Tag: D&D

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Leaving a Legacy — as a Leader and as a Dungeon Master

When people talk about leaving a legacy, it often sounds grand — the kind of word reserved for visionary founders, political figures, or historical heroes. But in truth, legacy doesn’t have to be about something monumental or world-changing. It can be quieter, more personal, and built moment by moment through the people we influence and the culture we create.

As a leader, I think about legacy not as an accolade or a plaque on the wall, but as a living thing. It’s the ripple effect that continues long after you’ve stepped away. It’s the culture you build, the behaviours you reward, and the sense of belonging that people carry with them long after they’ve left your business.

A Leadership Legacy Built on Culture

For me, legacy begins with culture. I want to build a workplace where people genuinely enjoy what they do and who they work with. Where collaboration and kindness aren’t seen as soft skills, but as strengths that drive performance. Where people are trusted, supported, and encouraged to grow — not just into better employees, but into better leaders themselves.

If you can build that kind of culture — one that values connection, creativity, and care — it doesn’t stay contained within your walls. Over time, the people who thrive in it take those values with them. They share them in new teams, new organisations, and new industries. That’s how a leadership legacy grows: not through policies or slogans, but through people.

When I think about my own leadership legacy, I want it to be something that continues to live in others. I want to know that years down the line, someone who worked with my business or team is leading a team of their own — and that the positive culture we built together influenced how they lead. That’s how real change happens — not in a single moment, but through a chain of shared values that spreads quietly and steadily.

The DM’s Legacy: Building Worlds, Friendships, and Escape

Strangely enough, that idea of leaving a legacy — of creating something that lives on through people — feels very familiar to me. Because I’ve seen it before, at the Dungeons & Dragons table.

When you’re a Dungeon Master, you put a lot of energy into building worlds, crafting encounters, and bringing characters to life. You think your legacy might be the epic storyline you’ve designed or the clever twist you’ve hidden behind a screen. But in the end, that’s not what people remember.

What lasts are the friendships that form around the table. The laughter that comes from an unexpected dice roll. The moments when everyone forgets their phones and the outside world because they’re fully immersed in the story you’re telling together. That’s your true legacy as a DM — creating a shared experience that gives people a break from everyday life and connects them in a meaningful way.

I’ve seen players who started in my games go on to run their own campaigns, taking inspiration from the way we told stories or the sense of inclusion they felt at the table. Just like in leadership, the culture you create as a DM doesn’t stop when the session ends. It spreads — through new games, new friendships, and new worlds imagined by others.

Building a Lasting Legacy

When I think about leaving a legacy now — whether as a leader or a DM — I think of it less as an outcome and more as a community. It’s about creating something that feels safe, inspiring, and empowering, and then letting others carry it forward in their own way.

In leadership, that might mean building a team that lives your values long after you’ve moved on. In D&D, it might mean a circle of friends who still share stories and inside jokes years after the campaign ended.

Ultimately, both are about people and the stories we build together. The kind of legacy that matters most isn’t written down — it’s remembered, retold, and relived.

So whether it’s through the people I lead or the players I guide, my hope is the same: that something about the experience stays with them. That they take what we’ve built — the culture, the connection, the sense of possibility — and carry it into whatever comes next.

Because that’s what leaving a legacy is all about. Not the mark you leave on the world, but the spark you leave in others.

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Build Your Practical Coaching Skills With D&D

Orc coach giving practical coaching tips

A couple of weeks ago we looked at how D&D can give insight into leadership coaching. Coaching is about unlocking the potential of others—helping them find their own solutions, build confidence, and grow. And a session of D&D gives you dozens of opportunities to practice exactly that. In this article I look at some ways to gain practical coaching skills through playing D&D with your mates.

Here’s a few tips to help your practical coaching skills.

Active Listening: Pay Attention to the Details

At the table: In D&D, missing a detail in the Dungeon Master’s description can mean walking into a trap. Players learn to listen carefully, not just to what is said, but how it’s said.

In leadership: Listening with intent is the foundation of good coaching. Instead of planning your response while someone speaks, focus fully on their words, tone, and body language. Then reflect back what you heard:

  • “It sounds like you’re feeling stretched thin—what part of the project is weighing most heavily?”

Ask Questions, Don’t Give Orders

At the table: When a player is unsure what to do, the best response isn’t “You should cast Fireball.” It’s asking questions like, “What’s your wizard best at in this situation?” That prompts them to think, decide, and take ownership.

In leadership: Instead of solving problems for your team, use open-ended questions to help them discover solutions:

  • “What options have you considered?”
  • “What outcome would you like to see?”
  • “What support do you need from me to make that happen?”

This shifts you from problem-solver to coach.

Encourage Quieter Voices

At the table: Every party has a quiet player who might get overshadowed by louder personalities. A skilled Dungeon Master or fellow player creates space by inviting them in: “Hey, what’s your rogue’s take on this plan?”

In leadership: Teams are the same. Coaching means ensuring every voice is heard. You might ask:

  • “I’d like to hear your perspective before we decide—what do you think?”

This inclusion builds confidence and uncovers fresh ideas.

Celebrate Creativity and Experimentation

At the table: Sometimes the “right” solution isn’t obvious—so players experiment. They may try to distract the dragon with a song or use a spell in a clever, unintended way. Great D&D groups celebrate the attempt, win or lose.

In leadership: Coaching encourages experimentation without fear of failure. Acknowledge effort and creativity, even when results aren’t perfect:

  • “That was a smart angle—you tested something new, and we learned from it.”

This builds psychological safety and fosters innovation.

Turn Setbacks into Learning

At the table: Characters fail rolls. Plans go sideways. But those moments often lead to the best stories. Players learn to laugh, adapt, and move forward.

In leadership: Coaching reframes mistakes as opportunities:

  • “What worked here, and what would you try differently next time?”

This approach develops resilience and problem-solving skills in your team.

Final Thoughts on Practical Coaching

When you play D&D, you practice listening, questioning, encouraging, celebrating, and reframing setbacks. All of these are core practical coaching skills. Bring them into your workplace and you stop being the one with all the answers—you become the leader who helps others shine.

So, next time you sit down for a session, remember: you’re not just slaying dragons—you’re sharpening your skills as a coach.

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Gain Powerful Coaching Skills Through Dungeons & Dragons

A coach leading a team of orc football players

Coaches can be an important part of every leaders journey. They help the leader reflect and learn from their experiences. My personal leadership journey has greatly benefitted from both informal mentors and formal coaches. In fact, I still catch up with a coach regularly to reflect on my own leadership. These conversations have really helped me step out of the day to day and see my leadership from a broader perspective. As a leader it is beneficial to gain coaching skills to help your own staff reflect on their own journeys. Interestingly, I believe that coaching skills can be learned within Dungeons and Dragons, hidden within the game’s innate storytelling and teamwork. Whether you’re sitting behind the Dungeon Master’s screen or playing as a character, D&D creates countless opportunities to guide, support, and unlock the potential of others—exactly what effective coaching is all about.

Coaching in the Dungeon

As I’ve discussed before, in D&D, success rarely comes from one hero acting alone. The party needs to share ideas, coordinate strategies, and support each other through challenges. This collaboration creates a natural environment for coaching moments. Here are a few examples:

  • Encouraging quieter voices: A player who hesitates to speak up can be brought into the conversation by gentle prompts—“What does your rogue think about this plan?”—mirroring how a leader ensures all team members contribute.
  • Asking guiding questions: Instead of dictating solutions, you can ask your fellow players questions that help them find their own answers. “What would your character want to do here?” is not far from “What do you think the best next step for this project is?”
  • Building confidence: Just like a Dungeon Master might celebrate creative problem-solving, leaders can acknowledge small wins that encourage team members to take on bigger challenges.

Coaching Lessons at the Table

I must caveat the following with he fact that I am not a coach, but i have benefitted greatly through being coached. I am also purposeful in trying to use coaching techniques with both my own team members and D&D table. Through roleplay and problem-solving, you learn practical coaching behaviors. Here are a few to consider at your next session:

  1. Active Listening: D&D demands attention. A missed detail could mean falling into a trap, and in leadership, missing someone’s concern can erode trust. Listening closely to others’ words—especially what’s between the lines—builds empathy and understanding.
  2. Empowerment Over Direction: In-game, it’s tempting to tell others what the “best move” is. But the best D&D sessions happen when everyone feels ownership of their choices. Leaders, too, unlock the best results by empowering rather than directing.
  3. Creating Safe Spaces for Experimentation: A D&D table is a place where failure isn’t the end, just the next step in the story. Leaders who coach with the same mindset—viewing setbacks as learning opportunities—help their teams grow stronger.

Bringing Coaching from the Table to the Workplace

When you carry these habits into your leadership, you stop being the person with all the answers and start becoming someone who brings out the best in others. This includes:

  • Encouraging team members to develop their own solutions.
  • Supporting people to step into roles they might not initially feel ready for.
  • Helping build a culture where experimentation is valued, not feared.

That’s the essence of coaching. And what’s remarkable is that, for D&D players, this skillset grows naturally through play.

Final Thoughts

Every great adventuring party needs someone who can support, guide, and lift others up. In the same way, every great workplace needs leaders who coach. If you want to practice those skills in a low-stakes, creative, and fun environment, there’s no better training ground than a session of Dungeons & Dragons.

In a couple of weeks I’ll post an article that will explore some practical tips to help get thinking and acting more like a coach.

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Dealing with a Lone Wolf Player in D&D and Business

We all know that in both Dungeons & Dragons (D&D) and the workplace, teamwork is essential for success. However, every group occasionally encounters a lone wolf—an individual who prefers to act independently rather than collaborate with the team. While independence can be a valuable trait in certain situations, a lone wolf’s behavior can be detrimental when it disrupts group cohesion, communication, and shared objectives. If left unchecked, a lone wolf can cause irreparable damage to a business or group.

What Is a Lone Wolf and Why Is It Detrimental?

A lone wolf is a player or employee who operates primarily on their own, often avoiding teamwork, disregarding group plans, and making decisions without consulting others. In D&D, this could be a character sneaking off to loot treasure without the party, or a player who constantly ignores group discussions in favor of their own agenda. In business, a lone wolf might be an employee who works in isolation, hoards information, doesn’t follow process or fails to engage in team projects.

Often individually a lone wolf can be successful. For example make great sales, or make a great in game fighter. However, their unwillingness to collaborate can cause significant issues, including:

  • Lack of synergy: The group is forced to work around the individual rather than integrating them into team efforts.
  • Poor communication: Important details are missed because the lone wolf operates separately.
  • Reduced trust: Team members may feel frustrated or disconnected when the individual ignores their input.
  • Lower efficiency: The group wastes time resolving conflicts instead of focusing on their shared goals.

Strategies for Dealing with a Lone Wolf in D&D

As a Dungeon Master, your goal is to balance individual player agency with team cohesion. Here are some ways to handle a lone wolf player effectively:

  1. Understand Their Motivation – Talk to the player to understand why they prefer to work alone. Are they roleplaying a specific character concept, or do they simply dislike group decision-making?
  2. Encourage Group Decision-Making – Implement moments where cooperation is necessary, such as puzzles, multi-step combat strategies, or social encounters requiring group input.
  3. Use Narrative Consequences – If the lone wolf consistently acts against the party’s interests, have the world react accordingly. NPCs may become untrusting, or the character may face in-game consequences for their isolationist behavior.
  4. Set Clear Expectations – Before the game, establish that D&D is a cooperative experience and that all players should engage with the group’s decisions.

Strategies for Dealing with a Lone Wolf in Business

Managing a lone wolf employee requires a balance of respecting their independence while ensuring they contribute to the team’s success. Here’s how leaders can address this behavior:

  1. Identify the Root Cause – Is the employee avoiding teamwork due to a lack of trust, unclear expectations, or personal preference? Understanding their reasoning helps tailor your approach.
  2. Encourage Open Communication – Lone wolves may not realize how their actions impact the team. Provide regular feedback and encourage dialogue to align them with team goals.
  3. Assign Team-Oriented Tasks – Give them projects that require collaboration, emphasizing shared success over individual achievement.
  4. Create Accountability – Ensure that responsibilities are clearly defined and that the lone wolf must provide updates and integrate their work with the team’s efforts.

Final Thoughts

While implementing the strategies above should bring a lone wolf around to integrating more with the team, there will be instances where they will refuse to do so. If this is the case and their behavior is having a detrimental impact on the team then you should seriously consider asking them to leave the gaming group. Or, in the case of a workplace begin enacting performance management. However, DMs and leaders alike can turn a lone wolf into a valuable team player. Whether in fantasy or the workplace, the best adventures—and successes—are built on cooperation.

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When Rival Parties Enter the Dungeon: Competition and Time Pressure

Most of the time when we think of Dungeons & Dragons, we picture a single party of adventurers delving into a dungeon, working together, fighting monsters, and uncovering treasure. But what if there were two rival parties competing for the same goal, racing against each other in real time?

I first came across this idea listening to the excellent podcast Fear of a Black Dragon, where presenter Tom McGrenery described running the Dungeon Crawl Classics adventure Piercing the Demon’s Eye for two groups at the same time. It sounded chaotic, exhilarating, and utterly brilliant.

So of course, I had to try it.

Did it work? Read on to find out.

Two DMs, Two Rival Parties

Together with my fellow DM Rich, we set up a dungeon crawl for ten friends. The twist? Instead of one unwieldy group of ten, we’re splitting them into two rival parties, entering the dungeon (Piercing the Demons Eye) five minutes apart.

The rules of engagement are simple:

  • The dungeon closes in four real-time hours. When the clock hits zero, the dungeon magically shuts. Any characters still in there are trapped, experiencing a slow and agonizing death.
  • The party with the most loot wins. If they make it out in time.
  • We’ll keep tension high with regular real-time countdowns, making every decision feel urgent. One player from each team will be designated time keeper, reminding their team mates to keep moving, or to escape.
  • On top of that, we’re borrowing a mechanic from Blades in the Dark: each time a spell is cast, a clock ticks forward. When it fills, something catastrophic is unleashed into the dungeon.

It’s part dungeon crawl, part pressure cooker, part competitive sport.

What Does This Have to Do With Leadership?

At first glance, this might just sound like a fun twist on D&D (and it absolutely will be). But it’s also a fascinating experiment in leadership under stress. Competition changes everything. When you know another team is out there grabbing treasure, time suddenly becomes your most precious resource. Leaders in the group will have to:

  • Prioritize quickly: Is it worth taking that side passage, or should we push deeper?
  • Manage risk: Do we burn spells now, advancing faster but bringing the catastrophic clock closer to midnight?
  • Balance the team’s needs: Some players may want to fight everything. Others may want to sneak past. Good leadership will mean finding the middle path without wasting precious time.

These dynamics mirror real-world leadership challenges.

Similar scenarios could be run as part of a leadership training exercise. Imagine putting your aspiring leaders through these:

  • Two groups of scavengers in a zombie apocalypse racing to loot supplies before winter. Only one settlement will thrive.
  • Rival companies bidding for the same contract, knowing only one can succeed.
  • Disaster response teams in a crisis where resources are shared between teams and time is brutally limited.

In each case, leaders need to stay calm, make rapid but thoughtful decisions, and keep their team united under pressure.

All of these scenarios can be run using my simple, easy to run Play to Lead ruleset.

Why This Works for Leadership Training

What makes games like this so effective for leadership development is that they feel real. As Jennifer Ouellette explains in Me, Myself, and Why, our brains encode roleplaying experiences as though they genuinely happened. That means when you practice making tough calls, prioritizing under pressure, and communicating clearly in a D&D dungeon, you’re exercising the same leadership “muscles” you’ll use in the workplace.

Adding competition into the mix elevates the stakes. The stress is simulated, but the feelings of urgency, pressure, and rivalry are real enough to create meaningful growth.

Bringing It Back to Work

If you want to use this kind of scenario in a leadership training environment, here are some tweaks:

  • Theme it for your group: Instead of fantasy loot, consider one of the alternative scenarios mentioned above.
  • Make consequences clear: Limited time, limited resources, and a final score that determines success or failure.
  • Encourage reflection afterwards: The real learning happens when teams debrief what worked, what didn’t, and how leadership showed up under pressure.
The happy participants!

Running the Game

What a blast to run! Rich had booked a community hall for the event. Everyone was primed to bring two 5E D&D characters, just in case. First we used a dice bag with coloured dice to randomly assign the teams. After explaining the premise we set the 4 hour timer and we were off.

Rich and I passed each other notes as the adventurers made their way through the dungeon. The players tables were facing each other so they were always aware of the rival party and their progress. Some of the highlights from the game were:

  • One party coming upon the other and sending an owl to trail them.
  • The first party setting traps for the second.
  • One party battling for their lives, the second popped their head in the room before beating a hasty exit.
  • The slow realisation that casting spells had an impact on the dungeon clock, but not knowing quite what it was counting down to.
  • One player sifting through the treasure horde and throwing unwanted bits into oblivion.

The teams were going to be judged by how much treasure they retrieved. So I made a series of treasure cards describing what they found, but with no value written on them. At the end of the session we totaled up the value of the rescued valuables to determine a winner. There was only 100gp between the two parties!

That being said noone actually made it out alive……

This photo shows our set up. DMs back to back, the bright yellow clock countdown to the left.

Did it Work?

Absolutely it did! The players really got into the premise of the game and told us it was a completely different experience to anything else they had played. There was great banter between the tables and the debrief dinner afterwards was great fun as they pieced together what each rival party had been up to.

Rich and I worked really well as a team. Luckily we had done a load of prep before hand so we knew the module well and how we were going to handle different parts of it. Passing notes between ourselves also added additional paranoia to the players. Always a win.

One interesting thing was that the players actually engaged with the adventure faster then we though they would. Between the two teams they covered every room and trap. This is a good lesson for next time.

I also made a mistake where my group were moving much faster than the others and caught them up without me realising. So we had two parties in the same place at the same time without seeing each other. Woops. Not to worry though, once I’d worked it out I managed to stall my guys long enough for it all to settle out again.

Final Thoughts

In the end, this experiment is both a thrilling way to play D&D and a powerful way to test leadership under competition and time stress. When two parties enter the dungeon, only one comes out on top—but everyone comes out having had a different and fun experience.

If this sort of thing appeals to you I would strongly suggest grabbing a co-DM and running this for your friends. It was a memorable event for everyone, with lots of pressure, paranoia and of course laughter.