Managing Up: Successfully Lead from Below in Business and D&D

Managing up, or managing your boss, is an essential skill at work. However, it’s also a concept that can also translate to your Dungeons & Dragons (D&D) games. Learning how to manage up—both with your boss and your Dungeon Master (DM)—can improve your professional performance, foster collaboration, and make the experiences at work and the gaming table smoother for everyone involved.

What Is Managing Up?

In a business sense, managing up refers to the proactive approach you take in working with your boss. It involves understanding their needs, expectations, and communication style to ensure that you’re meeting or exceeding their expectations while maintaining a strong working relationship. It’s not about manipulating your boss, but rather aligning yourself with their goals and needs to improve both your performance and the work environment.

Likewise, in D&D, managing up means working in sync with your DM. The DM, as the storyteller and guide of the game, has a particular vision for the campaign, but as a player, you also have your own ideas and character development to consider. It is all about supporting the DM’s vision while also contributing to the narrative in a meaningful way, ensuring the game remains engaging for everyone.

Managing Up with your Boss

  1. Understand Their Priorities
    The first step to managing up is understanding what your boss values most. Do they care about hitting deadlines, creating innovative solutions, or fostering teamwork? Once you know their priorities, you can tailor your approach and contributions to support those goals. Regular check-ins and open communication can help you stay aligned.
  2. Anticipate Needs
    Being able to anticipate your boss’s needs before they’re asked is a sign of a proactive employee. This could involve preparing reports ahead of time, addressing potential issues, or presenting solutions to problems that haven’t yet been flagged. Proactively offering value makes you a reliable asset and shows initiative.
  3. Communicate Clearly
    Transparency is key in any professional relationship. Keep your boss updated on your progress, flag any obstacles early, and don’t be afraid to ask for clarification or feedback. This clear communication fosters trust and shows that you’re invested in the work.
  4. Be a Problem Solver
    Instead of bringing problems to your boss, try to present solutions as well. This makes you a problem-solver and not just a passive recipient of instructions. Managers often appreciate employees who can think critically and come up with actionable ideas.
  5. Support Their Goals
    Understand the larger goals and objectives of your department or company and look for ways to support them. Your success is tied to the success of the organization, and when you show that you’re aligned with the bigger picture, your boss will notice.
The Game of Thornes is full of leaders and their advisers with plenty of examples of managing up well, and badly…

Managing Up with Your DM

When considering your DM managing up is all about building a cooperative relationship that enhances the fun of the game. DMs put a lot of effort into world-building, crafting storylines, and creating challenges for players. When you manage up in a D&D game, you’re supporting the DM’s narrative while also helping to shape the adventure with your character’s choices.

  1. Understand the Campaign’s Tone and Style
    Every DM runs their game differently. Some favor a gritty, serious atmosphere, while others might lean toward humor and lightheartedness. As a player take time to understand your DM’s style and tailor your actions and roleplaying accordingly. If the campaign is dark and dramatic, try not to disrupt the tone with out-of-place humor or actions that could undermine the immersion.
  2. Contribute to the Story
    D&D is a collaborative storytelling experience. A great way to manage up at the table is to engage with the world the DM creates. Ask questions, develop relationships with characters, and tie your character’s backstory into the ongoing narrative. When you actively contribute to the world, the DM will feel like they’re building a shared story with you.
  3. Respect Their Efforts and Boundaries
    Your DM will appreciate it if you respect the effort they put into crafting the adventure. Don’t push too hard to bend the story to your desires. Instead recognize that the DM has a vision for the game. Work within the boundaries they set while finding ways to enhance the experience.
  4. Be Flexible and Adaptable
    Sometimes, things don’t go as planned in a campaign. A well-prepared DM may have to improvise due to unexpected player decisions. Being flexible and going along with unexpected changes shows respect for the DM’s creative process and keeps the game flowing smoothly.
  5. Give Feedback (Constructively)
    If something is working particularly well in the game, let your DM know! Positive feedback can go a long way in maintaining enthusiasm and improving the quality of the campaign. On the other hand, if something isn’t working for you, express it constructively.

Building Relationships, Both at Work and at the Table

Managing up isn’t just about making sure your boss or DM likes you; it’s about creating a healthy, cooperative environment where you can all succeed. In business, it leads to better performance, more opportunities for growth, and a stronger team dynamic. In D&D, it enhances the narrative, fostering a more engaging experience for everyone. Thereby ensuring that you’re contributing meaningfully to the collaborative story.

Can Roleplaying be Used as a Powerful Forecasting Tool?

using roleplaying as a forecasting tool

I came across this paper titled “Role Playing: A Method to Forecast Decisions” by J Scot Armstrong (2001) a couple of years ago and thought it was worth sharing here. Armstrong’s paper discusses the effectiveness of using role-playing simulations to forecast decisions in various real-world scenarios. It presents five situations where interactions between two parties significantly impact the outcomes. These include labor negotiations, lobbying efforts, product design changes, legal defense strategies, and contract negotiations. The paper argues that using role-playing simulations can help accurately forecasting decisions and their consequences in these complex, interaction focused situations.

It highlights the importance of accurately forecasting the decisions of other parties involved, citing historical examples where inaccurate predictions led to detrimental outcomes. One such example was the failed stock sale of the British-owned Falkland Islands Company to an Argentine consortium in 1975, which ultimately led to the Falkland’s war. Accurate forecasting of each other’s decisions might have prevented the conflict, instead resulting in mutual benefits. The author suggests that role-playing simulations can help improve decision-making accuracy by simulating interactions between parties and predicting their responses to different scenarios.

In many ways this is similar to the concept of Red Teaming. This involves running a simulation with a real opposition force (red team) to test a companies strategies and contingencies. I wrote about Red Teaming and roleplaying games in a previous article here.

Running a Roleplaying Simulation

The paper outlines the basic elements of creating these role-playing simulations. Including realistic casting, clear role instructions, accurate situation descriptions, active participation, and thorough coding of results. It also emphasizes the need for multiple sessions with different scenarios to obtain reliable predictions.

When to Run a Forecasting Simulation

Of course using roleplaying simulations for forecasting does not work for every situation. The paper suggests ideal conditions include: involving conflicts, large changes, or interactions between a few parties. Most important is the need for faction interactions to have a large influence on the outcome.

Is Roleplaying as a Forecasting Tool A Valid Method?

Finally, the paper provides evidence on the value of role-playing simulations, including studies demonstrating their face validity, predictive validity in contrived situations, and effectiveness in predicting decisions in actual situations. It concludes that role-playing simulations offer a valuable method for forecasting decisions and improving decision-making processes in complex scenarios.

An example of a crisis focused forecasting simulation

Final Thoughts

This paper was an interesting read and I could immediately draw parallels with Red Teaming and Megagames in the way the suggested simulations would work. But are companies and other organizations using this methodology? Unfortunately, that is not made clear in the paper. Though we do know that the military do use roleplaying in some of their wargames.

Given the suggested ideal situations and the cost associated with running a roleplaying forecast simulation implies that this methodology would only really be viable for larger organizations. For example, companies like Airbus, Richemont, and HSBC have participated in crisis simulation exercises that involve role-playing to improve decision-making under stress. In fact there is an existing industry providing such services.

Unfortunately, it seems clear that this sort of activity would be of limited use for the small to medium enterprise.

Nonetheless, an interesting journey into another avenue of roleplaying and its use within an organizational setting. Has your company used roleplaying as a forecasting tool?

The Cost of D&D and Warhammer: Are They Really That Expensive?

cost of D&D

Tabletop hobbies like Dungeons & Dragons (D&D) and Warhammer often come with a reputation for being pricey. Between rulebooks, miniatures, dice, paints, and accessories, it’s easy to see why. But how does the cost of D&D and Warhammer stack up against other pastimes? More importantly, are they really as expensive as they seem when you consider the value they provide?

Let’s break it down and explore why these hobbies might just give you the best bang for your buck.

That Initial Sticker Shock

When you’re starting out, the cost of D&D and Warhammer can feel like a big investment:

That’s no small sum. But let’s compare this to other popular leisure activities.

Cost Comparisons: Hobby vs. Entertainment

1. Cinema Nights

A single movie ticket averages around $15. Add popcorn, a drink, and maybe a snack, and you’re looking at $25–$30 for about two hours of entertainment.

  • Annual Cost: If you go to the cinema twice a month, that’s $600+ a year.
  • Value: While a great movie is enjoyable, the experience is fleeting, and you leave with nothing tangible.

2. Video Games

A new video game costs about $60, and you might buy 3–4 games a year. Factor in subscriptions like Xbox Game Pass or PlayStation Plus ($120/year), and your annual expense can climb to $300–$400.

  • Value: Video games can provide dozens of hours of entertainment, but they’re often solo experiences and offer limited creative engagement.

3. Sports and Fitness

Joining a gym or a fitness class can cost over $100 per month, depending on where you live. That’s in excess of $1,200 a year. If you play a team sport, equipment and league fees can add hundreds more.

  • Value: Great for health and social interaction, but the cost often doesn’t include tools for creative or intellectual growth.
D&D and Warhammer are actually good bang for your buck!

The Bang-for-Your-Buck Advantage of D&D and Warhammer

Dungeons & Dragons

  • Initial Cost: $150–$200 for core books and dice.
  • Recurring Costs: Minimal. Many players stick with the same materials for years, and free resources (like online tools and community content) reduce the need for further purchases.
  • Hours of Fun: A single campaign can last months or even years, with weekly sessions that provide hours of entertainment.

The Math: If your group plays weekly for a year (50 sessions), and your setup cost is $200, that’s $4 per session. Compare that to a $15 movie ticket for just two hours!

Reduce your Costs: As a player the cost of D&D can be minimized. You can get away with buying only the players handbook and some dice. There are always second hand versions available reducing the initial cost even more.

Warhammer

  • Initial Cost: $300 for a starter set, paints, and brushes.
  • Recurring Costs: New miniatures and paints can add to the cost, but many players focus on building their collection gradually over time.
  • Hours of Fun: Painting and customizing models alone can provide dozens of hours of creative enjoyment, not to mention the hours spent playing battles with friends.

The Math: If you spend 50 hours painting and 50 hours playing in a year, a $300 investment works out to just $3 per hour. That’s incredible value for a hobby that combines art, strategy, and social interaction.

Reduce your Costs: Of course there is a thriving second hand market for all things Warhammer. Facebook market place and Ebay have huge discounts on pre-loved armies and units. Another way to reduce cost is to start with a smaller game like Kill Team. This skirmish game needs only 10-12 models for an army reducing the initial set up to below $80.

What You Get That Other Hobbies Don’t

1. Creative Engagement

Both D&D and Warhammer are deeply creative hobbies. Writing campaigns, role-playing characters, painting miniatures, and designing battle strategies engage your mind in ways passive entertainment simply can’t.

2. Social Connection

These hobbies are built around shared experiences. Whether it’s laughing with friends at the gaming table or bonding over a close-fought battle, the social value is immense.

3. Lifelong Skills

  • D&D: Enhances storytelling, improvisation, teamwork, and leadership.
  • Warhammer: Builds patience, artistic skills, and strategic thinking.

4. Tangible Rewards

When you finish painting a miniature or complete a campaign journal, you have something to show for your time—something you created with your own hands and imagination. There aren’t many (if any) mainstream entertainment activities that can give you that.

Finding Value on Any Budget

You don’t need to break the bank to enjoy these hobbies. Ways you can further reduce your costs include:

  • For D&D: Free rules are available online, and many campaigns can be played with just a few dice and a borrowed handbook. Theater-of-the-mind play eliminates the need for minis or maps.
  • For Warhammer: Start small with a single squad or box of miniatures. Community groups often trade or sell models, and plenty of budget-friendly paints and tools are available.

The True Value of Hobby Time

Yes, the cost of D&D and Warhammer can be expensive up front. But when you break it down, the cost per hour of enjoyment is actually incredibly low compared to other forms of entertainment. Even better, these hobbies offer something that movies, video games, and gym memberships can’t: a blend of creativity, community, and personal growth.

So, next time someone raises an eyebrow at the price of a rulebook or a box of miniatures, remind them of this: the value of a hobby isn’t just in dollars spent—it’s in the countless hours of joy, connection, and self-expression you get in return.