On the parallel development of a Dungeon Master and a product owner, and what it reveals about leadership.
My son spends his weekends running Dungeons & Dragons campaigns for a group of friends. During the week, he leads a software product team. He has been doing both for a few years now.
The overlap was impossible to ignore for long.
The skills he was developing as a Dungeon Master were showing up directly in his growth as a team leader. The same lessons, arriving through completely different doors.
I am a management consultant. I have spent years trying to articulate what good leadership looks like in practice, rather than in frameworks and slide decks. Watching my son develop in these two roles at once has, unexpectedly, been one of the clearest illustrations I have encountered.
Here is what both roles teach him.
1. Prepare thoroughly. Hold the plan loosely.
A Dungeon Master builds a world before the session begins: maps, characters, and cause and effect. But experienced DMs know what beginners must learn through failure. The players will immediately go somewhere unplanned. The preparation is not a script. It is a foundation you stand on while improvising.
Good leaders do exactly this. A roadmap and a set of priorities provide direction. The moment you confuse the plan with the outcome, you become fragile. The market shifts. A key person leaves. A dependency you relied on disappears.
The skill is knowing what must be decided now and what can be deferred. A plan that cannot bend is not a plan. It is a wish with a Gantt chart attached.
2. Peripheral attention is a professional discipline.
A good DM tracks five or six people at once: who is engaged, who is restless, and who has gone quiet and needs something before checking out entirely. This is not passive. It is continuous, deliberate attention across multiple people at once.
Leadership works the same way. The team member who says nothing in a meeting is telling you something. The one who used to push back on decisions and has stopped: that is a signal, too. The leaders who lose their best people are almost always surprised. They were not watching.
You cannot manage with dashboards alone. At some point, the most important data is in the room.
3. Make confident decisions with incomplete information.
Something goes wrong mid-session, and the DM has a few seconds to respond in a way that keeps the story coherent and the players moving. No time to consult anything. Just the call.
Every leader who has managed a crisis, a sudden pivot, or a high-stakes conversation under pressure knows this feeling. The question is not whether you can think clearly amid uncertainty. You will have to. The question is whether you have built mental models good enough to act on when the moment comes.
Hesitation costs more than a wrong decision you can correct. The team needs direction more than a perfect answer.
4. Default to “yes, and,” not “no, but.”
The best DMs find ways to incorporate what players attempt rather than blocking them. A player proposes something unexpected. The DM makes it work. The players feel heard, and the story becomes theirs, not merely the DM’s.
When a team member proposes an approach you would not have chosen, many managers default to explaining why it would not work. The better move is to ask what would need to be true for it to work well.
Your job as a leader is not to impose your preferences on the team’s output. It is to create the conditions for others to do their best thinking. Most of the time, their best thinking is better than your first instinct.
5. Different people find different things meaningful. Build for all of them.
Every D&D party has the player who wants an epic narrative, the one who wants tactical complexity, and the one who is mostly there for the experience of doing something together. A good DM does not force all three into the same session.
Every team has the same variation. One person wants hard, complex problems. Another wants to see their work reach real users. A third wants clear structure and predictability. Optimize your leadership for only one of these, and you keep that person while gradually losing the rest.
Understanding what each person finds meaningful and creating an environment where those different sources of meaning can coexist are design problems. They are also among the most underrated skills in management.
6. Consistency in small things builds trust for large moments.
In a well-run campaign, the rules work the same way every time. Players can plan and predict. They trust the world they are in. When a DM arbitrarily breaks their own rules, the world loses credibility, and the players stop caring.
Organizations work the same way. The norms for how decisions are made, how feedback is given, and how conflicts are resolved: these are the internal rules. Teams that trust their leaders take risks, raise problems early, and engage rather than protect themselves.
Credibility is not built in a single dramatic moment. It builds slowly, through a long series of ordinary moments that all point in the same direction.
7. Let consequences land.
One of the hardest DM skills is not rescuing players from their bad decisions. If they ignore a warning and walk into a trap, the trap closes. Not out of cruelty. That is how learning happens. The story becomes real because consequences are real.
This is one of the hardest leadership skills, too. When a team makes a poor call and the result is visible, the instinct is to absorb it on their behalf: fix it quietly, smooth it over, and move on. This protects no one and teaches nothing.
People grow when they feel the weight of their choices. Teams improve when they genuinely reflect on what went wrong and why. Real accountability requires real consequences. You cannot shortcut it.
What the parallel reveals.
The deepest lesson both roles teach is the same, reached from opposite directions.
The DM’s job is to give others a great experience. The team leader’s job is to create the conditions for others to do their best work. Both roles require getting genuinely comfortable being the person who makes everything possible while staying largely out of the way when things go well.
This is harder than it sounds. Most people who want to lead also hold strong views about how things should be done. The transition from doing to enabling requires a particular kind of letting go that rarely gets discussed directly.
What strikes me about watching my son navigate both roles is that neither role lets him avoid that transition. The game and the job keep returning him to the same question: is this about you, or is it about them?
In both cases, the answer is the same.
Dane Thomas is a Senior Management Consultant and ITIL 4 Master at BiTA Service Management in Stockholm. He writes about leadership, organizational capability, and the unexpected places where good ideas emerge.
This article was first published on Substack on April 30, 2026.