rather than shooting them down. Never dismiss things out of hand. Build on team members’ suggestions, fostering a more creative, solution-oriented environment.

Set Boundaries to Create Freedom

  • In D&D: Some of the best improvisation happens within boundaries. Give yourself a loose structure—like a few key story beats or a clear understanding of the environment—so you have a framework to work within. This allows you to improvise while staying grounded.
  • In Leadership: Having a clear vision or framework for your team gives you flexibility to adapt without losing sight of the overall goals. When improvising, it really helps to have a guiding principle to fall back on.

Start Small

  • In D&D: Try improvising in low-stakes situations before doing it in major story arcs. Start with character interactions, minor NPCs, or side quests, where a misstep won’t have huge consequences.
  • In Leadership: Begin by improvising during smaller meetings or in less formal conversations. Over time, this will help you build confidence for bigger moments, like client presentations or crisis management.

Prepare to Improvise

  • In D&D: Ironically, preparation can make you a better improviser. When you know the world, characters, and plot beats inside and out, you’ll have more flexibility to pivot. Write down a few rough outlines of NPCs’ or Factions personalities or motivations. When things go off-script, you can lean on that prep work to improvise in a way that feels natural.
  • In Leadership: In the workplace, preparation is key. Know your team, the project, and potential pitfalls ahead of time. This foreknowledge allows you to respond quickly and effectively when something doesn’t go according to plan. Be warned, improvising without preparation can lead to some pretty unpleasant outcomes.

Stay in the Moment

  • In D&D: Being present with your players keeps the game moving and lets you respond to their cues. Listen actively, react to their energy, and don’t worry about the next scene or arc—just focus on the moment.
  • In Leadership: In leadership, staying present helps you stay attuned to your team’s needs. Active listening allows you to catch important cues in meetings or conversations, which aids in quicker, more adaptive decision-making.

Use Prompts and Constraints

  • In D&D: If you’re struggling to improvise, lean on prompts like dice rolls or random tables for inspiration. These can kick-start your creative process when your mind goes blank.
  • In Leadership: In the workplace, use frameworks or decision-making tools to help structure your thinking when improvising. For example, asking yourself key questions (like “What’s our goal?” or “What resources do we have?”) can guide your decision-making.

The Benefits for D&D Players

Improvisation adds richness to the experience of playing D&D. As a DM, it creates organic moments of storytelling, while as a player, it enhances your ability to contribute meaningfully to the group dynamic. It also:

  • Improves problem-solving skills: In a game where dice rolls and player choices can change the course of events, improvisation is essential for finding solutions to unexpected problems.
  • Enhances creativity: The more you improvise, the more you’ll notice new ways to tackle challenges or interact with the story.
  • Boosts confidence: Every time you improvise successfully, you build your self-assurance, making future off-the-cuff moments easier and more fun.
Learning improvisation at the gaming table can really help at work.

The Benefits for Leaders

For leaders, improvisation offers tangible workplace benefits:

  • Adaptability: In today’s fast-changing business environment, leaders who can pivot when needed are invaluable. Improvisation teaches you to think quickly, assess the situation, and make decisions that keep the team moving forward.
  • Problem-solving under pressure: Much like in D&D, leaders often have to deal with unexpected challenges. Being comfortable with improvisation helps you manage these situations without getting overwhelmed.
  • Building team trust: A leader who is adaptable and open to creative solutions will foster an environment of trust and innovation. Team members will feel more comfortable bringing forward their ideas, knowing the leader can roll with the unexpected.

Improvisation Is a Skill Anyone Can Develop

Improvisation isn’t about being reckless or making things up for the sake of it. It’s about responding to the moment with confidence, creativity, and control. Whether you’re running a D&D game or leading a team at work, you can practice and refine this skill through small, intentional actions. The more you do it, the more natural it becomes—and the more effective you’ll be in both your roleplaying and leadership endeavors.

For more inspiration about improvisation check out this article from Forbes for leaders and this one from D&D Beyond for the gaming inspiration.

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Overcoming Your Secret Hobby Shame


The worlds of the roleplaying and gaming hobbies are filled with thrilling stories, deep characters, and endless creative opportunities. Whether you’re slinging spells or battling for survival, these games have drawn people in for decades. Yet, many enthusiasts find themselves concealing their passion, feeling hesitant to share it with others because of a phenomenon known as “hobby shame.” I should know, as I’ve experienced this strongly at different periods in my life.

What is Hobby Shame?

Hobby shame is that nagging feeling of embarrassment or self-consciousness about a pastime that doesn’t fit societal norms. People may feel pressured to hide hobbies that are perceived as “childish” or “geeky” by some, like painting miniatures, designing dungeon maps, or discussing the lore of a fantasy world in detail.

For D&D and Warhammer fans, hobby shame might come from a misconception that these games are outdated, escapist, or frivolous pursuits. However, we know that the reality is far different—these hobbies offer rich opportunities for creativity, social connection, and skill-building that go beyond mere escapism.

My Hobby Shame

As a kid I loved all things fantasy and quickly gravitated to Dungeons & Dragons and Warhammer. The sense of having another world at your very fingertips was intoxicating for me. It’s difficult to pinpoint when I started to feel shame about my hobby. However, I think it was early in high school.

Adolescence is a difficult at the best of times. Trying to understand your place in the world and fit in can be excruciating. For me, like most other people, I struggled to find the balance. Of course, roleplaying and wargames were very much a niche past time. While I loved all things D&D and miniature games gave me a huge kick, I found it incredibly difficult to open up about it at school, mainly I think, due to a fear of ridicule. While I did game with some friends, I hung with another crowd with did not. This was compounded at home with my Dad regularly making fun of the hobby. While not malicious, this made me split my world in two. The secret gaming side and the other skateboarding person.

Knowing what I know now, I’m sure it wouldn’t have been a big deal. But there was a huge reticence in wearing my D&D heart on my sleeve.

This continued through to University, where despite joining the RPG Society and gaming every Sunday I was still reluctant to share my hobby outside of that circle. Fast forward to my thirties. I finally didn’t care what people thought and am open about my passion for gaming with friends and colleagues. Of course this blog helps get it out there. As such I’ve made some great friends who I game with regularly and even converted a few non-gaming friends. Funnily enough most people are really interested in the hobby. Only one friend takes the piss, and he is now very much outnumbered.

Where Hobby Shame Comes From

I find it difficult to pinpoint where this feeling of “hobby shame” came from for me. It’s probably a mix of the following:

Societal Expectations: Fantasy gaming has historically been niche, associated with stereotypes about “nerds” and “geeks.” Society has often stigmatized fans of fantasy games as lacking social skills or living in an imaginary world.

Age Stereotypes: Some people see these hobbies as things you “grow out of.” The image of painting miniatures or playing a tabletop RPG is often pigeonholed as a teenage or college-age activity rather than a fulfilling, lifelong pursuit.

Misunderstandings About Complexity: To an outsider, a complex game like Warhammer or D&D can look intimidating, making the appeal difficult to understand. People unfamiliar with the games may wonder, “How can something with such intricate rules and detailed worlds be fun?” This lack of understanding can lead to dismissive or judgmental attitudes.

Some of the ads from back in the day.

Why We Shouldn’t Be Ashamed of Our Hobbies

There are lots of reasons why we shouldn’t accept hobby shame. Luckily we now live in a world where D&D, video games and miniature gaming are at all time popularity highs. Societal norms are much more accepting and people are beginning to understand the benefits of a hobbies like ours, including:

Fostering Creativity: Whether painting Warhammer miniatures or designing a D&D campaign, these hobbies involve significant creativity. Crafting a D&D storyline involves weaving together characters, setting, and narrative arcs, much like a writer or filmmaker. In Warhammer, painting armies and building terrains allows players to express their artistic vision. Creativity isn’t just child’s play—it’s a skill with tangible mental health benefits and real-world applications.

Building Social Connections: Both D&D and Warhammer are fundamentally social. In D&D, players work together to overcome challenges, requiring teamwork and communication. Warhammer is no different; players build friendships with fellow hobbyists as they share tips on tactics, painting, and lore. These games foster strong bonds, often forming communities that are inclusive, supportive, and diverse.

Learning Problem-Solving and Strategy: Far from being mindless pastimes, D&D and Warhammer encourage players to think strategically. In D&D, players tackle complex problems, often working together to find creative solutions. Warhammer’s tactical depth requires planning, patience, and resilience. These problem-solving skills translate into professional and personal life, developing qualities like patience, adaptability, and resilience.

Encouraging Emotional Resilience: Losing a cherished character in D&D or seeing a meticulously painted Warhammer squad defeated in battle can be a test of emotional resilience. Players learn to accept failure and understand that setbacks are part of the experience. Resilience is a valuable trait, helping us navigate challenges in real life.

The Joy of Play: As we get older life becomes much more serious. The real world demands so many responsibilities that we forget the joy of play. Immersing ourselves in hobbies like these allows us to reconnect to play, which has huge benefits to our mental health. To learn more about Play check out the National Institute of Play. I’ll definitely be exploring this more in a future article.

Embracing and Sharing Our Hobbies

The key to overcoming hobby shame is to take pride in what these games offer and to share that pride with others. Here are a few ways to do this:

Build Confidence Through Community: By connecting with other D&D or Warhammer fans, you’ll find a supportive group of people who understand the hobby’s unique value. Attend local meetups, join online forums, or visit gaming shops. Being part of a community makes it easier to let go of feelings of shame.

Explain the Benefits: When people outside the hobby question it, try explaining what you love about it. Sharing stories of teamwork in D&D or showing off a well-painted miniature can help others see the value and creativity involved.

Integrate the Hobby Into Your Routine: Try small actions like proudly displaying a painted miniature at work or mentioning a memorable D&D session. Making the hobby a normal part of your life can help ease feelings of shame, turning it into something you enjoy openly.

Reclaiming the Joy

Dungeons & Dragons and Warhammer are so much more than escapist fantasies. They’re platforms for creative expression, emotional growth, and meaningful social connections. Embracing these games openly can help dispel the misconception that they’re childish or strange and help foster a richer community of people who share in this imaginative pursuit.

By challenging hobby shame, we can make the gaming table a space not just for fantastic adventures but for real-world growth, resilience, and joy. Whether you’re rolling dice in a dungeon or painting your latest squad, know that your hobby has value—both to you and to the world around you.

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2024 Dungeons and Dragons at Work Retrospective

Happy New Year!!

Another year gone. I cant believe I’ve been writing this blog for over a year and a half. What a journey. Explored some great concepts and I’ve found that I’m really firming up my thinking on using D&D and other rpgs to gain experiential leadership learning. I’ve also met with some amazing people and had thoroughly enjoyable conversations. Good times! This retrospective showcases a few highlights from 2024.

Is it hard to be a dungeon master? One of my most popular posts where I discuss the challenges of DMing as well as providing some tips to get you started. Given the popularity of this article I’m wondering whether a series of DM tips and tricks might not be a good idea for 2025. Watch this space.

One of the Echoes of Xenos game board set ups

One of the great things about writing around leadership and D&D is designing and playing games that explore these concepts. I designed and ran the Echoes of Xenos event for a group of friends. I took elements of D&D, megagames and miniature wargames to encourage emergent play. Did everyone have fun? Yes. Did it work as planned? Not quite. But I’m taking the learnings and designing a similar event that I will be writing more about soon. I’ll also be designing and playing more games this coming year.

Larry Elmore’s Dragon Slayers and Proud of it.

Another popular post was my take on Larry Elmore’s painting Dragon Slayers and Proud of It. This shows a low level party of adventurers showing off their latest victory. I related it back to celebrating the little wins. Advice that I still need to heed from time to time. It was really fun to explore such an iconic piece of art.

Another fun aspect of this adventure was being invited onto a couple of podcasts to talk about my journey so far. If you want to hear me talk about these topics, my hobby origin story and the campaigns I run listen here:

Bedroom Battlefields

Legends Loot and Lore

Finally, 2024 has been a good year for Dungeons and Dragons at Work. But it wouldn’t be possible without people reading it. So thank you to all who stop by and have a read. I hope you are enjoying the content. Feel free to drop suggestions or feedback in the comments below.

Happy New Year and wishing you all a fantastic 2025!

Normal service will resume next week.

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Dungeons & Dragons and Christmas: A Perfect Blend of Magic and Merriment

As the festive season approaches, it’s the perfect time to think about gathering friends and family for shared experiences that bring joy, laughter, and a bit of magic. Most people think of Christmas as a time for gift-giving, decorations, and hearty meals. But, it’s also a fantastic opportunity to embark on an epic Dungeons & Dragons adventure. After all, D&D has a lot in common with the spirit of Christmas: camaraderie, storytelling, and imagination.

The Magic of Storytelling

Christmas is steeped in stories—from classic tales like A Christmas Carol to the folklore of Santa Claus. In the same way, Dungeons & Dragons is built on the power of storytelling. Whether you’re a veteran dungeon master or a first-time player, the season provides a perfect backdrop for creating memorable moments. Much like the stories that get passed down during the holidays.

Bringing People Together

The holidays are all about gathering with loved ones. Of course, D&D is one of the best ways to bring people together in a meaningful way. Much like sitting around the Christmas tree or the dinner table, gathering around a D&D table (or even a virtual one) invites everyone to collaborate, strategize, and have fun together. Dungeons & Dragons fosters teamwork and deepens relationships, making it a wonderful way to share quality time with friends and family during the holiday season.

You could even run a special holiday-themed campaign: perhaps a quest to recover stolen gifts from a mischievous goblin or an epic journey through a winter wonderland to stop an ancient frost spirit. With D&D, the possibilities are as endless as your imagination, and the festive setting can add an extra layer of magic to your adventure.

I ran a Christmas themed adventure based loosely on the original Klaus comic book where the party were transported to a magical realm to help the mage Nikmas defeat a villainous overlord. We had great fun and the party ended up burning the overlords castle to the ground. In our campaign world Nikmas is celebrated at the end of every year and castle effigies burned on bonfires. As players we wish each other Merry Nikmas too. This tradition has now been going on for years.

Amazing inspiration for a Christmas themed D&D session.

Giving the Gift of Adventure

Another beautiful parallel between Dungeons & Dragons and Christmas is the act of giving. When you’re a Dungeon Master, you’re constantly crafting experiences for your players—moments of triumph, tension, and laughter. In a way, every session is a gift that unfolds as the game progresses. And for players, they give back with their creativity, problem-solving, and dedication to the story.

This season, consider giving the gift of adventure. Whether it’s a new D&D starter set, custom dice, or even just the time to run a one-shot for a group of friends. Dungeons & Dragons is the gift that keeps on giving, long after the last piece of tinsel has been packed away.

Wishing You a Festive Season of Fantasy

Whether you’re sleighing dragons or just relaxing with hot cocoa and character sheets, Dungeons & Dragons offers a perfect way to add a little more adventure to your Christmas celebrations. So this year, consider gathering your party and diving into a world of magic, heroism, and fun.

Wishing you and your loved ones a joyful, imaginative, and festive season filled with laughter, warmth, and epic quests. Happy holidays, and may your dice always roll high!

I’ll be taking a break from writing to enjoy some time off with family and friends (with some gaming mixed in I hope). Normal service will resume in January.

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Character Death: Embrace the Suck and Grow Resilience

Characters in roleplaying games are an extension of each player. Which is why character death is more than just a game mechanic—it’s a powerful tool for storytelling, tension, and personal growth. When a beloved character meets their end, it can be devastating for players. Yet, these moments also provide an opportunity to build resilience. In real life, failure often feels like a setback, but it’s actually a critical part of growth. The same is true in D&D: loss, adversity, and even death create some of the most cinematic and unforgettable moments in the game.

In my long-running campaign, we’ve had our fair share of tragic yet unforgettable character deaths. One of my favorites was a dwarf pugilist who heroically fought his last battle, only to be turned into a statue—immortalized in stone, a symbol of both his strength and vulnerability. A halfling midwife was vaporized in a split second by a green dragon, a gut-wrenching moment of loss that haunted the party for sessions afterward. A tiefling warlock sacrificed her very existence to save the rest of the group. Her selfless act transforming the party dynamic forever. These deaths were heartbreaking, but they were also cinematic, exciting, and pivotal moments in the campaign.

Medusa, a regular source of character death

Character death, like failure in life, can feel like an ending. But in D&D, it is also a beginning—a chance to reflect, grow, and adapt. Just like the stories we tell in the game, our failures in real life can become part of a larger journey. They don’t define us, but they do shape us. The more we play, the more we learn that resilience is key to both the game and to life.

Three Tips for Building Resilience Through D&D

1. Embrace the Story, Not Just the Success

Death and failure are part of the journey. While everyone loves a victorious ending, the setbacks and losses are what make the victories truly memorable. When your character falls, think of it as an opportunity to add depth to your story. How does your party react? How does the world remember your character? By embracing these moments, you develop the ability to face and process loss, which is key to resilience.

Resilience Tip: Take time to reflect on what the character meant to you and the story. Honor their journey, even in their demise. The emotional impact will deepen your connection to the game and make your next character all the more meaningful.

2. Adapt and Overcome

Of course, the death of a character doesn’t mean the end of the campaign, and it shouldn’t mean the end of your engagement with the story. Whether it’s rolling up a new character or finding creative ways to re-enter the narrative (perhaps through a descendant or a resurrected version with lingering consequences), the game challenges you to adapt. This builds mental flexibility and teaches you to face challenges head-on rather than giving up.

Resilience Tip: When a character dies, brainstorm new ways to stay involved in the story. Maybe your next character can help the party move forward, or you can shift your focus to supporting other players’ stories. This ability to adapt strengthens resilience, both in the game and in real life.

3. Celebrate the Failure

Character deaths can feel like a failure, but often they’re the most memorable part of the game. Lean into those moments—remember them, share them, and laugh about them. Some of the greatest stories come from plans going wrong or characters meeting unexpected ends. Just as in life, failure is a stepping stone to growth, and those hard moments often lead to the most rewarding learning experiences.

Resilience Tip: After a character death, take time to celebrate the story of the character and what they achieved before their demise. Talk to your fellow players about the impact of the moment. By turning failure into a point of celebration, you can shift your mindset toward seeing challenges as opportunities for growth.

Final Thoughts

Dungeons & Dragons, like life, is filled with ups and downs. Character death and failure are inevitable, but they’re also invaluable. They teach us to roll with the punches, adapt to change, and find meaning in the struggle. The next time your character faces their doom, take a deep breath and remember: it’s all part of the journey. Through these moments, both in the game and in life, we build the resilience that carries us forward.

Resilience isn’t about avoiding failure; it’s about embracing it, learning from it, and continuing the adventure. So, let your character’s death become part of your legacy—because, in the end, the stories we tell about our failures are often the ones that shape us the most.