GTD & D&D Part II: How to Lead a Team of Dragon-Slayers

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.