Tag: Leadership

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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.

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Leadership Is a Muscle—And You Need to Train It

business man training his leadership muscle

We all know the value of exercise. You go to the gym to lift weights, run on the treadmill, or maybe stretch through a yoga class. Each of these activities targets different aspects of your physical health: strength, stamina, flexibility. If you don’t exercise those muscles, they weaken over time. Of course, Leadership is no different. Being an effective leader isn’t a fixed trait—it’s a skillset. And like your biceps or your lungs, those skills need intentional training to stay sharp and healthy. You can’t expect to be at your best if you never put them under purposeful stress. How do we train our leadership muscle?

Training Your Leadership Muscle at Work

In the workplace, this means being deliberate. You can:

  • Practice communication: Share openly, listen actively, and make sure your team understands not just what you’re saying, but why.
  • Build self-awareness: Take time to reflect on how you show up for your team, what went well, and where you can improve.
  • Be purposeful: Don’t just drift from meeting to meeting—set clear intentions about how you want to show up as a leader that day.

These small acts, repeated, strengthen your “leadership core.”

Another Gym for Leaders

Here’s where it gets interesting. You don’t have to limit leadership practice to the office. Just as athletes cross-train with different sports, leaders can cross-train with games.

Given the theme of this blog we’ll take Dungeons & Dragons as an example. At first glance, it’s a fantasy roleplaying game filled with dice, dragons, and dungeons. But beneath the surface, it’s an intricate leadership laboratory.

  • As a Dungeon Master, you’re practicing facilitation, storytelling, and group management—all while balancing competing needs and personalities.
  • As a player, you’re practicing collaboration, decision-making under uncertainty, and influencing a group without dominating it.

What’s fascinating is that, as science writer Jennifer Ouellette explains in Me, Myself and Why, our brains treat these imagined experiences as real. When you roleplay leading a group through a perilous dungeon, your memory encodes it as though you actually led people through challenges. That means the leadership muscles you work in a game session can directly strengthen the ones you’ll use in Monday’s staff meeting.

Games can be a useful gym in which to train your leadership muscle.

Purposeful Play as Practice

Think of it this way:

  • A high-stakes project deadline is like a boss battle.
  • Negotiating with a client isn’t all that different from convincing a suspicious NPC to help your party.
  • Balancing diverse team needs mirrors balancing a party of adventurers with wildly different skills and motivations.

If you approach these game scenarios with intentionality—practicing clear communication, reflection, and purposeful decision-making—you’re training your leadership muscles in a safe but meaningful environment.

Keep Your Leadership Strong

Just like the gym, leadership training isn’t a one-and-done activity. You need to keep working at it. At work, in life, and yes—even in play.

So next time you roll dice at the table, don’t think of it as just a game. Think of it as a workout for your leadership. The more you train, the stronger you get.

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Session Zero and Leadership: Setting the Tone for Success

When you start a new Dungeons & Dragons campaign, there’s a piece of advice that experienced Dungeon Masters repeat over and over: “Run a Session Zero.” This is the meeting before the adventure begins—the chance to talk through what kind of game you’re playing, what the players can expect, and what’s expected of them.
Done well, it prevents mismatched expectations, unnecessary conflict, and disappointment down the road.

And here’s the thing: if you’ve ever stepped into a leadership role in the workplace, you’ve already run something like a Session Zero—or you really should have. Taking on a new leadership role requires the setting of expectations as early as possible.

So, Whether you’re gathering your adventuring party or leading a new team, the principle is the same: Set expectations early, clearly, and collaboratively.

What’s a Session Zero in D&D?

Session Zero happens before the first dice are rolled and before any characters are created. It’s where you cover things like:

  • Game tone – Is this a gritty, survival-focused story or a lighthearted romp through the realms?
  • Table etiquette – How do we handle disagreements? Phones at the table—okay or no?
  • Content boundaries – What topics are off-limits to keep the game safe and fun?
  • Player goals – Do they want deep character arcs, tactical combat, or puzzle solving?
  • Your role as DM – How you’ll run the game, your style of storytelling, and how flexible you are.

The point isn’t to lecture—it’s to make sure everyone knows how the game will work, what they can bring to it, and what they’ll get out of it. Players also play a role here, and a good DM will aim to incorporate their expectations into the session as well.

Why Leaders Need a “Session Zero” Too

When you step into leadership, your new team is looking for the same types of clarity. They want to know:

  • The mission – What are we working towards?
  • The culture – How do we operate together day-to-day?
  • Boundaries – What’s non-negotiable, and where is there flexibility?
  • Your style – How do you make decisions? How do you give feedback?
  • What you expect of them – Effort, communication, collaboration, deadlines.

And just like a DM, you’re also telling them: Here’s what you can expect from me.

That might include:

  • Transparency about decisions.
  • Support when things get tough.
  • Respect for work–life balance.
  • An open door for concerns or ideas.

This conversation has to go both ways and a good leader will aim to understand their new team members expectations also. Without this up-front conversation, teams can quickly run into “mismatched game” problems—where some think it’s all about speed, others think it’s about perfection, and no one’s sure which one will get rewarded.

The Mutual Expectations Loop

As alluded to above, in both D&D and leadership, expectation-setting isn’t one-way.
It’s not just “Here’s the list of rules.” People at the game table or the boardroom table will turn off at that.

Instead, it’s a two-way agreement, for example:

  1. You share your expectations of them.
    • Players: Be on time, respect each other’s spotlight, communicate your goals for the character.
    • Team members: Collaborate, meet deadlines, raise risks early.
  2. They share their expectations of you.
    • Players: “I’d like more roleplay than combat” or “I’d rather keep sessions under three hours.”
    • Team members: “I value regular feedback” or “I work best with clear priorities.”

This loop ensures no one’s surprised later. In a D&D game, it means fewer awkward “That’s not the kind of game I signed up for” moments. In a workplace, it means fewer frustrations, missed deadlines, or most importantly disengaged employees.

The Session Zero Payoff

When everyone is on the same page from the start:

  • The game flows better.
  • The team works more smoothly.
  • Challenges feel like shared puzzles to solve, not personal obstacles.
  • Trust builds faster.

A Session Zero in D&D might only take an hour, but it can save a whole campaign from crumbling. Similarly, a “leadership Session Zero” might take a single team meeting, but it can set the foundation for years of collaboration.

Final Thought:

When using Session Zero’s in both D&D and leadership, you’re not just setting rules—you’re setting the culture. Your Session Zero, whether at the table or in the office, tells everyone:
“Here’s how we’re going to succeed together.” Effectively setting your game or team up for success right at the very beginning.

Below is a quick reference sheet to help guide your Session Zero, whether at the game table or at work.

DnD at Work Session Zero ChecklistDownload

You can download this and other resources here.

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Fast, Fun, and Focused: Using Character Playbooks to Enhance Your Game

Character Playbooks

Character creation is often one of the most exciting, and sometimes most daunting, parts of starting a new roleplaying game. For many, it’s a chance to dream up a bold new identity. For others, it’s a speed bump they need to get through before the fun begins. That’s where character playbooks come in.

Popularized by games like Blades in the Dark and Dungeon World, playbooks are pre-structured character archetypes that bundle together key decisions: attributes, gear, special moves, and even personality prompts. Making each character feel distinctive and unique. They let players jump into the action fast, without sacrificing the creativity and individuality that make roleplaying so engaging.

But playbooks aren’t just great for steampunk heists or fantastical dungeon crawls—they’re also an incredible tool for leadership-focused RPGs and team training games like my own Play2Lead.

What Makes Playbooks Powerful?

At their core, playbooks do three key things:

  1. Simplify Decision-Making: Instead of choosing from dozens of classes, feats, skills, and powers, players select a playbook and make a few meaningful choices within it. This lowers the cognitive load and keeps the game moving, while still making character creation meaningful.
  2. Set Expectations: A Cutter in Blades in the Dark is likely to be physical, intimidating, and direct. The playbook leads the player in that direction through the choices that it offers. clarity like this really helps players quickly understand their role in the team and how they might contribute.
  3. Encourage Roleplay: Many playbooks include bonds, questions, or prompts that nudge players into thinking about how their character sees the world—and how they’ll interact with the rest of the group.

These features combine to create a quicker, smoother onboarding process—perfect for groups who want to dive into the action or get through a session during a lunch break.

An example of one of the Blades in the Dark Character Playbooks

How Character Playbooks Can Elevate Play2Lead

In my own game Play2Lead, the focus is on leadership, communication, and teamwork in a roleplaying context. It’s a game designed to help people learn by doing—to explore different leadership styles, solve complex problems together, and reflect on how they interact in a group. Currently character creation sits with a broad occupation, leadership style and one stat (exhaustion). Using playbooks might be a quick way for participants to engage with the game and understand what’s expected of them during play.

Here’s how playbooks can serve that mission:

  • Align with Leadership Styles: Playbooks in Play2Lead could represent leadership archetypes: The Visionary, The Facilitator, The Challenger, The Harmoniser, etc. Each one comes with strengths, blind spots, and a unique way of contributing to the team.
  • Jumpstart the Game: With predefined goals, triggers, and interpersonal dynamics, players can hit the ground running. This is especially helpful in one-shot sessions or corporate workshops where time is limited. You could also include a differing objective for each player, letting them work through conflict and compromise.
  • Create Teachable Moments: By embedding questions like “What do you do when your suggestion is ignored?” or “How do you handle team conflict?”, playbooks can gently guide players into valuable moments of reflection and growth.

Overall including a playbook system in Play2Lead is a great way to create more depth into the scenarios. Now instead of just trying to escape the Lost Temple, we can include interparty conflict and different objectives that better reflect teams in the real world.

Using Playbooks with Traditional D&D-Style Games

Playbooks aren’t exclusive to narrative indie RPGs—they can be layered onto more rules-heavy systems like Dungeons & Dragons to help get new or time-strapped players into the story faster. Imagine starting a D&D one-shot where the group is a squad of mercenaries. Each player picks a playbook with questions like:

  • The Veteran (Fighter/Leader) – “Who saved your life once, and what do you owe them?”
  • The Scout (Rogue/Observer) – “What truth have you discovered that no one else believes?”
  • The Mystic (Cleric/Wild Card) – “What vision haunts your dreams, and how does it shape your choices?”

These pre-framed characters help players understand not only what their characters can do, but also who they are, and why they’re involved in the mission. You don’t need to rewrite the D&D rulebook—just wrap character choices in storytelling scaffolding that speeds things up and adds emotional depth.

For inspiration, Simon Carryer has developed some great playbooks for older versions of D&D, check them out here.

Making Your Own Playbooks

Creating your own playbooks is easier than it sounds. Think of it like designing a template that sparks imagination while setting clear boundaries. Here’s a quick method:

  1. Define the Role: What job does this character do in the team? What are they responsible for?
  2. List Core Abilities: Pick 2-3 key strengths. Keep the wording accessible: “You keep the group calm in crisis” is better than “+2 to Persuasion.”
  3. Add Unique Moves or Perks: Give each playbook one or two special abilities or tools that make them distinct.
  4. Prompt Player Reflection: Include a few questions about values, goals, or backstory. These help the player bring the character to life in their own way.
  5. Include Interpersonal Hooks: Write 2-3 “bonds” or connections to other team members. These generate immediate relationships and drama.

Final Thoughts on Character Playbooks

Playbooks are more than shortcuts—they’re powerful frameworks for story and chartacter depth. Whether you’re sneaking through a haunted city in Blades in the Dark, solving a leadership challenge in Play2Lead, or running a team-building D&D session, playbooks help players connect quickly, act decisively, and reflect meaningfully.

So next time you’re planning a game—whether for fun, training, or both—consider developing some playbooks. You’ll be amazed at how fast your players step into the story and start leading.