5 Lessons on Leadership from the Dungeon Master's table

Disclaimer: A bit about the title ‘dungeon master’. The term is the one I have applied to myself for more years than I have been part of the work force, and I know within those circles the term could also be ‘game master’, ‘storyteller’, or ‘Keeper of Arcane Lore’. For this article I will use Dungeon Master and DM as it’s short form.

Enjoy. TLDR at the bottom.

This is the Introduction, Skip to Lesson 1 if you prefer no context

When I had my first management position, I was 16 years old and had taken over as ‘shift leader’ at a local Taco Bell. It’s fair to say that I had no idea whatsoever of what I should do as a manager other than to make sure the work was done, people took breaks at certain times, and all work was reviewed at the end of the night. My boss at the time, a no-nonsense style boss told me,

It’s easy to be the boss – just make sure you know every job better than the person doing it and make sure they know that. :(

My second time in management was a few years later where I managed a toy department at a Wal-Mart. Like the first role my focus was mostly on scheduling, ordering product, making sure the department was clean, and getting along with other department heads. The store manager worked like he was Elon Musk and the store ran smoothly; but it was clear that the manager was perpetually exhausted, short of patience, and in a hurry.

The store ran well, so I believed a good manager meant a person who worked hundreds of hours a week and made sure everyone did their job properly.

Today I may call what he did micromanagement, but just because I don’t like to work that way doesn’t mean it didn’t work. His results were spectacular for Wal-Mart and he continued his success at the company.

               Fast forward years and I had another management role, but this time in corporate. I had to manage a team of hardworking, intelligent, and focused people who were trying to get important work done. They also had to maintain relationships with their partners, take care of children, social responsibilities, part time classes, and an unfathomable number of other activities that most of us work hard at in our own lives but sometimes forget other people do as well.

My job was no longer simply to manage schedules or ensure the shelves were stocked – there was an expectation that I would legitimately manage these individuals – something I had not truly done in previous jobs.

With very limited experience to work with I plunged head long into the position to lead the best I could. What I discovered was lessons I still use to this day and the alternative title to this article: “Everything I learned about leadership, I learned from D&D”

Lesson 1: Know your players

               As a novice Dungeon Master I would create what I thought were wonderfully engaging adventures where players could do battle, solve nasty puzzles, or find fantastical treasures. What I discovered early on is the engagement of some players was high and others were low. Wanting to study the problem more carefully I watched, and noted, when players were interested and when they weren’t, what kinds of interactions they craved and what kind of characters they played. It quickly became clear that there were obvious patterns – if only I had paid attention. The different players had different goals and desires, different story elements that kept them interested and others that bored them to tears.

               The same holds true for a leader; the people around you have different motivations and interests.

Some will keep focus if you give them access to the latest technology, some will be interested in pursuing difficult problems, some want their work to change the world, others want to get home in time to take care of their children, and a few simply want promotions and wealth. You must know the people who work for you, and they in turn must know the people who work for them. If you are not certain of what motivates the people who work for you – look deeper and see if you can find the pattern.

When are they most motivated?

When are they least motivated?

What tasks do they avoid, and which do they happily accept?

 Knowing what people want is the only way to motivate them.

Lesson 2: Don’t say no, determine difficulty

               As a DM you spend countless hours discussing with players plans that are well outside of the rule book or to which there is no obvious answer. I’ve had characters use low-level magic spells to break down walls by targeting sub-components (not addressed in the rules).

I’ve had characters attempt to move objects huge distances since transferring an item to another person is a certain kind of action by rule. I’ve had characters use a magical item known as an ‘instant fortress’ to try and drop a castle on their enemies. Any DM who sat at the table knows the feeling of being asked if a player can do something that is clearly in the grey area of the rules and being forced to come up with some way to make this action work (or not) within the confines of the world. This is where the second lesson comes in, don’t just say no to an action – try to calculate how hard it would be to do. This heuristic works well in all but the most absurd of cases in both leadership and DMing.

               We will not always succeed in the work that we do, and sometimes the sheer volume of work that comes at us is difficult to manage. That is no reason though to deny a customer (internal or external) the opportunity to get work done. Too often I hear people saying ‘no’ to their customers, bosses, coworkers, or clients in the field. While it may be appropriate to say no when the feasibility of an effort is close to zero, I often instead hear no when it is simply more difficult than the person wants to do.

               This does not mean the opposite is wise, to work hundreds of hours to please everyone. Instead the strategy is the same used by a good DM, determine difficulty. When a customer, coworker, boss, or client asks for an effort that you would ordinarily say ‘no’ to instead tell them how difficult it would be.

Tell them in concrete terms and, if needed, ask for more time to give them a reasonable answer. It is a lot easier to say, “Yes we could do that, and it would cost us about 250,000$ and take about six months”. This can also lead to difficulty as well as people may challenge the assumption. The same response can be given, “I can get you a better answer but that would take a few weeks and cost a few thousand dollars to build an estimate”. What you may find is that you receive more resources and greater responsibility.

Just make sure that you fund adequate time and people to cover the extra work for you as well – don’t end up like my old store manager.

Lesson 3: The Players matter more than your Story

               A difficult lesson to learn for a novice DM, as he looks upon the shattered elements of his story, is that no story lasts past the first touch of a player. The carefully woven story that you had in your mind will quickly fall apart as soon as the first steps are taken.

This is ok.

               The people who you lead are more important than the work you are trying to do. This may seem counter-intuitive, after all what is the purpose of the people who are working if not to get the job done? As a DM you must tell a good story and run a good game, even when the players veer completely off course.

As a leader you must keep your people motivated and find a way to meet the objectives even when your people seem to be going in a strange direction. There may be good reason for the deviation, and it may help to watch carefully and see where the work goes. It could be what they are doing turns out to be more important than your precious plan.

               Help them achieve and your people will reward you with good work. Your most important priority is to help grow your people, if there are failures and stumbles on the road it is more important to support your people than it is to avoid the failures (unless of course they are genuinely catastrophic for the business). 

For a leader nothing is more important than hiring and retaining good talent – if you have done that part of the job right trust that your people know what they are doing and support them.

Lesson 4: Create a good villain

               In DMing there are few things more memorable than a good villain. Usually the villain takes a familiar shape as an adversary gleefully trying to do some horrible evil to the world due to their capricious nature out of some misguided and twisted belief system. This is the archetypes we are familiar with not just in Role-Playing but also in movies, books, and most forms of media. The villain can have other faces though; the crowd or the bureaucracy can be the villain.

The villain can take the shape of the environment itself or be the persons own inner demons. We can take this parallel into our working world.

We work as a team to complete work, we don’t really have villains to defeat, do we?

People desire an adversary; they often crave an enemy to crush or an opponent to defeat. Some people are motivated simply by superiority (in which case either they are the enemy they strive against or, secretly, everyone is an opponent to be overcome) but most people are motivated by external stimuli. At work that means that your team, group, or company should be doing battle against an enemy. The risk of not creating a villain, of not focusing the group on an evil to overcome is that people will often create their own enemies. This can devolve quickly in to infighting where teams look at other teams in the company as their enemies. This is a common problem and can exist even when teams are motivated by an external force, but the problem is much worse when there is no enemy. Quickly the enemy of the marketing department becomes sales, the copy writers hate the publishers, or the network engineers do battle with the application developers in the eternal epic struggle of “I am right, and those people are idiots”.

Guy Kawasaki tells the story better in Art of the Start where he mentions three good choices for a startup to make meaning:

“Increase the quality of life”

“Right a wrong”

“Prevent the end of something good”

These are good places to start when you think about making your villain. The villain that you are defeating can fall in to one of these categories. For a large company this may be easy, Google claims to want to organize the worlds information. For them the enemy is disorganization, their nemesis is the never-ending battle against informational chaos. At scale this works well, but what about at the organizational or department level?

The same rules can apply to your department in the organization. Taking a queue from my own book in the IT world there are few groups whose enemy could be summed up as external inefficiency.

We are striving to slay the villain of inefficiency; we are doing all we can to make epic war against the troglodytes of network slowness. You reframe the conflict as it is not a war against the application developers, it is a joint war against slowness where the developers are our sisters-in-arms against the mighty beast of network saturation. We all want to slay a dragon and be the hero – let your people be the hero.

Lesson 5: Don’t plan, prepare

               A well-built plan falls apart as soon as a player touches it. A well-built plan in the real world often is demolished as soon as reality sets in. Putting aside the discipline of project management I am speaking of planning in the more strategic sense. The DM who plans out each battle or dungeon in detail will be left in the dust when the players skip the dungeon or avoid the battle – suddenly looking to fill the next 5 hours of play time with wits.

               The other side is a DM who has prepared for the session. This DM has non-playing characters pre-built, a dungeon with a basic map setup, some rooms filled in for good measure. The DM knows the villain and has ensured they are somewhere within the world the players interact with. The DM has some plot-hooks (story devices to drive action forward) that the players could take but may not. In the end this DM is ready for everything without the need for the detailed plan of the DM who misjudged his next adventure.

               A group that bets they know what is coming down the road in five years may be in for a shock if they planned wrong. Agility can help you here, but agility doesn’t want you to plan that far in the future either. Instead of planning, try preparation.

               Consider the world you work in now, in my world of computing there are lots of obvious cycles hitting from all sides. Many of them are older now (like DevOps or Machine Learning) but some are still fairly new (like Continuous Autonomous Validation).

The strategy should not be to simply plan what you will do in the future (we will build a CAV infrastructure) but instead to ensure you have prepared for what the future will bring (we have the tools we need to continue our digital transformation and I am hiring people who want to grow new skills). If you have prepared a solid foundation you will do better than those who planned five years ahead – but were wrong. You will not do as well as the people who planned five years ahead – and were right, but it’s better to be lucky than good. If you can’t make yourself lucky – stick to good. Know your industry, be prepared for what may come, but don’t plan on knowing the future.

               A small caveat, I know some industries have very long lead times, take that suggestion and move the marker to where it is appropriate – we don’t all work in IT.

Summary

               The world of the gaming table is not that different from the world of the corporate boardroom. Both works are about leading people, their expectations, their truth, and their life. If you can understand how best to support the people you work with, or game with, you will have wonderful adventures in work and at the table.

#TLDR

Lesson 1: Know what motivates your people

Lesson 2: Don’t decline a request, find out how hard it is

Lesson 3: People matter more than work

Lesson 4: Slay the dragon

Lesson 5: Be Prepared for the future, but don’t predict it

Other Notes:

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