I have a confession to make.
I have been routinely engaging in conflict-resolution sessions with a group of creative, talented mid-career professionals. We have been collaborating on solutions to complicated, high-stakes problems by drawing on the unique strengths and talents of each individual. Throughout, I have been supporting them in building skills and developing character to overcome increasingly greater challenges in their respective and ever-widening domains of influence.
Of course, I am not talking about my career as a CTO. I am talking about being a dungeon master for the popular Dungeons & Dragons® (D&D®) role-playing game.
In a previous article, I mention how my trusted Getting Things Done® (GTD®) system has been invaluable to help organise logistics, dip in and out of a complex fantasy world alongside real-world professional commitments, and streamline administration to keep the fun stuff fun.
Looking back 25 years to my first experiences as a dungeon master, I also realise that this role helped me to develop important leadership skills that have served me throughout my career as an IT executive. It was the application of the GTD methodology, however, that allowed me to put these skills into practice in an effective way.
For those of you unfamiliar with the game, unlike reading a novel, D&D involves shared storytelling. Several players assume the role of the ‘main characters’ in the story, and a single dungeon master controls everything else in the world – from allies to monsters to fantastic terrain. Players have free choice, so they can attempt do anything they like within this world. Some outcomes are more likely than others, however, so a complex set of rules combined with the roll of the dice (literally) determines each result. Therefore, the dungeon master’s motto, like the title of GTD creator David Allen’s second book, really should be ‘ready for anything’.
Is any of this starting to sound familiar?
As seasoned Dungeon Master Davena Oaks put it, “No plan survives contact with the players”. As most equally seasoned executives, and especially those in IT know, few boardroom mandates survive contact with the execution team, either. While some outcomes are more likely based on the skill of the players involved, trying to “script” complex change like a novel leads to suboptimal results and frustrated participants. Yet going into the game completely unprepared is a recipe for disaster as well.
This is where outcome-orientated thinking becomes so critical in collaborative situations. The best leaders I have encountered are those who have been able to create inspiring clarity about where we are headed, and then manage the journey with an improvisational ‘light touch’ along the way. I have found no better way to represent and track the details of this approach than to use the fundamental GTD thought process of defining visionary project outcomes and clear, doable next actions.
The temptation to fill in everything else from start to finish is a natural impulse to try to gain control. Ironically, real control in dynamic, collaborative situations comes not from ‘railroading’ everyone down a pre-set path (as it is disparagingly known in the D&D world), but in continuously adjusting in relation to a shared goal. Those adjustments can really only happen one next action (or dice roll) at a time.
So, whether your team is up against a dragon or a BHAG, mapping an org. chart or an orc chart; making everyone a part of the success story involves the fine art of balancing clarity with flexibility. The GTD methodology gives you some of the best artist’s tools I know to make that happen.
GTD & Getting Things Done are registered trademarks of the David Allen Company. D&D and Dungeons & Dragons are registered trademarks of Wizards of the Coast LLC.
Having several year as a “chararcter” in role playing environments as well, I have to say that this article really resonated very well with me. Interesting from my perspective is that what you describe here matches nearly perfectly the agile world we expeirence more and more (not only in IT).
One question though: I wonder how you deal with overly rigid “players” (you know, the ones, that say things like “rulebook II pg 17, 3rd paragraph says you have to divide the result by 3.7 and not by 3 aka – business wise – someone that says “I do not want to leave my comfort zone”)…?
It’s a great question, Phil. As a DM, you can often “reroute” that energy by giving them a focus or role that fulfils the positive intent of their behaviour (e.g. making them a DM’s helper who tracks initiative, double-checks rules, etc.). You can also remind them of the bigger-picture intent, which is to have fun and bend rules as needed in service to a great story.
In the business/GTD world, I think this maps to understanding peoples purpose/principles/values, and using that to clearly define goals/vision/areas of focus that are both in alignment their bigger picture and the company’s bigger picture. Making it conscious using the horizons of focus model can help that conversation. Also, setting clear project outcomes as well as defining those standards is often enough to then let them execute on it in whatever style works best for them–including taking a very rules-focused or process-oriented approach where you might have been much more improvisational if doing it yourself.
Defining project outcomes and the standards for communication and success markers along the way can really help leaders to manage toward positive outcomes even when “players” in the “game” have a very different style and approach.
I think it’s just as important to say “what do we want to get out of this and how do we want to agree to all play with each other?” around the gaming table as it is around the meeting room table.
I love your comment about inspiring clarity and light touch. I have to admit, I’ve been guilty of the opposite–heavy-handedness and “structure for structures sake”. How uninspiring is that? I think the creative vision and light touch you suggest is more valuable because it takes a bit of creativity and a leap of faith like “let’s go here and do X” and then the confidence to keep a light touch as you journey off into an uncertain future, but how much more fun and inspiring is that? Thank you!